Journey Outline

• Introduction
• Just Do It 
• Fear
• The Search for Mentors
• Questions to Ask 
• Telling Your Story
• Finding the Right Mentor
• A Mentor Of Your Own
• Doing the Testdrive
• Questions for the Mentor
• Choose a Cheer Leader
• Should You Hire a Coach?
• Listening with Your Heart
• Evaluating the Testdrive
• Not Your Dream Career After All?

INTRODUCTION

Meeting your rolemodels as a concept is almost six hundred years old. People who travel to discover their vocation. As our hero in Midnight in Paris who meets his rolemodels in the night.

After years of fantasy something about living the job and the life for just a few days, weeks or months empowered them to take action. Partly it was the learning – the concrete knowledge they gained about the desired profession or business. Partly it was the mentor who held their hand, boosted their confidence, and offered ongoing help. Partly it was the contacts they made, which made taking the next steps easier.

But above and beyond those practical things, there was something else their journey awakened and energized something deep inside them. It connected them with the truest part of themselves, a part that had previously felt dormant and that, once awakened, refused to be ignored.

You know – if you are considering a dream job – that the push toward a dream career is not just about how you spend your working hours. It is about meshing your work life with your deepest sense of self. It is about having work that matches your values, that feeds instead of exhausts you, that does not require you to leave  your priorities at home and check your heart at the door. When we imagine a dream job, we imagine a job in which we are fully ourselves, in which our hearts and minds are equally engaged.

This engagement is what people feel while vocationing. And once they reconnect with that deepest sense of self, few are willing to return to their status quo.

Which of course brings up the next question: what happens after the Testdrive? You go; you fall in love with a career; you leave fired up to work in your chosen field… and then what? Sure, you had a great couple of days; sure, you know what you want to do – but there is a gaping chasm between wanting and making it happen. And when you look down into that chasm it is brimming with house payments, car payments, college educations, health care, food bills, utility bills. How exactly do you take the next step?

The question is its own answer. You take the next STEP. The next small step. The biggest surprise for people who find or create their dream job is that it does not have to happen all at once. It does not have to be an all – or – nothing, hold – your – nose leap from security into the unknown. Instead, it can be a series of small steps that you take only as you feel ready. Sure, there are the few really bold (or independently wealthy) people who cut the ties to their previous careers and hurl themselves full time into new ones.

But most people take it more slowly. They continue at their current jobs while transitioning gradually into the dream. They do research, they write a business plan, they figure out how to begin the new career without taking on more risk than they can handle. Some go to school to get more training. Some dedicate a period of time to paying off debt and building savings so they will have funds for their new careers Some find work in the new field while they put together a business of their own. The path and the timeline vary from person to person; what they all have in common, though is the passion and the vision to move ahead

JUST DO IT 

Behavioral economists, who look at how people make choices, are well aware of the fact that we tend to choose the thing that feels most desirable in the present and postpone a harder or riskier choice until the future.

Fortunately, they have also noted ways that people work around that. One solution is to precommit, that is to take an action that requires you to make that more difficult choice now.

Precommitment is also an excellent strategy for circumventing fear. When you book a Vocation Vacationi now you can’t talk yourself out of it. You are precommiting yourself to something that felt scary. That way, when the time comes, if your brain’s limbic system urges you to put off the testdrive, you would no longer have the option.

Throughout this hero’s journey there are many ways you can precommit to circumvent your fear: schedule a Testdrive in Your Dreamjob three months in the future because that far away it won’t seem so scary.

Don’t commit if on every level you question the decision, but do commit if in your heart you know your course is right and it is only fear that is making you waffle.

FEAR 

If you are wishing for your dream job but are immobilized with fear, how can you go past that fear?

Let us take a moment to look at your nemesis, fear. When it comes to fear we are little better than rats. Brain research shows that we are wired to choose instant gratification over long – term gain. Much as we want our dream jobs, our brain’s circuitry pushes us to stay with the secure jobs we already have. In other words, now we want our steady paycheck, in the future we will risk pursuing the job of our dreams.

What causes us to favor the immediate over the long term? It is not simply impulsivity. It is caused by the interplay between our brain’s limbic and analytic systems. The limbic system, the seat of our feelings, controls our emotional response to situations. It functions a bit like an impatient child: strenuous, demanding and wanting immediate gratification. The analytic system, on the other hand, controls our thoughts, and more closely resembles an experienced lawyer, staying cool and rational even under stress. Whereas the limbic system places a premium on rewards in the present (it wants what it wants now) the analytic system values future rewards just as highly.

Apply this to leaving our current jobs and pursuing dream jobs and you can see how, in a sense, our brains are wired against us. Our analytic systems can do a stellar job acknowledging the long term benefits that come from working jobs we love, but our volatile, protect – me – now limbic system starts to hyperventilate at the idea of losing the secure job we have now. No wonder we have a hard time getting past our fear!

And as if our own physiology were not obstacle enough, there are plenty of other factors that encourage us to stay where we are. Money, family, loss of identity, fear of exposing the ‘ real you’ , the ‘fraud factor’ (that voice in our heads that says – you mean you think you can succeed at that??’) are all steely – gripped forces that work to keep us where we are.

But they don’t always keep us where we are. Despite the fact that everyone faces those hurdles, some people manage to surmount them and move forward toward their dreams. People with nothing in the bank quit their jobs and open successful businesses. Sole earners with families to support move cross country to work at starting wages in their career of choice. People who have spent years building respect and credentials in their profession chuck it all and go back to square one in another. And people who are terrified to expose the dream they have sheltered inside for decades manage to give up the career that was expected and take up the very different kind of work they love. How do they do it? What enables them to put aside their fear and take the risk?

Often when I describe The Hero’s Journey: Testdrive Your Dreamjob, the process of dream job seeking, people will say, ‘ Well I could not do that because I am not the right kind of person” as if there were a certain personality type that is capable of making the switch. I know what they mean. They have the idea that the type of person who can successfully pursue a dream job is someone who is exceptionally gutsy (or perhaps foolhardy) is very decisive and assertive; has a high tolerance for risk and ambiguity and has a history of creating opportunities and trying new things.

Kind of Hemingway type.

I suppose if I had not seen so many different types of people successfully create their dream jobs I would assume the same thing.  It is not so.  Successful creative heroes seem to come in all personality configurations. Some are so assertive they resemble bulldogs, while others seem so timid you wonder how they are able to ask water in a a restaurant. Some have a history of starting new ventures and others have worked entire careers in the same job. Some rattle off decisions with force, others deliberate until the last possible moment – and then change their minds!. Whatever you imagine the right personality type to be, I am sure I can find you a rolemodel who turns your stereotype on its head.

But that is not to say that successful dream job seekers don’t have anything in common. They do. The more people who make their money doing what they love I talk to, the more I see certain stories they tell themselves that most of them share. Regardless of their proclivity toward risk or their level of assertiveness, they have similar ways of telling stories about life and themselves that make it easier for them to proceed.

1.  A clear story. Successful creative heroes tend to have a clear image of what they want to to. It may be a particular job, it may be a type of work, it may be a lifestyle and a location. Though the level of specificity and detail varies with the creative professional what they share is a clear mental picture of themselves doing that kind of work. The clarity of the image acts like a magnet pulling them forwar. When they meet obstacles along the way, that magnetic image rallies them and keeps them moving toward it.
2.  Optimism. In addition to having a clear vision, successful creative heroes believe that their vision will pan out. Otherwise, they would not do it!. Some have a general confidence in their own abilities based on a history of success; others believe that this particular venture is primed to succeed. They know that failure is possible (and occasionally can’t stop that fear from creeping in) but most of the time they anticipate success as if that were the far more likely option.
3. Comfort with failure. When they do consider failure they don’t become terrified. Their attitude is ‘what is the worst that can happen?, whatever it is we will deal with it” They imagine a period of difficulty and adjustment after the failure, and then life moving forward positively once again.
4. A high self – standard. Over and over, in different words, I hear creative heroes express the same sentiment: I would rather try and fail than know I did not try.  I don’ t want to grow old and wonder ‘what if I had tried’? It is a recurring story: what pushes them past the fear is the knowledge that by not trying they will be letting themselves down.

Not everyone who makes the switch has everyone of these factor, but the people who successfully undertake dream careers seem to have most of them. Together, these attitudes make a package that seems to make it easier for people to move out of their comfort zone and try something new.

But even these attributes don’t fully explain why some people switch and others don’t. Something is still missing from the equation. And that missing something, I believe is urgency . People who make the switch have reached a point in their lives at which they simply have no choice. It is no longer a matter of wanting to make a change. They have to.

There is a moment when the pain of staying put outweighs the pain of making a change.

And that is a magic moment – because the moment we cross that line, things that previously felt like insurmountable fears begin to look more like manageable hurdles. Now on your way to work you find yourself dreaming up ways to overcome them.

Instead of wishing they were a way that you could move forward with the dream, you find yourself thinking about how you are going to do it. Instead of imagining some vague, open-ended timeline, you start fixing your actions to concrete dates when you know you will be able to act.

An enormous internal shift has taken place, and now even such major fears as money, family, identity and exposing the “real you” begin to lose their insurmountable quality. As if a locomotive has begun rolling inside you, from that moment on, you steadily gather momentum.

THE SEARCH FOR MENTORS

The Internet is the place to start your research into your dream job, but it’s not the place to start your research, but it’s not the place to finish. If you only the Web, you’ll end up with stacks and stacks of material and a decent theoretical knowledge of the industry but there will be a lot you won’t learn. You won’t learn much about the pragmatic, human side of the business. What are the people like who work in that field? What has their experience been? How is this career as a lifestyle? How much do they really spend and earn? How long did it really take them to be up and running.  Unfortunately, unless you’re incredibly gregarious and fearless, contacting real people is harder than just sitting in your house and scrolling, especially if you feel as if you are asking a favor. But meeting your rolemodels will give you a much more accurate picture of your dream field.

How do you contact complete strangers and tell them you want to learn about their field?

1.  Start by making a list of questions you want to ask them. You won’t get to ask all those questions in a single phone call, email or visit, but listing them will help you organize your thoughts.
2. Prioritize your questions. You want to ask your important questions first; you don’t know how long you’ll get to talk.
3. Go back to your research and pick out five or six people you’re going to contact. It doesn’t matter who or where they are; they can be people who are doing exactly what you want to do, or simply people who are knowledgeable about the industry and they can be in your own city or anywhere in the world. Ultimately you’ll reach out to many more; these are just to get you started. Having a target five or six will ensure that you don’t quit if the first one is unresponsive.
4. When you have contacted someone in your dream job, be sure to ask your contact who else you should talk to. Who else does he/she know who might be helpful to you.

You will be surprised at how fast the contacts and ideas build up. Each contact will lead to others and will suggest ideas you had not thought of, and soon your desk will be cluttered with notes and folders. It won’t be long before your questions become more targeted, and you find yourself actually enjoying the process.

How do you know when you’ve done enough research?  There is no hard-and-fast rule. Some people love researching and won’t stop ever. Others just want to jump in and get in action with their dream business. Both are fine. You will do more research after your testdrive. For now, the time to stop is when you know enough that you just can’t wait to move on to the next step, contacting potential mentors.

If you’re not getting to that point – if you reached ‘analysis paralysis’ and, despite information overload, are still resisting shopping for a mentor – perhaps there’s something else going on beyond a need for more data. It’s likely that you’re afraid. If that is the case go back to the step about ‘Fear’ and rewrite your story about it. Adressing that fear head on will probable free you to move forward.

Or it is possible that your resistance holds another message: maybe the career you’re researching is not your dream career after all. That can create its own form of paralysis. How can you walk away from that career after all the time and energy you’ve already invested? What will your friends, family and associates think after everything you have told them? And if that isn’t your dream career, what is? There’s comfort in knowing what we want to do with our lives, in sensing what the next chapter holds, and releasing that comfort can be scarier than never having a dream to begin with. No wonder we feel paralyzed if research shows us that our ‘dream career’ isn’t.

If that is the case, try to relax and accept it. Another dream will come – just as this one did – but it can’t come until you release the old one. In fact, having had this dream sets you up perfectly for finding the next one. You’ve already done the hard work of relinquishing the hold of the status quo. You had the courage to publicize a dream.  Who says the first dream has to be the ‘real’ dream? Dream job seeking is a process. It isn’t linear, it isn’t left brained. It is a circuitous path of back and forth, left and right, exploring options. The goal isn’t to do or become a certain thing; it’s to find out who  you are and what kind of work meshes with your deepest self.  If you’ve gotten to the point where you’ve had a dream and learned through research that it isn’t the proper fit, you have taken a giant leap in self – knowledge. You are primed to pursue your next idea. Relax and it will come.

QUESTIONS TO ASK 

Your research at this stage does not need to be exhaustive. You’ll be doing more research with your mentor and even more after your testdrive.  Right now you just want to get a basis education in your prospective field. Here are some things you’ll want to know:

Lifestyle

•  What is the typical lifestyle of people in this field?
•  Are there opportunities where I currently live or would I have to move?

Finances

• What kind of money do people tend to make in this field – initially and after several years?
• What kind of investment is necessary to get into the field?

Education

• What kind of education or training do people need to succeed in this field? Are there exceptions?

The Profession

• What are the current trends in the profession? Is it expanding? Shrinking? Saturated?
• Where are the new opportunities in the profession
• What are the biggest challenges facing people in this profession?
• What is the success rate of people in this profession to make money doing what they love?

This is just a starter batch of questions;  you’ll think of many more as you do your research. Later, when you work with a mentor you’ll get a chance to ask much more personal questions: “What has your experience been? How do you think this applies to me? After your testdrive you’ll focus on how to move into your dream career. But this is your chance to sit back and just immerse yourself in your dream. There is nothing you have to do right now except have fun learning.

You will be surprised at how fast the contacts and ideas build up. Each contact will lead to others and will suggest ideas you hadn’t thought of and soon your desk will be cluttered with notes and folders. It won’t be long before the phone calls become easy, your questions become more targeted, and you find yourself actually enjoying the process.

Friends of friends

In addition to talking to people you don’t know, you also need to talk to people you do know – and sometimes that is even harder. It can be challenging to tell people who have always known you in one identity that you are thinking of trying on another.

Part of what makes it scary to tell people you are thinking of trying something new is that it raises ‘exposure fear’:  What if they don’t approve? What if they laugh at me? What if they think I can’t succeed? But the fact is, until you talk about it, you won’t succeed! You need the info and contacts that come from talking, and you need the support that talking can bring.

Just as important, you need to hear yourself describe your vision over and over again – because each time you hear yourself say it, something magical happens: you believe a little more it will happen. The first time you say it, it sounds like fantasy – me a banker, becoming a movie director? By the twentieth time, though, with all you’ve learned, the vision will have evolved. Details will be added; the vision will be more concrete. With other people’s stories under your belt, you may even be imagining the bridge from here to there. What once sounded like a fantasy is starting to sound more like the beginning of a plan.

But until you start believing in that plan, it will never come to pass. At root, we are all a set of self – fulfilling prophecies: we accomplish what we believe we will accomplish in our lives and nothing more. So practice believing in your dream career. Talk it up in glowing, confident terms, because the more clearly and often you describe it, the more you enable yourself to make it real.

Of course, some people will be naysayers. It’s unavoidable. Some people just naturally leap to the negative, some will be jealous that you are making a switch that they themselves are or were afraid to make, some will always value ‘practicality’ over passion. That’s okay. Once you find out who your naysayers are, just don’t talk to them about your plan. If they bring it up, gently change the subject.

Fortunately, for every naysayer you will find multiple supporters: friends, family, colleagues and new people you meet will rally around to prompt you on. Some will root for you because they love you, some because they wish they could do such a courageous thing themselves, some because they can’t wait to become customers of your business! The support you get from the people you talk to can be so valuable that you won’t be able to proceed without it. Every creative professional who tells their story in the Hero’s Journey and Heroine’s Journey project has said the exact same thing — I could not have done this without the support of and then they mentioned names of family and friends who urged them on, who encouraged them when they felt down, who continued to believe in them and their vision all the way through the process.

WHEN IS ENOUGH ENOUGH?

How do you know when you have done enough research? There is no hard-and-fast rule. Some people love researching and won’t be satisfied until they have file cabinets full of paper. Others just want to jump in and get their hands dirty with a vocation. Both are fine. You’ll do more research after your vocation. For now, the time to stop is when you know enough that you just can’t wait to move on to the next step, contacting potential mentors.

If you’re not getting to that point – if you’ve reached ‘analysis paralysis’ and, despite information overload, are still resisting shopping for a mentor – perhaps there’s something else going on beyond a need for more data. It is likely that you’re afraid. If that is the case, read again my story about fear and have a dialogue with yourself: see if you can plumb the deepest source of your fear. Addressing that fear head-on will probably free you to move forward.

Or it is  possitble that your resistance holds another message, maybe the career you’re researching isn’t your dream career after all. That can create its own form of paralysis. How can you walk away from that career after all the time and energy you’ve already invested? What will your friends, family and associates think after everything you’ve told them? And if that isn’t your dream career, what is? There’s comfort in knowing what we want to do with our lives, in sensing what the next chapter holds, and releasing that comfort can be scarier than never having a dream to begin with. No wonder we feel paralyzed if research shows us that our ‘dream career’ isn’t.

If that is the case, try to relax and accept it. Another dream will come – just as did one did – but it can’t come until you release the old one. In fact, having had this dream sets you up perfectly for finding the next one. You’ve already done the hard word of relinquishing the hold of the status quo. You’ve had the courage to publicie a dream and ask for help. You’ve become proficient at doing research. Who says the first dream has to be the ‘real’ dream? Dreamjob seeking is a journey. It isn’t linear, it isn’t left-brained. It’s a circuitous path of back and forth, left and right, exploring options. The goal isn’t to do or becoma e certain thing: it’s to find out who you are and what kind of work meshes with your deepest self. If you have gotten to the point where you’ve had a dream and learned through research that it isn’t the proper fit, you have taken a giant leap in self-knowledge. You are primed to pursue your next data. Relax and it will come.

FINDING THE RIGHT MENTOR 

Why are busy working people so eager to help strangers enter their business? Why are they willing to take time away from their work? To disclose trade secrets? To train their own possible competition? They do it for a number of reasons?

•  They love what they do and they love sharing it with others (Don’t you get excited talking about the things you love – especially to people who also love them?)
•  They want to give back for all the help they received when they were getting started.
• They want to give to others what they didn’t get themselves, to spare others their own mistakes.
• They like the energy that a  passionate newcomer brings.
• They enjoy the act of teaching and the pride that comes from being asked for advice.
• They believe in their occupation and want to see the profession grow.
• They’re reminded that they have dream jobs themselves, and appreciate with fresh eyes how much they have learned and accomplished.

It’s not really surprising that people like mentoring. Despite the perception that we are naturally self-protective- especially in masters of work, money and survival – researchers have found that our brains are actually wired for cooperation. The act of helping someone triggers activity in the pleasure centers of the brain and literally makes us feel good. The findings led researchers to believe that helping behavior is hardwired into the brain. And indeed, this makes sense. Our earliest ancestors needed cooperation to hut big game, raise children, and gather far-flung plants. While competition was necessary to secure scarce resources for one’s group, cooperation would have been equally essential to survival.

MENTOR OF YOUR OWN

So – mentors are out there, ready to cooperate with you.  But how do you go about finding one? Well fortunately you have already done most of the work. All the research you’ve done to learn about your dream career has given you the names of organizations and businesses in your field, and evry one of them may be home to a mentor. The trick now is to figure out which of the potential mentors is right for you.  The process of selecting a mentor is really a mutual interview. The mentor checks you out to learn what you want and see if you’re someone he wants to take on, at the same time you are checking the mentor out to make sure he’s able to give you what you want. Here are some things to look for:

• Passion. First and foremost, look for people who are passionate about their work. As you visit people to interview them, look and listen for signs that they genuinely love their profession. Who wants to learn from someone who is bored and burned out?
• Expertise. Look for someone who is an expert in the profession. Perhaps you have already heard about someone with a great reputation. If not, once you narrow your search to one or two prospects, ask others in the field about them. How are they regarded?

• Teaching ability. Look for people who are good teachers. It’s not enough to be an expert in the field; your mentor needs to know how to transmit knowledge to you.
• Longevity. If possible, pick someone who has been working in the dream job for five years or more. By that time the mentor will have worked out most of the bugs in the job or business. Will have demonstrated staying power, and will have a longer – term perspective to pass on.
• Connection. Most important, pick someone with whom you ‘click’. You want to be able to ask all your questions, be entirely honest, share your fear and your excitement, feel comfortable, and have fun. In short, you want someone who makes you feel at home. If you have a choice between a more experienced mentor who is a little distant and a less experienced one who treats you like an old friend, go with the latter. You can always do a second vocation with the more experienced mentor later. Make your first one as comfortable and fun as possible.

MAKING CONTACT

The easy part is done – the research and reading, the making lists of possible mentors – and now you have to do it. You have to reach out and make the contact. The best way to start is not with a phone call, but by e-mail. Sending an e-mail will give your prospect a chance to digest the concept of mentorship without having to deliver an immediate response. It will also make your follow-up phone call much easier: the prospect will already know why you are calling.

YOUR INTRODUCTIONARY E-MAIL

Short, to the point, and respectful are the qualities that will help your e-mail get a response.

• Keep it brief: the less your prospect has to read, the more he’ll absorb.
• Be clear about what you’re asking: I’d like to spend a small amount of time learning at your side at a time that is convenient for you.
• Make it personal: say why you’ve chosen him above all others.
• Let your personality and passion shine through: show your prospect why he wants to work with you.

Here is one way an introductory e-mail might go:

Subject line: (your prospect’s name), will you be my mentor?

Dear (name),

For the last …………years I have been a ….., but at the age of …..,  I have decided that life is too short not to do what i really love, So I am thinking very seriously about moving into the field of………. Before I do, however, I would like to spend a couple of days ‘test-driving’….. as a career. I am writing you because (insert a phrase about why you admire this person and why you have chosen him as possible mentor) and I am hoping that you might be willing to mentor me, to let me come and work with you for a couple of days, at your convenience. I know that bringing a mentee into your business has its downside: even though I’m very eager to pitch in and do all I can, it won’t be like bringing in an experienced worker. But I can promise you that I am a fast learner and that I will be VERY appreciative of everything you have to teach me.

I hope the idea of mentoring someone who shares your passion for …. will spark your interest. if not, I will certainly understand

I will call you in two or three days to discuss this further. Or if it’s more convenient for you, please don’t hesitate to call me directly at …… Thank you so much for your attention!

Sincerely,

(your name and phone number)

PREPARING FOR YOUR PHONE CALL

Of course, you will follow up your e-mail in two or three days, just as you said you would, but before you do that, you have homework. You need to plan exactly what you will say. Planning ahead saves you the embarrassment of getting tongue-tied; it also prepares you to pursue the conversation in whatever direction it goes. The phone call may be very brief: the prospect may indicate clearly that he isn’t interested and say goodbye, or he may be so interested that he schedules a longer call or meeting. Or it may last half an hour or more as you ply each other with questions. You want to be prepared for all three outcomes.

Here are some things to think through before you pick up the phone. You might want to write down your questions and answers ahead of time, just to help you feel more secure.

Your greeting: Once your prospect answers the phone, you’ll have about thirty seconds to explain who you are and why you’re calling Fortunately, the hard work has already been done – by your e-mail. Now you just need a quick recap:

Hello, ….. This ……  I emailed you the other day about the possibility of having you mentor me. Right now I’m a ….. but I’m thinking seriously about going into the field of …… and I was hoping I might be able to spend a few days with you as your mentee.

Pause here and see if your prospect recalls the e-mail. He probably will: it’s not every day one gets asked to be a mentor. Even if he has no interest in mentoring, he’ll probably at least remember the invitation. You can also tell from his response whether he’s interested in the idea, opposed to it, or lukewarm, in which case you’ll have a chance to persuade him.

If, by some chance, he doesn’t remember your e-mail, give the two sentence synopsis you’ve practiced:

I’ve done a lot of research into ….. (or, I have a lot of experience in……..) but before I make a career switch I’d like to ‘test-drive’ the job for a few days so that I have a better sense of what it’s really like. I have a lot of respect for you and your work (borrow the sentence you used in your e-mail) and I was hoping I could come and spend a little bit of time with you as your mentee. I would do it completely at your convenience.

Your follow-up. Once the prospect understands who you are, he is apt to want more information. Be prepared to talk about the following things:

• How you see the mentorship working: how many days, how much time per day, what you would expect from him. Describe your best case scenario (for example three days, full-time) but also suggest other options (half days for one week, or two full days a week apart ….) Assure him that you understand how busy he is and that you are completely prepared to accommodate his schedule.
• Your level of experience in, or knowledge of, the field.
• How you found him.
• Why you think you want to move into that career.
• Exactly what you hope to get out of the mentorship.

Your questions. You will be interviewing the prospect as much as he is interviewing you and you need know if you and he are a match. To that end, here are things you should be prepared to ask:

• Do you love what you do (Just because the prospect is in your dream field doesn’t mean it’s his dream career, so check that out.
• What keeps you going? What is it that, every morning, gets you charged?
• Would you have time to spend with me if I came (or would you redirect me to someone else)?
• What kinds of things would you imagine us doing together?
• Will I be able to …….? (Fill in the blank with anything you particularly want to do or see)
• Are there other people on your staff with whom I could or should spend time?
• Have you ever done anything like this mentorship before?

Chances are, you won’t get through all these questions and answers in your first phone call, but going in prepared will increase the information you do get.

CALLING YOUR PROSPECTIVE MENTOR

Okay, you’ve done all the prep, you’re as ready as you’ll ever be to pick up the phone. So how come your fingers are still shaking? Because not only are you about to ask someone for an enormous favor, but you may have an aggrandized vision of the person you’re are about to call. After all that research and all that preparation, you may see him as the Obi-Wan Kenobi of your dream career – perfect, intimidating, larger than life. But he isn’t. He’s probably a lot more like you than you imagine. He’s probably close to you in age and, perhaps, in family obligations. He’s probably spent a similar number of years in his career. You’re probably as expert in your career as he is in his; if the tables were turned, he would be calling you. There are areas in which you possess greater experience and wisdom than he does. So before you pick up the phone, give yourself a pep talk. Think of your prospect as a peer, not a paragon. It will make your interaction easier.

When you do call, four things are apt to happen:

1. The person won’t be available and you’ll have to leave a message
2. You’ll get a clear “Not interested”
3. Your prospect will lean toward “no” because of the concept of mentoring raises concerns but he’ll be willing to hear more
4. You’ll strike gold: your prospect will get it.

Let’s take these situations one at a time.

If you have to leave a message. Say the same thing in your message that you had intented to say in your greeting. Just recap your email, leave your name and phone number, and state a number of times when the prospect can reach you. If you don’t hear back in two days, call again, and if need be, leave another similar message. If there’s still no response after your second message, let it go. This is not the mentor for you.

If your prospect says no. First you have to decide what kind of ‘no’ it is. Is it ‘No, I am completely unequivocally uninterested!? Or ‘No, probably not right now?” which may really be a disguised ‘yes’. If a prospect is completely uninterested, let it go. A reluctant mentor is not a mentor. You won’t have fun with, or learn much from, someone who isn’t enthusiastic about teaching. Put your energy into finding a better mentor elsewhere. But if the prospect says, Not right now, it’s possible that with more information you might persuade him. Take it to the next step.

If your prospect wavers. Here’s where you need to take a deep breath and dig down into the part of you that is really energized and passionate about pursuing your dream – because if any part of you can convince the prospect to help you, it’s that part.

First and foremost, you want to go for connection. If the prospect feels your passion, if he feels you are a kindred soul, if he sees in you his own early days in the field and remembers how much he could have used a mentor’s assistance, he will be more apt to extend an invitation. Try to spark that connection by describing your own enthusiasm for the field. Outline your experience, describe your long term vision, explain how the mentorship can help you move forward. If you connect on a personal level he will be more apt to say yes.

The prospect may also have very legitimate concerns about having you in his workplace. Mentoring you will take time out of his day. He may be concerned about having a novice underfoot. He may be reluctant to share propietary information or train potential competition. These concerns can be understandable deal breakers. Sometimes, however, prospective mentors and vocationers can work around them – especially if a warm, person-to-person connection has been made. Here are some ways to handle possible objections:

Objection: “I am too busy.”

Response:  I want a short term internship that works around your schedure – just a few days, or maybe just a few hours a week – whatever works for you

Objection: “I can’t train my competition”

Response. I am not planning to open my business in your area. I’d be happy to sign a non-compete agreement saying I won’t start a business within a certain distance”.

Objection: “It would cost me money to take the time to mentor you; I can’t afford to give away my time”

Response. “I understand that you will lose productivity with me there. I would be willing to pay you a fee to compensate you for your time”

Objection: “I can’t have a nonemployee on the premises; I don’t have adequate insurance”

Response: “I’d be happy to sign a liability release form if that would make you feel better and if would meet the needs of your insurance company”

Objection: “My business is confidential. I couldn’t take an outsider in”.

Response. “I’d be happy to sign a nondisclosure agreement if that would help. Or perhaps you could let me see aspects of the business that are not confidential.

Of course, even with your assurances, the prospect is still apt to refuse. That’s understandable: he’s spent years working his business; he is justified in being protective. So if after a bit of discussion he hasn’t started to agree, thank him for his time and let him go. You don’t want a mentor who had to be talked into taking you; you want one who is excited about showing you the ropes. And you will find him – elsewhere.

If your prospect says yes. Eventually, you will come to a prospect who says yes. Yes! But hold on: your work isn’t done. Now you need to figure out if this prospect is right for you. You want to get to know each other a little and see if you’ll actually like being together. You’ll want to ask the questions you prepared earlier about how the prospect sees the mentorship working, and make sure that your expectations are in sync. If the prospect is local, ask for a half-hour meeting. If he is long-distance, arrange for a fifteen-or-twenty-minute phone call. When you get together (whether by phone or in person), listen past the words to see if you can discern the following:

• Does this person exude passion for the work?
• Is he enthusiastic about mentoring?
• Does he seem like a good teacher (patient, interested in you, willing to share information readily)?
• Do you like the prospect? Do you feel comfortable?
• Do you feel energized when you leave the meeting?

If all these things check out, congratulations! You’ve probably found your mentor.

How long should the whole process of finding a mentor take? Unfortunately, there is no rule of thumb. It could take two hours or two months, depending on how many emails you send, how many phone calls you have to make, and just how lucky you are. Many vocationers I know found their mentors on the first try: they had spoken to them earlier while doing their research and established a relationship, so when the time came to ask for a mentorship the path was already paved. Others found that even when they cold-called, the mentors were either so impressed by the vocationer’s thorough process of preparing for career change, or so fascinated by the idea of test-driving a career, or so tickled to have been selected as a potential mentor, that they quickly agreed. Other vocationers found mentors quickly by pursuing a one-on-one relationship with a professional teacher, sometimes for a fee, sometimes for free.  One thing I have found in my own calls to mentors is that the prospects who say yes tend to do so quickly because they really understand the value of the mentor role. They have lanuched or found their own dream careers and know how important a mentor can be. So don’t spend a lot of time with a prospect who seems dubious or hesitant. Speed the process by moving on to the next person on your list. Your mentor is out there waiting to be discovered.

MULTIPLE MENTORS

Nowhere is it written that you have to have only one mentor. Once you’ve found your first mentor, and done your testdrive, you may decide there are things you’d like to learn or experience with someone else. A different mentor in the same profession can give you another perspective on the dream job or a chance to practice what you’ve just learned. A mentor in a related profession can give you experience that complements and extends what you’ve already done.

Most people go into their mentor relationships hoping for advice, encouragement, and maybe a few contacts, and sometimes they come away with more, long term business partnerships. Whether in formal working relationships or informal, ad hoc arrangements, dream job travellers and mentors often continue their relationships in ways that are mutually beneficial.

DOING THE TESTDRIVE 

Testdrivers of their Dreamjob commonly find that for days ahead of time, they are barely present at their current jobs; their heads are too full of what is to come. But this is exactly the time when you need to slow yourself down and take a deep breath. Your  Testdrive in your Dreamjob is going to be exhilarating, enlightening. challenging and fun … but it also needs to be instructive. You want to come away with an accurate picture of your dream and a clear idea of whether it is the career for you. That means you need to go into the Testdrive prepared. You have already done a lot of research and while searching a mentor you thought through what you hope to accomplish. Now it is time to fine-tune that thinking a little more. You don’t want to get home and realize that half your questions went unanswered.

WHAT IS MOST IMPORTANT?

Start by thinking seriously about what’s important to you. You’re pursuing a dream career because you want to live from your heart. What exactly does that entail? Does it mean working fewer hours? Or working closer at home? Does it mean making a difference in the world, or working with a particular population? Do you want to be indoors or outdoors? In the city or in the country?

What are the elements that HAVE to exist in your new career in order to make it your dream? Make a list of them – because after your testdrive you’ll compare what you have learned to what you said you really want. In your dream job euphoria, you may be inclined to overlook the fact that you said you wanted to work fewer hours yet your dream job requires round the clock attention. Stay grounded. You might decide later to forgo some of those ‘essentials’ but at least do it with your eyes wide open.

WHAT WILL HELP YOU DECIDE TO PURSUE THIS CAREER FURTHER?

Get out some paper and pencil and think concretely about what you need to leave your Testdrive in Your Dreamjob with. Your questions are likely to fall into the following categories:

• Skills: What skills do I need to learn or strengthen? Can I master them enough to truly succeed?
• Money: How much money does it cost to become qualified for my dream job or to set up my own business if that’s part of the dream? How much can I expect to earn initially and down the road?
• Time: How will I spend a typical day? How many hours will I have to work? Will that change with time? Will this job afford me the lifestyle I want?
• Technical issues: What do I need to know about equipment, purchasing, location, suppliers, processces, etcera?
• Pitfalls: What are the biggest hazards in this work?
• Career path: How can I break into the field? What can I expect my path and timeline to be?
• Family: How would pursuing this job affect my partner, kids, extended family?
• Support: What organizations provide ongoing support in this field?
• Contacts: Whom else should I talk to?

GET PERSONAL: GETTING THE MOST FROM YOUR MENTOR

The answers to your questions are going to come partly from living your dream job – seeing what you do and noticing how it feels – but they will come equally from talking with your mentor. You’ll get to learn from your mentor’s personal experience – and that experience may vary considerably from the more public information you’ve already received. Conventional wisdom may hold, for example, that you need a master’s degree to enter the field, but your mentor may tell you she has only a bachelor’s, as do others in the field. Though your research may have delineated a specific route up the career ladder, your mentor may tell you a backdoor path to the same destination. Industry Web sites may have suggested that the market in your industry is already saturated, but your mentor may know categorical or geographic niches that are not yet filled. Years of experience have brought your mentor several textbook’s worth of learning (including information she may not even know she knows). With a little forethought, you can access that data.

Your mentor may, in fact, have wisdom to offer beyond the job itself. Many people who do work they love (and probably most of those who choose to mentor) have actively chosen their careers. Many have made the switch from less satisfying jobs. They have stood in your shoes. They know the fears you’re facing, they have dealt with the financial insecurities, they know what’s involved in giving up the security of a ‘regular’ job and moving into something new, and most will be happy to discuss this aspect of the dream job switch as well. So don’t feel that you have to restrict your questions to the specifics of the job itself. Obviously, you need to respect your mentor’s privacy – you want to ask respectfully and watch for cues that you might be prying – but give your mentor a chance to discuss her full experience. You’re apt to learn important ‘off the record’ information, and you may deepen your relationship as well.

For the same reason, you also want to tell your mentor about your fears and concerns. Are you secretly terrified that you don’t have what it takes to make it in this field? Fess up. Speaking the fears out loud will disempower them. It will also give your mentor a chance to tell you how accurate – or inaccurate – they are. Are you embarrassed to admit that, even more than the mentorship itself, you’re nervous about traveling alone to another city? Say so. Your mentor will probably empathize and then give you detailed information that will make your trip easier. Are you nervous about simply being out of your comfort zone? No shame there: most people are nervous when they’re doing something new. Telling your mentor how you feel will help you relate to each other as person to person instead of simply as professional to student. It will strengthen your relationship before you even arrive at your mentor’s door.

BEFORE YOU GO: CONTACT WITH YOUR MENTOR

Help your mentor prepare for your Testdrive in your Dreamjob by providing him written information ahead of time. A list of your questions and concerns as well as background information, will enable him to make the best use of your time. (If you’ve offered him this information in your earlier phone conversations, ask if you should follow up in writing. It might help him to have it when he sits down to plan your visit). Remember: think of your mentor as a peer, not as someone on a pedestal. You are as knowledgeable about your field as he is about his; in another context, the tables could be turned. More than one Testdriver in your Dreamjob has found himself offering advice to his mentor from his own field of expertise.

Before your Testdrive in your Dreamjob send your mentor the following:

• your list of questions
• a list of anything you particularly want to do or see during your visit
• a list of your fears and concerns about the job and about making a transition
• your résumé or a short biographical statement
• a description of your experience and knowledge of the field
• a cover letter that goes something like this:

Dear (name),

Thank you so much for letting me come and learn at your side! Before I show up I thought I would send you a little bit of information. I’ve put together a list of questions I have about getting into ……  I know our time is limited and that we probably won’t be able to cover all of them, but it will give you an idea of the kinds of things I’m hoping to learn. I’m also enclosing a little of my background information so you have a sense of who I am and how much I already know about …

Again, thank you so much for hosting me. I can’t tell you how much I appreciate it.

Sincerely,

(your name)

QUESTIONS FOR THE MENTOR

Here are some of the things you’ll want to ask your mentor. Your own list will grow as you prepare for your visit.

Skills

• What skills do I need in order to succeed in this profession. Which do i need to learn or strengthen? Can I master them enough to truly succeed?
• You’ve talked to me and watched me work; do you think I’ll be able to p;erform this work well enough to succeed? (hard as it is, ask your mentor to be honest; there’s no point pumping time, energy and heart into something for which you’re not well suited).

Time

• How will I spend a typical day? How many hours will I have to work? Will that change with time? Will this job afford me the lifestyle that I want?
• How do you balance your work and nonwork life?

Money

• How much money does it cost to become qualified for my dream job or to set up my own business if that’s part of the dream? How much can I expect to earn initially and down the road?
• Do you have advice about getting a loan or working with bankers?
• What are the biggest expenses? The most unpredictable expenses? The hardest to control expenses?
• Which expenses can I defray and which are essential at start up?
• What can I expect to earn at first? Down the road?
• How long did it take you to break even? Earn a profit?
• What did you earn at first? What do you earn now?
• What were your biggest money mistakes?
• What has helped you maximize revenue and reduce expenses?
• Would you be willing to let me see your business plan? Your annual budget?

Technical Issues

• What do I need to know about equipment, purchasing, location, suppliers, processes, etc?
• What ongoing training do you recommend?
• Are there any mistakes you have made that I can learn from?

Marketing

• How do you attract customers? What works well? Less well?
• How do you determine prices?
• What were your biggest marketing mistakes?
• What was your biggest marketing success?

General

• What were your biggest surprises?
• What was your hardest time?
• What is hardest for you on an ongoing basis?
• What would you do differently if you were starting over?
• What is the biggest obstacle you think I’ll face?
• How would pursuing this job affect my spouse or partner? Our kids? Our extended family?
• What should I absolutely do?
• What should I absolutely not do?
• What else should I ask you?

Career Path

• How did you get into the profession?
• How can i break into the profession? What can I expect my path and timeline to be?

Next Steps

• What are the next steps I need to make to move forward?
• Do you have contacts who can help me?
• Are there other people you recommend I speak to?
• Are there organizations in this profession that I should join (or stay away from)

CHOOSE A CHEERLEADER

One of the most intimidating aspects of pursuing a dream career is the sense that you’re doing it all alone. Behind you is the security of the existing job and company, paycheck and lifestyle; in front of you is …. who knows?  You feel as if you’re standing at the edge of a cliff and all the people with safety nets are behind you.

Well, that isn’t really true. As you move forward through the process, numerous people will come forward to support you. You’ll find mentors who can help you learn the ins and outs of the business. As you pinpoint each new need you will find people to help you meet it, and those people will come to feel like trusted advisers. One day you’ll look around and realize that you’ve created an entire support network to guide you forward. You will not be doing it alone.

But that’s all in the future. For right now you need to choose one person – just one carefully selected person  – to be your main cheerleader. This person will be your primary support through the entire process – the person you lean on when things get tough, the person whose judgment you know you can trust, the person whose vision of your future will remain unclouded even when yours starts to blur. Your cheerleader will set deadlines for you when you procrastinate; she will remind you why you’re doing this when you start to waver, she will ask probing questions that help you see the forest as well as the trees.

In fact one of the biggest reasons to have a cheerleader is that that person will be able to see things that you are too close to see yourself.  You don’t need a professional coach to play that role. Nor do you need someone with knowledge of your dream field. What you need is someone who is a good, intuitive listener, who can be objective, and who genuinely cares about you. You need someone who will set aside time to meet with you periodically throughout your transition and who will see this as a ‘job’ that goes beyond the parameters of an ordinary relationship. You should think of it as a job, too, and when you choose someone to fill it, you should evaluate candidates in your mind just as if you were hiring someone for a paid position. Don’t consider just family and friends; go through your address book. Look for someone who has the right personality and skills.

When you’ve identified your candidate, describe the ‘job’ to her and ask if you can ‘hire’ her to do it. You won’t literally hire her or offer her money; you just want to let her know how seriously you take this, and that, by agreeing, she’s making a commitment.  Tell her why she was selected; ask if she’ll be able to give you time (perhaps monthly half hour conversations) over the next year. If it feels awkward or difficult to ask for this kind of attention, consider it from her point of view: she’ll probably be honored that you asked.

QUALITIES TO LOOK FOR IN A CHEERLEADER

When you ‘hire’ a cheerleader, pick someone who:

•  you can talk to openly and easily about your feelings;
•  has a positive, ‘can do’ attitude and will encourage you to  find ways past your hurdles, not become overwhelmed by them;
•  believes in you;
•  listens well and understands that this part of your relationship is strictly about you
•  is intuitive and can listen past your words to hear the deeper feelings and issues underneath
•  lives from both her head and heart; who can help you organize and pursue your action steps, but also understands the emotional importance of this change;
•  will not be afraid to challenge you when you get discouraged or when you lose your vision and focus; and
•  is not threatened by your determination to make a significant change.

Be careful on that last point. Your first inclination may be to pick a very close friend, family member, or spouse. But sometimes the people closest to us have the hardest time when we try to change, and peple who feel powerless to change themselves may resent our progress. Consider the impact of your change on the people you’re considering and pick someone who is able to be objective.

You may, actually want to pick two people. If it’s hard to find all those qualities in a single individual, split them up. Find one person you can talk with comfortably about the emotional aspects of your change (your fears, your hesitations, your moments of discouragement) and another who can help you with the ‘business’ side of the process.

Before you go on your testdrive, talk openly with your cheerleader:

• let her look over your list of questions. Brainstorm together to see if you can think of others.
• tell her your concerns. Her job is not to answer them but rather to validate them simply by listening.
• encourage her to ask you questions as you talk about your dreams. Her questions can help you clarify your thinking.

Talking to your cheerleader should energize you and build your confidence. It should feel safe, supportive and constructively challenging. If it doesn’t, go through your adress book again, ask associates for recommendations, and hire a different cheerleader.

SHOULD YOU HIRE A COACH?

Professional coaches specialize in helping people define and achieve their goals. If you’re considering a major career change, that kind of support can be very helpful. However, coaching is a relatively new career and certification is not yet required, as a result, people with varied backgrounds are free to call themselves coach. I have worked with excellent coaches, however, i met also coaches who would have been better in another line of work. So if you choose to work with a coach, be as diligent in researching, interviewing and confirming credentials as you would be with a mentor.

Before you hire a coach, consider the following:

• Select a coach who focuses on career coaching rather than life coaching. A good career coach will consider lifestyle; a life coach, however, may not focus on your career.
• Talk to references. Ask them if they actually made the changes they hoped to make.  You want to hire a coach who gets the job done, not one who is simply likable.
• Hire someone who has been in business full-time for at least five years. Since anyone can call himself a coach, you want someone who has verifiable experience.
• Interview several potential coaches so you have a base of comparison. You want someone who is passionate about coaching, has concretely helped people in situations similar to yours, and with whom you feel an emotional rapport.
• Consider a coach who is certified by a reputable coaching organization, but do not disqualify someone who isn’t. A coach with decades of pragmatic career coaching experience may not have chosen to get certified. More important than certification is meeting the criteria above.

BEFORE YOU GO

Before you head off to test that dream, make sure to have the following things printed out in your itinerary:

• the specific hours of your mentorship
• directions for getting there
• your mentor’s contact information, especially his cell phone number (make sure he has yours in advance, too)
• a rough agenda for how you’ll spend your time (subject to change as your mentor’s business requires)
• what you should (and should not) wear
• what you should bring

GETTING THERE

On your way to your Testdrive in your Dreamjob be flexible and plan ahead.

• If you’re traveling to your testdrive, arrive a day ahead so you can relax and review your questions the night before
• Get a good night’s sleep. Testdrive in dreamjobs are draining!  Between the newness, your eagerness to learn, your excitement, and your nerves, it will sap a lot of energy
• If you’re driving to your testdrive in your dreamjob, get good directions and leave extra time for getting lost. Better to spend ten minutes in the parking lot taking deep, meditative breaths than to find yourself hyperventilating because you’re running late. Don’t forget your mobile so you can call for directions if necessary.

WHEN YOU”RE THERE : LISTENING WITH YOUR HEART 

So far, you’ve given a lot of thought to the information you hope to get before you leave your testdrive. But information is only half the story. The other half is how your dream job feels. After all, the whole point of doing a testdrive is to get into work you love, so a huge part of the testdrive is testing out the heart side of the package. Do you love being there? Do you feel that this is the work you are meant to do? Does some inner part of you sing while you’re doing even the drudgiest part of the job.

That is what you need to monitor while you’re there. And then you need to use your imagination. You need to imagine that you’re doing those things every day – day in, day out – for years…. How does the job feel now? Talk honestly with your mentor about the ‘yucky’ sides of the job. Got a good handle on how much time she spends on tasks you would find distasteful. As how she deals with the parts of the job she doesn’t love – or even like – and how she maintains her passion regardless. Then think deeply and honestly about how you would fare in the same situation.

Ask your mentor to play devil’s advocate. Have her describe several common ‘nightmare’ situations and ask you what you would do in each. Encourage her to challenge your responses to make sure you see each situation in the most realistic light. Do you still think you want this job?

Also listen with your body. Sometimes our bodies know better than our heads what is right – or wrong – for us. Is the work physically comfortable? Can you handle it, day after day? And for years into the future? Talk with your mentor about how her body handles the demands.

DREAM JOB JOURNAL

Once you are on your testdrive, the information will come flying at you faster than you can imagine. You won’t remember half of it unless you write it down. Get yourself a small notebook that you can carry easily and maybe even slip into a pocket, and keep it with you every moment. Don’t be embarrassed to have your mentor watch you writing. She’ll feel honored that you take her words so seriously and she’ll know how serious you are about learning her business. You’ll have time for only cursory notes as the day unfolds, so in the evening go back and write a longer version while the material is still fresh. That way you’ll also see the gaps in your knowledge that you want to fill in before you leave.  The journal is also a good place to write down your questions before you go. That way, you’ll be less apt to leave the testdrive in your dreamjob with important questions unasked.

MENTOR RELATIONS

Your mentor has invited you to come because she’s eager to help you learn. Hopefully, she’s planned a schedule that gives you great exposure to the business. But as welcoming as she may be, if something urgent arises, her own business needs will take priority over chaperoning you. That means things may not always happen exactly the way you want. You may lose some time with her, or have limited access to parts of the business, or may find yourself wandering the building talking to other employees while your mentor tackles an unexpected problem. If this occurs, your job is to be gracious. Take advantage of the free time and use it to do one of the following:

• talk to other employees;
• closely observe various aspects of the business
• catch up on your note taking
• think of more questions to ask and
• imagine this was really your job: how would you feel coming here, doing these tasks, having these responsibilities, day after day?

Respect for your mentor’s time and schedule also extends to ‘after hours’. Some mentors are happy to use the evening to extend the internship, answering questions over dinner or attending a work-related event. Others prefer to limit their mentoring to the workday Be sensitive to the signals your mentor is sending out. If you sense that she’s open to it (and you are not depleted!), ask if you can take her out to dinner so you can continue to talk. But also understand if she wants to call it a day.

MAY I CALL YOU AGAIN?

So  you’ve hit it off with your mentor, you’ve learned more than you can possibly remember, you’re practically giddy with enthusiasm…. More than anything you want to continue the relationship. You want him to walk you step-by-step to your new career. Well, he can’t.  Much as he might like to, he has his own job to do. But that doesn’t mean that he doesn’t want to hear from you again.  If you’ve established a rapport and he’s sensed that you’re really serious about moving into the business, he probably does want to keep in touch and encourage you along. The question is: at what level? That’s something you need to ask.

Before you leave, tell your mentor how much you’ve learned and how much you appreciate his attention, and ask if he would mind if you contacted him again. If he says yes, establish some parameters. Calling every week and expecting him to guide your every decision is probably too much. (if he wanted to be a business consultant he would have gone into that line of work). But calling once a month and talking for fifteen or twenty minutes might just be fine. Perhaps he’s even open to repeating the mentorship after a period of time, or to doing something on an ongoing basis. Perhaps he’d consider a fee-for-serivce relationship in which you pay an hourly fee to work at his side. Or perhaps he’d take you on as an apprentice, accepting your service in exchange for the chance to learn. Think about what arrangement would work for you and propose it. The worst that can happen is he’ll say no; the best is you’ll get to continue working together.

WHEN YOU GET HOME

First, before you do anything else, send your mentor a heartfelt thank-you.  A note telling him how much the experience meant to you along with a bottle of wine, or a bouquet of flowers, or a gift certificate to a nice restaurant will mean a lot to the person who just gave up a portion of his workweek to help you.

Next, get out that dream job journal and review what you have written. This is your big chance to record everything you learned before it seeps away. So go over your notes, make sure they all make sense, and add any additional thoughts and learnings. Jot down the ideas for your own career that came to you while you were there. Write down any questions you still have. You’ll create many folders of data as you go forward in this process, but your journal will probably remain a bible, a source of info that you return to again and again.

Next, memorize what you’re feeling. Hopefully, you’ve come back from your vocation elated. Regardless of whether you pursue your dream career, simply spending time living the dream is enough to make people euphoric. It touches something deep, deep inside; some essential part of ourselves. That in itself is life changing. If you’ve returned from your vocation feeling this way, savor it. Let the feeling seep through every pore, because that feeling is the whole reason you did a vocation; that’s the feeling you want to replicate as you create the next phase of your life. Don’t make any rash decisions during this period; bliss is lovely but not necessarily conductive to clear thinking. Just enjoy your elation and wait until you touch back down before you start planning your next moves.

If you Testdrive in your Dreamjob wasn’t what you hoped for, if you return home disappointed, don’t despair You just gained a crucial piece of information! You learned not to pursue that career! Think of the time, unhappiness, and money you saved yourself by finding that out now. Regardless of which you may feel – elated, disappointed, or simply confused – celebrate. You did it! You dared to dream, you put the dream out there, you took a risk and test-drove your dream career. No matter how you felt about the Testdrive, you deserve major compliments. You have done what the majority of people are too afraid to do. Congratulations!

EVALUATING THE TESTDRIVE 

A week or so after your testdrive is the time to start doing serious evaluation. Your feet will be nearing the ground, your head will be clearer, you’ll be back in the real world, where you can make more calculated decisions. This is the time for asking yourself hard questions – and giving yourself honest answers.

The purpose of the evaluation is to determine if this is, indeed, your dream career. Perhaps you already know in your gut that it is or isn’t. Do a formal evaluation anyway. Asking yourself the targeted questions below will help you look closely and honestly at everything you learned and will give you important information for going forward.

The hardest thing about evaluating your vocation may be being brutally honest. By the time you’ve done your research, found a mentor, talked it up with friends and family and done your dreamjob, you’ve invested a lot of time, energy and hope in this career. Consciously or unconsciously, you’ve created a vision of your future, and a big part of you is now counting on that vision coming true. That creates a lot of pressure to bend the career to what you want it to be – or to bend yourself to fit the career. This is a great time to get your cheerleader involved. Her job can be to help you resist that pressure.

As you think through the questions, ask your cheerleader to discuss them with you. Encourage her to push you beyond your initial answers, to probe the feelings underneath. She may hear things in your replies that you don’t hear yourself and encourage you to be more honest than you might be on your own. If your cheerleader can’t talk through the questions with you, write down the answers. Writing enforces a mental discipline that may make you consider your feelings more carefully.

A WORD OF CAUTION

As you do your evaluation, focus solely on how you FELT about your dreamjob. DO NOT – i repeat – DO NOT – consider the impact on your family or your finances, or the steps required to realize your dream career. Unless you’re single and independently wealthy; pursuing a dreamjob is going to be fraught with family and financial implications, and there will be dozens of steps to take that seem all but impossible. Your ‘yeah, but’ voice will be all over that crying ‘You can’t do that! What about your family? What will you live on? But you don’t know the first thing about running a business? Those are excellent concerns. They need to be adressed. But they don’t need to be adressed right now.  They don’t need to get in the way of deciding if this is really the job for you. If this is the perfect job, you can work on finding a way past those hurdles;  if it’s not your dreamjob, there’s no point wasting energy on them now. So do yourself a favor; don’t sideline yourself before you even get started. Figure out how you felt about your dream job before you tackle the practical concerns, because often, when we really, truly want something, we find a way to make it happen.

Evaluating the Testdrive:  Ask Yourself….

•  What did I love about this dream job?
•  What surprised me the most during my testdrive? Does that change my feelings about the dream job?
•  What did I not like about this dream job?
•  What did I not like about this dream job?
•  Do I find myself thinking, if only X were not part of the package…? Is X so problematic that it reduces my desire or ability to do the dream job?
• Can I do this dream job day in, day out?
•  What parts of the dream job are apt to get ‘old’ after six months or a year? How will I feel about the job then?
• How does this dream job match up with my list of ‘essentials’.  If I sacrified essentials to pursue this dream job, would the sacrifice be permanent or temporary? Is the trade-off worth it?

The 4 C’s

When considering a new career, you weigh the ‘4 C’s’: cause, community, capacities and considerations.

1. Cause: To be satisfying, a career must provide a sense of cause, or meaning
2. Community: You must enjoy the community of people you work with
3. Capacities: It must enable you to express all parts of yourself and to use your core capacities
4. Considerations: It must meet your needs in other areas, such as pay, commute, and schedule

Rather than evaluating these qualities strictly with your head, consider them from four distinct points of view: your rational self, your emotional self, your deep self and your body. We talk more about those four viewpoints later in this seminar.

NOT YOUR DREAMJOB AFTER ALL?

It is possible that your dream job was everything you’d hoped it would be.  Start formulating an action plan to turn it into a career. But what if you found that your dreamjob wasn’t as dreamy as you’d expected? Perhaps there were too many aspects of the job that you found unappealing. Perhaps the rigors of the job preclude the balance you want in your life. Perhaps you found that you don’t want to own your own business after all, or you want to dabble in that area but not turn it into a career.

That is fine! That is all good news. It was precisely to get that kind of feedback that you went on your testdrive. The point was to learn those things now, risk free, before you invested years and money in a career you didn’t love. Your goal, remember, was not necessarily to make this job your career, but rather to make yourself happy, to find work that serves your heart. Your testdrive has taken you a long way down that path. You learned how to research a career and find a mentor; you examined your values and lifestyle and determined what you want in a new career; you proved that you can stay true to yourself in evaluating future prospects. Most important, you’ve opened the door to change. This was not your dream career – but now you’re a lot closer than you were before.

Acknowledging that your dreamjob wasn’t your dream can be painful though. Not only is it disappointing, but it opens up a troubling question: Now What? If this isn’t my dream career, what is? One of the pleasures of pinpointing and researching a dreamcareer is that it gives you the beginning of a vision for your future. As long as you hold that vision you feel reassured; this is where I am heading; this is what I want to do; this is who I am. When that vision crumbles, that reassurance disappears. You find yourself looking into a hole where you once saw solid ground.

If you find yourself facing that hole, you may be tempted to continue pursuing the career you have been focused on rather than admit that it isn’t right. But that would be penny wise and pound foolish. You began this process in order to make yourself happier and more fulfilled. Don’t detour from that long term goal because of discomfort at this moment. You’ve already taken one of the hardest steps – overcoming the inertia of the status quo. You hatched a dream and made concrete progress toward it. Everything you’ve learned in investigating this career will help you find the one that is your dream.

CONSIDER A RELATED CAREER

Before you completely write off this career, however, consider another option: perhaps there is a related career that suits you better, a career that has many of the elements you do want and lacks some of the ones you don’t. So ask your mentor or others familiar with that field if they can recommend related jobs that may work better for your needs.

KNOW THYSELF

Sometimes the best thing that comes out of a testdrive is not a new career but a new perspective on the old one.  The greatest value of doing a testdrive is not the transition to a dream career, it is the insight you gain about yourself. Even people who never move to their dream careers find that the testdrive sparks a remarkable amount of growth and change. Simply going through the process requires you to assess your life, take stock of what’s important and create a vision for the life you want. It forces you to break out of your mold, meet new people, and learn new things. It gives you a chance to watch yourself in an unfamiliar setting, seeing how you respond and how others respond to you. It provides you a mentor and a cheerleader whose insight and honesty help you see things you might not otherwise see. The process of testdriving helps you reconnect with your deepest self, that place where dreams are kept, so that you can choose to live in a more whole way. So whether you decide to pursue the career you had a testdrive in, or a different career, or make no career change, at all, consider your testdrive a success. You will have given yourself an experience that has the potential to change your life.

WHAT DO I TELL MY BOSS?

One of the benefits of Testdrive your Dreamjob is that you get to try out a new job without telling your boss. As far as she and your coworkers know, you’re simply going on vacation. Even if they know exactly where you’re going and find it a little odd (‘you’re using your vacation to visit a bakery’) there’s nothing odd about having a passion for baking. Just tell them the truth: you want to immerse yourself in an area you love. They don’t need to know that you’re thinking of switching careers.

MOVING FORWARD

And where are you now? Are you more motivated than ever to pursue that dream career? Or did you come away with reservations? Having done the testdrive and evaluation, do you have a clear sense of what you want to do, or do you feel as if you’ve taken the long route back to square one and you’re still wondering what your dream career might be? If that is the case, it is time to research other careers. Keep in mind that researching other careers doesn’t mean you’re going backward. Finding a dream career is an incremental process. It may take two or three testdrives to figure out what job is right for you. Each one will show you more of what you want and don’t want and take you closer to your goal. If the idea of doing multiple testdrives is daunting, relax. The first one was hard because you were learning as you went along. Future research and mentor visits will be easier. If you’ve decided that you do want to pursue the job you test-drove, then turn the page. It’s time to plan your path to get there.

YOUR ACTION PLAN

Whether they are starting their own businesses or moving toward jobs in a different field , most people make a gradual transition as they work their way past the numerous constraints that stand in the way. Family obligations must be accommodated, debts must be repaid, money must be earned and set aside, classes must be taken…. Pursuing a dream job is less a leap than a series of incremental steps that move you closer and closer to your goal. What is critical to reaching the goal is making sure that the steps you’re following are the right ones. That means having an action plan: a clearly defined and timelined road map that will get you from here to there.

YOUR ACTION PLAN: START WITH A LIST OF QUESTIONS

Regardless of whether you plan on working for someone else or opening your own business, if you make a list of all the things you need to learn and know in order to make your dream job real, you will have mapped out a plan for moving forward.

Your questions will probably fall into several broad categories:

• Knowledge: things you need to learn in order to move forward
• Money: how you’ll finance your new career, and how you’ll support yourself and your family while you make the transition
• Timeline: over what period of time you’ll transition to the new career
• Family: how to make your new career mesh with the needs and wishes of your family

Right now, all those questions may seem overwhelming, but that’s because you’re looking at them as a group. When you take them on one by one they become much more manageable.

I have listed some of the questions you may have. You will, no doubt, think of more questions of your own. You don’t need to tackle all the questions at once. Many people prefer to tackle the money-related questions first: without having a financial game plan,  it’s hard for them to take the rest of the planning seriously. Others find it hard to plan their financing when they haven’t yet figured out what their educational needs are, what their timeline will be, and how their family will be integrated in the plan. You may find yourself working in all those areas at once since each area will inform the others.

For starters, go down the chart and pick the ones that speak to you – the ones that seem the easiest, or most pressing, or most interesting. Pick only a few at a time so you don’t feel overwhelmed and work on them at your own rate. For each one you pick, set a timeline – and then ask your cheerleader to keep you on track. Your timeline doesn’t have to be hard and fast, but without one you’re much less apt to get the project done. Remember: you’re the boss here. You set the goals and timeline. This is your dream you’re realizing; even at this stage it can be fun.

Knowledge:  What do you need to learn to move forward with your dream?

Questions to ask yourself:

• What skills or information do I need? How will I learn them?
• Do I need certification or a degree or can I get by without it?

If you are planning on opening your own company

• How do I start a business?
• How can I finance a business?
• How do I write a business plan?
• How do I hire, pay and retain employees?
• What do I need to know about managing employees?
• What do I need to know about managing the books?
• Are there government requirements?
• Are there legal issues?

If you are planning on working for someone else

• How sound is the business?
• Are the owners reputable?
• What is the benefits and compensatioin package?
• Do I need to learn more about my new field? (competitors, size of market, geographic variations, trade organizations, latest technology, trends, legal and regulatory issues
• How will people respond to my business?
• How can I make it more attractive?
• What will people pay for my products and services?

Questions to Ask Yourself if you are looking at Taking a Job in an Organization

• What is my salary likely to be?
• At what rate will it rise?
• If I take a pay cut, how will I manage my finances?
• Will I have additional expenses (e.g. school, commuting, travel supplies)

Questions to Ask yourself if you are starting a business

• What will my start-up costs be?
• What will my ongoing costs be?
• How long before it becomes profitable?
• Where can I find financing?
• How much of my own money will I have to invest?

Questions to Ask yourself If you are thinking of Going to School

• How much will it cost?
• Can I go part-time in order to keep working?
• Can I get a student loan without first cashing out my savings?
• Will I have to pay off debt first?
• Can I reduce my expenses?

TIMELINE : How and when will you transition to your new career?

Questions to Ask Yourself if you are waiting for a certain event

• Do I really have to wait, or am I choosing to wait because I am scared?
• Is there anything I can do to speed up the timeline?
• If I really have to wait, what can I do in the meantime to prepare? (get necessary education, do more testdrives, volunteer or work parttime in the new field, make contacts, research, make a business plan, make a transition plan in order to hit the ground running when the time comes, start your new career on the side)

DOES YOUR VISION MATCH THE MARKET?

If you’re planning to start your own business, one element of your business plan will be a market analysis: are enough customers willing to pay enough money for your product or service to make your business profitable? That can be a hard thing to determine, especially if you’re starting an out-of-the-ordinary business. It may be impossible to find sales figures to use as a reference. In that case, you need to be as open-minded as possible. Don’t assume that everyone will love your product or service just because you do. Talk to people familiar with the industry and with people in your target market and try to gauge objectively if the market will support your business. It’s a lot easier and cheaper to change your business model before you start than after you’re suffering losses! If research suggests that the business isn’t viable, get creative. How can you tweak the business and make it responsive to the market while still maintaining your passion?

FAMILY

Being single has its advantages. One of them is that you’re often able to make plans without considering other people’s needs. But for many of us, that isn’t the case. We have spouses and/or family members whose needs matter enormously, and we can’t just decide to run away and join our personal circus. A part of our strategy, therefore, has to be working with our loved ones to get the opportunities we feel we need. Every successful vocationer will tell you that switching to your dream career is far easier, and your chance of success is far greater, if you have your family’s support.

Unfortunately, that support is rarely automatic. Even the most encouraging spouse is apt to have reservations – simply because pursuing a career switch can be so disruptive. Finances, children, the partner’s job, the extended family may all feel the impact, and while you float around on your cloud of optimism, you leave your spouse or partner no choice but to remain planted firmly in the earth: someone has to think about the mortgage, the children, the in-laws, and day-to-day-life. The challenge is to find a way that you can have your opportunity while your partner’s needs are also supported. The key is open, honest communication. Here are some tips:

• Listen openly to your spouse’s concerns, fears and objections. No knee-jerking reaction allowed! If something your partner says triggers you, take a time-out, go cool off, think about why you reacted so strongly, and then come back and finish the discussion. Getting angry or accusatory will not help your cause.
• Take your partner’s concerns seriously. They are valid – even if you disagree. Discuss them with people who have knowledge in that area (not just friends who will agree with you). Be open to what the experts say
• Adress the fear. Recognize that your spouse’s objections may stem from fear. Empathize with that fear. Find concrete ways to address it.
• Compromise. There are many ways to reach every goal – even yours! You can compromise and still get where you want to go. Do you need to keep your job longer than you want to? Start your new career in small ways on the side. Do you have to wait until your youngest child is out of school before you switch? Do all your research and planning now. Be creative as you consider your options and you’ll find ways to keep your new career on track.
• Establish clear parameters for compromise. If you do compromise, make sure the extent and limits of the compromise are clear. For example, if you agree that you can start your dream career immediately but that you’ll go back to your old career if it does not pan out, make sure the turnaround point is measurable. Name the date on which you will decide, or the financial threshold you will have to meet, or another tangible target you will have achieved, in order to continue with the dream.
• Don’t overpromise. No matter how confident you are in your ability to succeed, don’t downplay the risks or overstate the rewards. When the inevitable setbacks occur your partner will feel misled, angry, and distinctly less supportive.
• Get help. If you have trouble talking with your spouse about these issues – if tempers flare each time you have a conversation, or you revisit the same arguments over and over again without making progress – see a counselor. These are big, life shaping issues you are facing. Both partners need to feel heard and honored, and both need to be happy with the outcome.

Negotiating your desire to move toward your dream career may not be easy – but it has a tremendous upside. It presents an opportunity for your relationship to grow – partly because it forces you to listen carefully and respectfully to each other, and partly because it gives you a chance to connect on the deepest level. You have done a lot of soul-searching in the process of researching your dream career and doing your test-drive. You have probably learned a lot about yourself in the process. Now is a chance for your spouse to do the same. With encouragement, spouses, too, can examine their dreams, needs, and desires, as well as the things that have kept them from realizing those dreams. Talking about those things together can help you grow in closeness, understanding and respect. You may not reach absolute agreement on everything; after all, you are different people and want different things. But, ideally, you can reach a place in which you can say honestly to each other, ‘I disagree with you on this, but I respect you and I will support your decision.”

If you cannot reach that point – if discussing your dreams broadens rather than shrinks the space between you -there may be underlying issues in your relationship that need to be addressed.  Consult a counselor. Professionals can often help you work through issues taht you can’t tackle successfully on your own. It’s important to address those issues before you proceed with your dream because unresolved, they are apt to undermine you down the road.

AGING WITH 20/20 VISION

Many people have long held that holding up a vision of what we want increases our chances of achieving it. Now rigorous research studies are showing that, at least in certain respects, that is true. The studies in question have to do with people’s vision of aging, but they have bearing on how – or whether – we realize our dreams.

Becca Levy, a psychologist at Yale, is one of several reseachers who are testing the effect of beliefs about aging on the health and vitality of elders. Their tests are showing that people who hold a positive vision of aging are apt to be healthier and less frail than those who subscribe to the negative stereotypes about older people being frail. In one study, after testing the memories of ninety healthy older people, Dr. Levy flashed positive words such as wise, alert, sage and learned on a screen. Then she tested the subjects again. This time their memories were better than they had been the first thime and their walking speed had increased.  When she flashed negative words on the screen – dementia, decline, senile, confused and others – and then tested the subjects again, their memories worsened and their walking speeds slowed.

Thomas Hess, a psychology professor at North Carolina State University, saw similar results in his own studies. He found that when older people were told something negative about aging (for example that aging causes memory loss) they subsequently performed worse on memory tests than they had in their initial screening. If they were first told something positive about aging (for example, there is little decline in memory with age) they performed significantly better.

In a separate study to examine the long-term effects of positive and negative visions of aging, Becca Levy analyzed the results of the Ohio Longitudinal Study of Aging and Retirement, a twodecade study of 1157 people age fifty and older. In addition to health information, the study had included beliefs about aging, and Dr. Levy found that people who had more positive views about aging were healthier than those with negative views, and lived 7.6 years longer. They also had less hearing loss three years into the study than they had had when the study first began. These results persisted even when Dr. Levy accounted for participants’ health at the start of the study as well as their age, gender and socioeconomic status.

If maintaining a positive story about aging can have a measurable impact on our health and lifespan, can envisioning ourselves in our dream jobs have an impact on our careers? That research hasn’t yet been done, but the implication for dream job seekers seems clear: create a story of your new career and hold it dear because our stories do, indeed, shape our behavior.

MEETING THE FAMILY’S NEEDS WHILE ALSO MEETING YOUR OWN

Inevitably when one person in a family makes a significant change, that change reverberates throughout the family. Working with your partner, anticipate the changes your career transition will bring and plan solutions.

Here are some of the issues you are likely to face. It is not exhaustive but it will give you ideas for getting started.

How will your career transition affect your family?

Questions to Ask Yourself

Money

Wil I be earning less money? Will I need to spend a lot of money? What will that mean for our family? Can we reduce our expenses? Can we supplement our income in some way? How much of our savings, home equity, and/or retirement can/should we use.

Possible solutions. To reduce financial impact.

– Keep existing job longer and start new job or school on the side. – Take a parttime job while starting new career or school. – Work extra shifts or a second job for a period of time to save addditional money before switching

Possible actions: Make a multi-year budget showing how you will meet all expenses during transition. Agree tot tentative timeline for transitioning in stages, as finances permit. Agree to an earning swap with your partner in which he agrees to earn more money now in exchange for you doing so later. – Slow your transition time-line while you stockpile money – pay off debts