Choose a Cheer Leader

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.

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.

Your Travel Guide


Story teller Peter de Kuster is the founder of The Heroine’s Journey en The Hero’s Journey and an accomplished speaker worldwide. His books and stories about the Hero’s Journey – making money doing what you love – have reached millions of creative professionals worldwide in the last decennium.

Read on for a detailed breakdown of The Hero’s Journey in Paris – Testdrive Your Dreamjob

What Can I Expect?

Here’s an outline of The Hero’s Journey in Paris – Testdrive Your Dreamjob.