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Learning to Dream Big for Your Intentional Career

Welcome to the latest installment of my series on creating an intentional career! We’ve already done a lot so far. In the first week, we reviewed what it means to create an intentional career and why it might be important for you. Then, we looked at how and why you can discover the core feelings in your heart that can guide you toward your intentional career. Then, I explained how time tracking is a critical part of discovering what your intentional career might be. Most recently, we looked at how and why clearing space is important to draw more intention into your life.

The last two weeks, we started part one of something I think is so critical to creating an intentional career: discovering your core values and creating a list of five core values.

In today’s post, we’ll be taking an oft-ignored step in creating a career, because it sometimes seems too fanciful: learning how to dream as it relates to our career.

This is something I love to talk about and am ardently passionate about: relearning our ability to dream, which I firmly believe is a divine right we are born with, but is often conditioned out of us by the time we exit childhood — much to our detriment.

This week’s assignment has three parts and should take no more than a few hours.

Before I describe the assignments, though, I want to talk about dreaming and why I believe it to be such an important part of an intentional career.

I believe that dreaming, imagination, and envisioning beautiful, big, bright and sometimes wacky or audacious-seeming things is a skill we are born with, and instead of being nurtured, is conditioned out of us starting at a very early age.

Most societies today worship at the alter of logic, practicality, feasibility, and security. If we have big, bold crazy dreams as children, some of the first words we’ll hear when we say those dreams out loud is, “That’s never going to happen.” “You can’t do that.” “That’s nice, but it would be too hard for this or that reason.” “It’s more important that you get a job that earns you a lot of money and prestige.”

Sound familiar? We learn to acquiesce in order to get acceptance from our caretakers and society, and before we know it, we too have become quite skilled at being sensible and safe — but we have forgotten how to allow ourselves to dream, especially in the arena of our careers. In fact, in many of us, the reversal of dreaming skills turns into a form of perfectionism. We won’t dare dream about something we are not “good” at, because we have become so concerned about success and getting everything right at first crack.

Yet dreaming is an enormous part of living an intentional career. This became so clear to me when I once saw a tweet (I cannot find the original sadly) that said something along the lines of, “You were put on this earth to do more than try to lose weight and earn money.”


But if we are out of touch with our ability to dream, if that dormant muscle hasn’t been stretched in decades, we may simply think that we do not have dreams, and substitute our dreams with what activities or goals seem logical or practical to spend our lives doing.

I assure you: you have dreams.

And today are going to get you back in touch with them.

This week’s assignment is three parts:

  • A journaling assignment
  • Writing a letter to your current self from your future self
  • And finally, drawing an image of your future self

Let’s dive in.

#1: Journaling assignment: This exercise is adapted from the workbook I reference and use constantly, The Artist’s Way. This book was instrumental for me in my ability to learn to move past perfectionism and dream again. The journal exercise from here is quite simple. Make sure you have at least 30-45 quiet minutes uninterrupted. I’d like you to settle into a comfortable position. Take several deep belly breaths, and relax your body. Then, begin writing, using this prompt: “In my career, I would like to ________.”

These phrases can be as simple as “I would like to mentor somebody” to as far-fetched as “I would like to travel to Antarctica for my job” to everything in between. In fact, they may start out more simply: “I would like to clean up my cubicle” and end up somewhere in the realm of, “I would like to be on a presidential committee” or “I would like to become a New York Times bestselling author.” All of these from start to finish are encouraged.

I want you to write 100 of these lines. Yes, 100.

I ask you to do so many because at least the first dozen, if not the first half, are likely to be eminently practical or “realistic.”

But as we move into the realm of writing these repeatedly, we will get more stream of conscious, and lose a bit of that practical thinking, which is the goal.

By the 100th one, you may not even want to stop. That’s fine. Keep on going. Write as many or as long as you want to.

But do at least 100.

Then, review your list. Star the top 10 that jump out at you of your “In my career, I would like to…..”s. What themes may these 10 share? Are any of them something you could do today or make a step towards? Why do they feel so relevant? Ponder these for a while and take action on any that you would like. Or not — that’s fine too. But do choose your top 10.

#2: At some point in the week after the “I would like to exercise,” write a letter from your future self five years from now, to you as you are right now. Write this letter from the vantage point of you have achieved everything dear, important and inspiring to you in your job. Where are you writing from? What have you achieved? What is the most important message you want your current self to know? What lessons have you learned? What advice do you have? What goals are you dreaming up now, five years from now? Let this letter range as wide and far as you like; there are no parameters or “right” way to do this letter. Just truly imagine yourself in a dream scenario five years from now and let loose. Simply start it along the lines, “Dear [your name], it’s me, five years from now. I have some things I’d like to share with you about your career…”

#3: Draw your future self as they are in your dream job or career. Now, this exercise is likely to provoke some rampant perfectionism or anxiety in you. “I’m not good at drawing!” you may cry. That does not matter for this exercise. Nobody else is going to see this. And we’re doing this for a few reasons: It’s fun. I swear. Drawing is one of those things that if we’re not immediately skilled at, we’re not encouraged to keep doing in our lives. Pshaw. It’s fun. Two, drawing triggers subconscious parts of our mind that allow us to integrate more intellectual wishes and realizations with deeper inner knowing. Drawing your future self will bring that self closer to reality by the way it will activate your brain. (Science.) In fact, studies show people are more likely to complete their goals if they draw it — even if they don’t consider themselves visual learners or artistically inclined. So, in order to draw our future self, our intentional self, closer to us, let’s draw them.

This doesn’t have to be fancy. You can do it with a pen, pencil, whatever, on any piece of paper. Or you can go all out with colored pencils or crayons or watercolors. Whatever you like.

So stop for a moment, close your eyes, and think of yourself five years from now. What are you doing? What are you wearing? What does your hair look like, and where are you? Who are you surrounded by? Are you carrying a bag, a book, are you cooking, traveling or gardening? Are you in a big corner office, or out in the field helping others? You can also draw abstractly; perhaps you envision yourself as surrounded by happiness in your future career; you could simply draw a smiley face to represent that. It’s okay to get conceptual in this, too, but also ground it in what you hope and dream you might really be doing.

And that’s it for this week. As usual, I would love to hear from you. What surprised you from the “I would like to…” exercise? What were your top 10? In your letter or drawing, what came up for your future self?

Catherine Andrews is an author, teacher, coach and expert in intentional living who works with clients to mindfully and authentically design a life that reflects all of their potential, dreams, desires and capabilities. She is the author and host of The Sunday Soother, a newsletterpodcast and community dedicated to authentic living and compassionate personal growth. She lives in Washington, D.C., and holds a bachelor’s in English Literature from the University of Virginia and a Masters in Journalism from Northwestern University. Before becoming a teacher and coach, she spent nearly 20 years in communications and journalism, and she still believes the stories we tell about ourselves and others are our greatest assets. You can find her on Instagram here.

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