Imagining Your Future Selves

Photo by Sindre Stru00f8m on

In his 2019 book Range: Why Generalists Triumph in a Specialized World, journalist David Epstein turns our perceived wisdom about careers on its head. Despite the common belief that to be successful one must commit to a path early and devote as much time and energy as possible to honing one’s craft, Epstein shows that those who find their path late, dabble in multiple fields along the way, and juggle many interests at once often find more professional success than their more focused peers. Epstein’s argument really resonated with our students, many of whom began their current career path back in high school (or even earlier), and who have internalized the belief that to explore other career options suggests a lack of focus, seriousness, or direction (and that lacking these things is somehow bad).

A central premise of Life Design is that each of us have multiple possible futures – that in some alternate dimension there is a version of me pursuing a life as an attorney in New York, a high school teacher in Oakland, and a coffee shop owner in the Hudson Valley. Rather than ignore these possible “future versions of us” in favor of the story we currently tell, Life Design encourages us to explore these future selves for inspiration and insights.

I created this series of exercises to help you figure out what these future selves might be, not so that you can develop a series of comprehensive 10-year plans to achieve them, but rather so that you can find people living your future life now. Or as Epstein would say, so that you can “be a flirt with your possible selves.” (163)

Dysfunctional Belief

“There’s one perfect life waiting for me in the future. I just have to figure out what it is and develop a plan to attain it.”


“I have many future selves, each with its own unique possibilities and attributes. To figure out who I want to become, I can prototype these future selves now and begin building my way towards the future.”

Step 1: List all the possible careers you have imagined for yourself

For this first step, write down as many careers as you can recall imagining for yourself over the years. This can include everything from your childhood dream to be the next LeBron James to the career path you are currently pursuing, and everything in between. The goal is to mine your memory for as many imagined careers as you can, deferring judgment along the way. If you have trouble getting started, you might consider the following prompts:

  • The career path you are on now
  • What careers you have considered if that path was no longer an option
  • As a kid, what you imagined you would be “when you grew up”
  • What your family wanted to be “when you grew up”
  • What you told an admissions officer you wanted to do after college
  • What you tell recruiters and interviewers now
  • What you have imagined doing if you won the lottery
  • What you would do if it weren’t for peer or familial pressure
  • The jobs you have heard about recently from friends or on social media and thought, “wow, that job sounds kind of cool”

Hopefully, you found this process easy, and even fun. Even the most career-focused individuals often daydream of different careers and lives, although they may never act on these imaginings. But by writing them down, we bring them out into the open and force ourselves to at least acknowledge that the career we are currently pursuing is not the only career we have contemplated for ourself.

Step 2: Review your list

Now that these careers are out in the open, take the time to consider each of them one-by-one. As you go through your list, ask yourself:

  • Which careers are you still pursuing or contemplating?
  • Which careers have you left behind (childhood dreams, dropped majors, etc.) but would like to reconsider?
  • Which careers delight you? Intrigue you? Inspire you?
  • Which careers are you not exploring out of concern for your family or due to peer pressure?
  • Which careers are you not pursuing because of dysfunctional beliefs?

As you contemplate this list, think about which careers you want to explore further. Very often we get so focused on the “safe” career path in front of us that we never allow ourselves the opportunity to explore unconventional or delightful paths out of fear of failure or because we have been told – or have told ourselves – that these paths won’t make us successful.

Step 3: Select three careers to imagine 10 years into the future

Now select three careers that you want to imagine yourself in 10 years into the future. You can include the career path you are on now and even your “plan B” but try to include at least one “wild” or “unconventional” idea. Whatever criteria you chose, these careers should be as different from each other as possible. Exploring possible future careers as a neurosurgeon, a cardiac surgeon, and a pulmonologist won’t allow for enough variation for this activity to yield any dividends. But a neurosurgeon, a pharmaceutical researcher, and an international aid worker? Now that will allow you to stretch your imagination and really explore your possibilities.

For each of the three careers ask yourself, “what might my life look like in 10 years if I pursue a career as X?”

Step 4: Imagining your future selves

Now the fun part. On three separate sheets of paper (one for each career), imagine what your life might look like in ten years if you were to pursue that career path. Don’t just focus on the job, but really try to flesh out each life as if you were developing a character for a movie. Feel free to incorporate drawings, images, memes, even sounds/songs – whatever gets your creativity going and really allows you to inhabit these imagined lives. Go broad! Don’t let your inhibitions hold you back. Rather than rejecting seemingly wild ideas out of hand, embrace them.

You should allow yourself to go where your creativity and imagination take you. But if you get stuck, consider the following questions:

  • Are you working at a specific company? Do you have a specific title or set of job responsibilities?
  • Where do you live? Work?
  • What about family? Do you have a partner/spouse? Kids?
  • What do you do outside of work? Hobbies? Interests? Volunteer work?
  • Which activities from college do you continue to pursue? Which have you left behind?
  • What is your most significant accomplishment in this life to date?

Once you are done, give each imagined life a 4-6 word title and write it at the top of the page.

Had I done this exercise as a rising senior at Cal, my Imagined Life #1 would have looked something like this.

Step 5: Reflecting on Coherency

Having imagined three different lives 10 years into the future, you now want to review them for coherency. Hopefully you have already completed your Compass (Workview and Lifeview/Worldview), and have kept a Good Time Journal for a few weeks to build awareness of which activities engage or energize you. Using these documents, assess how each of the lives you have imagined aligned with your own values and person True North. Some questions to consider might be:

  • In what ways do your imagined lives align with or support the values you articulated in your Workview and Worldview?
  • What specific aspects of your imagined lives – if any – are not in alignment with your Worldview and Workview?
  • Are there easy changes you can make to bring these aspects of your imagined lives into alignment? Are their conflicts that are more difficult to square with your values?
  • Are there aspects of these lives that include activities in which you experience energy, engagement, or Flow?
  • Are there aspects of these lives that now give you pause?
  • Does reflecting on your imagined lives make you want to revise or reconsider your Workview or Worldview?

(NOTE: If it’s been awhile since you’ve written your Workview or Worldview or done the Good Time Journal activity, I recommend repeating the exercise. For many people, COVID-19 has altered their view of work and the world, led them to discover new activities that engage them or give them energy, and allowed them to view their daily lives in a whole new context.)

Step 6: Tell the story of your imagined lives

Too often we keep our imaginings to ourselves, out of fear that if we share them with others we will be judged or made to feel silly. As a result, we never even allow ourselves to take the first step in exploring our possibilities, and instead stick with our public story that we know will earn us nods of approval from friends, family, and social connections. But don’t hide your lives in a drawer or immediately throw them away. Share them with your friends and peers who are also going through the Life Design process. Or even better, assemble your Virtual Ideation Team and share your lives with them.

Regardless of who you share your lives with, it is important to be upfront that this is not an invitation for criticism or advice, however well-meaning. But rather it’s an opportunity to hear your imagined lives reflected back to you by people who are familiar with you and your journey. When I teach this activity to my students, I ask those doing the listening to share their responses to the following:

  • When did your partner seem the most authentic? Was there a particular life or an aspect of a particular life that really seemed to align with who they are as an individual?
  • What are 2 things from each life that you can affirm (“I liked it when…”)?
  • What is 1 thing from each life that you want to know more about (“Tell me more…”).

The goal of imagining these future lives is not so that we can figure out which life will make us happier or more fulfilled and then develop plans to implement whichever one(s) we favor. In fact, our imaginations – as well as our memories – are a poor tool for determining out future emotional state. As psychologist Daniel Gilbert notes in Stumbling on Happiness, “instead of remembering our past experience in order to simulate our future experience, perhaps we should simply ask other people to introspect on their inner states. Perhaps we should give up on remembering and imagining entirely and use other people as surrogates for our future selves.” (246)

Indeed, the entire purpose of this exercise is to help you identify individuals living your future lives in the present. If you imagined a life as a software engineer at a tech startup in Toronto, then start working your networks to find someone in their early 30s living that life now and ask her for an informational interview. Use this opportunity not to gain Google-able information or to ask for a roadmap, but rather to conduct a Life Design Interview and “Try on Someone Else’s Life” in order to prototype your way to a fulfilling career.

“When people are deprived of the information that imagination requires and are thus forced to use others as surrogates, they make remarkably accurate predictions about their future feelings, which suggests that the best way to predict our feelings tomorrow is to see how others are feeling today.”

Daniel Gilbert, Stumbling On Happiness, p. 251

I’ll write about the best ways to address these Life Design Interviews in future posts. In the meantime, I encourage you to check out my colleague Smiti Nathan’s blog, Life Design Log. Smiti has been creating amazing lessons on using Design Thinking to frame questions (“DEFINE”) and using ethnography to create effective interview questions.

Happy Imaginings!

Life Design Images (c) 2017 Bill Burnett, Dave Evans and Stanford University

The exercises in this activity build upon the Odyssey Plans in Designing Your Life by Dave Burnett and Bill Evans. I’ve written earlier about the problems with Odyssey Plans and why they haven’t worked as well for our students. This set of exercises – by forgoing the plan in favor of imagining a life 10 in the future, well after the conclusion of graduate study, etc, to allow students to immediately connect with alumni surrogates – seems to work better for our particular context.

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