Carte Blanche

I never liked playing the game of “If you could do it all over, what would you do?” The reality is we can’t do it all over again. We can, however, take action in the present, which is where our focus should be.

Then someone challenged my thinking. I was asked a series of questions by someone whom I think highly of and who tends to think deeply about life. He asked me to indulge him in the exercise, and I relented.

What if you could go back to school? Where would you go? What would you major in? If you could have chosen to live somewhere else, where would it be? Why? If you could change your career in a snap of the fingers, what would you do? If you could take a sabbatical year from your life, how would you spend the time?

It may be either impractical or entirely unfeasible to do these things, yet the exercise may have utility. You graduated college twenty years ago, and going back to another school probably isn’t going to happen. Yet maybe you can learn something from the latent desire. Do you crave a certain social experience that you never had? Is it a particular geography that appeals to you? Did you really want to study philosophy, yet you majored in economics?

Sometimes life’s delays aren’t life’s denials.

Giving yourself the latitude to think expansively can help you find creative solutions that work within the existing framework of your life. Perhaps you would have traveled the world for a year if you could go back and do it all over again. There are ways to better integrate travel into your life that allow you to manage your other obligations. Maybe a degree in philosophy isn't in the cards, but a class—or at least a book—on philosophy may be in order. You might not be inclined to change careers to become a professional athlete, but perhaps you can join a club baseball team.

Sometimes we lament the road not taken without realizing that past decisions do not wipe out our future possibilities. We can’t revisit every fork in the road or retread every path—that’s just a reality. But we can get creative and simulate some of those roads.

I’ve discovered a lot of deferred joys and elevated them to feasible options in my life. I never took that year aboard, yet my yearning to do so influenced my global travels. I would have loved to have been a writer. Acknowledging this passion has inspired ways for me to integrate writing into my life. While I aspired to be a professor, like my father, when I was younger, my career trajectory veered in another direction. Yet reflecting on that aspiration enabled me to find ways to be substantively involved in academia within the context of my current profession.

Even if you don’t take action, it’s useful to reflect on the decisions you have made and the opportunities you deferred. It gives you an appreciation for how many diversions and divergences there are in your journey—and how each choice might lead down a different path. Yet these paths often converge, and you may find yourself at a similar crossroads in the future. If you don’t reflect on your paths and contemplate the impact of your decisions, then you may not be able to make optimal choices in the future.

Beyond looking to the past, you can think about the divergences in the road to the future. Take some time to imagine yourself going down one path and observe what that feels like. Then imagine going down the other fork in the road and imagine what adventures may be waiting for you on that path. Don’t just let your analytical self make the decision, pour your whole being into the simulation, just like you would for a divergence in the past. Try to embody your choices before making them. Pre-live them. The mind is a time machine that can scurry back to meaningful times in the past and simulate times far in the future. It’s not perfect. But it is you. It is your mind projecting itself forward in time and immersing you in a potential situation before committing yourself to it. This can be an amazing tool for making decisions and future commitments.

I’ve now come around and become fond of “what if” questions. When they get too absurd or silly, I balk. But when they provide the opportunity to reflect on past decisions or ponder choices in the future, they can be powerful. Your mind constructs its own realities, sometimes in parallel with other people’s conceptions of realities, so leveraging that talent to try out fresh ideas and see what feels right can lead to better choices in the future.

Take some time and give yourself carte blanche to think about what could have been and what still can be. You’ll be better off for it.

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The Apprenticeship Mindset

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Choose Happiness—Pursue Fulfillment