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Learning to Fail · May 7, 2026

The Fork in the Road

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Aaron Dinin · Learning to Fail

Last week at Duke, the school hosted an event called “Blue Devil Days.” It’s when the university invites all the admitted high schoolers to campus while they’re figuring out which college to attend.

Because these students are struggling with a tricky decision, and because more than a few of them recognize me as “that Duke professor from social media who likes giving unsolicited advice,” when they’ve seen me around campus, they’ve been stopping me to ask: “How do I know which school to choose?”

While I obviously have my biases about the best university, I try not to let that bias control my response. Instead, I’ve been taking the opportunity to help them see what kind of question they’re really asking.

Specifically, whether they realize it or not, the challenge they’re facing isn’t a “how do I choose the right college” issue. It’s more of a “life” issue that we all face at various points in time. And the decisions never get easier unless we learn to approach them the right way.

I remember facing a similar type of choice back when I was deciding where to go for my PhD, I was wavering between SMU in Dallas and the University of Maryland, and even though I ultimately chose Maryland, I occasionally find myself wondering about the version of my life that might have come from going to Texas.

When I think about that version, it doesn’t feel like a worse life. It just feels like a different one.

Different city…

Different colleagues…

Different opportunities…

When I follow that thread far enough, I start imagining a world with a different wife, different kids… basically… different everything. In other words, the entire foundation of my life that currently exists basically wouldn’t have happened because of one decision.

No wonder these types of life-altering choices we all encounter from time to time can feel so stressful. They’re clearly bigger than “normal” choices.

I like to think of these bigger decisions as “fork in the road” moments. They’re the decisions where the stakes feel high, the options feel meaningful, and — most importantly — you feel like your future hinges on picking correctly. A fork in the road moment is basically choosing between two completely different worlds.

Every time I spoke with students about their college choices this past week, I tried helping them see how they were framing the decision the wrong way. They kept imagining they were supposed to be choosing the “right” school, but that’s not how fork in the road moments work. The options in front of you aren’t competing versions of the same life. They’re entirely different lives. And, as we all know, lives aren’t simply “good” or “bad.” They’re infinitely complex.

As a result, when we frame the biggest choices in life as “Which option is right?” we’re pretending the future is something we can predict and optimize as if there’s a version of our life already waiting for us at the end of each path, and our job is simply to pick the one that’s going to get us there.

But that’s not how life works. Our futures don’t exist yet. They’re waiting to be built, which means the biggest choices we make also create the most responsibility.

This increased responsibility is the part that makes fork in the road moments so important to understand properly. Once you realize a “right” answer doesn’t exist, you avoid thinking one option is going to result in “success” and the other will end in “failure.” Instead, you gain ownership over the outcome.

A fork in the road decision sets a direction, but you shape the outcome based on the effort you put in, the relationships you build, the opportunities you choose to pursue, and every other choice that follows… big and small.

In other words, the future you’re trying so hard to predict isn’t waiting for you at the end of the path. It’s something you’re going to create along the way. And while knowing all of that won’t necessarily make these types of difficult decisions feel less important, making them will hopefully feel less stressful because you’ll know the outcome isn’t predetermined. You can finally stop searching for a perfect answer and start focusing on what you’re going to do once you’ve made the choice.

A helpful reframing for those moments where failure feels possible.The next time you find yourself confronting a fork in the road moment, step number one is to stop asking yourself, “Which option is right?” That question makes the decision feel like a lottery ticket, which is creating lots of the stress. The best way to avoid this stress is by reframing the choice, which you can do by asking yourself some of the following questions:

  • Which path am I most curious to explore?

  • Which set of tradeoffs am I more willing to accept?

  • Which environment feels like it will challenge me in a way I want to grow?

  • If there’s no perfect answer, which choice feels most worth committing to?

  • Which option feels more aligned with the kind of person I want to become?

  • Where do I feel a sense of energy or pull, even if I can’t fully explain why?

  • If both options were going to be hard in different ways, which kind of “hard” would I rather take on?

  • Which path would I regret not exploring, even if it doesn’t work out?

  • Where am I most likely to take action instead of waiting for things to happen?

  • Which option gives me more opportunities to create something, rather than just consume what’s given?

These questions won’t remove the uncertainty. But don’t worry… that’s not the goal. The goal is to shift your focus away from trying to predict the future and toward choosing a direction you’re willing to invest in.

Reflecting on our experiences is where the most important learning happens.Once you’ve made a difficult, complex, fork in the road kind of choice and lived with it for a bit, the questions will naturally start to change. Obviously, you can’t reset the decision. But you also don’t need to. After all, at that point, the decision itself matters a lot less than what you’re doing with it. So instead of asking whether you picked the “right” path, try asking:

  • What have I done so far to make this the right choice?

  • Where have I been fully engaged, and where have I been holding back?

  • What opportunities have I taken advantage of... and which ones have I ignored?

  • Have I been building this path, or quietly second-guessing it?

  • What has surprised me about this experience so far?

  • What parts of this decision have been better than I expected? Worse?

  • Where have I been waiting for things to happen instead of creating them?

  • What relationships, habits, or routines am I building that will shape where this path leads?

  • If I fully committed to this path starting today, what would I do differently?

  • What would it look like to take more ownership over the outcome from here?

Remember, these questions aren’t about judging whether you made a good or bad decision. The decision was made, you can’t change it, and you can never know how the other choice(s) would have worked out.

Instead, now that you’re here, it’s time to recognize you’ve chosen a direction, so it’s time to focus on the outcome. That outcome is going to be shaped by your actions, so focus all of your attention and energy on those.

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