Week 22, 2025 - Fork in the road

Song of the week:

Top of mind

I've been thinking about forks in the road lately. Not the literal ones you encounter driving through the countryside (though those can be equally perplexing), but the career crossroads that inevitably appear when you're least expecting them. You know the ones: stick with the familiar path you've been on, or veer off into uncharted territory that might lead somewhere brilliant—or nowhere at all.

Last week, I had coffee chats with no less than four folks who are wrestling with this dilemma. They've been in $company for years, working their way up through progressively senior roles. Great salary, solid reputation, etc. The slog of weekly, monthly and quarterly reviews is hitting hard. The company has hired a bunch of execs from one or two specific companies, which alters the culture quite dramatically. And steers it away from what it was a few years ago and the promise of, back then, what it would be.

The Psychology of Staying Put

The sunk cost fallacy is our tendency to continue a behaviour or endeavour because of previously invested resources (time, money, effort, or emotional energy), even when giving up would clearly be the better choice. It's the reason we finish terrible movies because we've already watched half of them, stay in jobs that drain our souls because we've "invested too much to leave now," or persist with degrees that no longer interest us because we're already three years in.

The human brain, for all its remarkable capabilities, is surprisingly bad at separating past investments from future decisions. Research in vocational psychology shows that career decision-making involves comparing relevant alternatives, evaluating them, and arriving at an acceptable outcome—but this process is often clouded by our emotional attachment to previous choices.

Studies reveal that the more we've already "invested," the less likely we are to shift gears and walk away. It's as if our brains have evolved to punish us for changing course, even when that course is leading us straight off a cliff.

The Fear of the Road Not Taken

Robert Frost captured something profound in "The Road Not Taken." I suspect most people misremember the poem's actual message. It's not a celebration of nonconformity—it's about the stories we tell ourselves after we've made our choices. The speaker admits he'll probably claim "I took the one less traveled by, / And that has made all the difference," even though both paths were "really about the same."

The fear isn't really about making the wrong choice. It's about living with the uncertainty of never knowing what might have been. The hardest choices are the ones where both alternatives are attractive; selecting one means forfeiting the other.

But here's what I've learned watching friends navigate these crossroads over the years: the fear of regret often keeps us in situations that guarantee a different kind of regret—the slow-burning regret of never trying. Or worse, the FOMO impact. On my own journey, some friends from a past company who've I stayed closed to are shifting to a smaller business with all of the upside and promise that I joined $current for. It makes sense for me to chat to them, but sunken cost fallacy bumps into the road not taken aggressively. Nothing's abjectly wrong with me or my colleagues' current situations. In fact, by all accounts, it's incredible. But... what if?

Let's be honest—career changes aren't just philosophical exercises. They involve mortgages, health insurance, family obligations, and all the other beautiful complications of adult life. I'm not suggesting everyone should quit their job tomorrow to become a travel blogger (though if that's your thing, more power to you).

But I am suggesting that staying in a career solely because you've already invested time in it is a form of self-sabotage. Sometimes it's necessary to take one step backward to take two steps forward. The resources you've invested in your current path aren't just sunk costs—they're also transferable skills, experiences, and knowledge that can serve you in unexpected ways. In $prev_company, I stayed two, maybe even three, years too long. I had a boss who was obviously phoning it in and only wanted me and my team because I had a good reputation and he could appear to build a small empire on my shoulder. I knew this, but stuck around. When I handed my notice in, very senior folks were shocked because I never signalled unhappiness.

That's where my four colleagues and I today fall. None of us are vocal about the discontent because really, objectively, everything is amazing. But I think everyone acknowledges that the next few years will twist and shape into something that we didn't sign up for. And we're all about four to five years in tenure. It's probably time anyway, right?

Here's the thing about forks in the road: sometimes either path can ultimately lead you to where you truly want to go. But only if you have the courage to actually choose one and start walking.

Photo of the week

(via my unsplash)

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Published on: 31st May, 2025

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