Picking the Right Path
And what to do when every option feels both promising and precarious.
This post is for anyone who feels pulled toward change but immediately second-guesses their instincts.
People seek executive coaching when they feel a strong sense that something needs to change. A new role, a side project, a sabbatical, a shift from corporate employment into something entrepreneurial. The conversation can also just start abstractly - a feeling that the current setup just isn’t quite right.
When I meet people at this point, they’ve located a real pull toward change. But that pull is almost always met by an equally strong voice of second-guessing. The instinct to partner with a coach feels like reaching out for help, but it’s also a way to manage risk.
That’s where things get sticky. Because even once the pull is acknowledged, and the intention to explore something new is spoken, the next step can feel impossibly weighted. Do I make the leap or not? Is this a smart move or a self-indulgent one? What if I’m wrong? It doesn’t seem to matter whether the change is dramatic or incremental. The anxiety shows up either way.
It’s the fear that choosing “wrong” will cost something permanent: momentum, money, focus, credibility. That by going down one path, you might lose the chance to pursue another. That by showing interest in something, you’re obligating yourself to see it all the way through.
No wonder people get stuck.
A Modern Kind of Paralysis
This stuckness is fed by the systems we live in - platforms that sense your curiosity and treat it as a data signal to exploit. The moment you express interest in a new direction, even passively, you’re met with a cascade of offers: tools, courses, consultants, templates. The promise is always the same: that the path you’re considering can be yours in days, with hardly any effort, if you just buy, sign up, click here.
Before you’ve even committed to a direction, you’re being pushed to accelerate it. You click a link about freelancing? Suddenly the internet wants to sell you a full suite of services to monetize your business, optimize your funnel, and build your personal brand. You mention a coaching idea? Prepare for ads promising six-figure months and passive income in 90 days.
The noise is overwhelming and it mimics urgency. It preys on the part of you that already feels unsteady. You’re still trying to decide if this new path is even the right one, and suddenly you’re also deciding whether to buy someone else’s map to get there.
For many people, this creates a new kind of paralysis, not from a lack of input, but from too much. You started by considering one big decision, and now the world is firing dozens more at you and urging you to move quickly. No wonder the whole process feels fragile. You’re trying to choose a direction while being constantly told you’re already behind.
It’s Not the Decision, It’s the Prediction
When people say they feel stuck, what they often mean is: I don’t know which path will work out best. But underneath that is a more impossible wish that some version of the future could be confirmed in advance. That if you think hard enough, gather enough input, talk to the right people, or read one more book, the answer will reveal itself.
But most real choices, especially the meaningful ones, don’t offer that kind of certainty. You can’t test-drive both futures. You won’t get to know what would have happened if you had chosen differently. And that’s what makes the pressure so intense. The stress of the decision is as much about sidestepping regret as it is about making a smart choice in the first place.
It’s a reasonable and responsible mindset that, in practice, leads to overthinking, delaying, and eventually disengaging. You get caught in a loop of analysis because you care deeply and want to avoid wasting time, money, energy, reputation. You want to bet on the version of yourself who wins.
So the challenge isn’t just about choosing. It’s about loosening your grip on the idea that you can predict what matters most from the outside. Sometimes, the only way to know is to begin.
Present-moment Choosing
The psychologist Ellen Langer has written compellingly about this. Her research on mindful choosing reframes the decision-making process away from outcome obsession. Instead of asking “What’s the best choice?” she invites us to ask, “What’s a meaningful choice right now?” As she puts it:
“Rather than struggle to make the right decision, what we should do is make the decision right, whatever the decision is.” (source)
It’s a simple and freeing approach.
Because the truth is, we almost never get to know what would have happened if we had chosen differently. There’s no alternate timeline we get to peek into. So evaluating decisions in hindsight - was that the right call? - is mostly a form of self-torture. The better question is: did I make a choice that felt clear, grounded, and worthwhile at the time? If yes, then the decision was good. Even if the outcome wasn’t.
Langer’s approach gives you permission to move without demanding certainty. To make the best call available in this moment and let that be enough.
Prototype, Don’t Predict
Another helpful lens comes from the Designing Your Life framework developed at Stanford. Built on the principles of design thinking, it offers a simple but powerful reframe: treat big life decisions as prototypes. Don’t try to pick the perfect path. Try something small and learn from it. (source)
Instead of asking, “What’s the best option?” the question becomes, “What’s a low-stakes way to explore this direction?” That might mean a side project, a single conversation, a class, a shadowing opportunity, or simply devoting time to the idea in a deliberate and structured way.
As the creators of Designing Your Life put it: “What would it be like if I tried this possible future in some small and easy-to-execute way?” The goal isn’t to succeed immediately. It’s to gather information not from abstract analysis (or crystal ball gazing) but from direct experience. To let action replace overthinking.
This approach pairs naturally with Ellen Langer’s view of decision-making. If the value of a decision isn’t fixed at the moment you make it, then what matters is how you move with it. A prototype invites you to engage mindfully, stay responsive to what you’re learning, and adjust along the way. You get to revise without losing momentum.
And you lower the cost of being wrong. Because you’re not betting everything on one choice. You’re collecting signals, following energy, and letting clarity emerge through doing.
Movement Over Mastery
There’s nothing wrong with wanting to make a thoughtful, well-informed choice. But the pressure to make the perfect one, to somehow choose the path that minimizes all risk, maximizes all outcomes, and justifies itself in hindsight, is not only impossible. It’s paralyzing.
And the systems around us don’t make it easier. They flood us with urgency, amplify comparison, and suggest that if you just had the right method or mindset, the future would feel obvious. But what actually builds momentum is movement.
You choose something small. You learn something real. You notice how it feels. And then you decide again, better informed.
The process may feel nonlinear and open-ended. But over time, it builds the kind of self-trust that comes from doing as opposed to imagining.
So if you’re in the fog of too many choices, take one small step toward what feels most alive. Don’t wait to be sure. Wait to be curious.
👋🏻 I'm an executive coach who works with mid- and late-career professionals navigating (or instigating) change like career shifts, leadership challenges, or questions about what’s next.
If you're in that place and want support that’s clear, grounded, and strategic, hit reply and let’s talk.