Feeling Lost in Your Career? Stop Asking What to Do. Ask What to Avoid.
Being lost isn't the problem. Staying lost because you're too busy running away from the feeling, that's the problem. Slow down. The answer is usually closer than you think.
Most career advice tells you what to do. Build this skill. Network more. Find your purpose. It’s well-meaning and almost entirely useless when you’re feeling genuinely lost.
Here’s a more honest approach: instead of asking “what should I do?”, ask “what should I stop doing?” That one flip changes everything.
The inversion framework and why it works
Charlie Munger, the late Berkshire Hathaway vice chairman, had a principle he borrowed from the mathematician Carl Jacobi: invert, always invert. The idea is simple. When you can’t figure out how to succeed at something, map out all the ways to fail at it instead. Then avoid those things rigorously.
It sounds obvious. It’s surprisingly hard to actually do, because our instinct when we’re lost is to seek more options, not fewer. We want a roadmap. We want someone to tell us the answer. But more options, more information, and more advice often just compound the paralysis.
What actually helps is getting clear on what you’re willing to rule out.
A McKinsey research note on decision quality found that the biggest drag on good decision-making isn’t lack of information. It’s the emotional state people are in when they make decisions. Which brings us to the list.
The behaviours that keep you stuck
When you’re feeling lost, certain habits feel like they’re helping. They’re not. Here are the ones worth watching for:
Making emotional decisions. When you feel lost, there’s a pressure that sets in, the sense that time is running out and you need to act now. That urgency is almost always false. Most decisions have more time than they feel like they do. If you need more time to think, take it.
Blaming external circumstances. The economy, your manager, the industry, your timing. Blame feels useful because it locates the problem somewhere you can’t reach. But if the problem is out there, so is the solution, and that means you’re stuck waiting. The moment you stop blaming is the moment you actually have some leverage.
Numbing the discomfort. Binge watching. Mindless scrolling. Impulse spending. These don’t resolve the feeling of being lost, they just postpone it. And they tend to compound the problem because you’re now a day further along and the discomfort is still there.
Procrastinating on the thing that actually matters. Not chasing what you want is the easiest path available. Millions of people take it. It’s dressed up in very reasonable-sounding language: “I’m not ready yet.” “The timing isn’t right.” “I’ll start next month.” At some point, you have to see it for what it is.
What to do instead
Confront the discomfort rather than running from it. This isn’t motivational advice, it’s practical. The feeling of being lost is carrying information. It’s telling you something is misaligned, something needs attention. If you push it away, you lose access to that signal.
And then, act. Not a big dramatic pivot. Just one small thing today that points in the right direction. Research from Stanford’s Behaviour Design Lab shows that the smallest possible version of an action, taken consistently, builds more momentum than large sporadic efforts. You don’t need a plan. You need a start.
“Life is either a daring adventure or nothing at all.” — Helen Keller
That line is old but it holds. Being lost isn’t a failure state. It’s part of the journey. Every operator, founder, and professional who’s built something meaningful has spent time in this feeling. The ones who came out of it weren’t the ones with the best roadmap. They were the ones who stopped running from the discomfort long enough to figure out what they actually wanted.
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Reflect (YC W24)
What it does: A networked note-taking tool that helps you think more clearly by connecting your ideas, decisions, and reading across time. It’s built around how the brain actually works, not how folders work.
Use it when: You’re in a period of career or strategic uncertainty and need a place to think out loud, map your reasoning, and spot patterns in your own thinking across weeks and months.
What’s one decision you’ve been putting off because it felt too big? Hit reply.
Until next time, take care of yourself. Connect with me on LinkedIn
Rayn