What's your next Idea???
you gotta fail fast to find out
At some point in your twenties (maybe your thirties), you sit down to figure out what you actually want to do with your life. You journal. You take stock. You read the right books and have the long conversations and stare at the ceiling long enough that it starts to feel productive. And then, after all of it, you end up more or less where you started: vaguely aware of some things you like, uncertain about everything else, waiting for something to click.
The problem isn’t that you haven’t thought about it hard enough. It’s that thinking that was never going to get you there.
When we were younger, we were sold a story that goes something like this: somewhere inside you, there is a true calling. Your job is to find it. Think hard enough, journal deeply enough, take the right personality test, and it will reveal itself. Then you’ll know, and the path forward will become clear.
This is almost entirely wrong, and it’s caused a lot of intelligent people to spend years in a kind of paralysis that feels like searching but is actually just waiting. And so this week, I wanted to write a relatively short piece on tangible things that have helped me create and work through new ideas… Hope this resonates!
What Actually Generates Good Ideas About Your Life
The people who seem to have figured out what they want rarely got there through introspection. They got there through volume and a lot of attempts, conversations, projects, and experiments that generated data about themselves they couldn’t have produced any other way.
A few things that actually work:
Take on projects outside your job description. The work you volunteer for, rather than the work you’re assigned, is much more diagnostic. When something is optional and you still find yourself doing it at 11pm, pay attention to that.
Talk to people doing the thing, not people who advise on the thing. Career coaches and self-help books deal in abstractions. Someone three years into the actual job will tell you what Tuesday feels like, which is the only information that matters.
Do cheap experiments before expensive ones. Before committing to a new career, find the smallest possible version of it you can do right now. Freelance one project. Volunteer for one weekend. Write one piece. The goal isn’t to succeed. It’s to find out how it feels to try.
Notice what you’re already doing without being asked. The things you do in your spare time, the rabbit holes you fall into, the problems you find yourself thinking about in the shower are data points most people ignore because they don’t look serious enough to count.
The Real Cost of Waiting for Certainty
There’s a comfortable feeling that comes from keeping your options open. If you haven’t committed to anything, you haven’t failed at anything. The dream stays intact. The version of yourself who figures it all out and does something meaningful remains theoretically possible.
But time spent waiting for certainty is time you could have spent generating it. Every year you don’t try things is a year you don’t learn what you actually think of them. The cost of inaction isn’t zero, it’s all the information you would have had if you’d started earlier.
The people who struggle most with this question at 35 are usually the ones who were too cautious at 25. They optimized for not making the wrong move and ended up making no move at all.
And so, after years of reflecting on this, I think “What do I want to do with my life” is just an objectively bad question. It’s too large, too permanent-sounding, too loaded with the implication that there’s one right answer you might miss. It makes the problem feel bigger than it is.
Better questions are smaller and more actionable:
What do I want to try next?
What would I do if I knew I could quit after six months?
What’s the most interesting problem I’ve encountered in the last year?
What kind of work have I done that I’d describe to someone else with genuine enthusiasm?
These questions have answers you can act on. The big question mostly just produces anxiety.
The Only Real Advice
Try more things and fail fast.
Try them smaller and faster than feels meaningful.
Keep track of what you notice about yourself when you do.
The data will accumulate and at some point, you’ll find you have opinions you didn’t have before, i.e. a rough sense of the direction that feels more right than the others.
Real clarity isn’t a singular moment. It’s just what happens after enough reps.