I tell people to “just try things” all the time. I just don’t mean do it blindly.
It’s one of those pieces of advice that takes the pressure off. You don’t need to have your life figured out. You just need to start somewhere and learn as you go.
And to be fair, it does work. Early on, almost anything is useful. You pick up skills, you see how different environments feel, and you start to understand what you like and what you don’t.
The problem is, no one really tells you how that advice is supposed to evolve as you gain more experience.
I spoke to Hassan recently, who’s been in that loop for a while. He made thoughtful decisions at each step. Switched majors when something didn’t feel right. Took on roles across teaching, sales, and tutoring. Built real strengths around working with people, explaining ideas, and staying composed in different situations.
None of those choices were random. I don’t think any of them were a waste.
But when you zoom out, it’s hard to tell what all of it adds up to.
Each step opened a new direction instead of narrowing things down. So every new decision feels just as open-ended as the last one. You’re still choosing between multiple paths, still unsure which one is worth committing to, still hoping the next move will somehow make things clearer.
At that point, blindly trying more things doesn’t solve the problem. It just extends it.
What’s missing isn’t effort or even experience. It’s being more intentional about what you try next.
Trying something works best when it answers a specific question. Does this type of work suit me? Can I see myself doing this daily? Do I want what people a few years ahead of me have? When you go in with that kind of focus, each step starts narrowing the path instead of keeping everything open.
And once you get those signals, you have to use them.
Double down on what showed promise. Cut the options that clearly didn’t fit. Look for patterns across what you’ve already tried instead of treating every new decision like a blank slate.
And before you commit, please, ask yourself a few simple questions that will save you a lifetime of regret.
What does this path look like a few years in? Are people getting hired into this, or is it getting more competitive? What do the people who succeed here tend to have in common? Do I want their day-to-day, not just the idea of it?
It’s useful to know what you like. It’s just not enough on its own.
At the end of the day, this is still a career. Your time, your energy, and in many cases your money are going into it. So your decisions need to hold up not just personally, but in the real world too.
That’s when trying things starts to work in your favor again.
P.S. Did you know, GradSimple Insiders is a Career Intelligence membership for early professionals who are unsure what to do next and want to avoid wasting years on the wrong path?
We break down real hiring data and job market trends twice a month so you can see which entry-level roles are actually in demand, which industries are slowing down, and whether a career path is worth pursuing before making a long-term decision.
