The best way to win the “career lottery” might be to give up on the idea that it exists at all.
I don’t think anyone wins the career lottery. Saying someone was “born for” something is a convenient shorthand for a lot of hard work and experimentation. Sure, you can point to Beyoncé and say, “She’s doing what she was born to do,” but I bet she’d be a pretty good accountant or something if she wanted.
You could look at the desire to do something “better” than working the same boring job your whole life as a generational shift, but that’s a bit simplistic. It’s not that we have different values. We have different opportunities. People get hung up on this idea of finding a calling, but you don’t need to know what yours is. You just need to try a lot of different stuff. That’s easier during times of uncertainty. Instability has made us more open to change, perhaps because we’re afraid and forced to adapt, but also because there’s more possibility. If you look at American companies, many of the biggest were founded by entrepreneurs during a depression or recession.
Whether you’re an entrepreneur or an employee, you need to own the idea that you’re self-employed. No one cares as much about your career as you do—even if you want to keep working for an organization, the point is that you’re looking out for your own interests. Put forward your priorities and think about what you actually enjoy doing. Honestly evaluate how joy, money, and “flow” intersect for you—in a meeting, on a call, or even doing something you thought would be a dream project. Listen to the compliments you receive. People from the outside can often point to our strengths better than we can ourselves. Ask, “Did I take joy in that or did I feel anxious?” About flow: Well, do you ever lose yourself in something? Can an hour go by and you don’t realize it? If you’re struggling to feel that at work, pay attention when it does happen. Ask to take on duties that give you that opportunity. Start a side hustle. The barrier of entry is so low that everyone should have more than one income source, if only because it produces a disproportionate amount of security and confidence. Even if you don’t make much money on it, you’ll always know you could do something else if you lost your job, or if it sucks so much you have to escape it.
The people most likely to end up with meaningful work are discontented. Not necessarily miserable, just frustrated. They don’t want to do things the way everyone has before. People look in from the outside and think, “It’s just so terrible because there’s no clear, linear path.” Well, why would we want there to be? Are you feeling unsettled? I hope so. That means you’re on the right track.