You do not have the luxury of being stuck in your 20s. You can be searching and finding nothing. That’s okay. But doing nothing is not okay. And accepting that your 20s is a time of getting nothing done is not okay. Because your 20s are the time to figure out who you are. It’s not like you learned about that in school, right? And the people who are the happiest in life are the people who understand how to meet their own needs. In order to meet your own needs you have to understand what they are. That’s your job in your 20s. Here are three ways to get it done better:
1. Seek out ways to fail.
Most people have no idea what they are doing in their 20s. So you have to try stuff. It’s highly unlikely that you’ll figure out everything you can do well and feel good doing well on your first try, you can’t measure success by a lack of failure. Instead, you have to measure success by how often you are failing. You do something and it doesn’t work and you do something else. The failure is a sign that you are moving forward by eliminating the things that are not for you. Not failing is a sign that you are stuck.
This means you have to fail in front of your friends and family. They will say, “What are you doing now?” and you’ll give an answer you are unsure about. Maybe it’s uncool. Or you’re unhappy. Or maybe your family thinks it’s a terrible thing to be doing. That will be your answer. Because that’s where you are. And maybe next time there will the next answer. That’s fine. The path to success is failure. Make sure you are on that path.
2. Find others who are also on your path.
You know what you’re aiming for. Even if you think you have no idea what you’re aiming for, then you’re aiming to figure out something to aim for. What you want to do is look at other people who are doing what you’re doing.
One of the most popular posts I’ve written is a letter to parents that says, “Stop worrying that your twenty-something is lost.” And it’s basically a message to parents that they should look at their unemployed, debt-burdened, twentysomething who is living in their basement in the context of the other twentysomethings. People who have the most success life are the people who learn to cope with that feeling of being lost, and that’s what their twentysomething is doing in the basement.
Being lost is a coming of age moment that you go through after years of having teachers tell you what to do. Success in your twenties probably looks like flailing. But you don’t know that if you only look at one, single sample.
3. Seek internal validation, first and foremost.
You can tell if you’re on a good path if you are moving away from seeking external validation. Straight paths through corporate life are actually infantilizing: you try to win a job from someone else, then you try to get gold stars from that person, in the form of accolades, money, and promotions.
Jessica Livingston from Y Combinator explains that the first step someone takes to becoming an entrepreneur is to stop looking for external validation. At the beginning, all entrepreneurs look crazy, unreasonable, and unemployed. And to make it, you have to be able to live with that —people telling you that you are a disappointment, a failure, and how you are not living up to your potential.
It’s hard to tell if you are doing a good job of running your own life, but just ask yourself, “Am I actually trying to run my own life, or only letting other people tell me what’s good for me?”
4. Don’t be first and don’t be last.
Paths that have had a million travelers are probably already finished. At this point, those paths succeed for almost everyone only in alternative realities. For example, getting a PhD in the humanities assumes that there are actually jobs in that field that can support an adult living in the US. This is not true anymore, not in this reality. Another alternative reality supports taking out loans to go to law school. Because in this reality, most law school graduates don’t get jobs and can’t pay back the money.
The point here is that you want a path that someone else has taken, with success, but not too many people have followed already. Sixty-five percent of the jobs Generation Z will enjoy do not even exist today. So you that you need to be taking paths that are fresh, like big data or virtual property lawyer.
Those were easy examples, though. Here are some others, less obvious. For example the path of starving artist model is over. It’s not something that’s open to people anymore because it’s stupid. There is nothing stopping you from taking a day job. There is nothing stopping you from doing art at night. Or vice versa. We know enough about art to know that living the life of a crazy person is dangerous, not glamorous
It’s hard to find the right path, but the good news is that you don’t need to be on the right path, you just need to be on any path. There’s a big difference between avoiding all paths and testing paths that don’t work. Think of this list as guidelines for the next path you test. And remember you learn much more by failing fast and often than moving slowly so you don’t fail at all. 
