A Message For Those Feeling Lost In Their 20s

Society puts a lot of pressure on people in their 20s to “figure out” their lives.

The reality is, most 57-year-olds don’t even have their lives figured out. There’s no reason to put pressure on yourself so early in the process.

Here are a few things to remember as you’re navigating life in your 20s:

1. Take the biggest risks of your life.

Going “conservative” in your 20s is something you really, really should debate. Especially if you aren’t in debt.

When you’re this young, the number one thing you should focus on is executing on the most high risk behaviors of your life.

The biggest reason that so many people become unhappy is that they play life in “reverse.” They go for the safe and practical job right out of school, and they buy expensive stuff to impress their parents and friends. Then, it becomes less practical to quit their job because they’re “chained down” with expenses.

Instead, make high risk moves around the thing that will make you the happiest.

This is exactly when you should go live in Bali for a year. This is exactly when you should try and become Beyonce.

This is exactly when you go on the “offense.”

2. Don’t be afraid to take a $12 / hour job over a $52k / year job.

I’m a big believer in working for cheap (or free) for the person you want to try and become.

Getting “closest to the sun” is where all the leverage is.

Here’s what I mean by that:

If you go and work for someone you admire and do an incredible job, they could “put you on” and change the course of your entire career. For example… if you admire Alex Rodriguez or Chance the Rapper and you had the chance to run their social media for $12 / hour, there’s no question that would be be better than a job that pays $52,000.

Imagine what it would be like to be known as the guy or girl behind A-Rod’s social or Chance the Rapper’s videos.

Be humble, patient, strategic, and stop caring what your living situation looks like to people “on the outside.” You’ll set yourself up for an incredible future.

3. Do it because you enjoy the process, not because you’re chasing results.

When I look for talent, I’m obsessed with finding people who love the process — not the stuff that the game “buys” you.

If you’re focused on the cars, the shoes, and “posturing” to your friends, you’re finished. If you’re building a business or navigating your career based on what’s going to get you the off-whites, private planes, spa treatments, or jewelry, you’re not going to have a long career.

So many people in their 20s are taking jobs that pay a few thousand dollars more just so they can buy more stuff. Don’t get me wrong, I have empathy for people in debt. But a lot of people are taking these jobs because they’re trying to live up to the expectations of their parents and friends.

I look for people who “can’t breathe” if they’re not doing their art because those are the people who are going to win long term. For me, business is my art. For you, it might be design, performing on stage, or something else.

Whatever it is, be that person who’s obsessed with their craft and would be doing it for “free” no matter what.

4. Don’t stress about finding the answer to “what should I do with my life?”

If you don’t know what that “craft” is yet, that’s okay.

It blows me away how much pressure we put on people in their 20s and early 30s to have their entire lives figured out.

Of course you don’t know what you want to do yet – you haven’t even lived yet!

Now’s the time to be massively risk-oriented and try everything you want to try. There’s no “wrong” move you can make. If you genuinely want to spend every minute working like I did, great. If you want to travel to Bali or work in a vineyard in Tasmania, great.

Now is the time to go have different experiences and try different jobs until you find one you like.

5. Stand up to the people you love and have tough conversations.
If there’s one piece of advice you take away from this article, it would be this:

Have the conversations you need to have with the people you’re closest to.

Tell them the truth. Tell them how you feel about everything — about what you want to do, where you want to work, your insecurities, how you feel about their expectations, and everything else.

It will absolutely change your life. Even if they get angry and react poorly, their level of respect for you will be enormous.

It saddens me that so many people allow the opinions of their parents and their friends to hold them back in their careers, or worse, push them to make decisions that have terrible long term consequences (like taking on massive debt).

If you don’t have the tough conversation with them now, you’ll resent them in the long term because you lived your life for them and not yourself.

6. Stop debating. Start executing.

I implore you to not worry about the current judgement being deployed on you.

One of the biggest reasons I’m happy and can navigate my life so quickly is because I believe in one thing more than anything else:

The truth will play out in the end.

It’s not that I’m right or will be right, it’s that the truth plays out regardless. It’s pointless try to prove those around you wrong with your words.

Stay patient, and do it with your actions.