I won’t leave my 20s with a fiancé, a checked off bucket list, or a shredded body. I didn’t party a lot, date a lot, or travel as much as I would have liked.
I will, however, finish my 20s with two things most people want but don’t get: A job I can do for the rest of my life and financial independence.
Not in an I-can-buy-my-own-island sense but in an I-can-feed-a-family-of-four sense. All without a boss and including multi-year, what-if-shit-hits-the-fan savings, earned from doing what I love.
Two of the biggest existential fears we have in our 20s are feeling lost in our careers and anxious about our financial future. I have eliminated both of them. Who can say that before they’re 30? Not many.
To me, those two things are success. You may define it differently, and that’s okay. But if you want those two things, if you’re okay with figuring out the rest later, here’s everything I’ve learned about how to get them.
1. Get a real job. Now.
Moving out, going to college, these feel like independence, but if your parents, a scholarship, or some other charitable entity pays your bills, you’re not independent. You’re vulnerable. You might think you’re going to college to fix that very problem, but you’re not.
College can’t teach you to find great work because college isn’t work.
It’s an ecosystem of a certain kind — the kind that’s built on relationships. There are many of these systems we might be a part of throughout our lives: A political party, high school, a church. While there’s always some work involved in staying in the system, ultimately, your skills have very little to do with how well you fare in it.
Yes, being productive is one way to signal you’re worth elevating to the higher-ups, but if you rely solely on that, you’ll fail miserably. You’ll also always remain dependent, looking for the next person to hand you a promotion and figuring out how to please them.
College is about working smart, not hard. Pick the right classes, the right assignments, the right deadlines, get along with the right teachers, know the right people in the right places, and you’ll be a shining star.
In the real world, you have to do those things too, but on top of it all and more importantly so, you have to create value. It’s not sunshine and rainbows out there. The market doesn’t care. If you can save $0.50 on a couple of bananas, you will. Why shouldn’t everybody else? It’s hard to make something people are willing to pay for.
If the salesman doesn’t sell, if the accountant gets the numbers wrong, if the dancer botches her performance, they won’t just not get paid. They’ll get fired. But if the salesman sells, the accountant saves, and the dancer entertains, they’ll receive leverage. Leverage in the form of money, connections, and opportunities. Now, they can take any job they want or make up their own.
Real value can only be generated in real conditions with real stakes.
Spending time, money, and energy on something that might not work, taking risks, making sacrifices, embarrassing yourself and feeling like an amateur — I get it, these things are scary, but they’re necessary.
I know college feels like a safe way of putting them off, but it’s not because putting them off is what’s unsafe.
My first three internships consisted of absolutely mind-numbing tasks: pretending to work at a computer (because there was nothing to do), sorting inventory at a glue company, and fetching the mail for a car dealership. But hey, they were just internships! In a real job, at least I’d get paid! Well…
My first summer job was removing price tags from shoe soles and stapling on new ones. I made about $5/hr doing it. Ouch. One of my first jobs in college was delivering medicine to elderly people. A few more things hit me:
- If I scratch this car, I’ll have to pay for it.
- If I mess up the delivery, someone will be in pain.
- If I work eight hours, that’s only one eighth of my rent.
Shit! Those are some bitter pills to swallow, but they’re still medicine. The only way these uncomfortable truths really sink in, however, is living them.
You can’t just read about being paid badly. You have to actually get paid badly. You have to feel that it stinks. That’s what’ll light your fire to do better.
So get a job. Get any job. But get started. Don’t stay on the sidelines. Don’t get lost in relationship games. If you’re in your 20s, and you’re not working, not learning how to pay for your own stuff and be a real part of our global economy, don’t expect these things to magically happen later. They won’t.
You’ll enter the workforce feeling wholly unprepared — because you are.
2. Work. Put in freakin’ work.
Every time Gary Vaynerchuk talks about the hustle at a conference, some guy will raise his hand and say, “Yeah, but I’d rather work smart!” Gary always has the same response: “I work smart and hard, now what?”
Like Gary, I can guarantee you that, no matter how hard you look, you won’t find a single person in your life who a.) likes their job and b.) makes a lot of money that didn’t put in ridiculous amounts of work. You may find people who like their job but don’t make a lot of money or people who are rich but didn’t earn it, but that combination? Work is the only way.
Hard work doesn’t feel like work at all if you like it.
Unfortunately, the kind of hard work you’ll enjoy takes a while to find. Most people never make the effort, and so most people never get there. Eventually, they settle into a mindset of “work is just work, and you shouldn’t enjoy it, you should do the minimum and then live your life.” This breaks my heart more than actual heartbreak because it’s such a limited, narrow, sad view of life.
You’re gonna spend a lot of time working whether you like it or not — you may as well learn to like it. Imagine spending 20, 30, 40 hours each week doing something that you can’t wait to stop doing every minute along the way. What a drag. What a soul-crushing experience. Fuck that.
Passion grows as you do. Even a bad job done well can feel rewarding. It can definitely be enough to act as a bridge to a better one. With mastery come autonomy and purpose, and this triad is the great enabler in feeling like you have meaningful work. Since mastery is the part you control, ultimately, it all flows from working hard.
For the first five years of being self-employed, I worked about 60 hours a week, every week, on average. That’s not a drink-on-Tuesdays schedule, but it also didn’t suffocate the rest of my life. Plus, most of it didn’t feel like work.
There’s nothing like going to bed at night knowing you did your best to make a positive difference in other people’s lives. Hard work isn’t the only way to do that, but it’s one of the clearest and biggest. Put in freakin’ work.
3. Adjust in small steps.
The reason you should get the next best job you can find and try hard to be good at it is that you can only go anywhere once you start somewhere.
A career is like a mountain range: In order to see how to get to peak A, you might first have to scale peak B. Climbers can point up straight and say, “This is the top I want to go to,” but they can’t guarantee a straight line is also how they’ll get there. Once they reach the first plateau, they might realize it’s a dead end — and off the path they go.
Everyone has an idea of what their dream job could look like, but no one knows if it feels like a dream until they get it. Not only is there no promise of it actually being fulfilling, there’s also a good chance you’ll enjoy one of your many detours so much you won’t want to return to the original path.
For any of this to happen, however, you have to choose a path, any path, and start walking.
The math of the universe that determines how it all eventually unfolds and works out is nothing shy of magic. You won’t believe how certain ideas, people, and opportunities can disappear so quickly from your life, and you’ll fathom how better ones wondrously appear soon therafter even less.
When I decided to be a freelancer, I began by offering translation services. German to English and vice versa. I’ve done three translation gigs to this day. People asked me to write content, so that’s what I did next. The writing inspired a blog, which inspired more writing, which led to coaching, then another blog, and I’ve been going from project to project ever since, more than half of which I never could have imagined back at the beginning.
That’s how this works and it’s not just amazing, it’s fun. You climb one hill, then find it leads to another. You uncover synergies. You pick up related skills. Your capabilities expand, and soon, you realize you’ve become pretty good at the intersection of a whole bunch of them. You build things, you jump on opportunities, and you use both to build a foundation right beneath your feet.
As that platform rises, so will you. Each one only feels like a small step, but after a while, you peer over the edge and realize: Damn, I’m up pretty high.
4. Don’t settle for mediocre.
While working hard and trying your best are only basic tickets to entry in the great game of meaningful work, rejecting mediocrity isn’t about scolding yourself when things go wrong or you made a mistake. It’s about continuing to shoot higher and refusing to let a bad status quo creep up on you.
In my first year as a writer, I pitched to get better and better contracts. After each gig, I didn’t just ask, “How can I deliver more value on the next one?” I also asked, “How can I get paid more on the next one?”
Towards the end of that year, I scored a ghostwriting gig for one of the top ten marketing blogs in the world. It was huge. I had to write 12 guides spanning some 4,000+ words each, but I also made around $8,000 from that one job.
I learned that getting the basics right (formatting, research, grammar, small SEO optimizations) gets you surprisingly far in standing out from the crowd. I also learned that I hate ghostwriting. I’d have returned all the money just to have my name on these posts — so I stopped. I haven’t done a single ghostwriting gig since.
Finally, I realized that even if you do great work its source might dry up. If one person controls your entire income, you’re still not independent. I didn’t want to constantly stress about the next contract, so I decided to build something product-based, something that could earn while I sleep alongside doing freelance.
It takes years for that direction to form, and that’s a normal and okay part of the process. For me, the uncertainty about what I want to do going forward slowly began to fade in year four. The big picture became clearer and now, each day more I spend in this line of work makes me want to add another tomorrow.
In your journey from peak A to B to C, you’ll find you enjoy some views more than others. Figure out which ones you like and keep climbing.
5. Save (and invest) your goddamn money.
Everything is a trap if you can’t leave when you want to. I’m gonna say it again: Everything is a trap if you can’t leave when you want to.
Don’t start all this and then get stuck in the very first part of the cycle: Trying to compensate for a lack of fun. It takes time to make the work itself feel rewarding, but until you get there, don’t lock yourself in spending habits you can’t get out of.
As great as the phrase ‘financial independence’ sounds, at the end of the day, it’s a crock. You always depend on the market. You depend on people giving you work, on your network rallying when you need it, on customers buying your products, and on the economy to not tank.
What saved money, be it cold hard cash or a basket of investments, can buy you, however, is time — and, with that, peace of mind.
I sleep easy knowing I can survive for a year, or two, or three, or four, depending on how much I stretch my budget. I feel calm even when nothing works because I have the option to walk away. That’s all I need.
Like actually experiencing bad work vs. just reading about it, even if you never play the “I’m done with this” card, it makes a big difference to simply know it’s there — and you can make sure it’s there. You don’t have to pray for good luck to pull it out of the deck.
From day one of working for myself, I vowed to put away 10% of my monthly earnings. Each month, I looked at how much money actually landed in my bank account, took 10%, and sent it straight to my broker and a separate reserve. Eventually, the reserve grew to covering multiple years of basic survival, and the brokerage account grew to $10,000+ in stocks.
Growing money is a game, a game you can learn to love, just like working hard. Some months, I saved as much as 70% of my income — because it was fun, not because I had to. I didn’t stint on cappuccinos, I just stashed away what I didn’t need.
I also decided to play this game more aggressively while I’m young and still have the energy and time to recover. It always makes sense to diversify a little bit, but if I take a big bet on cryptocurrency now and it doesn’t pan out, I can still make that money back and then some later.
Plus, again, as long as there’s a pillow of cash waiting for you, you might not fall softly, but you’ll always land on your feet.
Here’s another thing I’ve learned in my 20s: You can’t have it all. Maybe not ever, but definitely not all at once.
You might tell yourself if you can get just a little fitter, work just a little harder, go on just one more date, you’ll get the Schwarzenegger body, the promotion, and the girl. All in one go. That’s never going to happen.
Life is a bakery, and all cakes look delicious. Still, you can only eat so many slices before you’re full — and that’s okay.
I spent my 20s working, and I’ve arrived at the end of them with great work. I’m far from having it all, and there’s a lot I can and want to experience and improve. Still, I don’t feel like I missed anything. I’m happy about how I spent the time I spent and the outcomes it led to. That’s the main point, really.
This path is not for everyone, but if you feel like it could be, try it. You may just find it does work for you.
I can’t promise you’ll always pick your battles carefully or even consciously, but I do know this: If your 20s teach you that we must choose what to fight for, you’ll have spent them well regardless.