Brutal pieces of career advice for early 20s

Now that I’m officially 21, I think it’s time I share some harsh big brother career advice.

Just kidding. I still have much to learn myself. But here are 7 things I wish someone had told me sooner (that will hopefully save you some time):

#1: Get good at a valuable skill. Everything else is secondary.

I've had a lot of young, hungry people reach out to me asking how they can work with me. While I'm flattered, I also candidly feel scared on their behalf because I just don't have a ton of work they can help me with.

A lot of the things that used to be given to junior people, whether it was data analysis, ops, or one-off tasks, can now be done with an AI agent. It's never been a worse time to be an inexperienced generalist.

That said, it's also never been a better time to go really, really deep on a valuable skill. Once you develop that expertise and domain knowledge, you're able to amplify yourself a ton with AI.

Speaking of AI…

#2: Embrace new tools faster (like AI)

I'm not proud to admit it, but I’m man enough to say it... It took me 4 months to download Grokbot. Once I did, it took me 4 minutes to create an AI automation that immediately saved me 40 minutes of work.

For the longest time, I thought learning how to use AI agents would take too long and that I was better off just continuing to do the thing I was doing and ignore AI. That was just cope.

We often spend more time procrastinating on doing the things we know we should be doing than it takes to actually do them.

I think we're at a point in the world where it's pretty obvious that AI is not going to go away. It is now forever entwined with our future. Whether it aligns with your morals or ethics or not, I think it's worth at least experimenting with and tinkering with it to understand its possibilities.

And the cool part about learning how to use AI is you can open up AI and ask it how you can use it, and it will tell you.

#3: Learn how to write

There are many reasons to write. Some people write to express themselves creatively, clarify their thinking, or build an audience of raving fans. At the highest level, I think writing matters because writing is thinking.

If we know that a good life is the collective sum of many good days lived in a row, then the better we write (that is, the better we think), the better decisions we make. That ultimately leads to a better life. By learning how to write clearly and how to edit or rethink, we are practicing the art of making better decisions.

I've gotten everything I've wanted out of life (except for a wife 🥲) from committing to the craft of writing and sharing my thoughts on the internet.

If you're like, "Okay, Jay, you've convinced me, but where do I start?" I think one of the simplest ways to start is to open up a Google Doc and at the top write down a problem you want to solve. Then start writing to yourself about how you would solve that problem. Don't break the chain. Keep writing and writing and writing.

#4: Do the work upfront

If you are young, broke, and have nothing going for you, then your greatest advantage is that you have nothing going for you.

You want to trade what you do have (your time, energy, and drive) for things that you don't have: a skill set, a network, and credibility.

One of the best ways to do that is to work for free.

When I say "work for free," I don't mean cold-emailing strangers and saying, "How can I work for you?" or "I'll work for you for free." That puts the burden on the other person to figure out who you are and how you can help.

When I say "work for free," I mean do the work for free up front:

1. Do your research on someone you want to work with.

2. Run an audit on what they're doing well and, more importantly, what they can be doing better.

3. Put together your thoughts in a pitch deck, memo, or presentation, and send that to them for free.

That allows you to do two things:

1. It shows the other person that you want the opportunity.

2. It shows the other person that you can do the opportunity.

It reduces the friction it takes for the other person to say yes, and that is one of the best ways to get your foot in the door and create opportunities.

#5: Keep a swipe file

A swipe file is a fancy way of saying a folder of things that you find interesting and useful.

I keep a swipe file for everything: questions I love, sentences that stop me in my tracks, cooking recipes I know I'll probably never make but may in the future, and romantic things I want to do with my future wife.

There's a quote I love that says, "The best time to dig a well is long before you're thirsty."

I think, on a similar note, you never want to be caught flat-footed. Save the things that inspire you, move you, or that you find useful. You think you'll remember them when the time comes for you to remember them. But the truth is, you won't.

Start now.

#6: Optimize for proximity

Proximity is power. One of the greatest things you can do for your career and life is to get as close as possible to the people who are living the life you want to live and learn from them.

When you get to see excellence up close, the standards they have for their work, how they solve problems, and the mental models they use in their decision-making, you can't unsee that.

The best lessons are not taught through a textbook; they're caught through observation. Which is why I fundamentally believe apprenticeship is one of the few career slingshots that still exist.

Seek out the best. Learn from the best. Become the best.

#7: Share your thoughts online

I know this is semi-related to the point above about learning how to write, but I want to emphasize this point because there has never been a better time in history to increase your surface area for serendipity.

Sharing your thoughts online is not about becoming an influencer or being vain. It's about understanding that opportunities flow where attention goes. If all the attention is on social media these days, then it makes sense to insert yourself into the stream of opportunities and start to build digital real estate for yourself.

One of the analogies I think about a lot comes from Sun Tzu, a military strategist. He said that in war, you want to imagine yourself as a boulder at the top of a hill, where you have many different options. You can roll down in many different ways. The worst place to be is as a boulder at the bottom of a hill, because you are stuck.

If you want to massively increase your surface area for serendipity, your optionality, and the number of opportunities you have available, then build a personal brand. Basically, that just means sharing your thoughts online to develop a reputation so that you can be intentional about the associations you want to create, rather than relying on the associations people make of you by accident.

Hope this helps!

Until next week,

Jay “Reminders, Not Advice” Yang

Author of You Can Just Do Things & Work With The Best

Ps. Hahaha

T.E. Lawrence on being a dreamer and doer:

“All men dream: but not equally. Those who dream by night in the dusty recesses of their minds wake in the day to find that it was vanity: but the dreamers of the day are dangerous men, for they may act their dream with open eyes. to make it possible.”

C.S. Lewis on love:

“There is no safe investment. To love at all is to be vulnerable. Love anything, and your heart will certainly be wrung and possible be broken. If you want to make sure of keeping it intact, you must give your heart to no one, not even to an animal. Wrap it carefully round with hobbies and little luxuries; avoid all entanglements; lock it up safe in the casket or coffin of your selfishness. But in that casket—safe, dark, motionless, airless—it will change. It will not be broken; it will become unbreakable, impenetrable, irredeemable. The alternative to tragedy, or at least to the risk of tragedy, is damnation. The only place outside of Heaven where you can be perfectly safe from all the dangers and perturbations of love is Hell.”

If you feel lost, get more specific.

Why do you feel lost?

1. No target - can't say what you're moving toward.
2. No feedback - can't tell if today was a win.
3. No next action - can't name the next step.
4. Too many open options - nothing chosen, so nothing compounds.

At the simplest level, if you do more you will win.

More volume
More testing
More iteration
More feedback
More improvements
More time in the game

You can probably do more than you are right now.

The fire of envy only leaves the ashes of emptiness.

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