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How to win in your 20s

The better the relationship, the fewer times you need to call, more times you want to call, and easier it is to jump right back in as if no time has passed.

True intelligence isn't just about getting what you want. It's about enjoying the journey toward getting what you want.

If you’re worried about the price of going after what you want, just remember the price of staying exactly where you are.

“Everyone has an invisible sign hanging from their neck saying ‘Make Me Feel Important.’ Never forget that when working with people.”

— Mary Kay Ash

Nietzsche:

For the past 5 years of my life, I have been obsessed with how to “win” my 20s.

Here’s a non-exhasutive list of advice that has helped me:

  1. Move out of your home town. You don’t realize how much your environment affects your ambition. There’s a quote I love: “We only dream to the size of our exposures. Because what we’re exposed to is the only things we think are reachable.” Not saying you have to leave forever, but it’s definitely worth changing your environment.

  2. Treat school like a day job. Everyone complains about how school doesn’t teach many “real life skills”, but then they don’t do anything about it. What’s helped me is adopting the belief that school isn’t there to teach me anything and it’s on me to educate myself. So both before and after classes (and technically during class 🤫), I would work on my online projects and ideas. It changed my life. You learn way more from working on a real-life project than sitting in a lecture hall.

  3. Write online. You will be told to “network”, but the way they teach you to go about it is all wrong. The best people you want to know are NOT going to networking events and coffee chats. They’re too busy building stuff and working on improving themselves. You should do the same. Level up your skills then share what you’re learning online.

  4. Get insanely good at cold outreach. Study some basic copywriting. Search up good cold emails. Then practice by shooting your short. You don’t even have to ask for anything. Start by sending a thank you email to your favorite author or entrepreneur.

  5. Build a cash-flowing agency >> VC-backed startup. For some reason, colleges like to make you think that you have to start a venture-backed startup if you want to be an entrepreneur. That is not the case at all. In fact, you will probably learn more (and earn more) by starting an agency and focusing on signing clients than making pitch decks to win a $500 pitch competition.

  6. Create a story bank. At the end of each week, reflect on your past week and document any cool things that happened to you. It doesn’t have to be a long journal, it can be a few sentences or bullet points. Trust me, this will come in handy in the future.

  7. Adopt a weekly reflection habit. Speaking of weekly reflection, one of the best habits I’ve adopted is reviewing my past week and planning my next week. Why? Because life has a way of steering us off course from our goals. This helps keep you in check.

  8. Never sacrifice your reputation for short-term gain. Never ever ever ever do something that you wouldn’t be proud of telling your grandparents or future kids about because someone offered you money. Don’t do it. It’s not worth it. I will not elaborate.

  9. Learn to cook a few staple meals. It’s been about 9 months since I started living alone in Las Vegas and I’m soooo glad I learned how to cook a few dishes that I can rotate between. If you have a favorite dish or meal, ask the person who made it how they made it and learn!

  10. Work for someone you admire. Not only will you have a high likelihood of learning, but it will also demystify the idea that your idols are superheroes with magical powers. They’re not. They’re human beings who eat, breathe, sleep, and shit just like the rest of us.

  11. Do your very best to see what great looks like. I truly believe one of the most valuable things you can do for your career is to see what “great” actually looks like. Because once you’ve seen it, you can never unsee it. It becomes the benchmark you measure against for the rest of your career.

  12. Don’t be afraid to quit things. There’s this idea that you have to find your purpose or calling and stick with it for the rest of your life. But I’d argue your 20s are for figuring out what you enjoy and are naturally good at. Don’t chase what’s hot or shiny for the sake of it. Sure you might get ahead in the short-term, but in the long-run you will get lapped by those who have found their superpower.

  13. Skip the typical first job and go build stuff on the internet. Your first job is typically to teach you how to show up on time, follow rules, talk to customers, and be reliable. But if you already know how to do those things, skip the job at your local coffee shop and build things online. Start an agency, build an app, design a website.

  14. Get AI native. You should be spending at least an hour a day tinkering with and using all the latest AI tools. People can debate it all they want, but it’s no secret AI will continue to improve and become more prevalent.

  15. Create a life philosophy. Take a weekend just for yourself. Reflect on what you want and don’t want out of life. Get as specific as possible. Write it down. It doesn’t have to be perfect. Most people don’t spend enough time thinking about the big questions in life.

  16. Get in shape. You already know this. You will never have as much free time and energy as you do now. Use it.

  17. Don’t stop playing sports. At the very least, sprint or jump once a week. You will be surprised how quickly your body atrophies when you don’t use it.

  18. Optimize for serendipity. Work at a coffee shop instead of your room. Live close to the city where things are happening rather than further away to save a couple bucks. Say yes to random meetups if the alternative is rotting away in your room. Luck is probability… and you want it on your side.

  19. Be open to learning from everyone you meet. Everyone has something to teach you (even if it’s what NOT to do). You will never reach your full potential if you constantly think you’re smarter than you are. You can’t learn what you think you already know. Empty your cup.

  20. You already know what it takes to live a good life. To give more than you take. To love more than you hurt. To do hard things, love your family, and work on meaningful projects. The hard part is not getting distracted with all the chaos going on around you. Be kind, work hard, be patient and you’ll do well.

Until next week,

Jay “In My 20s” Yang

“Short enough to read in 30 minutes. Impactful enough to change the rest of your life.”

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