28 Lessons from 28 Years

I turn 28 this week. I hate my birthday, but always make a point to reflect on what I’ve learned in an effort to inform where I should go. I actually found it quite hard to narrow it down to 28, but it was helpful to bucket things together and discover themes.

1. Don’t Be a Dick

It’s my #1 because it feels good to be a dick, sometimes.

“That customer support rep had no fucking idea what they were talking about. How incompetent!”

While lashing out may feel good in the heat of a frustrated moment, it’s never pleasant to recall how you behaved rudely to someone. Burning a bridge is never a good thing. Check out my notes on How To Win Friends and Influence People. Carnegie does a better job of explaining how it’s never the correct path.

2. Call your mom

She's your biggest fan. She wants you to succeed, and she would love to be a part of it. I’ve talked to friends my age who go weeks without phoning home. I think that’s sad. If your mom is around, chances are she wants to hear from you.

You should want to hear from her too. She remembers everything about everything you’ve ever done. There’s important information about yourself in those memories.

3. Call your friends

1 in 7 men and 1 in 10 women report not having a single friend. Scott Galloway talks a lot about this. It’s a disaster. If you have a great friend that you talk to all the time for advice, you’re incredibly lucky. Tons of people go through life carrying all that stress. It gets harder as we get older, so carve out time to keep up with friends.

4. Travel

No, but actually do it. Not just to your buddies' bachelor party. I spent $15k going to Africa for a month to climb Kilimanjaro and I don’t miss a penny. Jack Raines has a great piece on this.

Don’t go to an all-inclusive hotel in Mexico. Go somewhere you know nothing about. Visit a community that has terrible tourism infrastructure. Live like a local there for a couple of weeks. It’s cheaper and more memorable.

5. Waking up early is for everyone

Waking up early is a cheat code since most people roll out of bed and open up their email. To get to bed earlier, I stopped doing things after 10:30/11 pm and I don’t miss it. When I was waking up at 9 am, I missed the early morning calm like a fat kid missed cake.

6. Do 1 thing every day that you look forward to

If you work remotely and it’s winter (95% of my followers) this is huge. Don’t let the days bleed together. Life is short. When I look back on some 3-4 month chunks when COVID first started, I have 6 memories.

I’m pretty sure I don’t remember the entire month of February 2021. (I had COVID and everyone else did. I just stayed home on my laptop) That’s terrifying. Create memories so life doesn’t seem as short. You don’t need other people to get this done. Going to an amateur comedy hour by myself is a great use of time.

7. If you don’t read books you’re missing vital information

Most people understand this is a huge gap in their routine, but do nothing about it. I won’t waste time convincing you that reading is important. I will waste time encouraging you to block 20 minutes at the beginning of the day to get this done. It can be any book, just read.

8. Cleanses don’t work, consistency does

I thought completing the 75-Day Hard Challenge was difficult. It was, but staying consistent without placing a finish line on when you can go back to being a shithead is more challenging. Dry January is a great way to try sober living. It means nothing if you black out on February 1st because you can’t stand the thought of being sober another day.

“We are what we repeatedly do. Excellence, then, is not an act, but a habit.” — Will Durant (it’s actually not Aristotle).

9. Break your heart

Don’t be afraid of dating because of heartbreak. Don’t be afraid of anything that might result in that outcome. It’s unavoidable and will teach you some interesting things about yourself.

10. Learn some sort of fighting/self-defense technique

It’s a little dishonest of me to write this since I don’t know one (unless you count 2 years of high school wrestling). Call me paranoid, but I’m reminded every day that it would be useful to know how to defend myself if shit ever hit the fan. A 2023 goal of mine is to learn basic Jiu-Jitsu. I don’t want to learn this lesson the hard way.

11. Run/ walk every day

Running is amazing, but if you don’t run, walk. It may seem counterproductive to whatever task you are currently working on. It’s not. It’s the best way to ideate. Your mind will have time to process daily inputs and you’ll be surprised by the creative strategy it delivers as a result. Do this without your phone,

12. Move to the big city

Do it. Moving to New York at 23 was the best thing I’ve ever done. New York is the Mecca, but I’m sure other Top - 20ish cities would get the job done. You might hate it, fine. That’s information.

Whether you like it or not, cities are concentrated areas with top human capital in any respective industry. Art, science, finance, you name it. Covid changed that for a couple of years but migration patterns have shown that people are returning. Idaho is not becoming the new San Francisco.

13. Ask people who didn’t like you at first why they didn’t like you

This is super uncomfortable. Don’t take it personally, we rarely know someone’s core character until we truly get to know them. Odds are they were probably wrong about you anyway. Maybe you came off as disinterested or disrespectful. Why did they feel that way? Be as objective as possible and see if there’s an opportunity to change how you interact with people you just met.

14. Delete Instagram, TikTok, and Facebook

Odds are you know someone who has done this and swears by it. These apps are poison. TikTok is banned in some states already. It’s pure consumption. If this is the medium you rely on staying in touch with friends for, they either aren’t your real friends or you need to call them instead. If you say, “Tik Tok is great when I want to unwind at night” and you truly only open the app once for 30 minutes at night, you are the most self-disciplined human being on earth. Congrats.

15. Stop watching the news

Nuance matters. Fox and MSNBC lack any of it. See above for my argument about pure consumption.

It might make you feel informed. You’re not fully informed. It’s free, and you get what you pay for. There’s a higher cost to being embarrassingly biased on any topic. Subscribe to more in-depth literature if you must stay up to date on current events. The Economist is great.

16. Scare yourself intentionally

Do it to yourself before life does it to you. You’ll be thrust into uncomfortable situations and environments all the time. Practice it. The worst thing you can do is show up unprepared for inevitable disasters.

17. Fiction > Non-fiction

The Alchemist is my favorite book because it tells a story about a boy chasing his dream and learning valuable lessons along the way. Nonfiction books can be helpful for research, but fiction books, at least for me, are direct calls to action. I can also sit down and devour fiction, while Non-fiction can be more like a chore.

18. Journal 

Do this with recurring thoughts especially. Chances are your brain is filtering your focus on a specific aspect of the problem that it considers a threat. Write it out. Don’t waste your time trying to format it. This is for your eyes only. Journaling as a consistent habit will result in greater proficiency when problem-solving.

19. Talk to really old people

Ask them who they were when they were young. What would they tell themselves at your age? What do they regret most? Do this as much as you can. Sahil Bloom did this on his birthday with ~10 people in their 90s and discovered profound perspectives from people who had nothing left to do but reflect.

20. Stop drinking. Or at least carefully limit alcohol

When you’re young, drink. Your late teens and early 20s are a perfect time for it. Understand what your relationship with alcohol is by trying different types of liquor and wine. Get drunk with your friends. But one day you start to realize it’s not as inconsequential as it once was. Most people my age talk about alcohol as that friend who they keep around because they have so much history with but don’t really like anymore. I get it, it won’t happen overnight. But eventually, it might be time to sit down and break up with it altogether.

I’d like to challenge someone to find and send me a scientific document proving a single benefit of alcohol.

21. Learn a new language

Again, this is a bit dishonest of me since I am only 30 days into my 2023 goal of becoming fluent in Spanish. The habit itself has already evolved into something I look forward to every day, however. It’s exciting to learn a new language because of the possibilities associated with the skill. For 30 minutes every day, I get to pretend I’m in a different country talking to locals in their native tongue. I’m nailing the I/you/ we conjugations in the past tense and associating each adjective with its correct masculine/feminine form. It’s also good for your brain apparently.

22. Meditate

Meditation is the last habit I’d give up if I had to choose just 1. It’s all the rage these days, and for good reason. It’s not a wellness trend. It’s survived thousands of years.

Expressing anger makes you angrier. I used to think the opposite. Meditation allows you to sit with uncomfortable emotions by becoming aware of their impermanence. Sit down for 10 minutes every morning, close your eyes, and gently become aware of what pops into your head. Then let it pass.

23. Make amends

Life is short. I look back on the number of falling outs I’ve had in my younger years and kick myself for letting my ego get in the way and not apologizing sooner, even if I don’t think I’m to blame. If you unpack the issue, chances are one person misunderstood the other and you can talk it out. To echo my point from above, friendships are incredibly valuable.

24. Don’t lie

We usually lie because we’re afraid. Afraid of being found out, afraid of facing an uncomfortable consequence, etc. It’s a slippery slope. Letting it become a habit is dangerous. Soon we might find ourselves telling a lie just because we’re accustomed to it. The final blow arrives when we begin lying to ourselves. Don’t let it get this far.

25. Money can buy happiness if you spend it on things that make you happy

Figuring this out pissed me off because I’ve been told since I was a toddler that money doesn’t buy happiness. For some reason, it’s indoctrinated into our culture. The statement “Money can’t buy happiness” is terribly misguided and devoid of numerous caveats. Seeing your bank account get bigger doesn’t make you happy, but living a life free from financial stress certainly helps a ton.

I yearn for the day when my net worth becomes my sole responsibility and I have enough capital to fund my own projects that add value to people that need it. Or when I can make a massive bet on a risky idea that I have with very little downside.

We see ultra-wealthy people who are miserable and argue that it’s because they have too much money and have lost all purpose. This argument is lazy. While it could be true that they no longer know what to do with themselves, it’s not because they have too much money. It’s because they aren’t creative.

26. Stop watching porn

It’s a big problem for people (mostly men) in this country. It’s so readily available and so much easier than actually interacting with a potential suitor. It’s a great way to not feel lonely, if only for a little.

It’s also a great way to numb any impulse you might have to build yourself into someone that’s sexually attractive to others. That’s an impulse you should be tending to.

27. Plan your day the night before

I’ve gotten to the point where I’m so terribly discombobulated if I wake up and realize I didn’t draw out the day the night before. I have to scramble to prioritize the day while I’m living it. Usually, that puts me in reactive mode in the AM when I need to be proactive.

I don’t know how I once lived like this every day. Maybe I had less responsibility. But I know I was not optimizing my time. By the way, this doesn’t mean you have to be robotic with your schedule. I schedule my day ahead so I know when I can look forward to more passive activities at the end of the day. Typically I’ll schedule breaks to do whatever I want. Or 4 hours at night to get into adventures. But it’s because I’m rigorous in scheduling focus blocks that I’m able to do more recreational things with peace of mind.

28. Go to therapy

Fine, I’ll admit. Not everyone NEEDS to. I won’t be one of those people who are in therapy that wants everyone else to join so they feel better about themselves. I do think it’s a great way to introduce an objective voice to your inner monologue. Letting the voice in your head go unchecked is dangerous. You might have friends who you bounce ideas off of and you’re lucky. Though chances are, if you complain a lot to your friends, they start telling you what you want to hear so you shut the fuck up. There’s a reason therapy costs money.

I pay someone to listen to me rant about all the shit I wish was different. And every week he sits there and listens like I’m a vessel for the voice of God. It’s an incredible talent.

What did I miss? Let me know.

Matt