25 Pithy Yet Powerful Life Lessons


Joy and confidence and peace are fleeting, and — candidly — pretty new for me. I would argue I didn’t really consistently hit high marks in those areas until 2019, and I didn’t successfully start taking an exhaustive inventory of my life, habits, and mindsets until just over two years ago … when I started writing on Medium.

I was 34. I’m 37 now. Mercifully, you don’t have to wait that long.

I’ve had some moments of burnout and sloppiness and rage since, but I’m most of the way there.

And so, I’m going to share with you as many things as I’ve learned on that journey as possible. I’m gonna “give you the game” as the kids say.

Here are 25 small points to let marinate in your noggin.

1. You may already be a good, joyous, confident person, but just in existing in the wrong context. You may be a star without a sky. A lot of our lives — more than you think — are dictated by systems and institutions and societal norms. You’re not technically required to participate in most of them. (For example: American Life is needlessly cruel and competitive. You don’t need to be.) Really look and critically ask yourself if your discomfort comes from within you, or stems from a disagreement between you and the world around you.

2. Debt is indentured servitude. The less of it you can carry — financial, societal, emotional — the freer and happier you’ll feel.

3. Treating yourself kindly is hard to learn if you’re used to not doing so, yet it’s the best lesson you can learn. You can still work to become better, but you can start with “What if I …” And not “have to …” Now you’re cultivating grace and curiosity, instead of a militant Machiavellian rigor. The difference is enormous.

4. Most of our maladaptive traits and coping mechanisms come from bad programming — lies, traumas, conditioning — from when we were young. Really work to identify, deconstruct and distance yourself from that programming. You’d be surprised how much we see through the lens of others’ faulty projections.

5. If you find something you love to do, it doesn’t hurt to try and become world-class at it. For me, that thing was writing, and so I wrote for everyone, all the time, and continue to. Much of my newfound confidence comes from being able to say “I am one of the best in the world at …” and mean it. I don’t need awards or millions to validate this. I just know — and it allows me to feel like I can do other great things. (Let’s hope!)

6. If you’re able to embrace and cherish time spent with yourself, you don’t really need someone else to adore you. Of course, if you already do enjoy your own company, the floodgates open up. And — boy I tell ya — that’s really fun, too.

7. When at all possible, avoid doing sub-optimal shit with sub-optimal people. You don’t have a lot of time, attention and energy. 75–80 years on Earth. 24 hours in a day. 150 relationships you can realistically keep up with. Invest wisely.

8. Speaking of investing, drinking is very low ROI. Once in awhile is fine, but go easy on it. If it’s been a while since you’ve spent any considerable period of time sober, you might be surprised how your brain and behavior change. As for me, I’m certain I make 98% of my bad decisions — a rough estimate — while I’m drinking; 98% of my anxious, glitching indecisiveness happens on the days immediately after.

9. Cultivating healthy habits while spending time in solitude is sorta like depositing money in a savings account. Then, when other people afford you the opportunity to be a bit unhealthy, you can make withdrawals every now and again.

10. No matter how many risks you take, you can probably stand to take more of them. The human body often confuses excitement with fear; if you’re scared, more often than not, you’re excited. Do what excites you.

11. There’s no reason to lionize unnecessary hard work. Last year, I worked super hard to create the infrastructure required to leave my day job. Why? I knew I didn’t really want to work all that hard anymore.

12. Advertising’s sole purpose is to convince you you’re broken, so you can fix yourself, by buying what they’re selling. The less broken you feel, the harder a mark you’ll be. You don’t need to buy things to feel good about yourself if you already feel good about yourself.

13. If you want to change the world, harness your skill sets and use them to do good things that matter. You don’t have to over-complicate this. If your skillset is graphic design, make pretty and functional things for people who are actively working to improve the world. Supporting actors get a lot of work; you don’t have to carve out a lead role.

14. Set boundaries with everyone. By communicating and enforcing them, you teach people how to treat you, prevent relationships from turning toxic, and strengthen your boundary-setting muscles for the future.

15. It’s okay to distance yourself from toxic people, too.

16. Ask for what you want … Always. If the outcome’s in doubt, and it really matters to you, go for it — every time — with all the confidence you would if you knew you’d be successful or didn’t care how it turned out.

17. Learn how to be okay with a B+. With rare exception, an A+ usually isn’t worth the extra effort. (See above: finite amount of time, attention and energy, etc.)

18. Some of your problems are unfixable. Forgive and accept yourself for them. Learn how to work around them if you can’t work through them. (I’m disorganized AF, so I hired a housekeeper, and also someone to keep my priorities in order on an ad hoc basis. I realize not everyone can do this. I’m throwing money around.)

19. You don’t control all your happiness … just 51% of it. Enough to pass the bill, but not enough without a filibuster. Own that 51%, and fight for it.

20. If stuff doesn’t spark joy, get rid of it. If people don’t spark joy, get rid of them, too.

21. Trading time for money is almost always a bad investment, unless it’s a lot of effing money.

22. It’s still not too late to start, but it’ll never not get later.

23. Eat healthy foods you love to eat. If you don’t love to eat healthy food, invest in a high-quality set of seasonings and spices, and use them liberally. (Talking to you, white folks … The rest of the world’s had this figured out for centuries.)

24. Everything — life experience, information, circumstances, etc — in life is just data. What you do with that data and how you feel about it is up to you.

25. Don’t dim your shine to match the energy levels of others or make them feel comfortable. They may be doing that to you, too … now you’re all less than who you could be. In the long run, that shortchanges us all.

This article was originally published on PS I Love You. Relationships Now.