17 Lessons I’ve Learned After 5 Years in the Real World

It’s weird to think I’ve been out of college longer than I was in it. Over the past four years I’ve recapped some harsh but valuable lessons I’ve learned in the real world  (2019, 2020, 2021, 2022). But 2023 has been the most instructive year by far, mainly because I went through the process of publishing my first book and moving to Los Angeles while running my marketing business.

Will I look back five years from now and realize some of these lessons were misguided? Probably, but who cares? Better to change your mind than cling to ideas because you’re afraid to contradict yourself.

Speaking of which…

1. The worst person you can lie to is yourself.

2. Most people prefer socializing with people who find them interesting—not people they find interesting.

3. If you start a creative project by calculating how fast you can earn $__________, you should stick to your day job.

4. The only time to take someone’s advice seriously is if they have something to lose by being wrong.

5. Some “silly” purchases actually net you money because they scare you into working harder to maintain them.

6. The idea that having a day job is incompatible with creating art or starting a business is just a lame excuse to not try. You can accomplish more with a few hours of deep focus each week than you can with months of unstructured time.

7. Good habits almost never survive bad environments.

8. Stop trying to fill the 5-10 minute gaps between meetings, chores, tasks, etc. You’ll feel better if you just wander around aimlessly, stare outside, or (if you dare) think.

9. If you want to “find more time to read” look at the screen time breakdown on your phone.

10. The new cult of AI dorks fail to realize that the most compelling thing about art is that someone suffered to make it.

11. You’re never “ready” to make life-changing decisions. Prepare yourself to jump before you spot the landing.

12. The harder you try to define yourself, the less you know who you are.

13. Don’t bet against the person who just keeps showing up every day.

14. “Someone who says ‘I am busy’ is either declaring incompetence (and lack of control of their life) or trying to get rid of you.” – Nassim Taleb.

15. The fastest way to eliminate distractions is to stop doing work you hate.

16. Become a regular somewhere (a restaurant, coffee shop, etc.) and tip generously. It feels good and normalizes not freaking out about small amounts of money.

17. Many self-proclaimed cultured people won’t drink cocktails out of plastic cups but will gladly read novels on a Kindle—or worse, listen to them.