26 Lessons Learned - 2yrs After Selling My Business

Photo by Alexander Grey on Unsplash

1. Financial advisors are like real estate agents; most are bad. But the few that are helpful can be a value-add.

2. Psychology affects market returns. Dollar-cost averaging a portion of your salary differs from allocating $50m. Theoretically, you may know what to do, but it’s difficult to pull the trigger in reality.

3. Switching from living on w2 income to a portion of your portfolio is a difficult mind shift.

4. Whoever you tell about your exit will tell others.

5. Prepare to be lost, identity-wise, for a few years. It’s okay and normal. More on this.

6. I’m less risk-averse than I used to be. In a sense, I won the lottery. Why risk it?

7. Taxes are a significant expense I don’t spend enough time on. I’m working on this. Consider tax loss harvesting, a strategic CPA, municipal bonds, your primary state, etc.

8. I did the hard work, but timing is everything. I was lucky to exit in a hot year that drove massive returns.

9. It took me 1 year and an Antarctica cruise with terrible cell service to physically separate myself from the business. I had to be forced to unplug.

10. I’m more present than ever in enjoying every day. This feels like personal growth.

11. People who say “money isn’t everything” are liars. Managed well, it gives ultimate life flexibility.

12. I should have considered what I wanted to spend my time on before exiting. I had to spend time on that afterward instead.

13. Everyone invests differently. You won’t get one size fits all. Whatever lets you sleep at night while giving you financial freedom = win.

14. Psychology of Money was a game-changer book for me to understand what “wealth” is. Here’s my summary.

15. Your real friends/family don’t care about your wealth.

16. I recognize things I don’t own, but want because they’re flashy, is because of “envy”. Realizing that helps not buy it and move on.

17. Regaining motivation for work is difficult.

18. Spending well is a skill. Not over-spending, but utilizing your wealth to make your life awesome.

19. Legacy is overrated. You won’t be remembered by more than your close family in 50yrs.

20. Want to eat healthy? Keep the house clean? Maintain the yard? Wrap presents? Hire someone. Allow yourself to be happy for more hours of the day.

21. It’s great watching the new CEO execute. I realized was way too ingrained in my business. I should have delegated a lot better.

22. People that know about your sale think it’s amazing and envy you. Be careful of that ego boost.

23. Do you want to buy a house but don’t understand how much you can afford? Use the monthly payment + tax + maintenance as a guide. What’s a comfortable all-in monthly payment is how much house is doable.

24. Privacy is important. Use a service like DeleteMe to wipe your phone number and address off the web.

25. Join a HNW community to learn, complain, ask questions, and thrive from others.

26. Money means nothing if you’re not healthy, overspend there.