I recently had the opportunity to celebrate my 50th birthday with my closest friends and family.

There’s something about turning 50 that makes you pause. You finally have enough distance to see the patterns behind you. At some point, you stop chasing the next win long enough to ask, What worked? What mattered? What was noise?

Since I’m feeling a little sentimental and reflective, I thought I would jot down 50 lessons I’ve learned about life and business. If you want to skip straight to the list, you can click here.

I’ve learned that money doesn’t buy happiness, but it does buy convenience (1). Convenience can change your life. It gives you time, options, and margin. But it’s just convenience, Money is validation (2). It’s confirmation that the people who doubted you were wrong.

But money only shows up when you’re selling the right thing. You’ll never become rich selling the wrong product (3). I talk to people all the time who want to make a million dollars, but they’re selling a low-margin product that very few people need or want. They think that if they work harder, they will eventually make a lot of money. You will never make a $1 million selling a bad product. 

Growing up, I always heard that “it was lonely at the top”, but it doesn’t have to be lonely at the top (4). The right people change everything. In fact, you’re only as good as the people around you (5). And if you do it right and treat people right, many of the people you hire to work with you become friends.

When you’re young, you constantly stress about money. You think if you don’t figure it out now, you never will. But the truth is, the money will come if you’re patient and willing to learn (6). You have to be patient, and more importantly, you have to build your network (7), because your future business opportunities will come from the people whose names are in your cellphone (8). 

That means you’re going to have to get out of your comfort zone and actually talk to people. Not email, or text, or leave a voicemail, but actually talk over drinks. First impressions matter (9). So make a good one. And people help people they like (10), so be kind. Treat people the right way. It will come back to you. 

But most people don’t want to leave their house. They don’t want to network. They’d rather use social media. I’m old school, I know, but you don’t need social media to build a real business (11). It’s mostly a distraction. In all my years, I never had social media. Hell, I barely used email. It wasn’t until after I sold my business that I created some accounts to try to help people succeed.

Ignore people who say, “What got you here won’t get you there.” (12). Your core strengths are usually the same ones that carry you forward. Most people abandon them out of boredom or because someone sold them a shiny new strategy.

You’ll only scale as big as your systems allow (13). And systems—not effort—are what separate six figures from seven. The jump from $100,000 to $1 million isn’t about working harder; it’s about changing your structure (14).

At some point, you have to take risks (15). Real ones. You can’t play it safe forever. You’ll tell yourself you’re being responsible to wait, but you’re just scared.  Some risks will work. Some won’t. Eventually, you realize every failure was preparation (16). I can trace almost everything I do well today back to something that didn’t work years ago. Failure won’t kill you (17). But learn from your mistakes. Even better, you need to learn from someone else’s mistakes. That’s why you need a mentor or coach (18).

When I talk to younger people getting into business, I like to tell them a few things: First, you’re not behind (19). The internet makes it look like you have to conquer the world by the time you’re 25. You don’t. But don’t confuse potential with progress (20). You haven’t made a sale or cashed a check yet. Great things are in store, but have some humility. You don’t know what you don’t know.

If you commit to a few habits early in your career, you will climb and eventually make more money than you’re stressing about right now. Here are the habits: Solve problems (21), Take the blame (22), always tell the truth (23), and finish the job (24). Most people do the opposite: they create problems, take the credit, bend the truth, and leave things unfinished. Just these 4 habits will set you apart from almost everyone in your industry. Don’t underestimate the power of just showing up (25). To the office, to the gym, to drinks after work, to conferences and workshops, and every other opportunity you’re given. 

As you grow, you will outgrow people (26). That part hurts more than anyone prepares you for. You think everyone will be happy for your success, but they won’t. Criticism from people who know you hurts worse than criticism from strangers (27). They both sting, but when people you’ve helped the most talk bad about you, it’s personal. They’re usually mad because they wanted money and you said, “No.” Once you make a lot of money, everyone will assume you will give them some (28). No one prepares you for that.

You won’t be criticized by people who accomplish more than you (29). They’re too busy working, or they’re retired and sitting on a beach, not thinking about you. Critics hang out in comment sections all day because they have nothing else to do. They love to talk, but talk is cheap (30). 

Speaking of talk: Learn from doers, not talkers (31). There are lots of people who promise they can help you, but before you pay them, ask them what they have done. Not what they think, or what they’re going to do, but what they’ve done. As a general rule, never hire someone to coach you who’s made less money than you (32).

It’s hard to tell, because most people you think are rich aren’t (33). A recent report found that the average content creator online earns around $15,000 per year. But the illusion works. Everyone looks rich. Everyone looks like they’ve figured it out. They haven’t. 

I’m not saying how you present yourself doesn’t matter. It does. How you show up matters more than your résumé (34). You’ll never be seen as successful if you don’t see yourself that way first. People decide your value in split seconds, before they ever see your results. So spend some money making yourself look good. As Dieon Sanders used to say, “If you look good, you feel good. If you feel good, you play good. If you play good, they pay good.”

When the opportunity finally does come, go all-in. The idea of balance is bullshit (35). What most people call balance isn’t actually balance at all. If you work 40 hours per week, that leaves 128 hours for something else. Does that sound balanced? There will be seasons when your career demands more of you (36)—and that’s okay. What’s not okay is missing the moment. 

When you start making real money, keep your expenses down (37). High income with high expenses is stress. The more money you have to make to maintain your life story, the more trapped you will feel. And feeling trapped sucks (38). Keeping your expenses down, keeps your options open.

Success doesn’t simplify life (39). The more you earn, the more there is to manage. The more people you lead, the more they depend on you. The rewards are higher, but so are the expectations.But don’t whine. Pressure is a privilege (40). You begged God for this. 

Don’t let success go to your head. Every millionaire got lucky (41). Of course we work hard, I’m not saying it’s only luck, I’m saying you don’t control nearly as much as you think. Fate is a powerful thing. But you won’t want to admit it. You’ll want to take credit for everything. Don’t do that. Ego is the enemy (42). Read Ryan Holiday’s book. Don’t confuse a specific talent with a false sense of self-belief. Just because you are great at one thing doesn’t mean you’re great at everything (43). It’s why professional athletes try to start record labels, and rock stars try to open restaurants—they believe their instincts are infallible. They’re not.

It’s one thing to know you got lucky in life, but it’s another thing for someone else to call you lucky. They’re implying you didn’t work hard for what you’ve earned. They’ll try to make you feel like you need to apologize for your success. Don’t ever apologize for your success (44). Life isn’t fair (45). You made the most of your opportunities. You have nothing to apologize for. 

If you screw up, and it all comes crashing down, that’s ok. Endings create new beginnings (46). Nothing lasts forever. You’ll bounce back. 

So work and play hard (47). What’s the point of making a lot of money if you can’t enjoy it? It’s fun to buy toys, but spend money on experiences (48). Growing up, my family was too poor to travel, so when I made a few million bucks, I started traveling around the world with the people I love. It’s the best money I’ve spent, because experiences make memories.

That’s probably what I’ve learned the most. Relationships are the most valuable thing in life (49). People will tell you not to work with friends. That’s good advice, I guess, but I think if you do it right, you can make it work, and it’s so rewarding because helping other people make money is more rewarding than making it yourself (50). 

Here’s the list:

1. Money doesn’t buy happiness, but it does buy convenience
2. Money is validation
3. You’ll never become rich selling the wrong product
4. It doesn’t have to be lonely at the top
5. You’re only as good as the people around you
6. The money will come if you’re patient and willing to learn
7. Build your network early
8. Your future opportunities come from your relationships
9. First impressions matter
10. People help people they like
11. You don’t need social media to build a real business
12. What got you here *will* get you there
13. You’ll only scale as big as your systems allow
14. The jump from $100,000 to $1 million is about structure, not effort
15. At some point, you have to take real risks
16. Every failure is preparation
17. Failure won’t kill you
18. You need a mentor or coach
19. You’re not behind
20. Don’t confuse potential with progress
21. Solve problems
22. Take the blame
23. Always tell the truth
24. Finish the job
25. Don’t underestimate just showing up
26. When you grow, you will outgrow people
27. Criticism from people you know hurts the most
28. Once you have money, people will assume you owe them
29. You’ll never be criticized by someone accomplishing more than you
30. Talk is cheap
31. Learn from doers, not talkers
32. Never hire someone to coach you who’s made less money than you
33. Most people who look rich aren’t
34. How you show up matters more than your résumé
35. Balance is bullshit
36. There are seasons when your career must demand more of you
37. Keep your expenses down
38. Feeling trapped is one of the worst feelings in life
39. Success doesn’t simplify life
40. Pressure is a privilege
41. Every millionaire got lucky
42. Ego is the enemy
43. Being great at one thing doesn’t make you great at everything
44. Never apologize for your success
45. Life isn’t fair
46. Endings create new beginnings
47. Work hard and play hard
48. Buy experiences over things
49. Relationships are the most valuable asset in life
50. Helping other people make money is more rewarding than making money yourself