29 Things I Learned at 29

Lessons From A Year Of Mastery

Four years ago, my friend Dev Basu inspired me to compile a list of lessons learned during 365-day rotations around the sun. My anthology includes orbits numbers 26, 27, and 28. This is 29.


1. If you truly care about it, put it in your calendar.

Budgets are reflections of priorities, and calendars are budgets of your most precious resource: time. What’s not in your calendar likely won’t happen.

2. Emulate the process, not the end result.

Don’t try to be Kanye West unless you’re prepared to make five beats a day for three summers. There’s no substitute for the work that’s required to be great.

3. Stop wishing — either work harder, or want less.

Instead of wishing for success, work harder to make it likely. And if you aren’t willing to work harder, then manage your expectations about success.

4. If you can’t handle stress, then you won’t manage success.

The experience of modern life isn’t getting any easier. Accept stress as a constant, then build the resilience necessary to withstand it (and adapt to it).

5. The road to mastery is lined with individual bricks.

Before you can build monuments, become really good at laying individual bricks. Kobe Bryant became Black Mamba after practicing 400 shots per day.

6. Always care more about the outcome than the outputs.

Remove your ego from the day-to-day. Keep your vision locked on the end goal — your outputs will automatically rearrange to realize it.

7. Breakthrough success requires obsession.

If your end goal isn’t always on your mind, be honest with yourself: you probably don’t want it badly enough. Reverse-engineer it into habits.

8. Create your own time zone.

Get out of other peoples’ time zones. You’ll reach your milestones when you reach them. You’re not early. You’re not late. You’re on time.

9. Before you quit, sleep on it.

If you feel like quitting, it means you’re doing something right; the temptation to quit is greatest just before you’re about to succeed.

10. Failure is a temporary delay between you and victory.

Don’t let failure paralyze you — reframe the experience as just an extra step towards success, and then get back to work.

11. If you do enough experiments, the odds are in your favour.

More experiments means more lessons. And the more lessons you learn, the more your success will curve exponential rather than linear.

12. Death is the ultimate productivity hack.

Go ahead, write your eulogy. Get real about your mortality. Nothing will get you going like the sense of urgency created by the awareness of death.

13. Triple-down on your strengths.

Stop overcompensating for your weaknesses. Instead, create an unfair advantage for yourself by focusing on the things that you’re really good at.

14. Do fewer things really, really well.

Your best work deserves your full attention. Multitasking overloads your system with inputs and wears away your decision-making potential.

15. Practice non-zero days.

On your days off, don’t lose mental grip on your goals. Keep your goals at the top of your mind, but not so much so as to defeat the purpose of a rest day.

16. Find your 4 AM.

The extra mile is never crowded. Live a few years of your life like nobody else will, so that you can live the rest of your life like nobody else can.

17. You’re not busy, you’re disorganized.

If can’t find the time to do the things that you want to do, then it’s either not a big enough priority or you’re just not managing your time well enough.

18. Comfort is the gateway drug to complacency.

If you feel like you’ve succeeded, reset your goals; if you’re the smartest or most capable person in the room, you’re in the wrong room.

19. Stop competing with your contemporaries.

Outperforming your peers will only get you so far. Aim higher by emulating people who have extended your runway of possibilities.

20. Don’t confuse friendliness for friendship.

Keep circumstantial friends safely at arms-length. True friendship can only occur when both people don’t need anything from each other.

21. If don’t like change, you’ll like failure even less.

Nothing changes if nothing changes. If you do what you’ve always done, you’ll get what you’ve always got. Never lose your beginner’s mindset.

22. Don’t wait for problems to become priorities.

People tend wait for a problem to become a priority before addressing it. Your priority should be to never let things become a problem in the first place.

23. Do things, tell people.

Storytelling is the fundamental unit of human understanding, and we live in the golden age of storytelling. Tell your story, or someone else will.

24. Don’t start a business, solve a problem.

You are the best person in the world to solve a specific problem. Discover it, and then build a business around it.

25. Master your mornings.

Within the first two hours of waking up, get the most stressful task of the day out of the way. The rest of your day will be a walk in the park.

26. Great leaders are great followers.

Have the humility to follow the lead of someone more smarter and more capable. Being a contributor can be just as valuable as being a leader.

27. Pursue your own definition of “enough.”

Be the best version of yourself, instead of a mediocre version of what others want you to be. Don’t let others determine what success looks like for you.

28. Books are life’s cheat codes.

Fools learn from their own experience. The wise learns from the experience of others. Don’t make more reading a wish, make it a habit.

29. Don’t ship it unless you’re willing to put your name on it.

Make sure it’s good enough for you before you put it out into the world. You can’t expect anyone else to bet on you if you can’t bet on yourself.