38 Life Lessons from 38 Years on the Planet

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Every year I write a list of lessons learned for every year I’ve been on the planet. These are the ones that have stood out to me over the last year.

1. Write Every Day

In his memoir When Breath Becomes Air, Paul Kalanthi he said: “words have a longevity that I don’t.” Two summers ago in a coffee shop, I met an old guy. Every time someone asked him how he was doing he said it was the best day of his life. I was having some of the worst days of my life so I asked him why it was the best day of his life. He told me that at a certain point in your life there’s less time in front of you than there is behind you, so every day was the best day of his life.

I wonder at moments if there is less time in front of me than there is behind me. Age makes you contemplate your own mortality. I know my own words have a longevity that I don’t. So I write every day, and I write something on every birthday.

2. If it matters, put it on your calendar.

Don’t worry about how it will happen. I learned this from my friend Mike Harrington during my time in Colombia (where I happen to be as I write this).

If it’s a trip you want to take, put it on the calendar.

If it’s a goal you have put it on the calendar.

Mike made sure that he puts travel plans for the year on the calendar and he’s doing it much more. I plan to do the same with everything on my list going forward.

3. Have a Reason to Get up in the Morning

In his book The Happiness Equation, Neil Pasricha writes about a concept called ikigai, the Japanese translation for a reason to get up in the morning. The Okinawans live longer than anybody because they have an Ikigai.

When I was 30 I used to stay out until 2am getting drunk, and attempting to recover so I could do it the next night. A friend of mine said “that’s because you never had a reason to get up in the morning, now you want to get up and surf” I also get up to write. Surfing and writing are my ikagai.

Some people believe that retirement, sitting around, and doing nothing will bring great joy to their life. This sounds like hell to me. To remain sharp, I think we have to remain physically and mentally active.

4.Read More Books and fewer Things Online

The best writers I know read tons of books. Julien Smith once told me he didn’t read blogs, only books. He had one of the most popular blogs on the internet before he became the CEO of Breather. Ryan Holiday says books are some of the best investments he’s made in himself. They’ve literally made him richer. I’ve read more books in the last 4 years than all the other years combined. And I’d have to concur with Julien and Ryan.

5. Almost all Change Begins with Changing habits

There’s nothing that’s changed my life as much as the habit of writing 1000 words a day. It’s opened up the world to me. Change your habits and you’ll change your life.

6.Keep Moving Forward

The last two years of my life were some of the most challenging. I had some of my biggest personal and professional failures. The one thing it taught me was to keep going. As AJ Leon’s cuban grandmother says, good news or bad news, you put one foot in front other and keep going.

7. Check the alignment of your compass

In his book The Life and Times of a Remarkable Misfit, my friend AJ Leon recommends people do an exercise: Write down a description of your life in 2 years in 500 words or less. The kicker is you have to send it to someone or post it somewhere, because as he says “you can’t go back on a revolution you’ve already announced. This becomes your signpost, your mountain. Check the alignment of your compass, make sure your headed in the right direction and don’t walk away from the mountain.

8.Draw a line in the sand. Decide who your art is for and who it’s not for.

Sometimes it won’t be for the people who are closest to you. Once you’ve made your peace with that you’ll be free to create without reservation for the people that your art is destined to serve.

9. Keep Exploring, Keep Learning, and Keep Growing

I have an aversion to maps and formulas. That’s partially because no formula I ever followed to the letter led to the outcome it was supposed to. So I have an inherent distrust of anything that supposedly has a guaranteed outcome. I’d rather gamble on uncertainty and the possibility of something significantly better.

Some of the people we stay friends with are committed to an ongoing exploration of who they are and what matters to them. Others get to a point where they feel there are no more layers to unravel. These are the friends I’ve tended not to remain as close to.

I’ve looked at life and myself really as an onion. There’s always another layer to peel, another mask to take off, another costume to ditch. Underneath all that are vulnerability, our truth, and our humanity. To me, the worst possible thing would be to “arrive” with nothing left to explore, no learning left to do and no growing left to do.

10. I’ve become the Antithesis of what my destiny would dictate

At 22, I was fired from my first job at a startup.

At 25, on my actual birthday, I was let go from another job.

At 27, I Ieft my next job, and the one after before I was about to be fired.

Then I applied to business school with an essay that a career counselor described as “this crucible called a career.”

At 30, I didn’t get an offer at the end of my summer internship at Intuit.

At 32, I was let go yet again from one last job.

The definition of insanity is doing the same thing over and over expecting a different result. I stopped trying to find a normal job.

At 38, I’ll be a published author.

This has taught me two things. Your temporary circumstances are not your permanent identity and in the words of Nancy Duarte, I’ve become the antithesis of what my destiny would dictate I’d become.

11.Dare Greatly, Fall Down and Get Back Up

There’s a book on my desk. On the front, it says “if we’re brave often enough we’ll fall.” It’s Brene Brown’s latest book Rising Strong. At 38, I can tell you that I’ve dared greatly on occasion and been crushed. I hated it when it happened. But it gave me the most important chapter of my upcoming book. So for what it’s worth, if you’re in a dark chapter, eventually you’ll find your way back into the light.

12. Pay it Forward

A mentor took a tremendous interest in me. I’m where I am in many ways because of the work he did with me. He felt that working one on one with people would have a more measurable impact than writing a book or blog. That was never lost on me. So I reached out to Rajiv and Martin at Idealemon to ask if I could help them. It’s been one of the most rewarding things I’ve done this whole year.

13. Straight and Narrow Paths Rarely Intersect with Interesting Destinations

After almost 700 interviews you start to notice patterns. You start to wonder what makes people tick and how they got to where they are. If there’s one pattern I’ve found amongst all of them, it’s that they don’t follow straight and narrow or well lit paths.

14. You really can only connect the dots looking back.

A few days after I graduated from college I wrote a 60-page single-spaced story about my college career in 8 days.

The summer after I graduated one of my friends started a web site on which he allowed people to send in essays about their summer. I wrote more than every single person that was on the web site. If he’d seen it at the time, he would have realized he’d created a platform for blogging. I was too busy bitching about the job I hated to see the opportunity that was right in front of my eyes.

During a summer internship when I was a social media intern, the main thing I did was start a blog.

All of that eventually led to getting to write my upcoming book. If you’d told me this is where it would take me in 2001, I would have thought you were insane.

15. Don’t waste too much time on the internet.

We’re more connected than we’ve ever been at any time in history. Yet we’re lonelier and isolated than we’ve ever been as well. The value of face to face interaction with people we care about is priceless. And our need for it is biological. Unplug, leave your phone in the car at dinner, turn it off when you’re with someone. Don’t as my friend Damon Brown says get so caught up in documenting your life that you actually miss it.

16. Find 3 books that You Return to at Least Once a Month

At least once a month, I return to the Life and times of a Remarkable Misfit. Every year I read it and send my friend AJ an email describing my life in two years in 500 words or less. The first time I did this everything on the list was a reality within 6 months. You’d never expect an e-book to light a fire under your ass. But this is so much more than that. It will change your life. The War of Art and Turning Pro by Steven Pressfield are part of my daily routine. They’re like bibles for creative people. Everybody should read these books. Or find 3 books that do the same for you each day.

17. You can Improve with Age

I’m faster, smarter, sharper, and more well read at 38 than I was at 28. I attribute this entirely to having a creative practice. And this isn’t just hokey new age bullshit. Dan Coyle says that when we do something repeatedly we build layers of myelin. And as the myelin layers thicken, info flows through them faster.

I might still fail a standardized test, but there are things from the past that I could know handle with poise and grace. In an interview, Tim Ferriss said there are too many people who he’s seen achieve outsized success in their 40’s and 50’s. I didn’t do much in my 20’s or early 30’s. Most of the significant things I’ll do with my life seems will happen in my late 30’s, 40’s and 50’s.

18. Pure Work Cant’ Be Done When You’re Trying to Prove People Wrong

There have been periods of my life where my work has been entirely driven by the need to prove certain people wrong (ex-bosses, relationships that didn’t work, etc, etc). Nothing great comes from this. In some ways by attempting to prove those people wrong you’re still a prisoner to their expectations. Once you let go of the need to prove all these people wrong, and instead prove the people who believe in you right you’ll move into a place of fluency and flow with your life, your work, and your art.

19. Always Carry a Notebook/Take Notes

I never leave home without a Moleskine. I learned this from AJ Leon and Sarah Kathleen Peck. The seeds for nearly everything I’ve done in the last 7 years are in my notebooks. Blank pages can serve as fertile soil to give birth to your best ideas.

20. Ditch the Checklist of Dreams You Pretend Not to Have

In our heads, we all have a list of things that need to happen before we’re content and satisfied. I’d be lying if I told you I don’t have a checklist of dreams I pretend not to have.

  • Fall in love
  • Have kids
  • Teach those kids how to surf

But if the checklist of dreams you pretend not to have is ruling your life, then you’re missing out on the dreams that are coming true in the present moment.

21. If you don’t care about what you do, it will only take you so far

If what you’re working on is merely the means to an end, the path to some sort of external accolade, it will only take you so far. Caring about what you do, loving it, is what makes it possible to show up on the days you don’t feel like showing up and sticking with it on the days you want to quit.

22. Don’t Live According to a Deferred Life Plan

In his book, The Monk and the Riddle, Randy Komisar talks about what is known as the deferred life plan. In other words putting off the life you want to live until all sorts of things have happened. I have jokingly said I think Indians are on a deferred life plan because they believe in reincarnation. With the skeletons in my closet, I might be reincarnated as a cockroach so I’m not taking any chances and putting all my money on this life.

23.Your work has to be about something greater than yourself.

When I met my editor at Penguin for the first time, I didn’t ask about how to sell a lot of copies, I didn’t ask about best-seller lists. I asked her how my book could be the some of the best work she’s done in her life? Whenever Brian Koehn and I take on a project, we want to make sure that people we work with have done some of the best work of their life. Lauren Rains and Marius Dorian, despite our neurotic standards, will probably attest to this. At a certain point, I realized there are more people than me impacted by my actions.

  • My editor who bet on me
  • My partners Derek Wyatt and Brian who have put tons of time, energy and effort into the future of our brand
  • My agent

And of course, the people who I hope we have an immeasurable impact on, those who read our book. When your work is about something greater than yourself, it makes it much easier to get up and do it each day.

24. Don’t compromise values and standards for short term profit.

The cost of doing so is too high in the long run. When the formulas, methods and the systems of the internet convince you that you can get rich and live the dream too, it’s tempting to create things out of alignment with your values, things you didn’t genuinely want to see exist in the world. It’s a lesson I’ve learned from mentoring Rajiv Nathan and Martin McGovern who have been willing to stick to their guns in service of finding the deeper meaning in their work.

25. Sometimes you get what you want by giving up the desire for it.

But there’s a difference between giving up on the thing and giving up the desire for it. At 38, I’m starting to think that this is the case with love, relationships and everything else we’re willing to give up the desire for. Once you decide that you’re ok without all of the things you think you need or want you star to get all of them. It’s one of the odd paradoxes of the universe.

The very nature of “want” makes it feel like life is incomplete in some way, and puts us into a space of scarcity.

  • I want my kids to be married, have grandkids, and have a house in the suburbs
  • I want a million dollars in the bank
  • I want to be famous, rich, insert societally approved badge of honor of your choosing

Perhaps if you stopped wanting you would get all of it. Or if you didn’t get all of it, at least, you’d have some peace of mind and the mental energy to commit to something more worthwhile than all the things you feel you don’t have or need to be ok. Most of what we think we want, we don’t actually need.

26. Freaking out doesn’t alter the outcome of anything

Nobody’s life has ever ended because they were late to dinner, missed a flight, or got stuck in traffic. But people freak out about these things all the time. That’s a lot of energy wasted that could be directed towards something that actually alters the outcome.

27. Don’t worry too much about the future. Don’t dwell too much on the past.

It’s easier said than done. But both of these things have caused me nothing but anxiety. There’s a chapter in Ryan Holiday’s book The Obstacle is the Way about the process. Whatever it is you’re attempting to achieve I would recommend you read this chapter as a daily reminder. It’s easy to get caught up in the end, the goal, the metric you’re trying to hit. But the process, the steps you need to take today is what you control. I have some big goals for my upcoming book, but after reading about the process I’ve shifted my focus from the outcome to the process.

28. Give it a little bit more time before you quit.

Some people quit in the face of adversity. I almost did. If you’re going to quit, give it one more day, one more month, one more year. It could make all the difference.

29. Don’t be Afraid to Pull the Plug

If the downside of a business failure is that it could put you out of business, even if it means some relationships that might suffer, don’t give in. One of the best pieces of advice I ever got was “you can recover from disappointing some people. It’s going to be a lot harder to recover from being 50,000 dollars in debt.” Sometimes you just have to pull the plug.

30. One word can change your life.

For me that word has been unmistakable. It led to the name of our company, my book, and more things than I can possibly measure. It’s my ethos. For my friend AJ that word has been misfit. I think every one of us might have a word that can shape our destiny, leading us to places far greater than anything we can imagine in the moment.

31. Come up with your own definition of happiness

Everybody will tell you what they think it means for you to live a complete, whole and happy life. It’s actually really hard not to listen to them. But the sooner you get clear on what your own definition of happiness and success is the better off you’ll be. Don’t let some internet celebrity tell you what happiness or success is, don’t let it be determined by something you read in a book. Determine it for yourself. Strangely my entire motivation for everything I’ve done and worked on in the last few years comes down to something incredibly simple.

Nothing puts a smile on my face like dropping into a perfect wave.

32. Quality Trumps Quantity when it Comes to Friends

When I was younger I used to dream about the day that I would have some massive birthday blow out with fireworks, and everything else in between. I still want to have a birthday party with fireworks. But I’d rather spend it with a few close friends than a thousand acquaintances. As you get older, close friends become even more valuable. They tend to be the ones who are there when we’re up or when we’re down. They give us hope when we’re hopeless, kick our ass when we want to quit. We’re eternally indebted to them, and yet can never repay the gift they’ve given. That’s a beautiful and powerful thing.

33. People are in our lives for a reason, a season or a lifetime.

The people in our lives will give us sentences, paragraphs, passages, and chapters for our stories. Choose the ones that you want to be there for a lifetime wisely.

34. Ride Waves, Mountains do Something that Involves a Board Under Your Feet

The only other thing that’s changed my life as much as 1000 words is surfing., And of course surfing was the gateway drug to snowboarding, skateboarding and anything else that involves a board. Apparently, I have a pathological need to tie boards to my feet and go at high speeds. Surfing is like going to a church, a gym, and a bar all in one activity. It meets my spiritual, physical and social needs. Action sports teach you about risk, life, and flow.

35.If you’re going to challenge the status quo you will be misunderstood.

If you defend it you won’t. But you can’t have it both ways.

36. Celebrate Small Wins

This is something I’ve learned from my business partner In the pursuit of big goals we often overlook small wins.

  • We don’t celebrate hitting a word count, only getting a book deal
  • We don’t celebrate a new feature on the app, only getting funded or reaching a million users.

We constantly overlook small wins fueling our dissatisfaction. But it’s small wins that result in moment and progress.

37. Value your Time

As you get older, the opportunity cost of doing something you can’t stand becomes even greater. That’s because you have so much less time. The paradox is that most people do less risky things, take less chances, and take their time for granted even more as they get older. Try to avoid the paradox.

38. If you live in San Francisco, Read Street Signs Carefully

When I lived in San Francisco, I donated so much the Department of Parking and Traffic that I have been tempted to write them a letter about erecting a statue in my honor. But I’m sure there that mine would not be the only statue of an SF local. This is a more eloquent of saying I got a shitload of parking tickets. A disregard for authority is not particularly useful when it comes parking tickets. So read the street signs.

These are just a few of the things I’ve learned from 38 years on the planet.

I’m the host and founder of The Unmistakable Creative Podcast. Every Sunday we share the most unmistakable parts of the internet that we have discovered in The Sunday Quiver. Receive our next issue by signing up here