April 11

41 Things I Almost Know for Sure

Truth is subjective. What’s true for one person may not be for another. After 41 years, I’ve learned the only constant changes, and the only certainty is uncertainty. In no particular order, these are the 41 things I almost know for sure.

1. Nothing is more precious than the time we have left with the people who matter most to us. We take it for granted that the people who love us unconditionally will always be a phone call away. Families are unforgivingly complex, messy, and imperfect. But if you’re lucky enough to be close to them and have time to spend with them, don’t ever take it for granted.

2. Creative success is a blessing and a curse. Before you have any commercial success as a creative, you have nothing to lose. Nobody has any expectations of you, readers, agents, editors or publishers. After you’re successful, you have something to lose and something to protect. But you have to keep playing the infinite game of creativity as if you have nothing to lose. That was what made you successful in the first place.

3. When you expect nothing, everything comes to you. Expectations are an attempt to control the uncontrollable. This is the cause of all of our suffering. This is true for our personal and professional lives. At Phillip McKernan’s retreat, he said of relationships, “How can you expect so much from someone you’ve never met?” But if you expect nothing, the good things will delight you and the disappointments won’t phase you as much.

4.There’s an eternal gap between who we are and who we want to be. Unless you decide you’re done with life, or don’t want to experience more, you’ll always be living in this gap.

5. Nothing you accomplish will permanently alter your self-image. Hitting the NY Times Best-Seller list won’t make you immune to doubt as a writer. Hooking up with the hottest girl in school won’t lead to everlasting confidence. There’s only so long you can keep solving internal problems with external solutions. Eventually you’ll have to deal with your wounds.

6. How you measure your life will have a profound impact on your happiness and well being. The number of followers you had, notches on your bed post, or the money in your bank account won’t be on your tombstone. In your eulogy, people will speak of your character. How kind were you? How did you make them feel?

7. The options in front of you can blind you to the possibilities that surround you. If you go to a famous college, this is more likely because the options in front of you get narrower. You choose from 100’s of majors, which lead to about 10 different career paths. But if you stop looking solely at the options in front of you, you’ll see a thousand different paths to your destination.

8. Dreams come true in unexpected ways. I applied to business school in the hopes of working in media and entertainment. I wanted to go to NYU Stern, work in television, and pick what goes on the air. And they made the right decision to turn me down, given how ego-centric my application was. Ten years later, not only do I get to choose what goes on the air, I get to create it. Deep down, that’s what I wanted the most.

9. Every Indian mother is the best cook in the world. Food is the tie that binds Indian families together. All of our socializing centers around food. If an Indian person invites you to their home and their mother offers you a home-cooked meal, don’t ever turn it down. It will be one of the best meals of your life.

10. What you create for an audience of one is much more likely to reach an audience of millions. Despite writing a book where this was the primary message, it was something I had to learn from experience. When I finally embraced it, my book sold 40-50 copies every week and outsold my previous book. When I started working on my self-published book, The Scenic Route, I found that joy again. You can read the whole thing for free here.

11. Being an anonymous critic is the path of least resistance, but being a prolific creator is the path of most reward. It’s easy to sit behind a keyboard and offer anonymous feedback in iTunes reviews, book reviews, and more. Putting your work out into the world requires you to put something on the line, try something that might not work, and take the good with the bad.

12. Everything you’re seeking from other people is already within you. We seek love, validation and approval from the world around us. We seek it from parents, peers, friends, and romantic partners. When you give these things to yourself, that’s when you’ll get them from others.

13. Presence is the antidote to comparison. When you’re completely absorbed in what you’re doing, it’s almost impossible to compare. The joy of being in a deep state of flow mitigates the pain of comparison.

14. Family is a good way of keeping your ego in check when you become successful in any capacity. They know who you are underneath all the layers that have become your identity as an adult.

15. Every now and then, ask yourself, “If this was the last year of your life, would you be happy with how you’ve lived?” In the years when the answer to that question was no, it lit a fire under my ass. Those are the years in which I’ve done some of my best creative work.

16. If you don’t base your goals on lived experiences, they’ll never satisfy you. They might even make you miserable. Don’t just blindly follow a passion. Pay attention to what you find engaging. Otherwise, you’ll spend years chasing the wrong dream. You’ll arrive at your destination and realize that it doesn’t make you happy.

17. Everything you fight has power over you, everything you accept doesn’t. For months, I was dreading the idea of attending my sister’s wedding without a date. By the time December rolled around, I realized this was inevitable. When I accepted it, it transformed into the opportunity of a lifetime.

Every time I went to a wedding and the Indian aunties would ask when I was getting married, I’d get irritated. But this time, instead of getting annoyed, I put a slide with my phone number on screen during the speech I gave. I encouraged them to text profiles, pictures and relevant information about potential suitors. I told them I’d expect a full report on their progress by the end of the week.

My speech was a hit. My brother in law’s friend invited me to speak to his MBA Students. I was able to visit the town I grew up in after being away for almost 30 years. As for the aunties, they’re the worst unpaid employees in the world.

18. If you quit social media for 30 days, you’ll be happier. You won’t compare your insides to other people’s outsides. You won’t mix up the trailer for someone’s life with the movie. And you’ll be more engaged with the world around you.

19. It’s never too late for your career to take off. By the time I was 30, I had a resume of failures that looked like a rap sheet. Now, I get hired to speak at companies where I could probably never get a job.

20. When it comes to work, choose more responsibility over more money. It will be worth a lot more money in the long run. You’ll develop the skill that will increase your earning potential. I’ve probably said this in dozens of other articles because it’s worth repeating.

21. The most important relationship in your life is the one you have with yourself. It’s one of the 3 pillars of a meaningful life, and the foundation upon which everything else is built.

22. There’s a difference between having money and being wealthy.

  • If you have a lot of money, but don’t have any friends, you’re not wealthy.
  • If you have a lot of money, but hate your work, you’re not wealthy.
  • If you’re not grateful for anything, you’re not wealthy.

As Tim Ferriss once said to me, “What makes someone truly wealthy is present-state appreciation for what you already have.” If you don’t appreciate what you have now, you’ll never appreciate what you get later.

23. Waiting for permission is a time-wasting fool’s errand. We have near limitless access to tools, resources and distribution channels. As Alexis Ohanian says, “The future will be created without their permission.”

24. The only person worth comparing yourself to is the previous version of yourself. It’s tempting to compare your life to the highlight reels of other people’s lives. Don’t confuse the trailer with the movie.

25. Reality is nothing more than a series of collective agreements from a large group of people. When you start to challenge those agreements, reality becomes malleable. You become the author of your story, and the architect of your reality.

26. Everything worth doing will take longer than you think. Parts of it will suck. That’s why it helps to care deeply about what you’re working on. You’ll be less tempted to quit when you hit a dip.

27. You will have to give something up to get what you want. Everything in life has an opportunity cost. If a VC invests in your startup, you give up the freedom to manage a business any way you want. If you have kids or start a family, you might have to give up the freedom to do what you want when you want.

28, Everybody has a story worth telling. A few days before my sister’s wedding, I decided to interview members of my family. If you ask people in your family about their lives, you’ll learn things about them that you never knew. My cousin shared a hilarious story about how she met her husband (which you can see below).

About a week ago, I finally sat down with my mother and interviewed her. It was the most honest conversation we’ve had in the last 40 years. I asked her what made her happier than anything in the world. She said it was seeing her kids settled. So I asked her if she was unhappy that I wasn’t married yet. The answer I got surprised me.

It wasn’t about other people’s expectations or putting pressure on me. Her primary concern was who would be there to take care of me when she and my dad were gone. As long as they were here, I could always come home for dinner or spend a weekend with them. We both shed a few tears together. And I finally saw it was with the best of intentions that she wanted me to meet someone. That conversation will alter the trajectory of the time we have left with each other.

29. Find a habit, hobby, ritual or routine. Do it every day. It will change your life. Writing 1,000 words changed mine.

30. If something is worth doing, it will be harder than you think. Paul Graham says to create a million dollars in wealth, you have to endure a million dollars worth of pain.

31. Progress is rarely linear. It can seem as if you’re going nowhere. For years, people questioned my sanity and my career choices. One of my relatives told my cousin that my life was a waste of my education. So I crossed her off the guest list for the wedding I haven’t planned yet.

32. There are some paradoxes to time that you have to get your head around. First, it’s a limited non-renewable resource. But you also need infinite patience for the results you want to create. You might have to start today for a dream that will come true 10 years from now.

33. The wide range of human emotions gives us colors to paint the masterpieces of our lives. You’re going to experience love and heartbreak, pain and joy, happiness and sadness. There will be peaks and valleys, successes and failures. Whether you paint or cry is up to you.

34. Discomfort is the price of admission for a meaningful life.

It’s uncomfortable when people question your sanity for leaving a stable job.

It’s uncomfortable to suck at something and put your work out for public consumption.

You can pay the price of admission or give up a meaningful life.

35. Stop waiting for permission from a publisher to write your book, a label to record your album, or a VC to launch your startup. You’ll get it from them when you give it to yourself.

36. At some point in your life, you will have to take a risk where the outcome is unknown. That moment will often be the differentiator between what you’re able to do and what you’re made to do.

37. Gifts from the universe don’t usually come wrapped in pretty packages. They come disguised as punches to the face or blows to the head.

  • I got rejected from every business school that I applied to.
  • I didn’t get a job offer after my summer internship at Intuit.
  • I graduated into two recessions.

If it hadn’t been for these gifts from the universe, I wouldn’t be an author and speaker.

38. At some point in your life, you will fail at something you care about. Your startup will go out of business. You won’t sell enough tickets to an event. Your art won’t resonate with your audience. You will put your heart on the line and someone will break it. There’s no way to avoid this. It’s necessary to live what Pam Slim calls a “full-color full contact life”.

However, our failures are often the precursor to our success. My first few blogs didn’t reach many readers. I learned from each one and applied what I learned to my next endeavor.

39. There’s no such thing as the perfect time. You can keep putting off the dream you want to pursue. You wait until you’ve saved enough money, your kids are in college, or all your ducks are in a row. But that becomes an excuse to keep delaying your dream. Tomorrow is not a guarantee for any of us. So you might as well start today. Take one step.

Besides, ducks are rarely in a row. Throw a piece of bread into a lake and that becomes clear.

40. Security is an illusion. People saw fortunes evaporate during the financial crisis of 2008. Fortune 500 companies have gone out of business. The security illusion keeps people working jobs they hate. It keeps them buying shit they don’t need, and trying to impress people they don’t like.

41. Maybe you’re not a gigantic screw up who is 10 years behind on your most important life goals. Maybe you’re taking the scenic route.


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