I’d been dreading this day for months. Anytime I thought about it, it made me anxious. Every year for eight years I’ve written something. It’s become my birthday ritual, a lesson for every year. But contemplating 40, I thought maybe I wouldn’t answer the phone, write anything, or even talk to anybody. I was just going to lie in bed and wake up the next day as if it had never happened.
Is this my life? What business do I have telling anybody anything and calling it wisdom? But then something happened, a moment that woke me up… and led me to these 40 things I wish I knew about life, love, and work when I was younger.
1. I was visiting my friend Joseph Logan for a snowboard trip in Colorado. After a few warm-up runs, he said: “it’s graduation time.” In my mind, black diamonds were impossible, something I’d never be skilled enough to do because I was too old.
As I stood at the top of the Starfire run at Keystone, my heart raced with anticipation. I strapped in my boots, took out my phone, opened Spotify and started Walking on Sunshine. I remember the advice Steven Kotler gave me years ago “the key to flow on a snowboard is speed or fresh powder.” There’s nothing I wanted more in that moment than to be in the zone in flow, hauling ass down a black diamond. In about 3 minutes, going roughly 30 miles an hour, I went from being the guy who couldn’t get down a bunny slope in college without falling to being a 40-year-old black diamond snowboarder.
The impossible became possible, and my whole story about what it meant to be 40 changed. The first time I ever saw a black diamond at a ski resort, I turned to the friend I was with and said, “There’s no way in hell I’m ever going up there, those people look like ants from here.” I wish I had known that age is an imagined limitation that keeps us playing so much smaller than we’re capable of playing.
2. Joseph is 48 years old. You’d never know by looking at him. He runs ultra endurance marathons and skis black diamonds, sometimes up to speeds of 65 miles an hour. Sometimes he’ll even run 7 miles after skiing all day. He coaches startup founders who are doing amazing things like building supersonic jets, and he’s got the most adorable kids. If there’s one thing I’ve learned from being around him, it’s just how amazing life can continue to become with age. I wish I’d known that it’s better to arrive late than never at all.
3. In high school, I made all-state band three years in a row, was a straight A-student and got accepted to UC-Berkeley. After college, I tried desperately to find the job that would be most impressive on my resume or give me the highest paycheck. During my MBA program at Pepperdine, I had the highest paying internship in my class. Ten years later I got a book deal with a publisher. And now I’m starting to see that I’ve spent my whole life seeking my self-worth through accomplishments and accolades. I wish I’d known that I was worthy of love and belonging regardless of what I accomplished.
4. For a good amount of my life, I’ve taken things harder than most people do. A romantic rejection would derail me for weeks or months. An unexpected bill would send me into a state of panic and anxiety. A professional failure would feel like it was my identity rather than a circumstance. But it wasn’t until I experienced all of these things in a week and crashed so hard I couldn’t get out of bed in the morning, that I realized I’d been dealing with low-grade depression for most of my adult life. For the longest time, I thought it was a major flaw. Then I learned that some of the people who I looked up to like Jerry Colonna, and many successful founders had dealt with depression as well. I wish I had known that it was ok to ask for help, and that therapy is an incredible gift to yourself.
5. For most of my life I’ve been in a damn hurry to finish school, get a job, become successful, meet the woman of my dreams, and cross off every checkbox in society’s life plan. We’re obsessed with doing more of everything and doing it faster. And I’m saying this as someone who writes about productivity. The results of my impatience: speeding tickets, car accidents, and saying things I’d never be able to take back. I wish I’d known that impatience paradoxically makes everything in life take longer.
6. We all have goals, dreams, and desires. We want to get the book deal, fall in love, or sell our startup. So often these things define us. We attempt to derive our self-worth from projects, people, and accolades. But when our expectations aren’t met, the book doesn’t sell enough copies, the startup goes bust, or we get dumped our self-worth gets shattered. I wish I’d known that basing your self-worth on one thing is a bit like playing Russian roulette with your mental health.
A willingness to forgive reflects a desire to take care of ourselves. We all know what it feels like to hold on to hatred and blame. It’s the worst kind of poison; it clouds everything. The more we resist the possibility of forgiveness, the more we invite the probability of unhappiness. We allow for a toxic reality that only forgiveness can clear. – Scott Stabile
7. For years I resented people: my roommate in college who I had a falling out with, the boss who threw me under the bus on his way out the door, and the girl who more or less told me I didn’t have enough money to date someone like her. But the person who suffers the most from resentment is you. I wish I’d known that forgiveness sets you free. It keeps you from hanging onto what was never meant to be so you can live up to what was destined to be.
8. Because of my work at The Unmistakable Creative Podcast, I’ve had the opportunity to talk to some of the most accomplished people in the world.
But even after standing on stage and writing books, I had this belief that “I’m not one of them. I just tell their stories.” I didn’t see them as peers. I remember the first time I shared a stage with my friend Pam Slim in Fargo. I wondered what I was doing there. She wrote books; I wrote FB status updates that I likened to career suicide. But if there’s one thing I try to do in asking the questions I do, it’s humanizing the people I interview. This is why I ask about their parents, their lives in high school, first crushes. Even masters of the universe have experiences that are universally relatable. I wish I had known that regardless of our accomplishments, we’re all human, fallible and breakable.
9. For a long time, I purposely left things out of my writing because I was afraid of what people would think or say. It was only after I started writing honestly that I started to develop my voice as a writer. Anne Lammot famously said, “Write down all things you swore you’d never tell anybody.” I wish I’d known that vulnerability, authenticity, and truth lead to a connection between the person who writes and the one who reads.
10. A couple of years ago, I was getting my afternoon coffee, and this guy walked into the coffee shop. Every time somebody asked him how he was doing, he said, “It’s the best day of my life.” I was having one of the worst days of my life. So I walked over to him and asked him why he kept telling everybody it was the best day of his life. You might think that he’d just had grandkids, his daughter got married or he’d become a millionaire. But the simplicity of his answer is something that I’ve never forgotten. He said, “There’s a certain point in life when you realize that there’s’ far less to look forward to than there is to look back on. So every day going forward is the best day of my life.” I wish I’d known that big moments make up the smallest fraction of our lives. The small ones make up the majority of it. If all we’re doing is waiting for the really big moments, we don’t value and appreciate the small ones.
11. Sometimes unexpected things happen over the course of a life, the loss of a parent earlier than we imagined, divorces, bankruptcies, recessions, and so many other things that are out of our control. Our natural tendency is to fight and resist that which we have no control over. I wish I’d known that sometimes life doesn’t go according to plan and it ends up being the best thing that ever happened to you.
12. We tend to look for finish lines. The moment when we have it all: the money, the lover, the toys, the cars. But happiness and fulfillment is a practice, not a destination. We think that there will be a moment in life when the puzzle is complete, and we have all the pieces. I wish I had known is that completion is an illusion.
13. When I was at Berkeley, one of my friends got rejected from the business school. Rather than cut his losses, he refused to declare a major and took every class he would need for a business degree. By the time he was done taking those classes, he was roughly a month or two away from graduation. When he went to see the dean, she was beyond irritated by what he’d done. She had no choice but to let him declare a business major and graduate. I wish I had known that reality is malleable if you’re willing to question it.
14. Throughout my life, I’ve stayed in jobs I’ve hated, relationships that were toxic, and clung desperately to people who didn’t care about me the way I cared about them. For the longest time, I believed options and opportunities for everything were scarce and limited. When our default worldview is of one scarcity, it’s impossible for us to show up fully self-expressed and true to ourselves. Instead, we wear masks, hide behind our stories, and let the world see us through the labels that we identify with. I wish I’d known that almost nothing is a finite resource and scarcity is our most toxic social program of all.
15. When you live at home in your 30’s, you get a front row seat to your parents’ aging process. You see their hair get grayer, movement get slower, guts get bigger, and number of pills they take increase. It’s only something you’d notice if you saw them every day. And the more you see it, the more something becomes clear. In spite of all of the fights, disagreements, and disappointments, there will inevitably be a time when they’re no longer there… no longer there to call in a moment of crisis, no longer there to call just so you have someone to talk to, no longer there with food on the table, wine in your glass, a roof over your head, and door that’s always open. I wish I’d known how lucky we are, even if we don’t always see eye to eye, to have parents who care so much.
16. At the end of an interview on David Letterman’s new show, Barack Obama asked Letterman the following question.
“Don’t you say to yourself, ‘Boy am I lucky?’ One of the things I’m always surprised by is when I see people who have been successful in business or entertainment or politics, and they’re absolutely convinced that it’s all because they were so smart. And I’m always saying, well, I worked hard, and I’ve got some talent, but there are a lot of hard working, talented people out there. There was this element of chance to it – this element of serendipity. And I wonder whether you feel that sometimes?
Letterman replied “This is what I’m struggling with at this point in my life – I have been nothing but lucky.”I’ve thought a lot about what Letterman said. And think I’ve been lucky as well:
Lucky to have started a podcast in 2009, when nobody was listening, and Sid Savara told me I was a much better interviewer than a writer.
Lucky that my editor at Penguin landed on my article that day out of the 1000’s that are on Medium.
And while I did put in 10 years of work to this, I can’t help but think of something Mark Cuban said in an interview with Chase Jarvis, “You can become a millionaire through hard work. Becoming a billionaire takes a bit of luck.”
I’ve also been incredibly unlucky to graduate into one recession in 2001, and another in 2009, to keep choosing the wrong jobs until I got fired from every one. But my life wouldn’t wouldn’t be what it is today if those things hadn’t happened. I wish I’d known that good luck sometimes comes disguised as bad luck, and there are often new beginnings in our endings.
17. Throughout your life, your friendships will be tested. In the most fragile of friendships, bridges will burn, ties will break, and what’s occurred will be beyond repair. When you’re headed to different destinations, it’s inevitable that you’ll part ways. I wish I’d known that sometimes you have to let go of the people who are anchors to find the ones who give you wings.
18. With age, the consequences of your actions become greater. You have more to lose, and as a result, your risk tolerance inevitably goes down. If you break a bone, it heals slower. If you have three drinks the night before you wake up wondering why on earth you’d ever do that to yourself. When you’re young, there are consequences, but they aren’t as severe. If a bone breaks, you put a cast on it, and a few weeks later you’re back on the mountain snowboarding with a damn cast on your arm. You can have five drinks and wake up the next day feeling fine. But what’s even more important than this is the capability to take life risks… to join the startup that might not work, to start the company that might fail, to pursue a dream where in the words of Elle Luna “everything is unknown, and anything is possible.” I wish I’d known just how valuable the capacity for the risk you posses in youth was.
19. When somebody asks you the definition of a word, the most natural response is to look it up in the dictionary and tell them the answer. We’ve manufactured consent on what something means. But over the course of your life, the definition of words change. Consider the definition of success. Early in your life, it might be a type of job at a particular company, with a specific salary. But then you get all of that. The definition will change. And if your definitions don’t evolve, you don’t evolve.
The definition of what it means to be commercially successful in a creative career is one I’ve spent a great deal of the last years thinking about, particularly because I just wrote a book called an Audience of One: Reclaiming Creativity for Its Own Sake. And I can’t help but wonder if I’m making this argument for an audience of one, from a place of privilege, with the financing of a major publisher, and ironically with an audience of thousands. But how I define success has changed. When it comes to writing, I want to create things I’m proud to put my signature on. When it comes to podcasts, I want to have conversations that move me, change me, and cause me to grow. In that, there’s an infinite value that simply can’t be measured in clicks, eyeballs, downloads, claps, fans, and followers. I wish I’d known that the most liberating thing you’ll ever experience in life is making your own definitions.
20. Every year as we got older, many of my friends from college would hit major milestones in their lives, graduations, marriages, kids, etc. And every time I’d feel like I was falling behind and mention this to my oldest friend from college, she’d say, “What are you going to do race to the death?” About a month ago I had a chance to speak with an incredibly successful photographer. After photographing Super Bowls, NHL Championships and other major moments, he said that his measure of success had become whether he was better today than he was yesterday. I wish I’d known that the only person worth competing against is the previous version of yourself.
21. When I graduated from business school in April 2009, I had no job, no hope and no money. I volunteered to work the door at networking events so I could get in free. I carried a flask so I wouldn’t have to buy drinks at bars. It was certainly not the life I had expected to be living at the age of 31. But it was also one of the most transformative periods of my life because I started surfing and writing. If you’re in between jobs, or facing graduation with an uncertain future, what I would say is that you have a blank canvas. This is a wonderful thing because it’s an opportunity to create the life you truly want. So write down what your ideal life would look like. Write down something so daring, bold, and audacious that it motivates you to wake up every morning. I wish I’d known that a blank canvas is an opportunity to turn your life into a masterpiece.
22. In your life, you’ll encounter teachers. Some will be actual teachers. Others will be mentors, and some will be friends, business partners, and lovers. Every one of them will teach you a lesson. In the movie Van Wilder, one of the most repeated phrases you hear Van say is, “Write that down.”
Write down everything you learn from everyone. If you do this, you’ll have your own set of operating principles, a book of personal wisdom what will serve as a compass for your life. I didn’t start writing every day until I was in my 30’s and I wish I’d known just how powerful it can be to write things down and create a set of principles that guide your life.
23. In the seventh grade, a kid that I had been friends with since the fifth grade walked up to be and said: “Srinivas, I don’t want to be friends anymore.” There was no explanation, but I knew that he was on the verge of becoming popular. I was not. Of course, I spent a great deal of my life trying to be cool, popular, and fit in. I wish I’d known that the coolest thing you can be is uncool, and in adult life, you get rewarded for standing out, not fitting in.
24. In 2014 we planned a conference called the Instigator Experience. It was something I’d been dreaming about for years. I created the event I’d always wanted to go to. But in 2015, we didn’t sell enough tickets. This year I attempted another bold project: a conference where every attendee had been a guest on The Unmistakable Creative. The overwhelming majority of people weren’t interested. The first time I was devastated. This time I shrugged it off and got back to work. I wish I’d known, when it comes to ambitious creative projects, sometimes you just have to pull the plug.
25. People often ask me how I ended up becoming a writer, speaker and podcast host. And the answer I always give them is “by accident.” None of this was part of some grand plan. When you have a calling, you’ll do something when nobody demands or expects anything from you. It’s how most creative careers begin, with nobody paying attention. I wish I’d known just how much creating for an audience of one was going to change my life.
26. Three weeks after I started college at UC-Berkeley, I walked into a career fair. Never mind the fact that I concerned myself with something that was four years away. I was giving some serious thought to majoring in English until a recruiter from Accenture kindly informed me that they didn’t hire many English majors. I wish I’d known that it makes no sense to follow the advice of people who won’t live with the consequences of your choices.
27. Throughout this life, you’ll reach multiple forks in the road. Do I break up with this person or not? Do I quit the job or not? Do I take the bigger paycheck with the boss who seems like a total douchebag?
Ten years ago I surfed at Cardiff for the first time. The Friday before I had quit a job after two weeks. When I got out of the water, I thought to myself, “This is where I want to live someday.” And while it took almost 10 years to get here, today I’m a two-minute drive from that same stretch of beach. Every time I reached a fork in the road, I chose the one that would get me closer to Cardiff.
When you reach a fork in the road, ask yourself which path will allow me to be the person I want to be a year from now and ten years from now? I wish I’d known just how important it is to consider both the present and future impact of the decisions we make today.
28. Out of fear and comfort, we often stay in situations that are less than ideal. Even though I knew it was a toxic working environment, I stayed at my first job out of college. The CEO instilled a fear in me that because of a bad economy opportunities for work were limited. He also used this as an excuse to justify not paying salespeople commissions. Last year, I spent almost two months chasing some girl who wasn’t really into me.
I wish I’d known that sometimes the best thing you can do for yourself, and thing that reinforces your self-worth is to walk away (H/T Nick Notas).
If someone is not treating you with love and respect, it is a gift if they walk away from you. If that person doesn’t walk away, you will surely endure many years of suffering with him or her. Walking away may hurt for a while, but your heart will eventually heal. Then you can choose what you really want. You will find that you don’t need to trust others as much as you need to trust yourself to make the right choices.” – Don Miguel Ruiz
29. Sometime around age 36, I had my first real heartbreak. The pain felt like it was never going to end. I played every moment over in my head, wondering if I had done one thing differently if the outcome would have been different. I tortured myself for months, cried almost every day, while at the same time vowing to myself that I would never in this lifetime cry in front of a woman. I beat myself up, emotionally, physically and in any other way I could. When I told a Doctor I smoked a pack of cigarettes and drank 3/4 of a bottle of Whisky in a day, she said, “You’re punishing yourself.”
And what I can see now is somewhere deep down, I hated myself. For years, I had hated myself for not being the person I thought I should be, for being that old and still living at home, for not being where I wanted to be in my career and so much more… When you’re consumed by such a deep sense of self-loathing, no accomplishment can provide you with a lasting sense of fulfillment. I wish I had known that the most important relationship you’ll ever have is the one you have with yourself.
30. If you’ve ever experienced heartbreak, you’ve probably gone through this familiar routine. You play back every moment of the relationship in your head. You over analyze everything you ever said, find one or two moments that you think changed how your ex felt about you, and keep imagining how things would have turned out differently if you’d done something different at that moment. After you’ve rewinded and edited the movie in your head a thousand times, you realize that the outcome is still the same. I wish I’d known that there are some questions that you’ll never have answers to, no matter how hard you try to find them.
31. I’ve tended, in the past, to get too emotionally invested in people too quickly. Because of how physically attracted I was to someone, I was blinded to all of their other qualities. The result was loose boundaries, unhealthy relationships, and a willingness to put up with just about anything so I wasn’t alone. With infatuation, our emotions go from zero to 10 quickly. And it feels amazing. But as my business partner Brian once said to me, “Whether it’s a relationship or a customer, anything that goes from zero to 10 that quickly is likely to go from 10 to zero just as quickly.” Infatuation is a crescendo that takes place over one measure. A true connection, on the other hand, builds and has a crescendo that occurs over multiple measures. I wish I had known that there’s a difference between infatuation and a true connection.
32. It was a Friday morning just a few weeks ago. I’d been dating someone for a couple of months when I got a text that said, “Can you chat for a few?” After 40 years, I know those words in any form are the precursor to a breakup. She wasn’t feeling a “fuck yes” about me.
Whether they’ve been in your life for two months or two years, somebody could be gone at any moment. That’s the risk we take when we open our hearts and let people in. When I told one of my friends I said, “I’m not devastated, just disappointed.” I’d like to think this was a sign of growth. I wasn’t falling head over heels for someone when I barely knew them. And I thought to myself, so this is 40? An ending and a new beginning all in the span of a few weeks. I wish I had known that being unwanted doesn’t mean you’re unlovable.
33. It was December 20, 2001. I had just returned from another co-worker’s goodbye lunch when the VP of sales at my first company called me into a conference room. Five days before Christmas I was fired from my first job out of college. I couldn’t hold back the tears. There I was supposedly a grown man, crying in front of a senior executive. I’d put in 13 hour days, endured an awful commute for nine months, and even developed a case of IBS because of this job. Despite all that, losing my job was devastating. The loss of money and thought of having to explain it to another employer paralyzed me with anxiety. But that was the first of many jobs that I’d eventually be fired from. Setting me on the path to become a writer and speaker. I wish I had known that sometimes our losses liberate us from the life we live so that we can pursue the one we’re destined to lead.
34.The summer before my last semester at UC-Berkeley, I met a young entrepreneur in a coffee shop who offered me a job for $10 an hour but promised me that I would also learn a ton working with him. I turned down the job and chose another job that paid $25 an hour. In the middle of that summer, the company I worked for ran out of money. And years later that young entrepreneur in a coffee shop went on to the be the founder of several companies that ended up being worth hundreds of millions of dollars. An extra $15 an hour cost me a potential fortune. I wish I had known that the best thing you can do early in your career is increase your earning potential instead of just increasing your earnings.
35. Because of where I went to college, I was exposed to one definition of success: work at an investment bank, a management consulting firm, or go to law school, med school or a top 10 business school. According to this definition of success, I’m an abysmal failure. Every now and then there’s this small part of me that craves the validation that comes from prestige, so I do something like send a job application to IDEO just to see if they’ll even take a look at me. After all who wouldn’t want to work at IDEO? And nobody did take a look at me. My friend Mike called me on this. “That’s just ego. You’d be there a month and realize you hate not having your freedom.” I wish I had known that prestige is different than the kind of success that provides you with lasting fulfillment.
36. When I applied to business school in 2007, I had a dream of working in media and entertainment. I wanted to work programming at a Television network and choose what went on air. But after a few months in LA, I learned that nobody hires MBA’s to do creative work. As the host and founder of a podcast, a writer of books, and producer of animated shorts, today I not only get to choose what goes on air, I get to create it, which is what I was longing for. I wish I’d known then that dreams come true in the most unexpected ways.
37. When I was younger, almost every decision I made about my education and my life was driven by what might get me a job. I went college in the Bay Area during the dot-com boom. So I attempted to take a computer science class and was so bad at programming that I dropped the class before the end of the semester. And as a result, I wasted one of the greatest opportunities of my life, college; to explore, collect data points and indulge my curiosity. If you’re young and reading this, I’ll pass on this piece of advice I shared with graduating seniors.
Don’t worry about what you want to do for a living. Instead, make a list of everything you’ve ever wanted to do. Write it down somewhere. Refer back to it from time tie time. Every time you cross off something on the list, you have a new data point for your collection. Neil Gaiman would call this your “distant mountain.” Every decision you make about your life is either taking you away from the mountain or towards. Don’t walk away from the mountain and let curiosity fuel your ambition. I wish I’d know that curiosity precedes passion, passion follows engagement and meaning follows mastery.
When I took Yaro Starak’s course Blog Mastermind, one of the lessons was to interview a person to get traffic to your blog. Instead of interviewing one person, I started a weekly series called Interviews with Up and Coming Bloggers that was the precursor to the Unmistakable Creative. The greatest work of your life requires a compass, not a map. If you want to end up at a destination that nobody’s been to before you have to be willing to ditch the map and take a detour. I wish I’d known just how valuable it can be not to follow the instructions to the letter.
39. When I started my blog in 2009, I looked up to all the people who had landed book deals as a result of their writing. I wanted to be one of them. And I spent the next 6 years telling their stories. Somewhere in the middle of all that I had a conversation with a woman who helped authors land book deals. She didn’t think I was ready. Even though I was disappointed, I realized she did me a huge favor. She gave me another two years to work on my craft. Not only did I end up getting a much more lucrative book deal, but I ended up with a publisher that had published the books of many of my heroes. I wish I’d known that sometimes it’s a blessing in disguise when it takes a bit longer to accomplish your goals
40. For the longest time I thought I’d finally be happier when I had achieved some sort of milestone:
When I got a book deal (check)
When I moved out of my parents’ house (check)
When I fell in love (a work in progress)
But waiting to be happy until something external changes in our lives is a self-imposed handicap. The fulfillment and satisfaction from anything external is always going to be fleeting. Attempting to solve an internal problem with an external solution is like putting a bandaid on a bullet wound. It might temporarily stop the bleeding, but eventually, you’ll die.I wish I’d known that you can’t solve internal problems with external solutions.
As I sit here looking back over 40 years, it’s been a life filled with disappointment and delight, sorrow and joy. It’s tempting to think that I might have done certain things differently, but If I had I wouldn’t know so many of the things that I do. That’s the nature of so many life lessons. You only recognize them in retrospect. As my friend and author CC Chapman says Amazing Things Will Happen.
So if you’re 20, I feel compelled to tell you that you have all the time in the world. Don’t be in too much of a damn hurry, but don’t waste your time as well. If you’re over 40, I feel compelled to tell you that it’s never too late for even your wildest dreams to come true.
We think that we know…. What it will look like when we’re 30, 40, 50. What it will look like to be married, have kids, fall in love, and build our empires. But there’s only one thing I know for sure:
The future is unwritten and uncertain, and when we hang on to how we think it should be, we get in the way of how it could be.
I’ve created a swipe file of my best creative strategies. Follow it and you’ll kill your endless distractions, do more of what matters to you, in higher quality and less time. Get the swipe file here.