Forty Years of Wisdom: “Sometimes in life, you still end up as a sugar cookie.”

Comedian Dave Chappelle

I also am closing in on 40. Do you remember Stephen Covey? The Seven Habits of Highly Effective People is a classic. And do you know what I still remember decades later? “Begin with the end in mind.” That makes even more sense after two decades of being an adult. What advice would I offer a young person preparing for college, a career, or adulthood. That’s what follows. It reads like a collection of ideas- wisdom for a younger generation and things I still need to remind myself of. How to define success, maintaining a proper perspective, and thoughts on work. Forty years of wisdom with the subtitle, “Sometimes in life, you still end up as a sugar cookie.” Enjoy.

On Work

Venture capitalist Chris Sacca

Be interesting

Chris Sacca said, “Be interesting.” The man was an early investor in Twitter and Instagram and runs the most successful VC fund ever. I pay attention when Chris Sacca speaks. In an interview on the Tim Ferriss podcast, the “Be interesting” idea came out. And this is where I begin. Too many people are boring, and too much of life is mundane. Be interesting. Do cool stuff. Do stuff worth talking about.

Do work that matters.

Leaving Microsoft to Change the World is a dangerous book to read. John Wood tells his personal story of leaving a lucrative job with Microsoft and starting a non-profit called Room to Read. The idea started with a desire to build a library for some schools in Nepal. Eventually, this went from a side project to Wood’s full-time passion. He came to the point where he wrestled with himself about whether to quit Microsoft or not. “Did it really matter how many copies of Windows we sold in Taiwan this month,” Wood asked himself. Did his job really matter when millions of children were without access to books? A successful year would only help a rich company get richer. Wood wrestled with whether or not to quit. “Microsoft will miss you for a month or two,” one of the voices in his head said. “Someone will quickly fill the void. It will be like you never worked there.” The inner voice went on, “Ask yourself, are there thousands lining up to help poor villages build schools and libraries? That job is not being done. You should rise to this challenge.” Do work that matters. Whatever that looks like for you.

Be 10,000 times better than the competition.

“The top software developers are more productive than average software developers not by a factor of 10x or 100x or even 1000x but by 10,000x.” Nathan Myhrvold, former chief technology officer at Microsoft, famously made that statement. Comedian Steve Martin says it another way. He says, “Be so good they can’t ignore you.” When a start-up wants Chris Sacca to invest in their company, Chris Sacca will ask, “What is you unfair advantage?” So be 10,000 times better than the competition. Know what your unfair advantage is, and be so good they can’t ignore you.

Best-selling author Neil Gaiman

Make good art.

Thanks to the Four Hour Work Week blog, I discovered a commencement speech by Neil Gaiman. The blog post is titled “The Best Commencement Speech You May Ever Hear.” Gaiman said that when things get tough, when things go wrong, you should make good art. “Husband runs off with a politician, make good art. Leg crushed and then eaten by a mutated boa constrictor, make good art. IRS on your trail, make good art. Cat exploded, make good art. Someone on the internet thinks what you are doing is stupid or evil or it’s all been done before, make good art….Do what only you can do best, make good art. Make it on the bad days. Make it on the good days too.”

Make your art.

Do the stuff that only you can do. This is another golden nugget from the Neil Gaiman speech. Make your art. If you try and do things that you think will be a commercial success, you will most likely fail. Don’t try and sound like someone else. Use your voice, your story. Don’t be a hack. Don’t worry about commercial success. Do the stuff that only you can do; make your art.

Quit waiting to be discovered.

Hugh MacLeod writes that “If your business plan depends on suddenly being ‘discovered’ by some big shot, your plan will probably fail.” We all have examples that come readily to mind of people who turned their blog or their Twitter presence into their dream job. But thanks to the internet and social media you can build your own thing without having somebody else discover you first. Trust what you want to do and not what you think will work.

“We must do our work for its own sake,” writes Steven Pressfield, “not for fortune or attention or applause.” Here’s another test, as Pressfield explains it. Of any activity you do, ask yourself: If I were the last person on earth, would I still do it? If you’re all alone on the planet, there’s no one to impress. So, if you’d still pursue that activity, you are on the right track. Pressfield’s example is if Arnold Schwarzenegger were the last man on earth, he would still go to the gym. Stevie Wonder would still tinker around on the piano. Brittney would still play volleyball. If you have an idea of what you were put here on earth to do, just go and do that. Be careful not to make someone else’s path or someone else’s voice your own. Quit hoping to be discovered; just go do what only you can do best.

Comedian Jerry Seinfeld

The Seinfeld secret to success.

I am a huge Jerry Seinfeld fan. The success of the show Seinfeld needs no commentary. It’s been well documented. In an interview with Alec Baldwin on Here’s The Thing, Jerry shared the secret to the success of the show. He said that other shows would spend 50% of their time writing and 50% of their time dealing with the other things that come up when you deal with the television business. But on Seinfeld, they spent 99% of their time writing. Jerry and Larry David closed the door. They did not take calls. Other people were not allowed in. They focused on the writing; they didn’t allow anything to interfere. Ninety-nine percent of the time and effort went into making the show funny.

Another way to look at it comes from the book Essentialism: The Disciplined Pursuit of Doing Less. The author writes, “Do only things that matter, only the essential. Ignore everything else.” The two themes that stuck out in this book were “do only things that matter” and “do less but better.” As author Greg McKeown explains, essentialism is “a method for making the tough trade-off between lots of good things and a few really great things. It’s about learning how to do less but better so you can achieve the highest possible return on every precious moment of your life.” Or as Jerry Seinfeld explained, you shut the door and focus on the writing. You don’t take calls. You don’t allow interruptions. You just try and make the scene funny. What are the few, really great things that yield the highest return for you? Focus 99% of your efforts there, and ignore all the rest.

Be obsessive.

I have heard Chris Sacca tell this story twice. Uber founder Garrett Camp was spending New Year’s with Sacca and his family. Mr Sacca, Chris’s dad, was at the house and Garrett and Mr. Sacca ended up playing some Wi tennis. The games were close but Garrett was barely breaking a sweat. Mr. Sacca was taking full swings, while Garrett was just using a flick of the wrist. Plus, he was a little hungover from the night before. I don’t remember if Camp is naturally right-handed or left-handed, but, unbeknownst to Mr. Sacca, he was playing with his off-hand. After a couple of games, Camp switched and began playing with his true hand. Mr. Sacca never touched the ball again. Finally, Camp came clean to Mr. Sacca and showed him the Wi Tennis leader board. Garrett Camp was the second highest rated Wi tennis player in the world. Uber was already a thing at this point. So not only was he the head of a start-up, but he was the second best Wi tennis player in the world.

Focus on depth over breadth.

Remember the movie Searching For Bobby Fischer? The child chess prodigy in the movie is the real life Josh Waitzkin. Waitzkin rose to the top of the chess world, then proceeded to do the same at Tai Chi Push Hands and now studies Brazilian Jiu Jitsu. His real talent is learning. He even wrote a book called The Art of Learning. Waitzkin writes that the most common error in learning a new task is to take on too much at once. “Everyone races to learn more and more, but nothing is done deeply,” writes Waitzkin. Focus on depth over breadth.

Warren Buffett is the perfect example of depth over breadth. In an interview with Buffett, Fox Business asked Buffett how he came across this then-relatively obscure foreign company, PetroChina. Buffett went on to talk about how he invests. He doesn’t look at companies based on countries. Rather, he reads every report he can and tries to find a good value. Journalist Liz Claman pressed this issue further. “But how would you find a report like PetroChina four years ago?” she asked. “Other guys read Playboy,” Buffett replied. “I read annual reports.” Buffett obsesses over annual reports. His knowledge is extremely deep, rather than broad. So focus on depth over breadth.

Know how to stretch, how to push through.

Michael Lewis wrote a small book called Coach: Lessons on the Game of Life. The book is a tribute to his high school baseball coach. It’s also an indictment of the problems with youth sports today. Today, Michael Lewis is considered maybe the best non-fiction writer of our time. Meanwhile, the old coach is still at the same private high school in New Orleans coaching baseball.

In the book, Lewis goes back to visit his old coach and the current team. The team is struggling, but the coach is the same demanding coach who focuses on teaching life skills as well as baseball. During one point in the season, the old coach has a heart-to-heart with the team. Lewis sat in the locker room as the coach addressed the team following a tough loss. “One of the goodies about athletics,” begins the coach, “is you get to find out if you can stretch. If you can get better. But you got to push. And you guys don’t even push to get through the day. You put more effort into parties than you do into this team.” As David Shenk points out in his outstanding book, The Genius In All of Us, “Our brains and bodies are primed for plasticity; they are built for challenge and adaptation. Being great at your trade takes work. It takes getting up everyday and doing your job- on the good days and the bad. You have to know how to push through.

A small story from Tom Brokaw’s The Greatest Generation Speaks can teach the rest of us how to push through. This is the book where Brokaw published some of the hundreds of letters he received following the first book, The Greatest Generation. One WWII veteran writes, “Let me start by saying that I am a part of the WWII generation. I served in the Eighth Air Force as a co-pilot on a B-17, flying 31 missions. We came home to forget what hell we had gone through and we all wanted to just get married, settle down, and live like ‘normal’ people. I arrived home on Labor Day 1945, and was at work at my old job the very next day at 8:00 a.m.” Picture that. A co-pilot of 31 missions in World War II. He comes home Labor Day and started work at 8:00 a.m. the next day. That’s work ethic.

Think meal-to-meal

I have a fascination with reading Navy SEALS books. In the book No Easy Day, Mark Owen writes, “I’d made it through Basic Underwater Demolition/SEAL, or BUD/S, by focusing on just making it to the next meal.” Owen mentions the saying, How do you eat an elephant? Answer: One bite at a time. He then writes, “my bites were separated by meals: Make it to breakfast, train hard until lunch, and focus until dinner. Repeat.” In the book American Sniper, Chris Kyle echoes the meal-to-meal mindset. Kyle writes, “Before BUD/S began, someone told me the best way to deal with it is to go meal-to-meal. Go as hard as you can until you get fed. They feed you every six hours, like clockwork. So I focused on that. Salvation was always no further than five hours and fifty-nine minutes away.

Work a crappy Job.

Another gem from Chris Sacca. He was talking about what he looks for in a new hire. Bad jobs teach us a lot. Enduring a bad job for a season toughens you up. It gives you a better perspective for every job you will have in the future. Texas Men’s Basketball Coach Shaka Smart says, “When I was a kid the best thing my mother ever did for me was make me work a couple jobs that I really hated. I worked as a landscaper and in asbestos removal. I found out that I never wanted to do that again. So I’m very lucky and appreciative to be able to be a coach.” NFL Hall of Fame Wide Receiver Jerry Rice worked alongside his father, a bricklayer by profession. That hard job motivated Jerry to succeed as a college football player and eventually in the NFL because he knew he did not want to lay brick for the rest of his life. Work a crappy job. It will help remove any feelings of entitlement and make you appreciate things more.

Be willing to walk away.

The person that cares the least wins. I think most of us are taken advantage of when it comes to negotiating. Skilled negotiating means being prepared. The person with the most information wins. You also need to be willing to walk away. Brigitte Bardot is a former actress, singer and fashion model. She was one of the best known icons of the 1950s and 1960s. Bardot famously said, “I leave before being left. I decide.” Be willing to walk away. Learn to be a master negotiator.

On Lifestyle Design

Strength Coach Dan John

Have some reserves.

Everyone’s a fitness guru these days. Anyone who has completed an online certification or played a sport in college wants to be an expert in this extremely overcrowded industry. Therefore, ignore 99% of what you read. But Dan John is legit; he is a voice you should listen to.

In his book, Intervention, there is a chapter called What if You’re Spinning Out of Balance? Dan John uses the analogy of a traffic light. Think of the standard traffic light, but picture the horizontal version and pretend that it starts on the far left with the green light. Green is go, yellow suggests caution, and red means stop. Dan writes that his goal is to be in the green area for every area of his life: relationships, finances, time, fitness, sleep, etc. “For me,” he writes, “life in the green side is all about having some reserves. I have enough in the bank to cover a minor tragedy of life, like a broken water heater, and I have enough time to help a buddy move a couch. I have enough energy to train and enough energy after I train to still enjoy some entertainment with my family.” As I close in on 40, I appreciate this. I want to live in the green, and the secret to staying in the green is to have some reserves.

Make your bed.

Make your bed. Another item that came from Tim Ferriss and his podcast. While talking with his guest, entrepreneur Noah Kagan, the two began to talk about the benefit of making your bed everyday. Tim mentioned a commencement speech he once heard from a decorated military leader who talked about the benefits of making your bed daily. He didn’t remember the speaker or where the speech was given, but the idea hit home with him. Noah also mentioned this daily practice. It’s an overlooked aspect of adult life, which- when done every morning- can make you feel organized and in control of your day. I began my new habit of making the bed that very day.

But an amazing thing happened months later when I listened to a sermon by a pastor in Indianapolis who I admire and respect. He began talking about a commencement speech by a former Navy SEAL. And he wanted to talk about two of the principles from the speech that stood out to him. The first one was the idea of making your bed. Then Pastor Mark quoted Admiral McRaven, a 38-year veteran of the SEALs:

“It was a simple task, mundane at best. But every morning we were required to make our bed to perfection. It seemed a little ridiculous at the time, particularly in light of the fact that we were aspiring to be real warriors, tough battle-hardened SEALs, but the wisdom of this simple act has been proven to me many times over. If you make your bed every morning you will have accomplished the first task of the day. It will give you a small sense of pride, and it will encourage you to do another task and another and another. By the end of the day, that one task completed will have turned into many tasks completed. Making your bed will also reinforce the fact that little things in life matter. If you can’t do the little things right, you will never do the big things right… If you want to change the world, start off by making your bed.”

Spend time with old people.

All my grandparents passed away years ago. I miss spending time with them; I miss that I’m not around old people much anymore. My dad’s parents lived in a small town in rural Iowa for years. My grandpa was a World War II veteran. Your perspective on life changes when you were a passenger on a carrier that was sunk by a German U-boat. My grandpa sold feed most of his life. I miss my grandparents and that rural life I witnessed on trips to their house. Comedian Dave Chappelle said, “You know you’re doing something right if old people like you.” I want old people to like me. I want to spend time with them. I want to be a person who enjoys listening to people who are- as pastor and author Andy Stanley phrased it- “farther down the road than I am.”


“In my whole life I’ve known no wise person who didn’t read all the time- none, zero.” That’s a quote from Charles Munger, the man famous for being Warren Buffett’s business partner. Munger goes on, “You’d be amazed at how much Warren reads- and at how much I read. My children laugh at me. They think I’m a book with a couple of legs sticking out.” Read books. Victor Davis Hanson writes that the actual vocabulary of our present youth seems to be reduced to about 1,000 words or so. Reading is exercise for the mind. Hanson writes,“Reading alone enriches our vocabulary; it teaches us that good writing requires a sense of melody as well as command of grammar. Soon those well-read become the well-spoken.” Just a few reasons why I want to continue reading.

Slow down.

Do an experiment sometime. Drive somewhere- with no time restrictions or expectations for when you are supposed to arrive- and just notice how big of a hurry everyone else is in. The following quote comes from the book Zen and the Art of Motorcycle Maintenance. “We’re in such a hurry most of the time. We never get much chance to talk. The result is a kind of endless day-to-day shallowness, a monotony that leaves a person wondering years later where all the time went and sorry that it’s gone.” Pause and constantly ask yourself if you are investing in the right activities. That’s advice straight from the book Essentialism. Kevin DeYoung’s book Crazy Busy advises, “We need downtime each day, and a respite each week, and seasons of refreshment throughout the year.”

Most of my adult life I have neglected this advice. While on vacation, I sat in an unfamiliar church as the pastor spoke on “a pace of life that is way too busy with too many pressures.” If felt like he was speaking directly to me. He went on to say, “It isn’t long until busyness leads to frazzledness, which leads to frustration and sinful anger.” Busyness has been the theme of my life for far too long. Perhaps that’s why Kevin DeYoung’s book means so much to me.

DeYoung admits he wrote the book for himself. In addition to being a pastor, he is a highly sought-after speaker, an author of several books, and a father of five. DeYoung writes, “What does it say about me that I’m frequently overwhelmed? What do I need to learn about myself? What biblical promises am I not believing? What’s going on in my soul, so that busyness comes out as my chief challenge every year?”

Have you been living at a pace that is not sustainable long-term? Slow down. I don’t want to be the person wondering years later where all the time went and sorry that it’s gone.

Do nothing.

Brene Brown writes, “In today’s culture- where our self-worth is tied to our net worth, and we base our worthiness on our level of productivity- spending time doing purposeless activities is rare.” The quote is from her book The Gift of Imperfection. Brown goes on to write, “We’ve got so much to do and so little time that the idea of spending time doing anything unrelated to the to-do list actually creates stress… We even convince ourselves that sleep is a terrible use of our time.” Doing nothing means putting the iPhone in the other room. Don’t scroll through your Twitter feed. Quit the endless internet research. Sit and talk for an hour. Sit and read, or sit and do nothing.

Eight hours of sleep is the miracle pill.

Many successful people talk about the importance of sleep. There’s no shortage of research to back this up. Commit to getting eight hours of sleep every night. Set a routine. As much as possible, go to bed at the same time every night. Get eight hours of sleep and see what happens. It is the miracle pill that most of us desperately need.

NY Times best-selling book Radical by David Platt

Spend time overseas. Spend time among the poor.

Both of those ideas force us to be in a different context. Most of us aren’t around poor people. And life anywhere in America is pretty easy, especially for middle class Americans and white Americans. Chris Sacca mentioned both ideas when talking about things he looks for in a new hire- someone who has studied abroad or spent time overseas and someone who has experience working with or living among the poor.

Pastor and New York Times best-selling author David Platt wrote about the importance of spending your time in another context. If you can’t spend three or six months or a year overseas, go on a two week mission trip. Those experiences make you stretch. They teach you to be flexible. Living among the poor- befriending the poor- will make you see things differently too. The end goal is not to feel good about your life and what you have. That’s not the point. Yes, it will provide perspective, but it’s about coming alongside someone who lives in a different context as you. Don’t focus on helping them. Just spend time with poor people. Spend time with a refugee family or spend time overseas.

A scene from The Burning episode, Season 9 of Seinfeld


I have Seinfeld DVDs on hand for the sole purpose of making me laugh. In the book Too Soon Old, Too Late Smart, Gordon Livingston writes about laughter.“It is revealing to ask those in the grip of depression when was the last time they laughed.” Laughter is good for the soul and Norman Cousins devoted a whole book to his own experience of curing himself from a debilitating, undiagnosed disease using little more than old Marx Brothers movies.

“What gives humor its power in our lives,” Gordon Livingston writes, “is that a capacity for laughter is one of the two characteristics that separate us from other animals. The other, as far as we know, is the ability to contemplate our own death.” My wife and I had a busy season of life recently- a tough three years. This past year being maybe the busiest and most stressful. We hadn’t laughed in a long time. Too busy to laugh; too frazzled to laugh. Thankfully, we had all nine seasons of our favorite show, Seinfeld, on DVD. From the Hot Tub episode to The Burning and The Summer of George, we started to put in Seinfeld episodes and enjoy a good laugh. Whether life is busy or slow and easy, have a good laugh.

On Mindset

Fight the never enough problem.

Many people talk about feeling trapped by possessions. An entire industry has arisen with so-called experts to help you declutter and simplify your life. I want the type of simplicity that Rolf Potts writes about in Vagabonding. Potts writes about stopping expansion (you don’t add new possessions to your life), reigning in your routine, and reducing clutter. Potts lives this philosophy, and traveling the globe for extended periods of time forces that type of simplicity. For those who cannot or prefer not to travel for months at a time, simplicity still has merits. But the battle will be against an American, consumeristic culture that will fight you every step of the way.

Consumerism. Never enough. Even if you never read the newspaper, don’t own a television, and limit your online reading, you still can’t escape these ideas. You can call it “scarcity” or the “never-enough problem” according to author and speaker Brene Brown. Brown describes it as “never good enough, never perfect enough, never thin enough, never powerful enough, never successful enough, never smart enough, never certain enough, never safe enough, never extraordinary enough.” She writes, “We spend most of the hours and the days of our lives hearing, explaining, complaining, or worrying about what we don’t have enough of… Before we even sit up in bed, before our feet touch the floor, we’re already inadequate, already behind, already losing, already lacking something.”

This is a battle on two fronts: simplicity and contentment. I need the contentment that Kevin DeYoung writes about. Contentment is saying, “God has me here for a reason, and if He never does anything different, I’ll still serve and praise Him.” Strive for the simple life. Be content.

The danger of expectations.

Dan John is part philosopher and part strength coach. This is another insight from him. He talks about a park bench mentality versus a bus bench. Dan John borrowed the concept from an archbishop. In the Tale of Two Benches, Archbishop George Niederauer explains that the two benches are a bus bench and a park bench. On the bus bench, we sit pragmatically, restless in anticipation, waiting for the bus to arrive. When we wait for a bus, we are filled with expectations- in many ways a slave to those expectations. The G line should be here at 8:11. If I look up at 8:11 and don’t see it, I begin to panic. At 8:13 my day is ruined. But not on a park bench. Bishop Niederauer advises us to go to the park bench for its own sake. Sit in the silence, with birds singing and children playing, and the sun shining through the leaves of the trees. Nothing is produced. Nothing is done. Sit, listen, and watch. Wait for nothing. The two squirrels that showed up yesterday may or may not be here today. And that’s okay.

Love everything that happens to you.

Maybe the best chapter in Ryan Holiday’s book is the chapter titled Love Everything That Happens: Amor Fati. The book is called The Obstacle is the Way. Holiday writes, “We have to learn to find joy in every single thing that happens.” Learn to love whatever happens to you and face it with unfailing cheerfulness. Holiday points to the Stoics who preached cheerfulness in all situations, especially the bad ones. “We don’t get to choose what happens to us, but we can always choose how we feel about it. And why on earth would you choose to feel anything but good?”

Choosing a positive attitude is a common principle in athletics too. “You have to choose to think well,” writes Bob Rotella in Golf Is Not a Game of Perfect. Learn from good athletes; they create their own realities. “If you’re going to be a victim of the first few holes,” writes Rotella, “you don’t have a prayer. You’re like a puppet. You let the first few holes jerk your strings and tell you how you’re going to feel and how you’re going to think. You’re going to have to decide before the round starts how you’re going to think, and do it on every shot. You have to choose to think well.” Love everything that happens to you. Ryan Holiday adds, “You love it because it’s all fuel. And you don’t just want fuel. You need it.” Choose to think well. Love everything that happens to you.

The art of not panicking.

Ryan Holiday also talks about “unflappable coolness under pressure.” Holiday writes, “You will come across obstacles in life- fair and unfair. And you will discover, time and time again, that what matters most is not what these obstacles are but how we see them, how we react to them, and whether we keep our composure.” Josh Waitzkin says, “In every discipline, the ability to be clearheaded, present, cool under fire is much of what separates the best from the mediocre.” As I close in on 40, I hope I am wiser; I hope I can remain cool under pressure.

On Priorities and Perspective

Never do anything just for the money.

Neil Gaiman talked about an experience early in his writing career that made him decide, in the future, to never write books just for the money. “If you didn’t have the money, then you didn’t get anything,” Gaiman said. “And if I did work I was proud of- and I didn’t get the money- at least I’d have the work.” Here’s my favorite part of the quote, “Nothing I did- where the only reason I did it was for the money- was ever worth it, except as bitter experience.”

That extra money sounds good initially. But when it’s all over, I agree with Neil. The extra assignments, the extra work, the things we choose to do only for the money, are never worth it. They only serve as bitter experience.

Life on your own terms.

Do you have life on your own terms? In an interview with Jerry Seinfeld, Alec Baldwin asked Jerry why he never pursued any of the multiple opportunities that came his way after the success of the show Seinfeld. Jerry replied that the success of the show gave him the ability to choose life on his own terms. ON MY OWN TERMS. That was the gift that the success of the show gave him. He could now live life on his own terms. He enjoys doing stand-up comedy so he does a select number of shows every year. But Jerry has also said no to countless offers in movie and television. He is enslaved by nothing; he lives life on his own terms.

Comedian Dave Chappelle

How do you define success? Or how to turn down $50 million.

Comedian Dave Chappelle is an amazing study in shunning the American ideal of success. The comedian was called “the comic genius of America” by Esquire. Chappelle’s show once set the record for most DVD sales for a television series. But then Dave Chappelle disappeared. He became famous for walking away from his own show. He turned down $50 million dollars and quit. Rolf Potts and Tim Ferriss had a great discussion about this on Tim’s podcast. What does it say about America that we determine success solely based on a large payday and question people’s insanity when they choose lifestyle design over the big payday?

People literally thought Chappelle had gone insane. No one in their right mind would turn down $50 million. Chappelle turned down the money, walked away, and moved to a farm in his home town of Yellow Springs, Ohio. The man turned down media requests and pretty much disappeared. Yet those who saw him and knew him saw a guy who was fit and happy and spending time with people he enjoyed. With or without the $50 million contract, that looks like success to me: a smile that says you are truly happy, enough time that you can exercise and be active, and spending time with the people you enjoy.

I read a fascinating article about Chappelle by Rachel Kaadzi Ghansah in Believer magazine. I wanted to learn more about the man who walked away from $50 million to live in his hometown of 3,500 people. Chappelle never spoke with Ghansah. She just went to Yellow Springs to try and understand the man and what his life looked like now. She talked to locals and some family members. If large paydays are the American ideal of success, then Chappelle shunned that model. But, like Jerry Seinfeld, Dave Chappelle lives life on his own terms. As others told Ghansah as she was researching her article, “The man turned down fifty million dollars. You will never get him to speak with you.” That’s freedom. That’s creating your own definition of success. That’s life on your own terms.

Don’t play it traditionally.

Another Chris Sacca story. He talks about living in San Francisco and feeling like he was never accomplishing anything. Finally, Chris and his wife moved to Truckee, about three hours outside of Silicon Valley. Now, he had an excuse. He couldn’t go to meet-ups because he now lived three hours away. If start-ups wanted to pitch him, they had to drive three hours to Truckee. Keep in mind, at the time Sacca made the move, it was risky. It was a career risk. Why would a venture capitalist move three hours away from Silicon Valley? What if he was now out of the loop? What if no one was willing to come to him? Even the house they purchased at the time was a bit of a financial risk. What if this was career suicide? Sacca said, screw it. He wasn’t going to play it traditionally anymore.

Quit playing defense. Play offense.

When Chris Sacca talks about his time living in San Francisco, he says he was always playing defense. His days were full of meetings and coffee meet-ups, hearing pitches that he didn’t really want to hear. Not working on things he wanted to because he was bombarded with appointments and pitches and dinner gatherings. So the move 3 hours away to Truckee gave him an excuse, but it also helped Chris and his wife be more intentional about who they would spend time with.

With the new home in the new location they made another change. They consciously decided who they wanted to spend time with; they made a list. No longer were they spending their days with coffee meet-ups and forced dinner gatherings. Now, they went on the offensive and made a list of people they wanted to spend time with and get to know better. Then, they invited those people to come spend a weekend in Truckee. Go on the offensive. Decide who you want to spend time with and where you want to live that life.

The currencies of the new rich: Time and Mobility.

Understand that time and mobility are currencies just like money. Tim’s entire book, Four Hour Work Week, preaches that message. On the podcast, Tim tells the story of his friend who puts together week-long mastermind seminars for billionaires. It’s a week long event to gather together the uber successful. The irony is that the billionaires can only stay one day. They can’t be gone the whole week. What’s the point of having a billion dollars if you can’t be gone when you want and for as long as you want. The new rich are defined by a more elusive power than simple cash- unrestricted mobility. No matter where you are at now, just understand that there are three currencies. Time and mobility are every bit as valuable as money.

Just do it and correct course along the way.

In the Four Hour Work Week, Tim Ferriss writes, “There’s never a good time to have a baby. For all the most important things, the timing always sucks.” Whether you are talking about starting your own business or planning a two week dream vacation, I go by Tim’s advice. “Conditions are never perfect. ‘Someday’ is a disease that will take your dreams to the grave with you. If it’s important to you and you want to do it ‘eventually,’ just do it and correct course along the way.”

If you don’t prioritize your life, someone else will.

The book Essentialism is all about pausing constantly to ask, “Am I investing in the right activities?” If you don’t prioritize your life, someone else will. McKeown writes, “When we don’t purposely and deliberately choose where to focus our energies and time, other people- our bosses, our colleagues, our clients, and even our families- will choose for us, and before long we’ll have lost sight of everything that is meaningful and important.”

Decide what’s really important.

I respect Chris Sacca because he has determined what’s important and only spends time on those things. And this decision is available to people regardless of income level. Sacca said, “I’ve had to decide what’s really important to me. That’s my wife and my kids. I’m just not that social anymore. I just don’t hang out with people that much. I don’t go to conferences anymore. I’m not available for dinner. I would rather spend that time with them.”

Pastor, speaker, and author Kevin DeYoung

Everything doesn’t depend on you .

In the excellent book Crazy Busy, author and pastor Kevin DeYoung says we overestimate our own importance. It’s easy to get wrapped up thinking, “If I don’t do this, no one will. Everything depends on me.” I have been guilty of this. DeYoung writes, “But the truth is, you’re only indispensable until you say no. You are unique. Your gifts are important. People love you. But you’re not irreplaceable.” You can say no to coaching youth sports, volunteering at school, organizing the fundraiser, etc. As DeYoung writes, “Is it possible that God is not asking me to do anything about sex trafficking right now?” If you are crazy busy, then it’s ok not to be involved. You are unique, but the crazy busy person needs to guard his or her time. Trust that other people with gifts and a concern for sex trafficking are stepping up. You are only indispensable until you say no. DeYoung writes, “We have to be okay with other Christians doing certain good things better and more often than we do.”

It’s somebody else’s turn to do this job.

Kevin DeYoung also mentions an essay entitled , “Why Women Still Can’t Have It All.” Anne-Marie Slaughter, author of the essay, was working for Hillary Clinton at the State Department as the first woman director of policy planning. She quit when she realized she could not be both the professional and the parent she wanted to be. Slaughter writes, “I finally asked myself, ‘Who needs me more?’ And that’s when I realized, it’s somebody else’s turn to do this job. I’m indispensable to my kids, but I’m not close to indispensable to the White House.” DeYoung concludes this part of the book saying, “In the real world of finite time, we often have to discern good and better from best.”

WWE Legend Triple H

Don’t take yourself too seriously.

We overestimate our own importance; we think everyone depends on us. We need to listen to the advice of an icon in his industry who says, “Don’t take yourself too seriously.” Tim Ferriss interviewed WWE Superstar Triple H. Triple H is a wise veteran who rose to the top of his profession and stayed there for numerous years. When Tim asked the 13-time World Champion what advice he would give to his younger self, Triple H said, “Don’t take yourself too seriously.” Valuable advice for WWE Champions and regular folks like me.

Duke Men’s Basketball Coach Mike Krzyzewski

Keep things in perspective.

One of my favorite stories in college athletics comes from Coach K. I watched this press conference live back in 2002. It took some serious internet research to find the exact quote, but Duke Men’s Basketball Coach Mike Krzyzewski imparted some wisdom that I have never forgotten.

In 2002, the Duke Men’s Basketball team was attempting to win back-to-back national championships when they were upset by Indiana in the Regional Semifinal. In the postgame press conference Mike Krzyzewski was asked if he was stunned: “I’m not stunned. I’m 55 and I need a hip replaced. I coach a game where I know we can lose every time we go on the court. Somebody wins, somebody loses. I’m proud of my guys. I love my guys. I’d rather lose with them than win with others, and they have been terrific for me all year. It’s hard for me to be sad about one game when I get the opportunity to work with these kids on a day-to-day basis.”

Admiral McRaven at the commencemetnt speech he gave at the University of Texas

Sometimes, you still end up as a sugar cookie.

We conclude by going back to Admiral McRaven, 38-year veteran of the Navy SEALs, and one of his life lessons he presented to University of Texas graduates in his commencement speech. Here it is, in the words of the Admiral:

Several times a week, instructors would line up the class and do a uniform inspection. It was exceptionally thorough. Your hat had to be perfectly, your uniform immaculately pressed, and your belt buckle shiny and void of any smudges. But it seemed that no matter how much effort you put into starching your hat, or pressing your uniform, or polishing your belt buckle, it just wasn’t good enough. The instructors would find “something” wrong.

For failing the uniform inspection, the student had to run, fully clothed, into the surf-zone and then, wet from head to toe, roll around on the beach until every part of your body was covered with sand. The effect was known as a “sugar cookie.” You stayed in that uniform the rest of the day- cold, wet, and sandy. There were many students who just couldn’t accept the fact that all their effort was in vain. That no matter how hard they tried to get the uniform right, it was unappreciated. Those students didn’t make it through training. Those students didn’t understand the purpose of the drill. You were never going to have a perfect uniform.

Sometimes, no matter how well you prepare or how well you perform, you still end up as a sugar cookie. It’s just the way life is sometimes. If you want to change the world, get over being a sugar cookie and keep moving forward.

In John Wooden’s words, embrace adversity. He would tell you to expect the rough patches and allow them to make you stronger. According to Wooden, “Most worthwhile things in the competitive would come wrapped in adversity.” It’s just the way life is sometimes. No matter how well you prepare or how well you perform, sometimes in life you still end up as a sugar cookie.

Closing Thoughts

Current NFL analyst and former NFL Head Coach Tony Dungy

How will you define success? Former NFL Head Coach and Super Bowl winning coach Tony Dungy writes, “Society tends to define success in terms of accomplishments and awards, material possessions, and profit margins. In the football business, winning is the only thing that matters. God’s Word, however, presents a different definition of success- one centered on a relationship with Jesus Christ and a love for God that allows us to love and serve others. God gives each one of us unique gifts, abilities, and passions. How well we use those qualities to have an impact on the world around determines how ‘successful’ we really are.”

Pastor John Piper

Personally, I want my life to have eternal significance. Pastor John Piper said, “Desire that your life count for something great! Long for your life to have eternal significance. Want this! Don’t coast through life without a passion.”

In Tony Dungy’s book Quiet Strength he wrote, “God’s definition of success is really one of significance- the significant difference our lives can make in the lives of others. This significance doesn’t show up in win-loss records, long resumes, or the trophies gathering dust on our mantel. It’s found in the hearts and lives of those we’ve come across who are in some way better because of the way we lived.”

Thanks for reading- I’m Scott Raymond. I’m a volleyball husband, writer, and avid reader of non-fiction. I write primarily on emerging cities, technology, and horse racing. May 31 I begin a 12 week experiment in the world of software development with The Software Guild. Perhaps our technology and club volleyball life will take us to a new work in Champaign, IL or Atlanta, GA.

You can read more of my work at

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… Or contact me at onehorsestable at gmail dot com

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