about having something stuck in your teeth.

Things I’m learning about having something stuck in your teeth (Day # 12,187)

Last night, I went for a short walk to Harvard Square from the HBS campus and treated myself to dinner at Felipe's, one of my favorite Mexican restaurants in Boston. I ordered a salad with chicken, pico de gallo and extra cilantro. I was sitting alone but the small restaurant was so busy that its patrons were packed in like sardines. I wound up in conversation with a few people sitting at the table next to me. We talked, shared stories, and laughed. On my way out, I smiled at my new friends at the table beside me, at the people preparing food behind the counter, and at many others on the street on my walk home. When I got back to my room on campus, I soon realized that my innocent request for some extra cilantro had unintended consequences.. a quick glance in the mirror highlighted the green garnish that had made its home right in the middle of my two front teeth! Thankfully, I'm pretty good at laughing at myself so the feeling of embarrassment passed relatively quickly, but soon turned to wonder. "Why didn't anyone tell me?”

After I got home from dinner (and flossed my teeth well enough to make any dentist proud), I spent some time with a couple friends in our living group lounge. In this intimate setting, someone who has become a very close friend shared a comment, saying that it seemed I had lost some of the "spark" that he had come to expect from me. The first comment broke the ice, making it easier for the several others who spoke up to agree.

"Is everything ok?"

"Has something changed? You seem different."

Admittedly, it's been a challenging year. In fact, it's been the hardest year of my entire life. When I first met this group of extraordinary humans a year ago, we had come to HBS from all over the world to participate in an education program designed specifically for entrepreneurs like us. I entered the program as the owner of an 8-figure business I had started over 10 years earlier when I was 18 years old; one year later, the unexpected death of my business partner had triggered a bizarre series of events that had consumed my attention and energy completely. The outcome that followed these expensive lessons resulted in my life looking much different from what I had expected. I realized that I had allowed much of my personal identity to be defined by the business, and when that went away this year, I wound up in a pretty vulnerable position.

My relationships with these friends were built on trust, so I knew their comments were coming from a place of care and concern for my well being. That doesn't change the fact that feedback is often difficult to receive. My heart hurt hearing from friends that I had let them down this year by not bringing my full and best self to class and conversation every day.

While receiving feedback can be a little painful, I can't help but think about how silly I must've looked walking around Harvard Square, talking and smiling, completely oblivious to the cilantro in between my front teeth. I admit, be it a friend or a complete stranger, it's a little uncomfortable telling someone "hey, you've got something stuck in your teeth." But in my case, I would've much preferred a quick moment of discomfort to save a whole evening with an extracurricular smile.

As leaders, it can be uncomfortable to give critical feedback to our team members, our partners, or our friends. It may be equally difficult for those on the receiving end. But whether we have something in our teeth or there's some measure of our performance that can be improved - wouldn't you rather know, so you can fix it?

To add complexity, being in a leadership position often leaves us in an extremely vulnerable position. We are responsible for the management and development of our teams, but who is managing and developing us? Are we committed enough to seek out difficult conversations with people to ask for their critical feedback? Who are the people in our lives that we can trust to help us see our blind spots and to highlight the areas requiring our attention so we can continue to grow?

In my experience, giving and seeking feedback is a skill that can be learned with practice. It's natural for us to put off difficult conversations with our people until the problem becomes so large that we can no longer ignore it. I've learned that it's far easier not to wait until that point and instead create a feedback model with increased frequency. It's easier to change course with consistent, incremental corrections.

I've been working on trying to shift my perspective. It's still difficult, but I'm working on viewing my circumstances through a lens of opportunity - I have a chance to reinvent myself, to think hard and design the next chapter of my life with a clean slate. I know that I'm not alone in experiencing setbacks and hard lessons, and I've come to appreciate them as an essential part of my story and an opportunity for growth. Being at a crossroads in this transitional period, I couldn't be more grateful for the network of friends and mentors in my life that aren't afraid to offer me the critical feedback I need to get better and improve myself little by little, every day.

Adapted from an email sent to classmates on Nov 13, 2019.

about leading and following.

Ever since I can remember, I’ve found myself in roles as a leader. It wasn’t anything I planned, but it came so naturally, like it was somehow wired in to my DNA.

As a leader among my neighborhood friends, I was quick to identify the “promised land,” otherwise known as a random spot in the woods that would house our very own BMX bike track. We’d ride our bikes with shovels across the handlebars and spend hours building mounds of dirt from which we’d hurl our young, immortal bodies. In middle school, I become involved in student government, serving as the Student Body President. That continued through high school, where I served a few years as Class President and was selected to represent our school at several leadership camps and local community organizations. At home, a sister with special needs required extra attention from mom, and extra time at work for dad, but ultimately taught us kindness, patience, and selflessness. I found myself in a role of leader and peacemaker, a kind of glue between the 5 kids and a mom and dad who were stretched to superhero lengths just to take care of us. In the community, I became a leader in church groups and other organizations I was involved with. And since before I graduated high school, my entrepreneurial endeavors left me in leadership positions ranging from startup to leading a company with nearly 70 employees, and everything in between.

These roles as a leader have all looked very different on the surface but have shared many of the same responsibilities and required many of the same characteristics. Being a leader comes with a lot of pressure, from sources external and internal. The highs are high, and the lows are low. In this most recent season of my life, I’ve carried a tremendous amount of weight as a leader, from challenges and failure, from new obstacles placed in my path.

My newest and most important leadership role is that of “husband” and that role too comes with a lot of pressure. I’ve been extra hard on myself this year. For one of the first times in my life, I’ve experienced challenges that I’ve been unable to fix. I’ve been down, I’ve been angry, and perhaps most difficult, I’ve felt lost. With big life transitions this year, I learned that I had built a lot of my identity around the people and projects I was invested in. When those things went away, so too did much of my identity. I was left wondering who I was, where I was going, what the point of it all was. This was new for me and I didn’t like it. I recognized that these obstacles were causing me to be less than the best version of myself, but I felt frozen, unable to snap out of it. Unsurprisingly, this only led to more feelings of guilt for not being a better leader and partner for my wife to look to.

Earlier this week, my wife shared a quote from an author she likes named Rachel Hollis, “We have a rule in our relationship— whoever has the better attitude is the leader... and we follow the leader! Whoever is feeling more positive? Leader. Whoever is feeling stronger? Leader. Whoever has stronger faith, bigger dreams, more energy? Leader. The thing is, the leader might flip back and forth several times in a single day or someone might lead out for an entire season while their partner is struggling.”

I really liked this perspective. It was insight that helped me allow myself some grace, for the times when I needed to look elsewhere for a leader to follow. It was especially refreshing to have my eyes opened to the frequency in which those roles can switch. With this in mind, my wife and I consciously switched roles 4 different times on Monday. And we were perfectly ok with that.

This chapter has helped me to learn that it’s ok to look to others as the leader in these moments of difficulty. Important then, to identify the people in our lives who we can trust to look to as leaders in the moments that we need to follow.

about jane at the jewelry store and being a linchpin

things i’m learning about jane at the jewelry store and being a linchpin:

Every day, we go through the motions. We all have some version of our own routines and habits, goals and to-do lists, commitments, obligations, hobbies, and other activities. The reality is that the moments that become our memories, journal entries, and instagram posts don’t happen every day. Most days are simply average.

That’s not to say that we can’t find joy in the activities that an ordinary day requires. We can. But that’s not what I’m writing about today. The fact is that if you’re anything like me, things like running to the grocery store, returning something at Target for my wife, or sneaking enough time to swing through Chipotle between meetings are rarely events that any of us would describe as inspiring or enjoyable.

But, why not?

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I had an incredibly hard working team member named Darren who worked for my custom apparel company. He worked in our Nashville screen printing production facility, where the long Tennessee summers made our shop (and subsequently, many of our team members) miserably hot and understandably uncomfortable. On the very hottest summer days that the 615 area code threw our way, it wasn’t uncommon for some to publicly announce their feelings, call in sick, or otherwise make it known that they weren’t excited to be at work. In stark contrast, Darren remained a steadfast example of humility, hard work, and kindness no matter the temperature the mercury climbed to on the barometer.

Darren taught me a lot. While my position on the company org chart technically meant our team members looked up to my position, in fact it was me who looked up to him with tremendous respect. I learned a lot from Darren as he taught all of us many lessons in leadership; perhaps my favorite of all of them was a casual phrase that he used regularly, not only in conversation, but his actions. It was almost as if it were a compass that guides his life and decision making: “Do it with excellence.”

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Before my wife said “yes” when I presented her with a tiny, shiny circle housed inside a recognizably blue cardboard box, I had the experience of visiting countless jewelry stores in search of “the perfect one.” Anyone who’s ever gone jewelry shopping can likely relate to the miserable process such a task requires one to endure. (If you’ve never bought an engagement ring, then just imagine the last time you went furniture shopping and you’ll know what I mean). Like vultures to a catch, the sales people were unanimously overwhelming and overbearing from my first step inside the door. They didn’t listen. They didn’t ask meaningful questions. They didn’t care about me, my elaborate plan to propose in front of the Eiffel Tower in Paris, or any details I tried to share about what I was looking for. They simply were after a sale.

And then there was Jane.

Like an angel appearing in the middle of a chain store in Green Hills, TN, her entrance will forever be etched in my memory as a heavenly experience, not visibly, but emotionally so. As circumstance would have it, I had already found the perfect ring at another store. Communicating that up front, I expected her to move along and help another customer who might actually be purchasing something expensive enough to merit a big sales commission. It seemed to prompt the opposite - she asked meaningful and sincere questions with genuine curiosity, wanting to know all about the special girl who had me running all over town, where we met, the plan for the proposal, and even the ring.. that I bought somewhere else. Upon discovering I had it with me in the car, she begged me to run and grab it so she could see how beautiful it was. A quick round trip to the parking lot and back led to another unexpected moment, when she inspected it carefully and asked to excuse herself for a couple minutes so she could professionally clean and polish until the presentation would sparkle to her high standard of excellence when exposed for the first time under the lights of Paris.

Jane never asked for anything. She didn’t even try to give me a business card for future purchases. She took every opportunity to add value at every turn, offering delight and surprise, selflessly.

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Seth Godin, a brilliant writer + thinker, has a name for the kind of people who do their work and live their lives this way - _Linchpin_ (in his book of the same name). He challenges us to become “indispensable” - to make ourselves more valuable by consistently finding ways to add value to the lives of others.

I was reminded of my positive experience with Jane at the jewelry store yesterday while ordering lunch in Utah. At a fast casual restaurant concept called Costa Vida, I was pleasantly surprised by a friendly greeting from behind the counter. This was more than just an enthusiastic “hi!” - there was a sincerity and intention in his voice that I heard echo throughout the cafe as each new person stepped forward to place their order. Watching the man with “Arturo” on his name tag proceed through the lunch rush, preparing food for customers, jumping in to support his teammates, and never missing a beat. His moves were quick, but calculated. Full of both vigor and craftsmanship, quality and excellence.

After eating my lunch, the rush had dissipated, so on my way out I stopped to pay a compliment to Arturo, to let him know I appreciated the way he did his job with excellence and care for both the customers and teammates. I thanked him for such a positive experience and reflected on the way that he was able to transform such an ordinary experience in to an extraordinary one.

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Therein lies the opportunity that we all have - the secret that Jane and Seth Godin and Arturo have already figured out is that we can _choose_ to sell jewelry, print t-shirts, write books, or prepare taco salads - with excellence. We can choose to follow the status quo, or we can choose to redefine it. And the best part is that we can start now. And if we screw it up today, we can choose to try again tomorrow. We can be ordinary people doing extraordinary things.

about being angry.

Things I'm learning about being angry:

It's been a difficult season in my life. The past 18 months or so have been full of ups and downs - not just the kind we experience everyday, but ones of a much greater scale. The kinds of highs and lows that are life altering, that have an impact on many lives other than just my own. From challenges surrounding a struggling business that required many difficult decisions, to the no brainer decision to marry my best friend and companion. From seemingly unsolvable problems in a challenging business relationship, to the unexpected passing of a business partner and the many challenges that followed. Through this period, I experienced such a potent cocktail of different emotions that for the first time in my life I felt unable to control them. I've typically been pretty level headed and able to keep my cool (thanks, Dad), and have never had much issue with pulling myself quickly out of negative emotions. But these drastic swings left me paralyzed at times. Lacking the ability to simply decide to no longer feel sad or angry, I was forced to sit with these emotions. Not to sulk, but to process. Not to quit seeking solutions to change the things that were making me unhappy, but rather to simply feel and experience those emotions. To recognize them for exactly what they were. To own them.

My little sister, Kelsey, had a favorite book when she was young. Appropriately titled, "I Was So Mad" the book told the story of Little Critter on a day that just wasn't going his way. Each new page introduced something else that was frustrating for Little Critter, to which he'd respond, "I Was So Mad." Finally, he's had enough. He decides to pack his things and run away. Fate would have it that just as he was leaving, Radio-Flyer Wagon packed, he bumps in to friends who were coming to ask him to come to the park. When his mom responds yes to him asking to go, the book concludes with Little Critter deciding, "I'll run away tomorrow, if I'm still so mad."

This book was a fitting favorite for my sweet sister Kelsey, because at the time she wasn't always so sweet. Those toddler years were rough on poor Kelsey, and just like the character in the book, there were a lot of things that made her mad when they didn't go her way.

During this period, more than any other time in my life, there have been times when I just needed to be mad. When circumstances were such that I was feeling angry, or sad, or disappointed, rather than my default behavior of trying to pull myself out of feeling that way as quickly as possible, I instead recognized the emotion and then allowed myself time to feel and experience it. It's honestly been a rewarding experience. It seems counterintuitive - what good could possibly come from letting yourself be angry? What does that even look like? I imagine it's a little different for everyone. It may mean sitting alone in a quiet room for some, or blasting loud punk rock music to someone else. Maybe it's going to the gym or going outside for a run to burn off some steam, or maybe it's just calling someone you care about to vent. For me, it's mostly just time. Time to think. Time to process. Time to heal. I didn't fully understand this about myself until getting married. It took me having to recognize my need, and then learning to communicate that to my wife. My first couple attempts were awkward, uncomfortable. It felt silly to be a grown man explaining to my sweet new wife that I was upset, and that I needed her to let me STAY upset. I didn't want her to try to cheer me up, because I know myself well enough to know that wouldn't help. I just had to learn to communicate clearly that I was feeling a certain emotion and that I needed her to allow me to feel it, while making sure to overemphasize that it had nothing to do with her or our relationship and that I didn't want my sour mood to spill over to affect her. Usually, I'll sleep it off and wake up the next day feeling back to normal. For you it may look different. But I'd like to challenge you to try to recognize your needs, and practice communicating that to someone else. I think it's important to get to know ourselves better as we identify how we process these difficult emotions, and equally important to learn how to explain and communicate our needs to our families, friends, co-workers, or other important people in our lives.

This season has helped me to learn the importance of ALL that life throws at us: the good and the bad; the happy and the sad; the rainy days just as well as the sunny ones. It's kind of like catching a bad cold or the flu - a few days of feeling completely miserable can sure help to extend the depth of our gratitude for good health.

To be clear - I believe there is a fine line between a healthy way of processing these difficult emotions and an unhealthy one. Anger, sadness, or disappointment are certainly not emotions that we're meant to endure forever, and it can quickly lose any opportunity to be a rewarding process when taken too far. I think it takes intention and discipline to identify and recognize these things for what they are, allow ourselves to feel them, and then to move on.

I've gained a new appreciation and understanding for a remarkable quote offered by Teddy Roosevelt, "Far better it is to dare mighty things, to win glorious triumphs, even though checkered by failure, than to rank with those poor spirits who neither enjoy much nor suffer much, because they live in that grey twilight that knows neither victory nor defeat."

about tennis and tim mcgraw

Things I’m learning about tennis and Tim McGraw:

I played a game of tennis with my new friend Fabio yesterday. I’m a beginner (at best). Fabio is not.

I tried my best to keep up, but felt a little silly making so many mistakes. It was more than once that I swung for the ball and missed it completely! I felt like a baseball player at bat and striking out. The only difference: my tennis racket has a surface area of 98 square inches while a baseball bat.. doesn’t.

Fabio was friendly and patient. Even when he was taking it easy on me, I could see that his technique was excellent. Great form, great execution. I knew I could learn from a great player like him, so on a short break I asked if he had any tips for me. He smiled and quietly said, “Keep your eye on the ball.”

“Keep your eye on the ball?” I thought to myself. I was expecting he might suggest corrections to my form, or teach me some secret way to hit the ball to increase power or make it spin like the pros. Instead, he offered advice that some might interpret as elementary, at best. He used a total of six words, and managed to keep me thinking for the rest of the day.


My favorite Tim McGraw song offers similar advice.

Hold the door, say "please", say "thank you" Don't steal, don't cheat, and don't lie I know you got mountains to climb But always stay humble and kind

Penned by songwriter Lori McKenna, “Humble and Kind” demonstrates the power of a simple lyric.

Go to church 'cause your mamma says to Visit grandpa every chance that you can It won't be wasted time Always stay humble and kind

At different points in my life, I’ve found different words and phrases stand out in particularly meaningful ways. It’s remarkable to me how so many valuable life lessons can be packed in to each line.

When the dreams you're dreamin' come to you When the work you put in is realized Let yourself feel the pride But always stay humble and kind

A particular example: one morning on a drive back to work from a meeting, I got an important piece of advice from one line in the song I hadn’t previously paid much attention to. I wouldn’t consider myself a person who holds grudges. I tend to be quick to forgive others and move on, at times maybe too quick. This particular morning when I heard the line “bitterness keeps you from flyin’” it struck me in a whole new way.

Don't expect a free ride from no one Don't hold a grudge or a chip and here's why: Bitterness keeps you from flyin' Always stay humble and kind

During a period where I ended up on the short end of a couple deals in a row, I had grown increasingly frustrated, not only with the music business, but with myself. I chose not to pursue an aggressive legal strategy I could’ve taken at the time, and I thought that meant I was taking the high road. What I didn’t realize is that the bitterness I was still holding on to was holding me back. I was letting the actions of others prevent me from being the best version of myself.

To borrow a silly analogy from one of the best people I’ve ever met (shout out to Mark @ HOBY Georgia), “it’s hard to soar like an eagle when you’re surrounded by turkeys.”

I felt like I was taking the “high road” by not filling lawsuits. But even the high road is still on the ground. By being bitter, I was only holding myself back from flyin’ - from being an authentic leader; from being remarkable.


“Keep your eye on the ball.”

A small handful of people in my life know that I’m back at school. I’ve just started an extraordinary learning program that span 3 years, and the application criteria was strategically architected in a way that fills these classrooms with global leaders, CEO’s, and entrepreneurs.

Utilizing the case study method, our professors have designed cases with seemingly recurring themes. Focus, refine, test, measure, iterate, remove. We’re being challenged to analyze both the cases and our own businesses and processes, forced to think critically and determine the things that are actually working. The things that we do well, and the things we don’t.

How often do we, as humans, as creatives, as business leaders, tend to overcomplicate things?

I struggle with spreading myself too thin. There’s so much I want to accomplish in life, that I want to achieve and create and experience. I’m constantly looking ahead to what’s next.

I learned yesterday that it’s certainly not a bad thing to be looking ahead, to be constantly planning our next shots. But let us not forget the basics. Remember to identify and keep your eye on the things that are most important. “Keep your eye on the ball.”


Don't take for granted the love this life gives you When you get where you're going don't forget turn back around And help the next one in line Always stay humble and kind

about cold water, regret, and your brain.

Have you ever jumped in cold water? Been forced to take a cold shower when the rest of your family or roommates used up all the hot water?

Growing up in the Seattle area, a favorite family activity was boating. I grew up with a hero (aka: dad) who’d often go for slalom ski runs on the lake before work. I followed suit, during a time when wakeboarding was a brand new and relatively unknown sport.

The lakes in the Pacific Northwest are beautiful. The only problem is the moderate climate means the lake water hardly warms up, even in the peak of the summer. For a period, we were wakeboarding year round, hacking ways to beat the cold temperatures with a combination of dry suit technology, gloves, and coolers full of hot water.

The feeling of jumping in to Seattle lake water is forever etched in my memory. A more extreme shock in January than in June, certainly, but I have to admit that even in the early summer months the water will still take your breath away when you jump in.

It’s really an uncomfortable feeling. It’s not fun. As a teenager, I’d go out with my dad and friends and we’d help psyche each other and ourselves up for the challenge, knowing how much fun we’d have once we got through that initial discomfort. Even then, it took commitment to make that leap.

If you’ve ever had a similar experience, I’m sure you’d agree that initial shock is really not enjoyable. But did you ever notice how awake and alive you feel after?

That’s not a coincidence.

I’ve spent a lot of time this past year studying the brain, primarily to learn new ways to optimize my performance, energy, and overall health. Every living thing is made of cells. Our cells are powered by our mitochondria: organelles responsible for generating our energy. That jolt from jumping in cold water is actually good for mitochondrial function. The more we can optimize our mitochondrial performance, the more energy we’ll have.

Research shows the same is true of other kinds of fear.

As we’re able to identify the things which we’re afraid of (step 1, but often disguised), and then choose to face those things head on, our mitochondria respond with improved function. Can you remember a time you intentionally did something, no matter how small that thing is, that you were afraid of? Do you remember how you felt after? I’d bet you didn’t regret doing that thing you were afraid of.

You gain strength, courage and confidence by every experience in which you really stop to look fear in the face. You are able to say to yourself, ‘I have lived through this horror. I can take the next thing that comes along.’ You must do the thing you think you cannot do.
— Eleanor Roosevelt

I went to a family reunion last week. My cousin owns a beautiful home on the Columbia River in Eastern Washington and is kind enough to let our unreasonably large extended family enjoy it for reunions. This was the first reunion I’ve been to since I moved to Nashville in 2012, so I got to see cousins and family I hadn’t seen in 6 years and longer. We had three boats out there with any combination of toys and watersports equipment you could dream of.

Having enjoyed owning a boat in Nashville the last several years, I’ll be the first to admit I’ve gotten used to the bathtub water temperatures we enjoy in lakes in the South. It’s not uncommon for the water temperatures to be between 85-88 degrees all summer. So when I dipped my toe in that River water in Washington and looked at the 65 degree water temperature reading, I decided I’d be too cold to get in and spent 3 days in the comfort of my dry clothes.

I didn’t mind at the time. I didn’t feel left out and had a great time. But now that I’m back in Nashville and have a few minutes to reflect, I really regret NOT jumping in. Not because I particularly wanted to jump on a tube or catch a ride behind the boat. But because I don’t know the next time I’ll be able to go to another reunion. What if it’s another 6 years? I wish I would’ve taken the opportunity to jump in and swim around with my dad and my sisters. That cold water would’ve been a little painful and uncomfortable for a minute, sure. But more painful is the feeling of regret I have now, wondering how long it will be until the next time we’re all together as a family again. I’m reminded of a favorite saying (italics mine),

Twenty years from now you will be more disappointed by the things that you *didn’t* do than by the ones you *did* so. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.
— Mark Twain^1

So get out there. Sail away from your safe harbor and jump on in. Find something that makes you feel scared. Then, choose to conquer it. Your brain just might work a little better after.

[1]: Commonly attributed, perhaps incorrectly, to Mark Twain.

about your annoying little brother or sister

about your annoying little brother or sister.

things i’m learning about your annoying little brother and/or sister:

If you grew up with younger siblings, you might remember your little brother or sister doing things that would annoy you. Let me know if this sounds familiar:

“Kelsey, put your toys away.”

“Why?”

“Because you have a zillion polly pockets and you can’t just leave them all over the house.”

“Why?”

“Because if you do mom is gonna yell at you.”

“Why?”

“Because it stresses her out when the house is a disaster and she has a million other things to do.”

“Why?”

… you get the point. Imagine hearing that from this little monster:

We probably all remember that lovely little trick where they’d respond to anything you said with “Why?” And with every answer, they ‘d respond with another “Why?” as an increasingly annoying challenge to dig further and deeper to find an answer that would finally make them shut up… Of course in the most annoying way possible. Asking “why?” is seemingly an annoying talent that most little brothers or sisters tend to have a boundless supply of.

As much as we might hate to admit it, we might be able to learn something from our annoying younger siblings.

As I use the same exercise to dig deep and challenge myself daily, I have interesting results. As I probe deeper into the layers of my internal thoughts, subsequent actions, my habits and routines by constantly asking myself “why” I find that I can learn a lot about myself. Pushing through those layers of “why” can help identify strengths, weaknesses, blind spots, opportunities, and more. It helps me understand the perspectives, decisions, and actions of others too.

As I ask “why” throughout the day, every day, and as I constantly review and iterate, I can find the root causes of certain behaviors that I can then hack or modify for my own benefit.

When you really learn why you are or aren’t doing something by identifying the root cause, then you can figure out how to fix it. You can enlist the help of others. You can modify your own habits and way of thinking to change.

You might want to shoot your little brother or sister a text message today. Tell them thank you for being annoying.

Ask why.


Don’t worry, the girls and I turned out alright :)


about shawn kemp and gary payton

about shawn kemp

Things I’m learning about Shawn Kemp: that he’s awesome, obviously. I’ve clearly known that since the early 90's.

believe it or not, i still have that seattle supersonics jersey.

But beyond that, I’m learning that his teammate, Gary Payton, made him better.

If you’re not a Sonics fan, how about John Stockton and Karl Malone? Michael Jordan and Bugs Bunny?

I loved basketball when I was a kid. We had a CD-Rom with stats and facts of all the key players in the league that I studied and memorized until I knew most of them by heart. I had the shoes, the jersey, the swagger (reference 1st picture in this post for proof). I was certain that I was going to grow up to become an NBA basketball player.

Study that photo of my friends and I at my 7th birthday party one more time and you might notice that most of them are a full head taller than me. As fate would have it, that trend continued with time, until I was cut from the team and told I was too short to be an asset.

So, what’s the lesson to learn here? Never give up, refuse to take no for an answer, don’t stop until you achieve your dreams? As much as I loved the movie Rudy as a kid, that’s not how my story ended. I did give up. Because sometimes our dreams just aren’t realistic. Sometimes they’re the wrong dreams, sometimes we change, and sometimes they’re just plain silly. It’s ok to change our dreams as we grow and change ourselves. Heck, before I wanted to play in the NBA, I thought I wanted to be a Ninja Turtle, and that one didn’t exactly work out either.

The lesson here is a case study in teamwork and in partnerships. We’ll look at one of the most remarkable duos of all time. They filled headlines and highlight reels throughout the 90’s, and they gave kids like me a reason to wear their jerseys with pride.

Shawn Kemp was one of the most exciting basketball players to set foot on the hardwood. He was a star in high school, breaking both single game and season-long scoring records. He was a High School All-American, playing for the class of ’88 (arguably one of the best All-American classes of all time), and then became a first-round draft pick in the ’89 draft without playing in college, which was very uncommon at the time. Nicknamed the “Reign Man,” he played with a level of intensity, power, and excitement that made his presence known in every game.

Enter: “The Glove.” Gary Payton was the 2nd overall draft pick in 1990. Many consider him one of the greatest point guards of all time. His quick hands earned him the NBA Defensive Player of the Year award, the only point guard in history to do so. His abilities and playing style (+ his indisputable gift for trash talking) were the perfect complement to the aggressive, powerful Shawn Kemp. Together, they were dubbed the Sonic Boom.

A quick youtube search illustrates this well.

As individuals, Shawn Kemp and Gary Payton were great players. Together, they were extraordinary.

Their complimentary talents made the other better. It turns out that sometimes 1+1=3. The sum is greater than the individual parts.

I’m learning that these same principles apply off the court as well.

I’ve experienced the magic that happens when you get this right, and I’ve experienced the absolutely disasterous consequences that come as a result of getting this wrong. I’ve felt the natural chemistry of a great team, where the projects and the people are in alignment and elevate one another, to grow in ways they never could alone. I’ve also felt the friction and frustration that can cause things to fall apart.

Through analysis and reflection of my experiences, I’ve learned how powerful it is to first know yourself, very very well. Your strengths, and your weaknesses. Your desired outcomes. Your shoulds and your musts. Your own mission, your own values, your own principles, by which you will conduct your own behavior, make decisions and treat people. Your definition of success. Your good, better, and best, as well as your not-acceptable.

Then, be that person. With a renewed vision and understanding of the kind of team you want to be a part of, you can lead and act and communicate and treat people and make decisions the way you expect of yourself and your team. In my experience, this can naturally attract the kind of people/clients/friends/partners/bosses/employees/etc that you will be in alignment with.

As I’ve worked to figure that out, my result has been clarity. As I’ve identified and defined these things about myself, I’ve seen how much easier it becomes to know where I’m going, how I’m going to get there, and who I want along for the ride.

I’ve learned the importance of having the right people on the bus, the wrong people off the bus, and the right people in the right seats.

about being good at everything.

Things I’m learning about being good at everything:

It can mean that you’re not great at anything.

Is that a bad thing? Not necessarily.

I’m sure we all grew up knowing someone who was good. at. everything.

Here’s one example: The kid in high school who played every sport, made straight A’s, and was loved by teachers and students alike.

Here’s another: There’s not been a single person I’ve seen my grandpa struggle to engage in conversation with. He is an incredibly smart man, and he knows at least enough about seemingly every topic in the world to carry on a conversation. It’s a quality I’ve always really admired about him.

The alternative example may be those who focus and specialize in one thing, and who commit with such discipline and excellence that they become extraordinary. A world class athlete, musician, listener, friend, nurse, dentist, humanitarian, researcher, educator, martial artist.. you get the picture.

I fall more in the first category and that’s where I’m naturally wired to be. I know that it sometimes get me in to trouble, when I want to learn or know or do too many things at once because they’re all so interesting to me. I’m learning what the balance looks like for me, and that is probably necessary for all of us, no matter if you fall somewhere between these categories or somewhere else completely.

I’m of the opinion that, like most things in life, we need to find our own balance. Equilibrium and alignment are an ongoing process and journey.

about asking lots of questions

Things I’m learning about asking lots of questions:

I’ve found it’s a pretty good way to live life.

Becoming excellent at asking the right questions can be a powerful tool, used to learn, communicate ideas, connect with others, and build relationships.

Asking questions provides an opportunity to understand your: peers, customers, bosses, employees, parents, children, friends, enemies, competition, partners, and more.

I’ve learned that asking questions with an authentic and intentional purpose of understanding and clarity is important enough to me to merit practicing regularly.

With flawless execution, asking questions can even be an opportunity to help others understand themselves.

about a michael jordan rookie card.

things i’m learning about a michael jordan rookie card: don’t forget to flip it over.

Let me explain.


As a kid, I collected trading cards. I loved looking at the pictures of my favorite players, with their names printed on the front and all their stats printed on the back. I’d study and memorize the player’s details, from their birthday and hometown to where they played in college, along with key stats about their performance in the league.

My friends displayed their most valuable cards in protective cases, showcasing the pictures on the front but I was always more excited about what was on the back.

Arguably the single most important basketball card among the collector community is the 1986–1987 Fleer Michael Jordan Rookie Card.

The photograph captures the essence of MJ in his signature pose. The timeless Fleer logo overlay is complemented by the player’s name, his position, and the team he plays for. Here’s what you’ll see when you flip it over:

On the front is a familiar picture, but when we flip it over, we find more information: specific statistics that can help us learn what kind of player they are. In basketball, a great team needs a mix of players with different strengths: the top scorers need a teammate with vision to orchestrate the perfect pass, taking in to account timing and placement of the ball (that stat is called an “assist”); also essential are those players who play great defense (“steals”), rebound aggressively, and block shots.


In life, we have different kinds of teams to consider. At home, our families. At work, internal teams of co-workers and external teams of partners, clients, and other stakeholders. In our communities, teams come together in neighborhoods, church congregations, sports teams, and around other activities we participate in.

When working with our team members, how often do we flip the card over?

How much do we really know about each other? How often are we looking holistically at our team’s combined mix of strengths? Can we expect to play and win together when we don’t know who’s playing on our team?


As a solution to this problem in my own life, I dreamed up a way to dig deeper to really understand my teammates. I started with myself. As I found ways to identify and communicate my own strengths and style, I was able to create a framework to implement this with other teams I’m a part of.

I call it, appropriately, The Fleer Framework. I like using a kanban tool such as Trello, but you can use other tools/apps to implement this concept as well. Analog (ie: post-it notes) works well too.

Depending on the kind of team you’re trying to manage, you can choose to include different stats for each player.

A photo with name, title, general contact info is standard. I like including the results from the Gallup StrengthsFinder test (top 5 strengths), as well as the Kolbe A Index, which is used to identify an individual’s natural talents and the instinctive method of operation (M.O.) that enable a person to be productive (ie: HOW we work and solve problems).

Including a personal mission statement and core values helps promote alignment, and including a “currently working on” can be great to keep track of priorities and initiatives. A fun fact keeps it playful and reminds us that we’re humans :)

I intentionally designed a place for each person to list the areas/projects/roles they’re an expert in, starting with the phrase: “I can help you with.”

For larger or more hectic teams, you can utilize Trello’s “labels” feature to code your card with a color: green for available to help, yellow when you’re available for quick questions or feedback, and red when you’re fully committed to a project or initiative.

about knowing what you want.

Things I’m learning about knowing what you want:

There’s a lot of people in life who don’t.

That can be dangerous.

Beyond ourselves, consider: clients, partners, friends, stakeholders, team members. Have you ever met or worked with someone who seemed impossible to please? An unhappy customer, boss, or significant other?

Were expectations communicated clearly, or were there assumptions made, details ambiguous? If the former, we may be in the wrong. If the latter, well, we may also be wrong.

How can you hope to please someone who doesn’t know what they’re after?

I’ve learned that it’s far easier to lean in to that problem, to anticipate it. I’d much prefer to expect and plan for it than the alternative.

As I’ve done so, it’s been a rewarding experience to work on clarifying my processes and to think strategically regarding this optimization problem.

Know what you want (and what you don’t). Communicate this clearly and frequently. Anticipate that other’s won’t. I believe this is an essential skill; a prerequisite to becoming a truly extraordinary leader. As such, that means it can be learned and can be practiced. Like many things, practice makes perfect.