Overcoming Performance Anxiety

I’ve always had a crippling fear of performing in front of people, which is funny because my dream as a teen was to be a rock star. Delusional teenage Kevin even bought a cheap Les Paul knock-off guitar to fulfill this dream. Inexpensive guitars today are pretty awesome, but back in the ‘70s, cheap guitars were horrible instruments — mine was no exception. After years of lessons on a clunky guitar, my skills improved at a snail’s pace and I never felt I was good enough to play for anyone. When I started college and found I had more natural skills for writing computer software than music, I discarded my dreams of touring and playing in a band.

Twenty years later, I owned a better guitar and tried to get back into playing, but never got much traction. Even paying for lessons failed to get me focused enough to practice daily. Having no goals or any hope of being able to play for anyone but myself, I drifted away from the guitar again.

Fast forward to 2014, my move to San Francisco put me in an apartment just two downhill blocks away from the Van Ness Guitar Center. While browsing the guitar section one day, I was convinced to sign up for lessons by a store promotion. The instructor they assigned me turned out to be a great match. Like me, he was a fan of blues/rock guitar and taught me techniques used by Jimi Hendrix and Stevie Ray Vaughan — two of my guitar heroes. After a few weeks of lessons, he said, “You should go to an open mic night at a blues bar and just get up on stage to play riffs with the band.” My response was, “Do you even know me?! I can’t play in front of you as well as I do alone in practice! There’s no way I can handle an audience.”

After a couple of years, my teacher went on tour and I had to switch instructors. As the weeks passed, I found that I was enjoying learning guitar more from YouTube. As an added bonus, this also eliminated my anxiety about performing in front of my teacher. I dropped my single, in-person instructor and added three or four online replacements.

It only made sense to use YouTube for learning guitar, since I already had been watching various channels to learn more about tasting whisky. In three years, I went from barely knowing about whisky, to being a resource for friends on what whiskies to buy. During that same time, my guitar skills ramped up to the point where I didn’t feel guilty about buying a proper guitar and amp setup. Slowly, my confidence on the fretboard was improving as well.

Then around the middle of 2019, I came up with an idea: What if I started a YouTube channel that somehow incorporated my two favorite hobbies? Can I blend drinking whisky and playing guitar in a way that people would tune in and watch?

I came up with the name Whisky Riffs and immediately grabbed the domain. I recorded a couple of videos to see if I could overcome my fear of playing guitar in front of an audience. After posting those to my new channel, I let it gather dust for several months. I wasn’t ready to commit to regular episodes.

It took me until the end of December to decide to go all in. Within a week of making that decision, I learned how to set up lighting, audio, and use my iPhone to record quality videos. My iPad Pro would serve as my editing rig. After a few test recordings, I posted my first episode.

Whisky Riffs Episode 1: Ardbeg Uigeadail Islay Single Malt Scotch Whisky

Whisky Riffs was happening, but now I was committed to weekly episodes. My first goal was to get to 100 subscribers, so I could pick my own YouTube channel name. That happed on January 23 — just three weeks in — and provided the momentum I needed to plow forward. I set a goal to keep improving my channel and process with each video: better riffs, more polished recordings, and faster editing skills.

Recently, I posted episode 16. That’s incredibly satisfying, given that my first episode was posted just 14 weeks earlier. I have consistently posted an episode each week, plus a couple of bonus episodes. My performance anxiety isn’t gone, but my commitment to pushing out regular videos keeps it in check. Every week, I have to give myself a pep talk to turn on the camera and face the bright LED lights. The way I end my intro to every video is as much for me as it is my viewers:

Let’s do this…

Whisky Riffs Episode 16: Laphroaig Lore Islay Single Malt Scotch Whisky

And if you aren’t already a subscriber but are enjoying my videos, please visit Whisky Riffs and Subscribe. Cheers!

2017: A Good Year for Me

There was a lot to be angry and sad about during 2017, but I can’t afford to start a new year focusing on the negatives. Life is just too short to waste time on the darkness. Instead, I’m going to begin 2018 by reflecting on the positives over the last 12 months.

Judy and I welcomed in 2017 by watching the fireworks in London with a couple hundred thousand of strangers and it was glorious. It was even better to spend time with Scotty and his lovely wife and get the grand tour of Tetbury, England.

We continued that trip by spending the first week of January wandering Paris and enjoying all the history, sites, and food in that beautiful city.

Dining in Paris

In April, after months of dedication to practice and lessons, I decided it was time to invest in a new guitar for the first time in over 20 years. I liked my new Fender Strat so much, that I went crazy just three months later and bought an Ovation acoustic to go along with it. As it turns out, when you have instruments that are fun to play, you actually spend more time using them.

Another hobby that I got serious about was learning to taste and appreciate whisky. It’s been a fascinating trip digging into the origins of Scotch, bourbon, Japanese, and other variations of this golden liquid. And all these years I just thought it was just a tool to keep up with my Aussie pals when closing down San Francisco bars.

The Beginnings of My Whisky Collection

At the end of the Summer, Judy, Patch, and I took a trip to Texas to visit our family and friends in Austin and Houston. In fact, much of 2017 was about connecting with loved ones and there can never be enough of that in my life. I’m blessed to have so many people who care about me and for that I’m very thankful.

My sisters, mother, and me

In September, we took another trip overseas to Italy. Judy and I had never been to Rome or Florence, so we did a deep dive into these ancient cities and fell in love with both. Thanks to friends who gave us plenty of tips, we made the most of our week there.

The Colosseum in Rome

For Thanksgiving, I made a solo trip to Austin and Houston to spend the holiday with two-thirds of my kids and give thanks with my sisters and 93-year old mom.

With my two Austin kids

We wrapped up our year by flying in our Austin kids and spending Christmas in Yosemite—all five of us sharing one hotel room. The views were breathtaking and the time with our adult children was precious.

Our family in Yosemite

Thanks, 2017. For all your rough spots, I can’t complain about what you allowed me to accomplish.

Rise Above

Judy and I saw Hidden Figures today and it drove home just how important it is to stay vigilant to inequality and injustice. It made me cringe to see the rights of women and minorities trampled as recently as the 1960s—a decade of my youth. That movie was especially poignant on a day filled with impressive attendance at all the women’s marches around our country and the world.

When I see that I need to make a change in my behavior, I focus on making a change. This rarely coincides with traditional New Year’s resolutions, but this year was different. On Dec. 31 I tweeted that I wasn’t going to continue to retweet negative political posts but focus on positive action instead. My reasoning for this was simple: I need to make a difference instead of merely generating more noise on social networks. Although posting a tweet is technically an action, it’s not one that’s going to change the world. My tweets are me preaching to a choir of like-minded followers. The few that dissent are not going to be swayed by my 140-character posts.

Women’s March in Washington D.C.

Actions that can change the world are the peaceful protests by millions of people who marched the day after the inauguration. Their efforts sent a strong and loud message to our government that women’s rights matter along with other rights. What a marvelous outpouring of positive energy and solidarity. These protests also showed off the best use for Twitter: Pictures and movies of the marches that set a very high bar for how we should spend the next four years.

Unfortunately, most of us—and I’m including myself—have been rolling around in the muck. Every time we comment about Trump’s fake tan or small hands or unique hair style, we waste our time on petty name calling. You know who likes to mock people for their flaws? Trump.

We need to be better than him. When we drop to his level, we become fodder for his followers to point at us and say, “All they do is focus on superficial issues while our leader is trying to Make America Great Again.” Don’t feed the trolls.

It’s going to be a long four-year fight and we have much work to do. There are too many government programs in peril and people who need to be protected. The attacks on our democracy have already started. Our new executive office is spreading lies and threatening the press. We can’t let any of this continue without pushback.

Our fight needs to be for truth. Our fight needs to be focused on standing up for people. We can’t play schoolyard games and call people names. Rise above this bullshit and be better than Trump and his kakistocracy. Let’s do our homework and make sure that everything we post is legit. Lies spread by Trump and his people need to be put under a bright light and exposed. We need to be the light, but we can’t be that when we are being petty.

We also need the support of the free press. It’s been years since I’ve had a newspaper subscription, but I recently subscribed to The New York Times. It’s our job to keep the press honest as well. Force them to use blunt language and to call out lies with clear and direct headlines. The Trump administration is using classic disinformation techniques to bury the truth and keep people from believing that there are even any facts or proof that can be trusted. This battle won’t be won on Twitter. It needs a broader reach with more detailed reporting.

If you have a website, use it. Write more words than you can fit into a tweet. Call out injustice and hold your House and Senate representatives responsible for their actions and their voting. This is a marathon, not a sprint. Even if Trump somehow gets impeached or steps down, the layers of horrible leadership run deep.

As painful as this presidential transition has been, maybe this is what we needed. I know that this has forced me down from my apolitical pedestal and made me think more about state and local politics. Our country has shown that millions care enough to step out and speak up. If it takes a nightmare to wake up more of us, then let’s make the most of this new dawn.

Also available on Medium.

Real Power

I’m not at all happy with how our 2016 national elections turned out, but what’s done is done and we have to move forward.

I can move forward with hope because I know that the person who holds the executive office of the United States of America only has so much power to affect my world. The real power to affect change is in my hands—all of our hands.

Here’s a little secret that you may not know: Government doesn’t create change, it bows to it.

Every important change in our country has come from the people making a decision to do things differently and then pushing for the government to ratify that change. Politicians don’t act, they react. They know that they have to do what their constituents demand or they will no longer hold a seat of power.

If you have been sitting back waiting for the government to fix your problems… wake up. The only person with any power to affect long-term change in your life is you. So forget about who won or lost and who was on what team. Change starts with each and every one of us deciding to make this a better world. And the best place to begin to make a difference is locally in our own communities.

Real power is feeding the hungry.

Real power is sheltering the homeless.

Real power is speaking out for those who are being oppressed.

Real power is learning to embrace change and growth.

Real power is choosing to walk away from hatred and finding a way to love everyone.

Pointing fingers and playing the blame game is easy; we can do that with almost zero effort. It’s harder to take responsibility for change in our lives because we have to actually do something. It’s disruptive to our routines. But with how divided our country is on politics, we can’t afford to sit back and blame others.

Let’s all find one positive thing to change each and every day of our lives. Let’s show the world that we can be better than we were in this past election cycle. The real power is still undecided. It’s time to vote with our actions.

Taking Risks

This article is for my children. It will probably be ignored, as is most parental advice, but I need at least to do my part to communicate the power of taking risks in life.

How much you enjoy life is due to your comfort level with risk. If you live a life with the impossible notion of having zero risk, you may be happy but you won’t know how much happier you could have been if you explored new experiences with some risk attached. Risk is the opposite of comfort. If you feel comfortable at all times, the risks you’re taking aren’t stretching you—and everybody has different comfort levels. I’m very comfortable looking out a window of a jet flying at 40,000 feet, but put me on a 10-foot ladder that shakes a bit and I’m freaking out. Another person might think I’m crazy for boarding that plane, but cleaning the gutters on their house is no big deal.

The key is that fear can drive decisions. Decisions affect what happens in life and those experiences shape people. In my life, I have more regret over the times I played it safe than the times I took risks. When I started my first company, I was just 19 years old. To some it looked like a risky decision, but there was very little risk involved because I was a college kid, living with my parents and had relatively low expenses. I didn’t have anything to lose with this venture since it was bringing in more money than my illustrious job wrapping burritos at Taco Bell.

Looking back, the business I created was the safe route. My company wrote custom software for local businesses. We would agree on an amount for a project, sign a contract, and they would pay me 50 percent up front and the remainder on delivery. Incredibly low risk. A higher risk option would have been to sell my software in computer stores—the way apps were sold before the internet. Selling packaged software was tempting because I wouldn’t just get paid once like contract work, I’d get paid over and over again for that time I spent building it. This might have been a lucrative business, but I was too afraid that my software wouldn’t be good enough and, in addition to the months of unpaid coding time, there’d only be a handful of sales. The prospect of making little or no money for my effort was terrifying.

In hindsight, I can see how foolish I was to let fear drive my decisions. That was the Wild West of the personal computer industry, before Microsoft was a household name, and would have been the perfect time to take that risk. Instead, I let this time slip by and two years later was married, buying furniture, paying rent, and collecting stuff. It would take 25 years for me to realize that more stuff wasn’t the key to a happy life. Taking risks and challenging myself to step out of my comfort zone was the answer. When I finally summoned the courage to risk building and selling apps on my own, it opened a whole new world for me personally and professionally. Many of the friends I have today—and my current job at Apple—are a direct result of taking this risk.

Speaking of Apple, I had another opportunity to dramatically change my future during the second-coming of Steve Jobs. I had just sold all my shares from my most recent startup and was deciding whether to invest in AAPL stock or buy a bigger house. Our old house wasn’t tiny and we could easily have stayed there, but the short-term comfort of a bigger space was very appealing. The new place was very comfortable, but if I had used that $20,000 down payment to invest in AAPL at around $10 before several splits… well, let’s just say that I would have had my choice of any house I wanted today. I don’t allow myself to do the math anymore because it’s too depressing to see the cost of choosing comfort over risk. Additionally, buying the bigger house meant buying more stuff, which made it even harder to risk moving or expanding our universe.

No one can guarantee that a risky decision will turn out better than a safe one, but there is a theme in my life. Every time I allowed my fear of the unknown or the uncomfortable to guide my decisions, I delayed advancing my life. In each instance, I can recall my gut telling me to take the riskier path and my head talking me out of it. Some of my most daring moves—the “trusting-my-gut” moves—have been in the last 15 years. I was almost 40 before I really started seeing how many opportunities I lost because I didn’t want to be uncomfortable or fall hard due to a big failure. This means I took a lot of risks in my life when I had a lot more to lose—when the decisions to give up comforts and security are dramatically more difficult.

I wasted so much of my youth playing it safe.

So here’s my simple advice to you: Take as many risks in life as you can while you have less to lose.

You are young and single with more of a job than a career—you can afford to experiment. Focus on finding a position that offers learning and experience over income and stability. Grab the job that lets you travel and explore other cities around the country and the world. Rent a furnished apartment instead of anchoring yourself to bulky, expensive couches, tables, and chairs that have to move with you. Expand your horizons before your vision is blurred by familiar surroundings. Check out cities with diverse cultures, magnificent museums, exceptional landscapes, and opportunities to broaden your views.

What you understand today as fun and enjoyable is limited by what you have experienced. Your comfort is a trap that keeps you from seeing and fully experiencing this beautiful world. Exploring it on the internet is nowhere near the same. Also, being comfortable is highly overrated. Some of my fondest memories were the times when we had no plans and just decided to go on an adventure and see what would happen.

It took a few trips to London and Paris and a move to San Francisco after five decades of life for your mother and I to understand how cool it is to shake up things and try new experiences. Our world is bigger and better now and we’ve barely scratched the surface of what is out there culturally. My hope is that you don’t wait as long as we did to step out of your comfort zone. I never knew that I’d like so much of what I like now and never would have if I didn’t push myself to take risks throughout my life. My wish for you is that you surpass my accomplishments, and the best way to do that is to start embracing change now while you’re young and free.

The place (or person) that you love might be out there right now, but you’ll never know it if you don’t go for it. Stretch yourself. Find a bigger, deeper happiness than you could ever imagine having today. Make yourself uncomfortable. Take risks.


Life is full of little gems; those moments that you want to bask in and never leave.

Today was a sunny Saturday morning and we had just finished breakfast. Judy and I were sharing a decadent, almond milk mocha—sharing one eases the calorie guilt—when she looked at me and said, “I don’t want to move.” I was confused for a second, but then it clicked that my lovely wife meant, “move from this moment.” And the moment was good.

Just like the core memories in the excellent Pixar movie, Inside Out, moments like this can be used to build a structure of support systems to define who we are. They are the platforms that we rely on to give us stability, strength, and joy in life. It’s all too easy to get lost in the darkness of the day with news services pimping despair and fear to the general public and political posturing dredging up the worst of humanity. Personally, I’m always in danger of being swallowed up by my own darkness, and I need to spend more time documenting these moments of light to keep my head on straight.

Earlier this month we had a lunch out with our kids when we were in Houston, and that was a lovely moment. Everyone was talking to each other and enjoying being together—something not always possible with siblings. The laughter and smiles punctuated that moment and made it stand out as one of the good ones. In fact, all my favorite moments are decorated with the faces of friends, coworkers, and family members. People make the moment.

I have a newfound respect for Chris Rock after watching him with Jerry Seinfeld on an episode of Comedians in Cars Getting Coffee. Something he said stuck with me. In response to Jerry’s question, “How do you like the car?” Chris said, “It’s all about the company. A gourmet meal with an asshole is a horrible experience. A hot dog with an interesting person is an amazing meal.” What a glorious perspective.

I’m the type of guy who picks his company very carefully. The people I work with are as important as the work I get to do. I don’t have time for fake friends and I don’t choose to share my precious moments with just anyone. When we were back in Buffalo last month, I made sure to set aside an evening for my best friend and his wife. He asked where we wanted to eat, and frankly, I didn’t care—just pick a place we can all hang out and talk. It’s about the company.

One advantage of living in San Francisco is that people come here to visit and I get to steal some time with them. My buddy, Mark, flies in from Australia and says we’re meeting up with friends at an SF karaoke bar. I’m there! It’s a great gang that I always have interesting conversations with, so why wouldn’t I make the time? Friends who live in the Bay Area are up for a night out. Why would I miss that moment? It’s so easy to ignore a moment that may end up being one I cherish; I want to capture every one that tries to slip past.

Even the sad moments are worth keeping. Our Houston trip had many great visits with friends and family, but we also had to make the hard decision to put down our 14-year old puppy (she had the joy and exuberance of a puppy at every age). It was the worst feeling to carry out that act, but the final moments with our loving dog were precious. The tears and sobbing reflected just how much love and happiness Magic brought into our lives. I’ll remember that moment because of the wave of emotions it created and because of how wonderfully supportive Judy was during that time. I was a wreck and she held me up. Moments filled with love.

I didn’t make any New Year’s resolutions because they seldom stick, but I’m making one now: I’m going to focus on the moments that matter. I’m going to enjoy those times in life that I get to spend with people that matter. Whatever is happening in the world around me that tries to sink my hope, I will still have these moments to keep me afloat. Thousands upon thousands of moments. Even getting the chance to write this and share it with others is a moment I’ll cherish.


Growing up a middle-class, white kid in the suburbs of Buffalo, New York with parents 40 years older than me and siblings nearly half that much, the majority of the music in our house flowed from the ’40s and ’50s. One of the first songs I remember hearing that woke me up was Revolution. I was too young to understand why that song impacted me so very much when it first came out, but it created a hunger in me for new music. As I stumbled into my teens, I bathed myself in the rivers of songs that flowed out of the ’60s and ’70s: Beatles, Yardbirds, Clapton, Zeppelin, Jimi, and so many others.

MTV was launched while I was in college and artists became more than static images in liner notes and on album covers. David Bowie was glorious in videos. My small suburban mind was blown to see his androgyny and theatrics. His sound and visuals were complex and slightly disturbing. I watched DJ and Space Oddity a hundred times (early MTV had a limited playlist) and studied every movement and note. I loved every video he ever made no matter how different it was from the previous one. Bowie defined change for me.

Reinvent. Resist convention. Don’t settle for normal, normal is boring. Shock, challenge, make them think.

I’m sad to see this great artist die, but I’m thrilled to have used his music as a soundtrack for so much of my life. If you see me with a headset on in the next few weeks, just assume that I’m listening to David Bowie.


There are moments in life that we ignore, that we rush past, that we take for granted. So many of these are sacred.

It’s easy to complain. There are plenty of reasons to bemoan the moments that don’t seem to go according to our plan. In that moment, our minds wander and drift to the future and stir up worry. The future is a ghost that distracts our attention. It’s a thief. Pay it no mind. Feed it none of your time. Instead, use those moments and embrace the now; give thanks for what we have—family, friends, a shared meal, laughter, love.

The now is what’s real. It’s what feeds us. Life is a study in the now. I truly believe those who accomplish great things are the most present in the moment. They see more of what is happening around them and don’t let the future affect their focus.

My view of the present is vivid. Being attention deficit, I’m rarely able to focus on a single current event. Sounds, visuals, and smells bombard me and stain my brain even when I work to block them. But I don’t see this as a curse because it allows me to drink in more of the world and, when managed properly, learn more quickly. The now is a busy place for me.

Even with this carnival stimulating my senses, my mind wanders from the now. Not really wandering, more like relating. A sight triggers a memory, which connects to another, which links to a third, and so on. I can travel decades into the past in milliseconds and then spin that moment forward into dozens of scenarios that might have been.

These trips are unwanted and unproductive. I didn’t book these flights of fancy and I’m not skilled at exiting the plane in time to avoid triggering dangerous emotions that too often spiral me out of control and cause disorientation and a loss of direction. Ironically, as often as I am annoyed with these wayward journeys, I also understand that they are part of what makes me who I am. It’s just a matter of training myself to see this time travel as a gift and to embrace it.

Even that which is a flaw should be treated as sacred. It’s meant to be part of my journey and I have the responsibility to make the most of it.

What we do with what we have in this moment with those who are in our circle of influence at that time creates the future. Nothing exists without some action. I can spend hours judging myself or others around me and nothing will change. My thoughts are useless without a next step. If I want change in myself, I need to enact different behaviors. If I want the world around me to change, I must create movement—dialog, discussion, or actions. Wishing it to be different is fruitless.

I won’t deny that I envy skills that others around me possess, but I work to not let that consume me or dilute my abilities. As with so much in life, it’s perspective that triggers what happens next.

I am not clairvoyant. I do not know how many “nows” I will have. The one before me is my only now, so how will I use it? Will I create or consume? Will I reach out or retract? Will I change the world or merely the channel?

This time is sacred. Precious. Fleeting. Scarce. It will only come once and then be gone forever. There will be a time when I sense my last moment and, in that moment, I don’t want to travel back and see millions of my sacred moments wasted or neglected. I want my last journey to be a celebration of life filled with movement and love and change. I have no expectations of a historic legacy for myself. All I desire is my time on this planet to cause a slight shift in the universe—to leave this world a better place than when I arrived. We all get that opportunity and I don’t want to waste mine.

Right here. Right now. This moment is sacred.


As much as I love the movie Schindler’s List, I have little desire to see it again. I’ve seen it twice and both times were exhausting. Maybe it’s the disturbing black and white visuals of this dark time in human history when so many millions of Jews were killed and millions more displaced. Maybe it’s that the acting and directing are both so good that I lose myself in this film that triggers so many deep emotions. Not that I need to see it again to remember it, I can replay most of it in my head any time I want and the ending will never leave me.

This scene is right as the war is ending and Oskar Schindler, a greedy German businessman who turns into a humanitarian after witnessing Nazi atrocities and ends up saving about 1100 Jews, is reflecting on his rescue efforts. I love this point in the movie because it shows that there is hope for all of us—that even a selfish individual can become a hero. Oskar’s final dialog is telling regarding his character change. He starts to realize that his factory scam to keep his group of Jews out of the concentration camps worked and reality was setting in.

“I could have got more out. I could have got more. I don’t know. If I’d just… I could have got more. I didn’t do enough!”

“This car. Goeth would have bought this car. Why did I keep the car? Ten people right there. Ten people. Ten more people. This pin. Two people. This is gold. Two more people. He would have given me two for it, at least one. One more person.”

Sometimes we can’t see what our efforts will accomplish or if they will even matter until there’s an outcome. If it turns out to be a failure, we bemoan our mistakes, but success creates its own problems. Oskar resisted expanding his efforts because he was afraid he’d get caught and he would suffer along with those he worked to free. Once he saw that his plan was a success, Oskar started to wonder why he didn’t do more. What should have been a celebration for him instead turned into regret—if only he had done more. He had a car and jewelry that could be turned into bribe money to save more people. He was consumed with his reality that he didn’t do enough. Generations of those he saved will disagree and have honored him.

Unlike Oskar, there will be no stones left on my grave; I have done nothing to save generations of lives, but the desire of Schindler to have done more strikes a chord with me. When he says, “I didn’t do enough!,” it echoes in my brain as I page through memories of my life. There are things that I could have done better. Times I could have done so much more.

I work hard to keep these pangs of guilt from becoming true regrets. My world view, which is tainted by many time travel sci-fi episodes of Doctor Who and Star Trek, is that everything happened as it should have. Changing even one tiny decision in the past would change what I have or who I am today. The smallest tweak of history wouldn’t happen without a cascade effect on my present and future. Time is fragile and not to be tampered with or viewed as an a la carte meal. Once dinner has been served, there’s no swapping out the courses.

For example, my father was very athletic in his younger years. He told many stories about his high school years as a track star, and as a young adult, his amateur boxing and prowess on the football field. By the time I was born, he was in his forties and limited his sports to softball and bowling with less and less time on the field as his knees and other body parts started to fail him. Even in his reduced state, I saw him as an amazing athlete. He knew so much about every sport and taught me how to break in a baseball glove, use my body to block a grounder, tips on boxing, and several courses on how to handle a football. Some of my favorite memories are having a catch with my dad. But outside of being on a bowling team, I avoided all organized sports.

That may sound insane with all the sports focus in my youth, but I was worried that I wouldn’t measure up to my dad—that he’d be ashamed of me if I couldn’t be a star. My older brother, Bobby, played soccer, a sport our dad never tried. He died before I was old enough to ask him, but I’d guess he chose that sport for a similar reason and didn’t want to compete with the stories any more than me.

One year my dad even coached a football team on a summer league, which would have been a safe place for me to start with my mentor in charge. It’s not that I didn’t think I had any skills—even as a 120-pound teen I could squirm away from tackles and carry a bigger dude on my back for several yards. But fear of not being good enough for him kept me on the sidelines. I always wished I could change that decision. It would have given me more time with my dad and more confidence during my challenging teenage times.

Instead of athletics, I went for top grades in school. Most courses came easy to me and weren’t something I could opt out of like sports, so I tried to be a star student. This path didn’t do much for my social life. Picture a skinny, pale boy whose good grades made him a favorite of many teachers and you probably don’t see a lot of girls hanging around that kid. You’d more likely visualize me hanging with the smart kids, but I was smarter than I was hard working causing my grades to be just shy of exceptional and keeping me out of the top ten percent of my class. This meant that I didn’t fit with the honor student clique—who probably played Star Trek Tri-Dimensional Chess and spoke Latin to each other. I didn’t drink, smoke, or do drugs, so I was shunned by the cool kids and the “heads” (what stoners were called back then). As I already mentioned, not participating in sports disqualified me from the jocks clique. That meant I was pretty much on my own. I had a handful of friends each year and that was enough for me to survive my social isolation.

I met Judy when my best friend—oddly enough, a jock from my dad’s football team—introduced us. By that time, I had also grown an afro—yes, being pale and skinny wasn’t enough for me, I had to find new ways to repel girls. Luckily my future wife didn’t reject me on sight and we went on to build a relationship that has lasted more than 36 years.

But what if I had joined a football team? What if I wasn’t too afraid to take a chance and did become a jock? What if this one change kept me from meeting the love of my life?

Or maybe I would have met Judy, but I might have been a jerk sporting a testosterone-infused ego—my insecurities triggered enough stupid relationship gaffes as it was. Before meeting this woman, I had built enormous emotional walls around myself. It took her years to get me to talk honestly about my emotions and that’s just one little part of me that she fixed. Without her, I’d be a completely different man—a much lesser human being. And our kids, I can’t imagine my life without our three, now adult, children.

Thinking about my kids, I’d love to go back and be a better dad for them. I think about the time we spent together and I wonder if there was enough quality time. What if I had been more patient and spent more time teaching them sports, or programming, or anything that I didn’t do enough of? Would they have had an easier time in school or more job opportunities now? Looking back, I see so many missed moments when they were growing up.

Which brings me back to the whole struggle of being enough in this world. The past is gone and there’s no TARDIS or crack in time that I can use to go back and make adjustments. Even if I could, it’s way too dangerous to touch anything in my timeline and risk losing anyone that I love. All the past pain and loss and mistakes are stones that make up the foundation of today. Remove one small pebble and everything could crumble. What would I trade today to remove a regret of my past? Nothing.

If I wasn’t enough of who I needed to be at any point in my history, the only way to fix that is to be even an even better me in the present; to dive so deep into life that my chest aches from the swirl of everything going on around me and I have to burst from the depths every so often, take a huge breath, and go again.

Playing it safe isn’t an option if I want to be able to look back on this time and know that I did enough. Judy and I have been given so many opportunities with our new careers, our new city, and our new lifestyle—we can’t afford to squander this time. For me, doing enough means not letting fear drive decisions. I can’t be afraid to take on new challenges at work or try new experiences in my personal life. Keep growing and continue evolving is the plan.

Being enough for my family means finding a balance between work and home and a balance between interaction and intervention. I want my kids to evolve and grow, but I need to let them find their own paths. I also need to be real to them—flawed enough so they know they can overcome mistakes like I have. In some ways, my father was too perfect in my eyes. He was smart, athletic, popular, and could command respect from a child or adult with a stern look and a crooked, arthritic index finger raised into the air. He didn’t share his mistakes and failures with me until the last few years of his life, which was a shame. Maybe I could have been different if I saw him differently.

But then again, I wouldn’t be who I am today if he was different—and I really love my life. What I got from my dad seems like it was enough.


Back in 1999 I was putting together a team and raising money for my latest venture—an Internet startup running a website to host construction project information. It was a crazy time and a very emotional ride because it coincided with a growing fissure between me and my business partners. We had disagreements over the management of our existing software company and thought spinning off this new venture would give us some space to work apart. This transition forced me into taking on new roles and there was money and my reputation riding on its success.

To make sure that I didn’t veer too far off course I hired Paul Lemberg, a business coach who I had worked with in the past and trusted. He required that I check in often via email and we always had a Tuesday call to sum up the past week and plan the next one. I hated these calls. Not that Paul was hard to talk to—he was great—but it was his job to fix what I was doing wrong, so the calls ended with me feeling like I needed to work harder and push myself more.

After weeks of doing presentations for potential investors and negotiating terms, I was pretty happy with my progress and actually looked forward to my upcoming Tuesday call with Paul. I bragged a bit about my week and how things were going and he asked, “How are you doing with the investor calls?” Feeling somewhat smug I replied, “I’m getting quite comfortable talking to investors.” Expecting a compliment, I was floored when he said, “Then you’re not pushing yourself enough.” Dammit. Why couldn’t he just have let me enjoy my happy place? As I recall, my response was a well-crafted and eloquent 30 seconds of dead silence. I proceeded to pick up the remaining pieces of my pride and worked to take his comment to heart.

I totally get it. I was getting too comfortable and work is not about comfort. It’s supposed to push you and make you better. That’s not to say that you can’t have fun while working, but if it’s effortless, then you probably need to take on a new, more challenging task and delegate the easy stuff. In the case of my investor calls, I was talking to the people I knew, the low-hanging fruit. These were good calls to make, but I needed to go further. I needed to get through these calls quickly and go after the bigger fish—the calls I wasn’t comfortable making. I was accomplishing just enough to make myself feel good about what I was doing, but not the work that would really make a breakthrough difference.

When I was first married, I had a job that paid the bills. Well, Judy usually made more money and paid more of the bills, but at least I helped. During that time I was constantly working evenings writing software. Sometimes it was shareware for the Mac and other times it was contract work to bring in extra money. These extracurricular activities inspired me in ways that my day job couldn’t. I felt limited during the day and free at night. I knew my day efforts wouldn’t blossom into anything more than a small annual raise. If I wanted to do amazing things, I was going to have to color outside the lines and push myself to be more creative with my time.

Because my wife was more responsible and had the stable career, I had the flexibility to spin many of my nighttime efforts into full-time ventures, which is why I’ve had five different startups over the years. It wasn’t always easy to write code until 2 AM and be ready for a Houston commute six hours later, but I wanted to be more than I was and do more for our future. I could see that my 9-to-5 job wasn’t my destiny. It didn’t fulfill me or stimulate significant personal growth. It wasn’t that I was bored, but it was more like feeling out of place—I could and should do more with my talents.

“I’m a lumberjack and I’m OK. I sleep all night and work all day.”

Both my sons are in their mid twenties and working long hours at fast food restaurants. When asked how things were going, my elder son quoted the above Monty Python lyrics. It made me chuckle, but it also concerned me because I know it’s all too true. I’m proud of them for their work ethic, but I want more for my kids. I want them to be more than what their work defines them as today. They have a poor work/life balance because a lower-end job is just not going to give them enough income to allow for more free time. This kind of job forces you to put in long hours to pay rent, utilities, and food expenses.

Not that it’s all about the money. If you can lower your overhead, you could earn less and do what makes you happy, like volunteer work, outreach, or teaching. It’s less about how much you earn and more about the satisfaction of working hard and producing something of worth. We all have stepping stone jobs—Taco Bell paid for some meals and books during my first year of college—but too often we settle for a shallow career. So many of us never reach our potential.

I’m blessed to be a fidgety type who isn’t risk averse. Merely collecting a paycheck doesn’t cut it for me; I need more. Running my own indie software company was hard work, but I had done it for long enough that it was comfortable. I was my own boss, which meant no one criticized my code and I drove the schedules. There was risk, but the majority of my mistakes were made in private. Taking a position at a company filled with brilliant individuals was pure disruption to my cozy life. It was easy being the smartest guy in the room when I was the only person in it.

Fortunately, this risk paid off and rewarded me with new career challenges and a brand new urban lifestyle. I didn’t know what would happen when I made this change, but I knew I was being handed a huge opportunity if I was ready to work hard for it. Pushing past the fear of looking like a fool was probably the hardest task.

I believe the trick to growth is to learn to enjoy being out of your comfort zone; teach yourself to crave a challenge and abhor too much time spent with the familiar. Amazing things happen when you open yourself up to change and the discomfort that may come with it. Life is waiting for you to wade into it. Come on in, the deep end is fine.