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.

Moments

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.

Bowie

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.

Coping

One of Judy’s closest friends in San Francisco just lost his mother to ALS and is now in the process of coping with his enormous loss. How we cope with death greatly depends on how we handled our relationship with our loved ones during their lives.

I had a great relationship with my father throughout my youth. He worked long, hard hours as a truck driver and all too often he was getting home at my bedtime. This meant that anytime he asked, “Did you want to go with me?” My immediate answer was yes. I didn’t care if it meant I had to fix plumbing at my aunt’s house; I just wanted to spend time with him and he wanted me around. He was proud of me and I worshiped him. During my teen years and throughout college, our late-night conversations grew and I became very vocal about my plans for the future and how I wasn’t going to just punch a time clock.

Things were moving fast: I had just finished college, started my first software company, and moved into a side-by-side duplex rental with my beautiful new wife. I was looking forward to sharing my accomplishments with him as an adult—the universe had other plans. My father only lived to see three months of my new life. This was not the plan, not my plan at least. I was pissed off at his doctors, God, and the universe. Anger was my coping mechanism and there was plenty of scorn to go around.

God was an easy target since my faith was already on shaky ground when dad died. This is how you show me you exist? This is proof of your mercy? This after you took my brother so many years ago when I was just five? I didn’t wait for answers and just slammed that door shut… tight.

As for the doctors, I quickly learned the limits of medical science. Before he died, they released my dad so he could go home and recover from heart surgery and a stroke, but his health was deteriorating and he couldn’t keep food down. He could barely walk on his own and was withering quickly. When I asked his doctors why this was happening to a 60-year old man, their answer was, “We’re not sure.” You’re his damn doctors. If you don’t know, who does? You had him in this hospital for weeks, you cut him open to fix his heart and ran test after test on my dad. How could you not know?!

This was all bullshit and not how this part of my life was supposed to go. My father was supposed to be there for me and advise me on my new career, marriage, and life in general. But here I was instead trying to find a way to keep him alive. In some ways, I was very mature for my age, but in so many others I was just a kid.

I saved the bulk of my anger for myself. The doctors’ only advice was to admit my father to the hospital again so they could try to get some nutrition into him and run even more tests. I remember having to carry him into the car that afternoon to get him to the hospital. He felt so fragile in my arms. I wasn’t that big or strong; I shouldn’t be able to lift my father so easily. I don’t recall straining to put him in the vehicle.

After driving to the hospital and delivering him to his room, I told him that I was very disappointed in him for giving up like this. I said that he used to be a fighter and this was so unlike him. The look on his face as he replied, “I’m trying, Kev,” broke my heart, but I thought he needed tough love to push through this setback.

Later that night Judy answered the phone, turned to me with tears in her eyes, and broke the news that my father was dead. My first feeling was regret about my harsh words to him in our final conversation. I remember telling Judy how horrible it was that he died thinking I was mad at him or that he was weak. That’s not how I really felt. She comforted me and said that there’s no way he thought that. Unfortunately, it would take years for me to let go of that regret.

I barely remember crying and the rest of the night is completely a lost memory. Portions of the funeral stick in my head, including returning from the church and not being able to step foot in my childhood home where Fran Hoctor’s Irish wake was being held and dozens of family and friends were inside toasting his life. I told Judy that I needed space, got in my car and left. I don’t remember how far or where I went, but I wasn’t coping with this well and just needed to be alone. I didn’t want to hear stories of his life—I heard those many times before and there was no solace in them now. My mentor was gone and his stories were at an end.

How could I have expected to cope with his death when I wasn’t even coping with his dying? The whole time he was in the hospital, I was upset that my new life was being put on hold. Hurry up and heal, dad, so you can see all the stories that I’m creating in my own life. How is he still not fully recovered? The petulant child in me was inconvenienced and was never prepared for the possibility that he wouldn’t make it.

No one knew how angry I was for the next few years—I kept all that deep inside for fear of what I might do or say. On the outside, I lived life as if nothing had happened, even though I still wrestled with pain and bitterness on the inside. I left Buffalo as soon as I could convince Judy to move to Texas. I had to get away from the place that reminded me of who I had lost. I wasn’t going to get sucked into the void—I had plans. Even though he was dead, I was going to show him that I could accomplish everything that he wanted for me and more. It took several years before I’d even share how I felt with Judy. Maybe I wasn’t even honest with myself. I don’t really know.

I’ve become very pragmatic about death—it’s a part of every life and we all have to deal with it at some point. I often wonder if I’m too practical—too logical about it. Has part of me shut down as a defense mechanism to the pain of loss? I’m not an emotional stone by any stretch of the imagination. I can’t watch the ending of Field of Dreams without my vision going all blurry. Shoot, there are movies that Judy makes it through with dry eyes and I’m the one reaching for tissues. Maybe I’m just broken in this one small area.

My wife was just 30 when she lost her mom to cancer and it devastated her. Judy would talk to her mom on the phone almost daily. Now that routine was gone and she couldn’t share her day or ask her mom advice on how to raise our three young children. I tried to help her cope, but there is no way I could fill that specific hole in her life. More recently, Judy’s dad died after living with us for several years. Wally had kidney and circulation problems that sent him to the hospital way too often. More than once, we had to be prepared that he might not recover, but that didn’t make his passing any easier on Judy or her brothers. My initial reaction was a feeling of peace. His pain was now gone and Wally could finally rest.

When I did break down in tears, they were from my emotional exhaustion. Seeing this man fight for his life reminded me of my own dad’s battle. Working from home, I had a front row seat to Wally’s health problems. It only made sense for me to step in and help him when he needed it—and I was happy to do it. In many ways my service to Judy’s dad was to make up for my inability to help my dad when he needed me. That connection didn’t sink in until my caretaker role ended. There were moments of selfish thoughts as well as I thought about how many times Judy’s dad recovered from life-threatening health problems. I wondered why my dad didn’t get a few more chances. A few more years.

Each time there is a death, I feel a nudge to take inventory of what is still present in my life. It’s a wake up call about my choices, health habits, and the people who are important to me. I’m not sure that I handle loss in a normal way anymore—if there even is a “normal” reaction. I’m an emotional person, but around death I become strangely disconnected. Except for the time my dad died, deep sorrow and tears aren’t my first response to death anymore. My first thought is how this death affects the loved ones who are dealing with loss, but it seems like I stay one step back from real emotion. Even now as I write about my feelings, I struggle to understand how I actually cope with death. I’m overflowing with empathy for everyone involved, but I’ve built some sort of insulating layer around my heart and mind.

My logical mind accepts death as inevitable. Is that really how I feel or am I kidding myself? If death took Judy or one of my children, I don’t know if I would have the capacity to cope—my protective wall might crumble and take me with it or expand to the point that I can’t feel anything. It doesn’t matter because I don’t want to ever find out this answer. Even writing about it makes me a bit sick inside. Revisions to this article have felt like I’m standing at the doorway of an ominous, dark room, glancing in but terrified to enter.

For now, I’m just trying to be present and grateful for those around me and not let anything broken within me get in the way. Writing has helped me unlock my past, confront buried feelings, and appreciate what I have been given, which is a very good thing.

This is me coping with life.

 

Enough

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.

Gone

I awoke the other morning in a bit of a funk. My head was cloudy and I was on day three of a dull, persistent headache. My weekday morning routine is to quickly clear my inbox of the 50-100 new messages that collect each night, which also serves to wipe my mental slate clean and prepare me for the day. This morning that didn’t work so well and I thought that writing might help clear my brain of whatever it had accumulated during my sleep. I looked at the article that I started the night before and reread the lonely two paragraphs. Ideas began to flow and I poured them out onto my keyboard and into the web editor.

As it often does when I’m in a stream of consciousness writing mode, words become my complete focus, which sends pain and problems to the shadows. This is a really cool place for me. When I’m writing, I feel lighter. My physical self fades and related problems go with it. The world around me dissolves to become a backdrop of muffled sounds and colors—my only reality is my prose. Some people call it being in a zone, but it’s more for me. In this altered reality state, I hear myself speaking in my head and the physical me has one job: Document this talk and don’t miss a word. You never know when the speaker is going to leave or forget what he was saying and just stand there drooling (obligatory old guy joke).

As I documented this latest talk, I noticed that the newly typed content was diverging from the original concept, but I never let this stop me—I always can make two or three articles from this one when I’m done with this writing session. Getting the words down is the important part. Don’t let the creative process stop. Don’t interrupt the speaker. Today’s talk is full of great stuff, or complete crap that I may delete later, but right now it sounds good so just get it written.

Pause. Save draft. Continue writing. Pause. Save draft. Continue writing. It’s an old habit of mine to save every time I pause to think. I’ve always practiced safe writing. It’s a good habit, one that has served me well over the… wait, why is it prompting me to confirm I want to save the draft? Of course I want to save the draft. SAVE ALL THE DRAFTS!

What? The two paragraphs on the screen are what I wrote last night and my newest six or seven are nowhere in sight. No worries; I’ll just go back a page in the browser and copy the text from history. No history. No extra text. Just those two stupid paragraphs from last night. After a few frantic minutes of useless recovery techniques, I had to admit that I screwed up. There was no way out of this one. My bag of technical tricks was empty and my words were gone. Just. Gone.

To a writer, there are few things more heartbreaking than losing words. This loss was the equivalent of a Chuck Norris punch to the gut. I was so devastated, that I closed my MacBook Pro and shoved it in my bag. Then like any good writer who has a big setback, I sulked and texted my wife so I could bemoan my great loss. This inspired writing session was gone and my dull headache and funk slipped out of the shadows to take over my brain. Screw writing. Pop in my headphones, turn on some music, and switch to reading. And sulk. Sulk like a professional.

Now I don’t blame anyone but myself. I rarely only use an online editor and also prefer to have a local backup. I use several apps for writing, but this morning I just wanted to get the words into my drafts folder in case I wanted to continue writing later on a different device. I know better than to play fast and loose with critical data and have been trained to be paranoid about data loss from the first time I typed text into a computer.

Back in the early ’80s, my first experience with electronic storage was on a Pr1me 450 mini-computer. Erie Community College wasn’t the richest school and the terminals available to students were proof. You may not even know what a “terminal” is. Today, we have computers in our pockets and on our wrists that make that college minicomputer look like a calculator. But back then we all had to share a single computer by using several very dumb boxes each with a video screen and keyboard combination to talk to this one smarter box via serial cables or modems.

And forget about the high resolution, crisp, colorful screens of your laptop or iPhone and instead think about a really blurry TV screen with gray glowing text on a darker gray background—you may have seen one of these in a movie or a YouTube video. Now add controls on the back to fix vertical flipping and horizontal skew problems and wrap it all in a chunky, molded case (no idea what material) with a built-in keyboard. They were pretty crap. Flip the switch to turn them on, wait for the screen to warm up. Adjust the brightness and contrast so the text was somewhat legible. Smack the side if the nobs in the back didn’t stop the screen from being jittery and say a prayer that you didn’t have a broken one because terminals were few and students were many.

If you were writing software on these little beasts, you had to understand that even if it turned on, it could as easily die at any moment. You learned to save often or got used to disappointment. Some students didn’t notice that these terminals were gravity cooled with vents on the top and learned by a zap of the screen that blocking the those vents with books and folders led to a terminal terminal. Along with the death of the circuits also went any unsaved typing. When I saw people using the vents as a shelf, I tried to be a good Samaritan and warn them to let the thing breathe. The early days of computing weren’t pretty, people.

When I had time outside of my classes, I spent it writing software on a TRS-80 Model I computer—owned by a friend of my dad’s who I was helping—and learned that microcomputers were as finicky as their bigger brethren. The cassette tapes often failed and the newfangled 5-1/4″ floppies weren’t much better. Always fearing the worst behavior from this magnetic media, I liked to print out my code listing and keep a paper copy as well as making multiple backups of disks. One time I had worked for weeks on a large customer database program written in TRS-80 BASIC and had made two backups in addition to the original disk. I came into the office one night, shoved the primary disk in and it was blank. My code was gone. I grabbed the first backup disk and tried to load it… blank. Panicked and scrambled for the second backup and it too was useless. Weeks of work were just gone.

My hard copy wasn’t recent because I felt there was no need to waste paper since I had multiple disk copies. I thought I was sufficiently paranoid, but that day I learned that I was way too trusting of 1981 technology.

This story does have a happy ending, though. When I first wrote the database program, I was a new computer science student and did a piss-poor job of it. Having to rewrite the whole thing after a few month of programming forced me to rethink it and redesign it completely. I also learned about the concept of offsite backups.

My lost article also might be better when I go back to write it again, but I haven’t felt ready to clean that wound yet. While whining to Judy about this minor disaster, she said, “If you can’t think about the words you lost, why not write about losing it.” Smart lady.

So I did (and you just read it). Maybe I’m a little more ready to go back and finish my other article. Or maybe I’m still sulking.

Writing

I was watching Almost Famous for not the first time and I saw the movie from a completely different perspective—the perspective of a writer. Normally I’m watching William, the main character, deal with the rock and roll lifestyle and his love interest while touring with the band—the fact that he has a writing assignment is just how he gets into this situation. This time, the process of his article being published as a cover story in Rolling Stone magazine struck me. I was so happy for his success that it made me think about why I write.

When I was in seventh grade, I had a homework assignment to write a poem. As with most homework, I put the assignment off. And then put it off some more. And then just a bit more until it was late on the night before the due date and I just wasn’t in the mood to write, so I set my alarm for 5 AM and decided to churn it out before I walked to school.

During Buffalo winters, it’s pretty damn dark and cold at that time of the morning. When the buzzing of my clock radio startled me from my sleep, I was mostly inspired to dive deeper under the covers and stay warm. Poetry wasn’t oozing from my hibernating brain, but I was a good student and didn’t want to get a zero on this assignment. It was this stick that motivated me to get up, flick on the lamp sitting atop my desk, which had been painted a dull green by my mother in an effort to make the natural wood look better (man, we had style problems in the ’70s), and write the poem. It was a short piece entitled “We Power the Ride” and was inspired by my experience of rowing a small wooden boat out on the glass-smooth waters of a Canadian lake while listening to a loon dive under water and reappear on the surface many yards away. Since I had this experience every summer on our family vacations, I thought it would be easy to form into a poem. The words flowed quickly and easily, causing me to assume it was lame. Crap work or not, I decided to hand it in. Even dribble like this had to score higher than a blank sheet of paper.

The next day, I saw my poem hanging on the wall in the classroom decorated with an A and the words, “Great work!” My teacher even took the time to pull me aside and tell me how much she loved my poem and that it was real and descriptive and powerful. This thing I wrote at the very last minute that struck me as barely worth submitting had touched her. Amazing. She encouraged me to keep writing and said I had a talent for it.

Over the years, I’ve toyed with the idea of a career as a writer. I took time off between ventures to write, but never spent enough time at the task because I had to earn money to feed my family. After an unpleasant separation from my business partners, I struggled for the next year with a lack of self-confidence and direction about where I was heading professionally. I decided it would be cathartic to write a book about the experience and worked on it for several months. Over the next year I edited, revised, and rewrote chapter after chapter. Some were so painful to write that it took weeks to get up the courage to go back and edit them. My goal was to be as authentic as possible with my writing, to bare my soul.

Soul baring was harder than I expected. There were moments when I broke down in tears while typing my story. I’d get done with a few paragraphs and have to give myself time to recover. At one point I asked Judy why I was doing this to myself. No one was going to publish this, so why bother with all this pain? As my wife always does, she encouraged me to keep writing; to create something good out of a bad experience.

After about a year and a half of work, I sent my latest draft to a trusted friend to read. He was very honest—as I knew he would be—and said that I didn’t dig into enough detail. The story was good and covered all the facts, but he wanted to know what was going on below the surface, including the sights, sounds, smells—everything. My concern was that this book was already too long and I was shoving too much of my personal life down someone’s throat. Why would they want to invest more time to read a longer narrative? It made perfect sense after he explained how much more present and invested people would be in my story with more vivid descriptions, but I just couldn’t go through it again. I couldn’t live that time of my life one more time and with more detail, so I set the dozens of drafts aside in an archive folder on my computer and put the project to rest.

That investment of time and emotion wasn’t wasted. I truly learned so much from the experience. I learned that I loved to write even if I never made a dime from it. I learned that writing was a creative and iterative process. I learned to throw away paragraphs or pages that didn’t fit the timing or flow—even if I loved the words. And I learned that sharing what I lived might actually be worth someone’s time to read. Life is about making connections and so many authors have connected with me through their works over the years.

When I started my previous blog, Entrepreneurial Seduction, I wanted to help others who were starting a business avoid the mistakes I was making. This was not meant to be a polished narrative of my experiences, but a raw telling of what was happening in the moment. It was a way to give back to all those who were helping me make another go at running my own software company by giving everyone a blow-by-blow of what I was doing—right or wrong. Frankly, I chickened out at one point to avoid casting any shadows on my company that might cause customers to have concern about the potholes I was hitting. Articles started to get left in the drafts folder and after several of those withered there, I delayed writing new posts. The lag between articles became longer and longer until it was barely worth anyone’s time to check into my site for content.

Another problem was that my blog was so specific, I never felt like I could write about random occurrences—the many personal thoughts and experiences I was enduring. It was too constraining. I thought about starting a second personal blog, but then I felt the pang of guilt. If I’m behind on articles for my business blog, how could I cheat on it with my personal one? I trapped myself and killed any desire to write. Guilt is a horrible thing. It twists you up in knots and gnaws away at you.

The massive shift in my world last year was the break I needed to reboot my writing. So here I am publishing on a much more consistent basis and I love it. Writing satisfies a passion deep within me. Hearing that what I write touches someone takes me back to seventh grade and the awe I felt when my teacher was moved by my poem.

Writing is creation. It is love. Pain. Hurt. Happiness. Success. Failure. Writing is a release. Thank you for allowing me to write for you and for the time you spend reading my work. I hope you have a way to experience this kind of joy. For me, writing is how I allow my soul to smile.

Letting Go

Stating that I’m letting go of something or someone implies that I once had control, but most of the time, having control is a lie.

Moving to San Francisco meant that Judy and I had to let go of many things: home ownership, cars, friends, and family—especially our kids. The latter was the hardest. Our youngest was 21 when we moved and lives in an apartment while she attends Texas State University, so it’s not like we saw her every day. Our two boys were 23 and 25 by the time we settled in our West Coast apartment, which meant that they had jobs and were busy as well, but they lived with us and we talked often.

Having a 2000-mile gap means that we have to work harder to communicate and spend time together. They’ve all visited our new home at least once and Meaghan just left after an extended weekend stay, but gathering now takes more planning and money. This also means that we’ve given up even more control over their lives. We can’t just drive over to their apartments for a visit and we can’t intervene if there is a problem. This letting go is hard. These are our children and the natural urge is to guard and protect them. Now we have to trust that they will keep us in the loop and tell us when they need help.

As fathers go, I’ve always been more hands off. I trusted that my kids would recover from their mistakes and thus I let them flounder a bit as they grew up. That may be because I was given a wide berth as a child and entrusted with responsibilities and I wanted to give my children that same gift. When they didn’t do what I would have done, I was always a bit lost and didn’t always react appropriately.

“Really? You want to sleep in this messy room and have no problem entering that disaster of a bathroom?”

As they shrugged with indifference, my skin crawled. Compared to our kids, I was Mr. Clean as a teen.

“So you don’t want your own apartment? You’re okay still living here with your parents in your twenties?”

I wanted nothing more that to escape my parents’ world as soon as I could. Apparently, we made life too comfortable for them. Maybe if I was angry more often or didn’t enjoy the same flavor of Pop Tarts as my sons or didn’t watch the same movies. Who knows.

The struggle was and is that we enjoy spending time with our offspring—flaws and all—while at the same time wanting them to be independent adults. I know that I was seen as the heartless one pushing them out of the nest while their mother was more focused on them getting an education and careers. Judy was pushing them to grow and not to go.

But part of me was looking forward to seeing them take flight. I wanted to see what they could do on their own and how they would deal with the real world. I was also looking for some more time with my wife. After 25 years of raising kids with the last 6 also taking care of Judy’s dad, it felt like we needed time again as a couple.

Having a 4,000 square foot home made it hard to say that we didn’t have room for our kids to live with us and downsizing was going to require an investment of time and money to unload our house, so my efforts to empty the nest were pretty lame. Then the opportunity to move to California happened and accelerated everything.

Our house had to be fixed up. Our stuff had to be reduced. Two of our children had to find places to live. And all this had to happen in less than three months.

One way to get your kids to move out is to sell the house out from under them: “You either have to get an apartment or cozy up to the new owners. Your choice.”

The chaos of starting a new job and prepping a house for sale distracts you from the reality that you are going to have to let go of your life and the people around you. We were having to let our children go. I couldn’t just help them with a car repair or fix a problem in their bathroom or hang out and chat about life events—they were on their own now.

I think it really hit me when we drove to Napa with Meaghan. Our adult daughter was visiting us from Texas to hang out over glasses of wine. She talked about moving to a different apartment and I realized this is the first time we wouldn’t be there to move her.

We talked to our boys about scheduling a visit of their own, but they said they’d have to work out when they could both get vacation time. They have their own lives and schedules now. Little by little, they have become more independent.

In some ways, I worry more about them now than I did when they were little. Will they continue to expand their world? Are they doing enough outside of work? Do they know that they have the universe at their fingertips?

It’s easy to get stuck in a rut. It’s easy to think that you have to do what you are doing to live. It’s easy to lose sight of the possibilities and wonder and opportunities all around you. It’s hard to let go.

But letting go is the only way to fly. Life is about exploration of the world within each of us as well as around us. We can do so much if we let go of hate, prejudice, bad habits, or our perceived limitations. Being tethered to a life without dreams of a better future is a terrible prison.

My wish is that by stepping out in faith and letting go of so much in our lives, our kids will see that they can do more than what they are doing now. Judy and I see so much potential in our children and we want them to soar.

What could happen if everyone in the world just let go a little? That thought gives me a chill of excitement.

Embraced

This was my first WWDC as a resident of San Francisco. I used to say I was traveling to hang out with 5,000 of my closest developer friends and it was really true. Not that I knew everyone who was attending this annual Apple gathering, but there was a kindred spirit among us and I made new friends every single year—some who have changed my life forever.

Now I don’t have to travel for the conference, except for walking a mile or two to the event du jour. As a local, I have embraced my role as one of the city’s unofficial ambassadors by helping visitors get the most out of their time here.

Besides the question, “How is Apple treating you?” (my answer is, “Great!”), the most common comment was, “You seem to have embraced the San Francisco lifestyle.”

Embrace is a glorious word. More than just a hug, it suggests love and enthusiasm and holding on for dear life—never wanting to let go. It’s a high compliment when someone says that I’ve embraced my new life. I want to be that guy who goes all in.

I mean, why not? Why bother moving from the Gulf Coast to the West Coast if you’re not going to squeeze every ounce of enjoyment out of it?

I grew up in a middle-class, suburban lifestyle not wanting for anything. We weren’t rich, but my dad was a Teamster and made good money driving a truck. He sacrificed adventure for stability. He took very good care of his family. But his great joy was when he sailed the Atlantic as a Merchant Marine in the Second World War. He hated the war, but he loved the sea. I would watch his eyes light up when he told me of his adventures on his ship. If there weren’t a family waiting for him back in Buffalo, New York, I’m sure he would have never left life on the sea.

But he was unselfish and loved his family. He did what had to be done to provide for us. I was born 14 years after my 3 siblings and saw a different man than them. This man had to bury his 19-year old son and spent his last decade fighting management problems at work. My father’s stories of adventure contrasted so dramatically with his day-to-day life and I could see that he had lost too much. He embraced us and his friends, but I saw something missing. I saw him tired.

Growing up, I vowed to be daring and not settle for just a paycheck. I wasn’t going to punch a time clock, no matter how often my dad said it was part of life. He pushed me to go to college so I could do what he never did, but he also wanted me to understand how you have to compromise to survive—I despised the concept of compromise. As much as my dad longed for the high seas, I longed to be a rock star.

Musicians infused my life with such joy that I wanted to be one of them. Unfortunately, I was also practical and knew I would have to work incredibly hard to overcome my lack of natural talent. When I went to college and found a talent for programming, my desires changed. I could now create something from just my thoughts and logic. I embraced my new skills and started to write software for businesses, which lead to IntelliPACS, my first company. I thought Intelligent Programming and Consulting Services smashed together would be a great name, but I was young and naïve so forgive me for that one. Anyway, I was doing something I loved, getting paid for it, and working on my own schedule—which was after college classes and homework. There was a freedom to this work and no time clock in sight to punch. I sure showed my dad.

My skills at running a company were poor in my early 20’s and I ended up working too much for too little money. Life was changing rapidly with the start of a new marriage and the passing of my dad all within a few short months. I was tired of the long, dreary winters and wanted a change. Living in the small town of Cheektowaga also reminded me too much of my dad and how much he suffered and I wanted out. Both my sisters lived in Houston and I saw that as the complete opposite of my current life. Warm weather, new opportunities, and a big city that was filled with the technology that was part of my career future.

Texas was where my family grew up. My three kids were born and raised in The Woodlands, where Judy and I worked hard to create a stable place for our children. We traveled when we could to expand our world, but the suburbs of North Houston had become our home going on 30 years. The goal wasn’t to move, but to downsize and use our home as a launching point for more adventures. After visiting London and Paris, we both longed for more time in cities where we could stroll around and be immersed in architecture and culture. Maybe we could downsize enough to afford to live in London part of the year.

We had just begun the process of figuring out how to sell our house and move to a smaller place when my new job opportunity appeared. Now our eyes focused on San Francisco as an American substitute for living in London—less culture and history, but better weather and no citizenship issues. This was to become our new home. I wanted to embrace it. To swim in it. To change everything and live this new life to the fullest. Why move all this way if not to capitalize on the opportunity to go all in?

I remember my third grade teacher, Mrs. Rice, telling me that I wasn’t living up to my potential (homework was boring, so I may have skipped doing some of it) and asking, “Do you want to live your life as an underachiever?” Just to spite her, I said, “Yes”, which instigated a phone call to my mother and much discussion on that topic at home. But the incident stuck with me and I often ask myself if I’m living up to my potential.

Stay in the role where I’m the smartest (and only) guy in the room or challenge myself to grow even though it will be uncomfortable? I took the challenge.

Keep the cars and the suburban lifestyle that I knew or ditch the cars, live in a tiny apartment, and explore the unknown recesses of a new city? I chose to explore.

Not taking full advantage of every opportunity means lost potential and I can’t have that—Mrs. Rice will kick my butt. So when the universe presents me with a chance to change everything, I stretch out my arms as wide as I can and embrace it.

Connections

Last night at the Smile/AgileBits party, Jean McDonald took time to pull me aside and introduce me to a few people. She didn’t have to make this effort, but she is just that generous and I ended up having a great time talking to them. This got me thinking about how important making connections can be and how some can be life changing.

When I was in high school, my dad coached in a football league for teens. One day, I was talking with a guy on his team that shared classes with me at Maryvale and we hit it off. He respected my father and I immediately was more worthy of his investment of time to build a friendship because of our common connection to Coach Fran.

Club 747 was a discotheque decorated to resemble an airplane with seats and runway lights bordering the metal dance floor. On Sunday nights, they hosted teen dances and sold us sodas instead of liquor. Every week, Brian and I got dressed in our best polyester shirts and tried to look like John Travolta on the dance floor to make some connections with the ladies, but I was a skinny white kid with an Afro—yes, a natural Afro that required a pick for maintenance—and was less than successful.

Most nights after closing time, it would end up just the two of us talking over burgers or donuts while waiting for one of our dads to give us a ride home. We found so many ways that we were connected thanks to these late-night chat sessions.

When they stopped hosting teen night at the club, we switched to the roller rink in an attempt to find ways to connect with the fairer sex. On March 31, 1979, Brian asked if I was coming to the rink. He had a steady girlfriend at the time, which caused some hesitation on my part not wanting to be a third wheel, but I went anyway because it was the weekend.

His date had brought her friend and neighbor, Judy, to the rink that night and, after introducing us, she and I were left alone together as our mutual friends skated. She was kind enough to look past my bad hair and skate with me.

A Beatles song came on as we coasted around the oval and we discovered that we both loved their music—our first connection. This got me a second date. As we spent more time together, we found more commonalities and our relationship grew.

I owe Brian everything for making this connection and for opening the door to the 36 happiest years of my life.

I can look back over the years and see just how critical each connection that was made with me has given me the life I have today. Gatherings like WWDC, NSConference, C4, Çingleton, and others have provided opportunities to make lasting relationships with so many terrific people. I will always be grateful to the people who worked so hard to put together these events. People in tech can tend to be loners and we desperately need these bridges to help us build life-long relationships.

In addition to the connections others have made for me, I’ve tried to give back and introduce people over the years. Some of these have led to new connections that circled back around to me. It’s a beautiful thing.

I hope that this week in San Francisco has led to new relationships for you and that you are opening yourself up to the opportunity to make new connections. Through these, you may find a fantastic job, a best friend, or the love of your life. You never know. Get out there and connect.