The Boat

I once worked with a young CEO- we’ll call him Sam.  When we first met, he was in graduate school at MIT studying business after having studied physics after having studied engineering.  As an underaged high school wiz, he blew up the SATs, 800s, all a piece of cake.  At 16, he attended the University of Michigan on a full academic scholarship, and after four years, he achieved degrees in both physics and engineering.  Sam is a very smart guy.

His first job was with a well-known mega-global technology juggernaut.  They recruited him hard, paid him a big signing bonus, enough to pay cash to cover half a house.  It was good money, but his boss was an uptight autocrat.  The group he worked with was full of bureaucratic sycophants and after three years of being treated like a ten year old, he’d had enough.  He couldn’t stand being penned in, pinned down, often yelled at, fitted with a straight jacket, then another, then another, buckles and straps everywhere.  Corporate life was the shits he told his friends.  Finally, sensing that he was doing more harm to his career than good, he took advantage of his financial security (he hadn’t bought the house; instead, he had parked the bonus in Apple stock as it happens).

Off went Sam to MIT to get his MBA.  It wasn’t that he needed to go to school to learn what MBA students learn: he could have inhaled the whole curriculum in four months of determined reading.  Sam wanted the credential, the big ticket.  He wanted an MBA from MIT so he could be a boss, The Boss actually. From now on, he would set his own agenda thank you!  Did I mention that he hated being told what to do?

Our first meeting was at a workshop for young entrepreneurs.  This was a two day affair offered to Boston area MBA students.  He was at MIT, and I was one of the presenters.  My bit was to spend a couple of hours as the old fart in a chair who tells what it’s really like to really start a business while students pepper me with questions.  As I recall, there were 50 or so attendees, but Sam, in particular, stood out.  First of all he was very young, even in a decidedly young crowd.  But what made him most memorable was how he kept asking about being in control, about being the boss, and about not wanting to work for others.  It was as if he was asking me to tell him how to absolutely guarantee a kind of complete freedom from the tyranny of any hint of supervision.  Finally I relented, thought about how to put it and then told him, along with the rest of the group, that the only way one could be the type of uber-insulated-boss, immune from all forms of supervision was to start your own business, using your own money.  Every other job I knew of, including being a hired gun CEO, featured one or more bosses, lots of politics, and attendant restrictions.

Sam completed his MBA and within three months did start his own business, one which wrote and sold enterprise software.  He funded it with his own money, selling some of his Apple stock and leaving the rest as collateral to secure a modest line of credit.  By dint of energy, determination, and a couple of very good ideas about the software large businesses really need, he blew past the startup stage in six months to create a robust software development business. By the time he and I met for a second time, he had five years of being his own boss under his belt.  It suited him.  He was very successful, the business was thriving, and now he wanted to talk, not about control, but about an unsettling experience that made him wonder if he was in danger of losing the whole thing.

He sat in a chair opposite me, still trim, a wiry looking guy.  He was never still, jiggling legs, hands that move in sync with his talking, twisting in the chair, fingers flashing, a Midwestern boy with the gestures of an Italian in high spirits, body shifting as he spoke.  His eyes brown and gold, scanned and moved like the hands, but almost never made eye contact; in fact, when he talked, he most often looked off over my head, or over my right shoulder, giving the sense that he was talking at me, not to me.

Samuel can be funny.  He is loquacious, impatient, and as you might expect, he radiates a kind of certainty.  He dresses the part of perpetual student, jeans, black high top Keds, a fitted red shirt with “Oh Canada” emblazoned in white across his chest, and sports a black plastic digital watch that beeps at fifty-five minutes after the hour.

We were talking about the end, as in when was it time to sell. It seems he knew someone who knew someone who knew I would be in Boston for a conference.  So he sent me a text “met you long time ago, like your stuff, could you come to Salem for a chat on Friday after your meetings”.   Salem Mass was as far as he’d gotten after leaving MIT.  One of the his many good business ideas was to forgo the big home office model and build a mostly virtual business, one which featured the best and the brightest developers, scattered at first across North America, and later around the world.  He pulled all of them and their work together with technology and held them on course with what could only be described as an acute vision for enterprise software. He also took advantage of his natural affinity for finding people who, like himself, were very smart and who didn’t particularly like close proximity with others and mostly didn’t like close supervision.  It worked.

We met at his modest global headquarters, the mother-ship, a skeletal office in a nondescript business park just outside of Salem.  We were in a kind of mixed living room, meeting room, couches and chairs on a gray carpeted floor, a white board ceiling to floor running the length of the space, windows on two other walls, the dull glow of early winter in Salem lighting the scene.  Samuel and I were seated in modern white leather easy chairs facing each other across a low black drum table, his side with a can of red bull open at the ready.  He started our meeting by briskly giving my hand one shake then falling backward into his chair and saying: “I’m glad you could come.  I want to talk about me and the job, the end and my gut.  I’m worried.

“About what?”

“I’m afraid I could be losing my grip, my gut, and I think maybe I should sell.

“Seems to me you’re doing a lot of the right things.  I read your website: you’re on a roll, congratulations!”

“Yeah, we are.  But what I’m worried about is that I keep getting blindsided.  We are successful, we are making a lot of money, but there are way too many surprises.  The bigger we get, the less I can predict what is going to happen.  I have never been unsure of myself, until now.”  He pushed his hand out as if to fend off some approaching or menacing force.  He finished the motion by leaning forward, grabbing the red bull and taking a swig, and then as if in slow motion, he quite deliberately, uncharacteristically carefully, placed the can gently on the black table top.  “Did I tell you about the boat?

“Not that I remember.”

“Well you must be the only person who met me back in the day that I didn’t tell.   I’m from the Midwest, and one thing about us Midwest kids is that many of us dream about getting out of the Midwest!  My dream was to leave the Midwest to live on a boat, on some ocean, a pretty big boat, but more than anything I wanted to live on a boat.”

“How did it go?”


“How did it go, your boat, I presume you can afford one by now.”

“Lousy.  That was the beginning of my problem.  I think you must know lots of guys like me – you must have met a bunch, a whole bunch, and I need to tap into that.  See, I’m beginning to think I just got lucky, and if I don’t figure out this job soon, the whole thing will just go up in smoke.  It just freaks me out.  What I want to know is do the other guys feel like this?

“The short answer is yes, many do.”

“Okay, so what do they do?  How do they learn what to do?  And what do they do if they discover a fatal flaw, in themselves?

“What type of fatal flaw?”

Sam breathed in and exhaled, like a sprinter tensing for the start pistol, paused and then spoke.  “Since I was a kid I wanted to live on a boat.  And since I was a kid I was told: dream your dreams and they will come true, right?  Just put it out there, whatever you want, and you can get it, somehow, some way if you just work hard enough and have a little luck, you can get almost anything!  So for me it was living on a boat.”

“Okay,” I said.

“Well first of all I got married, Belinda, bright, beautiful, just a spectacular parson.  That’s a good thing.  Next I build this place up. We’re doing really well, and after a while it’s pretty clear I don’t have to do everything, and I have some time, so I start looking at boats, and I take some vacations, and that’s how it happened.”

“The boat or the vacation,” I asked?

Samuel had a way of hearing what you said and ignoring what you said by just plowing on: this was one of those moments.  “Belinda and I took this trip to Scandinavia, a place as far from the Midwest as you can be, don’t you think?  Anyhow, spectacular place, amazing people, loved it.” At this point he stood up, took a swig of Red Bull, put the can back on the drum table and began pacing back and forth behind his chair as he talked, looking over at me as from time to time, checking to see if I was listening.  I was listening.

“So,” he continued, “we’re in Copenhagen and are scheduled to take a ferry to Oslo – it was part of a tour.  For some stupid reason I imagined a ferry boat like maybe the Staten Island Ferry or something, know what I mean, stand out on the car deck, travel for about an hour or so and there you are?  Only it’s a hell of a long way across open sea between Copenhagen and Oslo, and the so called ferry is a giant cruise ship, I mean giant, and it takes about 18 hours to make the trip.  So you get on the ferry at like 3:00PM and eat and gamble and drink and then go to sleep, and wake up as you dock in Oslo the next morning. It’s really a mini cruise.  I didn’t know that when we booked the trip.  I also didn’t know about the cabins either, because just like a cruise ship, there are cabins with a view and cabins without a view: in fact there are even cabins without windows; somehow we got one of those.”

He paused for effect, and then continued.  “Okay, we board the ship with a million other people, we dump our luggage in our small cabin, have a giant smorgasbord meal, gamble a little, see a show and finally Belinda and I turn in.  That’s when it dawns on me that our cabin was one of the windowless ones, a little like a clean white windowless super eight motel room, only much smaller.  It felt a little creepy, but I got into bed and read for a bit, I like to read before I go to sleep.  Then I noticed the vibration of the big engines that drive the ship, and then I noticed the rising and falling, tilting left and right.   Of course I think, the ship is on the open sea, waves!  I didn’t like the feeling, again, made me feel a little creepy and now queasy, but it wasn’t so bad, and as I read I got sleepy and dozed off.”

Sam stopped pacing, looked at me for a long moment, direct eye contact, then slowly sat down in his chair again, steepling his fingers, then tapping his forefingers together, tap, tap, tap, eyes unblinking, holding my attention.

“Sometime in the middle of the night I woke up,” he continued, talking slowly now, voice lower, quieter than before, tap, tap, tap.  “There was a small night light on the wall in our cabin.  I woke up, and saw this glow from the little light.  It was so low on the wall I couldn’t see the light itself, just this ghost like glow, and then I felt the vibrations again, the engines, and the room moved.  We were swaying, and then I felt an emptiness, a hollowness in my chest, like I couldn’t get enough air, like I was being asphyxiated.  I tried to inhale deeper, a couple of times, but it didn’t seem to help much.  Then I swear to god I saw the wall with the glow move… inward, toward us.  It was coming toward me.  I sat up, breathing harder now, and when I did, the wall stopped moving, and it seemed to snap back to where it was supposed to be.  Then after a minute or so, still gasping for air and sweating, the walls on the left and the right started to move in, and I had a vision of us being crushed.  I breathed harder, shook my head, but the walls kept moving in and then the wall in front of me started moving again too and that was it, I just lost it. I jumped out of bed, yelling like a crazy guy, pulled Belinda up by her arms, and dragged her to the door.  Of course the damn thing was locked, I was yelling at it and I almost ripped the handle off until I found the latch, and dragged her out into the hall finally breathing a little better, and I ran pulling her, took her all the way down the passage way, up a circular staircase, out to a giant lounge, lights still on but empty, us in our pajamas, me drenched in sweat but finally getting enough air into my lungs, finally believing that I might live through the night.  It was freaked, horrible!  Just horrible.”

“Wow,” I said.  “What did Belinda say about this?”

“She knew, that’s part of the problem, she knew.”

“Knew what?”

“She somehow knew I was claustrophobic, only she never mentioned it.”

“Did you know?”

“Hell no, I wanted to live on a boat remember?  Do you think a person who knew he was freaked out by small spaces would want to live on a boat?  That’s what I mean.  I thought it would be the greatest thing ever to live on a boat, couldn’t be happier right?  Only no, it would be the worst type of hell, what was I thinking?  That’s the flaw, my flaw: it just opened up right there in front of me, no, inside me.

“So you had an episode like this before?”

“No, never. I didn’t have a clue, ever, but Belinda did.  She said she’d suspected it almost right from the beginning, when we started dating.  Later when we were talking about it, she said she never mentioned it because she thought I knew I was claustrophobic, only I was sensitive about it, trying to hide it from her.  But the point is she knew it, and I didn’t!  That’s what worries me.  So my question for you is what else is going on that I don’t know about?  What do other CEOs say?  Does this shit happen to them?  Maybe I got the whole thing wrong?   What if I’m building a business, working my ass off and heading for some big disaster, a breakdown or something?  Does this happen to other people like me?  You know what? I’m not so sure I want to be successful, if this is what it’s like.  I like to breath, I like space, light, freedom, and above all I don’t have any confidence in myself, I don’t want to crash!”

“Well Sam, look, you always wanted to live on a boat, it was a dream, a big deal, and fit right in with your desire to be free.  And in the abstract, living on a boat makes sense.  Only you discovered something about yourself that you weren’t aware of, a surprise.  If you think about it, again, noting your dislike of supervision, you might say that people trying to control you also made you feel symptoms of claustrophobia, only you’ve arranged your life so you can always get away from being told what to do, at least in your work.  On the ferry from Copenhagen to Oslo there was no getting away.  You had a full on episode of being closed in, and your conscious and subconscious lashed out!  You were blind because you focused on the dream of the boat, of success, and unconsciously avoided situations that would trigger claustrophobic feelings, that’s all.  The good news is you found out before you bought the boat.

We both laughed, “and the better news is you met Belinda, who seems to know you pretty well.”

“Samuel shook his head slowly.  “Yea, that’s for sure, but I’m not so sure she likes being dragged in her pajamas around a cruise ship in the middle of the night.   But look, what if I am just lucky, lucky so far I mean, what if I don’t really know how to run a business, and right around the corner is the next big surprise about myself, whatever that is?  I don’t want any more surprises like this….  I want to live a measured life, no surprises!  How can I do that?  How do other people you talk to do that?

“They don’t.”

“What do you mean — all of these CEOs are neurotic?  All of the people who build business are nuts and don’t know it?”

“We’re all what you call neurotic, to some extent, because we’re all human.  Being smart enough to start a successful business doesn’t excuse you from being human.”

“Yes but you need to control yourself, you need to control your company.”

“Okay, but the control part doesn’t trump being human, and that’s the real challenge.  To go on an adventure as a human, as the experience on the boat showed, there’s a lot to learn, from the inside and from the outside.”

“I didn’t know that.”

“Actually I think you did, only you became so enamored with the idea that you were controlling events that you thought that success meant you could control everything.  Only you can’t — no one can.  You made a wrong assumption about yourself and the business: you believed as you became more successful there would be fewer surprises, as you call them, because you were managing and controlling yourself and the business.  But there is more to each of us than we know, as we discover the world, we are also learning about ourselves. And one of those discoveries was that you are claustrophobic.

“God!  I am losing it.”

“I know this is uncomfortable for you, but you aren’t losing it — you’re just learning in a world full of surprises.”

He took a deep breath, exhaled, shook his head, looked at me hard.  We sat there for a couple of minutes not talking.  Finally he asked “so what do I do now?”

“What do you want to do?”

“I really feel lost, I’ve lost faith in my gut, my instincts, and worse, I don’t really know what I want.”

“Actually I think you do.  You have good instincts, you’ve built a very successful business, attracted really good people to work with you and you’re happily married to someone who seems to be a great partner.  That’s more progress than many people make in a lifetime.”

“Yeah but you’re conveniently leaving out the whole neurotic thing, and my lost confidence.”

“No, I’m not leaving it out: you left it out.  You have some wildly unrealistic expectations about yourself, that you can become strong and successful enough to eliminate fear, eliminate surprises.  It’s an interesting idea, but it’s never true, because no matter how smart you are or how hard you work, you are, just like the rest of us, a regular human being.  The trick isn’t to eliminate surprises: the trick is to live fully knowing you will be surprised.”

“God,” well okay, what if I sell, what then?”

“Then you will sell, and have more money.  But you will still be claustrophobic, and life will still have plenty of surprises.”

“Do you think I‘ve lost my touch?”

“No, I don’t.  I just think you aren’t used to being surprised, as you put it.  You have done a lot of good stuff here.

“I need some time to think about this.”

So he did think.

Two months after our conversation he texted me “No reason to sell, just getting to the good part, thx, S.”

Three years later, from a Christmas card, I learned that Belinda and Sam had two children who no doubt provided them with wave after wave of surprises (which is of course no surprise to any of us who know something about children).  The handwritten note on the card read “having a blast, thanks for everything… Sam, Belinda, Sam Jr. and Michelle.”

So Sam, smart lad, was one of those people who could work hard enough and experience enough luck to be “on a run” as they say.  He was having a good outing and everything seemed to be going his way.  He then, luckily, experienced the walls closing in and the shock of it set his feet more firmly on the ground, in the real world where full lives are populated by plenty of surprises – some good, some challenging.  Sam, with his feet on the ground, a ton of determination, Belinda as a partner, both full of good ideas, were moving into a new phase, more open to the world as it is.  And Sam, well he had shed the myth that he was in control of his world, for the experience of living in the world in which he just happened to have co-created a family community and a business community.

Did you like this? Share it:
This entry was posted in Entrepreneurs & Managers, Leadership, Leaping, Live your Life, Navigate the Rivers, Survival and tagged , , , , , , , . Bookmark the permalink.

One Response to The Boat

  1. Dean Heathcote says:

    For me ‘being scared’ is often a critical ingredient to success. Pushing through it is exhilarating, followed by, repeat …. repeat. Great story and appreciate the reminder.

Leave a Reply

Your email address will not be published. Required fields are marked *