I’ll never forget a deep sea fishing adventure I had over twenty years ago. It all started at business school during orientation week when I befriended a classmate from Florida over a couple beers. Jon and I became pretty good friends over those two years and would often get together to shoot the breeze about school, about careers, about life. It became quickly apparent that one of his passions was deep sea fishing. Correct that. His ONLY passion seemed to be deep sea fishing. He would somehow find a way to work the topic into just about any conversation. I couldn’t really relate but to each their own. Well, he was very interested in sharing his passion with me. Apparently, I had no idea what I was missing. So he invited me to crash at his house in Ft Lauderdale over the winter break and to experience this magnificent sport of deep sea fishing (to this day I still cringe when I use the words “fishing” and “sport” in the same sentence). I politely declined. I explained that I had already committed to the infinitely more riveting sport of watching paint dry. I thought that would be the end of that. I thought wrong. Not wanting to take no for an answer, I got the same invite over spring break that year and again over the following year’s winter and spring breaks. No, no and no. Finally, as we headed into our final week of school, Jon asked me one last time. At this point he was practically begging. I was starting to feel pretty guilty for repeatedly blowing him off those last couple years and I had exhausted my go-to list of excuses so this time I reluctantly accepted his invitation. And off to sunny Florida we went.
One week later we were aboard Jon’s fishing boat in Ft Lauderdale at the crack of dawn heading straight out to sea. I had explained that I knew literally nothing about fishing but he wasn’t too concerned. He would teach me everything I needed to know. “How awesome is that sunrise”? Jon asked somewhat rhetorically from behind the wheel. I had to admit, the beautiful orange hue stretching across the horizon was something pretty special that you don’t see every day. But my mind was elsewhere. We had already been cruising for about a half hour by this time and I was wondering just how much longer we had. Jon tried to reassure me. “Don’t worry. We’ll get there when we get there. Just sit back, relax and enjoy the scenery.”
After what felt like an eternity, we finally arrived at our destination. I looked around. Nothing but ocean in every direction as far as the eye could see. Not sure why this spot was any more auspicious than any of the prior points along our ninety minute route. It all looked the same to me. But somehow this was the magical spot which would bless us with all kinds of incredible fish. Who was I to argue? So Jon pulls out some bait from his tackle box, attaches it to his line, casts it out into the sea and sets the pole into a holder affixed at the edge of the boat. He then repeats this exercise with my pole. With that, he disappears to the interior of the boat. He’s back a couple minutes later with a six pack in his hand (Bud Light if memory serves). He pops one open and hands it to me and then helps himself to one. I turned toward Jon with what I’m sure was a bewildered look on my face. “So now what?” I inquired. “This is the easy part,” Jon assured me. “Now we just hang out. And drink. And wait.”
I did as I was told. I had never been one to refuse an ice cold beer on a hot summer day and I wasn’t about to start. So we hung out. We drank. We laughed. And we talked. We talked about everything under the sun (pardon the pun). Politics. Sports. Business. Family. Careers. Life. You name it. We pretty much just sat there drinking and chatting away for hours on end. Eight hours must have passed by the time Jon looked at his watch and realized it was time to be heading back home. As he was putting away the poles, it occurred to me that we never got so much as a nibble from any fish the entire time we were out there. I tried to console him, assuming he’d be a bit disappointed in not being able to deliver that memorable fishing expedition he had promised me. “Don’t worry about how the day went Jon. No big deal. Hope you’re not too bummed about it.” He turned in my direction wearing a huge grin. “Are you kidding me? I had a blast. That was awesome! So what did you think?” What did I think? He couldn’t be serious. Two years of convincing me of the opportunity of a lifetime and here we were accomplishing nothing but hanging out the entire day. And he wanted to know what I thought? Then I sat there for a moment in silence reflecting on that very thought… Two good friends in the middle of the majestic ocean on a beautiful crystal clear day just hanging out, drinking, talking and enjoying each other’s company. It’s like a light switch suddenly got turned on inside my head and it started to all make sense to me. A smile slowly crept across my face as I patted Jon on the back. “Yes. It was indeed an awesome trip Jon. I’m really glad we did this.”
I suspect I may not be alone in thinking that we can sometimes become a little over obsessed with goal setting. Don’t get me wrong. There’s nothing wrong with goals per se. Realistic goals help guide us and motivate us. They can inspire us to accomplish great things. But goals aren’t the be-all and end-all. The problem is that with so much of our focus on the destination, we may occasionally lose site of the enjoyment and growth that come along with the journey. The ultimate destination may or may not ever happen. The future is simply an unknown. But the journey is always guaranteed.
I recall many a conversations with entrepreneurs from the first Internet bubble who didn’t quite time it just right. The market had turned south before they had an opportunity to exit and cash out. Their sentiment was much stronger than just frustration or disappointment. Their feelings were much more vitriolic and could be summed up on one word: regret. “I can’t believe I wasted three years of my life on that f*cking startup!” was a common statement I would hear over and over. “I would have made a lot more money in consulting or banking.” I was taken aback. Surely they had a fascinating experience trying to create the next great Apple or Microsoft. They must have relished the autonomy, speed, exhilaration and disruption that a venture-backed startup affords, despite not having a lucrative, storybook ending. I imagine they must have learned more in those two or three years than they would have in a decade in any corporate environment. Apparently that amazing experience was all for naught. At the end of the day, I guess all that really mattered to them was that elusive pot of gold at the end of the rainbow.
Let’s be honest. Who wouldn’t be a little bitter when the outcome doesn’t necessarily feel correlated to the effort exerted? To think that it’s not just about the idea, the team, the strategy, the capital raised, the partnerships and the traction but rather some kind of uncontrollable and unpredictable luck and timing. Not that all those elements aren’t critical for success but most every venture-funded startup has those. Those attributes are just the ante to play. You could do a lot to reduce risk but never eliminate it. Not even close. Ultimately, you would have a lot less control over the end game than you ever imagined going into it. It’s tough to accept. I get it. I’ve been there. But to not appreciate any of the adventure along the way is really unfortunate. After all, the euphoria from going public or getting acquired is ephemeral but the wisdom and maturity and growth and learning that you experienced while building the company will last a lifetime.
We took a family car trip to Chicago recently and like every other parent before us, we too had to endure our share of “are we almost there yet?”s from the junior members of the household sitting in the back row. (The irony didn’t escape me that this was the exact same line of questioning I had for my friend Jon on the boat some twenty years earlier.) After about the tenth request for an ETA (all in the first hour of our twelve hour trip mind you) where my strategy of feigning deafness apparently wasn’t working, I gazed at my son through the rear view mirror and replied, “No. We’re not almost there. In fact, we’ll never ever be there. Because no matter where we are, we’ll always be right here. ” I figured that philosophical rebuttal ought to teach him a thing or two about the importance of living in the present. He’d now cease the repetitive questioning about the timing of the destination and just appreciate the beauty of the journey. “Whatever dad. So are we almost there yet?” Oh well. I tried.