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Kayaks and other weird metaphors

You buy yourself a kayak.

Some of your friends bought kayaks as well and they seem happy. You’d thought it’d be something cool to do. You’ve always seen yourself as a kayaker. You enjoy the idea of freedom it could give you. You also dream of becoming a famous competitive kayaker, like many you’ve read online. You’ve spent more hours that you care to admit in news.kaykercombinator.com reading up on kayaking. You feel you’re ready and you take the plunge.

Your friends and family advise you to be careful as it’s an expensive and time consuming hobby. But you carry on. They don’t have that ‘Disruptor of the seas’ mentality. You’ve bought yourself a two-seat kayak for expansion potential.

So you take your kayak to water the first time. It feels exciting and new. Some of your friends and family, who helped you finance your kayak, show up to your inauguration session. Even the local kayak-crunch news site appears and reports on your launch. You wave people goodbye as you start paddling out. Everyone seems proud of you and your accomplishment.

As you start paddling, your initial thrill is quickly replaced by some confusion. It’s actually pretty darn hard to paddle a kayak. The first few paddles just make you rotate in place instead of propelling you forward. This feels frustrating as nothing you’ve read online prepared you for this. You also realize that you didn’t think of where you wanted to go the first time you started kayking. You look at the horizon and define that as your end goal, or your ‘Vision’ as you think of it.

And you paddle.

As you figure out how to actually move in one direction, you become frustrated. You clearly underestimated the amount of paddling involved. You start thinking whether you could buy a silver paddle. One that you could paddle just once or twice and be done with all the boring effortful work. You think of your family and friends and you can’t help wonder of their expectations and whether you’re meeting them.

You decide to call it a day and to return home to rest. As you start to turn around, you start hearing rhythmic human voices not unlike an orchestra of people maintaining perfect tempo. From behind you, and as quickly as you could keep your kayak steady, a huge racing shell appears composed of a line of a dozen athletes all rowing in perfect sync. Their watercraft is shiny and slick as it displaces the water efficiently. Their blades are razor thin slicing the water without any noise or splatter. You can’t help but seeing a small logo on the side of the fast moving boat. It says Stripe.

You go home demolished. Not only you suck at kayaking but there are already others who are better than you. In the metaphorical gap between you and them, a cruise could pass. The comparison kills your motivation. You think again of your family and friends, specially the ones who put in some money to help out.


You decide that this is definitely a problem of speed. And you can most likely solve it with investment in better gear.

One thing you learned online was that there was a number of people specialized in investing in early kayakers like yourself who will then reap the benefits when you start winning competitions.

You try researching everything about the Stripe crew. Turns out an amazing group of investors backed them by supplying a rare type of Sequoia wood, fantastic for kayaks and shells. You reach out, but you don’t hear back. You realize that investors make money when they find star kayakers that can multiply their investment many times. In your current state, you understand why the best investors would not be interested in you.

And you paddle.

You don’t give up and you treat it as a numbers game. You end up finding an investor who’s willing to give you some resources. They ask for 50% of any future kayak earnings. It seems fine to you so you agree.

With your newfound money, you start your quest for speed! You invest in new lightweight paddles and some more fashionable gear that’s supposed to make you faster. You still have the image of that Stripe crew, working in unison, burned in your memory. You infer the only logical conclusion in order to be fast: “I’ll hire someone”.

You post a job ad. Turns out there are a lot of people looking for kayaking crewmates as well. You find one who is experienced enough. You don’t spend enough time interviewing, that’s for Captains of larger ships.

You have your first kayaking session together. You realize you spent your whole morning discussing how you were going to paddle together. Your crewmate asks for kayaking processes. Despite being just behind you in your kayak, your crewmate calls you some times for meetings, forcing you to turnaround in your kayak and face him to address problems (which you quickly learned is called one-on-ones). Part of you feels that you should really be just paddling. But you’re a bit afraid of losing your only crewmate so you oblige. He also calls you founder all the time and you secretly enjoy that.

And you paddle.

One day your crewmate asks for a one-on-one to discuss direction. You point inaccurately at the horizon which clearly leaves the crewmate unsatisfied. You start feeling that your crewmate secretly thinks you’re bad at commanding a kayak. Or maybe that’s you thinking, it’s hard to tell.

Once a week the new investor calls you, many times when you’re at sea, asking for thorough details of any trip you make. The investor also asks you when do you think you’d be ready to start winning competitions. The more you know about kayaking the more you understand how far you are from winning any competition. But you still tell them ‘very soon, 6 months we’ll be ready’. The crewmate alerts you to the fact that you’re still not fast enough and that winning a competition is lunacy.

One day you turn back, in your routine one-on-ones, and your crew mates says: “We have to talk about titles”. You become confused. You never thought of titles before, you were just thinking of paddling. But you fear losing your crewmate. So you appoint your crewmate as Chief Observer Officer, after his amazing talent for avoiding rocks at sea and alerting you of them.

And you paddle.

One day you and your crewmate pass by a turned kayak. You see people angry arguing in the water. You stop by and ask them what went wrong. One person screams back at you:

- It was ”kayak-water” fit. We couldn’t get the kayak to go fast enough in the water. We then started arguing and the kayak turned over.

You stay near them long enough to see a boat arriving saving the crew. The last thing you see is the founder writing a page on a book that says ‘Medium postmortems’.


Each day brings a new kayaking session and each day is as unremarkable as the day before. You feel frustration in your crewmate as there were clearly expectations of being much faster and ready for competition. Your investor, who was first calm, now seems nervous when you talk. You don’t think your speed resembles anything required to compete. But you feel pressure and so you launch your enterprise into competition.

You fail miserably. You end up second to last and only because the crew in last place started fighting with each other and their kayak turned over.

This becomes a huge blow to your team. No one speaks about it but you know that people are disappointed. You obviously feel like it’s your fault. You want to find an easy reason for not being fast enough, but it’s hard to pin point anything. Your crewmate, who started as enthusiastic, now seems lethargic and non engaged. Your investor, who once cared enough to call you every day, invested in another faster crew. Beneath it all, your self esteem is low. Your arms seem more tired than usual when you paddle, as if they are burning-out more easily.

But you carry on paddling.

One morning your crewmate announces he’s leaving the team. He’s found a better position in a crew that can win competitions. You decide to give it one final kayaking session. For a moment he actually seems happy, making you believe that he wants to stay with you and work on your team. But you discover that the reason for happiness is the prospect of change. You wonder if you should change as well. Your loss aversion makes you hate your now ex-crewmate.

You think back to when you first started kayaking. You have conversations with the friends who seemed like they had it all figured out. You discover that they were going through the very same things you are now going through. You actually feel normal but not in any way better.


You take a long time before going back to the water. You wonder where is the freedom you were promised. Your kayak feels more like an anchor every day. You resent kayaking for making you feel like crap.

The expectation of others, which started as a weight on your shoulders, is not there anymore which somehow feels worse.

You realize that ”sunk cost fallacy” is weirdly poetic in your kayaking situation and so you decide to give it another try. You decide to go back to basics and just focus on your paddling.

Your eagerness for being fast still rings in your head like a nagging voice telling you you’re going nowhere.
And you paddle.

You remember the expectations people had of you and your frustration in not meeting them.
And you paddle.

You think about the investor who no longer cares which feels good, because no one’s bothering you, but bad, because you’re not important enough for him to bother you.
And you paddle.

You think about your ex crewmate. You think about all the ways you’ve failed that person. You think about the things you should have done better and the things you should have said. You feel sad to feel dumped.
And you paddle some more

You no longer dream of becoming big and you manage your own expectations. You start thinking of another hobby. ‘Maybe Skating would make me feel better’

And, all of the sudden, you look back to see that you went farther than ever before. As your arms feel sorer than you’ve felt before, you figure out that the best way to actually get somewhere is through small consistent paddle strokes.

You look at the horizon. The sun fades on it. You point your kayak in that direction and, in that sunset, it dawns on you that you’ll never reach it.

And you paddle. And you actually feel happy doing it.

decisions
Photo by Patrick Fore