The Lifecycle of a Dream

How dreams are like relationships

“If the path before you is clear, you’re probably on someone else’s.” - Joseph Campbell

As a kid, I held onto my dreams lightly. 

I went through them like shoes. First, I wanted to drive the bulldozer. And then the backhoe. Then, I wanted to be a professional soccer player. Next, a teacher. I didn’t think twice as I moved from one dream to the next. There was no mourning, no attachment, not even hesitation. My dreams were changing as quickly as I was.

But that’s supposed to end as an adult. If we’re lucky, we discover our “true” passion early and relentlessly pursue that for the rest of our lives. Our cultural milieu revolves around people who have done just that, like athletes, artists, and musicians. Other people simply commit to something, like those in finance, law, or medicine. From my original post on Life’s Infinite Paths, “they made one hard decision that eliminated a thousand others. Now, their career paths have crystallized in front of them.”

I fall into neither of these camps. At 30, I have a general sense of direction and a number of things I’m passionate about, but I’m still trying to figure out exactly what I’d like to do in this life. It can feel overwhelming, like everyone is off running their races, and I’m wandering, stumbling, getting dizzy. 

It doesn’t help that, around 25, pressure mounts to commit to whatever life happens to be presenting us at that particular moment – a job, a partner, a city. Continued exploration becomes more expensive at this age, both socially and financially. To some people, it’s suddenly grossly immature. A form of childishness. To be an adult, it seems, is to bear the burden of choosing. And choosing one thing means not choosing infinite others. 

A Case of Mistaken Identity

This year, I chose to let go of a dream.

I’ve been preparing to start a tech company for most of the last decade. I’ve spent my 20s learning technical skills, building a network, and working at startups. Now would be the perfect opportunity to get started in earnest. I have everything I need. I’m at base camp, packed and ready to go. 

Except for one annoying thing: I don’t think I want to anymore. Over the last few years, I’ve been poking and prodding at this dream, finally asking myself the hard questions: Do I really want to pursue this dream? Where did it come from? Is it mine? 

I haven’t liked my answers. Or lack thereof. And so this dream has taken on the quality of a mirage. As I’ve gotten closer, it’s started to dissolve in front of me.

There’s the normal Resistance, of course. That small voice we all have that likes to chime in and generally make life difficult. It speaks up before I do just about anything: writing, exercising, doing my taxes, waking up before 7am. And I have enough founder friends to know that starting a tech company deserves healthy trepidation: it’s demanding, risky, and often all-consuming. So maybe my reluctance is just Resistance in disguise?

I don’t think so. If I'm honest with myself, I may just not be well-suited for trying to found the next unicorn. My genuine interests are academic: I enjoy things like reading, teaching, talking, and writing. I take my time with things – friends joke that I put the "slow" in Koslow. I consider things to a fault – you may have noticed – and second-guess myself often. These would all be liabilities in a founder. 

I also don’t have that special breed of relentless, starving ambition anymore. What once felt like a rolling boil now feels like a consistent simmer. That is to say, I feel more Fundamentally Okay now. I think meditation medicated me. Or maybe it was just getting a bit older. Probably both.

I wonder if this dream was ever genuine. Or if it was just a shiny thing I picked up in college, admired, and adopted as my own. I think it had little to do with the actual day-to-day work of being a founder, and everything to do with the identity of being a founder, and the benefits of that identity, like respect, status, purpose – the usual suspects. I didn’t realize then, but I see now, that my dreams should be downstream of what I want to do in the world, not borrowed ideas of who I want to become.  

So, now that I’ve put this dream aside, I’m left asking, what’s next? Where do I go instead? 

There’s a lot of comfort in having a personal narrative, a North Star that offers a sense of direction and orientation. Our identities, and the stories we create from them, help us locate our place in the world. And now I don’t have that. So it feels like a regression. Like I had a thing and then lost it, which has been jarring. 

It’s like a relationship ending, one that I’ve invested a lot of time and effort into. And it’s not a clean break. The part of me that wants to start a company is still there. He’s just been demoted. He used to be king, and now he’s pissed, and throwing a tantrum. So, on top of all the indecision, I’ve got to deal with him. Console him. Let him know it’ll all be OK. I assure him: I may still decide to start a company one day. But I won’t become a founder just for the costume, or to avoid the version of myself that is not one.

Beginning Again

As the unicorn founder dream has faded, a new one hasn’t magically swept in and replaced it. So I’m exploring again, running little experiments to try to find a new one. (I’ll talk more about this in a future post.) 

In my better moments, I see letting go of this dream as a good thing. A sign of progress. The dominant emotion is relief, like some deep part of me can finally relax, like I am more myself. The unicorn entrepreneur dream never quite fit, no matter how much I wanted it to. That’s probably why I procrastinated getting started for so long. This, in retrospect, was the first red flag. I read somewhere that doing is a sign of wanting. And it follows: maybe not doing is a sign of not wanting. 

It’s funny though. As I’ve put down the need to be a founder, I’ve also lost the resistance I felt toward it. Without that subtle sense of coercion – that hunger I mentioned – it feels like just one reasonable option among many others. Maybe I’ll pursue it; maybe I won’t. Either way seems fine now.

There’s a saying that we should never jump into a relationship just because we feel insecure being single. Maybe the same is true for dreams – that feeling okay without them can help us say yes to the right one.

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