From Zero-Sum to A Rising Tide

“Let not to get a living be thy trade, but thy sport.” -Henry David Thoreau

I’ve already written about how I think “follow your dreams” is horrible career advice for most people. So what am I doing with this Thoreau quote leading the post?

Let me explain. Following your dreams can be a recipe for disappointment if you don’t at least keep one foot in contact with reality. The vicissitudes and practicalities of earning a comfortable living don’t care about your feelings.

However, this does not incriminate or invalidate the possession of dreams in the first place. Having a dream and working hard to make it a reality is much different from frolicking to the end of the rainbow only to find that there’s no pot of gold and you’re late on your rent.

My Own Journey

When I was on Wall Street, I slowly became accustomed to the habit of selling my time for money. I was like the proverbial frog being boiled in a pot of water. The gradual change eventually resulted in an entrenched belief that selling time for money was all that work could be.

I can chalk part of this up to personal taste. To be clear, there was so much to love about that first job. It was exciting, intellectually stimulating, and I was surrounded by smart people. I didn’t find it fulfilling, but fulfillment could wait. Or could it?

Now that I’ve had ample time to reflect (and ample experience with another way of being), I can appreciate one dynamic that was definitely in play. My creeping dissatisfaction stemmed largely from the fact that I viewed what I was doing as a zero-sum game.

Cog

I was a cog in a well-oiled machine. To be sure, this was a great place to begin a career in the workforce. Being around world-class talent has immense benefits in terms of both education and motivation.

However, the drawback of being a cog in a high-performance machine is that the low-hanging fruit has mostly already been picked. That is, the market is established. High performance is driven mostly by increasing market share.

The size of the market is (mostly) exogenous, so success takes the form of being “top-tier” and increasing the percentage of business that comes to your firm to transact. If that sounds like gibberish to you, what it means is that for the most part, the amount of business being done is a given, and it is just a question of which bank gets to do the business.

Pie

The term “market share” involuntarily draws to mind the image of a pie chart. The goal: to get yourself (and your firm) a bigger slice.

When you’re young and honing your craft, this is plenty difficult, and presents a formidable obstacle against which to sharpen your acumen.

But somehow at the ripe old age of about 28, this wasn’t enough. To be clear, I hadn’t perfected that talent, but incremental progress on that goal didn’t have the resonance within my psyche that I might have hoped.

More Pie

At this point, you may be able to tell by the sub-headers that I have yet to eat breakfast. Hear me out, though.

When you approach a pie, there are a couple places your mind can go. What my first job was all about was the approach that says “I’m gonna get the biggest slice I can.” A very human response, and completely understandable.

It wasn’t until I began my second career (in entrepreneurship), that I realized there was a different approach. The pie was in a kitchen, and had obviously been baked by someone. I wonder if I could bake my own pie?

Insecurity

“But I’ve never baked a pie before. Who do I think I am?”

Well, for every pie, there is a baker. And for every baker, there is a first pie he or she ever baked. So who did they think they were?

The Difference

As my journey as an entrepreneur continues, I am appreciating a key difference between my present pursuit and that of my former career. Within the space of founders/entrepreneurs, there is a different mentality.

Sure, it’s always nice to get a bigger slice of a given pie, but the knee-jerk reaction of an entrepreneur is less constrained. The entrepreneur asks, “What if we could make the pie ten times bigger? Then the slice sizes wouldn’t matter as much.”

One approach emphasizes distribution. The other emphasizes production.

Alignment

Perhaps there are some people for whom focusing on distribution is enough. I am not one of them. It was only once I embarked on building something of my own that I experientially learned this about myself.

There is something inherent in producing something where nothing existed before that is immensely satisfying for me. I deeply suspect I’m not alone on this point. The fact is, pivoting to a career where production was the centerpiece was essential to the feeling of alignment I now feel with my work.

Tailwinds

On Wall Street, I had come to assume that competition was the central fact of economic life. Sure, there were positive-sum instances where we could truly “partner” with people, but at the end of the day, if Party A buys and Party B sells and the price goes up, it takes a lot of mental gymnastics to claim that both sides won.

In entrepreneurship space, however, the focus is much more geared toward growing all the pies. The zero-sum game mentality is replaced by a heaping helping of “a rising tide lifts all boats.”

When you’re a founder, to a certain extent, it doesn’t matter if you’re 25 or 65. If you have an interesting idea, people want to chat. Every founder has at some point been a first-time founder.

I’ve been astonished by the overwhelming generosity of erstwhile internet strangers who know what I’m going through and want to help out. In my old model of the world, these people should not be taking my call. But they do.

They know what it’s like, and they are dying to share the insights they have gleaned as they have thrashed through the jungle of building a company.

Aside

Entrepreneurship is not a panacea. I recently came across someone saying “Why would you want to work 8 hours a day for someone else when you could work 20 hours a day for yourself?” They weren’t entirely wrong.

Furthermore, starting a business is definitely not the only way to achieve fulfillment. It’s what’s working for me, but your mileage may vary. There are other abundantly fruitful ways to achieve fulfillment through work (like earning to give, working in a service-oriented industry, or joining a startup that someone else has started).

The general point of this post is not that entrepreneurship is the only way to participate in a positive-sum game. It is simply to point out that if you’re participating in something that feels like a zero-sum game, a different mode of work exists.

Thank You

To all those founders who continue to pay it forward, for me and for other entrepreneurs, thank you for your time and expertise.

And to all those who aspire to build something someday, please do know that entrepreneurship is different from other roles in so many wonderful ways. When you haven’t experienced it, it’s hard to believe. But if you feel like what you’re doing right now is zero-sum and you suspect that that’s not enough for you, there is another way to be. Do it on your own time and at your own pace, everyone is different.

What I can tell you from my own experience, though, is that the difference is enormous. Entrepreneurship is just plain different. If you’re thinking of building something, keep pulling at the thread. Make sure the timing is right for you, but when you’re ready, jump on in – the water is fine.

Ben Miller

Founder of ChroniFI

January 2022

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The foregoing are the opinions of the author and are for educational purposes only. They do not represent professional financial or investment advice. For financial advice, please consult a licensed financial professional.