The glam of maintaining

You really don’t have to disrupt, destroy, and exit to feel like you’ve accomplished something great in tech

Ka Wai Cheung
The Stories of DoneDone
4 min readMar 1, 2017

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The aspirations of many startup businesses typically follow an idealistic path through business strategy/disruption, exponential growth, and ultimate world domination. Whether you’re running a startup or you have some stake in its success, this mentality has become the universal template for what we all should want.

In truth, this is a tough plight. Broad stroke plans are often met with uncooperative realities. After all, there’s also a whole lot of luck involved to get the ideas out to market at just the right time, in just the right way, and in just the right places. And, when success does happen, the usual plan is to ditch the thing completely — almost always in some form of an exit strategy.

Society doesn’t applaud the exit strategy for most other life achievements. Those are usually called things like divorce, termination, or resignation.

Given the odds of this kind of success happening, the ultimate measure of what success is, and the amount of work (and the pace of that work) required to even open up the possibility for such success, natural human tendencies begin to take over.

Hire fast! Build teams quickly! Fail early! Pivot! Sprint! Pivot! Reinvent! Sprint again! At a certain point, the startup engine becomes the autonomous machine where the humans become the replaceable parts — jockeying around from startup to startup, no longer as interested in the maturation of a business as much as the daily free laundry service.

I’m just not interested in it.

My small taste of “the dream”

I, too, was swept up by the prospects of startup glory once. My first taste of this was as a college intern at a startup called PaxZone. This was a service which allowed users to ship online purchases to an affiliate — usually a small mom-and-pop shop down the street — to avoid missed packages at home. Under what would be considered modest funding by most standards, we launched in the fall of 1999. Our company had that familiar new startup smell —the felt of pool tables and that coat of lacquer on refurbished arcade machines. I even remember us even spending a morning debating what our NASDAQ symbol ought to be once we went public.

Ultimately, like most startups, the “how do you make money” part of the success equation wasn’t answered particularly well, so the company dissolved in the spring of 2001. Just in time for me to graduate from both college and the University of Startup Realities in the same season.

We were a long ways away from reaching the prototypical dreams of startup mentality, but nevertheless — even 17 years ago — they were largely the same: Exponential growth faster than we’d know how to handle it (“But that’s a good problem to have”) and an exit strategy.

Resetting fulfillment

I’d guess that many programmers in their mid-to-late-thirties grew up professionally in the world that I did. They entered the workforce at the auspicious heights of the original dot-com boom and subsequently tied success as a programmer to the fate of lofty ambitions. Some of us will continue down that route and might eventually achieve it. Or, hop from company to company hoping their ability to write an API wrapper will serendipitously find a home with a company that exits stage right.

But, I’ve found a different path. Some may consider it downright boring. With DoneDone, a very small group of us have come together over the past eight years to do something sustainable. I’ve been there from day one to day 2,500 — designing, coding, testing, writing, delegating, debating, responding, and slowly evolving an idea into a business that makes a few thousand people’s lives slightly easier daily. A business that’s grown modestly year-by-year.

The vast majority of those eight years have not been spent planning the exit strategy. Instead, they’ve been spent doing the next thing. Sometimes, that’s plugging up a recurring issue. Other times, it’s working on a small but valuable feature. Many times it’s writing an idea down to share. In between all of that are all the little (and sometimes ridiculous) things we have to do to simply maintain the business we are.

Don’t get me wrong. Maintenance is boring to talk about. There’s little fodder for the interested reader to chew on. But, I find the incredibly dull act of maintaining immensely gratifying. I find sustainability a worthwhile achievement. I find the constraints of our growth to be freeing. I don’t agree with the cliché that when your product is growing at a faster rate than you can handle, you have a good problem. For, even with all the modern SaaS amenities of auto-scaling infrastructure, we still haven’t figured out a way to auto-scale authenticity and trust. I think, by definition, you really can’t.

Sustainability’s already popular in another industry. Will it one day be in ours?

Sustainability has become an increasingly popular trend in other places — the environment and the food industry, to name a couple. The once-championed idea of fast food is no longer; the benefits of speed and artificiality were no longer a fair trade with the realities of what that does to your health and well-being in the long run.

That sure sounds familiar, doesn’t it?

So, while this industry continues to glamorize all the things that our startup isn’t, we’ll likely continue to forge our own path toward sustainability. One day, this might actually become the glamorous route.

But, either way, it’s the route I far prefer taking.

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Ka Wai Cheung
The Stories of DoneDone

I write about software, design, fatherhood, and nostalgia usually. Dad to a boy and a girl. Creator of donedone.com. More at kawaicheung.io.