What Will We Regret Risking for Our Startup?

I don't remember going to college. I know I went, but I don't remember anything about my college experience, because unlike everyone else, I was too busy working on my startup.

I remember rollerblading (1990s!) across the quad to class on a beautifully sunny day and watching a bunch of my friends playing volleyball and having an amazing time. I wanted to play so badly, but I didn't. I had to get through class so I could skate back to the office for an all-night coding session on a new client project.

This isn't a story about how that effort paid off (it did), this is a story of how badly I regret never having played that day. It's a story of how so many of my life experiences were mortgaged for the sake of building my startup, and how looking back, there were so many I regretted.

One-Shot at Once in a Lifetime

What I didn't realize at the time was that some experiences can't be replicated. It wasn't about playing volleyball which I thought I could do at any time in my life. It was about that moment of being 19 years old, with no other cares in the world other than playing my heart out that day. It was about looking back at that captured moment and knowing that it was the only time I would ever get that yearbook photo of life again.

We have tons of these moments, and all too often we forgo them in exchange for the good of our startups. It's yet another investment we make, among so many others, except there are certain investments we can never pay back. I can play volleyball whenever the hell I want now - but I don't want to. Not like I did when I was a 19-year-old student. That moment will never come back and let's be real, I'd look like a total creeper showing up as a middle-aged man to play volleyball on the quad, especially when I showed up in my rollerblades!

The Important Stuff is so Easy to Miss

Some mornings when I'm deep in thought and burning through cycles, my 4-year-old son nonchalantly walks up to me and tries to distract me by telling me to "look over there!" (I taught him this trick and he never fails to implement it.) When I do, he slaps my shoulder and says "Tag, you're it!" and sprints out of the room, awaiting the great chase to ensue.

Often, I jump up from my chair and chase him, sometimes I don't. But every time in the split second between being "it' and not being "it" I run a calculation in my mind of whether I have time to chase him, or whether that time needs to go toward my startup. Sometimes I tell him I can't chase him and I go back to working like crazy. I only regret the moments when I stay in my chair, and if I'm thinking beyond myself, someday, so will he.

Looking back over nearly 30 years of being a Founder, I can't think of a single case where my personal relationships got better while I invested all my time in my startups. What a shock, right? And yet, at some point, it's on me (and all of us as Founders) to draw a line on what costs we will no longer bear. What's funny is the costs are always pennies when spent, and million when totaled.

The Startup That Never Sleeps

For the past few decades, I haven't known what a weekend or a vacation looks like. When the day is over for everyone else, and they go back to living their lives as they should, I only downshift — I always have. I don't stop thinking about work, even if I'm not at my desk. When I'm on vacation I spend as much time on my laptop as I do on a sun chair. This is all entirely self-imposed, and no one else is to blame.

However, when I look back at all of those times when everyone else spent it having killer BBQs or enjoying amazing beaches all around the globe, you know what I remember the most? Hotel rooms and sleepless nights. I think of all of those missed opportunities I had to build amazing memories or enjoy mind-blowing experiences, but I didn't. I spent them mentally checked out from the very moments that I was working so hard to eventually enjoy. At no point do I look back and say "I'm glad I spent more time with my laptop in the hotel room."

At the time I'm sure I had good reasons (not really) for why I needed to make those sacrifices, but when I look back, over the span of a long, long time, there's no possible way. I'm sure some level of that dedication led to some level of success, but I honestly can't say that the risk was worth it. It may have been, but I honestly can't be sure.

What I've found (and as I write this) what you, my fellow Founders, may be assessing is that there are certain risks and investments we can bear, others that simply aren't worth it. Not every investment has a payback, and not every missed opportunity has another behind it. Our startups can provide a ton of upside with the right sacrifice, but it assumes those sacrifices can be paid back with a startup.

In Case You Missed It

Don't Work Long Hours, Work Efficient Hours Let's stop being "long hours" champions and start being proud of how much we can do in as few hours as possible — not as many hours as we can sacrifice.

How to Make Potential Failure Less Scar‪y‬ (podcast) While your mind can make it seem bigger than it is, most people won’t remember when a business shuts down — and processing your emotions includes assessing your failure to get back up!

Optimizing for Productivity. Working through peak productivity is easy. It’s the valleys that we’re concerned about. The key is to plan for and optimize the valleys so we can recharge effectively.