When Our Ambition is Our Enemy

Our Founder ambition is our greatest source of strength — but can also be our greatest enemy.

While being a startup Founder and having ambition are nearly synonymous, that doesn't mean the very same ambition that drives us to climb mountains can't also push us off a cliff!

I know this because I've lived it many times. I wasn't born the smartest, the most privileged, or the most talented. But I was born with two gifts — ambition and a willingness to work insanely hard. When you're starting from nothing, those gifts mean everything. Yet, what we tend to overlook is that those "gifts" have some major drawbacks that come back to haunt us later on.

Ambition Has No Shut-Off Valve

When I was 19 and starting my first company, I could let my ambition run wild because, frankly, it only had an upside. For the first four years of my startup career, I didn't take any days off (including weekends), didn't celebrate holidays, and didn't see my family. All I did was work—all the time, no questions asked.

At the time, I was proud of that hard work, and there is a part of me that still feels that way as I write this 30 years later. But what I was doing was setting in motion a precedent of hard work that I would spend the rest of my life trying (unsuccessfully) to unwind. I would use that work as a benchmark for ambition.

What I did, without realizing it, was set my benchmark so high, with essentially no shut-off valve, that the only limiter for my effort would be failure. That's not OK. Let me repeat this in case anyone skips this part — it is NOT OK for us to run ourselves to nothing but failure. As I'm writing this, I haven't taken a break in 9 months, and I'm about to go on vacation tomorrow, so I'm kind of writing this to myself ;)

Ambition Costs Us Our Health

Let's talk about what "failure" looks like when our ambition has no shut-off valve. It means our health quits. If you take all other things off the table, the last thing we have is our health. Even if we're broke, we can still keep on doing something every day until our bodies give out. I know because I've tested this extensively.

Many of my Founder friends (I can't think of anyone who isn't on this list, sadly) are sacrificing their health for their wealth, as if the latter will provide an ROI to the loss of the former. For many of us, we're still too young to understand what a massively bad bet that is. Our health isn't a currency we can place bets with; it's the backup to survive when our real currency doesn't exist anymore.

If we want to remain ambitious, we have to be healthy. It's a simple concept, yet for many of us we consistently fail on that equation over and over. How many of you digesting this right now can say that you're both at peak physical health and maximum ambition? And don't point to the “stars of social media” on this one because I hear all the stories from those folks behind the scenes and I can tell you firsthand they are all their own versions of messed up.

Ambition Clouds Our Judgment

What we lose along with our health is our judgment. I'm not saying I envy unambitious people, but I can say I envy their common sense. No rational person would forgo seeing their families for years to do a job. My ambition simply clouds my judgment. In my mind, if something can be achieved then it must be done. The cost is merely the byproduct of the goal, and that math is the curse of my ambition.

When I was 37, after nearly 20 nonstop years of building startups, my heart stopped while I was on the highway behind the wheel of my car. It only stopped for a moment, but let me tell you — you can't mistake your heart-stopping. My ambition caused that, plain and simple. It allowed me to overlook every telltale sign that I was running myself into the ground, and what's worse — it had me high-fiving myself along the way.

The only sane person who got through to me was my wife. She said, "You're doing all of these things because you can, not because you should." Of course, she was right. My ambition, which allowed me to tackle anything, was left unchecked and became my greatest demon—what constantly pushed me to failure.

Our ambition is only an asset up until the point where we let it become a liability. It’s our job to keep that ambition in check so we can be around long enough to enjoy the benefits of it.

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