I Can't Have That — And That's OK

A few years back I was driving through a windy street of Bel-Air with my wife, looking at houses. If you ever want to feel ridiculously poor, I encourage you to do the same.

During our home tour we drove up beside a house under construction that was so big, we thought it was a hotel. We just kept driving around the perimeter of the house, and it just kept going! Our realtor told us it was the future home of Elon Musk.

A younger version of me would have said "Someday I'm going to have that house!" and believed wholeheartedly that there were some future series of events that would lead to that outcome. It's the blessing and curse of being a Founder I think.

I turned to my wife and said "I can't have that — and that's OK." Let me explain why that was such a leap for me.

Ambition versus Conditions

I used to think that ambition alone was the single ingredient that separated one Founder from another. When I was young, I assumed the reason I saw those pudgy old men on the cover of Forbes magazine was that they represented the most ambitious of us. And some of that was indeed true.

But what I'd come to learn later, having met with countless ambitious Founders, is that they are all ambitious. The difference is the set of conditions that unfold. For example, I've started 8 companies with 8 different outcomes. I'm still the same ambitious guy — but my outcomes change with the conditions of each business.

Sometimes we're fortunate enough that our conditions meet our ambitions in such a way that we create exponential outcomes. It's not "luck" — that's what Powerball winners had. But we have to recognize that the probability of those conditions, at the highest levels, are rarely repeatable, and to some degree damn near impossible to guarantee. Jeffrey Katzenberg and Meg Whitman are freakishly ambitious — but they can't "ambition" a company like Quibi into a guaranteed success.

Ambition comes at a Cost

What I also didn't understand when I was younger was the cost of ambition. To the outsider, ambitious people are just like everyone else, they just have more "drive". But for those of us who actually fall into the ambitious category, we are well-steeped in the enormous cost of ambition. I'm talking about the cost of time, our relationships, insane stress, and invariably - our health. Ambition at its highest levels involves the most intense form of self-masochism, which very few people are willing to endure.

At some point, when we've paid the bill of ambition enough times, in the form of estranged children, painful divorces, bankruptcies, and that one trip to the ICU — we start to realize there's a limit to how much we're willing to pay.

And that's when our limits start to kick in. We realize that there are sacrifices that we're either unwilling to make or costs we're unwilling to pay to have whatever our most ambitious selves might otherwise attain. It's not necessarily our ambition that limits us, it's our recognition of that cost.

The ROI of "More Sacrifice"

Along the way, we also start to realize that not only is the cost more than we may be able to bear, but the return on our investment just isn't there. Once you've bought one dream home, is it really worth beating yourself to death to get another? There is a point at which we realize that the incremental benefit of having that next thing isn't worth any level of cost to get it.

And that's where things get sticky. Are we shorting ourselves or being less ambitious by simply not being willing to risk more, especially if that outcome doesn't really help us? We're dancing on the line between ego and reason.

So when we passed Elon's magnificent pile of dirt and timber, what I was saying to my wife wasn't "I don't want that" — it looked pretty awesome — I was saying, "I can't have that because I'm not willing to sacrifice more to get it, and I can't guarantee the conditions it would take to have it."

And I'm OK with that.

In Case You Missed It

I’m Killing Myself. How Is Everyone Else Finding Work/Life Balance? Work/Life balance isn't about working less, it's about adjusting our approach to work.

Is Doing Non-Startup Stuff Good For My Startup? (podcast). Join Wil and Ryan as they discuss how doing stuff that's NOT Startup related is important not only for your own sanity, but for the growth of your company.

I’m Burnt Out. What Do I Do? When we hit a point of burn out it's important that we understand what to do about it. If we ignore it, the problem only gets much worse. So let's take a look at what Founders do to deal with burnout head-on.