Are we really ambitious?

The truth about “workaholics.”


Last December, my dad and I were driving home in Tampa, Florida. We were running quite late for dinner plans on a Saturday night (Schiff family tradition), but he made a sharp, sudden turn into a subdivision.

“Uh, Dad?” I questioned.

“Hold on, I saw a For Sale sign,” he replied. He found the house, wrote down the realtor’s name — one of literally thousands he might call for one thing or another as a loan officer — and continued home as if nothing had happened.

On a Saturday. While running late to family plans. For relatively inconsequential and not-at-all-time-sensitive information.

This was the moment that, after 22 years, I realized where I had learned my work ethic. I saw my dad work many jobs as a kid — jobs at which he excelled, jobs with which he struggled, jobs that made him happy, jobs that made him miserable, jobs that kept him on the road, and jobs that confined him to a home office. While they’ve always involved some sort of sales, the most striking consistency has been how much of himself he invests in each endeavor. Even if he couldn’t stand a customer or coworker, he still dropped everything to take their phone call when we were on the way to dim sum on Sunday afternoon. And I’ve long since lost track of how many midnight conversations have involved some form of, “Now if we can just get X% out of Y people to convert at this $, just think about how huge this could be!”

“If we can just…” was always a trivial checkbox, rather than the crux of the plan itself.

The ethos I absorbed wasn’t simply “work hard” — it was that it was always within my control to be the hardest working person in the room. If I wasn’t willing to step up, there would be someone else just a little bit smarter, willing to wake up a little bit earlier, and burn the midnight oil just a little bit longer who would be happy to take my place. To do anything less was to be ordinary, and to be ordinary was just a nicer way of saying mediocre.

Deep down, I think that’s what actually drives most of the hardest-working people in society — a desire to be extraordinary. Or, looked at another way, a fear of being average.

Fearful or not, this attitude has always drawn me to endeavors with a clear link between effort and impact, and the positive feedback loop becomes all-consuming. More than one conversation has gone like this:

“How’s it going?”
“Good — we’re releasing some really cool new features soon at Fetchnotes. We just got featured by Apple too!”
“No no, how are you doing?”
*blank stare*

By investing so much of themselves into their career pursuits, highly ambitious people tend to conflate their sense of identity and even self-worth with that of their work. That means that when work is doing well, you are doing well. When work isn’t doing well, you are not doing well. This is the curse of ambition that most people don’t fully understand, and every highly ambitious person I know has to make a conscious effort to keep this feeling at bay. It’s also to blame for a lot of strife in both romantic and platonic relationships, mine included.

That’s because “work to live” and “live to work” types truly do exist in different worlds, and the difference isn’t laziness (as I once thought it was). All it really comes down to is your intrinsic source of happiness, existential validation, and identity — for some, that aligns with what you do for work, and for others it’s what you do when you’re not working. That dichotomy colors the way you think about family, friends, down time, location, and pretty much everything else in life. But at the end of the day, all people trend toward whatever mix of activities they believe will yield the most net happiness over time.

After all, that’s all anyone really wants to achieve with their time on Earth — to be happy, and to feel like we did something worthwhile with our time here.

This realization is what taught me my most important lesson about ambition and work: the reason I’m “ambitious” isn’t because I’m harder-working or smarter than anyone else. It’s because the things that give me the greatest sense of joy, self-worth, and impact happen to align with things that I can make a living doing. It’s because I don’t think of work as “work” — I think of it as what I contribute to the world.

That’s not the result of dumb luck, because it’s still on me to create my own opportunities and grow as an individual. It’s also not devoid of serendipity, be it the socioeconomic and geographic circumstances of my birth or its timing in history. If it weren’t the case, however, I wouldn’t be the ambitious person I am — and it wouldn’t simply be laziness.

I would just be fulfilling my uniquely human quest for happiness in a different way. And there’s nothing wrong with that.