How many Super Bowls is enough?

How many Super Bowls is enough?

Tom Brady is the G.O.A.T. Yes, despite falling one drive short of their sixth Super Bowl, it’s hard to throw shade at Brady and the Patriots. Who wouldn’t want to be the handsome underdog turned future hall-of-famer, a savage competitor with ice in his veins, performing at his peak at age 40, and, let’s not forget, Gisele’s arm candy. (But what’s up with not eating strawberries?) You’d have to be nuts to not to want aspire to be Brady or the Patriots.

Enter the shade, delivered via defensive end Lane Johnson from the Super Bowl champion Eagles. He criticized the Patriots’ “culture of fear” adding: “You only get to do this job one time, so let’s have fun while we’re doing it. Not to be reckless, but I’d much rather have fun and win a Super Bowl than be miserable and win five Super Bowls.”

Most of us would call BS on that statement. After all, five is greater than one. Excellence at all costs is what we strive for. And fun? Save the strawberry daiquiris for retirement, once the trophy case is complete. These are just the words of a newly victorious and braggart lineman – not worth deeper consideration, right?

But we often face a variant of this dilemma in our everyday lives. Do we take the job with more pay and put up with brutal hours? Do we start a lifestyle business or venture-backed start up? How do we reconcile delayed gratification versus living in the present?

When I left the corporate world, I was very fixated on starting a high growth, venture-backed company. I wanted to prove that I could do difficult things. I wanted to make a lot of money. No joke, I wanted to be featured in the X under 40 lists. Behind closed doors, I was (arrogantly) dismissive of the high-growth company’s lowly opposite, the lifestyle businessThis type of venture, optimizes for quality of life and flexibility as opposed to outsized wealth and prestige. This was my own one versus five Super Bowl moment – messily capturing my usual angst around achievement, financial security, identity, and freedom. Three years into my entrepreneurial journey, I can comfortably say today that a lifestyle business is much better suited to, well, my lifestyle.

I need to be emphatically clear that this isn’t a knock on Tom Brady, the Patriots, ambition, excellence, or even doing things for money. I am in awe of what Tom Brady has done in his career – there are parts that I’ve tried to emulate, and others I’ve abandoned (seriously, dude – the strawberries).

On the contrary, it’s an invitation. An invitation to examine the motivations behind winning your own Super Bowls and discerning both the benefits and trade-offs that come with that journey. And noting that these trade-offs evolve with time and life circumstance. I know that for me, they’re completely different when you’re young and single, raising two young kids, and (presumably) when your kids are self-sufficient.

If you want to add a bit of spiritual joo joo to this football-heavy conversation, there’s the trade-off between the journey and the destination. This doesn’t mean we should drop everything and live in the moment. On the contrary, Zen Hospice Project founder Frank Ostaseski encourages us to invest in the people we love yet to have a plan, hold it lightly. Robert Hastings’ poem The Station captures this tension beautifully:

“Yes, when we reach the Station, that will be it!” we promise ourselves. “When we’re eighteen. . . win that promotion. . . put the last kid through college. . . buy that 450SL Mercedes-Benz. . . have a nest egg for retirement!” From that day on we will all live happily ever after.

Sooner or later, however, we must realize there is no Station in this life, no one earthly place to arrive at once and for all. The journey is the joy. The Station is an illusion–it constantly outdistances us.

I recently spoke to a talented and ascending venture capitalist in San Francisco about this. He is in a dream role, but the hours, travel, and emotional commitment are demanding – approaching burnout levels.  Married, but pre-kids, he wondered aloud how he could sustain this pace once they had kids. He told me, “Right now, I think I want to win more than one Super Bowl. Maybe two, but that’s it.”