Everything is easy
Many years ago, Daniel Chait, the founding CEO of Greenhouse, tweeted something I never forgot:
Everyone else's business looks easy from the outside.
At the time I saw the tweet, I was literally thinking, "Damn, we really should have started an ATS company, that seems way easier than what we're doing!" You could not script better irony.
I've thought about his comment many times in the years since. It is a simple and elegant truth: everyone else's business does look easy from the outside, especially if it is successful.
But I've worked with enough founders and executives to know that the appearance of ease is always, 100% of the time, a lie.
Optimizing for greatness also means being terrible
Companies can struggle in so many ways. Maybe you have awesome teammates and you're paid well, but your product is bad. Maybe you have a great product, but you can't reach customers. Or perhaps your business is growing fast, but everyone on your team is miserable.
There's a lot of advice about leading with values and choosing what to optimize for. However, in optimizing for one thing, you inherently trade off something else.
For instance, I regularly meet with leaders who have a strong POV on whether their workplace should be in-person or remote. In-person leaders cite the benefits of co-location: better collaboration and connection, more productive disagreement, and ability to move faster. However, those same leaders often complain about how expensive it is to hire people in dense talent centers like San Francisco, Seattle, or New York.
On the other hand, leaders who believe in remote work prioritize hiring a broader range of talent, often for a fraction of the cost they might pay in urban hubs. They value flexibility and would rather their team spend more time working and less time commuting. But those same leaders lament how hard it is to create a sense of identity and connection when people don't see each other day to day.
Like most religious debates, there's no right answer here. It's all about what you're willing to trade off.
Let's talk about the tradeoffs
The RTO topic has gotten a lot of play, but as a rule, we don't think enough about the tradeoffs when we're considering what to optimize. This is as true for individuals as it is for businesses. Like:
- Want career stability? Work at one company for 25 years and become incapable of getting hired anywhere else.
- Want autonomy? Drop your W-2 lifestyle and become permanently anxious about money.
- Want relevance in AI? Build your fleet of superagents and become incapable of unplugging.
- Want to be “mission driven”? Merge your entire personality with your employer and experience every reorg as a breakup.
- Want to be indispensable? Become the only person who knows how anything works and spend every vacation secretly checking Slack from the bathroom.
If you're committed, optimizing for one thing always means compromising on something else. This is why it's hard to choose a truly optimal path; tradeoffs can be hard to accept.
On the other hand, businesses that look easy from the outside have chosen to optimize for something. If the team is strong at execution, they often succeed in their goal. But it isn't easy. Tradeoffs never are.
To look like a duck gliding gracefully across the water, underneath the surface you've got to paddle like hell.
Choose your own dysfunction
Sometimes it's clear what you want to optimize for. But in the majority of cases big and small, the right answer isn't obvious. Stick with the job you like ok, or take a risk on the job you might love? Finish your current project, or flake out and jump on a time-sensitive opportunity? Get a good night's sleep, or stay up late watching the Summer House reunion? (Hey, I didn't say that all choices have merit.)
In the end, choices are just about tradeoffs. Optimizing in one area creates dysfunction in others. And optimizing to not make choices at all just creates another kind of dysfunction.
The bottom line: Maturity is less about solving dysfunction than intentionally choosing which dysfunctions you can live with. Goes double for mature leadership.
Kieran
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