Instead of assuming that we’ll always have the things we have right now, what would happen if we assume that things won’t continue as they are?
Here’s my guess: Rather than cling to the stuff that won’t necessarily serve us in the long term — as we so often do! — we could instead clear space to optimize for what could happen.
Read on to see what I mean.
Recently I interviewed Kyle Hanslovan, the CEO of Huntress, who takes the time each year to ask himself a very important question: Am I still the best person to be CEO?
He asks this seriously, and entertains the possibility that the answer is no. Once he’s decided the answer (and spoiler alert: so far it’s been yes), he then presents his case to the entire company.
This year, Kyle’s company note was called, “The end of the line for this CEO” — a solid bit of internal clickbait. As it turns out, he was not stepping down. Instead, he wanted to make clear that “the version of the Series A CEO is gone.” His company had grown and would never need that version of leadership from him again — so to steer Huntress into the future, Kyle would need to become a new kind of leader.
Still, he says, one day the answer truly might be no: The company may grow in a way that he’s no longer best suited to lead. And that would be fine, he says. “I’m not dead set on being the CEO forever,” he says, “but I am dead set on our success.”
I’ve interviewed several executives who’ve gone through a similar process: For one reason or another, they were confronted with the question of their own limitations — and the impermanence of their positions. And by the end of it, they were grateful.
Netflix cofounder Marc Randolph was one of them. He was the company’s first CEO — until one day, when his cofounder Reed Hastings proposed that Marc step aside and Reed take over.
“I’d had a fair amount of success in my career, and I had a reasonably mature view of my real strengths and weaknesses,” Marc told me in a podcast interview. Upon reflection, he realized that Reed was right: Marc’s strengths were in bringing a vision into existence, but he was not the kind of leader that scaled a company exponentially. He had served his purpose at Netflix, and the company now required a different leader’s skillset.
“The dream I had of myself as the CEO of a successful company now might have to be split into two dreams,” he said. “I was going to have to choose which one was more important — the me-as-CEO part, or the big-successful-company part.”
It was a hard realization, but once he made it, he says he was so much happier — because he came to understand what he was genuinely good at, and how to maximize his value to the world. “It began to dawn on me that what I truly loved was the early stages. It’s what I’m actually good at!” Now he spends his days helping other early-stage entrepreneurs turn their dreams into realities, mostly as a CEO coach or a mentor.
Mailchimp co-founder and CEO Ben Chestnut faced a similar moment, though the outcome was different.
He started Mailchimp as a small, scrappy company — and he considered himself to be a small, scrappy CEO. He liked keeping things fun and unstructured. But as his company grew bigger, he didn’t adapt. His old employees understood him, but hundreds of his new hires were skeptical and frustrated. They wanted structure and planning, and all they saw was a leader with no articulated vision.
Eventually, after a particularly tense all-hands meeting, Chestnut realized that something had to change: Mailchimp either needed a new leader, or he needed to become a new kind of leader. He decided to, as he told me, go from “startup to grown-up.”
“I got through it after many months of lots of pain and suffering,” he told me. “And then it was a few more months of pain and suffering.” But he did it: He refined his company’s mission and hired a layer of middle management to spread it. Many early employees left, but Mailchimp went on to thrive. And in September of this year, it sold to Intuit for $12 billion.
In all these cases, leaders took a cold look at themselves and determined who they were — and what needed to change as a result.
Were they the right fit for what their company needed next? Marc decided no. Ben decided yes. Kyle is deciding anew every year. And here's the thing: They’re all correct. There is not one model of what we can be, or what we must become. There is simply a question of what is needed, and what the opportunity is, and whether we are interested in pursuing that opportunity… or another opportunity.
I would be remiss not to mention the very important emotional component here too. When we approach life with the assumption that we won’t always have what we already have, it puts us in a position to choose our path, rather than just passively following a path that’s laid out for us.
And when we’re active participants in our lives and careers, we get to feel a sense of ownership over the things that happen to us. If you assume you’ll always have your role, and then the position is removed from you, it feels like a loss. But if you make the choice that the job isn’t a fit for you, then moving on isn’t a loss at all.
It’s just the natural next step.
OK, this isn’t about puppies. But it’s about the news version of puppies.
If you’re struggling with doom-scrolling, then I cannot more strongly recommend a weekly newsletter from the Progress Network called What Could Go Right?. It covers the work being done to solve the world's most intractable problems and collects global progress on everything from climate change to human rights, and will make you feel better about the world. Subscribe here, and start happy-scrolling instead.