Hi y'all. Hope you're all hanging in there.
I recently had a CEO book time with me during my office hours. I prepared for a typical meeting, where I’m asked for help with branding, media or fundraising.
But meetings have been different lately. More often than not now, I’m sitting virtually with a founder or CEO who calls on me because of my other set of expertise. They're in wartime. They see the writing on the wall, they’re fed up, or both—and they don’t know what to do.
They assure me that they’re still out fundraising, and continuing to push forward. I know they say this because they know that’s what a good CEO is supposed to say. But I see it in their face and hear it in their voice—they want out.
In this most recent call, the CEO had originally been recruited to take over a company that had raised a few million in funding. On paper, he was beyond qualified and the opportunity originally looked fantastic. Now, he had a few months of runway left, impossible fundraising conditions, and the week before, he'd checked himself into a hospital after having a mental breakdown.
I was glad he reached out. For the first half of the meeting we walked through some logistics of various scenarios. Then, suddenly, I felt the need to suggest something:
“You can always leave.”
I felt the energy shift.
I explained that sometimes we can forget this very obvious truth. We don’t consider it as an option, in part, because we are good people, and want to see through on our commitments, and want to do right by investors and employees by resolving to stick it through to the end.
But here’s the problem. When we convince ourselves that our only option is to stay, we lose our sense of agency and personal power. Paradoxically, when we lose our agency and power, we lose our ability to be a good leader, and that decreases the likelihood of good outcomes for the company. What you think is being virtuous is not actually good for business, or anything, for that matter.
He later told me that just having someone give him permission to think about leaving—to even consider it as an option—was exactly what he needed.
I explained that any sound investors would think that it’s a sign of your experience and discernment to come forward saying “Hey, I took this offer thinking that this was something with huge potential, and now I see that I have a different situation on my hands. We have a few paths forward. Fundraising is not on the table, unless you all put the cash up yourselves. I think it’s time to discuss our options, which include me stepping aside and replacing myself as CEO, initiating an accelerated sales process, or winding the company down.” Again, experienced investors will not blink an eye at this, are prepared to take the write off, and will likely thank you for not wasting their time.
The ones that react poorly or threaten consequences are simply revealing their lack of expertise, character, or both. Stay calm, and don't let it get to you. It's your signal that it's time to go.
This doesn’t apply just to companies—this applies to any situation you may find yourself in where you no longer feel comfortable staying. It is no coincidence that some of the hardest working founders and CEOs I know were raised in oppressive environments where they were rewarded for hard work, perfection and obedience, and were constantly made to feel like they weren’t doing enough. If they are lucky, they wake up to a moment where they realize they are repeating the same patterns in adulthood, often in both their professional and personal lives.
It is a hard moment when you realize that you are here. No one has prepared you for this moment, and to even consider leaving feels impossible. Our minds can go to dark places imagining the consequences.
But here’s the thing. This isn’t about leaving, necessarily—it’s about remembering that you can. Sitting with this thought is how you begin to get your agency and power back—as a CEO, founder, or human being. This can only lead to good outcomes.
Anyway, I just thought some of you might want to hear this today. Sending love.
