Stay Fierce. Stay Sane.
5 habits of mind for the founder who has to do both.
My Take:
Every company buildout, and probably every worthwhile undertaking, is marked by flashes of elation and transcendence followed by long periods of total despair. I’ve been thinking about the best way to manage my own psychology, and the psychology of the teams I help lead, particularly when we’re going through the latter.
Particularly after last week’s post. 👇👇👇
I got a lot of DMs that had nothing to do with the seven lessons for being early and focused on the psychology of not winning.
The gist: yeah, sure, protect your psychology, but how do you actually f*^&ing do that? Fair. Here is my answer. Or, at least, the start of one.
1. Is it really that bad, or are you just being an asshole?
Don’t fall prey to the Founder narcissism that amplifies every win into the slaying of a dragon, and that exaggerates the hard moments into heroic struggles against darkness and evil. It’s good that you give a shit; in fact it’s necessary that you do. I love a trench warfare metaphor as much as the next guy, but at the end of the day, you’re not in the trenches. The trap is that your stakes feel world-ending when they aren’t. You’re building software, not fighting in Ukraine. You’re running a board meeting, not a field hospital in Khartoum. The stakes are real. They’re not that kind of real. No one needs to care about your precisely imagined architecture of martyrdom: gargoyles made of night sweat, moldings made of insult and injury, support beams made of I-can’t-go-on-I-must-go-on. Get over yourself. You’ve got beans on the table, a roof over your head, and you’re building something cool. On balance, you’ve got it pretty good. Remember that.
2. Find joy.
If you’re angry all the time, you’re hurting yourself. You’re hurting your team. And the more you enrage, the more you enclose. This can’t just be your cross to bear; if it’s making you miserable, it’s not good for anyone, least of all you. Find moments of pleasure and nourishment in the small stuff. A puzzle cracked. A conversation with a customer where something that was murky suddenly becomes clear. A moment of superb collaboration, or even just belly laughs with a coworker. There are nice, hard-working people alongside you putting their backs into the same thing you care about. All of these are opportunities for joy. Seize them.
3. Tune out the neener-neeners, but don’t be a sociopath.
Keep listening. See things as they are, not as you would like them to be. You’ve got to strike an elusive balance between humility and fierce conviction. The people in your corner who genuinely care about you might not always wrap their messages in the nicest gift paper, but ya gotta keep listening both to them, and to your own gut. And then figure out what you’re gonna do based on reasons, interests, principles, and occasionally intuition. If you’re listening too closely to all the people who tell you you’re hosed, and that all is lost, well, they’re probably right. But you already knew the whole thing is impossible, right?
4. Take care of yourself.
Are you on the right-hand side of your stress-performance parabola? If so, you’re thrashing, and you need to chill out. But chilling out is harder than it sounds. Figuring out what actually soothes you is hard, lifelong work. And no one’s on the hook to do it but you. You can’t just wait around for somebody or something to come in and do the soothing on your behalf.
For me right now, it’s ocean swims. It’s sitting at the foot of a bishop pine up on Mount Tam, trying to take a few even breaths. For you it might be a workout, a long walk, an instrument, a movie, time with your kids. Whatever it is, go find it. And when you find it, go to it.
And don’t mistake this for indulgence, or for something you do once the real work is done. This is part of the work. It may even be the part of the work that best enables everything else.
5. Don’t stop believing.
After giving a mealy-mouthed presentation with far too many qualifiers, my dissertation advisor gave me the following feedback: “If you don’t believe this shit, why would anyone else?” I’ve applied it to everything I do.
Teams don’t follow waffling founders into the metaphorical battle. VCs don’t invest in hedging entrepreneurs. Customers don’t cough up cash to companies that hem and haw.
So yes. Be clear-eyed about the stakes. Find the joy. Listen hard without losing your spine. Take care of yourself. Do all of it. But when you walk into the room, show up with conviction, or don’t show up.



