What Entrepreneurs Can Learn from It's OK That You're Not OK
Priya had raised her seed round eight months before her father died. She came back to the office on a Tuesday because an investor update was due Friday. Her co-founder rolled a whiteboard labeled "Q3 Wins" in front of her desk and said, "Whenever you're ready, we'll pick up momentum." A board member emailed: "So sorry — let us know if there's anything we can do, but also, any update on runway?" Everyone treated her grief like a delay to manage around, a temporary outage in an otherwise functioning system. No one asked what the loss felt like. They asked when she'd be back to full capacity, as if grief were a sprint that had run long.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
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The core lessons, applied to you
The Loss Isn't a Bug to Patch
Entrepreneurs are trained to treat every problem as solvable with the right process, and grief resists that training entirely. There is no root cause to fix, no sprint that closes it out, no metric confirming it's done. Treating grief like a broken feature to debug adds a second frustration on top of the loss itself. The founder isn't failing at grief; grief was never the kind of thing their usual toolkit was built for.
A founder schedules a rigid recovery plan — three days off, then full output — and feels like a failure when grief won't cooperate.
Tell one trusted colleague there is no fixed timeline, and ask them to check in without expecting a status update.
Board-Meeting Optimism
Startup culture prizes upbeat framing, so people around a grieving founder often reach for silver linings — this will make you a stronger leader, at least the company is stable. These comparisons, however well-meant, leave the founder feeling more alone, as if their pain is being weighed against a business outcome. The instinct to reframe loss as growth material skips past the person entirely.
A board member praises the founder's "resilience story" for investor updates, and the founder feels grief repackaged as a pitch asset.
When someone offers a silver lining, it is fine to say plainly, "I don't need the upside yet — I just need this acknowledged."
What Acknowledgment Looks Like at Standup
What actually helps a grieving founder is simple acknowledgment — a colleague saying "I know this is hard" without following it with advice or a task. Being seen without being managed toward a fix lowers the isolation founder life already creates. A co-founder who says "take what you need, we've got this" does more than any wellness policy.
A co-founder avoids the topic, assuming silence is respectful, which leaves the founder feeling like the loss is invisible to the team.
Name the loss once, directly and briefly — "I know you lost someone, I'm not going to pretend otherwise" — then let the founder set the next move.
Building Again While Carrying It
A founder can care about a product launch and still be grieving; the two are not evidence against each other. Expecting grief to resolve before real enthusiasm returns sets an impossible bar, and isn't how loss works alongside a demanding job. A founder who laughs at a customer win the same month they still miss someone isn't in denial — they're carrying both at once, which is what building a company while grieving looks like.
Acknowledgment and forward motion pull against each other in a company that runs on momentum. Naming the loss directly risks slowing a meeting; protecting momentum risks skipping acknowledgment altogether. The tension isn't solved by picking one lane permanently — a team can pause for thirty honest seconds and still ship the release, as long as the pause isn't treated as an exception to avoid.
Name one thing, honestly
What would it look like to acknowledge a colleague's loss directly, without also trying to manage its effect on the roadmap?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
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Run this for seven days
Name the loss once, directly and briefly — "I know you lost someone, I'm not going to pretend otherwise" — then let the founder set the next move.