What Entrepreneurs Can Learn from On Grief and Grieving
Mara had cofounded the logistics startup with her older brother, and eight weeks after his death she still opened his side of their shared inbox out of habit. The seed round was closing in two weeks, and the lead investor wanted a call to "make sure leadership continuity wasn't a concern." She rehearsed a calm answer, then went silent when he casually used her brother's name. She apologized, rescheduled, and walked home furious at herself for not having "moved past it," then furious at an investor treating a death like a line item, then quietly relieved neither feeling had to cancel the other. She had assumed grief would resolve before the next milestone. It hadn't asked her schedule.
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 board doesn't run on stages
Founders often treat grief like a roadmap: a sequence with a start and an end date. But denial, anger, bargaining, depression, and acceptance can arrive out of order, double back, or overlap in the same week as a funding call. A founder who expects to feel "past" anger by diligence, then finds it resurfacing mid-negotiation, has not failed at grieving — they have met the nonlinear pattern the authors describe.
A founder announces "I'm through the hard part," then cancels meetings when grief resurfaces, reading to the team as unreliable rather than human.
Before a high-stakes week, tell one trusted colleague or board member that grief may resurface unpredictably, so a hard day reads as expected rather than alarming.
Why the optimistic forecast shows up first
Early on, a grieving founder might insist the loss won't change how the company runs, or quietly bargain — close this round and everything will feel normal again. This is not denial of reality; it is the mind pacing an unbearable fact so the founder can keep functioning long enough to make payroll. Treating that buffering as a flaw to fix quickly only adds shame.
A cofounder pushes a grieving partner to "get realistic" about capacity within days of a loss, mistaking a protective pause for poor judgment.
When a major decision can safely wait two weeks, let it wait, and use that window to make only the choices that truly cannot be delayed.
Anger at the cap table is still grief
Anger at an investor's timing, at a market that did not pause, or at oneself for missing a signal is not a communication problem to smooth over — it is a proportionate response to real loss layered onto real pressure. A flat, low stretch where ambition briefly disappears is not a motivation problem either. Founders pushed to "stay positive" days after a loss are being asked to skip a normal response.
An advisor frames a grieving founder's low energy as a leadership deficiency needing better habits, when it is a normal response that needs time.
Name the feeling to one person on the team plainly — "I'm angry and slower this month" — rather than translating it into a productivity problem to solve.
Running the company while carrying the loss
Acceptance for a founder does not mean the death stops mattering or the business gets easier without them. It means building work that includes the loss rather than erasing it — marking an anniversary, keeping a cofounder's name attached to a value, and still closing rounds, hiring, and shipping. The company moves forward changed, carrying the person lost rather than leaving them behind.
Pressure to look "recovered" for investors can collide with the protective function of early denial and bargaining: performing composure too soon can flatten the buffering a founder needs. There is no clean order to resolve this in — a founder may look composed in a pitch and fall apart the same afternoon, and both are consistent with how grief moves.
Name one thing, honestly
Where in your current workload are you performing "past it" for someone else's calendar rather than your own?
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 feeling to one person on the team plainly — "I'm angry and slower this month" — rather than translating it into a productivity problem to solve.