What Entrepreneurs Can Learn from Passages in Caregiving
Priya spent her first eighteen months building a lending app the way most early-stage founders do: sleeping under her desk twice a week, answering every support ticket herself, treating each investor call like an emergency. When the company raised its Series B and grew from nine people to eighty, she kept the same playbook, signing off on every hire and reading every complaint personally, certain the intensity that got her here would keep the company alive. Six months into the new stage, her best engineers were quitting and her co-founder had stopped bringing her problems, and she still didn't understand why. She had never asked what a company this size actually needed from its founder, only kept doing what once worked, waiting for the exhaustion to end.
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
Naming which stage the company is actually in
The habits that carry a founder through the earliest scrappy months are not the habits a fifty-person company needs from its leader. Each stage asks something different: hands-on building, then delegation, then governance, then eventually loosening daily control. Naming the stage honestly, rather than assuming yesterday's intensity still fits, is the first real act of leadership maturity, and it must be redone deliberately, since no one else will do it for you.
A founder keeps micromanaging through a growth stage that actually requires hiring real leaders and stepping back, and burns out the very team that could have carried the company forward.
Once a quarter, write one sentence naming what stage the company is actually in right now, separate from what stage you wish it were in.
Matching the help you seek to where the company stands
A pre-seed founder needs blunt feedback on the idea itself. A scaling founder needs help with people systems and delegation. A founder nearing an exit needs different counsel, often about letting go of control gracefully. Seeking the same peer group or advisor for every stage means getting advice calibrated to a company that no longer exists.
A founder leans on the same seed-stage mentor for a Series C decision and gets scrappy, informal advice where the situation actually calls for structured governance.
Before your next hard decision, ask whether the person you are about to call has actually led a company through the stage you are in now.
Preparing for the stage after this one
It is tempting to assume the current growth curve or team structure will simply continue. Companies that survive multiple stages tend to have founders who quietly rehearse the next transition before the moment demands it. Preparing honestly for a harder stage ahead is not pessimism; it is what keeps a transition from becoming a crisis that catches the whole team off guard.
A founder refuses to plan for a leadership transition or downturn until revenue actually drops, leaving no real time to prepare the team.
Name out loud, to one trusted person, the single stage transition you are most avoiding thinking about right now.
Meaning built along the way, not only at exit
It is easy to tell yourself that years of hard building will be justified only by a successful sale or a clean exit. But most of what a founder actually gains, judgment, relationships, resilience, is built during the ordinary, difficult middle stretch, not delivered all at once at the end. Treating the outcome as the only thing that matters means missing years of real growth that were happening the whole time.
Preparing honestly for a harder stage ahead can feel disloyal to the optimism a team needs to stay motivated. The resolution is not to hide the preparation but to separate its audience: keep confidence visible in daily execution, while doing honest stage-planning quietly with a smaller circle of advisors or your board, so foresight and morale can both be true at once.
Name one thing, honestly
What would change about how you are leading today if you assumed, honestly, that this stage of the company will not last?
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 out loud, to one trusted person, the single stage transition you are most avoiding thinking about right now.