What Entrepreneurs Can Learn from Wintering: The Power of Rest and Retreat in Difficult Times
Mara had run her small packaging design studio for four years, and this winter, business slowed right along with the season. Two clients paused their contracts, her lead designer moved away, and Mara found herself refreshing spreadsheets past midnight, repeating that a real founder pushes through no matter what. She kept booking calls she had no energy for, afraid that admitting exhaustion would look like proof the business itself was failing. One snowed-in night, with tea and nothing left to prove, she picked up a book a friend had left on her counter, about treating hard seasons as something to move through deliberately rather than outrun. She recognized herself immediately: not broken, just in a fallow stretch that most founders eventually meet, whether or not they say so out loud.
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 the slow season without treating it as a verdict
For a founder, the instinct is to treat any slowdown as proof the business, or the founder, is failing. Naming a hard season honestly, rather than concealing it, matters because hiding a rough stretch tends to produce worse decisions under strain. Calling a slow quarter a real season, not a verdict, opens room for clearer choices.
When investors expect a confident growth story every quarter, naming a slow season honestly can feel like it risks funding.
Say the slow season out loud, in one sentence, to a trusted advisor before your next update.
Treating withdrawal as strategy, not surrender
Wintering argues that pulling back energy from ordinary demands during a hard season is active recovery, not laziness. Skipping a nonessential meeting or delegating a task that does not need founder attention is not quitting on the business. It is redirecting limited energy toward decisions that require judgment.
In a very early-stage company where the founder is genuinely the only person who can answer emails and run payroll.
Pick one recurring task this week that does not require your judgment, and hand it off.
Borrowing from communities that plan for hard seasons
May describes cold-climate communities that build gathering, shared food, and lower expectations into their darkest months, offered not as a rulebook but as her own respectful account of practices she encountered. A founder can take the idea, that hard seasons go better shared than hidden, without importing any one tradition wholesale.
Founder peer groups can themselves become a stage for performance, where everyone insists their numbers are fine.
Tell one peer or mentor that this quarter is genuinely hard, before your next catch-up.
Winter as metaphor, not a diagnosis for the business
The book leans on the literal season and hibernation as a metaphor for hardship, not a scientific claim about why founders feel depleted at certain times of year. Any mention of mood or energy tracking daylight is one area of ongoing, evolving interest, not settled fact. What holds regardless of season is the point underneath: a business can move through a hard stretch without that stretch defining its worth.
These ideas pull against each other inside a real business. Naming a slow season honestly can invite scrutiny that makes withdrawal feel unsafe, since investors might read candor as a cue to disengage. Leaning on a founder community takes time and vulnerability someone in a hard season may not feel they can spare. Most founders manage a partial version of each idea at once, honest with a few people while protecting a handful of hours, still showing up enough to keep things running.
Name one thing, honestly
- What would it look like to name this season honestly to one person you trust? - Which recurring task could you hand off this month to protect your capacity? - Who in your peer network might be having a harder quarter than they let on?
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
Tell one peer or mentor that this quarter is genuinely hard, before your next catch-up.