What Leaders and Managers Can Learn from Wintering: The Power of Rest and Retreat in Difficult Times
Dana managed a customer support team of twelve, and after a brutal product launch, half the team seemed to be running on fumes. Two people had quietly stopped volunteering for extra shifts, and the usual banter in the team channel had gone flat. Dana's instinct was to schedule a motivational meeting and push through to the next milestone. Instead, on a whim, she picked up a book about wintering a colleague had recommended after her own hard year. Reading it on the train home, Dana realized her team was not slacking off; they were depleted after a genuinely hard stretch, and treating that as a discipline problem would only make recovery take longer.
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.
0 of 5 selected
The core lessons, applied to you
Naming a hard season for the team without assigning blame
Wintering's opening idea, that a hard season deserves naming honestly rather than hiding, applies directly to a team in a rough stretch. A manager who says plainly the quarter was genuinely difficult, without treating that as a confession of failure, gives the team permission to stop pretending. That honesty tends to surface real problems sooner than a forced pep talk could.
In cultures where any acknowledgment of difficulty gets read upward as a sign the manager cannot handle the role.
Name the hard stretch plainly in your next team meeting, in one sentence, before moving to solutions.
Letting a team withdraw from nonessential work without guilt
The book treats withdrawal from ordinary demands as active recovery, not avoidance, and a manager can protect a team from optional meetings or stretch projects during a genuinely hard season. This is not lowering standards; it is triaging so real energy goes toward what matters right now, rather than spreading thin until nothing gets done well.
When leadership above still expects the same output regardless of what the team is absorbing underneath.
Cancel or postpone one nonessential recurring meeting this month and tell the team plainly why.
Building small shared rituals into a hard season
May describes cold-climate communities that build gathering and lower expectations into their darkest months, offered as her own respectful account of specific traditions, not a checklist every team must copy. A manager can take the idea, that hard seasons are handled better together, through small rituals, a check-in, a shared meal, a standing moment to ask how people are doing.
Remote or hybrid teams where informal gathering does not happen naturally and has to be built deliberately.
Start one short weekly check-in this month focused only on how people are doing, not deliverables.
Winter as a shared metaphor, not a verdict on the team
The book uses winter and hibernation as a metaphor for hardship, not a scientific claim about why a team's energy dips at certain points in the year. Any mention connecting mood to daylight is one area of ongoing, evolving interest, not settled fact. What holds regardless of calendar is the deeper point: teams cycle through hard stretches and recover, and that cycle does not define competence.
These ideas pull against each other in management. Naming a hard season honestly can invite scrutiny from above that makes protecting the team's workload harder to justify. Building shared rituals takes time a manager already stretched thin may not have to spare. There is rarely a clean way to do all three at once; most managers end up naming the season honestly to their team while quietly absorbing some pressure from above themselves, a cost worth acknowledging.
Name one thing, honestly
- What would it look like to name a hard season to your team honestly, without treating it as failure? - Which nonessential task or meeting could you protect your team from this month? - What small ritual could help your team feel less alone in a hard stretch?
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
0 of 3 selected
Run this for seven days
Start one short weekly check-in this month focused only on how people are doing, not deliverables.