Wintering
Coaches & Mentors
DropRegion · Lessons from Wintering · Katherine May

What Coaches and Mentors Can Learn from Wintering: The Power of Rest and Retreat in Difficult Times

Simone had coached young athletes and adults through career transitions for over a decade, and she prided herself on always having something useful to offer. After a string of difficult client sessions and a personal loss she had not fully processed, she noticed herself running out of the patience she normally brought to the room. She kept scheduling sessions anyway, reasoning that her clients needed her steady presence more than she needed a break. A fellow coach, sensing something was off, recommended a book about wintering during a supervision call. Reading it that weekend, Simone recognized the exact thing she coached clients through, treating a hard season as something to move through with support, and realized she had stopped applying it to herself.

01 · The Book in One Minute

The whole book, compressed

01Naming Your Own Hard Season
02Scaling Back Client Load
03Being Supported
04Winter As Metaphor

This edition works through 4 core lessons — take them one at a time, not all at once.

02 · Where Are You Now?

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.

A coach's role is built on appearing steady and resourced, which makes admitting personal depletion feel like it undermines the relationship.
Client sessions continue on a fixed schedule regardless of what a coach is carrying that week.
Emotional labor accumulates from holding other people's hard seasons, on top of the coach's own.
Coaches often lack their own coach, since they are usually cast as the one who provides support, not receives it.
Client outcomes can feel tied to a coach's visible energy, adding pressure to perform wellness rather than rest.

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03 · Core Lessons

The core lessons, applied to you

Naming Your Own Hard Season

Naming your own hard season, not just your clients'

The idea

Wintering's central move, naming a hard season honestly rather than hiding it, applies to a coach who spends most working hours helping others do exactly that. Telling a supervisor or trusted peer that this has been a genuinely hard season is not a failure of the coaching persona; it is the honesty a coach would encourage in any client.

What it looks like

When a coach's business model depends on projecting constant calm and capacity to prospective clients.

Try this

Tell one peer coach or supervisor, plainly, that this season has been hard for you too.

Scaling Back Client Load

Scaling back client load without treating it as abandonment

The idea

The book treats withdrawing energy from ordinary demands as active recovery, not neglect, which a coach can apply by reducing caseload or pausing new intake during a genuinely hard personal season. This protects the quality of attention existing clients receive, rather than spreading a depleted coach thin until the work quietly suffers for everyone.

What it looks like

When income depends directly on caseload, making any reduction feel financially risky no matter how depleted a coach feels.

Try this

Pause new client intake for a defined short period this month, even briefly.

Being Supported

Being supported, not just the one who supports

The idea

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 script every practice must adopt. A coach can take the idea that hard seasons go better shared, seeking supervision or peer consultation rather than assuming the role only runs one direction.

What it looks like

Peer consultation groups can be scarce or expensive, especially for independent coaches without an institutional home.

Try this

Book one supervision or peer consultation session this month specifically for yourself.

Winter As Metaphor

Winter as metaphor, not a mark against your practice

The idea

The book leans on winter and hibernation as a metaphor for hardship, not a scientific claim about why energy dips at particular times of year. Any mention connecting mood to daylight is one area of ongoing, evolving interest, not settled fact. What holds regardless of the calendar is the point underneath: a hard season passes, and does not define a coach's actual skill.

When the clusters compete

These ideas pull against each other in a real coaching practice. Naming a hard season honestly can feel risky when the business depends on projecting steadiness, making scaling back feel doubly exposing. Seeking supervision takes time and money a coach already stretched thin may not have to spare. Most coaches manage a partial version of each, honest with one trusted peer, reducing load where they can, while still showing up for clients whose sessions cannot be paused.

04 · Choose Your Priority

Name one thing, honestly

- What would it look like to name your own hard season to a peer, the way you would encourage a client to? - Where could you scale back your caseload this month without treating it as abandoning your clients? - Who supports you, and when did you last actually let them?


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.

05 · Put It Into Practice

The practices from this edition

Tell one peer coach or supervisor, plainly, that this season has been hard for you too.
Pause new client intake for a defined short period this month, even briefly.
Book one supervision or peer consultation session this month specifically for yourself.

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06 · Small Experiment

Run this for seven days

Book one supervision or peer consultation session this month specifically for yourself.

07 · Remember This
If you remember only 4 things
01Naming Your Own Hard Season. Wintering's central move, naming a hard season honestly rather than hiding it, applies to a coach who spends most working hours helping others do exactly that.
02Scaling Back Client Load. The book treats withdrawing energy from ordinary demands as active recovery, not neglect, which a coach can apply by reducing caseload or pausing new intake during a genuinely hard personal season.
03Being Supported. 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 script every practice must adopt.
04Winter As Metaphor. The book leans on winter and hibernation as a metaphor for hardship, not a scientific claim about why energy dips at particular times of year.
08 · Your Next Step

What will you do differently because you read this?

Wintering: The Power of Rest and Retreat in Difficult Times, by Katherine May, was written for an adult moving through personal loss, illness, or transition, not specifically for a coach supporting others through their own hard seasons. Read through that lens, its gift is a reminder that the person who holds space for others also needs a season to be held. If your own winter feels prolonged, severe, or carries real hopelessness, that is worth bringing to a doctor or therapist, since it can overlap with something coaching skill alone cannot fix.