Paint The Cave

A cave can be a refuge or a fearful passage. Bring your own paint!

I just learned that today, January 19, 2026, is ‘Blue Monday,’ aka the most depressing day of the year. Upon further research it seems this was a marketing gimmick made up by a travel company a couple of decades ago in an attempt to sell travel packages to warm and sunny climes. Whatever its origin, it does seem to have some merit, at least as far as conversations with my coaching clients are going these days.

One turned down an invitation to join a Sidecar Rally group because she is going through a ‘dark night of the soul,’ and feels she needs to conserve her limited energy for only the most pressing priorities. Another describes a lack of interest in activities that typically have most engaged her. It doesn’t help that she’s in the northern climes of Denmark, where days are short and the outside temperature regularly dips to many degrees below frigid. Still another knows that she ought to be out there actively looking for a new job opportunity, as her contract is up at the end of the year. And yet, she just can’t muster the ‘give a damn’ to put herself forth, describing a feeling a numbness and malaise. And then there’s the client who is recovering from a traumatic leadership situation, currently back in the classroom as a teacher and loving it. She knows in her bones she’s a leader, and that her path will take her back that direction, but right now she’s taking time to remind herself why she got into education in the first place (it’s the kids!) while letting the seeds of her next leadership venture germinate.

There are any number of reasons why school leaders – or any of us - are hunkering down these days. Constant shock from news headlines. Deep fatigue from the ‘always on’ culture of international schools. Confusion over AI and its implications. Frigid temps and nasty floods that keep the spectre of climate change front and center. It’s enough to make anyone seek a cave – a place to hide out and bide time until our nervous systems regulate and the world around us stops swirling so much.   

Other times, the cave finds us, particularly at times in our life when transformation looms, spurred by a loss, an ending, a period of profound doubt, or the stirring of a new calling. There it is: large and dark, looming in front of us. We’re frightened by what may be there, though know we must enter to get where we’re going. This type of cave is not a temporary refuge but a passage whose length is unclear. It is a cave that asks us to stare what challenges us in the face, to dwell with it uncomfortably. Maybe it’s a realization that your career isn’t bringing you the satisfaction it once did, a relationship is no longer nourishing you, you haven’t looked hard at your financial situation for fear of what you might find, that alternative life that has been whispering to you is now starting to shout. We can avoid the cave for a while, but ultimately we have little choice but to enter. Almost always, the deep discomfort of the cave experience yields tremendous rewards: a shift to a more meaningful career, prioritizing self-growth over relationships that deplete, financial awareness that leads to positive action, a new path in life that nourishes the soul. As Joseph Campbell wrote: “The cave you fear to enter holds the treasure you seek.”

I recall a conversation I had with a coaching client a couple of years ago, in which it became clear she was in a cave of the transformation, not refuge, type; e.g. not of her own choosing. One of her biggest frustrations was the lack of agency she felt in that cave. She couldn’t see its full contours and had no idea how long she might be there. As we were talking she came up with a genius idea. At least she had some control over her cave’s interior. She could ‘paint her cave!’  That might mean: engaging in activities that brought her joy; indulging her senses with beautiful objects, scents and sounds; reflecting and writing; completing tasks that were on the perennial to-do list; re-watching every episode of Friends; simply taking time to appreciate the present moment.

So for those of you for whom Blue Monday feels oh-so-real, and for whom a cave experience may be a refuge or a looming threat, take a piece of inspiration from my client with the genius idea: remember that you can add features to your cave that will enhance your experience there, whether you are simply ‘wintering’ or whether you are transforming to a new version of yourself.

Also know that my sidecar pulls up to caves as well.

For those of you whose cave involves wondering what might be out there for them that they can’t quite envision, let alone move toward ...

Sidecar Explore was created for just that reason. The 10-week program brings together a small group of explorers, each on her own adventure, to support one another as they envision and then begin taking steps toward new horizons, with individual and group guidance from moi. Register here by Feb. 2. We’ll aim to get going by end of February.

And on that Blue Monday idea, the one where a travel company used that to advertise warmer, sunnier climes, here’s a shameless plug for something to lift your spirits in April:

Regenerative Leadership: A Sidecar Summit in Spain – come join us in the beautiful, regenerative Muga Valley in Catalunya to discuss how we can lead in a way that restores rather than depletes, starting with ourselves. Dates: April 16-19, 2026. 4 spots left as of this writing. Register here.

Yours in facing down Blue Monday by bringing our own paint,

Bridget