On Not Settling
You may be exhausted. Now is not the time to settle. Oasis may be just over this dune.
If there’s a theme running through my sidecar coaching conversations this season, it seems to be some version of this: a refusal to settle for something that falls short of expectations, transgresses boundaries, or disappoints our grander aspirations for ourselves and our place in the world.
I’ve noticed it with leadership job seekers who get sorely tempted to accept a position that is a ‘bird in hand’: “They really want me!”/ “At least it gets me out of my current dismal situation.” “I could finally stop the search and start the transition process!” And yet ... in further conversation it’s clear that the opportunity doesn’t align with the seeker’s sense of a role in which she is truly set up to shine. So onward she goes with this too-often-demoralizing recruitment process. Which in several cases (so far) has led to that opportunity that feels like growth! Sometimes just right around the bend from that brave about-face she took from the settling path.
I’ve noticed it with leaders who are on the receiving end of harmful behavior – from supervisors/ colleagues/ parents – yet who refuse to let this diminish their dignity and their courageous willingness to self-advocate, especially when boundaries are inappropriately and purposefully crossed. (I don’t know about you but it seems that the world of international schools has its fair share of fragile-ego bullies disguised as charismatic leaders.)
I’ve noticed it with my pioneering cohort of Sidecar Explore adventurers, who are envisioning hopeful possibilities for this next stage in their lives, and are taking positive action steps to test these possibilities out – often defying internal voices cautioning against the audacity of desire.
Perhaps it is not surprising that women are embracing this ‘not settling’ given the broad backdrop against which they are leading: a world that doesn’t reward an ‘accept the status quo, follow the rules and everything will be alright’ attitude. We’re seeing clearly that being the good girl whose role it is to take care of others and not rock the boat rewards everyone except ... the good girl.
We’ve got lots of unlearning to do! It starts with getting back to self, reminding ourselves who we are at our core, that we’ve had great dreams and aspirations (and yes, desires!) for ourselves, that we know we’re competent and capable, and that we deserve opportunities that align with those dreams/ aspirations/ desires/ competencies.
Sidecar Summits are a great way to jumpstart that process. They provide prompts and space for self-reflection, deep conversations centered on themes relating to leading-while-female, purposeful and supportive connections with other courageous leaders, and an opportunity to immerse ourselves in natural surroundings, which have so much to teach us about how to lead.
Spaces are still available for these Summits:
- Portugal, November 17-21, “Love-Based Leadership.” One spot open. Let me know no later than Monday, November 3.
- Cambodia, January 22-25, 2026: “The Power of Presence.” 3 spots open as of this writing. Will close registration by November 15.
- Spain, April 16-19, 2026: “Regenerative Leadership.” Applications accepted through November 7.
If Summits don’t fit into your schedule, I am always delighted to sidle up with my sidecar for a one-on-one coaching adventure designed to keep you from settling.
On a personal note: inspired by the courage I’m witnessing from my sidecar, this refusal to settle for something that may feel ‘comfortable,’ or offer the path of least resistance, but doesn’t feel true to one’s essential sense of self and potential ... I’ve decided to call an end to my exploration of Portugal as my next nest. For all its wonders – from weather to landscape to kind people to scrumptious pastries – it doesn’t say ‘nest’ to me. I could find things to make a life here feel really worthwhile. And yet ... I don’t want to stake my claim just yet, when I feel a gap between what I believe life can feel like and what it currently does feel like. Yes, I’m tired of living out of a suitcase and moving every few weeks. No, I can’t expect to find everything on my list of wants in one place. Still, I trust myself that I will know an ‘imperfect, with room for growth and exploration’ situation from an ‘imperfect; feels like settling’ one. I’ve got ideas that I’m checking out. I’ve started online language learning again. Watch this space!
Yours in keeping the wheels turning until the groove feels right,
Bridget
