When Your Career — or Who You’re Known For — No Longer Fits
The Podcast Episode That Started With a Stranger in the Woods
A month ago, I met Bob Mathers in the woods.
We were at a Retreat, surrounded by tall trees, cold air, and that kind of peace and collective honesty that only happens when the usual noise falls away (literally, there was no cell service in sight) with a group of people who led with vulnerability and truth - it was disarming and comforting on so many levels.
I was truly blown away by how much I needed it, and how special the entire experience was. My next post will be all about that Retreat but for right now, I want to talk to you about Bob.
Bob was the keynote speaker that weekend — and his talk cracked our entire group wide open in the best possible way.
One minute we were crying, the next we were laughing, and by the end we were all sitting there feeling seen, inspired, and deeply connected.
It felt less like a keynote and more like being reminded of how important life, creativity, curiosity and not wasting our precious time here on earth is.
I went into that retreat experience secretly holding and tending to a lot of grief inside myself, and his talk spoke right to that part of me. I went right up to him after and said how important it was - he said he clocked the tears and felt the connection too.
Later that night, Bob pulled out a guitar at the campfire and brought a circle of strangers together by leading us through a full Tragically Hip sing-along under the stars.
It was surreal, grounding — a “this is what community feels like” moment.
We didn’t speak much more at the retreat, but I gifted everyone a copy of my book - and he happened to grab one, and later asked me to be on his podcast to speak about it, neither of us expected for the conversation to be as deeply meaningful and fun as it was, but damn I am grateful the universe brought us together to have it.
And now I am so pleased to share it with you…
We talked about the hard, human parts of reinvention:
burnout
career transitions
identity shifts
the fear of what comes next
shedding old versions of ourselves
navigating the messy middle between chapters
rebuilding clarity and direction when nothing feels certain
So, if you’re in a “what now?” season of life or work, this conversation will meet you exactly where you are — with honesty, reflection, and the reminder that you’re not moving through it alone.
You can listen to the episode everywhere you can listen to your podcasts - and I know we would both so appreciate you letting us know what you think.
And if you aren’t already following Bob’s podcast and Substack, please do :)
Trust me
He’s someone worth listening to.
And someone I am grateful to now call a friend.
Just a reminder to all my local friends, I am hosting an in person event this Sunday in Conestogo, Ontario Canada - where we can come together inside community to celebrate and honour this exact thing - moving through big change and being in between worlds, lives, roles or careers. I’m so excited at the 20 people on guest list so far - it’s going to be a really special night and if this is something that is calling to you, I’d be delighted to see you there.
PLUS - our friend Bob will be there - so you can meet him in person!