E171: Bootstrap Boogie. The Race Between Doubt and Trust

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Sometimes leadership looks like running a race you’re not sure you’re ready for.

In this episode, Cynthia shares a story from her 17k Bootstrap Boogie run — a course made of grass, beach, clay, shale, trail, and boardwalk — and every emotional terrain in between. What began as a morning of self-doubt became a powerful reminder of what happens when we trust our presence more than our pressure.

Through moments of laughter, falling, friendship, and reflection, Cynthia explores how physical challenges often mirror our inner ones: how to stay grounded when the path changes beneath you, how to lead beside others instead of ahead, and how to blaze new trails for those who’ll follow.

This isn’t just a running story. It’s a love letter to courage, community, and self-trust — and a reminder that leadership is, at its heart, love in motion.

Listen if you’ve ever doubted your strength, questioned your “yes,” or needed someone to ring the cowbell for you.

Access the Playlist (aka musical love letter) here.

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Connect with me in my favourite places, LinkedIn and Instagram and my website is: https://www.cynthiajamiesoncoach.ca/

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Make it a great week!

Cynthia Jamieson 🧡🌱

Leadership coach for high-integrity leaders who want to thrive without proving or burning out | Ex-HR Exec | ICF PCC Coach | Podcast Host | Intuitive Intelligence® Method Guide

Episode Transcript

Cynthia (00:05):
Welcome to Uncharted and Unfiltered, The Journey Back
to You.
I am Cynthia Jameson, yourhost, and this is where we break
free from the noise and divedeep into what truly matters.
You.
If you're tired of the shoulds,the expectations, and the
pressures to fit into a moldthat doesn't serve you, you're
in the right place.
This isn't a podcast about easyanswers or sugar-coated advice.

(00:29):
This is your invitation toreclaim your path, embrace the
unknown, and become the bold,unapologetic version of yourself
that's been waiting to show up.
It's time to get unfiltered.
Let's get started.
Hello, hello, friend.
It is Cynthia and welcome backto the Uncharted and Unfiltered

(00:49):
A Journey Back to You podcast.
I hope that you are having themost amazing day.
I'm going to be completelyhonest, right here, right now,
it is 10 o'clock in the morning,and I am in my recording
studio, aka my closet, and Ihaven't yet prepared for the
day.
And there's a reason for that.

(01:10):
And that brings us to today'sepisode.
So if you were listening inreal time, yesterday, which was
Saturday, November the 1st, Iran a 17-kilometer race.
And it was called BootstrapBoogie.
The name alone makes me smile.
Because honestly, what bettermetaphor for life in leadership

(01:36):
is that?
Just think about it.
And I'm going to share with youa little bit about the course.
So there was grass, there wasbeach, there was waves, there
was clay, there was shale, therewas trail, there was boardwalk,
all of it.
And every surface demandedsomething different.

(02:00):
Balance, focus, adaptability.
It was a course that was madeof everything.
And maybe that's exactly thepoint.
Now, let me go back becausewhen I woke up yesterday
morning, I was not feeling thelove.
Let me be super clear.
You know, have you ever hadthose days when you questioned

(02:21):
why you said yes to something?
I looked at my running gear andI thought to myself, what was I
thinking?
Now, by the time that I met upwith the others in the parking
lot where we had agreed to meetbefore we carpooled down, I had
worked myself into a story.
The one that whispers, youdon't have to do this.

(02:43):
You're not ready.
You could just go home.
You get to make a choice here.
But then the chatter and theenergy of the group, when I
experienced that, I realizedthat I wasn't alone.
Those who had run before thisevent were buzzing with so much

(03:06):
excitement.
You're gonna love it.
This is going to be amazing.
And those who hadn't, well,they were right there with me,
doubting life choices.
And there it was, the veryfirst lesson of the day.
When we share our fears, theylose their power.

(03:26):
Because once we started,everything shifted.
It was hard, yes, absolutely,but not in the way that I had
expected.
This wasn't just a physicalchallenge, it was an attentional
challenge.
But every surface demanded thatI be fully present with the

(03:52):
surface.
Every step was a decision.
Every breath was a reminder tostay grounded in my body, not in
my mind.
And about halfway, I think itwas about halfway, I fell.
I wasn't the first.
Um, I think three out of eightof us in our group fell.

(04:13):
It wasn't anything dramatic.
It was just a stumble, a littlescrape, and a small reminder
that distraction costs usbalance.
Now I was incredibly gratefulthat it did not trigger my
vertigo.
I was able to brush myself off.
And I thought to myself, thereis a story in this.

(04:35):
And there was.
Because leadership, likerunning, isn't about staying
upright the whole way through.
It's not.
It's about getting back up,it's about choosing your focus
over your fear, and it's aboutstaying in the race.
Now, the best part of the daywasn't the race itself.

(04:59):
It was the people, friends,their laughter filling the air,
their presence steadying youwhen your footing wobbles,
friends who remind you thatleadership isn't always about
being out in front.
Sometimes it's about runningbeside.
Sometimes it's about runningbehind.
Sometimes it's allowingyourself to catch up.

(05:22):
And as we move through thewoods, I kept thinking so much
to myself, I love these humans.
Their stories, their hugs,their energy, their enthusiasm.
And I love gifting that samepresence back to them.
The kind of presence that says,I see you, I'm with you, I'm

(05:45):
here for you.
That's what leadership reallyis: a shared rhythm of care, of
courage, and belonging, love.
Now, somewhere around kilometer15, I think it was, I just
stopped and I looked around.
I got the trees, the ocean air,the laughter, all of it echoing

(06:07):
through the trail.
And I felt this deep wave ofgratitude for being 59 years
old, for still being willing andable to blaze new trails, both
literally and generationally.
Because I wasn't just runningfor me.

(06:32):
I was running for every womanin my family who's never had the
chance to choose this kind offreedom for my children,
stepchildren, grandchildren, toshow them what's possible when

(06:54):
you stop letting the world tellyou what you can do and start
trusting yourself to decideinstead.
Now, as we neared the finishedline, I saw my husband standing
there, which was such a surpriseto me.
Cowbell in hand.
Now I gotta tell you, he lovesa good cowbell.

(07:14):
He really, really does.
And if you're ever at an eventwith him and he has the cowbell,
you might need some earplugs.
And hours had gone missing inthe move.
So he bought a new one just forthat.
And earlier that morning he hadvolunteered to help
participants park.
Now, here he was, ringing thatbell, cheering for every single

(07:37):
solitary soul that ran by him.
And his joy was echoing acrossthe finish line.
He had the privileged positionof being able to say, You're
just two minutes away.
And I thought to myself, thisis what support looks like.
And little caveat, I wasreminded of our wedding vows

(08:00):
because this is what we agreedto was to always support each
other in our growth, in ourdreams, in becoming the best
best versions of ourselves thatwas possible.
And as I stepped back mentallyand noticed that I was
surrounded by people who loveyou enough to invite you into

(08:24):
new experiences, sometimes hardones, because they see something
in you that you haven't fullyseen yet.
And that to me is a mark of agreat leader.
People who lift you into a morepowerful story of yourself and
who cheer you on when youstumble, walk, or sprint.

(08:47):
That is leadership.
That's love in motion.
And so here's my question foryou today.
Where in your life are youbeing invited into something
that feels uncertain or hard,but could actually lead you into
a fuller version of yourself?
And who's ringing the cowbellfor you, who's cheering you on

(09:10):
when you are looking for andfinding your stride?
Or maybe who needs you to ringthe bell for them?
Because leadership isn't justabout proving our strength, it's
about trusting our presence.
And every time we show upmessy, doubtful, real, we blaze

(09:33):
a new trail of what's possiblefor ourselves, for others, for
the world.
And so this morning, as Ireflected on the race, I felt so
called to create something tocapture the energy of it all,
the laughter, the courage, theconnection.
So I made a playlist.
Something I I can't re recallthe last time that I had done

(09:57):
something like that.
But it's a little musical loveletter to the incredible friends
who ran beside me and to anyonewho is out there finding their
own rhythm again.
You can find the link in theshow notes and may it lift you,
ground you, and remind you thatyou are not running alone, even

(10:19):
when you think you are.
Thank you for running this onewith me.
And until next time, staycurious, stay kind, and keep
coming home to yourself.
Make it a great week.
I hope that you're walking awayfeeling more aligned with your
true self, more confident in thechoices ahead, and ready to

(10:40):
leave the safe path behind,knowing you've got everything
you need within.
Remember, the journey to youisn't about finding one perfect
direction.
It's about trusting yourselfenough to explore all of it.
If you're ready to dive deeper,join me for the next episode
and don't forget to subscribe sothat you never miss the next
step on your path.

(11:01):
I invite you to join my mailinglist at www.cynthia
jamesoncoach.ca, where we'lldeepen our relationship and you
can claim your copy of yourinner compass, a guide to
charting your course toauthenticity.
Until next time, stayunfiltered, stay true, and most
importantly, stay you.