When Guilt Kept Me Quiet

A single choice to stay quiet can feel like self-protection…until it builds a wall you never meant to raise.

In this episode, I share a story about leaving a role I loved and telling a boss, who was also a friend, far too late. The career move was right. The offer made sense. But the harder lesson lived in what I didn’t say soon enough, and how that silence reshaped a relationship I cared about.

We’ll explore why “just what the contract requires” isn’t the whole picture when trust is involved, and how guilt and timing can quietly turn into distance. I reflect on the look that said, “I would have helped you,” and the irony that the support I needed was already there, but my own fear kept me from asking.

If you’ve ever replayed the conversation you didn’t have soon enough, this one will sit with you. Off My Chest is a space to let awkward, unfinished talks breathe—because once we name them, they start to loosen their grip.

Off My Chest is created and hosted by Anitra St. Hilaire. If you'd like to hear more from me, sign up for my newsletter, Mirror Truth.

Episode Transcript

SPEAKER_00 (00:02):
I still think about a silence I chose many years
ago.
Not in a meeting, not even anargument, but the moment I told
my boss, who was also a goodfriend of mine, that I was
leaving the organization.
By then I had already wrestledwith it for weeks.
I had an offer in hand.

(00:23):
I knew it was the right nextmove for me, and yet I hadn't
said one word to her.
We had worked side by sidethrough really late nights, some
really significant projects, andthrough a lot of constant
change.
I know she trusted me.
I certainly trusted her.
And still I kept quiet.

(00:43):
And when I finally spoke, it wasjust when I had to give two
weeks' notice.
And the look on her face told meeverything.
It wasn't anger, it wasn'tbetrayal, just disappointment.
And it was the kind ofdisappointment that said, I

(01:03):
would have helped you, I wouldhave been there for you if only
you had trusted me enough totell me sooner.
Welcome to Off My Chest.
I'm Anitra St.
Hilaire.
I have spent my career leadingpeople and coaching executives.
And if there's one thing I'velearned, it's this conversations
shape everything.

(01:24):
Our work, our relationships,even how we see ourselves.
But I'm not just here as a coachand a leader.
I am here as someone who stillreplays her own awkward,
painful, unfinishedconversations.
And that's what this podcast isall about.
So back to my story.
I want to be clear.
I wasn't out there job hunting.

(01:46):
I wasn't secretly scrolling jobboards late at night.
I had just randomly come acrossthis opportunity.
It was rare.
It was a perfect fit from acompany I was really excited
about.
And I knew I had to go after it.
And I've always told peoplecompanies should be prepared.

(02:09):
No one owes notice beyond what'sin their contract.
Of course, telling people you'releaving with extra time is
helpful, can be very respectful.
But at the end of the day, mycounsel is always you have to do
what's best for you.
And that's the professionalanswer.
But the personal side of me knewthis silence came at a cost, and

(02:30):
not just for the company I wasworking with, but for my boss,
who I cared about.
And I carried that guilt aboutmaking that decision much longer
than the decision itself.
Every day that passed withoutsaying something made it so much
harder to open my mouth.
And the irony of this is I knewshe would have supported me.

(02:54):
I knew she would have workedwith me through the transition.
She would have given me a greatrecommendation to the company
that I was going to look at.
That's just who she was.
And that's who we were as ateam.
That's who we were together.
But I let myself get into thisguilt spiral and I felt so
poorly and so badly.
And am I leaving this person ina bad position until it was just

(03:18):
too late?
And so when finally came down toit, and I had to tell her I was
leaving, it landed not as achoice we could have navigated
together, but really as a wallbetween us.
And, you know, my not tellingher, my silence really had
already done its damage.
And I still think about that tothis day.

(03:41):
I know leaving was the rightdecision, but not being honest
earlier, hiding behind thatguilt and letting that guilty
feeling drive that silence isreally the part of it I regret.
And, you know, silence can feellike self-protection in the
moment.

(04:02):
But afterwards, it plays in yourmind like an old record that you
don't want to hear anymore.
It's the distance that you'venow created from people who
really would have understood.
It's the distance from thesupport that was actually there
and that I knew was there, butjust couldn't bring myself to

(04:23):
ask for.
And listen, the professionallesson is easy to name.
Timing matters when you'releaving a job.
Be clear, be honest, uh, tellthe company when you need to,
not a moment before.
All of that is easy for me torattle off.
But the personal lesson, andit's really the hard one for me,

(04:46):
is that sometimes silence cancost you closeness with someone
you care about.
And the people you work witharen't necessarily one and the
same with the company you workwith.
And once that distance is there,it's really hard to bridge.
And so if I had to do it allover again, I would probably

(05:10):
tell her a little sooner.
I can't say that I would,though, because I was I was
nervous and uncomfortable andyounger and didn't have all the
confidence that I have now andreally worried about what would
happen to me.
And, you know, it's all it's alldependent on who you are in your

(05:34):
particular situation.
But I really just wanted to takea moment and reflect that this
one felt bad because I did treather not as a friend, and I knew
she was.
And not everyone you work withis your friend, but in this
case, she was mine, and I shouldhave I should have treated her
like the friend she was to me.

(05:56):
And that's what this space isfor.
It's a place to bring thosemessy conversations into the
light and see what happens whenwe stop carrying them alone.
Each week I'll share morestories, sometimes mine,
sometimes from guests that justname conversations we can't
shake.
Because once we name them, theystart to loosen their grip.

(06:18):
So thanks for listening, andthank you for letting me get
this off my chest.