I’m 55 and I Just Quit My Job. What Am I Doing?

I’m 55 years old, and after 28 years with the same company, I just quit my job.

There. I said it.

Twenty-eight years.

I have spent more than half of my adult life with the same company. I know the people. I know the systems. I know the business. I know my job.

And there is something incredibly comfortable about being good at something you’ve done for a very long time.

So naturally, I decided to blow that up.

What am I doing?

Seriously.

What. Am. I. Doing?

For years, I had imagined what it would feel like to finally say the words, “I’m leaving.”

Turns out, when the day actually came, it was a strange combination of excitement, fear, relief and holy crap, I’m really doing this.

Because this wasn’t just changing jobs.

It was walking away from something that had been part of my life for 28 years.

And no matter how ready you are for a change, that is a big door to close.

When the Safe Thing Stops Feeling Right

There was nothing impulsive about leaving.

If anything, I may have stayed longer because leaving felt so enormous.

I had built a career there. I had accumulated years of knowledge and experience. I had become the person people came to with questions. I knew how to navigate the problems, the people, the processes and the inevitable fires that needed putting out.

I was comfortable in the sense that I knew what I was doing.

But somewhere along the way, I started realizing something:

Being comfortable because you know how to survive something isn't quite the same as being fulfilled by it.

That's a hard distinction to make.

Especially when, from the outside, everything looks fine.

You have a good job. A steady paycheque. Benefits. Vacation. Seniority.

You should be grateful.

And I was.

I still am.

Those 28 years gave me an enormous amount. I learned. I grew. I worked with some wonderful people. I built a career I'm genuinely proud of.

I wouldn't have this next opportunity without everything that came before it.

But gratitude doesn't create an obligation to stay forever.

You can appreciate what something gave you and still know when it's time to move on.

Those two things can exist together.

Then Something Unexpected Happened

I wasn't standing on the edge of my bed every morning shouting, “TODAY I BEGIN MY FABULOUS NEW CAREER!”

Quite the opposite.

I had actually been thinking a lot about slowing down.

About what I wanted the next stage of my life to look like.

About working differently.

About having more freedom.

About building GEN.

About travelling.

About creating a life where work still mattered, but maybe didn't get quite so much of me.

Then a job came along.

I looked at it and essentially thought, Meh. I'll apply. I'll probably never hear from them.

Excellent career planning.

Except they called.

Then there was an interview.

Then another conversation.

Then suddenly this thing I had casually tossed into the universe became very real.

A fully remote senior role in my field. A new company. A new industry. New people. New challenges. A chance to take decades of experience and use it differently.

And eventually, an offer.

Well.

Now what?

Because dreaming about changing your life is one thing.

Being handed an actual opportunity to do it is quite another.

At that point you have to choose.

Aren't We Supposed to Have This Figured Out By Now?

When you're young, changing your life is practically encouraged.

Try things.

Move somewhere.

Change jobs.

Take chances.

Figure out who you are.

Then somewhere around middle age, the messaging seems to change.

You've built your life now.

Protect it.

Don't rock the boat.

Ride this thing into retirement.

And there is absolutely nothing wrong with that if the life you've built still fits you.

But what if it doesn't?

What if you don't want the next ten years to look exactly like the last ten?

What if the person you became along the way wants something different?

I've changed a lot in 28 years.

Of course I have.

I'm supposed to.

Maybe one of the strangest ideas we've accepted is that changing direction somehow means the direction we were travelling before was wrong.

It wasn't.

That road brought me here.

I needed everything I learned along it.

I'm just ready for a different road now.

The Scariest Part Might Be Becoming a Beginner Again

Here's the part that genuinely scares me.

I am leaving competence.

After decades in my field, I'm used to knowing things.

I'm used to being the person people come to.

I'm used to recognizing a problem because I've seen some version of it before.

Soon I'm going to sit down in my home office, turn on a computer and be the new person.

I will have to ask questions.

Probably a lot of them.

I'm going to learn new systems, new products, new processes, new people and an entirely new business.

There will undoubtedly be meetings where someone says something and I nod thoughtfully while a tiny voice inside my head says:

I have absolutely no idea what that means.

At 55.

And you know what?

I'm starting to think that might be really good for me.

When did learning new things become something we're supposed to stop doing?

When did being a beginner become embarrassing?

Maybe there is something incredibly healthy about occasionally putting ourselves in situations where we don't already know everything.

Not because it's comfortable.

It isn't.

But because it reminds us that we're still capable of growing.

Fear Has Been Very Busy

I wish I could tell you that once I accepted the job, I floated peacefully through my resignation surrounded by an aura of confidence and personal growth.

Nope.

My brain has been having an absolute field day.

What if I hate it?

What if I'm not as good as I think I am?

What if I can't learn everything quickly enough?

What if I miss my old job?

What if I regret leaving?

What if I've completely lost my mind?

And perhaps the big one:

Who starts a whole new chapter of their career at 55?

Apparently I do.

Somewhere in all of that worrying, though, another set of questions started creeping in.

What if I love it?

What if being challenged wakes up a part of me that's been running on autopilot?

What if working from home changes the rhythm of my life?

What if I have more room for travel, for GEN, for the people I love, for the ordinary little pieces of life that somehow get squeezed around work?

What if there are people I'm supposed to meet, things I'm supposed to learn and opportunities I can't even see yet?

Fear is very good at presenting its case.

Sometimes possibility deserves equal time.

Maybe Security Isn't Always Staying

For most of my life, I thought security came from building something solid and holding onto it.

A steady career.

Seniority.

Knowing your job.

Knowing what's coming tomorrow.

And there is absolutely security in those things.

But I think there's another kind that I've only started to understand as I've gotten older.

The security of knowing yourself.

Knowing what you're capable of.

Knowing that you can learn.

Knowing you've handled hard things before.

Knowing that if something doesn't work exactly as planned, you'll adjust.

Maybe security isn't always knowing exactly what happens next.

Maybe sometimes it's trusting yourself enough to know you'll deal with whatever does.

That's a very different kind of safety.

And perhaps I needed to be 55 to understand it.

This Is Wellness Too

When I started GEN, I knew I never wanted wellness to be only about food.

Yes, what we eat matters.

Movement matters.

Sleep matters.

Taking care of our bodies matters.

But surely feeling well has to include the life we're living inside that body too.

How we spend our days.

How much of ourselves we give away.

Whether we're constantly depleted.

Whether we're curious.

Whether we're connected.

Whether there is still something ahead of us that makes us a little nervous and a lot excited.

I've written before about not waiting to live.

Apparently I'm now being asked to take some of my own advice.

Rude.

But fair.

Maybe this is part of whole-body wellness too.

Not quitting your job. That's definitely not going on my list of wellness recommendations.

But paying attention when something inside you keeps saying:

I think I'm ready for something different.

And being willing, eventually, to listen.

So... What Am I Doing?

I don't entirely know.

How's that for an inspirational ending?

I'm not going to tell you everyone should quit their job at 55.

Please don't send your employer a resignation letter and tell them Giselle from the internet told you to do it.

She did not.

I'm not going to tell you to blow up your life because you're bored on a Tuesday.

And I'm definitely not going to wrap this up with a tidy little It's never too late to chase your dreams! bow.

Life is more complicated than that.

Sometimes staying is the brave decision.

Sometimes leaving is.

Sometimes changing your life means doing something enormous.

And sometimes it means making one small decision that moves you a little closer to the life you actually want.

The hard part is being honest enough with yourself to know which one you're choosing — and why.

For me, it was time to leave.

So at 55 years old, after 28 years with the same company, I'm about to become the new person again.

I'm excited.

I'm terrified.

I'm incredibly proud of the career I'm leaving behind.

And I'm really curious about the woman who's going to walk into whatever comes next.

Every once in a while, my brain still whispers:

What the hell are you doing?

I still don't know exactly.

But for the first time in a long time, not knowing doesn't feel entirely scary.

Some of it feels like possibility.

And I think I'm ready to find out.