There is no gold medal for “Best Retired Woman.”

We just swapped the old rulebook for a shiny new one. Are you worried you aren't doing this stage of life "correctly"?

An uncomfortable, caffeinated realization came over me this morning while sitting on the patio:

I have entered the Olympic trials for a sport I never wanted to play.

I was comparing myself.

Not casually noticing what other writers were doing. Not gathering inspiration. No, I was doing the full-blown, toxic, “scroll through social media until your chest tightens” kind of comparing.

I looked at writers I admired and immediately decided their success was a direct indictment of my character.

Maybe I’m not thoughtful enough. Maybe I’m a fraud. Maybe they’ll find out I’ve just been winging it since 1985.

Once that old, dusty script got stirred up, I did what many of us do when we don’t feel like enough:

I tried to out-work the insecurity.

I built color-coded systems. I analyzed metrics. I hunted for strategies, formulas, and schedules.

There was just one glaring problem:

I was miserable.

I wasn’t having fun, and I wasn’t inspired.

Eventually, the women in my Breakthrough group staged a gentle intervention.

“What happened to you, Monica?”

Well, I’ll tell you what happened.

I took my eyes off my own plate and started looking sideways.

Human beings are wired to compare. We measure, we look around, we snoop. But if we are going to insist on using a measuring stick, we desperately need to change who we are measuring ourselves against.

Instead of comparing yourself to the woman down the street who somehow manages to bake sourdough, speak conversational French, and look effortlessly chic in linen, compare yourself to yourself.

Ask:

• Is this actually satisfying to me?

• Do I like the person I am while I am doing it?

• Would I still choose this if nobody else on Facebook knew I was doing it?

• Does this life actually feel like mine, or am I just wearing it like an ill-fitting coat?

These are not the questions we were trained to ask.

In fact, women of our generation are practically Olympic-level experts at looking outside ourselves for the rulebook.

We spent decades being told exactly what each stage of life was supposed to look like.

There were rigid, unspoken rules about being a good wife, a selfless mother, a competent professional, and a pleasant neighbor.

Be devoted at home, indispensable at work, attractive without appearing vain, and pleasant through the whole damn thing.

We learned precisely how much we should give and exactly how little inconvenience we should cause everyone else while doing it.

We were told to look young, act mature, work like we didn’t have kids, and parent like we didn’t have careers.

And then retirement arrives.

Finally, freedom!

Right?

Wrong.

For many women, we just swap the old rulebook for a shiny new one.

We immediately start worrying about whether we are doing retirement “correctly.”

The inner monologue shifts to a new brand of panic:

Should I be traveling more?

Should I be volunteering for three different boards?

Should I have taken up watercolors by now?

Should I want to be around the grandchildren 24/7, or is it okay that I love them dearly but also love when they leave?

Why don’t I want to play pickleball? Seriously, what is the obsession with pickleball?

It’s the exact same measuring stick.

We just changed the decade.

We are still standing at the pearly gates of our own lives, asking total strangers to tell us if we qualify to enter.

It is time to change the questions.

And it is time for them to become gloriously, unapologetically self-serving.

Yes, I said self-serving.

I know we were raised to hear that word as a character flaw, but at this stage of life, it ought to be the finish line.

After serving families, marriages, corporate ladders, churches, communities, and everybody else’s expectations, the self finally deserves a vote.

And not a polite, advisory vote.

The absolute, tie-breaking, deciding vote.

What dream did you put on a high shelf thirty years ago because life required you to be practical?

What have you been tolerating simply because you thought a good woman doesn’t make a fuss?

What happens if you stop asking whether your life looks right to the neighbors and start asking whether it feels right to you?

That is where the third act of life actually gets interesting.

Retirement is not a performance.

There is no gold medal for “Best Retired Woman.”

There is no panel of judges waiting to score your leisure activities, your downsizing choices, or the number of graphite paddles in your closet.

There are eight billion people on this planet, but there is only one you.

Which means there is literally no one else to compare yourself to.

So let me ask you:

Does the life you are living right now feel like the life you actually want to be living?

If the answer is no, that isn’t failure.

It is information.

And this time, you get to decide what to do with it.

f the answer is no, I don’t want you to turn that answer into another reason to judge yourself.

Because a life that no longer fits is not a ruined life.

It may simply be a life that was built for an earlier version of you.

A woman who had different responsibilities.

Different priorities.

Different people depending on her.

Different ideas about what she was allowed to want.

And now she has changed.

That matters.

You do not have to blow up your life, move to Portugal, buy a red convertible, or suddenly discover a burning desire to learn pottery.

Sometimes changing your life begins much more quietly.

You notice what feels heavy.

You notice what feels alive.

You begin remembering what you once wanted before practicality became the loudest voice in the room.

You start separating what you genuinely value from what you have simply been carrying because nobody ever told you that you were allowed to put it down.

That process has been such a significant part of my own life that I eventually wrote something I call Refoundation.

Not reinvention.

Not starting over.

Refoundation. Because I learned that I had to rebuild the foundation of my own life for me to move forward. Once I recognize none of the old rules were good for me, I did not hesitate, I took this as a opportunity to rebuild my own foundation that suites my life.

Because I don’t believe women reach this age as blank slates who need to manufacture entirely new versions of themselves.

We already contain decades of evidence about who we are.

What survived.

What mattered.

What disappeared because life demanded our attention somewhere else.

What still lights something up inside us.

Sometimes the work is not becoming someone new at all.

Sometimes it is digging beneath everything we accumulated and remembering the woman who was there before everybody else got a vote.

And then letting her have one again.

That is the possibility sitting in front of us now.

Not creating the perfect retirement.

Not finally becoming impressive enough.

Not winning the comparison game.

Simply building a life that fits the woman who is actually living it.

The conversations inside my Breakthrough Circle are useful, helpful and most importantly impactful. Anyway if this sounds to you like something you’d like to join, then the next step is to become a paid subscriber and become a member of Breakthrough. No attendence requirements. The circle meets every Tuesday evening at 7pm. Come and go as your schedule allows.