I Was Retired for a Month. Turns Out, I Still Have a Lot to Say.

Left the grind but found my fire.

Jun 10, 2025

What surprised me most about retirement, which kind of snuck up on me recently (thanks in part to my man selling a company he founded), was how conditioned to work I truly was. I enjoyed my month off. But even before that started, I found myself reaching out to contacts and starting to think about this next phase of my life and career.

Partially, that’s because the past three years in particular were very intense. I couldn’t really imagine being in a state that wasn’t 24/7 high alert.

I also realized how much of my identity had become wrapped up in my professional life: I got my first job at 14, having lied and told the manager I was 15. Outside of maternity leaves, I have worked (and worked hard) for the majority of my life.

Rewriting the Stories That Held Me Back

The internal stories I carried were long and layered.

First, I told myself that somewhere along the way, I had chosen flexibility and motherhood over chasing some shiny career milestone or title,

Second, I let a few persistent voices live rent-free in my head. The ones that said, "You’re an execution machine, but not strategic enough." Or "You’re not visible to the right execs so your work won’t really count."

And third, I bought into the idea that because I hadn’t officially built out a certain function or led a particular team, it meant I wasn’t qualified even though deep down, I knew exactly what was required.

Throughout my career, I made a lot of decisions rooted in safety and necessity. I left a small startup - and a lot of money on the table - when I was pregnant with my third son so I could take a lower-paying role that gave me time with my boys and an extended maternity leave (eight glorious months).

Later, I stayed at a company well beyond my expiration date because the compensation was too good to walk away from. And the job gave me the financial security I needed to make a few really hard life choices and still set myself and my kids up well.

Even earlier in my career, I convinced myself that becoming a high-powered chief marketing officer (CMO) would pull me too far from the kind of mother I wanted to be. But ironically, I now think that staying stuck at certain levels for so long meant I worked harder, not smarter. And in some ways, my kids paid the price for that, too.

What I’ve come to realize is this: my experience is far more valuable than it looks on paper. And - maybe even more surprising - I have a strong voice. I have a lot to say. I’m finding myself in spaces where my guidance, instincts, and contributions reach far beyond just what I’ve done before.

And people want to hear it.

They want to learn from it.

From me.

How an Unexpected Nudge Unlocked My Superpowers

Within five minutes of retiring (and ten before I even announced it), a badass “real girl” friend of mine who's a marketing genius and mentor said, “You should come be an advisor for my private equity firm.”

My gut reaction?

Me? In PE? What would I possibly bring to that table?

Turns out: a hell of a lot.

During the first few weeks, I was guiding the firm’s managing directors, providing perspectives about portfolio investments, evaluating marketing strategies, and talking to CEOs who not only listened - but actually came back for more.

They valued my perspective. They told me it was changing how they think about growth, leadership, and the future of their businesses.

What do I bring? Thirty years of deep, real-world experience. I bring many, many (many!) situations that demanded a true understanding of complex problems, the influence chops to convince skeptical executives that my ideas are right, and the grit to do the really hard things others avoid.

I’m great at fixing what’s broken, building what’s missing, diagnosing problems at their source and, maybe my favorite part, seeing past the curves to anticipate what’s coming next.

That skill? It’s saved a lot of people a lot of time, money, and mess.

Now, I’m finally seeing what others are seeing, too: that all of this work and three decades of hard-won experience is making a real difference.

And it feels damn good to finally, really own that as something that I’ve done for myself, by myself, and because of myself.

A “Why Not Me?” Moment That Changed Everything

Back in 2019, I left a company I’d been with for nearly seven years, a place where I had strong credibility with execs, customers, and the marketing team to join a pre-initial public offering (IPO) startup.

The company I left was wildly successful and brought me a new level of financial freedom.

But I had a bucket list item: Work with a company navigating its IPO.

I knew it was a risk. But as I always tell my boys: if you’re going to take a risk, bet on yourself. I had to show them I put my money where my mouth is. And so I bet on myself.

What I didn’t know at the time was that about six months before our IPO, we’d be operating without a marketing leader. Which meant I found myself, along with a very small group of fellow marketers, suddenly knee-deep in IPO prep with no one formally leading the marketing charge.

So I stepped up. No title change. No salary increase. No permission slip. Just the clear understanding that someone had to steer the marketing ship.

I knew I could do it.

Let me be real: It was a massive beast. IPOs come with very high stakes, relentless and persistent big decisions, influential stakeholders, and a never-ending stream of critical deliverables.

There were plenty of late nights, stress-filled days, some tears, and more than a few “WTF am I actually doing?” moments.

I even had weekly “worry sessions” on the calendar with one of my long-time friends and teammates because sometimes, you need to schedule your spirals, and you need a partner to spiral with.

But I kept going. I made the decisions. I built the workstreams. I led the team. I handled the chaos.

And when we rang the bell on IPO day and I transitioned the reins to a brilliant new CMO, I had a moment of extreme pride in myself and what I’d done.

I also had a moment of pure clarity: I did a brilliant fucking job.

All the time I spent wondering if I was “the right person,” asking myself if I needed someone’s permission?

Those were the wrong questions. The only one I should’ve asked was: Why not me?

I didn’t just step into the role. I more than earned the right to it.

Although I didn’t have a marketing-leadership-during-an-IPO playbook or even a roadmap to know what shit was coming our way, I had the experience, the instincts, the grit, the persistence and the fire to lead through it.

Now, when I find myself facing something hard, unknown, or way outside my comfort zone, I don’t ask “Why me?”

I remind myself: Why not me?

Post-Retirement My Voice Matters - A Lot

There’ve been a few moments lately that have reminded me my voice really matters. CEOs and CMOs are reaching out for advice across the board about marketing strategy, organizational design, and how they’re building their teams. Even when it’s something I haven’t gone deep on before, my take still resonates. My perspective, my instincts, my recommendations - they are landing.

And here’s the best part: I still have more to give, but I get to do it on my terms. Sure, words of affirmation has always been my love language. But I’ve realized I don’t need a boss’s validation or permission to know my worth or how far I can go. This confidence wasn’t something I felt when I was younger and working full-time. I’ve gained that badge in this new phase of life.

I thought I’d walked away from the career world. But what I really walked away from was chasing someone else’s version of success and someone else’s view of who I am and what I can offer.

I’m building something new - a version of myself who was always there, in a way that I am defining myself and on my terms.

Like for so many Real Girls in their 50s, stepping back…or stepping out…and then stepping back in is scary. Looking for a job at this stage? It’s harder. Not impossible, just... harder.

I retired because I could. But something in me knew I wasn’t done. I had unfinished business mostly with myself. I wanted to prove that the old stories in my head weren’t true. That I could build a new chapter on my own terms - one that felt fulfilling, not like a slow death by calendar invites.

Turns out, I had a lot more game than I ever gave myself credit for.

Still, there’s tension. I spent most of my career making my own way: grinding, building, and providing for my kids. I didn’t take handouts. I wore that independence like a badge.

Now, I’m leaning a little more on my partner and his hustle. We’re building a life together but I’d be lying if I said that didn’t make me question whether I’ve lost some of my edge.

Being the primary earner gave me pride, power, and a sense of control. Letting go of that (even a little) felt like losing part of my identity.

I also felt relief. But right behind that relief? Fear. What if I have to go it alone again in my mid-50s? Could I?

This stage is full of contradictions. That used to knock me off course. Now, I let them sit with me. I can feel strong and regretful. Empowered and uncertain. I can chase new things - even when I don’t have a map - and still trust that I’ll figure it out.

Because I’ve done it before. And I know now: I still can.

Retired, un-retired, hit reset or plotting your bold midlife move? I want your story. Comment here or drop me a note at realgirlsguide55@gmail.com. You might just land in my book. Let’s make midlife loud, brave, and unapologetically ours.

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