I Had It All, Remember?

A candid reflection on success at 20 vs wisdom at 40+, and why the 'too late' narrative about midlife dreams needs to be unfucked

This morning, while running with my daughter through a neighborhood adjacent to where we're staying—one of those places we return to each year—I found myself slipping into old thoughts.

The homes were sprawling one-stories, each tucked a quarter mile down a long driveway, surrounded by perfectly green, overly manicured lawns. They felt... ostentatious. Still, I found myself wishing I had something like that. Again.

I heard construction trucks rumbling in the distance and realized the lot nearby was being excavated. The footprint of the house was massive. I was immediately transported back to the days when I used to pull up to my own job sites to visit my then-husband, a homebuilder. Our toddler son bouncing on the tractor seat. Ocean views in the distance. Palms lining the roads. Concrete being poured into what we believed were permanent futures. I had that. I built that.

And for a second, I wished I had it all figured out now like I did then.

The next thought tried to sneak in—you won’t be able to achieve that again—but I caught it. I unfucked it.
Because I’m not here by accident. I’m here because of everything that came before. And if I built it once, I can build again—only this time, with even more clarity.

As we walked the path back to our casita, my daughter asked, “Did you ever play Sesame Street for us when we were little?”

“Maybe a little,” I said. “But by then there were so many other shows—Dora, Wonder Pets…”

She laughed, “Yo Gabba Gabba.”

We didn’t really watch much of that one, I reminded her.

“No,” she said, “we were already a little older.”

I told her something I hadn’t thought of in years: “Funny thing, I didn’t even know about that show until my ex—my ex who was in a band—was on it, after he had his first baby.”

And just like that, another past version of me bubbled up. The one who still believed he was “the one.” Even after we ended. Even as our lives moved on. Back then, seeing him on a kid’s show with his new baby was enough to send me spiraling. I wasn't just watching a segment—I was watching the life I thought I was supposed to have play out with someone else.

It’s always something, isn’t it?

We get one area of life smoothed out while another scratches at us, whispering: this isn’t it. There’s more. There’s different. There’s better.

Over the weekend, I was talking about midlife—specifically, how my 40s have become a time of reclaiming.

Reflecting on my 20s and 30s, it's clear that who I am and what I desire at the core hasn't really changed—especially when it comes to work, passion, and creativity. Ironically, I had equal parts boldness and low self-worth back then. I was fearless, but not exactly rooted. I mistook my impulsive thoughts and emotions as my compass. Got an idea? Acted on it. Unhappy in a relationship? Sat in it for years… but only through the lens of my own alibi, plotting my exit.

Now in midlife, I want many of the same things—but I've finally found that inner sense of power and self-trust. At the same time, a new voice has crept in, echoing fears I didn't have at 20. The difference? I now have the awareness, the tools, and the lived experience to work with those thoughts instead of letting them run me.

The hard part about midlife isn’t the lack of opportunity—it’s the loud, collective voice telling you it’s too late.

But I’m not buying into that.

I may not be pouring concrete anymore, but I’m still building. This time, it's not just homes or businesses—it's me.

Okay, but there is a business in there too, and I keep reminding myself:

babe, if you've done it once, you can absolutely do it again.

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For paying subscribers: This piece brings up a lot - I know because I'm still processing it myself. If you're feeling called to dig deeper into your own "I had it all" moments and the stories you're telling yourself about past vs. present, I've created a reflection worksheet to guide you through it. Sometimes we need more than just reading about these insights - we need to actually work through them on paper.

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