Starting Over: The Art of the Awkward Pivot

Starting over in your mid-thirties feels like showing up to a teenage party that you weren’t invited to but stumbled your way there anyway. It’s awkward and a bit confusing because you still look young enough to kind of belong, but you have an old soul, and the lingo is different. Then something unexpected happens, you start having the time of your life. I’ve started over so many times in life that I almost feel like a pro, except it never feels good to end something that you invested in and spent time with or doing.

You would think that with all this practice of trying again in life, I’d be better at spotting the signs. I have this incredible pattern recognition, seriously, I can spot a narrative arc falling apart from a mile away in a manuscript. But when it comes to my own life, especially romance? I refuse to use it properly. Perhaps I always believed that the skill was work-related and not life-related.

I’ll see the red flags waving frantically. I’ll feel the vibe shift in the room. I’ll know, deep in my bones, that a chapter is closing. And what do I do? I dig my heels in for another three months. I try to edit the scene. I try to convince myself that maybe, just maybe, if I change the font size of my life, the story will make sense again. I use hope and optimism to sway my own thoughts.

The messy, beautiful truth behind it is that sometimes you just have to close the book and pick up a fresh notebook.

Let's talk about the big one. The transition from the "Corporate Baddie" to the "Freelance... What-Am-I-Doing-ie?"

For years, I wore the blazer. I spoke the language of "deliverables" and "circling back." I still hold on tight to the lingo when I have clients, but it’s much softer now. I had the badge that unlocked doors and the title that made my parents proud at Thanksgiving dinner. I had invested so much time climbing a ladder, only to realize I had leaned it against the wrong building entirely. I worked hard to secure a promotion every year. It was rewarding for a period of time, and the skillsets that I’ve gained are transferable

Leaving that behind was terrifying. Who did I think I was? Leaving a huge project management position with such high visibility was my dream... the top of the ladder. The paycheck was not the only thing that I was walking away from. I walked away from the identity that I carefully curated from college to my late twenties.

When I finally packed up my desk (or rather, logged out of Slack for the last time), I thought I would feel instantly liberated. Instead, I felt like a freshman on the first day of school. Suddenly, I was the HR department, the marketing team, the IT support, and the janitor of my own life. The journey was difficult and unexpected since I was also dealing with a terrible romance chapter.

I remember sitting in my living room at 11:00 AM on a Tuesday, wearing sweatpants, staring at my laptop, and thinking, “Is this it? Is this the dream? Is this peace?”

But then, the unexpected joy kicks in.

It starts small. It starts with the realization that you don’t have to ask permission to go to a dentist appointment. It grows when you realize you can choose who you work with. You start to find your voice again, instead of the corporate voice that was polished and sanitized for email chains, but your real voice. The one that’s witty, insightful, and a little bit loud.

For us, specifically—Black women in our thirties—starting over is an act of radical self-love. We are often taught to hold it all together, to be the pillars, to stay the course because people are counting on us. To look at a situation that no longer serves us and say, "I’m done," is a revolution.

I found that once I stopped trying to force my old life to fit my new reality, things got fun. I started connecting with other women who were also in the "messy middle." We swapped war stories about difficult clients and celebrated the tiny wins, like finally figuring out how to invoice properly or landing a project that actually excited us.

So, if you are sitting there right now, staring at a blank page in your life, feeling like you showed up to that party uninvited, grab a drink and stay a while.

It’s okay if it’s awkward. It’s okay if you don’t know all the new dances. You have experience now. You have resilience. You have stories to tell that you couldn’t have told ten years ago.

Starting over doesn’t mean you failed. It means you outgrew your old container. It means you are ready for a bigger, bolder life.

Yes, it hurts to leave behind what you invested in. Grieve that, especially a relationship gone wrong. But don’t let the grief stop you from seeing the potential of what’s next. Your story isn’t over, Hunny! We are just getting to the good part.

So, mess up the first draft of life's story. Try something that scares you. Ignore the patterns (or at least, laugh at them when you finally acknowledge them). We are rewriting the narrative, one awkward, wonderful day at a time. And trust me, this next chapter? It’s going to be a bestseller.

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Yours truly,

The Pivot Prodigy