There’s a version of my life that looks, on paper, like a series of increasingly questionable life choices. Five marriages. Multiple states. A career pivot or three. An adolescence and young adulthood that I’ve had to recount so many times I could repeat it backwards. And here’s what I want to say to all of that: thank you. Not in a see it all worked out kind of way — God knows, it did not ALL WORK OUT. But in a genuine, chest-warm, no-notes kind of way. Because every single decision that looked like a disaster in real time gave me either a story, a lesson, a person I love, or something to write about. Sometimes all four. So this is my love letter to the bad decisions. You know who you are.
I’m not going to give you all of them. Partly because this is a blog post and not a memoir — yet — and partly because some of them are still marinating. But these ones are ready. These are the decisions that I’ve turned over enough times to finally see them for what they are: some of the best worst things that ever happened to me. Come sit down. I’ll tell you everything.
The Move
When I was 23, I sold basically everything I owned and moved to Houston with a man I had just met. I want to be clear about the timeline here: just met. As in, the ink on “nice to meet you” was barely dry. He would go on to become husband number three, which tells you roughly how that chapter ended — but that’s a different post. At the time, I had no immediate family in Texas, no job lined up, a half-cocked plan, and enough optimism to be genuinely dangerous. My parents were HORRIFIED.
We had nothing. I mean that in the most literal sense. After we wore out our welcome at my Aunt’s house (who by the way I had only met a handful of times and was gracious enough to allow us to live there for 6 weeks) we moved into an apartment and we didn’t even have a bed! We slept on the floor for over a month. We were young, dead broke, and just hoping we could make it happen. It’s terrifying — and inspiring.
And then I got pregnant.
My daughter was conceived in Houston — this city I had moved to on a whim and a prayer and approximately zero good judgment. We moved back to New Mexico before she was born, because that’s what you do when you’re young and broke and about to have a baby. But the next year my parents moved to Houston. And then we moved back. And then life just… kept happening here, the way it does when a place decides it’s yours whether you planned it or not.
That impulsive, ill-advised, absolutely chaotic move gave me my daughter. It gave me Texas. It gave me the city that my whole family eventually found their way to — like I accidentally scouted the location and everyone else just followed.
Worst decision I ever made. One of my favorite outcomes. No notes.
The Road Trip
Freshman year of college. I was 3,000 miles from home, which was either incredibly brave or incredibly stupid — jury’s still out. But I had a car, which in a freshman dorm makes you either very popular or very taken advantage of. It was ABSOLUTELY both.
A friend came to me frantic one afternoon with a request that had absolutely no business being a yes. She needed to get from Roanoke, Virginia to Fort Leonard Wood, Missouri — her boyfriend was graduating from boot camp and she was going to miss it if she didn’t find a way there. She looked at me with the specific desperation of someone who has already done the math and knows they’re asking too much.
Then she told me the dates.
Finals week.
Reader, I said yes anyway.
We spent that entire day taking exams — the kind of mental marathon that makes your brain feel like a wrung-out dish towel — and then at three o’clock in the afternoon we threw bags in my car and pointed it west. We drove through the night, pulled into the hotel near the base, it was a little after 7 am. I laid down in the bed, and crashed. My friend? Made it to the ceremony. By the afternoon we were headed back to Virginia so exhausted we both hallucinated — at least once. Shapes moved in the road, lights swerved into our lane, and we smoked a carton of cigarettes in an attempt to not die on a freeway that night.
We each had to reschedule a final. It was completely unhinged. It was also, without question, the best road trip of my life.
Here’s what that trip gave me that no exam ever could: the knowledge that I was someone who showed up for my friends — not when it was convenient, not when it was planned, but when it mattered. I was 18 years old, far from home, and making my own calls. That drive taught me more about who I was than anything I studied that semester.
Some risks don’t pay off. That one did. And I’d do it again in a heartbeat — finals be damned.
The Flight
After my third marriage ended, I did what any reasonable woman in her thirties does when her life is falling apart: I flew to San Francisco to meet a man I had never seen in person, whose last name I’m not entirely sure I knew, because he was my right hand man in an online mobile game.
I need you to sit with that for a second.
For over two years, I had been deep — cringe level deep — in Game of War. You know Kate Upton, Superbowl commercial Game of War. Absolute, total nerd shit. I had spent somewhere in the neighborhood of two thousand dollars on this game, which is either a cry for help or a flex depending on how you look at it. I built an alliance, earned a leadership role, and took the whole thing embarrassingly seriously. And in the way that only the internet can arrange, I had made real friends — people I talked to regularly, people who knew my actual life, not just my username.
Dindo was my VP. The way that Chibs is Jax’s VP in Sons of Anarchy. Full on right hand man, ready to burn everything to the ground to uphold your leadership and legacy. We had never been in the same room. Hell — we had never been in the same STATE. When my marriage finally kicked the bucket, he was one of the first people I told. His response?
“Come to SF. On me.”
And I went. I just — went.
I want to be honest with you: he could have been a serial killer. A rapist. Someone else altogether. I had exactly zero verified information about this man beyond the fact that he was loyal to my leadership online and kind on the phone. I got on a plane anyway, because I was over being miserable, dying for some agency and definitely not thinking clearly, and those three things will make you forget that your mom always says, “Make good choices.”
It was the best trip of my life.
Dindo showed me San Francisco the way locals show you a city — not the tourist version, the real version. We saw all the sights, ate at Harvey’s in the Castro District and had authentic Filipino breakfast on the beach while the sun rose. He was exactly who he had always seemed to be, which is not guaranteed when you meet your internet friends in the flesh but was, in this case, a full-on miracle. It was cathartic in the way that only comes from captaining your own ship. I came home different. Stronger.
I also could have died — or worse. I know, it was reckless. But I didn’t. And sometimes that’s the whole story.
It looked, from the outside, like a woman in retreat. It was actually a woman getting a running start.
The Leap
Not every bad decision looks like a road trip or a flight to meet a stranger. Some of them look like a pay cut.
I was working for my fourth husband’s mother — which, if you know anything about how that marriage ended, you already understand why I had to get out FAST. I could see the divorce coming the way you can see a storm on a Texas horizon: far enough away to pretend it isn’t, close enough that you’d be a fool not to move. So, I jumped — head first into an awkward resignation chat with my mother-in-law and prayed I would land before the storm hit.
I took a job at a tech firm that was a demotion in title and forty thousand dollars less than I was making. Forty thousand. Full stop. I stressed through every step of the process, endured every elementary question I could answer in my sleep and said yes with absolutely no backup plan.
To this day, it’s one of the most humbling professional experiences of my life. And I was terrified in the way you can’t tell anyone about — the kind of scared that lives in your chest at two in the morning when you’re running numbers you already know don’t add up. My husband moved out before I had even finished the training program. I genuinely did not know if I was going to be able to pay rent. I was overqualified, underpaid, and starting over in every direction at once.
And then I got to work.
Because here’s the thing about taking a job below your level when the culture is good: you don’t have to shrink to fit it. You GET to own it. The company gave me plenty of support, a challenge and the kind of autonomy that motivates you to CRUSH IT. I stopped surviving and started building. By month eight I was making twenty thousand more than I’d earned grinding away for my ex’s Mom.
The level after that?
Chief Revenue Officer.
I took that pay cut to save my own life — professionally, personally, all of it. It looked, from the outside, like a woman in retreat. It was actually a woman getting a running start. There’s a difference. It just doesn’t always photograph well.
I don’t want you to misunderstand, not every bad decision works out, and I’m definitely not saying that it does. A lot of my bad decisions ended up in absolute disaster. The kind that earns you the need to apologize to your kids, your friends, your parents and then get a really good therapist. Some of them were so damn painful they still keep me up at night. I’m not writing this to convince you that chaos as a lifestyle works. I’m writing this because I spent a lot of time being embarrassed about the way my life didn’t follow a straight line, and apologizing for a story that was never as shameful as I allowed others to convince me it was. The decisions that scared me the most — the ones that looked the absolute worst on paper — turned out to be the ones that knew something I didn’t yet. Not always. But enough times to notice.
So here it is. My love letter.
To the man I barely knew and the city I followed him to. To the daughter I made there, in a place I had no business being. To the road I drove in the middle of finals week because someone needed me to show up and I was, it turned out, exactly the kind of person who does that. To the stranger in San Francisco who was exactly who he said he was, and the trip that put me back together when I didn’t know I was in pieces. To the pay cut that looked like surrender and turned out to be the best investment I ever made in myself.
You were all terrible ideas.
You were all completely worth it.
I wouldn’t rewrite a single one — not because they didn’t cost me anything, but because what they gave me back was better. A daughter. A city. A self that knows she can drive through the night, get on the plane, take the leap, own the room.
That’s not a cautionary tale.
That’s just my life. And honestly? I love it here.
