Flopped. Soared. Repeat. (A Career Story)
I'll be honest with you. I almost didn't write this one.
Not because it's too personal (in case you haven’t noticed, I’m a bit of an open book), but because it's the kind of story that sounds dramatic when you say it out loud. A downfall, a rebirth, then the pivot. But here's the thing: it's all true, and if you're sitting somewhere in the middle of your own career chaos right now, I think you need to hear it.
My career in marketing was a total accident. For as long as I can remember, I was the girl who had a whole other plan. Become a heart surgeon, move to New York City, and date occasionally. Then I unexpectedly met a boy, fell in love, and at 38 found myself moving to Grande Prairie, Alberta. Population: not Manhattan.
Over the past two+ decades, I've worked at a full-service agency, investment banking and real estate development firms, and across technology, junk removal, franchising, hospitality, municipal government, and now tourism. My résumé reads like one of those Japanese restaurant menus — twelve pages long, somehow covering every cuisine, and enough to make your eyes glaze over before you've even decided. Easy to mistake for someone who couldn't make up her mind. Turns out, she was just collecting experience she didn't know she'd need yet.
But let me back up, because before Grande Prairie, there was a moment that changed everything.
I was always terrible with money. Like, genuinely bad. And then one episode of Oprah changed everything. She ran a debt diet series — real families and couples crawling their way out of debt and back to financial freedom — and something in me finally clicked. One thing led to another, and I found myself on her stage with a group of women who had done exactly that. That accidental step into entrepreneurship opened doors I didn't even know existed: book deals, a television show, partnerships with companies like American Express, and a media career I never had the audacity to dream up on my own.
I couldn't have planned that. Not in a million years, but let’s just say I was not meant for a career in television. It was much more harder than I ever could have imagined.
And yet, after all of that, I still found myself here and that is 10 years into this chapter, wondering more than once if I'd made the biggest mistake of my life. My career has flopped. It has also soared. Sometimes in the same year. The rebounds were exhausting. The uncertainty was worse. At one point, I genuinely sat with the thought that maybe I'd just... stop. Be a housewife. Hang it up. And for a woman who has been professionally ambitious her entire adult life, that was a really hard place to sit.
But I sat in it anyway. I stopped running from the uncomfortable. I started taking care of myself in ways I'd deferred for years. I set boundaries — real ones, not the performative kind. And slowly, things started to shift.
I'm technically in my 50th year, though I'm only 49, and I am — for the first time in a very long time, maybe ever — thriving in a role where someone actually sees what I bring. A leader who trusts me completely. A team that lets me do my work without being a bottleneck, without second-guessing, or without getting in the way. Do you know how rare that is? I'm still a little in awe of it.
When you've spent years proving yourself in rooms that weren't built for you, being trusted fully feels almost foreign at first. And then it feels like wings.
So if you're in the messy middle of your own pivot right now — if your career has taken more unexpected turns than you planned for, if you've quietly wondered whether the best of it is behind you — I just want to say: I know that feeling. I lived in it for longer than I'd like to admit and I'm here to say it can turn around.
Sometimes when you finally get out of your own way, give yourself the grace to rest, and stop white-knuckling the plan — that's exactly when the right door opens.