Why the Best Thing You Can Do Right Now Is Stop Following the Plan

There's this moment that a lot of women I talk to describe where a path that used to feel right just stops fitting. And the question underneath all of it is the one nobody really prepares you to answer: now what?

I sat down recently with Joanie Bily, the new CEO of Dress for Success, and within the first few minutes of our conversation she said something that stayed with me. She talked about how the biggest misconception women carry about their careers is that they're supposed to follow a straight line and if you're pivoting, you're somehow “off course.”

But what if the pivot is the course?

Joanie spent 30 years in the workforce solutions and staffing industry before stepping into the nonprofit world to lead one of the most meaningful organizations for women that exists. The way she talked about it sounded like someone who had finally arrived somewhere, not like someone who had “veered off track.”

That's the thing about pivots that nobody really talks about. They don't always feel like progress when you're in them. They can feel uncertain and a little uncomfortable, like you're admitting that the thing you were doing before wasn't quite right. But most of the time a pivot is an evolution. Everything you did before is still in there, just being used differently now.

I know this feeling personally. Leaving television after 30 years wasn't something I did because I had a perfect plan waiting on the other side. I did it because staying started to feel like the braver choice, and I knew that wasn't true. The clarity came after the pivot, and I think that's almost always how it works.

Joanie framed it in a way I really loved. She talked about asking yourself what makes you get out of bed in the morning, what you actually want to accomplish, what brings you joy separate from what looks impressive or makes sense on paper, and then staying true to that even when the outside noise gets loud.

That last part is harder than it sounds right now. AI is reshaping entire industries, job titles that existed five years ago are disappearing, and the pressure to stay relevant is real. Joanie was clear that this is exactly why women need to be more intentional than ever about their skills and what they're building toward. But she was equally clear about something else: fear is not a good enough reason to stay somewhere that has stopped serving you.

Take risks, embrace something new, and go for it anyway. I think what strikes me about that is how easy it is to agree with in theory and how genuinely hard it is to actually do. Because the thing holding most of us back is usually just the story we've been telling ourselves about what it means to change direction.

Your career doesn't have to make sense as a straight line for it to make sense. The skills you've spent years building travel with you wherever you go and the version of you that chooses fulfillment over familiarity is almost always more powerful than the one who stayed because it felt safer.

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Joanie also shared something that surprised me about Dress for Success. A lot of people think it's just about clothing and job interview prep, and while that's part of it, the mission goes so much deeper. They call it the five D's: dream, dress, develop, drive, and donate. They're working with women at every stage, from women re-entering the workforce to teachers and attorneys looking for their next chapter, across 130 markets in 15 countries. In a moment when so much is shifting so fast, that kind of community and support is exactly what women need right now.

If you want to learn more or get involved with a local chapter, visit dressforsuccess.org. And if you're in a season of your own pivot right now, I hope this gives you a little permission to trust it.

Watch our full conversation here.

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