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FROM THE HOST

You don't need a five-year plan. Try six months.

By Sondra Connor · 20 October 2026 · 4 minute read

“Where do you see yourself in five years?” I've been asked that in interviews. I've asked it in interviews, and I'm sorry. Because here's what I've learned from the women on this show: almost none of them could have answered it honestly. And the ones who could have would have been wrong.

In this note

  • Nobody picked their field on purpose. The tidy story gets written afterwards.
  • “I don't know yet” is a real answer. Especially when you say it without apologizing.
  • Decide in six-month windows. A five-year decision freezes you. Six months is an experiment.
  • Watch for the fake compass. If you don't pick a direction, the paycheck will.

Nobody picked their field on purpose

Lauren Fitzpatrick Shanks chose aerospace engineering from a department pamphlet. Alexandria Stylianou was moved into commercial fleet sales because the department had no women. Danielle Allen went from firefighting to aviation because she wanted to be an astronaut, and ended up in nuclear. Connie Clary started her consulting firm because a client mentioned she was good at telling people how to run their business.

If you'd asked any of them for a five-year plan at 22, you'd have gotten a confident answer and a completely different career.

“I don't know yet” is a real answer

Amelia Christofferson graduates in December. She ran her campus American Marketing Association chapter. She is sharp, organized and visibly good at this. And when I asked what's next, she said she doesn't know yet, and that she'll have a better idea once she has actually worked somewhere.

I loved that. Not because not knowing is the goal, but because she said it without apologizing. She's treating the next stretch as research: say yes to things you expect to dislike, find out, adjust.

The six-month window

Danielle noticed something about herself. She sits with an idea for about two years, and if it survives two years, she does it anyway. Her advice is to cut that to six months, because the decision doesn't get any easier by waiting and you lose the momentum.

Think about what that does. A five-year decision feels permanent, so you freeze. A six-month decision is an experiment. Try the job, the city, the certification, the side business. If it's wrong, you've lost six months and gained a very clear answer. Firefighter, paramedic, commercial pilot, flight instructor, physics teacher in Vietnam: that isn't a lack of direction. That's a lot of answers adding up.

Watch out for the fake compass

The catch with not having a plan is that something else sneaks in and steers. For Lauren, it was money. She hit six figures at 25, and the salary quietly became her North Star.

“I really did not know where I wanted to go. I didn't have that North Star except for the dollar figure.”

Lauren Fitzpatrick Shanks, episode 1

She only realized money wasn't her real driver after she left. Looking back, she'd tell her 25-year-old self to go get the psychology degree instead of the employer-funded MBA. So if you go plan-free, check your compass every so often. Are you choosing, or is the paycheck choosing for you?

A six-month plan you can actually use

The thing I keep coming back to

You don't have to know where you'll be in five years. You just have to know what you're trying next.

— Sondra