This yom tov, while away with friends and family, I watched something unfold that I’ve seen a hundred times in my line of work—and a dozen times in my own life. My 21-year-old daughter was sitting across from another girl chatting casually about nursing school and next steps. You know these conversations: the kind that sound light and friendly on the surface but carry an invisible weight below the surface. The girl was explaining how she decided to switch schools, saying her new program offered better clinical rotations, stronger networking abilities, and a more direct path into the field. She was confident, articulate, and very sure.
As she listened, I watched my daughter’s face. She was smiling politely, nodding along, but I could already see it in her eyes: a mental spiral. An internal monologue. That invisible but familiar voice whispering: “Should I switch too? Am I already behind? What if I don’t make the right move?”
About twenty minutes later, my daughter came over to me during a lull between the main course and dessert with a subtle panic in her eyes. She began whispering in that half-whisper that daughters reserve only for mothers they both trust, yet fear will launch into a lecture.
“Ma,” she said. “What if I pick the wrong thing? What if nursing isn’t right for me? What if I stay in my present school and miss out on better opportunities like she has? What if I switch and regret it later?”
I looked at her, this smart, capable, sensitive young woman I raised, and for a second, wasn’t her mother anymore. I was her mirror. Because that panic? I’ve felt it. At 21, 31, and 42. Sometimes even now.
Before I could say anything, my husband—sitting nearby with zero context but excellent timing—chimed in without looking up from his chair:
“You’ll probably end up doing something totally different. Most people do.”
We both burst out laughing, but honestly, he wasn’t wrong.
That simple sentence captured what so many of us forget: Most people’s paths don’t go in straight lines. Most people change their minds. Most people land somewhere other than where they started, and it doesn’t mean they messed up. It means they grew.
I turned to my daughter and told her what I wished someone had told me at her age: “Whatever you choose, it is not forever. You’re just choosing the next step. No one can predict where they will end up in five or ten years. We just need to make the best decision for the version of us that exists right now. That’s not failure. That’s wisdom.”
She exhaled, like she’d been holding her breath the whole time.
And here’s the thing—I see this all the time. Not just with women in their twenties, but in their thirties, forties, fifties, and beyond. That same tight grip around needing to get it “right.” That fear of wasting time, making the wrong move, or disappointing someone—usually ourselves.
We’ve been sold this myth that there’s one perfect career path we’re supposed to figure out early and follow forever. But most people don’t live that way. Life isn’t a formula: it’s a journey of pivots. Your dream job at 21 might feel like a prison at 35. And your “fallback” job at 25 might become your calling by 40. That’s not failure. That’s becoming.
If I could talk to my 21-year-old self right now, I’d tell her:
“You don’t have to figure it all out today. You don’t need a perfect plan. You just need to keep asking yourself better questions. Stay curious. Pay attention to what energizes you—and what drains you. That’s the real data.”
And if I could speak to my 42-year-old self (which I can, because she’s literally writing this article), I’d say: “You’re not stuck. You’re not too late. Your capacity for change hasn’t expired just because you’ve built something stable. If your soul is whispering for more: more purpose, more alignment, more joy, you owe it to yourself to listen.”
Because here’s the truth: there is no one “right” path. There is only your path. And it’s okay if that path has curves, detours, pauses, and even dead ends that lead you somewhere else entirely.
This is the heart of the work I do. I help women who are in transition (whether they’re just starting out or starting over) figure out what’s next. I work with those who feel stuck, unsure, uninspired, or simply ready for something new but don’t know where to begin. Together, we make space for reinvention. For asking big questions. For letting go of what no longer fits and building what comes next.
So, if you’re 21 and standing at a crossroads, or 42 and realizing that you’ve been walking someone else’s path, it’s not too late. And it’s not too early. You are allowed to shift.
Because as Glennon Doyle says: “You can do the hard things. You just don’t have to do them alone.”
If you have a question about life, career goals, a situation you’re struggling with, or a topic you want to explore, send it my way and I will address it in a future article. Whether it’s about careers, relationships, personal growth, or navigating life changes later in life, I want to hear from you. Let’s talk about life, success, failure, reinvention, and everything in between. Because if there’s one thing I know for sure, we are never done evolving. n
Tamara Gestetner is a certified mediator, psychotherapist, and life and career coach based in Cedarhurst. She helps individuals and couples navigate relationships, career transitions, and life’s uncertainties with clarity and confidence. Through mediation and coaching, she guides clients in resolving conflicts, making tough decisions, and creating meaningful change. Tamara is now taking questions and would love to hear what’s on your mind—whether it’s about life, career, relationships, or anything in between. She can be reached at 646-239-5686 or via email at tamaragestetner@gmail.com. Please visit www.tamaragestetner.com to learn more.
