“Why Would You Want to Do That?” — When the People You Love Don’t Understand Your Career Pivot
When support feels conditional, it helps to remember who you’re doing this for.
That Look They Give You
They give you that look. The one that says, “I don’t get it.” Or worse, “I don’t believe in it.”
You finally work up the courage to share it. The dream. The idea that’s been whispering to you for months, maybe years. Maybe you want to leave your long-held job and try something new — part-time consulting, creative work, volunteering. Something slower, more meaningful, more you.
You say it out loud, hoping for encouragement. But instead you get that look — a mix of confusion and concern — followed by words like:
“Why would you want to do that?”
“But you’re so close to retirement…”
“Are you sure that’s a good idea?”
It stings. Even if it’s not meant to.
Love in Disguise — The Real Roots of Doubt
Here’s what I’ve seen in coaching conversations, in friends’ lives, sometimes in my own: when family pushes back, it’s rarely just about the plan itself. It’s about what the plan represents.
Sometimes they’re scared. Scared you’ll lose your security. Scared you’ll regret letting go of a steady paycheck. Scared you’ll be disappointed if things don’t go as planned.
And sometimes it’s just hard for them to picture you differently. You’ve been the VP, the manager, the go-to rock for years. “You’re good at your job.” “People like you there.” The idea of you changing that story — even if it’s for something more joyful — is unsettling.
Their doubt isn’t always rejection. It’s often love, tangled up in fear.
When Support Feels Conditional
Still, that doesn’t make it easy.
You might find yourself waiting — hoping that your partner, sibling, or grown kids will come around. That they’ll say, “I believe in you. Go for it.” And when they don’t, it can feel like a silent “no.”
It’s tempting to shelve the dream altogether. To think, If the people closest to me don’t see it… maybe it’s not worth doing.
Sometimes, the people you love need time to catch up to the version of you that you’re just beginning to believe in yourself.
Understanding Their Fears Without Abandoning Your Path
You don’t have to choose between your vision and your relationships. But it does help to have a game plan for those tough conversations.
Try leading with your why — the values behind the change. Maybe it’s about freedom. Maybe it’s about doing work that feels like it matters. Maybe it’s about having more time for your health or your family. Ironically, the very people who question your pivot might be the ones who benefit most from the you that emerges on the other side.
Listen to their fears, but don’t carry them as your own.
Who Are You Doing This For?
When the voices around you feel loud, go inward.
Ask yourself: Who am I doing this for?
If the answer includes your own well-being, fulfillment, or long-held dreams… that’s enough. It doesn’t need further validation. You’re not selfish for wanting something more aligned.
And you’re allowed to grow — even now. Especially now.
Build Your Own Believing Circle
Not everyone will understand your pivot right away. Some may never fully get it.
That’s why it helps to find your people — those who are walking similar paths, asking the same questions, making bold midlife moves. Maybe it’s a coach. Maybe it’s a peer group. Maybe it’s just one person who says, “Yes. I see it too.”
You’ve probably done a lot of networking in your career. Now it’s time to network with people more aligned with the you you’re becoming.
Finding people who’ve walked this road before you — or are walking it now — makes the path feel less lonely, less risky, and more real.
You don’t need universal approval for your decision once you’ve identified it as the right thing for you. What you need now is support from like-minded people who are doing the same, or have already followed the same path.
You don’t need everyone to understand right away. You just need to remember who you are becoming — and keep walking in that direction.
Have you faced resistance from loved ones when considering a big change? How did you handle it?
I’d love to hear your story — drop a comment or message me privately. We’re all in this reinvention chapter together.
