What Did You Love Before You Learned What Was Practical?

Last week I shared a quote from my newsletter that said:

“The older I get, the less I believe career pivots are random. More often, they’re people finding their way back to something they loved before the world told them who they should be.”

And it resonated with soooo many of you - because I think a lot of us are stuck in a veryyyyyy similar place of parenthood & career right now.

We’re successful on paper. We’re experienced and very good at what we do. Many of us have spent 10, 15, 20+ years building careers we should be proud of. And yet there is this nagging feeling that we are not entirely where we’re supposed to be.

Maybe, to you, it sounds like, “I don’t think I want to do this forever.”

Maybe it’s, “I know I’m good at this, but I don’t know if it feels aligned to what my family needs anymore.”

Or maybe it’s the message I probably receive most often:

“I don’t even know what I want. But something has to change.”

The more stories we collect at Both&, the more fascinated I’ve become by the career pivots people do end up making, and more so, the story that led up to them.

I meet ballet dancers turned interior designers. Executives turned cupcake shop owners. HR leaders turned retreat planners. Stay-at-home moms turned authors and coaches.

And every time, despite what outsiders may think of the extreme pivot they’d made, the majority of these people who make career shifts aren’t actually moving toward something completely random.

In fact, some of the happiest people I’ve interviewed didn’t have some identity crisis and pick a new life - they just leaned into more of who they’ve been all along.

The woman who now runs retreats was the kid who organized every neighborhood event. The person who started a coaching business was the kid everyone came to for advice. The founder who now spends her days creating content and teaching was the kid making magazines, writing stories, and forcing her siblings to participate in elaborate productions. The woman who owns a bakery wasn’t someone who randomly discovered baking at 42. She was the kid who always wanted to be in the kitchen.

And there’s obviously a deeply intrinsic reason for this.

Now, I’ve always loved personality psychology. I studied it in both my undergrad and graduate programs, and one of my favorite courses ever focused on personality studies and individual differences.

I literally took every assessment I could get my hands on. Myers Briggs. The Big Five. DiSC. Enneagram. StrengthsFinder.

Some people love astrology. I love personality tests.

Not because I think they can perfectly explain who we are…but because they often help us identify patterns.

Research has consistently shown that many of our core personality traits begin emerging surprisingly early in life and remain relatively stable throughout adulthood. Not perfectly, of course. We grow and evolve and change as life happens. But psychologists have found that many of our natural tendencies stick around much longer than we realize.

The curious kid often becomes the adult who asks one more question after everyone else is ready to move on. The helpful kid often becomes the person everyone turns to when something goes wrong. The organized kid becomes the one color-coding the family vacation itinerary. The creative kid somehow keeps volunteering to redesign the slide deck.

And there’s another concept I became fascinated with called person-environment fit. The basic idea is that we’re generally happier, more engaged, and more fulfilled when the environments we’re in align with our strengths, preferences, and personalities.

Which sounds obvious.

But how many of us actually chose careers that way?

Most of us chose careers based on practical considerations: what we studied in school, the salary, stability, geography, available opportunities, benefits, timing, family expectations.

And to be clear, there is absolutely nothing wrong with that. Most of us were making the best decisions we could with the information and circumstances we had at the time.

But it’s no surprise that so many people eventually start feeling restless with their choice.

Because they’re starting to notice the gap between what they do and who they are.

“Great,” you may be saying. “But this career identity crisis I’m feeling ‘might’ have been better suited for my late twenties, not right when I became a parent and have all this pressure and responsibility.”

And I think a LOT of people are where you are. So, why does this seem to hit so many people after they become parents?

Well, psychology has a few thoughts on that too.

One of the biggest misconceptions we have is that career identity is something we figure out in high school or college, get a degree in, and then we’re done. But researchers who study identity development have found that major life transitions often trigger periods of identity reconstruction.

As parents, we spend an incredible amount of time doing things many of us haven’t done in years. We spend hours playing. We spend more time creating. We are constantly building, imagining, and following curiosity for the sake of curiosity.

We’re also watching our children become themselves.

We’re watching them develop interests and preferences and little quirks. We’re watching them become completely obsessed with dinosaurs or art or music or organizing every toy in the house. We’re seeing personalities emerge right in front of us.

And if you’re anything like me, it becomes hard not to ask:

What was I like?

What did I love?

What could I spend hours doing before anyone told me what was useful?

Maybe that’s part of what’s happening. Maybe we’re spending so much time helping our children discover who they are that we’re accidentally rediscovering parts of ourselves too.

The kid who loved writing.

The kid who loved organizing.

The kid who loved helping.

The kid who loved teaching.

The kid who loved creating.

Which is why I don’t actually think most parents are having a career crisis. I think they’re revisiting who they once were - and sensing parts of their existing career and life that don’t align with their core personality.

Now, remembering who you were growing up doesn’t mean you’re supposed to become those exact things verbatim. But I do think it contains clues. Clues about the work that energizes you, the environments where you thrive, and the types of contributions that feel most meaningful.

Sometimes this leads to consulting, entrepreneurship, a side business, a return to school, or a completely different path. But just as often, it leads people to make micro-changes within the career they already have. A different role. A different company. A different schedule. More writing. More teaching. More creativity. More people work. Less management. Less travel.

Again, the point isn’t necessarily to change everything. The point is to understand yourself well enough to make decisions that feel more aligned.

Ok soooooo….. what do we actually do with all of this?

I don’t think the answer is to dramatically quit your job tomorrow and become whatever you wrote down in your third-grade yearbook. But, I also don’t think the answer is to ignore these feelings completely.

What I do think is worth doing is getting curious. Looking for patterns. Paying attention to what consistently gives you energy. Thinking about what you loved before practicality consumed you.

Asking yourself what kinds of problems people have always come to you for help with, what activities make you lose track of time, when you’ve felt most like yourself, and what themes have followed you throughout your life even as the job titles changed.

Because after collecting hundreds of stories, I’ve become increasingly convinced that most people don’t wake up one morning with a fully formed plan for what’s next. They collect clues, they follow them, they build on the side, and they pivot in whatever capacity they have at each juncture.

So I’ll leave you with the same question I’ve been asking myself lately:

What did you love before you learned what was practical?

Kaleana

Bonus: We have an upcoming webinar!

If you felt inspired by this, I hope you join us for a FREE workshop in a few weeks, “Finding Your Way Back: What Did You Love Before You Learned What Was Practical?”

Over the course of the workshop, we’ll walk through personality frameworks, strengths assessments, reflection exercises, and career pattern-mapping activities designed to help you identify the common thread running through your life, work, interests, and experiences.

Whether you’re considering a promotion, a consulting practice, a side business, a return to work, a career change, or simply trying to feel more aligned in the role you’re already in.

Hope you can join us (or RSVP to catch the recording!)