STUCK ON A SUNDAY - ISSUE NO. 3

“Career advancement” is a topic I have been thinking about a lot - and honestly, a topic I didn’t view as particularly complex until I got older - and my life got more complex around the career itself.

When you’re in college, doing internships, and have early career mentorship, career advancement feels fairly straightforward. The goal is onward and upward in every sense of the phrase. More pay. More responsibility. Bigger titles. Larger teams. More recognition. More perceived reliability.

But alongside that upward movement comes another parallel set of expectations: more scrutiny of your work, more dependency, more calls, more pings, more hours, more meetings, more interactions, more “can you just…” requests that quietly expand the edges of your day.

And yet you put up with all this because, well, “it’s just the cost of doing (well in) business”.

When I was younger, I was led to believe that — by senior leaders (ahem, Lean In), by politicians, by culture more broadly — that there should be no ceiling for women. And in many ways, I still believe that. Women are capable of doing all things.

But what that narrative consistently fails to acknowledge for me, and so many women, is that while there may be no ceiling, there are very real tradeoffs.

And not just the benign ones — like “not staying out late anymore” so you can take advantage of “early mornings at the gym before work”. I’m talking about the heavier, more existential tradeoffs.

Do you want to be the one picking your child up from school, or is that delegated to someone else?

Are you comfortable missing bedtimes to travel for conferences?

How important is a mid-day, mid-week recital if your partner is there instead?

How many children do you actually want once all of this begins to stack up?

I pursued career advancement — in the most traditional sense of that phrase — until I was about 30. I did everything that was asked of me, and often much more, in every role I held. But after getting married, thinking seriously about starting a family, growing increasingly frustrated with office politics, and having stress-fueled meltdowns with alarming regularity, something shifted. It simply began to matter less.

I still wanted to be paid. I still wanted a career. I needed stability.
But I wanted less. Less visibility. Less managerial responsibility. Fewer late-night calls. Less travel. Fewer people depending on me at all hours.

Then 2020 rolled around, and it changed it all even more for me.

I slowed down because I had to. I went full-time remote. I had a baby. I re-evaluated nearly every assumption I had made about work. And when I finally allowed myself to question whether I could keep going at the same pace — when I hinted that I was nearing a breaking point to my senior manager — the response from my company was familiar and predictable: I was offered a promotion.

At the time, it felt like the obvious answer. I had more money, a bigger title, and what was described as “autonomy” (a word we should interrogate more carefully). I was a mother and advancing. With “flexibility”. On paper, it looked like I had figured it out.

But in reality, I was unraveling.

I was funneling my anxieties about motherhood into work, clinging to childcare support as a lifeline rather than a supplement. At the same time, I was channeling my dissatisfaction with work into my personal life — venting to my husband, commiserating with equally burned-out colleagues, and carrying a constant, low-grade sense of failure that I couldn’t even admit to myself.

Eventually, the realization became unavoidable: I didn’t want career progression anymore — at least not in the way I had been taught to want it. Not because I lacked ambition (as the McKinsey & LeanIn report this week discussed), but because the structure itself was incompatible with the life I was living.

I didn’t have the time, the bandwidth, or the emotional capacity for advancement activities, volunteer committees, leadership development programs, or constant visibility. All of it paled in comparison to simply being present for my child — on sick days, on hard days, and in the quiet, ordinary moments that never show up on a résumé.

That’s when I had the epiphany many people arrive at when they move into consulting or leave corporate work altogether: I didn’t have to live like this.

I could still work. I could still earn. I could still grow. But I could do it in a way that was outward rather than upward.

And that distinction (outward versus upward career advancement) is what I don’t think we talk about nearly enough - and want to talk about today.

Upward career advancement is what most of us were conditioned to pursue. You start at the entry level, you move up, you get promoted, you take a higher-paying role at another company, and you repeat the cycle. Advancement is vertical, linear, and often modeled directly after someone more senior than you.

Outward career advancement looks different. It’s about taking the expertise you’ve built over years — often over a decade — and extending it outward. Applying it in new contexts. Teaching it. Lending it. Using it where it creates immediate value, rather than accumulating more responsibility for its own sake.

A real-life example of outward advancement: I recently spoke with a mom who left a government role after having children. After taking a short break, she accepted an administrative staffing position at a local hair salon. From the outside, some might label that a downgrade. She described it as one of the most fulfilling jobs she’s ever had. Her expertise is valued. She’s improved operations and staffing systems for this salon exponentially. The pay is solid. The hours are flexible. There’s no work after bedtime. It’s local, community-based, and sustainable. She is still advancing — just outward. And she gets 20 hours more a week with her kids.

As it relates to my own story, I say this as someone who spent fifteen years chasing upward advancement: I have loved focusing on outward growth these last two years. I may not be pursuing titles or seniority in the traditional sense, but I’m taking my expertise outward — working with early-stage founders entering the benefits space, translating what feels like “common industry knowledge” into guidance that actually helps them move forward. It’s part-time, well-compensated, intellectually engaging, and deeply rewarding.

Which is why the Women in the Workplace report last week felt so frustrating to many of us, especially me. By framing the conversation around an “ambition gap,” it reinforces the idea that upward mobility is the only legitimate form of progress. It overlooks the possibility that many women aren’t opting out of advancement — they’re opting out of a narrow definition of it.

Maybe the most fulfilling career paths aren’t linear at all. Perhaps they’re sideways, scaled back, reconfigured, or seasonally adjusted. Perhaps advancement sometimes looks like fewer meetings, fewer hours, and more clarity about what is enough. And perhaps the real opportunity lies not in convincing women to want more, but in expanding our understanding of what meaningful growth can actually look like.

That’s what I hope we continue to show is possible here with the stories and resources of Both&.

Take care of yourselves this week,

Kaleana