Some transitions are visible.
A promotion.
A new baby.
A return to work.
A parent getting sick.
A family structure changing.
But underneath those milestones is often something harder to articulate: the realization that the version of yourself that worked before no longer fully fits your reality now.
Josie’s Shift Happens series asked leaders:
The responses touched on leadership, caregiving, postpartum identity shifts, family systems, perspective, partnership, and the emotional recalibration that happens when life expands in ways you didn’t fully anticipate.
Below are their full reflections.
Founder + CEO, Auggie
Expectation: Once you become a leader, you’ll feel more in control.
Reality: You’re responsible for more than ever, at the exact stage of life when control is the hardest to maintain.
At work, people look to you for answers, calm, and decisions. At home, kids bring unpredictability, sickness, schedule changes, emotions, and constant needs.
You imagine leadership means gaining authority, but while parenting, it often feels like leading in the middle of chaos.
The real shock is realizing leadership is less about having everything handled and more about staying steady when nothing is.
Co-Founder, Charter | Chief Operating & AI Officer, The San Francisco Standard
My husband and I have flexed up and down at work and home for two decades, and the only real wisdom we have is that it’s never exactly 50/50, and trying to make it equal every single day will drive you crazy.
Years ago, we each took ownership of specific domestic domains. We joke that he’s the company CFO and I’m the COO. He handles meals, grocery shopping, Amazon subscriptions, laundry, our finances; I manage the family schedule and activity planning.
As our kids have grown, they’ve taken on responsibilities too. When someone in the family is in transition—a new job, more travel, the start of a school year—we sit down and renegotiate the things that tend to fall through the cracks.
The conversation surfaces the invisible work and forces us to decide together who’s carrying what, rather than letting resentment build over assumptions.
CEO + Founder, Shift Group
Within 2 months of each other, my daughter was born with a rare life threatening liver disease and my mother was diagnosed with end of life brain cancer.
As a leader it made me realize that the decisions we make, the mistakes of others and our own, and the short term outcomes or lack thereof — though they feel like life or death — are not even close.
I don’t work less hard or care less than I did before, I just face these situations with a lightness I have never had.
I’ve called it ‘gaining perspective’ — but what I really think it is — is actually understanding the reality of life.
The biggest thing companies miss is assuming all mothers return with the same goals, needs, and challenges. But every mother I’ve worked with is navigating something completely different: different pressures, support systems, priorities, and seasons of life.
And yet, the open and honest conversations that would help companies better understand and support them simply aren’t happening enough. Mothers need to feel empowered to ask for what they need, but it’s also on companies to build cultures where those conversations feel safe enough to have.
Executive Coach + Fractional Talent Management
No one really prepares you for the emotional and logistical pull of caring both ‘up’ and ‘down’ at the same time. Between getting kids out the door, taking on big projects at work, and managing a household, adding a parent’s serious health needs can shift everything overnight.
When my mom was beginning cancer treatment, I realized quickly: I couldn’t do it all — and I couldn’t do it all well. Something had to give.
My biggest shift was learning to prioritize based on my values in the moment, even when that meant stepping into a new version of myself. I scaled back and refocused where I could—at work, at home, even socially—so I could show up for my mom in the way that mattered most to me.
The other key was letting go of the idea that I had to carry it alone. I leaned more on my husband, brought in help at home, automated what I could, and adjusted my work capacity so that I could deliver high quality on the projects without overcommitting myself.
CEO + Founder, Rebranding Motherhood
One of the most overlooked parts of planning for a family is postpartum — because the truth is, everything you think you know about your capacity, your needs, and your systems will shift once you’re in it.
My strategy is to prepare for that fourth trimester with the same intention people often reserve for pregnancy: understanding feeding plans, recovery, mental health, and the real support required to function — not just survive. I encourage working with trusted experts to build a plan that centers both mother and baby.
From there, it’s about proactively communicating those needs in your professional environment before you return, so expectations are grounded in reality, not assumption. Because when moms are supported as whole humans — not just caregivers — everything works better, at home and at work.
The thread across all of these reflections was not perfection, balance, or “having it figured out” … it’s adaptation.
The understanding that leadership changes when caregiving enters the picture.
That identity evolves when responsibility expands.
That transitions force us to re-evaluate not only how we work, but how we define support, success, partnership, and capacity.
Because sometimes the hardest part of a transition isn’t the change itself. It’s realizing you can’t keep operating like the previous version of you anymore.
