What I Know Now About Work and Life and What It Cost to Learn It

For a long stretch of my career, I was very good at a job that was slowly taking me away from myself. I couldn’t see it because every external signal told me I was succeeding.

I spent more than two decades across apparel and fashion operations and then the tech industry, most of it leading workplace transformations. I was the person you called when something complicated had to get done while keeping the business running. I was good at it, and the scope kept growing, which is how organizations tell you they approve of your hard work and willingness.

I also became a mother during those years, and eventually my daughters grew up too familiar with “not yet,” “not now,” “one sec,” and “I’m tired.” They had no way of recognizing I normalized overwork.

I told myself the arrangement was temporary. After this project, after this season, after the reorganization settled. I repeated similar versions for years, and I believed it every time.

The part nobody says out loud

People ask if I had an epiphany, and the honest answer is that it was never one single moment, but an accumulation of observations.

I was living under the expectations of others, inside a definition of success that was superficial and relentlessly demanding at the same time. My creative and expressive self was evaporating, and I could feel it.

The clearest evidence showed up in the car. I often drove my girls to school and activities with a work call running, shushing them in the background. Who else was going to do it? They were getting the remnants of my energy and attention. Nobody approved of that arrangement except my employers, who inevitably wanted more. I had yet to awaken to the possibility that an alternative existed.

It must be me

Most of the accomplished women I know have their own version of this story, and almost all of them reach the same conclusion I did. I must not be organized enough, disciplined enough, or as good at this as whoever appears to be managing it better.

Every woman I talk to believes she is the only one failing while everyone else has it figured out. The belief is costly, and it’s wrong.

Then everyone saw it at once

March 2020 forced millions of people to rethink how they lived and worked. In the same month, people everywhere were rebuilding their time and commitments around something nobody planned for, without the typical supports.

Some found what they'd been missing for a decade. They ate dinner with their kids, stopped commuting three hours a day, and noticed their work didn't suffer. Others learned that the flexibility they wanted for years had conditions they didn't anticipate. What those months during the pandemic proved is how nimble organizations can really be.

The scale of its impact is documented. Census Bureau research shows that between March and April 2020, roughly 3.5 million mothers with school-age children stopped working. By April, nearly 45% of moms were not working with only a third of fathers absorbing the impact.

A realization you have alone at 2 AM is easy to explain away as a personal failing by 9 AM, but a realization by several million people in the same month is much harder to dismiss.

What I did with it

I enrolled at the University of Pennsylvania’s Graduate School of Education and spent four years on a doctorate studying the human experience of work, specifically how working parents evaluate the support their organizations provide. I interviewed 35 working parents on what works and what doesn’t. One finding reorganized how I understand my own 20 years of experience.

If you recognize your experience in any of this, try this exercise: Write down what you would keep about your current arrangement if someone handed you the choice, and what you would not. The gap between those two lists is where the work begins.

What comes next

The next public cohort of Entirely You™ opens in January 2027, and seats are limited by design. Join the waitlist to hear when enrollment opens.