Your Flight Path Has Changed
The distance between corporate life and self-employment sometimes feels vast
I live under the flight path of a bustling local airport. Planes fly over constantly — while I’m working from home during the day, and when I’m sitting on the porch after my kids have gone to bed, contemplating life.
Those planes make me think about the distance between the professional life I used to live and the one I live today.
For over a decade, I thought nothing of jumping on a flight for a meeting across the country or an international conference where I’d speak on a panel. I had an expense account, a title that meant something, stock options, a team, and a clear mandate. I knew what it took to be successful in my role — and I did that, and then some.
I loved the jet-setting, the socializing, the sense of being useful and important. My world was wide, and my career felt big. I’d risen slowly and steadily through the ranks, and my identity felt secure — even as media itself evolved around me. I understood how things worked.
Until they didn’t.
Today I work from home, by myself, all the time. Zoom and a laptop, like everyone else. I go to meetings, lunches, and networking events, but I’m usually here when my teenagers get home from school.
I am building a business from the ground up, brick by brick. No infrastructure, no playbook, no proven formula. I’ve done the research and I’m executing against a strategic plan — but it’s a plan we 100% made up. It hasn’t been vetted by bosses, because we don’t have those anymore.
The business is never not on my mind. I’m just as work-obsessed as I used to be, but it feels completely different.
I’m in control of my time for the first time in decades. I work all day, but I also exercise — something I could never prioritize before. I’m here for my kids, no longer outsourcing parenting to a nanny. My nervous system is calm and regulated after years of relentless stress. I don’t hide from my life in workaholism anymore. I can handle hard things head on.
I’m healthier now, and genuinely happier. I love the agency this path has given me, and most days I feel confident that — with persistence, luck, and the smart people around me — I will build something lucrative and meaningful that I can never be fired from.
But sometimes it feels like a very long way from the ground to being up in that plane, already successful and executing at a high level.
(A small aside: remember how excited you used to get about several uninterrupted hours on a flight to actually get work done? No meetings, no interruptions, maybe no wifi. That was how rare it was to have a window for thoughtful work.)
I wouldn’t choose that life today. I’ve changed. And the world has changed. The media industry I grew up in has become unrecognizable — fragmenting and contracting, with another layoff announcement every day. Snap, where I used to work, just cut another thousand people “due to the impact of AI.” It’s happening all around us.
So here we are — successful professional women in midlife, packaging our skills and starting our own businesses. Reluctant to call ourselves entrepreneurs after a lifetime tucked inside a corporate structure. Out on a limb and totally free, improvising and making it work as we go.
It’s worth sitting with that. Worth acknowledging that where we sit today is a vastly different seat than the one in Business Class.
In this new era, I have more space to think. My life is no longer jammed with meetings I didn’t ask for or priorities I didn’t set. Every day, I get to choose how I chase this next dream. And I don’t have to do it alone — there’s a whole generation of women out here making this transition alongside me, creating radical change in our lives, our careers, our identities.
I love this part of the journey, even though it’s more rooted on the ground.
I feel balanced. My priorities are finally in order.
And most importantly, I feel free.
Love,
Erin & Sarah
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