Welcome to Rolling in D🤦🏻♀️h!
Divine disaster diaries from a breadwinning business owner living in New York City
If you’re new here, this post will get you oriented:
A bit more of the backstory . . .
I launched this project in the summer of 2023 on my 12-year biziversary, after getting The News (what my writing coach at the time called “The Ax”) from my favorite corporate licensing client, representing a six-figure recurring revenue payment, and concluding seven and a half wonderful years of working together. My stomach sank through the floor: What now?
My business and I were already tired after three long pandemic years, when I lost eighty percent of my income within two weeks after everything shut down in March 2020. This felt like leaving the comfortable shade of the corporate tree all over again, just like when I first left Google in 2011 after working there for five and a half years, to see if I could make it on my own. I genuinely didn’t know if I’d last six months.
All I could think to do was write. I didn’t know how I would pay the mortgage next month, let alone any of the following ones. I searched for “What to do when you lose your biggest client” on Spotify, hoping someone had covered this topic, but the results came up empty. So, in service to fellow small business owners, I’m now sharing my story from the messy middle.
After over a decade on my own, I’m pretty much unemployable, and I have a feeling my body and soul would revolt again if I tried. My husband Michael has taken to calling me, “his little pirate,” with the lucrative business boats burned (for now).
He does say I have a new spring in my step, a renewed sense of freedom and expansion, that the house has actually felt lighter ever since I processed The News and started channeling my waves of emotions into this project.
I have to admit: I feel lighter and freer too.
❤️
🏴☠️ I’d love for you to join us!
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About the Author: Jenny Blake
Jenny Blake is a keynote speaker and author of three award-winning books, including Life After College (2011), Pivot: The Only Move That Matters Is Your Next One (2016) and Free Time: Lose the Busywork, Love Your Business (2022).
For nine years, she produced two podcasts with over two million downloads combined: in 2015 she launched Pivot with Jenny Blake for navigating change (in the top 1% of podcasts), and in 2021 she added Free Time with Jenny Blake to set your time free through smarter systems (top 2.5%).
While at Google, her corporate alma mater, Jenny co-created a global drop-in coaching program called Career Guru that is still thriving today. Prior to that, she worked as the first employee at a political polling startup in Palo Alto later acquired by YouGov America. During her time at UCLA, she majored in political science and communications, interned at Rock the Vote, and graduated magna cum laude with Phi Beta Kappa honors.
She lives in New York City with her husband Michael, a contemporary fine artist from Beirut, and their angel-in-fur-coat German shepherd Ryder.
