Welcome to Rolling in D🤦🏻‍♀️h!

Divine disaster diaries from a breadwinning business owner living in New York City

I launched this project in the summer of 2023, on my 12-year biziversary, getting The News from my favorite corporate licensing client concluding seven and a half years of working together. My stomach sank through the floor: what now?

My business and I were already tired after three long pandemic years where I lost 80% of my income in one fell swoop when everything shut down in March 2020. This felt like leaving the comfy 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).

When I got The News, all I could think to do was write. I didn’t know how I would pay the mortgage next month. I searched for “What to do when you lose your biggest client” on Spotify, hoping some podcaster had covered this topic, but came up empty. So, in service to fellow small business owners, I’m now sharing my story from the messy middle.

Each phrase of the Substack name has meaning:

  • Rolling in Doh: A play on dough, with rolling and dough connecting to the breadwinner metaphor. Doh signaling all the things that go wrong, while still calling in the abundance of “rolling in dough.”

  • Divine Disasters: An optimistic take on the inevitable challenges that arise when self-employed. Searching for faith, surrendering, holding onto hope, and practicing trust as crucial elements of (to apply every apt cliché): weathering these storms, turning lemons into lemonade, seeking silver lining, and looking for the gifts in the garbage.

  • Breadwinning Business Owner: With both of these roles, breadwinner and business owner, the person at the center takes on a huge level of pressure x uncertainty x responsibility. There is no one coming to save you. The household isn’t bolstered by a spouse in a high-paying job. As a business owner, there is none of the certainty behind a twice-monthly paycheck (even if the fear of getting fired looms).

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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Paid subscribers can also read and reply in the comments: Cheer others on, weigh in on your divine business disasters, and share what you’re learning along the way.

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The Origin Story

Read about why I launched this project in the opening series:

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About the Author: Jenny Blake

Jenny Blake is a podcaster and the 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).

She has 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.

Jenny is a lifelong bookworm and aims to work ~10-20 hours each week, leaving plenty of time to take her angel-in-fur-coat German shepherd Ryder to the park to play with sticks on their favorite grass-covered hill every afternoon. She lives in New York City with her husband Michael, a contemporary fine artist from Beirut, Lebanon.

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🎢 Divine disaster diaries from a breadwinning business owner living in New York City.🗽 Posts go live Wednesday and Saturday at 11:11 a.m. ✨


Hi! I’m a Webby-nominated podcaster and author of three award-winning books, including Pivot (Portfolio, 2016) & Free Time (Ideapress, 2022). I love coffee, books, yoga, serendipity, and Substacking! I live with my artist husband and GSD Ryder.