Recent Podcast Episodes

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Jenny Blake Jenny Blake

228: The Burdensome B’s—Four Red Flags Signaling it’s Time to Make The Big (Delegation) Leap

“I’m at my wit's end.” That was the conclusion of a text message that broke my heart a little bit when a friend and fellow business owner showed it to me the other day.

Their team member sent it to them, expressing exasperation at the state of unfinished tasks in the business where they were waiting on an answer or action from the owner.

Seeing it bummed me out for both of them because it was neither person’s fault per se (though we can all take responsibility, of course). As I say in [Free Time](http://itsfreetime.com/book), business stress is a systems problem.

Today I’m sharing the signal flares to look out for indicating that something needs to change, with ways to communicate (and delegate) to stop the stressful pile-up languishing on your desk.

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Jenny Blake Jenny Blake

227: 🎁 The Best Gifting Strategies and Biggest Mistakes with John Ruhlin

“Nobody’s soul is moved by swag.” So says longtime friendtor of the pod, John Ruhlin, founder of strategic gifting company Giftology.

Since the day I met John and encountered his work in 2016, I have been inspired by his commitment to elevating the relationship game with generosity, “heart bombs,” and expressing genuine appreciation in the business world and beyond.

He does this all while setting up brilliant systems to make sure it all actually happens (such as setting a robust annual gifting budget aside off of top-line revenue). John is long overdue for a free time appearance, and I hope you enjoy this conversation as much as I did!

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Jenny Blake Jenny Blake

226: Is your business a hot mess? If yes, let's celebrate — Rolling in D🤦🏻‍♀️h

I used to refer to myself as a hot mess often in the early blogging days circa 2008, until someone scolded me saying it wasn’t a nice way to describe myself, that maybe it wasn’t the best self-image to curate. So I stopped. But I lost something in dropping the “hot” and the “mess” as I now approach middle age (and grandma-status in my soul).

Today's post is a crossover from my newest project, Rolling in D🤦🏻‍♀️h: Divine disaster diaries from a bread-winning business owner living in New York city. This is a paid Substack where I share personal essays about the real nitty-gritty aspects of running a business, especially when sh*t hits the fan. My friend Leanne calls it “business reality TV.” My husband Michael says it's picking up where Sex and the City left off, but this time about money.

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Jenny Blake Jenny Blake

225: How to Write a Must-Read Nonfiction Book with AJ Harper

“A book is not about something. A book is for someone.” That’s the mantra that drives AJ Harper’s work, which includes ghostwriting over one hundred books (and working on many more one-off chapters and projects).

In this conversation, she shares the “life of a book” process in her writing partnership with Mike Michalowicz (ten books together and counting!), what most authors get wrong when writing the conclusion, her favorite tried-and-true question to solicit “unexpected, delicious responses from interviewees,” and how to calibrate expectations for timing around the writing, editing, and creative process.

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Jenny Blake Jenny Blake

224: Create a See You Soon Kit for Clients — Jacq’s Favorite Time-Saving System

Do you already have an elegant way of wrapping up with clients? If you work with people one-on-one, it's important to systematize business values that you say are important to you, like surprise and delight, or giving clients a red carpet experience from start to finish.

Many of us have thought more about that on the front end than when we're actually closing out with a client—that's why I'm super excited to bring you this listener submission episode from previous guest and BFF, Jacqueline Fisch.

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Jenny Blake Jenny Blake

223: The Confidence Trap: Why You Don’t Need It to Do Big Things (SPARKED Crossover)

“Have you ever looked at someone else, someone you admire, who has accomplished a lot, and just assumed they must be wildly confident and always winning at everything? You’re not alone. But, the truth, it turns out, is much more complex.

So many of those luminaries are not, in fact wildly, or even remotely confident. And if they are, they go through cycles of profound change, self-doubt, struggle and, when they learn to harness these experiences, revelation and even reinvention.”

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Jenny Blake Jenny Blake

222: Why I Migrated My Three Email Lists to Substack (BFF Bonus Replay)

Now that I’m one month into Rolling in D🤦🏻‍♀️hI’m sharing my reflections on Substack as a software platform for personal writing (and potentially moving my newsletters soon too). I recorded this bonus episode for the BFF Community at the end of July; since then, I decide to officially migrate my Pivot and Free Time mailing lists and go all-in, and ‘doh has

;TLDR: I’m utterly delighted! The last time I felt this thrilled about software was when I first started tinkering in Notion four years ago, which became one of the best things I ever did for my business :)

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Jenny Blake Jenny Blake

221: Publishing and Personal Writing Pointers with Jennie Nash

“I see in books,” says today’s guest. “Every book is, at its heart, an argument for something—for a belief, a way of life, a vision of the future, a way to solve a problem, a way to make a friend, a way to lose your soul. The point is what the entire story drives to. It’s the thing your reader will come away from your book feeling.”

That’s just one gem from today’s guest, Jennie Nash, book coach and author of a blueprint series on how to approach your writing. Jennie and I discuss the tumult happening in hybrid and traditional publishing outfits; risks inherent in the publishing process; red flags to watch out for in selecting partners; determining the right genre for your work (i.e. nonfiction, fiction, memoir), how to “make room for the reader,” and what it means to write for the marketplace.

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Jenny Blake Jenny Blake

220: Why You Should Block Out Next August Now

I broke one of my own big rules this summer. For the last few weeks, I've been kicking myself, saying, how could I do this? I know better. I wrote a book called Free Time, after all!

Well, as I said in the introduction, business stress is a systems problem. Listen in for more on the mistake I made, and the systems and reminders I set up to ensure I have ample free time next summer.

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Jenny Blake Jenny Blake

212: Are You Future-Tripping? (Pivot Crossover)

As the saying goes, “Worrying is praying for what you don’t want.” A close cousin is future-tripping: projecting and living in the future instead of being present with what is actually happening, keeping an open mind about whatever might happen next. 

This crossover episode originally aired on the Pivot podcast on March 5, 2023.

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Jenny Blake Jenny Blake

211: 10+ Conference Networking Strategies with Alisa Cohn (Pivot Crossover)

Attending conferences can be overwhelming — even for the most excited extroverts among us, let alone the introverts who challenge their comfort zone in the registration process alone.

Today, my friend Alisa and I do an in-person debrief of our recent week-long adventure at the TED global conference in Vancouver (my second time attending, her fifth).

This crossover episode originally aired on the Pivot podcast on June 4, 2023.

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Jenny Blake Jenny Blake

210: ⛵️Knot a Care—Sailing the Free Time Seas with Joy and Ease

“My little pirate.” That’s the nickname Michael has given me this summer, as it feels like many of my corporate (client) income boats have burned these last few years. At the same time, he says he has never seen me so happy and free. “You’re not in a raft anymore,” he said. “You’re in a sailboat. You don’t want to be in the big cruiseliner anyway.”

Not to be confused with Sailing the Sea of Shiny Shoulds (I clearly love ocean metaphors!), today’s episode is all about embracing the agility and freedom that small business owners have to Sail the Free Time Seas. Heck, even one of the richest men in the world, Jeff Bezos, chose to buy a sailing yacht (albeit the world’s largest) rather than the more mechanized superyacht.

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