I’m excited to bring you this crossover episode with Rose Cox, founder of The HSP Business School and host of The Sensitive CEO Show ****podcast. She is one of the people I have been most excited to connect with across the globe the last few years, even though we have yet to meet IRL!

In this conversation, we dive into the world of highly sensitive people (HSPs), empaths, and introverts in the business world, with plenty of permission slips to stop doing what drains you. We discuss how to build a sustainable, soulful business that aligns with your energy, while embracing the strengths and challenges of being a sensitive CEO. Finally, we touch on Rose’s decision to pause her podcast (at least for now) after a year of releasing weekly episodes.

More About Rose: Rose Cox is an ICF-credentialed and Certified Human Potential Coach, 3 Brains Coach, Business Coach + Strategist, Advanced Rapid Transformational Therapist, Clinical Hypnotherapist and Energy Practitioner. Rose's unique blend of soul, science, systems and strategy combines her 20+ years’ experience in the fields of online business, hypnotherapy, coaching, and psychology to help her clients build a successful and sustainable business that is aligned with their energy and their soul. She works with highly sensitive people, empaths and introverts who have amazing gifts to share with the world but struggle with both the business strategies and mindset to fully step into their own.

Remove email and other social apps from your phone.

Try a guided meditation to speak with your higher self, or do free writing as if it’s a letter from your higher self to you. For encouragement around this, check out Elizabeth Gilbert’s new Substack, Letters from Love.

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Intuition is always speaking to you in subtle ways. Are you listening?

Intuition isn’t a gift that is only bestowed on a special few; everyone can strengthen this muscle—how loudly you hear these signals, and the trust in yourself to take action on the information you’re receiving.

In the comments of a recent ‘D🤦🏻‍♀️h post, Claudia asked:

I read your words “all-in on myself” and how you consciously cho(o)se to believe that the Universe was/is redirecting you, and can’t but think “Jenny’s so in tune with her intuition. No matter what comes, she has this trust muscle that allows her to keep going, to keep betting on herself and her ideas” and I wish I was “better” at it. Is this something you’ve gotten better at with practice? And is there any advice that you would share with us here about how to cultivate this way of being?

In this two-part solo episode, I’m sharing eleven strategies that have helped me build (and trust) my intuition at increasingly subtle levels. As always, I would love to hear from you! How do you practice the skill of following your intuition? Leave a voice note for a future listener-submission episode at http://itsfreetime.com/ask.

Trust your intuitive hits, even if you do not have a verbal or rational explanation (yet!) to validate the “memos” or make sense of your insights. Oprah says, “Your life is always speaking to you. It speaks in whispers guiding you to your next right step.” Are you listening? What is your life whispering to you right now?

Review your intuition history: Reverse engineer previous intuitive hits and the action you took; times you listened, times you didn’t. Times it “worked,” and times it didn’t — even then, you don’t always know what the bigger picture might have been. How did your intuition speak to you in these moments (a whisper, a feeling, an image)?

📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/232

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“Let’s build ESPN.com for strength, and convince everyone they can lift weights.” With this mission in mind, the first six months of building the BarBend platform were a blur for today’s guest. By the end of the first year in 2016, they had had 1.4 million readers. By 2022, they had over 31 million registered users, allowing them to sell the business in 2023.

In this conversation, we cover David Tao’s take on the media landscape and how to build a profitable content-based business; raising a seed round of funding from friends and family after getting rejected from every venture pitch; the biggest mistake he made while experimenting with monetization strategies; and how he navigated a successful acquisition with a shared vision at the new parent company, Pillar4.

More About David: David Thomas Tao is an entrepreneur and writer based in NYC. He's the co-founder and former CEO of BarBend.com, the world's premiere strength sports and strength training media platform. A proud Kentucky native, David is also a Forbes 30 Under 30 Listmaker, Kentucky Colonel, and a noted whiskey/spirits writer and judge, appearing yearly on national tasting panels. BarBend was recently acquired in a thrilling deal that included hiring all employees and the executive team has chosen to stay on as well.

If you’re bad at business development and partnerships, delegate that!

Consider what kind of help you could get on the “biz dev” front: what would be one small next step? Even if it’s something like employing the Cyrano Strategy for Delegating Important Comms so you aren’t the only one interacting with potential clients.

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“You can’t use up creativity. The more you use, the more you have.” —Maya Angelou

Earlier this summer, I arrived late one day to the podcast studio, laying on the floor in lieu of actually recording anything. Should I take that as a sign to reduce my creative output?

Not necessarily.

Aside from big one-off projects like writing a book, where I pour incredible time and attention to detail into (that I tackle every five years or so), I seem to do better with ongoing creative work by sticking to a stretch-worthy production schedule. These days I’m running a Delightfully Tiny media company that produces the following on a monthly basis:

By stretching myself to show up in these ways, I have discovered that there’s not always an inverse relationship between consistency and quality—at least for me.

Aim for consistency even over quality (knowing that “babysitting the work” doesn’t always help anyway), and permission to keep publishing even through energetic highs and lows.

Look back at your creative history: do you do better work with more constraints or fewer? What’s your sweet spot? There is no right answer. Bonus: Put a team and/or resources in place to help bolster accountability, take responsibility off your shoulders, and that raises the stakes (in a good way) of missing a deadline.

✍️ Check out Jenny’s personal business essays on Substack, Rolling in D🤦🏻‍♀️h

📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/230

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When we say trusting ourselves, which self are we talking about? Which parts of ourselves can’t be trusted?

That’s what we’re exploring today with returning guest, Ilise Benun. We discuss how confidence is a byproduct of action, what made her so angry that she decided to start her own business 35 years ago, building tolerance for silence and small experiments, and why she puts her phone number in her newsletter, on her website, and in the “from” line of her emails.

If you haven’t already, check out our previous conversation in episode 165: Are your clients bringing out the best in you? Engineering the Evolution of Your Business with Ilise Benun and episode 467 of Marketing Mentor on How to Free Your Time.

More About Ilise: Ilise Benun is the founder of Marketing-Mentor.com, the go-to online resource for creative professionals who want better projects with bigger budgets, through which she offers business coaching. She is also a national speaker and author of 7 books, including "The Creative Professional's Guide to Money," three online courses via CreativeLive and Domestika.org, and The Simplest Marketing Plan – all tailored to the needs of creative professionals. She has also been hosting the Marketing Mentor Podcast since 2008, with over 465 episodes at the time of this recording.

To listen to someone else. Find someone you trust, and just try something that they suggest—then see what happens.

Make a list of various selves; for example, the old self vs. the new self; rational self vs. the irrational self; the critical self vs. the compassionate self; the morning self vs. the afternoon self. Note who you trust most with business decisions, and which ones might be better to sideline.

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This is a free preview of this month's bonus episode for paying Free Time subscribers. Listen to the full episode (plus 100+ in the archives) and join us for live Q&A calls here »

***

They say write from the scar, not the wound—but what do you do when you feel called to write or speak from the wound? Do you forge ahead, knowing you will wake up the next day with a raging vulnerability hangover? Or do you keep it inside, bottled up for a future sell-by date?

Scott asks:

I'd love to hear you talk about seeking recognition / validation from others. Yep, kinda personal, so a bit vulnerable sharing here in direct email, but I do wonder if it's something that lies beneath the surface for me.

Possibly combined with an uncertainty about taking a step out of the corporate path about 5 years ago to go into full-time sports coaching and having a lot of pondering about that decision esp based on financial implications that came with it.

"Somebody tell me I'm doing the right thing / doing well / pat on the back" kinda chat would be amazing. Thanks again.

💬 What helps you move through vulnerability hangovers? What helps you try vulnerability experiments in the first place?

Join as a paying member or BFF to see the full show notes (related books, articles, and podcast episodes), then share your thoughts in the comments here »

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“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, 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.

Stop doing things that you're not even good at—that you dread, that drain you, that you procrastinate on. You also have full permission to stop trying to be somebody you’re not—even if that means a “business owner who is equally brilliant at big, creative thinking and administravia.”

Keep a piece of paper at your desk (or digital can work): note where you are in your zone of incompetence, competence, excellence, and genius.

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✍️ Check out Jenny’s personal business essays on Substack, Rolling in D🤦🏻‍♀️h

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“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!

More About John: John Ruhlin is the world’s leading authority in maximizing customer loyalty through radical generosity. He is the founder and author of Giftology: The Art and Science of Using Gifts to Cut Through the Noise, Increase Referrals, and Strengthen Retention and has been featured in Fox News, Forbes, Fast Company, Inc and New York Times. He and his firm now help automate this process for individuals and organizations like UBS, Raymond James, DR Horton, Keller Williams, the Chicago Cubs, and Caesar’s Palace.

Not be good at everything in your business; partner up with someone who fills in your skill gaps.

Double down on the personalization aspect of a thank you to a team member or client by sending a handwritten note, quick video filmed on your phone, or both!

✍️ Connect with Jenny on Substack: http://substack.com/@jennyblake

📝 Check out full show notes and share with a friend: https://itsfreetime.com/episodes/227

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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.

You can follow me directly on my profile page at Substack to see what I’m publishing across ‘Doh, Free Time, and Pivot at http://substack.com/@jennyblake.

To have messes in your business at the moment—even hot, complicated, gnarly messes. You are still here, and you are still learning and trying and troubleshooting; that’s all that matters.

Take a day or two off! Celebrate the mess if it means you’re still in business :)

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“A book is not about something. A book is for someone.” That’s the mantra that drives AJ Harper’s work, that 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.

More About AJ: AJ Harper is an editor and publishing strategist who helps authors write transformational books that enable them to build readership, grow their brand, and make a significant impact on the world. As ghostwriter and as developmental editor, she has worked with hundreds of authors, from newbies to New York Times bestselling authors with millions of books sold. She is writing partner to business author Mike Michalowicz, and together they’ve written ten books, including Profit First. AJ is the author of Write a Must-Read: Craft a Book That Changes Lives—Including Your Own.

📝 Permission: Abandon your timeline. Don’t overly obsess about deadlines, timelines, and where the book fits in your business plan.

✅ Do (or Delegate) This Next: We can all take strange comfort in knowing that no matter how many books you’ve written or how successful you are in business, “No amount of experience or preparation can save you from being nervous about the work you’re putting out into the world.”

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📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/225

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