226: Is your business a hot mess? If yes, let's celebrate — Rolling in D🤦🏻♀️h
8 Dec 2025 · 11 min
Podcast episode (hosted by Jenny Blake) titled around the theme of embracing being a 'hot mess' in entrepreneurship. The episode includes an excerpted personal essay ('Hot Mess') from Jenny's paid Substack Rolling in Dough/Rolling in Divine Disaster Diaries, reflections on non-linear personal and business change, courage in leaving stable employment, and promotional calls-to-action for joining her Substack and newsletter. The transcript also contains multiple commercial ad reads (Sprite, Venmo Stash, Columbia, Mint Mobile).
Chapters
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No matter how many times I hear it, no matter how many times I say it, it helps to be reminded the change process is not linear. We spiral upward, outward and inward through cycles of death and rebirth. From Hot Mess to Business badass and everywhere in between.
This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
Welcome back Free Timers. Today's post is a cross post of sorts from my semi secret substack Rolling in Divine Disaster Diaries from a breadwinning business owner living in New York City. This is my paid substack where I share personal essays about the real nitty gritty behind the scenes of running a business. My friend Leanne calls it business Reality tv. My husband Michael says it's like Sex and the City but about money. So if you want to join us over at DOUGH for short, I would love for you to be part of that community too. Visit rollingindo.substack.com or itsfreetime.com secret. You can also follow me directly on my profile page@substack.com ennyblake I also highly encourage you to check out the Substack app so that you can read essays like this and from tons of other writers that you admire and enjoy from within the app and outside of the chaos of your email inbox. Without further ado, here's today's excerpt and I'll be sure to link to the written version of this post in the show Notes.
Hot Mess. I'll have what she's having August 26, 2023 today I spotted a sign hanging off the scaffolding at the burger joint a block from our apartment. As if for the first time in tiny all caps lettering on an orange yellow gradient background, it prompted are you ready for a Then in dripping black huge horror movie vibes, Hot Mess. That's me. I thought with a smirk. 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 message As I now approach middle age and grandma status in my soul, I'm not as hot and my life is much more messy, even if more meaningful. It's also swelteringly hot and humid as I write this, and I have thusly coined a new term for certain summer moods thangry tired, hot and angry. On July 9, 2020, I sent a newsletter for Pivot List by Jenny Blake.
I just heard a meme that 2020 is now an adjective, one akin to hot mess or disaster, as in ugh, that's so 2020. Ha. I'm still looking for the silver lining. Does anyone else feel totally exhausted and lacking in motivation? Maybe it's just me, New York City humidity and the hourly evening bespoke fireworks that have woken me and my family up five to ten times a night for almost a month now.
Oh sweet, sweet 2020 self. I wish I could pat her on the head. You have no idea how much harder things will get. And yet, strangely, more joyful too. Eventually, the tension I described wouldn't release for years. Three to be precise. Just three weeks later, Michael's neighborhood in Beirut, as densely packed with life, homes, culture and restaurants as the West Village, would be destroyed by a blast bigger than all the fireworks in New York City combined. We were just getting started. Then I share a quote from Charles Eisenstein from his book the More Beautiful World Our Hearts Know Is Possible. The first step in creating change, then, is to receive a vision that feels true. The second step is to heal the wounds and doubts that that vision illuminates. Without doing that, we will be conflicted, simultaneously enacting both the new story and the old one that accompanies the wounds. The third step is to bow into service to that which wants to be born. This process is not linear. No matter how many times I hear it, no matter how many times I say it. It helps to be reminded the change process is not linear. We spiral upward, outward and inward through cycles of death and rebirth, from hot mess to business badass and everywhere in between. Entrepreneurship is one of the greatest personal growth journeys you can undertake. You will be asked to confront your biggest fears until you transform them into paper tigers. You will nearly crack under pressure. You will realize that no one is coming to save you that you must first save yourself. You will learn from every mistake and mess you make, because otherwise you'll go out of business.
We'll be right back just after this.
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In December 2011, I published a blog post called Courage Isn't Always Glamorous. Actually, it almost never is. It started with the following anecdote. After a recent speaking engagement, someone came up to me and said, well, what you're doing is really courageous. Leaving your job, Google of all places, and the safety of a paycheck to start your own company. I want to do that someday. She saw my decision as courageous, and don't get me wrong, I do too. But more than that, I saw it as oxygen. It's what I needed to do in order to breathe again, in order to exhale, in order to live the life that was waiting for me on the other side of a seemingly insurmountable, suffocating mountain of fear. I loved Google, but my heart turned elsewhere even before my mind did deja vu. Later in the post I write, courage is earned through tears, fears, heartbreak, and failure. It's messy, ugly, rocky, and you find your courage when you have no choice but to trust it. Courage isn't always glamorous. Courage is crying. Snotty, unattractive, red, splotchy, hysterical crying because you know what you need to do, but you're scared to actually do it. Courage is going to sleep so heartsick that you can't find the strength to change out of your clothes, but getting up and out of bed again the next day. Courage is not having any answers, but taking action anyway. Courage is opening your heart and mind to hope and possibility, despite crazy mind goblins telling you it's a terrible idea. Courage is agonizing over a decision for months or years, then making it on your own time when you're ready. Courage is listening to the whisper in your gut with such a fine quality of attention that it becomes a roar Courage is a hot mess, at least in my experience. What's that? Yours too? See, we're all more similar than you think, and we all have a much deeper well of courage than we realize. What would you do if you had the courage? What would it look like to even start without it? Deja vu again. How is it possible that my 2011 self had already figured all of this out? What am I even doing on this substack if she had all these answers 12 plus years ago? Unbelievable. Some people never learn. In June, somebody sent me an article from my hometown, blocks away from the first apartment we lived in after I was born. Reporter Gary Lef writes, the owner of the Hilton San Francisco, Union Square and Park 55 Hotels has chosen to stop making payments on $725 million in debt and turn the keys over to their lender, JP Morgan. Chase Park Hotels and Resorts says San Francisco is too much of a mess and won't be turned around anytime soon. If even the largest business owners in the country are declaring things too messy, tossing the keys and just walking away without even selling for scraps, no wonder some of us smaller fish are reeling. If you are still in business after these last few years, you are winning. You are a hot Best burger in the city. Lettuce flying grilled onion Double patty with cheese mushrooms spilling off the side Juicy summer tomatoes. Delicious mess. I'll take two.
I hope you enjoyed that essay from Rolling In Doe. That's just one of many I'm publishing twice a week on Wednesdays and Saturdays at 11:11am and if you want to read the full archives and get full posts in the future, I would love for you to join us, learn more and sign up@it's freetime.com secret or go straight there at rollingindo doh.substack.com that's itsfreetime.com secret or rollingindo doh.subStack.com you can also follow me directly on Substack. Even if you don't want to subscribe to any of my three publications, Pivot, Freetime or Rolling in Dough. You can just see what I'm reading, what I'm restacking, quotes that I like from other publications on Substack. That's something that I really appreciate, just the social and community element that they've created there. You can follow me directly on my profile page@substack.com jennyblake that's substack.com ennyblake and one of my favorite things about this platform is that you can see everything I'm creating across the Internet all in one place on that profile page. See you there.
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