😬 On Moving Through Vulnerability Hangovers — Preview of October Bonus for Paying Subscribers
8 Dec 2025 · 3 min
Jenny Blake talks about vulnerability hangovers: that awkward feeling after you've shared something real, especially while running a business. She shares her own experiences and how to move through them, plus answers from her community.
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From the scar, not the wound. But what do you do when you feel called to write from within the wound?
Do you forge ahead knowing you'll wake up the next day with a raging vulnerability hangover? Or do you keep it bottled up inside for a future sell by date? Some future self who has things all figured out? There is no one answer to this, but the number one question and comment that I've been getting in the last few weeks is is about vulnerability. And I've been so moved by all of you who have said thank you for being vulnerable or you showing up in a vulnerable way on Rolling In Dough has really helped me realize I'm not alone. I'm not crazy. I'm not the only one having a hard time. I have a listener question from Scott that I'll also get into, but I'm really excited to record this bonus episode for you today to share how I move through vulnerability hangovers. I do not presume to know or be the end all be all source on vulnerability, you know, but being fresh in it and challenging myself and trying to stretch myself in this way, especially starting this summer, I feel like I can just share truth while it's fresh. So thank you for being here and if you're listening to a free preview, I encourage you to join us in the BFF community. We have a blast over there. It's a handful of heart based business owners. I would say at any given time 20 to 30 are super active and we probably have 60 to 70 members. I always welcome Lurkers. You'll love it. We have a Circle community. We meet monthly for a Q and A call with hot seats. We meet the following week optionally for anybody who wants to do small group breakouts to talk about a question or challenge in your business. So if you want to have a sense of community and camaraderie and and you're not alone in trying to figure things out, getting input and feedback where it's helpful and giving as much as you receive, check it out. You'll get 15% off your annual membership by joining Free Time at the founding member tier, which is bff. With that, let's get into it.
But I'll read a question from Scott, who specifically emailed in about this. He said, I'd love to hear you talk about seeking recognition or validation from others. Yep, kind of personal, so a bit vulnerable and private sharing it here in direct email, but I do wonder if it's something that lies beneath the surface for me. Maybe why I'm sending you the link in my reply possibly combined with an uncertainty about taking a step out of the corporate path about five years ago to go into full time sports coaching and having a lot of pondering about that decision, especially based on financial implications that came with it. Somebody tell me I'm doing the right thing, doing well, pack on the back kind of chat would be amazing. Thank you so much Scott for this great question. And who among us does not secretly, especially when you run your own business, want a pat on the back? Somebody to say, as my friend MBS puts in his email signature, you're awesome and you're doing great. And why does he have that in his signature? Probably because he knows we all need a pep talk every day with every email. When you're running your own business, especially when you've left a lucrative corporate job behind, there are so many moments of feeling vulnerable and out on the limb. And I know for myself as a business owner, I'm making so many decisions every day in the business, I don't know if I'm doing the right ones. I try to tune into my own intuition, I try to ask friends for input and advice and I read books and I listen to podcasts and I try to make the most educated, strategic choices that I can. But none of us know if we're doing it right or if we're making the right decision or if we're setting ourselves up for success or for more drama. And it's been really tough the last few years. So anybody who has started a business either post Pandemic within the last few years or even having started in your case, Scott, just two years before the pandemic hit. That's a really tricky time and a very, very turbulent time to be sailing the free time seas, to be running a small business. It is vulnerable to send in a question to a perfect stranger. I don't often have the courage to do that. I have to muster the courage to post comments to people I don't know in substack or participate in a chat or sign onto a zoom with groups I don't know, let alone airing out the things that I find difficult. So I want to say pat on the back and kudos for submitting a question at all. That can be intimidating. So I really give all of you kudos for being here and just showing up and showing up in your business every single day. It's vulnerable to run your business. It is vulnerable to make decisions. It is vulnerable to talk about the good, the bad and the ugly in public out loud to anybody, even your good friends, even your family. Sometimes our families are the ones who have the most concern for our security, and their number one goal for us is to be safe or financially stable. But we know we probably wouldn't be in the business of running our own business if we didn't want to take some risks and bet on ourselves in some way or another. And I find that to be incredibly vulnerable. Now, I know a lot of you have also asked about Rolling In Dough and are kind of taking that under consideration. As far as your own newsletters, several of you said on one of our brilliant Sparter calls that it's inspiring you to maybe want to be more vulnerable. What's that like? And kind of wondering and being curious about it. And so that's why today I want to share what helps me get through the vulnerability hangover. Because oh boy, have they been so strong. This year. Especially since I launched Rolling In Dough.
The first thing that helps me is questioning assumptions that I'm making about what will happen, usually the worst case scenario if I'm vulnerable, if I put something out there. So I share more about this in free time, episode 230, where I talk about the relationship between quantity and quality of creative work, and that it's not always what you think. But I have found in almost two decades of writing publicly online that the posts I'm the most vulnerable and unsure about are the ones that are consistently the most popular. It's this wild formula when I take a risk to put myself out there to do something that I feel very unsure about, legitimately unsure in the moment if it's a good idea or not. Those will get the best response. Even in my three books. At the beginning, in the introduction, there's the more personal part of my story, just to give readers context and without fail, in book signing lines and when readers write in saying they just finished the book, those are the bits that they reference. Yes, the tips and tools and the pivot method and the free time framework. That's helpful too. But it's the vulnerable parts of the story that people really connect to. So I do see part of vulnerability as building a muscle. It just takes practice and the more you do it, the more you get Real feedback from the outside world about what's resonating that's motivating in and of itself. That said, even when I know something may resonate, I don't ever know for sure. I'm just taking a wild guess. That's part of the vulnerability as well. There's sometimes still a hangover. I talked about this with the episodes I did with Adrian on the Pivot podcast on Parts Psychology, because in the first part of that, he was doing real time coaching with me, and we were exploring different parts of myself, and it was so vulnerable to talk about them, explore them. But even more so, when we hung up from recording, I started to get very nervous. Did I say the wrong thing? Am I gonna make somebody mad? Should I edit this one line out? Should I take that episode down altogether? Am I. Am I just gonna sound whiny? I mean, the flood of questions and concerns and worries was completely overwhelming. I genuinely wondered if I should take the episode down or if I should make those edits. Something stopped me from doing that. And I think the something is, again, that 5149 of just how can I take some safe risks? I'm not gonna say burn it all down, put people on blast, that I would be mortified if that kind of, like, went out publicly. Sometimes I'll imagine, if I do something and it was on the front page of the New York Times or the Wall Street Journal, would I regret it? Or if my grandma found out, would I regret it? Like, I don't ever want to speak ill of people if I can help it, or gossip. But when it's vulnerability about my own story and I'm speaking from a place of truth, I try to detach from the part of me that is so worried of what other people will think, because that pattern in my life has been a very heavy weight way to live. It is exhausting trying to please everybody because we all know that that's not possible. It's exhausting trying to project any sort of image. I've long since given up on trying to project an image of perfection, but trying to pretend like everything's always okay. Now there is part of me that I do like to be optimistic and I do want to put high vibration stuff out into the world. And I don't want to just get on the mic and complain and vent. That's really not my jam. That's not who I am at my core either. That's not my home frequency either, as Penny Pierce would say. But when things are tough, I think we do a disservice to ourself and to others to pretend otherwise. So part of what helps me press ahead, push, publish, not over edit things, not over worry about things, is taking the chance that if what I shared is helpful to one other person, maybe two, maybe a handful, maybe more, it ends up being worth it. And so I try to in the midst of the vulnerability hangover, which by the way happens after I record and again after the episode goes live. It's incredibly nerve wracking on the day where an episode like that goes live or a DOE post goes live, all the thoughts rush in. When Freetime was about to launch, I'll put the episode in the show notes 11th hour gremlins just genuinely wondering is this a pile of garbage that I'm about to turn over to the printer? Just sometimes I think that the stakes are so high we're not going to be the best judge of our work in that moment. And if the work isn't perfect, so what, is it still helpful? Probably. Is it still the best you could do at the time? Yes, probably. That's another thing that I try to fall back on, consistently putting things out over time, taking risks to share what I can in service of others. That's really important and knowing that no one thing is perfect. So I get very self conscious the day things go live of is it good enough? Is it horrible? I don't know. I'm not a good judge of it. And I'm not that interested in nitpicking any one piece of content, or let's just call it creative output, a podcast episode or an article nitpicking it into oblivion. My friend Melanie wrote a post early on in her substack, an Accidental Sabbatical about not babysitting her writing, and she pulled a quote from Elizabeth Gilbert, but her phrase has stuck with me. Mel's phrase of don't babysit the work. Yes, it's hard and it's cringey. It's cringey sometimes when it goes live and it's cringy when you look at it, and it's cringey when you feel you did something wrong. But nonetheless, don't babysit the work. Let it go. Keep moving. Because this is about the long arc of creativity. I have to remind myself that with Rolling In Dough, sometimes the essays, they're not where I want them to be. But I would rather stick to my schedule currently not badgering myself into a schedule, but I would rather stick to my twice a week schedule purely for the express reason that it gets me to drop the perfectionism, but I just remind myself, okay, one week at a time, one essay at a time. And having more at bats takes the pressure off of anyone.
If you're listening to a free preview, I encourage you to join us in the BFF community. You'll get 15% off your annual membership by joining Free Time at the founding member tier, which is bff.
More from Jenny
215: Stay Relevant, Sense What's Next, and Solve Difficult Problems with Stephen Shapiro
12: Belly of the Pivot Beast: On Bouncing Back from Zero with Adam Chaloeicheep
218: We've Gone Over-Bored (Part 2) with Michael Karsouny (Listen at Your Own Risk!)