When Your Business Gives You Lemons with Jenny Blake

When you’re in the midst of an overwhelming business challenge—your revenue plummets, your audience dries up, you can’t seem to make a sale—what do you do?

Award-winning author and podcaster Jenny Blake takes us through the messy middle, sharing her story of challenge, resilience and percolating without yet knowing the answer:

Why her first reaction to a pandemic-induced 80% revenue drop was “I wrote a book called Pivot—I’ve got this.”

How that reaction turned to “I couldn’t fake it anymore—I couldn’t pretend anymore. I didn’t have any hope left…” when she lost a six-figure client.

Channeling her angst and uncertainty into a popular (paid) substack as she semi-publicly worked through what to do next.

The health scare that made her dramatically change how she was working.

The glimmers of her next chapter—how they appeared and how she thoughtfully nurtures them.

LINKS

Jenny Blake Substack | Free Time | LinkedIn | Twitter | Instagram  

Rochelle Moulton Email List | LinkedIn | Twitter | Instagram

BIO

Jenny is an author and podcaster who runs a Delightfully Tiny media company. She is the author of three award-winning books, including Free Time (Ideapress, 2022) and Pivot (Penguin/Random House, 2016). She hosts two podcasts with over two million downloads combined: the Webby-nominated Free Time for Heart-Based Business owners, and Pivot with Jenny Blake for navigating change.

On her Substack Rolling in Doh, she shares personal essays about the messier parts of running a small business.

She lives in New York City with her husband and her angel-in-fur-coat German shepherd Ryder.

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TRANSCRIPT

00:00 - 00:30

Jenny Blake: I have no judgment about anybody working at a job, but I get sick with that kind of work schedule or the meetings and calls. It drains me of all life, all the creative juice I have. It's just not the format. I've known that about myself. These are kind of the known variables. And yet, as you said, it's just so precarious. It's so touch and go. Even now, we're recording at the start of a month and I don't have the mortgage in the bank for 28 days from now. So where's that going to come from? I have

00:30 - 00:30

Jenny Blake: no clue.

00:36 - 01:16

Rochelle Moulton: Hello, hello. Welcome to the Soloist Life podcast, where we're all about turning your expertise into wealth and impact. I'm Rochelle Moulton, and today I'm thrilled to welcome back Jenny Blake to talk about what's been happening since we last spoke and spoiler alert, business has been challenging. Jenny is an author and podcaster who runs a delightfully tiny media company. She is the author of 3 award-winning books, including Free Time and Pivot. She hosts 2 podcasts with over 2 million downloads combined. The Webby nominated Free Time for heart-based business owners and Pivot with Jenny Blake for navigating change.

01:16 - 01:33

Rochelle Moulton: On her sub stack, Rolling in Dough, she shares personal essays about the messier parts of running a small business. She lives in New York City with her husband and her adorable angel in fur coat, German Shepherd rider. Jenny, welcome back. Yay, thank you, Russel. I'm thrilled to

01:33 - 01:34

Jenny Blake: be here.

01:34 - 02:08

Rochelle Moulton: I'm just so excited about this, as you know, from our pre-chat. So 1 of the reasons I wanted to have you back on the show is that last time we talked, you mentioned a big event. Well, 2 events, really. 2 big events that wiped $150, 000 of ongoing revenue off the table in a week. And that was the impetus for starting your Substack Rolling in Dough, where you've been documenting the not so lovely underbelly of owning a solo business when things go sideways. And I've been reading it since we talked almost a year ago. And now

02:08 - 02:13

Rochelle Moulton: today, I'd love for you to lift the veil a bit for our audience. So are you ready?

02:13 - 02:15

Jenny Blake: Sure. Yes.

02:15 - 02:15

Rochelle Moulton: And

02:15 - 02:22

Jenny Blake: We should say it's rolling in dough, D-O-H with a face palm for the O. I'm trying to tell my subconscious.

02:23 - 02:24

Rochelle Moulton: I always want to call it duh.

02:24 - 03:02

Jenny Blake: Yeah, right, which could work too. I want my subconscious to think that we're rolling in dough, And then the funny part is celebrating the dough, you know, the Homer Simpson of it all. And my husband made fun of me that I'm becoming a scholar in flop eras. And I'm like so interested in this topic of failure or when things go wrong or they're embarrassing or just the dough of it all. So it's actually become quite a fruitful area to dig into once I get over, you know, whatever embarrassment or fear that I'm self-sabotaging by sharing what

03:02 - 03:03

Jenny Blake: I do out loud.

03:04 - 03:15

Rochelle Moulton: Well, the other thing I should mention is 1 of the visuals for this is a beautiful donut with pink frosting and sprinkles. So I really, I love that juxtaposition of the duh with,

03:15 - 03:45

Jenny Blake: yeah, he's the little mascot. He has 2 eyes looking on a shifty. I have a lot of fun in Canva figuring out where to put him like on the beach or yeah, just different scenes. So thank you. Thank you for reading. And it's really a joy to be doing this project. I didn't even know that it would be lasting over a year, but also to get to talk about some of this out loud because part of the reason I started Rolling in Dough is I couldn't stand it anymore. I felt like every business book I read,

03:45 - 04:15

Jenny Blake: every business podcast I was listening to was all about the shiny and the successful and how to be more successful and how to earn 7 figures and now 8 figures and now you're a billion dollar creator. And yet behind the scenes, every phone call that I was having one-on-one with small business owners like myself, people were struggling. They were feeling like something's wrong with them. They were feeling like after 10, 15, 40 years that it was their worst year in business and that it was all about to collapse at any moment. For me, part of the

04:15 - 04:20

Jenny Blake: motivation here is, somebody's got to say this out loud. It might as well be me.

04:20 - 04:40

Rochelle Moulton: Yes. Part of me wants to say welcome to being a soloist. It's the ups and downs. Everybody has them, but very few people really talk about it until after they're through on the other side and then we can look back and we can pat ourselves on the back for how brilliant we are now, but we forget about how badly it sucked then.

04:40 - 05:13

Jenny Blake: Right. There are very real concerns. You wouldn't want to be a Debbie Downer or drive all your clients away by complaining, or seem ungrateful, or just seem like you don't have your stuff together. You know, like there are risks and the writing adage right from the scar, not the wound, why say dough is the wound? And I'm not saying that I advise everybody to do that. And I do lean more now toward the creative part of my identity than even the business owner part of my identity. So it's okay in a sense that I'm playing with

05:13 - 05:43

Jenny Blake: my play dough of my sub stack. So it's not that I would recommend everybody write from the wound, but I also feel like sometimes when you write from the scar, you forget the details. You forget what it's really like. It is a little shiny. We all know a scar. It's kind of like, Oh, isn't that beautiful? It just reminds me about the time I fell face first in the grass. OK, but in the moment, how did it feel? And I think it's easy to forget. So this is me also putting myself on a limb to say,

05:43 - 05:52

Jenny Blake: I haven't solved this yet. Even I get self-conscious coming to this conversation thinking, gosh, do I have anything new to share? I haven't figured anything out really.

05:52 - 06:22

Rochelle Moulton: And that's what to me was so interesting because you're in the messy middle and I love the messy middle. Now, having said that, And I'm sure we'll get there as we talk about this as an observer just reading what you've written I feel the change I can feel the next direction Especially with the 1 that you just sent this morning. Thank you. We should start with a little background Right. So talk us through where you were with your business when you got whacked with that $150, 000 loss.

06:23 - 06:54

Jenny Blake: Yeah. Well, the first whack was with everyone else March 2020 that's when 80% of my income was wiped out at once because I do a lot of speaking and events and corporate licensing from the pivot IP part of my business. And I was at that point, a decade into solopreneurship, I had a lot of fear. I used to work at Google, I had so much fear leaving that I wasn't cut out for entrepreneurship. I was just, I was a good employee. I was a good girl, a straight A student, but I didn't know how to make

06:54 - 07:23

Jenny Blake: it on my own. But I didn't dream to have the fears that all my income would get wiped out at the same time, all clients at once, and 2 years into the future. That I never saw coming. That was a worst case scenario I couldn't even imagine. I thought about recession, and I actually wrote my second book, Pivot, to be countercyclical in the sense that, OK, if there's a recession, pivot is still relevant. More people will be pivoting and getting pivoted than ever, which of course was also true in 2020. And I felt in that moment

07:23 - 07:50

Jenny Blake: when the pandemic hit, okay, I wrote a book called Pivot, I've got this. Now's the time, I doubled down on my podcast, I did a daily show for 3 months, I was like, really leaned on my reserves to be resilient and positive and optimistic and hopeful and grateful and all the things, even though it was such a tough time. And I'm the breadwinner for our household. So for me, my husband and our dog living in New York City with a mortgage that I had just bought this apartment a year prior. So my business had been at

07:50 - 08:20

Jenny Blake: a peak in 2019, the highest revenue I had ever had. I had just gotten married. We just brought home a puppy and I had just bought a house. Now maybe to my future self, I would say, can you please not do all those things at the same time ever again? But that's what I was carrying by the time at the same time all my income got wiped out. And I'm not trying to be a victim about it. It's just like this was the facts. Like the complexity of my life ramped all the way up, the pressure,

08:20 - 08:54

Jenny Blake: the stress, as the financial floor fell out. And for a few years, I was able to feel resilient and I even doubled down on my love for small business by leading into free time, launching a podcast, hybrid publishing the book, Free Time, that came out in March of 2022. But then things just didn't get better. I felt like the economy still was just inching along and there was this saying in real estate, survive till 25. And I kept thinking each next year things would turn around again and we'd go back to normal somehow but every year

08:54 - 09:28

Jenny Blake: got worse there were all these tech layoffs I work with a lot of tech companies it was the year of austerity the year of efficiency the year of cuts and layoffs and sure enough by last summer June 2023 1 of my biggest most favorite long time licensing clients ended our contract. And at that point, I felt it was the straw that broke the camel's back of my psyche. I couldn't fake it anymore. I couldn't pretend anymore. I didn't have any more hope left. And it's not that I'm trying to put all my identity into this 1

09:28 - 09:57

Jenny Blake: client, but hinted at it rhymes with Google and I used to work there. And I just thought, who even am I as a business owner without this client anymore? This was the thing that would impress my peers when I told them who my clients were. And I still have 1 licensing client who's been with me 8 years, but at that point I didn't know what else to do. And when I got that call and I processed the only way I could see to deal with yet another loss, yet another sort of devastating financial blow was to

09:57 - 09:59

Jenny Blake: start writing. And I haven't stopped since.

10:00 - 10:33

Rochelle Moulton: I mean, I so feel that, what that's like. You have this event that no 1 could have predicted, right? I could feel your optimism. I can do this. I'm going to do this. And then at some point, you know, there is a straw. But I guess what I'd like to talk a little bit about what I guess we could call personal narrative writing, which is, you know, what I think of as the substack. And so you dived into this new to you form of writing on substack. You're a great writer. I mean, I loved your book.

10:33 - 10:51

Rochelle Moulton: So that's why I was so intrigued by the substacks. And then eventually you also paused both podcasts, which, you know, by the way, sounded like a hellish production schedule to begin with. So it's been what, a year plus of regular substack pieces and 6 months roughly off of your podcast. Like, what's

10:51 - 11:24

Jenny Blake: that been like for you? Yeah, the pausing the podcast was a tough decision because I had had a show for almost 9 years. Pivot podcast was around for the longest since 2015, and then Free Time had been going for 3 years. And yes, the production schedule was intense. I published 14 episodes a month. However, it was the thing I loved. And if you've read Doe or Shall You Know, the post, do what you love and the money will follow if you meet these 20 criteria. I think 1 of my sort of veil lifted on the myths

11:24 - 11:55

Jenny Blake: and promises of entrepreneurship was if I just find the thing I love, I can make a job for myself even within my business. And that's what I tried to do with podcasting the last few years. And it was costing much more than I was making. So I was spending about 3, 000 a month on production and certainly wasn't earning that back because the shows didn't get big enough to have ad revenue that would have even broken even. And without regular speaking gigs, because in-person events, I mean, for me personally, still haven't fully come back the way

11:55 - 12:34

Jenny Blake: they were. I just couldn't float. It was almost like my corporate work was providing the funding for my passion projects, even within my own business. So I couldn't justify the cost anymore. I also felt I couldn't justify the time and energy. It wasn't just the cost, It was that here I am giving everything I have to this thing that I do love and I was really loving making the relationships and meeting people like you, but it wasn't sustaining me. It wasn't giving back to me. I mean, I love the love notes from listeners, so honored the

12:34 - 13:03

Jenny Blake: people for whom it was their number 1 show and Spotify wrapped. But I also had to look in the mirror and say this thing didn't work. It didn't take off. It's not sustaining me. It's actually putting my finances more at risk. So I need to take a break because it's trying to tell me through my bank account, something's not working. At least that's what my broader business is trying to say. Whatever you're doing with your time, it's not working because the bank account is in serious trouble. And pausing them in February, as you read in Dover

13:03 - 13:31

Jenny Blake: Shell, I ended up getting a surge of work in the spring. And I was able to run around doing a few speaking gigs. I was doing a lot. But I ended up in the ER. And then I spent the summer going to the gym every day. I joke that I joined Equinox and I call it my spa office, because I go and I do some work, some writing, some working out, some sauna and steam room. And I realized in hindsight now, looking back, I wouldn't have been able to focus on my health like that and my

13:31 - 13:50

Jenny Blake: recovery if I was still doing the podcasts because they were all consuming. It was filling my time every day. And now I'm really unhooked from the computer and the calendar and much happier, even though again, I haven't really solved anything yet. But I know what I need to kind of leave on pause for the moment.

13:50 - 14:02

Rochelle Moulton: Well, it's interesting when you mentioned the bank account, I know you were talking about money, but it also struck me that you have an emotional bank account and that was getting empty too, in part from the podcast.

14:02 - 14:34

Jenny Blake: Yeah, or I was just dedicating so much time and energy. The weird thing about it is that it never drained me. That's what was so confusing is that every day I really enjoyed interviewing my guests and being interviewed as other people's guests. That never really wavered. So that's what I found confusing in the decision to pause them was that I thought if you find that thing that gives you energy and lights you up and that you love and that People seem to think you're good at like that's it and then it takes off and it works

14:36 - 14:37

Rochelle Moulton:...