When Your Business Hands 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: Sometimes

14:37 – 15:10
Jenny Blake: we can only laugh now. Yes. I don’t know there, you know this advice I wrote about this too Sorry to be a broken record. I just don’t want to repeat myself, but you know, oh just be yourself That’s the key to having a great podcast. I mean, kind of for some people, if you being yourself is what the market wants. But for other people, being yourself is just a very niche idea that not that many people want to listen to in the glut of shows that we have now, where you’re competing with really professional, well-produced celebrities

15:10 – 15:16
Jenny Blake: and comedians and TV shows and all kinds of even just audiobooks as a format.

15:16 – 15:49
Rochelle Moulton: Yeah, it is interesting. There’s a piece that no matter what we do that has to appeal to a market and then how you monetize that is going to make the difference between whether you can keep doing what you love and what you’re great at or whether you have to move on. But I’m curious about something. You were in the midst of this, and you’re putting out the rolling and dough pieces. How hard was it or is it to hit publish when you’re writing about some pretty difficult days? Or does it make it easier that you’re sharing?

15:49 – 15:53
Rochelle Moulton: I’m just curious and maybe whether that’s changed from when you first started doing it to now.

15:53 – 16:27
Jenny Blake: Yeah, it’s a little bit of both. The beginning felt really vulnerable and I had just a huge vulnerability hangover, especially because in the early days, it was the first time, I mean, I started a blog in 2007. And I used to be surprised by the fact that the more vulnerable posts in those days got the best feedback and the most traction. So that was something I had experienced, but I felt I had been trying to hold, I won’t even call it a mask. I had just been trying to put on a good face as a business

16:27 – 16:58
Jenny Blake: owner for 10 years. It felt really weird to say, and here’s the part that you don’t see, or here’s the part that’s really going on that you would have no idea about if I didn’t tell you. That was really vulnerable. And certain things that I was worried about an actual current or former client seeing, I would put behind the paywall. So that did help. But the part that’s been so rewarding is just hearing people’s comments and sometimes people don’t even write the comment publicly they text me or email me and say I really needed to hear

16:58 – 17:27
Jenny Blake: this today or I look forward to your posts every Wednesday and Saturday with my coffee at 11-11 and I don’t miss it. It’s like their twice weekly appointment. That keeps me going. And on days where I feel like I don’t have anything to say or I’ve had to dash together what I would consider a sloppy subpar post, but I put it live anyway because done is better than perfect. I think about those people who say, even if it’s 1 person who says, I’m waiting at 11 11 every Wednesday and Saturday, I don’t wanna let them down.

17:27 – 17:57
Jenny Blake: So it is vulnerable, both the content of what I’m sharing and how people might judge me, But it was also very vulnerable in the beginning and still is the quality of my writing, the craft. Just feeling like I’ll read a Pulitzer Prize winning novel and then go to write my own dough posts. And I’m like, ugh, what is this gap between the work that I enjoy reading and what I’m able to and capable of creating. The gap is so wide as Ira Glass talks about, the gap between taste and talent. And that continues to be vulnerable.

17:58 – 18:07
Jenny Blake: But so what? I have this mantra 5149. It’s like 49% vulnerable and self-criticism and 51% hit publish anyway.

18:08 – 18:43
Rochelle Moulton: Well, I mean, it’s interesting that you say this because I think we’re all this way about whatever we create. We just think it’s got to be more polished and we compare ourselves to other people. But what’s always interesting to me about your duh posts, and to do really a dope pose is that there’s always at least 1 gem. And Sometimes it’s the video of the chick on the skateboard going through the airport, completely oblivious. And other times it’s… The lulu is the lulu. I had not heard that. That’s how unhip I am. I had not heard

18:43 – 19:14
Rochelle Moulton: that. But I love that. And by the way, I keep that on replay whenever I’m in a certain mood, I play that. I love that. Or the 1 just today where you talked about the talisman that a friend gave you. So it’s important when you write for an audience to find a way to write for you and write for the audience. I feel like you found that balance. So how do you think about the evolution of your thinking over the last year? I mean, you’ve very publicly wrestled with the idea of quitting, whether that was quitting

19:14 – 19:26
Rochelle Moulton: your current business, giving up the podcast or giving up on New York for a different life. How did your thinking change and how were you making ends meet while you’re going through this process of deciding what’s next?

19:27 – 20:00
Jenny Blake: Yeah, it’s interesting because something like staying in New York, I just constantly say I’m hanging on by my pinky fingernail. I am like, in 1 of those Mission Impossible movies with a pinky dangling on the ledge, but so determined and desiring to stay in New York. And I do have doubts sometimes if I’m just being stubborn and I’m just not getting the memo that I need to leave But in a way, it feels like a known variable I want to be here and I am gonna fight to stay and I feel the same way about self-employment

20:00 – 20:32
Jenny Blake: I want to be here and I’m gonna fight to stay. I can’t imagine. I have no judgment about anybody working at a job but I get sick like 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 the known variables. And yet, as you said, it’s just so precarious and 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

20:32 – 21:02
Jenny Blake: 28 days from now. So where’s that going to come from? I have no clue. And I’m 13 and a half years into my business. So it’s also not a feeling that I’m not used to. I’ve kind of gotten used to some of this feeling of just constant uncertainty. But this is pretty strong. Like you mentioned the liminal space or the messy middle. This is the most prolonged messy middle that I have ever had in my life. It’s just lasting the longest. And I can only think of a Jalil Gibran quote that I love, which is, the

21:02 – 21:33
Jenny Blake: deeper the sorrow carves the more joy your cup can hold. That if this time of confusion is so prolonged it must be for a reason. It must be because I’m still carving the cup that holds the next part of my body of work or carving myself, my person, my identity. And the answers aren’t neat. I have some, sometimes I have some people really close to me who love me and want to be helpful. And I can tell from the way they respond to dope hosts, like, they’re like, can you just get over it already? You’re whining

21:33 – 21:57
Jenny Blake: or you’re, you seem stuck or here’s the way to think about it that would be more positive. And I get what they’re trying to say. Again, they just want me through it already because they’re uncomfortable, but I can’t rush the process. So I’m trying to be patient with the unknowns and then just hold on to the things I do know. But I think even those have to be out for grabs too. That’s the thing.

21:58 – 22:16
Rochelle Moulton: Yeah. And again, you’ve been public about this. You’ve turned 40. And that’s a time when we step back and start to think about, all right, what have we done so far? How much time do we have to do the next thing? What should that thing look like? I mean, it’s a very natural pause point for most of us.

22:16 – 22:47
Jenny Blake: Yeah, I mean turning any new decade and when I turned 40, I was tired. I wasn’t feeling, I was not happy on my 30th birthday. I was in the middle of what I called my apocalypse year. Up till now that was the worst year of my life was 2013 when I turned 30. And then turning 40, I was exhausted and frustrated. And the 1 thing that was working was rolling in dough. That’s where I felt the most alive. Everything else felt like it was a mess. I was 30 pounds overweight, none of my clothes fit in

22:47 – 23:18
Jenny Blake: my closet. And I mentioned that it reached this breaking point that sent me to the ER with Bell’s palsy where half my face was became paralyzed, that I just thought this isn’t working. And so that was 6 months into my 40th year. And now as I prepared to turn 41 in 9 days, I lost 30 pounds. I do prioritize the gym every day. I might not have any more money in the bank, though I did have, like I said, 1 licensing client renew, which was a huge win. But I am healthy. I fit my clothes again.

23:18 – 23:50
Jenny Blake: I can shop in my own closet. I feel vigorous. I have more energy. I just feel like I don’t know if my health hadn’t hit that breaking point at mid-year of turning the new decade. I might have done things in the wrong order. Like if the money had come in first before the ER, I doubt I would have changed any of the habits that were slowly eroding my energy. So it almost had to happen this way. I just keep hoping that the story ends with some kind of financial turnaround. Right. But even my writing coach told

23:50 – 24:02
Jenny Blake: me, you can’t rely on that. Like, there has to be an interchange. The money is the epilogue, not the point. Yes, exactly. Well, and Bob the neckthrob, which I

24:02 – 24:30
Rochelle Moulton: love that you gave your pain a name. Can you just tell us a little bit about the story? Because I found it really profound when I thought about it from beginning to end, which I think took place over maybe a couple of months of your of your substack where you’re on this very last leg well let me back up you had this two-month work sprint right yay after nothing and you’re on the very last leg of it you’re arriving in seattle what happens

24:31 – 25:05
Jenny Blake: yeah oh my gosh well let me preface this story by saying, friends new and old will say, oh, the cobbler has no shoes because I wrote this book, Free Time, that came out in 2022 about working with joy and ease and setting your own schedule. And this is different way of working. And part of what happened before this leading up to this in-person gig that I was facilitating in Seattle, I thought maybe I’m just being lazy. Maybe I’m wrong about free time and the values that I shared. And maybe I do need to bring some hustle

25:05 – 25:39
Jenny Blake: back. You know, hustle culture, we’ve been now denigrating for a decade. But I just thought maybe the problem is me. And I should just stop complaining about my finances and double down and just suck it up. And it basically threw a combination of me trying to do that and things randomly coming in. I got 3 speaking gigs each 3 weeks apart. I was launching VIP days to help people implement a Notion operations dashboard. I was doing boxer coaching. I was running an artist’s way book club. Everything hit at once. But I thought, well, maybe this is

25:39 – 26:13
Jenny Blake: how everyone else is working. And I’ve just been slacking off. So my self-talk was not great. And of course, during this 2 month sprint, I started to develop neck pain, shoulder pain. And metaphorically speaking, it’s like carrying too much, too much pressure, too much stress, too much work. But I had no choice. I had these in-person events I didn’t want to cancel. They were paying me the money I needed. It actually all went to a huge tax bill. Oh, lovely. But hey, it helped me pay the tax bill, yes. By the time I got to Seattle,

26:13 – 26:43
Jenny Blake: I was at the tail end. I had 1 week left. I had a half-day event that I was facilitating, a team-building thing for this instrument called Strengthscope. And then when I got back to New York, I would have a VIP day and an appearance at the Career Development Conference Board in New York. And then I could rest. So like it was a week away, the rest, but sure enough, I woke up the morning of the Seattle event and I was so nauseous, I couldn’t stand. I couldn’t even stand. I was writhing in pain all night. I

26:43 – 27:11
Jenny Blake: slept on the floor, even with my feet up on the bed. I was in so much searing pain, no amount of pain medication, at least over the counter is all I had at that time was working. I called my husband crying. I don’t know how I’m going to do this. I can’t even stand. And the deck isn’t finished. And the facilitator guy isn’t finished. And I need to somehow get to the printer, print the materials, and then sit in a room and facilitate for half an hour. I’m sorry, 3 and a half hours, not half an

27:11 – 27:42
Jenny Blake: hour, 3 and a half hours. And he said, well, can you cancel? No, they all flew in for this across the country. I just couldn’t cancel and I needed the money. And it wasn’t even 1 of my highest paying gigs. This was probably 12k, which for me was even included cost of travel, hotel, the assessments and so on. But I couldn’t imagine having to give that back. And so he opened his laptop, he wrote the facilitator guide as I dictated it to him from my hotel robe. And slowly but surely, I was able to get to

27:42 – 28:03
Jenny Blake: the event and essentially just fake it till I make it. Just pray that my body could like do me this solid and help me out. And that’s like really bad to my body, animal. But it cooperated. And I was able to do the event and it went really well. And I was able to do the other 2 and they went really well. And 2 days later, I woke up and half my face was paralyzed.

28:04 – 28:05
Rochelle Moulton: Yeah. The end result.

28:06 – 28:21
Jenny Blake: Yeah. And Michael thought I was having a stroke. He looked at me and he just said, that’s it. I just saw the worry wash over his face. And he’s like, that’s it. We’re going to the ER. Like no more me writhing around in pain every night hoping it’ll just go away on its own.

28:21 – 28:30
Rochelle Moulton: Well, and didn’t the ER think you were having a stroke too? Yes. Bell’s palsy does tend to look like a stroke to those of us without medical degrees.

28:30 – 29:03
Jenny Blake: Yeah. And I guess the pain, it got so inflamed, my muscles had gotten so tense that they pressed on a facial nerve. And I knew because I couldn’t purse my lips, I couldn’t put lip gloss on. Oh, it was terrible. And thank goodness, it was just Bell’s palsy. In fact, I just read a book called Smile by playwright Sarah Ruhl. She had it for 10 years. It didn’t go away. Thankfully, I got a steroid prescription and I joined the spa office 2 days later. Mine did go away in about a week. My face got back to

29:03 – 29:05
Jenny Blake: normal, but hers was 10 years.

29:06 – 29:08
Rochelle Moulton: Yeah, I had a client who it never went away.

29:09 – 29:09
Jenny Blake: Oh, man.

29:09 – 29:17
Rochelle Moulton: Yeah, yeah. So talk about a wake-up call, right? So it went 2 days from that to your spa office. Yeah, we just were fed.

29:17 – 29:53
Jenny Blake: We were like, this is unacceptable. Something is so broken. And the thing is, I’ve been an advocate for mind-body business for over 10 years. This is nothing I didn’t already know, that if you treat your body badly, it will pay. I will pay and I always joke my body has me on a short leash. Every time I work in a way that is not aligned, it yanks me back into place dramatically, whether it’s vertigo or losing my voice, the instrument, even now is a little scratching, Bell’s palsy. It’s like, that’s why I know in my heart

29:53 – 30:27
Jenny Blake: of hearts, probably getting a job. Yes. The leash would yank again. Like stop it. What are you doing? And so I knew better and still I let myself talk because I think part of what happens in the messy middle is insecurity. When things stay messy for a prolonged time, it’s hard to maintain confidence. It’s like if anyone had dating problems at any point as I did. Oh no. Yeah. It’s like, how long can you just say, oh, I’m a queen. I just haven’t met the right person. But then if somehow like everything goes south, you start

30:27 – 30:57
Jenny Blake: to wonder, is it me? And so I find with the prolonged messy middle, it’s really hard not to just say like, am I wrong? Are my ideas about myself or my way of working just wrong? And I think that is what this time around led me to the body wake up call. And yeah, it was unacceptable. And still now it was so dramatic. Really, you said turning 40 helped with this, and I feel it got me to really say no. Now I don’t even have the guilt. It’s just like, no, because in my head, I’m recalling,

30:57 – 31:13
Jenny Blake: do I want to go to the ER or do I want to say yes to this random virtual coffee? No, I don’t. I need to go to the spa office. I need to go to the gym. Like that actually has to be the priority as indulgent as it sounds, even to myself when I say it out loud.

31:13 – 31:26
Rochelle Moulton: So tell us about, you have a routine now with your spa office. So tell us about the routine because I feel like you’re going to be giving a permission slip to some women in particular who might feel the need for 1.

31:27 – 31:58
Jenny Blake: And I’ll be paying 1 forward because I just wrote about Ellen Hilderbrand who works out for 3 hours a day. And she also reciprocally gave me a permission slip, even though she doesn’t know I exist, but through me listening to her on podcasts. So my stack, I basically treat the Equinox that I joined as the office. So I leave the house by 10 a.m. After I take Ryder out. I try to, if I have to schedule calls, I try to get them on 1 day a week, maximum 2. But I go and here’s the stack and

31:58 – 32:29
Jenny Blake: I can do it in any order so I can kind of go with my energy. But ideally there’s some kind of cardio. So biking, rowing, running, swimming, maybe something like strength building, yoga or Pilates. Then there could be a writing sprint, 20 minutes, maybe an email sprint, 30 minutes, which I always resist. So I have to build it in and then reward myself. And then the spa part, sauna, steam room, shower, use their fancy products. I might even sit there. I pay for the extra tier where you get a private locker and 24 hour laundry service

32:30 – 33:00
Jenny Blake: worth every penny. And sometimes I’ll sit in the women’s executive locker issued robe, because that’s what they call that level, the women’s executive locker. And I’ll do my morning pages even if it’s afternoon. I might even make a cup of tea and sit and read something. And then I go home. So by the time I’m going home, it might be 4 or 5 hours later. But ideally, I’ve done a little bit of everything, and I come home a new person. I really do. And I might not be getting a huge volume of work done, but I

33:00 – 33:07
Jenny Blake: try to make sure I hit the really essential things on any given day. And it’s just made a world of difference.

33:07 – 33:16
Rochelle Moulton: What I love about this is you’ve been very open about this. And a lot of us do things like this that we don’t talk about. So I love that you did.

33:16 – 33:19
Jenny Blake: Wait, do you have 1? I want to know what your thing is.

33:19 – 33:53
Rochelle Moulton: I do. Well, I don’t have a spa office. Unfortunately, we were talking about that before the show. We do not have such a thing here. But I do do an extended workout. And some days I do strength and cardio. So when I do weights, I do like an hour’s worth and I stop in between and I check my emails or I post something on LinkedIn or I’m doing something related to work. And then when I’m on the cardio, that’s when I will read. And usually I’m reading, like I read free time on the elliptical machine in

33:53 – 34:26
Rochelle Moulton: a number of sitting. I love that. I did, I did. And so I might read a business-y philosophical book like that. Or this morning I read a piece of a novel. I was just in the mood for that. Activates a different part of our brain using our bodies to get more healthy. And I don’t know if you feel this too, but I love being around other people that are doing it too. And I love seeing all the different body shapes and styles. Like they’re, oh, we’re, humans are so intrinsically the same and different all in the

34:26 – 34:58
Rochelle Moulton: same time. So, you know, I don’t really talk about that very much, but I do work my schedule around that because it’s optimal for me. It delivers the best Rochelle, if you will, that I can deliver. And I know the older I get, the more important it is. Yes. So yeah, I don’t like giving that up for anybody. But what I loved about what you said in your in your sub stack was about the Hilder Babes. It was like a revelation that somebody at that level of success, she’s a New York Times best selling author, that

34:58 – 35:04
Rochelle Moulton: she works out 3 hours a day and still can produce, what is it, 2 books a year I think?

35:04 – 35:42
Jenny Blake: Yes, 1 and then for 7 of those years 2 a year, but she’s produced 29 novels and yet the 3 hours it’s non-negotiable, it’s every day And then in her writing window that happens afterwards, sometimes she says she gives herself 6 or 7 hours to write. I think she aims for 3 hours total of composition, but that might include reading by the pool, taking a nap, walking on the beach. So even her writing window is very creative and very flexible and very soul stirring. And I think as entrepreneurs, and if you do anything creative within the

35:42 – 36:14
Jenny Blake: business, our mind is 1 of our best assets. It is the way we think strategically and solve problems and have intuition and help our clients and be original. And like all the things we care about rely on this whole mind-body-spirit system being super high functioning. It’s just so easy. We’re all only human. There’s only so many hours in the day. It’s like it is easy to let it slide. And so I do love like you here. I love hearing your routines. I love hearing hers. And in my case, I also realized, all right, well, the old

36:14 – 36:28
Jenny Blake: way didn’t work. The old way just put me in the ER. So when I tried to even work the way I felt people would judge me, when I tried to be like everyone else and not be quote lazy, it just didn’t work. So I might as well try this new way.

36:28 – 36:40
Rochelle Moulton: We do hold ourselves to some impossible standards. I think particularly as Americans, it’s part of the culture that we’re supposed to work hard and at least look like we’re working hard.

36:40 – 37:14
Jenny Blake: Right. Right. Totally. And then I feel like what right do I have to complain? Some people have 3 jobs or are working at minimum wage. People have it so much harder than me. Some people don’t have a roof over their head at all or food to eat at all. I think that’s 1 of the harder parts of rolling in dough is it’s a little hard to… They’re very champagne problems when looked at at a global scale. So sometimes I get self-conscious to really have any complaint at all. So I just try to monitor that, but it’s

37:14 – 37:16
Jenny Blake: still my reality, I guess.

37:17 – 37:52
Rochelle Moulton: Well, yeah, I mean, that’s, that really is what it is. It depends on who your audience is. It depends on what you want to share and how you want to make that overlap and there are an infinite number of ways to reach those folks so I I mean I just found the process so fascinating because there’s nobody else I’m aware of in our kinds of spaces that has had a kind of a running diary of what’s going on, including injecting some humor. There’s some really funny bits in there. So I’m just curious, so where are you

37:52 – 38:08
Rochelle Moulton: on all of this today? I mean, what do you see, how do you see yourself morphing forward? And we won’t hold this to you because we understand this is still very much a work in progress. But I’m curious like where your thoughts are right now. I have little whispers. Could this be

38:08 – 38:39
Jenny Blake: a book? It would be my fourth. It would be a new genre, as you mentioned at the beginning. Part of me thinks it’s just too mundane. And You said like it’s like a diary. My friend calls it business reality TV and my husband called it sex in the city but for money, about money. So that makes me smile. Like I’ve gotten so much value. I love reality TV and I love Sex and the City. So if I can create these little snacks, and like you said, I do try to add value. I joked, I used to

38:39 – 39:11
Jenny Blake: ask people this question, if your work or your writing were a food, which 1 would it be? And mine’s a chopped salad, because I like giving lots of little treats in there, something for everybody. But as far as what’s next, I got really lucky by just landing a few pivot related, that’s kind of the corporate side of my business, pivot related things this quarter. I think I feel less resistant to doing those. Like I see that they pay the bills. And I don’t know because I have a lot this I did the artist way, but I

39:11 – 39:43
Jenny Blake: still have a lot of blocks that the thing that I have this energy around is writing. And yet every day you read and hear from people who say, writing, you will go broke. The media is dying. We’re in a media apocalypse. Writers don’t make money. Books don’t make money. Nobody buys books anymore, which isn’t true. But like, oh, I get so scared because it’s the thing that gives me the most energy, but I’m also maybe a little burned from the podcasting experiment where doubling down on what gave me energy didn’t work. So in that sense, I

39:43 – 39:52
Jenny Blake: don’t know, but I just keep trying to, I try to just keep going with the writing. So at least I’m not going to stop it, even if I don’t know what it looks like and how it fits into the larger business.

39:52 – 40:28
Rochelle Moulton: As I was listening to you, part of what struck me is that it’s a model that writers have used for millenniums, where you have a corporate benefactor, in this case, multiple ones, because you have that corporate side of your business that you’ve already developed that probably doesn’t require a lot of work, that probably doesn’t require a lot of staff. I mean, you’ve been doing this. And again, those are some pretty big assumptions. But that allows you the ability to then, and I’m going to use the word indulge, but that doesn’t mean it’s not like heartbreakingly important,

40:28 – 40:42
Rochelle Moulton: indulge in the ability to write without feeling like it has to bring you money. It could. I mean, we’ve got lots of examples of narrative and memoir style things that have made a ton of money, but

40:42 – 41:16
Jenny Blake: it does reduce your risk that way and still give you something that will fuel you. Yeah, it’s so interesting because I also then I’ll get insecure like, well, I wrote pivot 8 years ago. What if that just dries up? You know, it’s like, what if it just goes away or I’m just not relevant relating to that book anymore so long ago. It’s interesting because I can’t bring myself to double down on B2B outbound sales, or the things that I would really need to do. I do have an assistant and she is helping with some outreach to

41:16 – 41:46
Jenny Blake: previous clients. But yeah, it just has fears around it too, even though I agree. I think that model can work really well for me. And I do have a very lean team for this reason. I did cut my overhead. And I would say that is a very free timey thing, which was, as you said at the beginning, delightfully tiny team. Right now I just have 1 part-time assistant, and she’s so much more than an assistant, but that’s it. And I’m actually really happy. The smaller the team, the happier I am, just because I get more time

41:46 – 41:48
Jenny Blake: to myself, less admin.

41:48 – 42:23
Rochelle Moulton: Yeah, I really just can’t wait to see where you go with the writing. And I think the fears that you mentioned, I don’t want to put you off, but those will keep coming back. I mean, we all have fears about relevancy and it’s they come from having success with something. Yes. Right. Free time. It really pivot. Yeah. It was a huge success ball for you. Huge. And so it’s more time has passed. I mean, it’s natural to feel that way. I think it’s cyclical, whether you’re in the arts or whether you’re a soloist, that it’s hard

42:23 – 42:25
Rochelle Moulton: to get away from that cycle.

42:25 – 43:01
Jenny Blake: Yeah. And it’s interesting, at a much smaller scale than Elizabeth Gilbert, her first TED Talk was about the fact that she could never meet the success of ePray Love. Like there was probably nothing she was ever going to be able to do in her career that would achieve that kind of lightning in a bottle success. And that her Ted talk was her reconciling with that idea. And so again, on a much smaller scale, just to give listeners in a sense, my first book, Life After College, sold maybe 40, 000 copies across all formats. Target picked it

43:01 – 43:35
Jenny Blake: up for their end cap display. Pivot has sold maybe 60, 000 across all formats. And then Free Time, which published into a somewhat funny environment, 2022, and published independently, has sold about 7, 000. And That’s remarkable for any book. Most books don’t sell more than it is 3, 000 copies, but it’s so much less than the other 2 that it’s been really hard not to compare it. It’s like we wouldn’t want to compare our children to each other. I don’t have kids, but that doesn’t seem like a good idea. And yet here I am reconciling with

43:35 – 44:14
Jenny Blake: what feels like a downward trajectory. Having had so much, having the business earning at 1 point for me was a lot 700, 000 with no full-time team members, relatively passive-ish, let’s call it. Having the book pivot be so successful financially, sales-wise, Penguin Random House, and then having it all sort of feel like it’s on a down slide or a dough slide. That’s been interesting. So I’m trying not to be ungrateful with everything that’s gone on with free time. But it’s like in the shadow, it has to emerge from the shadow of these 2 prior successes that

44:14 – 44:23
Jenny Blake: seem to come so much easier somehow, even though I am still very fulfilled now in my life, even more broadly, much more so than probably the first 2 books.

44:24 – 44:55
Rochelle Moulton: Well, and it’s, you’ve also hit a total change in publishing. Yeah. You know, deals that are being made now look very different. There’s a lot more self-publishing. I mean, the times have changed. And I’m not saying that as though it’s an excuse or an answer, but it’s why it’s so hard, I think, sometimes to get clear on this, because there are things happening that have nothing to do with you. And then there are the changes in you and that includes our listeners, the changes in you and what floats your boat now is different than what floated

44:55 – 44:56
Rochelle Moulton: your boat 10 years ago.

44:57 – 45:29
Jenny Blake: Yeah. And then in terms of the change process, I love the saying, don’t push the river. It’s like, yeah, for me, what I like how so I’m adding to your what floats your boat metaphor, but you also can’t push the river like I change is so interesting because it cannot be forced. It’s like it’s happening. I love the real quick quote like something has entered. Life hasn’t forgotten you. It holds you in its hand but it’s like you don’t even know what it is yet. A sadness has entered the room. You don’t know what it is

45:29 – 46:03
Jenny Blake: but it’s sort of working itself upon you. The change. And that’s how I feel. That’s always how these moments feel. Cannot see through the fog, cannot see ahead. Even trying to answer your question, what’s next? No clue. I hope I can pay the mortgage. I’m a monk. And I hope I can get out of this, you know, precarious feeling situation. And I also try to remind myself that I might look back on this time and think, I had it so good. Or as my dad, if any day that you call my dad, he will say, these

46:03 – 46:18
Jenny Blake: are the great times. It doesn’t matter what is going on in the world, what’s going on in his life, these are the great times. He genuinely, genuinely means it. What a gift. I try to also remember, these are the great times.

46:18 – 46:45
Rochelle Moulton: I still want to call your dad Well, that’s just that’s super super helpful and insightful So I was debating whether or not to ask you this question because I asked you this last time. But I just wonder if maybe your answer would be different after the last year. And that’s, if you could go back to who you were when you first started your business, what’s the 1 thing you’d advise her to do?

46:45 – 47:22
Jenny Blake: Oh, that’s a great question. I would, well, I think the thing I did really well with Pivot was I had income streams that were scalable, recurring, and relatively passive. That was my magic 3 ingredients. And so things like licensing, things like a private community, even things like I put my coaching clients on a monthly retainer, where it would just they would get invoice on the first of every month, good until canceled, no minimum commitment, But I had gone off what they taught us at coach training, was there was project-based or time-based billing. So things like that

47:22 – 47:52
Jenny Blake: really saved my business in 2016 and beyond when Pivot launched. So if I could go back, I was really the bottleneck in the early days. I would say you got to get yourself out of the way. Like I say in free time, are you ready for your big break or would your business break? And I know, Rusell, you’ve been so great about talking about scale and systems on your show. But I’d be trying to think about that from day 1. How do you not make it fragile by being the bottleneck, being in the way? And how

47:52 – 48:09
Jenny Blake: can you design income streams, I would say at the intersection of revenue joy and ease, which for me includes scalable, recurring, and ideally semi-passive. Meaning it’s not just 1 for 1 on your time, but that’s something you’ve talked about at great length and wonderful length.

48:09 – 48:23
Rochelle Moulton: Oh, we all need that. Yes. We need more of that. So Jenny, we will be putting all sorts of links to you and your content in the show notes, but where’s the best place for people to learn more about you?

48:24 – 48:56
Jenny Blake: Well, in fact, I’ll give you 1 more addendum to the previous question. I had sessions with a coach via Voxer that now it’s my favorite way to do coaching, which is asynchronous. So I’m doing fall Voxer coaching. I do it in the summer. Nothing scheduled, nothing on the calendar at all. And yet it has worked so well as a format for me and for my clients. So maybe this can also be a permission slip. You can get quite creative. Like it is possible to do coaching or advisory and not have anything on your calendar. What could

48:56 – 49:26
Jenny Blake: that look like? For me, that was a Voxer coaching, a weekly AMA, ask me anything. But these examples are out there. Even VIP days can be a lot of revenue in 1 day. Really fun. You get to treat your client like royalty before, during, and after. So there, I just want to say like these things are out there and I’m saying it to myself as well. Keep looking for them. If you want to find me, you can find me at itsfreetime.com. That’s the main website for this body of work around free time. And then on Substack,

49:27 – 49:34
Jenny Blake: it’s rollinganddoh.substack.com. And go there. That’s what I did after we

49:34 – 49:55
Rochelle Moulton: talked the first time. It’s been great to watch your journey. And Jenny, just thank you so much. I wasn’t sure what you would say when I invited you back to talk about this. I wanted our listeners to hear this story, this messy middle. So I just so appreciate your willingness to come and talk about this. Thank you.

49:55 – 50:25
Jenny Blake: Well, thank you so much for having me, Rochelle. And really to anybody listening, if you’re going through it and you feel like your business is falling apart or your client pipeline is totally dried up and gone, you are not alone. Every week a friend calls me and I say it might be selection bias because I’m the 1 writing, rolling in dough, but every week someone calls me thinking their business is like going to go belly up. And I say to them, you’re not alone. You’re not the only 1 because I’m the 1 receiving all these calls

50:26 – 50:43
Jenny Blake: from such competent, bright people. So I’m so grateful, Rochelle, for you to have interest in this of when your business gives you lemons. And as I said before we record, like we may not have made a lemon drop martini yet, but we’re certainly making the lemonade through.

50:43 – 50:46
Rochelle Moulton: I feel like the shaker is going, you know?

50:46 – 51:02
Jenny Blake: That’s it. Yeah, we got the shaker. We’re at least squeezing some juice out through this. So thank you for giving this opportunity and for following along. It means so much. And that meant so much from the day you reached out. Thank you. And big thanks to everybody who’s here listening. Well, thank you, Jennie. So as

51:02 – 51:18
Rochelle Moulton: we wrap up this episode, if you haven’t joined my email list yet, now is the time. Your soloist business and your future self will thank you. The link is in the show notes. That’s it for this episode. Please join us next time for the soloist life. Bye bye.