How can we earn twice as much in half the time, with joy and ease, while serving the highest good? That’s the fundamental question award-winning author and podcaster Jenny Blake set out to answer in both her business and her now classic book “Free Time: Lose the Busywork, Love Your Business”.

Jenny shares some candid insights:

The thrills and challenges of moving from a rollercoaster life (high pressure, fast paced) to one of joy and ease.

What can happen when you remove yourself as the bottleneck in your business (hint: there are a lot of zeros involved).

Why she started a pay wall with her new content Rolling in D🤦🏻‍♀️h (and the value of continuing to experiment with your business model).

The low-stress, frictionless way to design your own workable systems—even if you suck at systems.

How to encourage non-linear breakthroughs vs. the “up and to the right” thinking that business owners are often encouraged to follow.

LINKS

Jenny Blake Substack | LinkedIn | Twitter | Instagram

Rochelle Moulton Email List | LinkedIn | Twitter | Instagram

BIO

Jenny Blake is a podcaster, Substacker, and the author of three award-winning books, including Life After College (2011), Pivot: The Only Move That Matters Is Your Next One (2016) and Free Time: Lose the Busywork, Love Your Business (2022). Her latest project is Rolling in D🤦🏻‍♀️h: Divine Disaster Diaries from a Breadwinning Business Owner Living in New York City.

She has two podcasts with over two million downloads combined: in 2015 she launched Pivot with Jenny Blake for navigating change (in the top 1% of podcasts), and in 2021 she added the Webby-nominated Free Time with Jenny Blake to set your time free through smarter systems (top 2.5%).

Jenny is a lifelong bookworm and aims to work ~10-20 hours each week, leaving plenty of time to take her angel-in-fur-coat German shepherd Ryder to the park to play with sticks on their favorite grass-covered hill every afternoon. She lives in New York City with her husband Michael, a contemporary fine artist.

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TRANSCRIPTS

00:00 - 00:22

Jenny Blake: Say no to sailing the sea of shiny shoulds. Everybody says now, oh, you should be on YouTube if you're a podcaster, you definitely should be on social media. I don't do any of it. I don't want to. I will stop doing the thing altogether. And I think you just learn that about yourself, what you can really say no to. So you funnel your best energy into the thing that you're uniquely skilled at.

00:28 - 01:10

Rochelle Moulton: Hello, hello. Welcome to Soloist Women, where we're all about turning your expertise into wealth and impact. I'm Rochelle Moulton and today I am so excited to welcome Jenny Blake. She's the author of 3 award-winning books, including my absolute favorite, free time, lose the busy work, love your business. And she has 2 podcasts with over 2 million downloads, 1 in the top 1% of all podcasts and the other in the top 2.5%. And a fascinating new substack on rolling in dough. All of that plus, and I quote, she aims to work 10 to 20 hours each week,

01:10 - 01:22

Rochelle Moulton: leaving plenty of time to take her angel in fur coat, German Shepherd rider to the park to play with sticks on their favorite grass covered hill every afternoon. Jenny, welcome.

01:23 - 01:29

Jenny Blake: Thank you so much, Rochelle. You included the favorite bit from my bio, which most people leave out. It's hanging out at the hill every day.

01:29 - 01:38

Rochelle Moulton: I'm sorry. Ryder has captured my attention. I've watched a couple of your short videos of him with the hose and yeah, Ryder's my guy.

01:39 - 01:52

Jenny Blake: Thank you. That's so sweet. Well, I guess having a dog is kind of a forcing function to take better care of even ourselves. Yeah. Food, water, exercise, grass and dirt. That's what he's brought into my life.

01:53 - 02:23

Rochelle Moulton: So 1 of the reasons that I knew we had to talk is the way that you describe free time in your podcast introduction. You say, how can we earn twice as much in half the time with joy and ease while serving the highest good? So let's start with how did you come to adopt that worldview? I mean, I know you're a Google alum, So I kind of imagine you were used to riding the roller coaster, right? High pressure, fast-paced environments. Like, what changed for you?

02:24 - 02:53

Jenny Blake: I started working at Google in 2006 when there were 6, 000 employees. And by the time I left, 5 and a half years later, it had grown to 36, 000. And I was working on really exciting global drop-in coaching programs. Life was good. And yet, I was feeling like so much of my time was spent in meetings and answering emails, that I was probably doing the work that I was uniquely qualified to do and that I most enjoyed 10 to 20 percent of any given day or week. And all the meanwhile I had been blogging so

02:53 - 03:21

Jenny Blake: I set up my first website Life After College in 2005 and this was kind of my side hustle but just as that phrase and that concept was getting off the ground. So what was happening is that at some point, I knew that I couldn't juggle both of those things any longer because I was hitting burnout. I would just burn out, crash, recover, burn out, crash, recover. My blog became a book. I got the book deal in 2010. And so right as it was launching, I was taking a sabbatical to start. I didn't think I was going

03:21 - 03:51

Jenny Blake: to leave. I was completely overcome with financial anxiety. I had been 1 of those kids that saves their birthday money. Like I was annoyed about money and really obsessed with having enough. And I just was so afraid, well, what if I leave Google? And then I end up in a van down by the river. Now it sounds cliche. Now it's a dime a dozen. Oh, why I left my six-figure job to start my own company. That's getting a lot of coverage. But at the time, it just seemed like a crazy thing to do. And in fact,

03:51 - 04:18

Jenny Blake: 1 of my mentors, who was a coach on the outside, when I told her I was thinking of leaving, she said, "'Oh, well, can I have your job? "'Could you put my name in?' And I thought, that's discouraging. If even the someone I'm looking at, admire on the outside, wants my job, what am I doing? And so I was so afraid, what if I go broke? What if I go broke over and over? This was the record playing infinitely in my mind. And I said, you know what, I can ask that question. What if I go

04:18 - 04:48

Jenny Blake: broke? At least let me at the same time ask, and what if I earn twice as much in half the time? That became a guiding light for me. Over the years, I've now been self-employed for 13 years. Just earning twice as much and half the time is no good if you hate the work, it's not making an impact. If it's kind of soulless, that doesn't interest me. So over the years I've added with joy and ease, it's just as important to me how I'm working as what I'm creating or how much I'm earning. And then that

04:48 - 05:18

Jenny Blake: last piece that serves the highest good for all involved is kind of doing business in a heart-based way, which you were so generous to give a shout out 1 of your recent episodes, is kind to create abundance for everybody, not just the owner benefiting from free time and systems, but the team members, the customers, the clients, the broader community, that there are so many businesses that kind of grow at all costs and then step on people to get there. That didn't interest me at all. So all 3 parts of the phrase are now equally important.

05:19 - 05:53

Rochelle Moulton: Wow. I could so feel that as you said those words. I felt like I was with you on the journey. I love what you said before you launched Pivot, your second book. And you said, So I committed to building a better, more blissful business, 1 that would be heart-based, systems-focused, delightfully tiny and fun. And so sort of on the same theme, can you parse that out for us a little bit? I think you just told us what heart-based is, but what are systems focused and delightfully tiny to you? What does that look like?

05:54 - 06:26

Jenny Blake: Well, 1 problem I had when Life After College, my first book came out, is that I was the bottleneck. The more success the book had and Target picked it up to be in the new Grad NCAP displays like among just 3 other books at that time, that was a big deal. And yet I was completely the bottleneck in terms of fulfilling any services that marketing the book would generate. So whether it was one-on-one coaching or speaking, if I got tired and I needed to take a break, the entire business engine ground to a halt. And that

06:26 - 07:02

Jenny Blake: was so stressful. I hated that feeling. I hated that feeling that if I needed to take time off, everything stopped. Or if I no longer wanted to do those one-on-one or even one-to-many services, that the business revenue stopped. So I became absolutely determined with my second book to build scalable revenue streams. Like I like to stay delightfully tiny as in have the minimum possible team or minimum viable team while still creating work that can scale far and wide. Again without me getting in the way of that. So it was very deliberate with Pivot of setting up

07:03 - 07:31

Jenny Blake: things like corporate licensing for licensing the IP, things like training a team of coaches so that I was no longer doing one-on-one work that when we got demand coming from people reading the book or listening to the podcast, they could work with somebody on the team and we would have a revenue share agreement. Those clients would even be built on monthly retainers, so there's recurring revenue. And I created a private community where it was the same amount of work if I had 10 members, 100. I never did get to a thousand, but that too was monthly

07:31 - 07:46

Jenny Blake: recurring revenue and licensing was annually recurring revenue. So it meant that speaking gigs became, they were very lucrative for me pre-pandemic, but they weren't the only thing that if I needed a break, those other 3 streams would keep working.

07:46 - 08:03

Rochelle Moulton: Well, that's always the challenge with speaking. I mean, you have to be there. And not only do you have to be there, you have to get on a plane usually. And so it's not just an hour to do a keynote. It's all the prep. It's a day of travel on either end at a minimum, depending on where you're going. It's definitely not scalable.

08:04 - 08:37

Jenny Blake: Absolutely. People kind of their eyes pop out of their head when they hear sometimes keynote fees. I mean, pre pandemic, I might've charged 25 K to do a cross country event, but Exactly as you said, it's minimum 3 days, but most likely I'll spend Monday packing, Tuesday flying, Wednesday doing the event and listening to other people's sessions, Thursday flying home, Friday completely exhausted and useless. There will be no work getting done. And that's the best case scenario if you don't get sick or come down with something, which is very much a possibility now. So it's really

08:37 - 08:40

Jenny Blake: not the hour that you're on stage. It's the week of opportunity cost.

08:40 - 08:52

Rochelle Moulton: Exactly. I think we forget about that. But do I remember correctly in the book that you talked about when you did this, when you license your pivot programs that translated into almost $700, 000 of revenue that year?

08:53 - 09:26

Jenny Blake: Yes, I had 2 licensing clients. I really for 8 years tried to land a third. The pandemic hit right in the middle of those efforts, so I never did. But it was six-figure contracts that would recur annually, and now I'm down to 1 client. But between those 2 clients, I mean, that was at least halfway to earning what I earned. And yes, that was 2019 that I hit 700k. And I actually wrote a post on Rolling and Doe about why revenue goals don't work for me because

09:26 - 09:27

Rochelle Moulton: I just read that yesterday.

09:29 - 09:56

Jenny Blake: Yeah, I'd been so obsessed with hitting the elusive 7 figures that I didn't really appreciate the 700k that I could have, would have, should have, knowing that it was only going to go down for the next few, having so much disruption these last few years. And you know, I'm kind of, I have to own my part in that too, that I wrote a book called Pivot about being agile. Sometimes I feel like the disruption shakes me up because I'm meant to do something new and different. I'm not the type that will just give the same stump

09:56 - 10:36

Jenny Blake: speech for 25 years. So a combination of factors, but yes, licensing was super joyful. I mean, talk about the intersection of revenue, joy, and ease, because I joked that this 1 at that time, it was Microsoft Word. This 1 Microsoft Word file landed $150, 000 book advance, paid out in 4 parts over 2 years. And then the licensing generated almost a million dollars over the next 8. All from these ideas in my head. That's what I found so mind blowing about what's possible for licensing IP. And once you create IP with a really strong brand around

10:36 - 11:07

Jenny Blake: it, I don't think it's just IP, it's everything else that goes with it. Having a book and a workbook and a process and method that really resonates, companies seem to love that. But it was just so incredible to me that that 1 little word file could generate so much. And also, it made me really happy that keynote speaking, I am the bottleneck to the information getting out into the world. But with licensing, people can teach each other within companies and they can teach in their own language and it just made me really happy once I let

11:07 - 11:23

Jenny Blake: go of the perfectionism of trying to control exactly how the pivot material was taught everywhere. To actually let it loose, set it free, let it spread And I think ultimately that has also helped with other parts of the business like book sales or podcast listeners and things like that.

11:23 - 11:55

Rochelle Moulton: Well, I think about just the, on the impact alone, you've got all of a sudden you have multiple people using this material, learning it, teaching it to each other. You could never do that 1 by 1, 1 at a time, even speaking, it's still limiting. Totally get that. I love that. Absolutely. Well, you kind of led me into my next question because I was looking at Rolling and Doe and what you're doing with that, and this is the outside looking in, so please tell me if I've got this wrong, it's something that I mostly see with

11:55 - 12:20

Rochelle Moulton: journalistic writers. So you've created a paywall and sub stack, right? So you have a revenue stream from your content. And can you walk us through your thinking about that, and especially how it plays into spending your time? And I'm wondering, because it feels experimental. Like, maybe there's another book incubating there. I sort of feel like I'm seeing book number 4.

12:21 - 12:53

Jenny Blake: Thank you for saying that. Yes, people have asked. The story behind Rolling and Doe is that I lost my biggest and favorite licensing client and hint, hint, it's my former corporate alma mater. So I don't want to say it publicly because I sign all kinds of NDAs and whatnot. But I loved every year for 7 and a half years working with them and I loved when I would come in for keynotes. I always think it's just I got them, they got me. But it's been a very strange year in business. 2023 started with the fastest bank

12:53 - 13:26

Jenny Blake: run in history with Silicon Valley Bank. WeWork declared bankruptcy. I mean, things are still very wonky despite all the headlines saying that, oh, we have a soft landing and immaculate deflation. Like, I don't think I'm feeling that in small business. Neither are any of my small business owner friends, maybe with 1 or 2 exceptions. And so what happened when the pandemic hit was that I lost 80% of my income in the first 2 weeks of March after the lockdown between speaking gigs that were canceled 2 years out into the future. I had an $80, 000 workbook

13:26 - 13:55

Jenny Blake: licensing contract that was overdue to be signed. They were supposed to sign by end of January. They pulled out at the last minute. So I just watched my entire business. I mean, it was beyond every worst fear that I had of what could happen running my business. It was just so much worse than what I had ever imagined. And I'm the breadwinner for our family. So it's me, my husband and Ryder, as you mentioned. The difference between that moment and then losing this biggest favorite client in 2023 was that now I was out of runway. I

13:55 - 14:27

Jenny Blake: had spent 2 years investing in free time, creating the most beautiful book that I could imagine, launching the podcast, launching this whole new part of my business that was really where my heart was, which was working with small business owners with delightfully tiny teams. But now this time losing that client and having 2 days later, another licensing client who had a proposal out for a year came back and said they're going to go with another vendor. So once again, 150 K wiped off the table in a week. And now I'm tired and I don't have any

14:27 - 14:57

Jenny Blake: more savings. I'm just at my wit's end. And I did not know...