Free Time with Jenny Blake

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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TRANSCRIPT

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 what else to do other than come home and write. And it was when the Canadian wildfires were happening. So New York looked apocalyptic. I was coming out of my own podcast studio at Times Square. The skies were black. People were wearing masks again. I felt like I was in a movie of the end times. And I started writing and I just haven’t stopped. And here we are now 6 months later. And I will say that there’s, I felt like there was so much business

14:57 – 15:29
Jenny Blake: owners, small business owners were experiencing behind the scenes that nobody was saying. Because I’ll speak for myself, I’ve always been afraid to say what I really feel or how hard things can be, because I didn’t ever want to become a self-fulfilling prophecy of further driving my clients away. Like if I admit that I’m struggling, they’re gonna say, oh, but on that horse, business is tanking. Let’s choose this speaker, coach, fill in the blank, whatever, over here. And when I lost that big favorite client, I just didn’t care anymore. I just thought, you know what? I don’t

15:29 – 15:57
Jenny Blake: care if I repel everybody. I will at least be saying the hard thing and I will at least be helping other small business owners feel less alone So that’s been my commitment and I appreciate you saying it could become a book What’s funny about that is that you’re right with substack and the fact that it’s a paid substack It’s the first time in 18 years that the thing I’m doing isn’t a means to an end like, oh, I hope by writing I can drive business or results for some other area. It’s the first time that it’s

15:57 – 16:15
Jenny Blake: actual true reciprocity. But also with the paywall, I’m able to speak more privately. So it’s not Googleable. I don’t feel like it’s just wide out there on the internet for anybody to see. You kind of have to be paying to get to the really, the heart of the matter, which I don’t feel safe posting publicly.

16:15 – 16:16
Rochelle Moulton: The juicy stuff.

16:17 – 16:49
Jenny Blake: So it could be a book. Yeah, it could be a book. But the numbers in publishing make it where getting a new sub stack subscriber at $11 a month or $108 a year, they’re paying that on a recurring basis, whereas selling a book is just a 1 time thing. It’s interesting because the math doesn’t really motivate for a book other than creating an artifact of rolling and dough, which is possible, but it would have to be like a kind of print-on-demand side project almost because otherwise it’d be so much better to just encourage new subscribers.

16:49 – 17:19
Rochelle Moulton: Well, yeah, I mean, it’s the book substitute because I look, you know, you have 3 books that kind of aligns with what you said about, I don’t wanna say the same thing for 25 years. I want to explore something new and then share that. And who says it has to be in a book? I love that you’ve been able to monetize this. I mean, 1 of the things I noticed with this, and I just signed up recently, so it’s a short experience, but you tease the paid content with the free content and you do it so

17:19 – 17:34
Rochelle Moulton: well. It’s almost like you’re reading this cliffhanger and it’s like if you press this button, you can read the rest. Does writing that way, do you feel like that gives more pressure to your writing or is it just kind of natural for you because you are a really good writer?

17:35 – 18:09
Jenny Blake: Thank you. It’s so fun. I love that you’re asking about this in particular because it’s so rewarding. In some ways this is a truly meritocratic system which is that if I write well enough, and if I create a good enough cliffhanger, a certain handful of people will pay. And sometimes people subscribe and they say, oh, your cliffhangers are so good, I finally gave it. And I didn’t know how to do this. Like, I don’t have an MFA. I’ve been reading craft books ever since I lost the client just because I’m energized by learning about what I

18:09 – 18:40
Jenny Blake: guess the biz calls creative nonfiction or literary nonfiction, personal narrative. There’s all these names for writing that isn’t so business functional. Because what was happening over the last 6 months, even on my podcast, Free Time, that’s more of where I share what I’ve learned, what’s working, what I figured out, systems to set your time free. But I’ve just been feeling increasingly like I don’t know anything. It’s like the sky is falling. It hasn’t stopped. The rugs keep getting cold. What am I going to say to give anyone advice? So with Rolling and Doe, I’m really trying

18:40 – 19:10
Jenny Blake: to teach myself craft and those paywall insertions. It’s fun that Substack lets you pick where to put them. It’s a challenge to me to do a good enough job. And then if someone continues, I know they’re going to get good stuff. The thing is I don’t pay while posts that don’t need to be paywalled. So if you’re reading something paywall, that’s cause I’m sharing financials, where I’m sharing, maybe someone sent me an email that I wouldn’t want to just be blasted out online. I’m sharing about getting rejected by my publisher, stuff that is juicy. So I

19:10 – 19:15
Jenny Blake: don’t feel too bad about making them feel good enough, but it’s a fun game.

19:15 – 19:26
Rochelle Moulton: Yeah, it is kind of a game. And I noticed in your podcast, the ones that are solo episodes, there is a personal narrative feel to it. I noticed that. Yeah, that’s fun.

19:27 – 19:59
Jenny Blake: Yeah, the solos. See, that was something where The big secret to podcasting is that’s just a great way to make friends. So you know, Rachelle, I don’t have to tell you, but I really loved, I’ve been podcasting for almost 9 years and I’ve met so many wonderful people on both sides of the mic where I’m the interviewer or the interviewee, just like this. And then I set a challenge to release a solo episode once a week, just to continue, I call it ongoing public original thinking. I guess it’s a form of thought leadership, but it’s just

19:59 – 20:28
Jenny Blake: on an ongoing basis. Am I putting something unique into the world? And we all have our own way of doing that. I like pulling metaphors or little personal anecdotes or combining them with something really tactical and practical. And there were so many weeks where I had no clue what I was going to say, but I just go into the studio. And so having that accountability, I guess the point I’m making here is that I really didn’t know if I would have something to say every week, but just making that commitment helped me rise to that occasion.

20:28 – 20:55
Jenny Blake: And the same thing is happening with Doe. Sometimes I get stressed, oh, there’s a deadline, something’s due. But then I’m so glad that I held myself to it because in the past when I just let myself be really willy-nilly, even with self-imposed deadlines, sometimes I would skip my newsletter for a week and next thing I know it had been 6 months. Ouch. Sometimes we need to do things like that. But yeah, I didn’t communicate it. There was no logic behind it. So these kinds of practices helped me stay consistent.

20:56 – 21:25
Rochelle Moulton: Yeah, no, I love that. Thanks for sharing that. I feel like it’s right from the front lines. 1 of the pure joys of your book, the free time book for me was how much you dedicated to creating workable systems that can unbottle neck your business. You tell this story about creating instructions for your friends, London flat. I mean, that just cracked me up. I’ve done something like that. But the idea is how can we use that same idea in our businesses?

21:26 – 21:56
Jenny Blake: Yeah. Oh, I love the story too, because It encapsulates so much. The way that I use the word free time, of course, yes, it’s a noun. It’s what we can do in our time off when we’re not working. But really this book is teaching free time as a verb. How do we get better at the skill of setting our time free? And we do that through smarter systems. So the spinach of the book is that it’s really about operational efficiency. But I just don’t come out and say it. And I try to share all kinds of

21:56 – 22:26
Jenny Blake: systems, thinking and principles, but in a fun, delightful way. Like a lot of food metaphors, talking about cookie dough and popcorn, gonna make everybody hungry. But it was important to me because so many systems books are written by men. In fact, almost every single 1, bigger than 1, written by a woman. Yeah, in the business arena. So I thought, let’s have a little fun here. The London flat example was really, came from feeling kind of guilty because my friend was letting me crash at her place in London. I was on a work trip and I would

22:26 – 22:49
Jenny Blake: get to see her a few days later. I was texting her as, you know, as I was taking off and she was busy. She was traveling for work. Said, okay, how do I get in? Who do I check in with at the lobby? What’s the wifi? Now she was texting me back. I thought, this is so terrible for her. She’s gonna have to text every single guest over and over the same things. And so I wrote, would you like me to create a Google Doc with all these answers so you don’t have to repeat yourself in

22:49 – 23:18
Jenny Blake: the future?” And she said, yes, please. So I created the doc, shared it with her email, thinking nothing of it, got on the plane. By the time I landed, the Google Doc was entirely filled out because I had reduced her starting friction, as I say in the book. It kind of launched her into writing down everything she would want me or other guests to know. By the end of that day, I hadn’t even checked in at her apartment. We now have a full-blown guide for me and anyone else of staying there. You know, Airbnb has its

23:18 – 23:48
Jenny Blake: hosts do this. So if any of you listening are an Airbnb host, you’ve probably already created something like this. But there’s no reason that every single 1 of us shouldn’t have a guide to staying at my house when your friends and family coming into town. And then the best, most redeeming thing was that a couple years later, when I was writing this kind of opening chapter of the principal section of the book, I don’t know, I was staying at my friend Anne’s house And I was reading her a book excerpt and she said, oh, the Google

23:48 – 24:16
Jenny Blake: doc, the 1 for Julie’s apartment. And I had no clue and knew about it. But here was another friend who had benefited from that same doc. So that taught me that the mark of a good system is that it’s harder not to use it. That you know you have a good 1 when you don’t want to go without it. Because sometimes people say to me, oh, I’m not good at systems or systems thinking or systems are just not for me. But sometimes there’s something so good that you don’t want to go back And it sets your

24:16 – 24:23
Jenny Blake: time free indefinitely. And that was the case for Julie and the stock. And it’s really a metaphor for so many things in our business.

24:23 – 24:47
Rochelle Moulton: Oh, God, yes. People laugh at me because I have spreadsheets for certain things. I have Google and Word docs for others. But it allows you to free up your brain for something else. You know, the stuff that is recurring. I mean, you just don’t want to have to think about that. Like, I’d rather think big thoughts than how to get somebody a key to the door or how to tell them to get home from get here from the airport. Or just,

24:48 – 25:21
Jenny Blake: yeah, repeating yourself. Like something that really bothers me is repeating myself. Like let’s say there’s turnover on my team. Nobody works full time, including me, but I often have contractors. I hate if I’m explaining the same thing for the umpteenth time. 1 thing, I’ll give you 2 examples of this. 1 thing is now when a certain type of email comes in through Help Scout, which is what we use software for a shared inbox, sometimes I’ll automatically append a note on how to handle that email and the link to our SOP, which I keep everything a notion

25:21 – 25:52
Jenny Blake: for my business operations. And so there I did an episode called Train the System, Then the Person. That meant that even if the team member changed, The next team member, when that type of email came, would come in, it would already tell them exactly what they would need to do. Yes. Then the other example, I had a friend who tried to hire a salesperson. Again, contractor. She was paying a lot of money, maybe $4, 000 or $5, 000 a month. And, you know, she has to convey a lot of information to get this person up to

25:52 – 26:22
Jenny Blake: speed. The salesperson was going to reach out to all these people. Long story short, at the end of the 3 months, they had nothing to show for it. There were no new sales and they decided to go different directions. That was a completely sunk cost for my friend because what she didn’t ask that person to do is document every single thing you do. Anything you need to ask me about, anything I explain, anybody you reach out to, anything that works, anything that doesn’t work. I will say to someone on my team, I want you to imagine

26:22 – 26:42
Jenny Blake: we are gonna completely hand this off to another person in 3 months, and neither 1 of us gets to speak with them. So create the documentation as we go, so that that exists And at least then, let’s say you’ve paid $15, 000, at least you have a document for the next person so you’re not starting completely from scratch.

26:42 – 27:16
Rochelle Moulton: I so made that mistake in my first business with my first sales hire. I corrected it with the second sales hire because I realized it wasn’t about the person. It was about me and whether or not I’d set them up for success. So love systems. Yeah. There’s another thing I really liked about free time, and that’s that you dedicated a whole chapter to inviting nonlinear breakthroughs. And I just love that because it just takes conventional wisdom and turns it on its head. I think we spend way too much time assuming that the only way we’re going

27:16 – 27:27
Rochelle Moulton: to make progress is through grit. I’m going to work hard. I’m going to have intense willpower. So will you talk some more about how you see non-linear breakthroughs?

27:29 – 28:00
Jenny Blake: Sure. Yeah, this is just the idea that sometimes we imagine exactly like a long, hard linear climb up into the right, tick by tick by tick. And there are also moments where we just get stuck. Like, I don’t think anybody knew how to handle a global pandemic. We were all figuring that out at the same time. So the idea of inviting a nonlinear breakthrough is saying, I’m hitting a wall here. Something is not in flow. And if I just keep doing more of what I’m doing, things gonna happen, or I will not work my way out

28:00 – 28:13
Jenny Blake: of whatever this problem or situation is. So a nonlinear break there’s kind of a joyful way to almost surrender. I took a lot of inspiration from the book Outrageous Openness by Tosha Silver. Oh, I bought that book after

28:13 – 28:15
Rochelle Moulton: you recommended it in free time.

28:15 – 28:16
Jenny Blake: Yes. Did you read it?

28:17 – 28:19
Rochelle Moulton: I’m still working on it. But yeah, I love the concept.

28:21 – 28:55
Jenny Blake: We can do all the super tactical stuff in business. And also, sometimes you need to surrender it and say, I’m hereby inviting a nonlinear breakthrough. I am open and available to a lightning bolt of insight or a big brig type event or something coming out of left field that I can’t even imagine. And seeing where that takes me, the Target example was a good 1 because I did nothing to get that target book deal for life after college. And they bought 15, 000 copies. I earned out my advance and the book continued to be a very

28:55 – 29:26
Jenny Blake: strong seller. After that, I had nothing to do with that happening. That was a nonlinear breakthrough. And I know that it sounds like wishful thinking, but I do think that something can shift and at least open up energetically if we admit that we don’t have full control over everything and that’s okay and that sometimes there is a bigger intelligence at work And probably the reason so many of us started our own business is that we had a hunt or an intuition or we’re spotting a trend early. And I think if we can kind of put down

29:27 – 29:41
Jenny Blake: the over-efforting in those moments, That’s when we can invite a nonlinear breakthrough or a flash of insight or a way to move forward that’s just easier or stop doing the thing at all. Yeah, I mean, 1 of

29:41 – 30:02
Rochelle Moulton: the things you mentioned in that chapter is this idea of, you know, we tend to ask ourselves, should I do this or should I do this? Should I do X or should I do Y in my business? And if you instead take yourself off of those 2 questions and say, what next step would be in the highest best interest of my business? I think it changes how your brain thinks about it.

30:02 – 30:32
Jenny Blake: Totally. And I quote in that part, my friend, Christina Rilo, who calls it the sacred third solution, that often if you have a kind of tug of war, this or that, and it feels really constricting that neither option feels very good. There is so often a sacred third, something if you can just elevate out of the problem, the ground level, it ends up feeling like, oh, why didn’t I think of that? It’s so obvious. And it actually is so much better. It feels lighter and freer all the way around. It just takes a little creativity to

30:32 – 30:52
Jenny Blake: get out of that almost power struggle paradigm. And anyone who’s in a relationship or if you have kids, you know that once you get into a power struggle of each person just trying to win, the whole thing is over. It’s just a battle of the wills versus, okay, how do we, yeah, how do we creatively solve this so everybody feels great? Like any good negotiation?

30:52 – 31:11
Rochelle Moulton: Yeah, well, I think it’s also giving ourselves some fresh air on this stuff. I mean, I think we tend to pound ourselves, say, I should know what to do next. It should be this or it should be this, versus just letting that go and just kind of putting it in the back of your mind, letting it work on a bigger question. I love when we give ourselves permission to do that.

31:12 – 31:42
Jenny Blake: And I’m experiencing that right now because, you know, I’m contemplating as you probably read about, but a quiet sabbatical where what would it look like? Something’s not in flow in my business. The experiments I’ve tried haven’t quite clicked. And if I’m too busy with my ongoing activities, as much as I love them, I’m not going to hear the next answer of what my business wants to become. And at least for me, I can only speak for myself. Sometimes it’s like my business has a mind of its own. It wants to be something. It wants to become

31:42 – 32:06
Jenny Blake: something. I’m in partnership with my business as a messenger. That’s what I feel my role is on the planet. And if I’m too busy, even doing things I love, I’m not going to hear what that is. And I’m clearly, just the state of my bank account is evidence. I’m clearly not hearing it. There is something I’m not hearing. So the only thing I can think to do next is clear the space to be able to listen more deeply.

32:07 – 32:29
Rochelle Moulton: And that is such a hard thing for most people to do, especially in the US. I mean, it’s like we’re trained from birth that it’s all about being busy and being productive. And so to actually think about having a sabbatical can feel life-changing, but it feels so wise the way that you just described it, like it’s an obvious next step.

32:30 – 33:05
Jenny Blake: I also try to debunk assumptions about if-then thinking. So a big 1 around free time more broadly is, oh, well, if I work fewer hours, then I’ll earn less money. Is that true? To borrow from Byron Katie? Is that true? Maybe, maybe not. Actually, it’s harder to work less. You have to be more strategic. You have to delegate more. That you might solve very interesting problems in your business. 1 of my friends and podcast guest, Stephen Shapiro, challenged himself for a year to only work 1 hour a day. And he said it was such an interesting

33:05 – 33:32
Jenny Blake: time and such a great experiment in his business. And we all know for our work week as well. But the point is, who says that just because you work less, you’re going to earn less? That’s not necessarily true. It’s an assumption. But when you run your own business, actually the hard work is thinking more strategically and systematically. And so what if you, again, that’s where the inquiry comes in. What if you would work half the time and you earn twice as much? What does that look like? What would you need to create in order for that

33:32 – 33:32
Jenny Blake: to be true?

33:33 – 34:05
Rochelle Moulton: Exactly, the inquiry. Love that. Love that. You just must be incredibly busy. I mean, I just look at all the things that you produce. You’ve got 2 mostly interview-based podcasts, but you have those solo episodes. I know those are work to think about and put together. You’ve got multiple sub stacks. You have a community to manage. I mean, you’ve got a lot to get done. And I know, because you talk about it in the book, that you’ve created a very specific system that matches how you like to work. Can you talk a little bit about how

34:05 – 34:18
Rochelle Moulton: we can create a time template that works for us, especially to your last point about not wanting to work all the time and be able to still make significant revenue.

34:18 – 34:46
Jenny Blake: Yeah. And I think that if someone’s used to working, I just couldn’t work 40 or 50 hours a week at a certain point. I was getting sick. I was having health problems. Now with a husband and a dog, there’s more people in my life and who I want to be attentive and present for. And as you mentioned, I take writer out once or twice a day. So I don’t even have the 40 hours. I kind of, I necessity wanted to figure out how do I do this in less time and just be really efficient. But every

34:46 – 35:17
Jenny Blake: time the book is not about efficiency, it’s not about squeezing more out with less. Like I think we’re all exhausted from that and Oliver Bergman does a great job talking about that in his book, 4, 000 Weeks. What I would recommend, and I can start with baby steps, If you’re in the mode of delivering services, it’s just carving out time to step back and have that strategic time. I suggest in the book starting with Founder Fridays. If it’s not the full day, maybe it’s 2 hours. If you’re fully booked out right now for the next 2

35:17 – 35:48
Jenny Blake: months, then start that block on month 3. It’s not too late. Start it now. Block it off recurring every Friday so no 1 can schedule. Eventually, you might learn certain things about yourself, like how much more productive or creative or strategic you are when you don’t have meetings 5 days of the week. So for me, I don’t schedule meetings on Monday or Friday, with rare exception. Every now and then I got to squeeze 1 onto those days. I only podcast for the most part on Wednesdays, sometimes Tuesday and Wednesday. And then I have internal team meetings

35:48 – 36:14
Jenny Blake: or catching up with friends on Thursdays. So part of what that helps me do is I wake up in the morning and I kind of know my purpose for the day. On Wednesday, I can get in the zone because it was really hard for me when I would try to switch from preparing for an interview, conducting the interview, get off the phone, pitch a corporate client on licensing. Okay, get off the phone. Now conduct a one-on-one coaching session. The switching costs and the energy drain of that was just too hard. Similarly, if I do video events,

36:14 – 36:25
Jenny Blake: I try to stack them on the same day. So it could be a speak, a virtual keynote, a video podcast interview, and something else. I put them all on the same day. So I only do my hair and makeup that 1 day. Yes. Hopefully only 1 day a month.

36:25 – 36:27
Rochelle Moulton: Saves a ton of time right there.

36:29 – 36:52
Jenny Blake: Yeah. I joke, I have a personality for podcasting. Like I do not want to be on video. It’s not joyful. That’s an example of something that creates friction. I can do well on video when it’s required. However, on a day to day basis, I don’t want to worry about hair and makeup and what I’m wearing and my lighting and what is my room a mess. If I had to worry about that for my own podcast, I wouldn’t have a podcast.

36:52 – 36:53
Rochelle Moulton: You can never do it.

36:53 – 37:18
Jenny Blake: Another thing I advocate in the book is 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.

37:19 – 37:53
Rochelle Moulton: Yeah. And mic drop, basically. There was 1 other thing about your book that really struck me, and I think it was after I’d bought the fifth book that you recommended. And we’re not talking about the back of the book. You’re talking about learnings from another author’s book in the body of yours. I mean, I literally can’t remember the last really good business book that did such a great job of sharing female authored books in particular. And you didn’t share just those, but you shared an unusual number of them. And I just kept interrupting my read to

37:53 – 38:07
Rochelle Moulton: go buy a book that you would recommend. I’m just curious, was that a conscious effort on your part to include some diversity in your authors or were they just books that spoke to you and you wanted to share the credit and they just happened to be heavily women?

38:07 – 38:40
Jenny Blake: Oh, another question I’m delighted by was no one’s ever asked me about this, but I take great pride. I see myself as a squirrel. I collect all the idea acorns and recommendations. I love being a curator. So it makes me really smile to know that you found things. You discovered things. Like I love creating really rich, and when I’m writing the dough articles, rich links, embeds, music, songs, like podcast episodes. I love just kind of packing in little Easter eggs that somebody can find and continue their adventure, like kind of on the trail that I might’ve

38:40 – 38:41
Jenny Blake: taken.

38:41 – 38:44
Rochelle Moulton: Yes, you do a great job of that in free time.

38:45 – 39:15
Jenny Blake: 3 things that I did for gender diversity and overall diversity too, but specifically around gender because business books are so heavily male and they talk about systems they never once mentioned an example from home. Why? Because so many of them have a little fairy at home taking care of the household, the adulting, the stuff that’s even more annoying than the business. So none of the books even address what to do at home in terms of systems thinking or have any examples from it. They don’t even have to think about it. So, and I love men. I’ve

39:15 – 39:41
Jenny Blake: never, Nothing I do in my business is for women only because I actually, it’s kind of me taking a stand. People will automatically try to put me in the box as being for women, but I want to say that women can be for women and men. We don’t only have to be. I love people who do work with women, but I had too many moments where people were putting me kind of in the corner saying, oh, well, you’re a female, so you must be for women. No, actually, men can learn from women too. Isn’t that shocking?

39:42 – 40:18
Jenny Blake: Shocker. Yeah. That’s my rant. Then like free time, I won’t even go there, but essentially it won an award, it won 6 awards, but 1 of them was in the self-help category. And I thought, if this book, this is a book on business systems and operational efficiency, If it was written by a man, would it have been categorized as self-help? It pissed me off. So, anyway, so the point of like lifting up equal parts, I had every chapter of the book mapped out in Notion, it’s called the database, But I actually had a grid of the

40:18 – 40:52
Jenny Blake: gender of every expert I quoted in the book that included authors or anyone I interviewed or anyone from the podcast. And I would tag male female. I guess at that time I didn’t have anybody non-binary. And I made sure that the gender balance was even for stories I featured, examples, and then for experts. I also made sure that the opening epigraphs to every chapter had a good gender balance because, again, a lot of business books quote like old white men from history. So like, oh, Socrates says this and then Marcus Aurelius and then Benjamin Franklin and

40:52 – 41:14
Jenny Blake: Ralph Waldo Emerson in the row. And it’s like, you could sell an entire book only quoting white men from history. So I also tried to get some interesting epigraphs that would break from that norm. And those were the 2 main things. There’s a third that I did, but it’s escaping my mind at the moment, so those must be the 2 more important ones.

41:14 – 41:47
Rochelle Moulton: Yeah, it was striking to me. And I read a ton, but I’d especially been looking for books by women because I wanted to introduce some authors in this podcast and I thought I need to find more. And yeah, your book was a treasure trove on so many levels, but including that 1. Jenny, I see what the time is. I want to be respectful, but I would love to ask you 1 last question, which is, 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

41:47 – 41:48
Rochelle Moulton: do?

41:49 – 42:27
Jenny Blake: Oh, that’s such a good question. I would say do less. When I launched my business in 2011, the thing that was really in Vogue was diversified streams of income. And that was the hot thing. Like I had 13 at 1 point. I probably still do some more passive, some more active. And I just remember thinking that’s the goal. We should do coaching, online courses, we should do speaking, maybe have royalties and then maybe physical product sales. And the goal was like more and more in terms of diversified streams of income. And it was only later, halfway

42:27 – 43:01
Jenny Blake: into running my business, that I realized every single 1 of these income streams is a business unto itself. I had this realization that there are people that they are a full-time substacker. They earn a living from it. It’s all they do. Someone else might be a full-time podcaster. They earn a living. It’s all they do. Someone else, a coach. Someone else, a speaker. Someone else, corporate IP licensing. What the heck was I doing trying to run all these things, private community, subcontractor coaching team? Every single 1 has process, has documentation, has parts of the website that

43:01 – 43:33
Jenny Blake: need to be maintained, has customer service. It’s an incredibly complex business setting it up that way, let alone what I have now, which is 2 IP skis, as I call them, pivot and free time. It’s like running 2 separate businesses. It’s really not something I would do from scratch if given the choice. It’s just something that I’ve kind of landed in after 13 years and some of its legacy stuff that’s digging around. But my work now is really carving away at that marble, Michelangelo style. Like, okay, there’s some focused angel inside of my business. Now the

43:33 – 43:58
Jenny Blake: work the last few years has just been, what else can I remove? What else can I remove? What else can I remove? Because it all adds complexity and it makes it so much harder for even team members to support you when there’s that much going on. If you don’t want a big team. Like if somebody wants 10 employees, by all means, create as complex a business as you want. The biggest my team was, I was the most miserable. And ironically, it was right as free time was launching. So I took my own medicine and scaled way

43:58 – 44:00
Jenny Blake: back down by the end of that summer.

44:00 – 44:31
Rochelle Moulton: I remember there was a point in the book where I think it was a former boss of yours said, where are you hiding the 5 Jennys? Because you got so much done by yourself. They wanted to know where are the others? And I think sometimes when we’re built that way, And at Google, I’m sure that initiative was rewarded, right? So we tend to take it into our businesses. But we usually learn a hard way, and I’m raising my own hand here as well, that simplicity can be a much more elegant solution with these kinds of businesses.

44:33 – 45:03
Jenny Blake: Yeah, and I also think, I thought that if I was a good entrepreneur, I would grow my team. That there was something wrong with me because I didn’t want full-time employees. Or I’ve read dozens, if not hundreds of business books on leadership and management. I’m not great at it. I don’t enjoy it. I’d rather be reading a book. I’m not good at it. Like, so I think that what I talk about in free time is the Goldilocks number. Whenever they talk about team size, It’s all about efficiency and productivity and what size team is most functional

45:03 – 45:35
Jenny Blake: and beneficial. But they never say what size team is most joyful for you as the leader. Now, if you have a vision that you want the vision expressed to its maximum potential in the world, regardless of your personal preferences, that’s something else. I’m trying to build a really connected, aligned business. And for me, that meant also giving myself permission, yes, to delegate, but if I would need to involve too many more people, I get so bogged down by what my friend Charlie calls social overhead of managing people that I stopped enjoying it. So I’d rather stop

45:35 – 45:56
Jenny Blake: 1 of the revenue streams than be dealing with too many people. That’s just me, but doesn’t create a very sellable business. But I’ve made that choice. That’s actually okay with me for a while. I was trying to create a sellable business, built to sell, do all the things. And now I don’t care anymore. I just, it’s too misaligned. It’s too hard. So I’m back to delightfully tiny and happy with it.

45:56 – 46:09
Rochelle Moulton: Exactly. You’re doing what works for you and you figured it out. I mean, nobody gets this in 1 fell swoop, right? We have to experiment with things, crash and burn a few times, and then we find what really works for us.

46:10 – 46:16
Jenny Blake: And at least now, if something works, it works. And if it doesn’t work, I have content for rolling in dough. So it’s a win-win now.

46:18 – 46:24
Rochelle Moulton: I’m signing up for the paid version on that. I want to hear the rest of the story you teased this morning. I want to hear it.

46:24 – 46:42
Jenny Blake: Oh, thank you. Well, you’ll enjoy some of the archives then. Don’t miss the mutually assured rejection. And in honest accounting is all about my licensing travails. So those are 2 cliffhangers for listeners. Awesome. Thank you so much for showing. I appreciate you checking it out. That means so much to me.

46:42 – 47:01
Rochelle Moulton: Well, thank you, Jenny. I mean, this is just you’ve been so generous with your own experiences, with all the research that you did for your books and you’re thinking about time. I love your material and what you’re putting out there and the way you’re doing it so much. And I so appreciate that you joined us today.

47:02 – 47:27
Jenny Blake: Well, thank you. And our mutual friend Lindsay made this intro. She told me about your work many, many months ago, and I subscribed. I love what you’re doing. And when she asked over, she was wondering if I could connect you for the podcast. I like left with Glee. So I’m really delighted to be connected here. And thank you so much for all of your great work that you put out into the world and for all the great questions today. And big thanks everybody who’s here listening.

47:27 – 47:44
Rochelle Moulton: Well, let’s give an extra thanks to Lindsay because I was not going to ask you. I was going to wait like a year till I had more listeners and more guests under my belt. And she said, no, you must speak to Jenny now. So thank you, Lindsay.

47:45 – 47:50
Jenny Blake: Thank you, Lindsay. Forging an Ironclad Brand is her brilliant book and even has a podcast now.

47:50 – 48:02
Rochelle Moulton: Exactly. She’s brilliant, too. So we’re going to be putting up all sorts of links to your content in the show. But what’s the best place for people to learn more about you.

48:02 – 48:25
Jenny Blake: 2 main places, it’s freetime.com is the book website and of course you can look for free time wherever you’re listening to this. There’s over 250 episodes and if you’re interested in Rolling in Dough or Substack You can go to substack.com slash at Jenny Blake and you’ll get all 3 of my publications or rolling in dough Doh.substack.com. Perfect.

48:26 – 48:31
Rochelle Moulton: So that’s it for this episode. I hope you’ll join us next time for soloist women. Bye bye!