Free Time is a Verb: How to Reclaim Your Time with Jenny Blake

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Alcohol by volume 80 proof. I think of free time. Yes, it's a noun. It's what we do when we're not working, but I actually think of it as a verb. It's an action free. We can get better at freeing our time and the way we do that is through systems thinking.

If you're looking to get more done in less time, podcaster and author Jenny Blake is here to help. This is the Launch your business podcast because we know starting a business is challenging, but it doesn't have to be confusing. Each week we give you the tactical advice and the necessary tools to scale your business without feeling burnt out. I'm Terry Rice, business development consultant and staff writer here at Entrepreneur Magazine. Let's dive in. Jenny Blake is a podcaster and the author of three award winning books including Life After College, the Only Move that Matters Is yous Next One and Free Time Lose the Busy work, Love your business. Her latest project is a paid substack newsletter called Rolling and Divine Disaster Diaries from a breadwinning business owner living in New York city. She has two podcasts with over 2 million downloads combined. In 2015, she launched Pivot with Jenny Blake for navigating change. And in 2021, she added the Webby nominated Free Time with Jenny Blake to set your time free through smarter systems. Jenny is a lifelong bookworm and aims to work about 20 hours each week, leaving plenty of time to take her dog Ryder to the park every afternoon. Let's dive into it right now. Jenny, how's it going today?

Never better. So happy to be here with you. Thanks for having me.

Yeah. And before we officially hit record, we were just kind of like chatting like we've known each other for years. So I know this is going to be a good conversation right now.

We had a shared rant on how much more fun phone calls are than when you're stuck to the computer frozen in place. So, so happy to be here.

Can you bring that back?

Yes.

All right, so let's get into it. So, Jenny, who are you and what are you excited about these days?

Who am I? I mean, if we met at a cocktail party, I might tell you. I'm an author and podcaster now. Substacker. I've never been one for the intro where I give you my elevator pitch and then at the same time I'm in this very liminal state. I've been self employed for 12 and a half years where I don't know who I am, I don't know exactly what's next. The last four years of the pandemic have been quite a rollercoaster for me, as I'm sure they have been for so many of you listening. And so I actually feel, and I just hit a big decade birthday, I just turned 40 and I kind of feel like I know less with every passing day and year. And so I'm just letting who am I? Be an open ended question that I live into. And I forgot the second part of your question already.

It's going to be related. I'm going to ask you another question that's related because when I go to networking events, I don't ask the other person what they do. So I'm going to share my approach right now. Jenny, what do you do for fun?

Well, for fun, I love taking my dog Ryder to the hill at the park every day, often twice a day, and I throw a big log around. I call him the branch manager while I listen to podcasts, talk to a friend, and or ponder things in my life and business. I just wrote a post on my newest project called Rolling In Doe d o h. Just kind of talking about the trickier parts of running a business. And I was saying that there are pros and cons to having a big dog in a crowded city because Ryder's a German shepherd. He's four now. And I'm like, you know, there's lots of p mail for him to check. We meet a lot of our neighbors. There's always interesting stories and observations. And then on the other hand, you have to get really creative about how you get their energy out. So we've come to find just the right spots at the right parks so that we can put them on a long lead and then throw sticks around.

Love it. I think a lot of us limit our options because we don't use divergent and convergent thinking. Okay, so I understand. I don't, you know, live in the suburbs and have a huge lawn, but what can I do? And what's the best way to make it happen? So I appreciate the fact that you're being that creative and innovative, but you mentioned Rolling In Dough and I'd love for you to explain, first of all, the meaning of the title and what it's about.

This is a project I started this summer. So summer of 2023, when I actually lost my biggest and most favorite corporate licensing client. So I've written three books, Life After College, Pivot and Free Time. And Pivot did really well. I was really fortunate that it kind of took off and big companies started licensing the IP so that they could run workshops where I wasn't the bottleneck. And after seven and a half years with this amazing, wonderful client that I don't name because I have an NDA, they said, you know, they had done layoffs like everybody else this year. They were tightening the budget like everybody else this year. And I had a feeling that my contract was on the chopping block. I just knew I. Oh, for the first six months of the year, I just was nervous. And this is a six figure plus check. So it's a big one that for my delightfully tiny team. And small business does make a huge difference. And the day of our meeting, June 6, my writing coach has since come to call it the Axe. Sure enough, the first thing they said is, we're just going to cut to the chase. This is the end of the road. And I didn't know what to do. It had already been a really tough Few pandemic years. When the pandemic hit, I lost 80% of my income in the first two weeks. And a lot of people had it much, much worse. But it was still so shocking because I do a lot of keynote speaking like you. And I also had almost six figure licensing contract that they were supposed to sign at the end of January 2020. And this company, the legal and procurement process, it kept dragging out to the point where they were saying, we're going to get you the docusign of day that was March 10th. And of course it just imploded at the last minute. So this summer, when I lost this, not only my big favorite client, two days later, a proposal I had sent out to another big name company. They had had it for over a year. It was a six figure proposal. Two days later they came back and said, we're going to go with another vendor. And at this time, there were wildfires in Canada. So I step out of the podcast recording studio in Midtown. The skies were dark. They were smok. Felt like we were living in the apocalypse. And that's how I felt on the inside. And I didn't know what else to do but just start writing. And that's all I've ever known to do when I go through such massive change like this. And I started writing and I didn't stop. And so that weekend at brunch with my friend, she helped me brainstorm. We both got up chatgpt on our phones and I said we were asking for titles, playing around with the breadwinner metaphor because not only am I a business owner, but I'm also the breadwinner for our family, me, my husband, and our dog. And so rolling in dough is meant to be tongue in cheek. The DOH is with a face, palm in the middle. It's talking about the divine Disaster diaries of being a breadwinning business owner in New York City. And yet I still, much like you, Terri. Like, I want to train my subconscious in the right way. So to my subconscious mind, it still sounds like rolling in dough, which is of course the ultimate aim, like getting back to that really flush stage of my business while still documenting the really tricky sides for people who are also struggling right now so that hopefully they feel a little bit less alone.

I love the theme because there's so much content out there. Like, this person's amazing, this person's amazing, this person's winning. And if you aren't, then you should probably feel bad after this episode, right? Like, that's kind of how it goes. A lot, especially on social media. We all put our best version out there. And that's something that I'm working on as well. I'm actually starting a separate podcast where I have high profile entrepreneurs come on and talk about the lowest point of their life, either personal, professional, and how they rebounded from it. And the conversations are meant to meet people just like you are where they're at, saying, look, I know you're going through it right now, but look at this person. You know, they've been through it as well, and they made it through to the other side. And I think you can, too. So I'm just glad to hear that you have, like, this social impact approach to it as opposed to, you know, just creating content that would be obviously, you know, beneficial to people, but not going as deep as you are. So I dig that. I think it's awesome.

Well, thank you. I love that you're starting that podcast. I can't wait to listen. You already have one subscriber. And that's what I found, too, because I actually searched on Spotify, which has a really good search engine for podcast episodes, not just shows. I searched what to do when you lose your biggest client, and there was not a single result. And the other thing I realized, because I love, I love geeking out about business, too. I know you do as well, Terri. Like, I'm listening to podcasts all day. I listen at 1.5, if not 2x. I'm listening for all the best practices, like other people's stories. I subscribe to probably over a hundred podcasts. I read a bunch of newsletters. And yet I found that the only people who were talking about when kind of when business goes wrong had already come through the other side. And they were already saying, you know, oh, this was my lowest moment in business, but now I'm a billionaire and it's okay. And I felt like there was something missing of just hearing from people who were still in it. And I had stopped feeling like I could pretend because I was trying to put on a brave face, as any business owner would. You're optimistic. I try to be, too. You got to get back up and do it again the next day. Like nobody's coming to save you when you run your own business. And I needed to stay positive and stay optimistic and have high energy so that I could make the next sales and the next one. But eventually, by the time this summer, I was so tired and my savings had run out because I placed some really big bets in 2021, went all in on free Time the new part of my business. What I noticed was that every time I would get on the phone with a business owner friend, they were telling me how much they were struggling and yet nobody wanted to say it out loud and nobody wanted to show it because we don't want to become a self fulfilling prophecy driving all our future clients away. And at that point I realized there's really something missing in the marketplace of ideas which is showing at a visceral level how hard it can feel even when you're not through it yet, even when you're not on the other side, even when you're not one of those shining success stories on the COVID cover of Entrepreneur magazine. That's what really like keeps me motivated to keep sharing what is often vulnerable and kind of really not putting myself in the best light, just in a relatable light.

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Well, I really appreciate you sharing even that snippet of your story. And I love the team at ConvertKit, they're great. This is our tweetable or X able of the conversation. I don't owe anyone a happy ending to my story. I mean, that's mind blowingly powerful. I just really appreciate you saying that. And I think sometimes we get insecure thinking, oh, this is such a downer. And I don't know about you, but for me, optimism and what comes with it, sometimes perfectionism or people pleasing. But my optimism is almost a coping mechanism, like of maybe a chaotic upbringing or something where I just felt like I need to bring the good energy and kind of in a codependent way, almost be responsible for other people's energy around me. Like I never want to bring people down in the room. I always want to add to the room, add to the energy, uplift people. And so it. I wouldn't have put words to it this way, but hearing you say it, I would have that same feeling. And I often do with these personal essays that I'm writing at DOE where I think, oh, I'm such a downer. God, like people are gonna unsubscribe. I'm not used to showing up in that way. And yet there's something so real about it. And knowing that part of your story and knowing that you're not almost faking a happy ending, you are happy. And I remember when I interviewed you for free time. I'm like, this guy Terry has it all figured out. I was actually intimidated after we hung up. Cause I'm like, you just really have it dialed in as a dad, as a business owner, as a podcaster, et cetera. And knowing that piece of you, I think it's, it really just adds so much depth. So thank you for this example of the conversation.

Yeah. Oh, exitable now, right?

I've never said that, but that's what it is now.

But yeah, I mean, to your point, I think it's the systematic denial of emotions that really causes like frustration and anxiety. And if you can acknowledge it, adapt and then advance, you know, you'll be in a better spot. So I, I, it's a, it's, it seems like we're both on a similar journey and we're expressing it in public. And again, my, my goal is to help other people just feel comfortable telling their own stories. Well. And again, you don't only want a happy ending, so you can x that if you would like to, to share.

Yeah. In fact, my writing coach said she, she literally asked me, we were on a zoom. And she said in business you have to know things, right? Because I've written three books and two of them are in the career and business category. And she was making the point that when you're in the business channel or the business genre, whether a podcast or a book or a keynote, you're supposed to know something. It's like a position of being an expert. She said with personal essays, it's the opposite. You can win, but it comes at a cost. Or you can lose. That works too. And I laughed. But what she was trying to say is that actually for a different type of genre, nobody really wants to read that. Like if I just bragged about myself or said how good I am, or only said the shiny things for a thousand word essay, nobody wants to read that. But the things that we are drawn into, which I can't wait to watch your ConvertKit doc, is where there's some depth and you can win and yet it still comes at a cost, or you still make trade offs in order to reach that new level or that new stage of growth. And so I think exploring these nuances, especially within the journey of entrepreneurship, which is so intense, that's where the gold is.

You made a point about exploring those nuances and I think that's a challenge and it's going to lead to my next question. But, and I think the problem with many entrepreneurs is they spend a lot of time working in their business, right? They're just heads down in the business. Once in a while take their step back and say, okay, I'm going to work on the business, like my processes, my infrastructure. But they don't go deeper and work on themselves. And one reason being is because they don't have enough time. Right? That seems like a luxury. Professional development, personal development, so on and so forth. And that's why I want to hear more about free time. Because by design, like I just talked to my wife the other day, I'm like, I'm just sick of being busy. I'm sick of it. I'm sick of feeling busy and like rushed all the time. And if that was the path to fulfillment and wild success, I'd have a lot more money right now. Like, I'm not like broke or anything, but like, if being busy is how you became like a bajillionaire, like, I'd be that three times over. So I'd love to hear more about free time, both the book and the podcast, because I think if we can solve that issue where people can just have more time to work on themselves, then they'll have more meaningful experiences as opposed to just feeling like they're grinding all the time.

Absolutely. And to your point, I think of free time. Yes, it's a noun, it's what we do when we're not working, but I actually think of it as a verb. It's an action free. We can get better at freeing our time. And the way we do that is through systems thinking. And so the book is kind of a love letter to small business owners. But it's also, and I try to weave in all these fun food metaphors and make the chapters really short and punchy, but it's a book about operational efficiency. When I worked at Google, I was there for five and a half years. I heard this quote from the world of agile software development. And it said, each time you repeat a task, take one step toward automating it. So even in those early days of my career, I always carried that with me. I was always looking. Even if it's something as simple as sending somebody directions how to get to your house, you can do it once, you can do it a hundred more times, save it as a canned response. And now for those of you listening, I mean, that's kind of something obvious in free time parlance. It's what small steps can you take today to set your time free far into the future? So it's less about. It's not. I really don't call it a productivity book or it's not even about being more efficient at doing the same old things. It's what systems can you put in place with you or your delightfully tiny team so that nobody has to think of it again. And that can include software. So the Freetime Framework Align Design Assign is a process for moving from friction to flow. And the reason Assign is the third stage is because I want to challenge all of us to double or triple how much we delegate. Again, even to software, there is so much now that even five or 10 years ago was not possible to automate and delegate. And nobody in my business works full time, including me. I work about 20 to 25 hours a week and I have one part time VA and I have a podcast production team. That's it. And so the way that I do that is by automating as much as I can and leveraging software almost as my first employee. Like I I try to get as much automated and systematized through software first. Only then do I assign it to a person.

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Yeah, this is something that I really learned the hard way because email is kind of a Sisyphean system in that it's never ending. And the more visible you become, the more success you achieve, only the more emails you're going to get. So the only reward for success in your business is punishment in your email inboxes. And now we also have an inbox across every single social media account that you decide to participate in. So you mentioned people who work in the business and not on the business, which I love from Emyth who kind of like drilled that idea into our heads. I came up with a little rule of thumb for myself Train the system, then the person. I get really annoyed when I'm repeating myself. So I realized that I was having such a hard time training team members, especially if I had turnover, how to handle email. So, finally, a couple things. We use Help Scout, which is a shared team inbox where we can write notes on messages and assign them back and forth to each other. But the biggest game changer was that I created these automatic rules. So, for example, if someone wants to submit a question to one of my podcasts, we use a tool called Speakpipe. I used to have to explain to a team member what to do, or I'd say they'd ask me, what do I do with this when we get a submission? Oh, it's in the manager manual. Okay. After the umpteenth time explaining this, I realized in Help Scout, I'm going to append a note. So when a message from Speakpipe comes in, I append a note that says, this is a listener submission. Please take the next five steps. One, listen is it relevant to the podcast? Two, if so, download it and save it to Dropbox. Here. And I include the link number. 3, transcribe the file in descript number 4, create a card in our Notion podcast production database for this listener's question. Number five, tell the listener we're so thankful they submitted and we'll let them know once their question and answer is live. All of a sudden, I have just trained the software. I've trained Help Scout to be super clear so that whatever team member, whether it's somebody new or old, whenever that next Speak Pipe message comes in, they know exactly what to do. And I now don't have to repeat myself again.

Does that work for children, too? That'd be nice.

You tell me. Yeah, you would know. Yeah.

Help Scout. I'm looking at the website right now, so. Okay, so those are two great tools that you already mentioned, Speak Pipe and Help Scouts.

So I feel like descript is so good for transcription.

Descript is amazing. Like, my buddy Jason Pfeiffer put me onto that, like, years ago. And a lot of these low code or no code tools, they just keep on progressing and there's going to be an acceleration just due to, you know, everyone using AI more often these days. So I feel like many business owners could save a lot of time, but it's taking a week off and just saying, okay, what can I automate, delegate, outsource, whatever, and then get back into business and just have so much more time. But again, if you feel stuck in it, like, you know, I Can't get off this, this treadmill, then you don't get that advantage. And then, then other people are passing you by and they're also having more vacation time. Right. Because they invested in, in these processes. So I'm glad that you're giving just tactic level details on how we can do this stuff. I think it's beneficial to show those examples.

And speaking of software, so one more systems framework that's been really helpful for my team and I, I used to ask what would happen if I got hit by a bus when I was first starting out and running my business. And I realized that's such a violent question that now 12 years in, I'd be asking it hundreds of times, like imagining getting hit by a bus. So early days I started asking, what if one of us got whisked to Fiji with no devices, no ability to give notice, could anybody else on the team step in and seamlessly do the work? So the Fiji test becomes a barometer for is everything documented? No piece of information should live in anybody's mind, not least of which my own as the owner, no team member, nothing, nothing lives in anybody's mind. So our entire business, all the operations, including a manager manual with standard operating procedures, lives in Notion. And I just learned that Notion is releasing an AI feature where let's say a new team member can actually ask the Notion AI a question such as how do I respond to a speak by inquiry? And the answer will populate and then it will point you to which pages to go reference where that information came from. So even something like that new feature, hot off the press, is going to be a game changer because we will document everything that exists about the business, how we work with clients, our pipeline, everything can live in Notion. And you know, tasks, projects, databases, CRM, all of it can be there. But what's now amazing is that a new team member or any team member can almost have a chatbot within your business with Q and a, how do I do something? So that's going to take a lot of pressure off of the owner who often gets bogged down just by answering questions all day, especially if you end up expanding the team.

Let's, I'm going to play devil's advocate right now. There's someone listening and they're like, wow, that sounds really cool. And they're just not going to do any of this stuff. And one of my favorite quotes is knowledge uninvested in labor is wasted. And I'm not sure why people don't take these actions sometimes. So I'm going to ask you, what friction have you experienced in regards to people adopting this type of approach towards their work? Like, why do they not apply what they've learned? Because we're talking about the benefits. It's very clear what's holding people back from doing this and how would you encourage them to move forward.

One thing, like you said, it can just be a lot. You're already overwhelmed. Keeping up with the day to day, that's one thing. Just feeling overwhelmed. And there is some starting friction and some initial costs up front. Especially with delegation. We've probably all been burned by delegating something. It goes wrong and you're like, I'm never going to delegate again. So that's one thing. And then the second thing, sometimes I'll hear from people who say, I hate systems or hate learning new software. I'm anti GPT, you know. Okay, what I would recommend, pick the friction area that's dragging you down where you are, the bottleneck you are getting in the way, you're stressed in free time. I call it the burdensome bees. Anywhere in your business where you are getting bottlenecked, burned out, bored or buried by bureaucracy, that area you are going to be more motivated to fix because it's causing you pain. So start with one of those and that's where you want to ask the question, like align. Is this still aligned with your goals as a business owner? If so, keep it. If not, eliminate it. But if it is, maybe you need to realign it. Maybe you need to readjust something. Design is like, what's your ideal impact from this area? And also designing a process and then assign, how can I get help here? How can I take some of the pressure off? Why I think a lot of business owners hesitate even when they delegate is they're just having to do so much work in order to delegate. Two things that have helped me, hiring experts, like actually don't hire entry level people just because they're the least expensive to pay. Hire experts, it'll be worth it and you won't have to train them as much and you can be more hands off. You're not managing so much as just getting out of the way, getting them what they need. But the second thing is if you are going to delegate, put the onus on the other person. So we're going to meet over zoom. Please transcribe the recording or put the recording into descript. And anything that I've said or any question you ask me throughout our work together and if that answer doesn't exist in our documentation, please add it. So instead of the owner taking on the onus to do all this work that you and I are talking about, delegate that too. Like delegate that to the team to say. And please document this or anything I say, add it to our manager manual. There are ways that will actually save you time, but also save you time, not just today, into the future as certain types of emails or questions come up again. So I guess to bottom line it, cause I don't think I answered that very well. I would just say start small and start with something that's legitimately draining you, dragging you down, that you will actually be so happy if you can just spend one hour putting your mind around what a meaningful fix would be or just cutting it out altogether.

I'm going to do a time audit next week to discover areas of optimization and opportunity. I'm almost afraid what I'm going to discover, but I know that's the first step in determining how I can get more free time back. So I'm glad we're having this conversation now. And I want to ask you one parting question before we part ways here. What is one lesson about entrepreneurship that you wish you learned sooner?

Ooh, that's a good question. Well, I can't resist. But to just add on to your time audit, I heard a great suggestion. Somebody on a podcast said that at the end of every day, they retroactively color code the meetings on their calendar. Red if that meeting drained them, orange if it was neutral, and green if it energized them. And so I think sometimes we think we have to do a time audit looking at the future or how do we spend the next week? But you can also do it looking backward. And I use rescue time operating in the background, which is another tool that helps me with my own time audits. As far as what I wish I had known. Oh my goodness. It's constantly evolving. I feel like when I first started my business in 2011, diversified streams of income was all the rage. It was like, how many revenue streams can you have in your business? 5? 6? At one point I had 12. I probably still do some of them more active than others. Some of them are genuinely passive, like getting royalties from my audiobook. Some of them are super active, like if I'm traveling to another city for a speaking gig. But 12 is a lot. I think what people don't realize, myself included, is that 12 revenue streams means 12 sets of process documents. It means 12 types of clients that you're dealing with. It means so much complexity on the back end that as you and I were talking before we hit record, Terri, about focus, actually, more is not more sometimes. And although it sounds good to have so many diversified streams of revenue in the business, actually, what would it look like if you only had three? Like, yes, you can be diversified. You don't want to be too fragile if you only have one. Like they always say one is the most dangerous number in business. One client, one revenue stream like that, you're kind of at risk. But less is more. And I, every year that I'm in business, I'm actually trying to look at what can I cut out, what can I stop doing. Like, I always think about, I know it's cliche, but Michelangelo carving the stone and looking for the angel inside. I think that's true of our business. There's an angel inside of our business and there's also the angel inside of us, which is our true unique gifts. And how do we just remove all the clutter that's getting in the way of expressing those?

Jenny, this has been amazing. I appreciate it. Before we take off, where can people follow you? Where can they learn more about you?

You can actually get everything I create. This is new. I just migrated everything over to Substack. If you visit substack.com ennyblake and if you want to learn more about Freetime and get the toolkit that has a whole bunch of templates for what we've talked about, you can visit itsfreetime.com there's a book that I highly encourage. I actually feel like I wrote the manager manual for you, so I've saved all of your time. You don't have to write that now and the podcast. So just look for free time wherever you're listening to this one.

Awesome. Thanks, Chris, Jenny, I appreciate it.

Thanks so much, Terri. And big thanks everybody for listening.

And that's our show for today. You can learn more about jenny by visiting itsfreetime.com where you'll also find links to her socials and podcasts podcast. Thanks for listening and I'll see you next time. Apply what you've learned on today's show. You'll find the show notes and more resources at Terryrice Co Podcast. Again, that's Terryrice Co Podcast and the best way to support this podcast is by subscribing, telling a friend and leaving a review. Also, you can get more tips by following me on Instagram at Terryrice or follow me on LinkedIn. This episode was produced by Josh Wilcox of Brooklyn Podcasting Studio and edited by Dan Lardy Special thanks to my wife, Dominique, for keeping our kids relatively quiet as I recorded. Thanks again for listening. I'll see you next time.