210: ⛵️Knot a Care—Sailing the Free Time Seas with Joy and Ease
8 Dec 2025 · 24 min
Jenny Blake uses sailing metaphors to argue for running a business with agility and joy instead of chasing growth. She shares a difficult week managing her Substack project and paid community, and makes the case for small teams, freedom, and deliberate choices over scaling at all costs.
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Be agile and embrace how quickly we can make decisions, how adaptable we can be, how scrappy we can be in terms of resources, how we don't need to grow at all costs, we don't have to scale beyond what's joyful to free up even more time and that we do have room to take some risks while not being in as rickety a structure as the raft that there's so much to celebrate.
This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
Two months ago, Michael and I were sitting and having coffee in the morning and he congratulated me on filling the 10th and final spot in my Voxer coaching pop up. This is the second year that I've run it. It's super joyful and we had no clue what was going to come down the pike the very next day. In fact, it would be one of the hardest weeks of business and 12 years of running my business. He knew that I had been nervous about the news. I was waiting to hear back from a few clients on the future of our work together and what felt like the future of my business. But I didn't have the answers yet. So I was sitting there nervous. I was happy that I relaunched the Voxer coaching pop up and he said to me how proud he was. You know, I'm always kind of hesitant. I said why it's such a hard year. Things don't seem to be going that well. In some ways they are, yes, and in other ways it's been one of the hardest years of my life. But he reflected that I'm not trying to be the cruise liner nor am I in that raft. In Pivot, I describe my anxiety at navigating change that I often felt like I was in a raft Sailing the rocky seas of the ocean while everybody else was in a cruise liner. And in that moment, Michael reflected for me and I want to reflect it here for all of you. And that I'm not trying to be a cruise liner. Not in my business and not in my life. But that doesn't mean that we're stuck in the tiny little rickety raft either. Free Time is about being the sailboat, agile and free run by a delightfully tiny team. Now don't get me wrong, I do enjoy luxury experiences, so I'm not going to say no if I'm ever invited on a super yacht. Mostly out of pure fascination of what that experience would be like. And this is not to be confused with what I say in Free Time about stop sailing the sea of shiny shoulds. So you can see I love a good metaphor. If you've been here for a while, you know that about me. This is about sailing the free Time seas. It's about celebrating the choices that we're making. It is about celebrating staying small, prioritizing freedom, sometimes turning money away so that you can do what feels most aligned. If you have the ability to even do that. Which sometimes we don't. Sometimes we need to take whatever comes our way. Sometimes these Free Time episodes are super tactical and practical and I'm giving you the nitty gritty nuts and bolts super thorough systems. This is not that. Today's conversation is more of the Free Time philosophy and specifically a permission slip to run your business in a way that makes you feel alive. I've described a little bit of what sailing the Free Time seas means to me. What does it mean to you? Ever since that really tough week I started writing. It was the only way I knew how to process everything that I was feeling. The pressures of being a business owner and a breadwinner and having come through the last few years, I didn't know what else to do with myself. I started writing on days where the sky was completely filled with smoke. Midtown Manhattan looked apocalyptic. It was coming from the wildfires in Canada and the outside matched how I was feeling on the inside. There's a song from the Hamilton soundtrack called Writing My Way out and it comes to mind as I've been doing all this personal writing. Now some of you already know about this because I very shyly planting little seeds with my secret link and I'll tell you here as a thank you for being here. It's freetime.com secret right now. Only BFFs in the private community and very close friends know about this. But if you're here in the pod and you made it past the intro, I consider you part of the inner circle. I'm sure I will make a bigger announcement at some point, but right now, this creative process, the most personal writing I've done in probably 15 years, since my early days of blogging. I'm not ready to blast it out to the world yet. A funny related story. When Michael and I got married at City hall, it will be exactly five years ago this November, we didn't post a single photo publicly. Not on social media, nowhere. It was such a special moment that we didn't want to blast it out to the random intranets. We didn't want anybody to know these closest details of our lives if they weren't part of our inner circle. And it was also fun to surprise people. It was fun to surprise friends who we hadn't caught up with in a while by sharing the news in person, because nobody knew until we told them. Anyone who had been reading my work at that point, it would have been at least 10 years. Some of you have been here for which I'm so grateful. Knew that I was always single. Single, single, perpetually single. I was never even the bridesmaid. Like always the bridesmaid. Never the bride. No, I was never even the bridesmaid. I attended every single wedding in my 20s. Single, single as a Pringle, as the kids would say these days. So anyway, it wasn't until a few months after we got married that I dropped the news quietly into a podcast episode. Halfway through. It wasn't a big announcement, it wasn't the headline of the podcast, and it wasn't in the show notes. So there was no fanfare. It was a way to say that if you are here listening and not just to the first five minutes and not just skimming the show notes, then it's information that you can be privy to almost as my way of saying thank you. And not that you care so much about what's going on in my personal life, but it's a way that, as my friend Jonathan and I were just talking about for his Sparked podcast, a way of lowering the stakes a little bit that I didn't need to blast it out across the whole Internet or make photos of our wedding Google searchable. I didn't want that. So after these big business shakeups this summer, you know, I'm starting to plant these seeds just like I did with that one, just ever so slightly. For those of you who are so wonderful to be here, to be listening and in fact. So this is part of the. Well, I'll give you the next clue, the next reveal of the secret project, that it's a secret substack. And funnily enough, in the post that just went live yesterday, at the time of this recording, I included a wedding photo, the big one, the one that I love the most, and I put it just below the paywall line. So it is the first time in five years that I've posted so much as a wedding photo and still it's beneath the paywall because this is a paid project. It's a paid substack so that I can keep my most personal writing for those who are most committed to read and receive it and will benefit from it the most. That's as much as I'm going to say about the project now. You're welcome to go check it out. It's freetime.com/secret. The point that I'm trying to make here is that you have permission to run your business and run your life in the way that fits you best. And part of the reason I'm planting the seeds for this new project is that I feel alive and I feel so uncertain in my business this year in some ways, and yet more alive and delighted and connected than I have in years. There was something so freeing about just having clarity, even though it wasn't necessarily the answers that I wanted at the time. Maybe it's what I needed to be let loose, to have a new part of my creativity and my spirit and my self expression unlocked. And that's why Michael has been calling me his little pirate. And that's just something he's been saying. He said, actually, even though this news seemed really disappointing and it felt like a punch in the gut, you, you seem happier, you seem freer. And neither of us were really expecting that. So if we go back to this sailing metaphor of sailing the free time seas, you could think about three metaphors because again, you know, I love a good metaphor. There's the cruise liner that might be bigger companies, organizations, the sailboat agile, small businesses, delightfully tiny teams. And then there's the raft. Maybe a struggling micro business where you don't have anybody supporting you. I would say the raft is where the burdensome bees come in that I talk about in free time. Bored, bottlenecked, burnt out, buried by bureaucracy. If you're getting beset by the burdensome bees, it might be the case that you need some support. Because that's when that raft feeling is so uncomfortable. When you're paddling furiously you're exhausted. But if you stop paddling, there's no movement. There's no one to help, there's no one to take over the night shift while you need to sleep. So I talked about the Goldilocks principle of team size in the book, but let's talk about the Goldilocks principle of the vessel that we're in, the actual structure of the business itself. You might not want to build a massive superyacht or cruise liner with thousands of employees and complex structures and needing to have all the mechanics and engineering just so. Even Jeff Bezos, one of the richest people on the planet, just purchased the world's largest wait for it. Sailing yacht. Even he didn't want to buy the mega superyacht luxury. He wanted a sailing yacht. His is called Koru. I'll put a link in the show notes, if you even care. But the point is, he has all the money in the world and still he wants a little more sense of adventure. My upstairs neighbors here in New York City, they retired halfway into the pandemic and now they're spending the rest of the summer sailing. They are so free. One was a doctor, one was working in administration in a hospital. They worked so hard and they doubled down when the pandemic hit and the hospital and the organizations needed them and they put in work around the clock now that they're retired, they are tanned, they are glowing, they are free. They're out of the city, they're on the boat and there's wind in their hair. You know, there's wind in their actual sails. It's incredible to see.
We'll be right back just after this.
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So that's what's possible with the sailboat. It's that sweet spot for you. It's totally for you. Of size, flexibility, structure. Yes, it's a little more sturdy than a raft. You can navigate through calm waters or weather storms, but you have a sense of lightness and agility. Because you're small, there are benefits to that. You can make decisions swiftly and quickly. You do have some resources to invest. My neighbors are always buying parts for the boat. So much like a business. We've talked about entropy before. I'll link to that episode in the show Notes of course things are always falling apart or outdated or old in your business. Of course they are. Just like my neighbors are always having packages come with their name on it of odd shapes and sizes and weights. I know they're usually boat parts. Yes, you're going to be fixing things, but you have the skills to do that and to fix one little part at a time. And you can pivot quickly to capitalize on new opportunities. Or in my case like I've completely fallen in love with Substack as a software. I was trying for so long to resist my software FOMO as I saw people experimenting with the platform and now I'm a couple weeks in and I'm head over heels and I want to move all my lists pivot free time, this new project, everything over. Cause I'm so delighted by the experience as a writer, yes. And as a reader in the Substack app. So I feel good because I feel so agile in my business and my creative outlets. I can do that. I, Jenny, can make the decision when I want to move off of a clunky business backend ultra complex marketing software with built out sequences and tagging and funnels and in a blink, when I'm ready, when I find something that I absolutely love, which I didn't quite expect to love Substack as much as I do, I can make the move. I can make that call. I know for a fact if I were having this same role in a big company, there's no way I would be able to make a move like this. Once a company reaches a certain size, forget about it, there's all of a sudden meetings to discuss and approval chains and you have to make a case and then you have to make a PowerPoint deck or slide deck software of your choice to make a presentation, to talk about a potential to make a decision to maybe create a timeline and then a project plan in order to do the thing that you might get to do someday until there's a reorg midway through that process and it gets scrapped altogether. So I'm being a little bit extreme, but I mean that was the kind of stuff that would happen when I worked in corporate. There was just no way that one individual could make any decisions like that at that scale, unless maybe you're super, super high up. So these are some of the benefits of the sailboat. And I think it was just so freeing for me to realize and remind myself yet again, because I need reminders just like everybody else. Hey, you're not trying to be a cruise liner. I'm not trying to be a super yet. I'm not trying to teach you how to make billions of dollars. Michael. And I saw these clips on YouTube. It was actually a compilation of people saying very ridiculous things about how many billions of dollars they were on track to make. And we just shook our heads. We're like, who are these people? And what is this obsession they have with amassing these massive resources in a certain amount of time before they're a certain age, and then kind of trying to sell everybody else on this image that they have? It was just wild to see. And these are obviously very exaggerated. But there's a reason that people were so fascinated by the Titan vessel. That was relatively recent and quite tragic, actually, how much attention and resources the Titan vessel, with a few billionaires in an untested piece of equipment got when their vessel was lost. Before we knew that, it had exploded undersea in the deep water as they tried to go look at the Titanic. And there had been a ship off the coast of Greece that had 600 migrants who were struggling and who didn't get nearly the support and attention and resources in that contrast. It's heartbreaking what happened to the migrant ship with the Titan. It was almost this schadenfreude story of hubris, like Icarus flying too close to the sun. But in this case, they were swimming too deep to the bottom of the ocean. And you could tell that as experts weighed in on the vessel itself, that it wasn't built for that. It wasn't properly tested. It wasn't properly vetted. There was a lot of hubris invol. And so I think it's obviously tragic any way you slice it if anybody dies. But people felt more irked by their situation because it was all voluntary. And it was like these people who have so much and yet they're still pushing to the limit to where they're putting their own lives at risk for what? So I would just say, if you're here, you're not trying to be the Titan vessel either. It's okay not to have to constantly try to be the best, the first, the most, the greatest. It's okay. What if you're just having a blast and you're tanned and you're watching the sunrise and the sunset on your sailing yacht. And it's small and delightful and joyful and easeful and agile. And yes, you're going to work. I'm not even. The funny thing about this whole topic and metaphor is that I've never done a sailing sojourn. I had a friend, Tori Desroche, who she met a guy in a bar in San Francisco. This was when we were back in the blogging days. And they ended up sailing for two years. Despite her deep, deep, deep fear of sharks and water, she still said yes to this guy. And they ended up two years on a sailboat. And she wrote a beautiful book about it. I'll put it in the show notes. Oh, my gosh. I remember following that journey and just being so blown away by her. So I've never even done anything like that, but I could say that of course you're going to work hard when you're on a sailboat. You will. If you want to have a couch potato view of this like I do, you can watch Below Deck. It's either through Bravo or at this point you can get it through Peacock. But you could watch Below Deck, which is with these charter guests on these gorgeous super yachts. But then they also made an addition called Below Deck Sailing Yacht. I forget the exact title where you see that, okay, the crew has to work a little harder, the crew's a little smaller. It's a different experience. So to each their own of what experience you're going for. And if you're running a sailing yacht, you're not the passenger that's totally free and kicked back on the super yacht. It's just a different experience. So I think part of this is just giving ourselves permission to acknowledge where we are, acknowledge where we're trying to go, and acknowledge how we like to get there. To stick with our water and water vehicle metaphor. I remember while I was working at Google, my friend Julie and I took a yoga river rafting trip with one of the teachers who was teaching yoga at certain nights at Google. And this was in Oregon. I forget exactly which river. Oh, gosh, don't be mad at me if you live in Oregon. And I'm just forgetting the name, but I remember they would give us choice. So yes, we would do yoga twice a day. We slept in tents. It was really fun. And Julie's super active and athletic and she always wanted to be in a kayak going down the rapids. Class four, class five. There's Julie in the kayak. Even now she does Olympic lifting and she's so impressive, has been doing CrossFit for almost a decade, if not over a decade. And for some reason I just didn't want to do that. So I spent half the time laying on the back of this, like, pontoon where one of the guides was carrying all the luggage. And I was just like tanning on the back of the boat doing nothing at all. I was not even in the exciting raft where we're all paddling. I've done that before. My dad used to take us in the summers. But that week what I needed was to kick back and relax and do nothing at all and be totally taken care of. And it's just funny because that's an example where maybe that experience would have driven Julie crazy. She would have had FOMO for the adventure of the kayak in the rapids. But what I needed at that time was to do nothing at all and just feel completely pampered. So it makes me laugh because there is no right or wrong. I mean, maybe if you're listening, you could judge. I feel self conscious. Don't judge me that I wanted to sit on the back of the boat and do nothing. And sometimes I do wish I was a little more like hardcore athletic. It would help me right now because I've definitely put on a pandemic. Embarrassing number. Who knows the precise number, But I have a pandemic pudge. Let's say that this is all a tangent. The point is that if we can give ourselves permission to be agile and embrace how quickly we can make decisions, how adaptable we can be, how scrappy we can be in terms of resources, how we don't need to grow at all costs, we don't have to scale beyond what's joyful to free up even more time. And that we do have room to take some risks while not being in as rickety a structure as the raft. That there's so much to celebrate. Michael's comments to me that I opened with put the wind in my sails, so to speak. How could I resist? And I even asked Chatgpt for some good boat names. So our two favorites were Sail la Vie. And I also appreciated Not a care k n o T. So I hereby grant you permission to join me as a little pirate on the rocky business seas that it's okay if old structures burn away, the boats burn. There is an aliveness to be found, a renewed sense of freedom and expansion and lightness. If you can embrace some of this. I'm not saying we want too much more tumult and none of us want to be nauseous and vomiting because of, you know, how rocky the ride, but channeling your own waves of emotion and insecurity and challenges and uncertainty into being present and celebrating what we are building and what we've already built and how far we've already come. So I have to admit, even though it has been one of the hardest years of my life and of my business for sure, I definitely feel a lot lighter and freer too. And I would wish the same for all of you. Thank you so much for listening. Have a beautiful rest of your day.
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Thank you.
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