018: Workcation in the City
8 Dec 2025 · 19 min
Host Jenny Blake describes a three-day "workcation" (staycation in the city) as a focused, restorative strategy for doing high-level creative and strategic work. She covers why to invest in a comfortable room (mentions Soho House, Meatpacking District, Manhattan), how to structure short sprints (two–three days), packing and comfort tips (cozy clothes, supplements, journal, mic), and points listeners to a two-day Strategy Sprint template and the Free Up Founder Time mini-course in the show notes.
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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.
Hello friends. I hope this episode finds you well. How are you doing today? I am just wrapping up a three day workation back on the Pivot podcast in episode 250 I described my very first experiment or pilot. It was episode 250 called Staycation in the City. If you live alone, you probably don't need to do a staycation or a workcation, but then again, you might just find it helpful and inspiring and the antidote you need to get out of the Groundhog's day of staying at home and working in the same routines. I find these workations to be particularly powerful to work on my most creative strategic work. So in this episode I'm literally squeezing this in with 30 minutes to go before I have to check out. I promised myself I would do a solo episode and here I am at the very tail end. I've been kind of playing hooky on the podcast by working on the book, so at least I've procrast diversified or divers procrastinated where between day to day stuff in the business book and podcast. As long as I procrastinate on one with the other, it's okay. It will all move forward somehow. There's also, go figure, construction in the background. So my perpetual quest to find a quiet environment for podcasting lives on. In fact, I recorded three episodes in a batch yesterday and there were jackhammers in the wall next door. It could not have been any louder. The only question will be how much of that sound did the mic pick up? So those episodes may have aired already by now. Maybe not. I just hope you continue to give me some grace while I solve the podcast sound issue. There's this aspiration in my head of this perfect sound quality and then reality. And my next experiment will be renting an actual audio studio here in New York. But they just don't look that comfortable. They're these really uncomfortable tables and chairs. And in order to make that worth it, I would want to do a few in a row. So there you are in a windowless room. There's not a lot of oxygen. I don't know. Reminds me of recording the audiobooks for Pivot and Life After College. It's like two days of. I can't call it torture because I. I do enjoy it, and I work pretty quickly on those. But nonetheless, I keep hoping for some cozier environment. All that said, the staycation or workation in the city can be very re energizing to just, as I said, be in a new environment, but also to make the commitment to yourself of what you're going to work on.
This is now my third staycation, or I'm calling it a workcation, because in my case, I'm actually committing to doing my most strategic work. And I had a friend who also runs his own business ask me, you know, how do you justify the cost of that? And don't get me wrong, I already asked myself that question. I have a raging inner CFO that is very frugal and cost cost conscious. And I've always been this way where I kind of want to earn the rewards. And so sometimes it feels strange, especially on my own dime. You know, pre pandemic, I would travel every two weeks for speaking engagements. And although that sometimes got tiring, what it did do was frequently give me time in a hotel where there's really nothing to do in my room, and I could either decompress, go to bed exactly when I wanted, wake up when I wanted, get work done. Usually I was too wiped out, leading by the travel, leading up to the speaking gig, and then decompressing afterward to do too much. But that really went away from me in 2020. So by doing these workations after the first one, I realized how soothing it was to my soul. And I realized that I was Getting done big 10,000, if not $100,000 tasks in my business. I was moving forward the most important things because I finally had the space and quiet and just that shift in perspective that I needed. So I started to commit that if I'm going to do one of these and I don't skimp on the room either.
This is another element where I kind of felt like, okay, well, should I just go for the smallest, most reasonable room I could Realized that no, it's actually important to have a big room, bigger than I ever felt comfortable paying for, for just my own personal travel, so that I could have a couch and a desk. Primarily.
In this case. Today I'm staying at the Soho House Hotel in the Meatpacking district of Manhattan. And I have a big room. There's a whole couch seating area, there's the bed and there's a desk and there's even a little couch. Chaise lounge by the window for reading the newspaper in the morning.
Now this size room is bigger than the studio apartment that I lived in in New York City for six years. I was kind of laughing to myself about that the other day, that as soon as I got into this room and I looked around, I thought I lived in a tinier space than this for six years. Two of those years with Michael, while we were both working from home. That was our pre pandemic boot camp because we both lived and worked from home in that studio apartment. We didn't even have a bedroom door. We did that for two years, 2017 to 2019. And then we moved into a bigger place, three bedroom, where we each have an office at the beginning of 2019. So if nothing else, that set us up for what was to come. And we moved right after we had gotten married too. So we remember feeling like, oh, the first year of marriage is so easy. But mostly it's because we weren't living in this teeny tiny space. Especially with different schedules of him being a night owl and me being such a morning person. How does that tie into this workation, you ask? Well, for one thing, if you live with other people or you have responsibilities at home, of course your partner needs to be generous enough to give you this space. But hopefully it benefits all parties involved and you come back refreshed and productive and happy and everybody wins. But it can be really nice doing a workation to get into your own rhythm. So anyone who knows me well, if you've been listening to the podcasts for a long time, you know that I keep grandma hours. And if left to my own devices, I am in bed by 7:30pm I am asleep by 8. Okay, I know that that sounds insane to some of you, but I crave the early morning hours. I get FOMO for not being up at 5am when it's pre sunrise and like the world is quiet, I can just read. I don't feel any sense of guilt or that there's something else I should be doing that is my time. I know that certain Night owls love the late night for that same reason. They feel just the opposite. Okay, everyone has gone to bed. Now it's my time. No one's gonna bug me. And even if you know, of course, this is all a mindset of who's bugging you and who isn't. But there's just a sense, I think, when the world is asleep, that it's talk about free time. It's just true free time. So one of the most fundamental things about these workations is getting into one's own rhythm of sleeping, eating, exercise, and working. In episode five of Free Time with Emily Hayward, she made a very astute comment that she's hoping business owners can see brand as an investment, not a cost. This is how I see these workations. Whether you do them once a month, once a quarter, twice a year, it is time to do a strategic sprint. And if you can go into them seeing it as an investment, not just a sunk cost, then the whole perspective changes. Instead of feeling guilty or self indulgent, which again, those are like prominent on one shoulder, on the other, on the other hand, on the other shoulder, I know there sits a little work angel who's saying, this is an investment. And when I can go into these three day, I've decided so far, three days is pretty reasonable, three nights, half day on either end, that when I go into this time seeing it as an investment, then I can very directly tee up going in exactly what I want to work on. I may not hit everything, but I can say if I make meaningful progress on these one to maximum three areas, then this investment will definitely be worth it. So in my case, this time, where I'm recording this right now, I went in knowing that I wanted to work on the book, that it will be related to this podcast. I don't know the exact title yet, or even timing, so you're getting in on the earliest, earliest stages. But I can go in saying if I make meaningful progress on the book, if I can batch record, I did, in this case, three interviews with podcast guests and at least one solo episode, here I am recording that now, then it's a win. And if I can come home rested and recharged and just psychologically refreshed to get back into the day to day of my business, business and the day to day of the household and managing everything, then, then that's a win. Then I feel really, really good about it. And I've started to see these workations as oxygen, as like I said earlier, fuel for my soul. Just, just my friend called it hug. Like she said, it's like a hug from your hotel room. Not everybody likes hotels, but I think if you can experiment and find the right type of place, maybe for you it's an Airbnb, then you can start to sink in and it becomes this hug, this way to shift your thinking and really have that self care and that grounding and recharging that so many of us need now more than ever. I'm also going to link in the show notes to a two day Strategy Sprint template. This is something that I piloted with my team back in 2019, which was really designing up front how those two days were going to go. Now some of you may want to enter into a two or three day workation or staycation just totally free. And maybe the point is that you have no plans and no ideal outcomes. The goal is just go, be yourself, unwind, relax. If you are coming in with the idea of making a time and money investment for some kind of ROI in your business, some kind of return on that time and investment, you might find it helpful to think through what we've outlined in that two day strategy Sprint template. So that will go in the show notes and you can also run it as a decision making Sprint. Maybe you're not going to be producing a lot of output, but you're going to go in and really sit with some big beautiful questions in your business. Or in the case of a big creative project like writing a book or launching a new podcast, maybe you need to really get quiet about who it's for and how is it going to be different and what is your unique thought leadership that you're bringing to the table. It's not easy to do those things when you're trying to cram them between meetings or answering emails. It can be really hard to elevate to that level of perspective in your business while you're operating the day to day. And of course that's exactly what the Free Up Founder Time Mini course will teach you how to do. So if you haven't taken that yet, go to itsfreetime.com foundertime and I'll put that in the show notes as well because because that's about how do you carve out that time on a week by week basis so that you can work on your business, not just in it, as Michael Gerber would say. Author of Revisited. We'll be right back just after this. 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The last category that I want to cover in this episode and then I'm curious if you have any questions. I would love to know if you there's anything on your mind about this setup that I've been experimenting with. The last thing I'll say is what to bring from home to make this easier so that I don't dread the packing and unpacking as much. I am trying to just keep a travel suitcase mostly packed. I always keep a second set of toiletries in their own in in the suitcase as well. And I even keep certain supplements like brain octane, magnesium, calcium, zinc, you know, daily electrolyte thing. I just have a few little supplements, not too many. I'm really not a supplements person. I'm really into placebo supplements. Like anything that I take as long as I just think that it will, you know, make me feel healthy, then I'm I'm game. But keeping some supplements, I realized that it was really nice to have fuzzy slippers, which I forgot to bring the last time. I love having cozy sweats, so I got these amazing cashmere sweats from a company called Dunt D Nadam N A A D A M I think I'll put it in the show notes and they're not too expensive, but they're just so cozy. I love comfortable soft fabrics and sometimes I'll pack for a trip and I realize, I mean this is for the ladies listening, but it's like I only have really tight yoga pants, something that is just not that comfortable for lounging around. So. So if you're gonna I mean, aren't we all like in loungewear 247 now, especially below the computer screen where no one can see on Skype and on video. But invest in a pair of joggers or sweats that you just feel super cozy in that you can lounge in. I bring copious reading material. My reading eyes are way bigger than my available time or reading stomach, if you will, to keep with that metaphor. But I bring like a huge stack of New York Times clippings that I want to catch up on. In this case, I probably brought 10 books, not including what's on my iPad. And I got through two of them. But yeah, I love having options. I love just having choices about what I'm going to read and how I'm going to feed my mind while I'm here. Can you hear that? There's the construction starting again. Oh well, onward we go. I also bring my journal, of course. And because I pre ordered my friend John Lee Dumas book, I'll put our episode with him in the show notes. I got his Freedom Journal and I have to say I've been doing it for 40 days now and I'm really enjoying it. There are certain things about it that I don't follow. Like I'm not that into smart goals and certainly not on like a day to day basis. They're just, they're too smart for me. They're like too intense. But I love the daily reflection that this Freedom Journal inspires. So I'll put that as well. No attachment, no affiliate thing if you get one. I'm just saying I, I bought it. I got it as a pre order bonus and it's been really fun to guide these. He does 10 day sprints with reflection in the morning and in the evening. I'm looking around. Oh well, I brought my podcast mic. So if you want to bring any equipment that you need to do your creative work. So maybe my friend suggested this. I have a couple friends who pack a candle, shout out to MBS and Petra and Sarah. I always forget to pack a candle, but that can be a really nice way to personalize a hotel room and make it feel more your own. And then I like having music. Not every hotel or hotel room will have a good music player, so if you have a little speaker you can bring, that's always a nice touch. And I really think that's it. I don't think everything else would be obvious. It's really hit or miss if the hotel has a good enough coffee machine or not. So I know a lot of people Travel with the AeroPress. These are some of my basics. I did a pivot podcast a while back on how I travel and what I travel with. It was in the before time, so I have no clue how relevant it is. But I'm going to throw that into the show notes too just for good measure so that in case I missed anything in this solo riff off the top of my head, you'll have it. To wrap this up, I will leave you with an inquiry. What could you do or create or how could you even unplug and decompress if you were to carve out two or three days for yourself.
Where would be your ideal place to stay? Do you want to get on an airplane or do you want to try to find somewhere local? Do you want to do a hotel room or do you prefer to do Airbnb?
What type of support would you need to get from friends or family? Do you need coverage for taking care of your pets? Do you need a partner's permission if you live with someone to just say yes, it's okay, I've got you, I'll take care of the things on the home front. What would be your aim of this workation? What would you love to achieve or work on? And again, rest is totally fair. That is plenty. Finally, how much budget could you set aside? So what would be the range that would allow you to get a big enough, comfortable enough work, friendly enough room that could still fit your budget? And so what would you need to achieve based on the areas that you mentioned in order to feel really good about investing that money?
And I know I said that was the last thing, but maybe one more look at your calendar now and see if you can already carve out a week somewhere. Even if you don't go away for the entire week, it's not that fun to come back to a whole day stacked with meetings. So try to carve out a week on your calendar right now. Even if it's a month or two out that you are going to plan your own workation or staycation, that is your time, add it to the calendar, don't let anybody take it and don't give it up yourself if somebody asks for it. Unless it's a really high paying client or something like some gig that you just can't say no to and then report back. I would love to hear how it goes. I would love to hear what you work on. And if you are someone who already applies this strategy. I know there are really famous authors like I think Cheryl Strayed, I even think Maya Angelou. They both did this hotel strategy. I've heard it multiple times from people. I even heard it once today. Oh, Rachel Rogers who just has a book coming out. She also would go book an Airbnb in her local town anytime she needed to do writing. And she would write her book in batches because it was easier for her than writing day to day. Get creative. I would love to hear how this goes. You can always leave a voice note that I can play in a Future episode@itsfreetime.com ask. Thanks so much for listening everybody. Have a beautiful rest of your day. If you've listened this far, you get a gold star. Thank you. Word of mouth is the most joyful way we can grow this show, and it helps us land interviews with the luminaries and insightful guests that you would most love to hear from. Please send this episode to a friend who might find it helpful, and for show notes and related links from this episode, visit itsfreetime.com while you're there, make sure you're subscribed to the Time well Spent newsletter. You'll get instant access to my Tech Toolkit, a continually updated list of all the software I use, along with the total monthly spend. To run my business where no one works full time, Even me, visit itsfreetime.com join Remember, you are running the show. It's time for radical reimagining and everything is up for grabs. Let it be easy, let it be fun, and build with love.
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