250: Staycation in the City
8 Dec 2025 · 19 min
Jenny Blake narrates her experience piloting short "staycay" (staycation) hotel stays in New York City during 2020 to get focused work time, rest, and creative energy. She describes two multi-night hotel stays used for virtual events, high-level thinking, and renewal, offers practical tips (HotelTonight app and promo code JBLAKE9, TripIt), and reflects on how brief hotel retreats can be budgeted as business ROI or personal restoration.
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What's next? This is a question we're all having to ask and answer more frequently. I'm Jenny Blake, your host of the Pivot podcast and author of Pivot. The only move that matters is your next one.
For show notes from this episode, visit pivotmethod.com podcast if Change is the only constant, then let's get better at it. Here we go.
Hello friends. Good morning. It might not be morning for you when you're listening to this episode, but it's morning for me. I'm recording this at 7:30am in a hotel room in New York City. I'll explain more about that in a moment. As per episode 245 on Radical Reimagining and Pushing Past Perfectionism and episode 246 on what's yous Job Today? I committed that my job today is recording a podcast before I do anything for anyone else. So my job today will be getting my thoughts down on audio paper recording this episode here, even if I have morning voice because you are the first person I am talking to today.
Ah. So let's get into today's sort of strange episode. I really debated if this is just TMI or if it's going to be a helpful sanity saving strategy for some of you during these crazy times.
This is the second time that I've piloted a staycay in the city in 2020. And I'll tell you a little bit about why I'm doing this and then some of the perks of doing a staycay at this time. Fun fact. Did you know that Cheryl Strayed also has given the advice? She said if you have small children and the money, hotel rooms can be a good place to write. She got Wild written by checking into hotel rooms for 48 hour stretches where she would her famous quote write like a mother ever. She doesn't write every day. She calls herself a binge writer. So by her checking into hotels and I've heard of actually many other authors who do this, I'm not here to write, but I am here to get some really quiet uninterrupted focused time. In both cases, the impetus was a dinner invitation from my dear friend Dori Clark. And Dory lives at the opposite end of Manhattan from me. So it's about a 45 minute commute. When I got invited the last time, it was right at the end of summer. I just thought to myself, you know, I want to relax. Dinner is so joyful for me. It's one of my favorite things on the planet. It is one of the things I love most about New York City and one of the things that's been really sad to lose during a lot of 2020. Although now I'm so grateful for every restaurant and coffee shop that's opened up for Al fresco dining. This is how I love to connect with friends. Just a small, intimate dinner. My friends Julie and Ina and I used to go to a different restaurant every Friday night. And this was the thing I would always look forward to. So when Dori invited me the last time, I had two meetings in a row. So I had dinner and then the next night I was going to need to be right back downtown in the exact same area. Add this to the compounded problem of not getting nearly enough sleep, being in major sleep debt from the craziness of summer and all the factors I talked about in episode 245 and I just had this crazy idea what would happen if I booked a hotel room. Is this possible? Would Michael be okay with it? Is it going to be too expensive? Is that a ridiculous expense? I grew up in a family of, you know, frugal, traveling. You don't just book yourself a hotel room and out for nothing. You know, like, don't be lazy. Just get back on the subway and go home. But when you know, you know there's sometimes a little voice in your head that just says, book a room. Book a hotel room. I use an app called Hotel Tonight which allows you to book on really short notice. I highly recommend it. If you don't already have it and you've never done a booking, you can use code JBLAKE9 and you'll get $50 back after your first booking. So that's J. Blake9 and the app is HotelTonight. I have used this app for many years and here was what surprised me most. So Michael gave the okay. He said he would take care of Ryder. Another factor during those two days was we were launching our first ever Momentum member led virtual summit. And this was two days jam packed. I was going to be on Zoom all day from 9am to 4:30pm and I thought, you know, it would be nice to be in a hotel room. This is the first. I need to be really focused, have a quiet space, run this summit. The summit was a huge success and I had so much fun doing it from this hotel room downtown. So Michael gave the okay, I booked the room on hotel tonight. And I'll tell you another aside. I used to in my earlier travel days just only book on price. And even when I would be traveling for speaking engagements again, I was kind of raised this way. Just always look for the best deal. Find a hotel in the category of solid or good enough. But my friends, I am a Libra and I love luxury. Michael makes so much fun of me for it because he's like, you're that girl that you like champagne and. And I love a luxury hotel. I love it. Like there is something soul stirring for me about a luxury experience where I come in and I just feel so taken care of. Everything works. It's not shitty hotel room coffee, it's an espresso machine. There's plush bathrobes, there's a desk to work at, there's a chair to sit and read at in the morning. The proportion of joy to cost. Over the years, I slowly came around to realizing this is worth the investment for me. And now that we're in 2020 and travel is so restricted hobby hotels have never been this low in terms of price. So I stayed at a luxe hotel. That's how HotelTonight categorizes it. Down at the South Street Seaport, that's by the water, not on the west side, the west side of Manhattan where you could see the Statue of Liberty and you see New Jersey, it's on the other side where you look over at the Brooklyn Bridge and Brooklyn, of course, and it was like $150 a night. Now I know that that might still sound cost prohibitive to you or kind of ridiculous. Our family is making do with a lot less this year. So it's not like, oh yeah, I'm having the best year in my business anyway. You can tell I'm not obsessing over the money. I really have faith and trust and abundance and all of that. But what I'm telling you is it's not like oh yeah, we have so much saved up. This is a no brainer in terms of my sanity, in terms of recharging, in terms of focusing. And what's my job today in that first pilot run of a staycation in the city, that was my job, was running the Momentum Summit and going to these meetings and getting a good night's sleep.
So for 150 a night I ended up extending for a third night. Again, Michael gave the okay and it made such a huge difference. So much so that in my little friend tour mastermind group, my friend Sarah said, your hotel self is completely lit up and energized and maybe we can do some coaching around hotel self Jenny. And then your day to day of what your experience has been back at home in 2020 and how can we work to close this gap. And then I had some other friend tours in that group. They said you gotta double down on this. This brings you so joy and you're productive and you get rested and don't feel guilty because I was saying I feel a little guilty for a number of reasons and that's just my tendency. But they said no, if anything I want to see you do this more. So sure enough, when Dori suggested another dinner invite in in addition to hotels, I mean now you can get reservations in New York City at the best restaurants. So we ate at Cipriani, downtown Wall street where ever since I've lived in New York, I walk by these like gorgeous columned Cipriani buildings. There's one near Grand Central Station, kind of looking wistfully like when will I ever go there? I don't know. Never made it happen. And we had a really nice outdoor dining experience with a couple other friends and I was so grateful not to commute back home. It was like a three hour dinner. And so this is time number two at the time of this recording of a two day, two night staycation downtown staycay in the city. And I committed this time around to doing very high level thinking and meetings. Now I'm not apologizing for the expense. I think getting rest is so vital that in terms of episode 246, what's your job today? If you just said my job today is resting and relaxing and doing nothing at all and having no responsibilities, I think that's amazing. In this case I wanted to try to associate, okay, kind of almost like the Cheryl Strayed quote. But I didn't have that in mind. I only looked that up when I was recording this episode. How can I connect these 1, 2, 3 night hotel stays with really high value, high revenue producing work, brainstorming creative conversations, creative ideas, solidifying big important things in my business, then it really makes them a no brainer. And not only is, let's say a total stay, I don't know, 300, $400. Not only is it A tax write off. But I could directly map those funds toward ROI in the business. Again, this is not required. I don't think that if you need to do this for your sanity in your city, wherever you are, I don't think that you should have to tie it to revenue. Neither should I. But there's something very motivating about that. It's inspiring. It's like, okay, you want to give yourself this luxury, restful experience. Well, now with this time, what do you want to do with it? And I'm finding it very energizing to put my mind on the big stuff. And then that also creates more space for me when I get home to feel relieved, like, okay, I carved out this pocket. And yesterday I had two virtual speaking engagements. I was helping my friend Laura kick off her book launch for her new book find, you'd Zone of Genius. I highly encourage all of you to grab a copy. She is so good at what she does. Her zone of genius is helping people find their zone of genius. It's really incredible. And she even talks about how it ties into your core emotional wound can become your purpose and often does. So your core challenge in life or when you're a kid becomes part of your purpose. And that combines with your zone of genius to be a really unique factor in your day to day work. So I had her book launch and then after that I was doing a panel for the American association of Literary Agents. And these two events are part of what helped me not again, not justify staying in a hotel, but okay, I'm doing two professional events. I'm presenting, even though I'm not traveling for those in the past. In fact, in February I released an episode, I think it was 1:55 with Grant Baldwin on being a professional speaker. And we were talking about how many miles we put in every month, every year, had no idea what was coming. I recorded that episode with him in a hotel room in D.C. after doing a Q keynote at the IMF, the International Monetary Fund. And we're getting out our TripIt app and looking at our stats and can you imagine like one month later, all other speaking and all other travel would get canceled and be no more crazy crazy. So with these staycations, especially when I wrap it around high level strategic thinking and virtual events where I am presenting, they it kind of reminds me of when I was on the road for keynote speaking. I'm a super introvert. If you've been listening here for a while, you know that that's not news. I need to. When I'm Gearing up for an event. I need quiet and time to just charge, charge, charge. And then I do the event. In this case, it was two pretty close together in the same day. And then as soon as they end, I love it. I'm so proud. I'm so happy. I feel very fulfilled. But I don't want to talk to anybody. It's such an exertion for me. And again, in a good way, in a way I really love, But I don't want to talk to anybody. As soon as it's over, I just want to have a bite to eat, read, maybe listen to a podcast, watch a TV show.
And then go to bed. So even Michael, of course, we're going to check in at the end of the day, but maybe it'll be 10 minutes instead of an hour. And I'll say, I just gotta. I just gotta stop talking now.
So connecting. If you're leading a virtual event or you're, let's say, invited to be on a panel for a virtual virtual event, why not replicate the travel that you might have done in the. Back in the day, I sent my friends the most hilarious photo. Well, I think it's funny in a nerdy way of my setup in this hotel room. Some hotel rooms are better for, you know, having a good virtual background than others. In this case, this room has a desk. And then it would only show the bed. And I think that's super awkward. If I would be on a panel and all you can see behind me is a bed. That's really strange. So this. This hotel room has these beautiful watercolors of books on the wall. It's perfect for a book launch, a virtual book launch, and a panel for the association of Literary Agents. Wow. But in order to achieve that backdrop, I had to put a shawl that I brought over the TV and make it look like that was some sort of fabric wall art. And then I had to grab a side table, turn a trash can upside down, put a stack of books that Dory had given me, put the laptop on the stack of books. And then on the table, I put my external fancy mic that I'm recording this on in the ice bucket on top of the tissue box. Okay.
You might be having a hard time picturing this, but I used everything at my disposal. I even had to put a book underneath the coffee table so that this whole setup wouldn't be crooked, upside down, trash cans, the ice bucket, the tissue box, the side table. But I crafted this really nice.
Backdrop. Hopefully, no one was the wiser. I mean, they probably know it's not my home, but I don't think you would for sure. The other thing is that when I've been checking in and I've only done this twice, I look forward to more when I've done this. When I check in, I say, and just so you know, you know, I'm presenting twice tomorrow, or I'm presenting all day tomorrow. If you happen to have a room with a desk that has a nice backdrop, that would be super helpful. And I don't think that this hotel today, I don't think he really cared because this room is pretty small. But every now and then it leads to a nice upgrade where they think, oh, oh, you're actually doing something from the room. You're working from the room. Let me help you get a nice setup. And so it could lead to an upgrade.
I'm curious, could you do this? If you could do a staycay in the city, would you want to stay in your same city? Would you want to go to a neighboring city? What makes your soul sing?
Some of you, you know, you may have responsibilities that you just can't leave for even one night. I totally get it. Maybe you can do a staycay or an adventure that's a day long. You go make a commute somewhere. Now, I know some of you, you may still feel very nervous about COVID I have to say, in both cases, both hotels were highly conscious. Even the fine dining at Cipriani, you walk in and at the table in the entryway before you even get in to talk to the hostess and say you're there. There's masks laid out just so there's a bottle of hand sanitizer. There's everything you need. And everybody wears the masks within the restaurant. But when you're at your table, you can take it off. The hotels feel super clean. They don't have housekeepers come in every day. You have to request if you want anything during your stay, just I think, to respect them and. And whoever's in the room. So there's not a lot of interaction. And then you just wear a mask in the public space. So in case that's on your mind during this topic of this day, K in the city.
For some reason, that just. That just hasn't been a factor for me. I think it's more important, as I talked about in episode 246, to really focus on health, health and wellness and getting rest and keeping our immune system strong.
So, yeah, where would you go? What would be your budget? What could make it a worthwhile roi. Whether it's something priceless like renewal or something directly tied in to your business or creative projects, Would you want to pair any social outings with them? What could this look like? The apps I mentioned, Tripit Pro is worth it, but when people can travel, the upgrade is worth it. But I mean, right now it's probably not as relevant. Again, with HotelTonight, if you use code JBLAKE9, you'll get $50 back after your first booking. So maybe that will make this a little more doable, will up your budget. And the other thing I wanted to add, because I forgot to mention this in episode 246, is when I say what's your job today? The examples I gave last time were so serious. Health, wellness, working out.
Recording a podcast, doing your creative work. But your job today can be anything you want. If you want to be what is your job today? Oh, it's organizing my house. It's. It's color coding my bookshelf. It is. I'm like having trouble even thinking of something that might seem frivolous. It's. I don't even know. I don't even know. It's like catching up with friends. Your job. It just the word job. We get to redefine it. We get to recreate it. What's your job today? Means that you decide what is most important to your spirit, that day, that week, that month for that theme, that season of your life. And you hereby have my permission to make that your job today. And then you'll figure out how to fit the other pieces around it. I hope this was helpful for you in some small way or it sparked some kind of creative thinking. Remember from 2:45 radical reimagining means everything is up for grabs. Thank you so much for being here. Listening everybody. And as always, if you want to leave a question or a voice Note, go to pivotmethod.com Ask.
Thanks so much for listening to this episode of the Pivot Podcast. Make sure you don't miss an episode or my insider tips and templates by signing up for Pivot List, a curated twice monthly newsletter where I share the inside scoop on what I'm reading, watching, listening to and the latest tools I'm geeking out on. Sign up@pivotmethod.com pivotlist get show notes from this episode@pivotmethod.com podcast and connect with me on Twitter @jennyblake.
Remember, build first, then your courage will follow. Hasn't it always.
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