138: ⛵️ Stop Sailing the Sea of Shiny Shoulds
8 Dec 2025 · 8 min
Podcast episode (Jenny Blake) revisiting a sidebar from her book Free Time called "Stop Sailing the Sea of Shiny Shoulds." Jenny reads the passage, shares personal anecdotes (disliking social media, managing people, book-launch experiment with a small team), and offers a concrete reflection exercise: audit activities into three columns — Shiny Shoulds (draining obligations), Coulds (possible but conditional), and So Goods (energizing, zone-of-genius work). The episode includes sponsor ads and ends with calls to action (voice memo, BFF community promo).
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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.
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By a landslide. One of the most resonant ideas from the Free Time book comes from a small little sidebar called Stop Sailing the Sea of Shiny Shoulds. For some reason, this phrase when I say it, people stop in their tracks and they go, wait, can you say that again? Stop Sailing the Sea of Shiny Shits. Whether I'm in a podcast interview, whether I'm on stage, even I bring this up at a keynote. People seem to grasp onto this. And it's part of the reason that at the end of every single chapter in Free Time, I write you a permission slip. I also write you one in every single edition of the weekly Time well Spent newsletter. Permission to Stop Sailing the Sea of Shiny Shits. This episode is going to be a shorter one. I want to redo that section of the book just so you hear me again, even if you've already read it, think about it in the context of this year ahead and then I'll give you one of my favorite reflection exercises for how to get clear on what your shiny shoulds are and what you could be doing instead.
From the Book Stop Sailing the Sea of Shiny Shits who benefits from getting you addicted to your phone, to your inboxes, your notifications, to your social media accounts? Unless you're someone who is energized by these aforementioned activities, you are a pawn in somebody else's growth at all costs game. Frittering your attention away does not benefit you, but it very well may benefit the platforms you're spending it on. As the saying goes, if you aren't paying for the product, you are the product. With all the noise online, it's easy to get lost. Sailing the sea of shiny shoulds Some shoulds are an obvious yes or no. Shiny shoulds tempt you. Deep down you know you don't want to pursue them, but you feel lingering pressure and obligation. They're shiny because everyone else is doing it, even succeeding with them. Social media is just one example of a business should. Do you enjoy posting for the sake of posting, interacting and replying? If yes, post away. If not, you have two choices. 1. Quit completely. No regrets. Why post? Why do anything at all if you don't enjoy it? How could the ends justify the means in terms of fractured attention and diminished energy? Why participate in a system that doesn't support you?
Or number two, design this as another business system with a regular process based cadence. No, you don't love it and you know you don't love it, but you cultivate it all the same. Just as you would keep up with monthly bookkeeping or quarterly tax preparation. Now I tried outsourcing the task of social media to software and to team members. Ultimately it didn't resonate for me. It grated against my value of integrity to have other people posting for me or scheduling tweetbots. I was also contributing a little bit to a tragedy of the commons in that I had stopped reading the main feeds of what everyone else was up to. So my post became about me, me, me. And if I, Jenny, didn't have the desire or bandwidth to reply to messages, I was just another person on a soapbox shouting into the ether.
Now this is back to real time Jenny. You may know, if you followed the book launch closely that I had a delightfully tiny team so spearheaded by Stephanie Houston, a founding member of the BFF community who did help with social media during this very book launch. This was a big experiment because being the cranky curmudgeon that I am, knowing that it's a shiny shit for me and it's not even that shiny anymore because I usually feel worse when I put down my phone after engaging with too much social media. I did decide that I wanted to try it out to have their help with the launch, mostly because they were so excited and enthusiastic. Stephanie and her team created a game plan plan and I made sure I didn't want them posting as me. They were always posting as themselves, but they created a ton of buzz and excitement and joy and momentum. The number one word that we used to guide the book launch and all related activities was fun. So if there was an aspect of the socials that they didn't find fun, they didn't do it. Every post that they shared was meant to be fun. Now it did push me to an edge of a comfort zone because I wasn't really keeping up with it all. I still wasn't very invol and I was a little nervous about what would they be posting. I did start getting texts and more activity coming my way from people seeing but that's also part of the goal of a launch is creating visibility. This was an experiment that I did that was a once in six years of launching a book experiment and I think what was helpful what helped it be successful was a Orienting around this phrase fun b Engaging with a delightfully tiny team. That's Stephanie Houston and company. I'll put the link to her site in the show notes and knowing that it had a fixed start and end date in a way you could say that that's a hybrid. So I just read you from the book itself that you could stop doing the shiny sheds altogether. You could operationalize them and maybe option number three is have a short term window where you're going to try and experiment with a clear start and end date and then you can clearly measure not just did this improve book sales, did it grow important metrics in your business, but also measuring the impact on your wellbeing as a business owner. Does it contribute or does it take away?
We'll be right back just after this.
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Shiny shoulds do not just relate to social media. We all know the phrase stop shoulding all over yourself. I think it's a good one. When I worked within corporate, I became a people manager very early in my career at 24 years old and I quickly realized I don't love this. I feel bad even saying it. To this day I feel like I should enjoy managing people. I found it quite stressful. I really appreciated what Josh Kaufman shared on this podcast. He was in the very first ten episodes or so. He shared that because he's sensitive and introverted, he felt like he cared so much about his team and how things were going that it was hard for him to grow a big team. And so he purposefully emphasizes building smarter systems and scales back. And just Josh telling me that has given me so much permission to admit where my energy comes from and what my strengths are and what they aren't. When I worked in corporate, I felt like you should want to be a people manager. You should enjoy it. I felt that if I didn't enjoy it it was because I had a development area that I clearly needed to get better at. I just simply wasn't skilled enough. I didn't have enough courage to have the hard convers conversations. And this is all still probably true to this day. But it was something that went so against my natural interests and abilities that it's one of those things where do you double down on, try to improve your weaknesses or do you just at some point say, okay, I know myself and I know what's going to help me thrive. The stress and added responsibility of being a people manager within a big company honestly was too much for me. I reached a point where I was in so many strategy meetings and just management mishigahs that I was thinking of quitting because I was able to pivot internally. That's when I did join the career development team. The newly formed didn't exist when I joined the company and that's when I did create this global drop in coaching program that I'm so proud of to this day as an individual contributor. The one time I was featured in the New York Times was for this career advice column and I was so happy to see the headline. The headline of the column was Climbing down the Corporate Ladder and I just thought to myself, yes, if there is something that I could be known for in this publication that I've been reading for two decades now at Faithfully every morning, it would be this. It would be climbing down the corporate ladder. Adjusting, shifting, not feeling like you have to keep climbing, climbing, climbing up and to the right, bigger and better. And if you run your own business, always earning more, growing the team, scaling the business. What if you didn't do those things? What if those are shiny shoulds? What could it look like to scale in a different Way, the exercise that I encourage you to try around this is to create a piece of paper. Or you could do this in a digital notebook as well, somewhere where you have access while you're on the go. And be an observer over the next few weeks of your overall activities, projects, meetings on your calendar. What do you find most draining, what's neutral, and what is most energizing? You could also do this within how you serve your clients. And I've done this exercise with friends, clients, masterminds, peers. What are your shiny shoulds, what are your coulds, and what are your so goods? Now, the names are a little funny because I'm trying to rhyme. Shiny shoulds are things you're currently doing for clients that you feel like you should do, but that don't actually bring you joy. They drain your energy. So those could go in the draining column, could do are what you could do for your clients. Maybe if the price was right, if the structure was right, if the conditions were just so. But it's still a could. It's not an enthusiastic so good. That third column is, what is the work that you do with your clients or within the packages that you sell that is so good that you love, that completely energizes you and fills you up? I firmly believe that we all benefit when we operate out of that third zone, that zone of genius, as Gay Hendricks calls it. If you've read the Big Leap, you know that he describes a zone of incompetence, a zone of competence, a zone of excellence, which is kind of a danger zone because that's where we find ceilings for ourselves and kind of a little bit of mediocrity creeping in. But the zone of genius is where you are uniquely serving your clients, your community, the world where you are operating at your highest and best. Do an audit, do an audit of your calendar, do an audit of your projects. Again, at a high level, it's just, what do you find draining? What do you find neutral? What do you find most energizing? But even within what you find energizing, for example, I've shared in recent episodes about keynote speaking. I love keynote speaking, but even within that part of my business, I could then do the second part of the exercise and look at shiny shoulds, coulds, and so goods. For example, a shiny should as it relates to keynote speaking is, I should go to the networking mixer that the event organizer invites me to the day prior. But that's a shiny should, because I feel a little obligated, I should go. But in my heart of hearts, I know that I and the event and my performance will be much better served by a quiet night in where I go to bed at my grandma bedtime. A could do is I could have breakfast with the organizer or could have lunch on the day of the event. But in actuality so good would be that I do that the day prior so that on the day of I can completely get in my zone, get in my little bubble. So the so good as I shared two episodes ago, so good would be that I attend starting in the morning I get to sit in the room at the back of the room and listen and immerse myself in everything that the organization is discussing before I go on stage. So I feel warmed up, ready to go and I have an extra edge of being able to pull their own language and examples from earlier in the day. So you just heard me do a breakdown of Even within a super energizing macro level activity or revenue stream in the business, how can I still segment into the shiny shoulds, coulds and so goods of that area to refine it even more and therefore perform at an even higher, more strategic, more creative, more energetic level?
You know. You know what I'm going to say. I would love to hear from you. I would love to know what are your shiny shoulds? What shiny shoulds are you going to say no to in the year ahead that even as shiny as they seem, you actually want to stop doing? I would love for you to share with fellow free timers. You can always do that by leaving a voice memo@itsfreetime.com Ask and if you want extra accountability and support and feedback and ideas from fellow heart based business owners who are all working through these big questions together to find what resonates and what really serves us best. I would love for you to join us in the BFF community. You can learn more and enroll@itsfreetime.com BFF use promo code PODCAST for 50% off your first month that's itsfreetime.com BFF promo code PODCAST for 50 percent off your first month. I would love to see you in there. Thank you so much for listening everybody. Have a beautiful rest of your day and you hereby have permission to drop all those shiny shoulds.
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