Deeper Foundations
Build your business - and your business-building intuition with foundational frameworks and practical application.
Dec 17 • 7 min read
Leaving money on the table
This time last year, I was hustling.
I was selling strategy intensives and looking for new clients to start in January as one of my consulting contracts was going to be winding down.
I was rescheduling things in my calendar to take discovery calls, extending my last day of work for intensives, and continuing to publish content.
And honestly? I kept at that pace through most of 2023.
But this November, I caught a nasty chest cold during Thanksgiving.
Apparently, this is what happens when you spend time with kids when ordinarily you spend most of your time working from home. Thanks toddler germs!
I had big aspirations for what I wanted to do in December to bring forward in the New Year.
- I’d drafted a hybrid group/1:1 program focusing on strengthening the different systems in our businesses.
- I’ve been talking about some sort of lightweight content/community offer for months, bringing more networking and resource sharing like a Substack and a WhatsApp thread.
- And when I didn’t have the energy to solidify either of those, I thought about creating a planning workshop in January to help you bring your high-level goals into tangible metrics and projects for the first quarter.
But between delivering for current clients, onboarding new ones, finishing my course filming, and being sick… I didn’t have the energy for anything else.
Even with my current clients, many asked to delay their start dates to the new year or pause their December sessions. I’m really seeing that so many of us need a break right now.
And 2022 Jessica? Would have pushed through.
Would have launched at least one of those ideas. Would have worked a weekend or a long few nights to bring that idea to life.
I would have cleared space on my calendar to reschedule sessions, reached out to prior clients to see if they wanted to do something with the open space and bring in short-term revenue.
I’m thankful that my business, even with some of these timing shifts, is currently resilient enough to weather a transitional month.
But I know I’m leaving money on the table.
More than ever, I’m seeing service-based business owners and creators step back from the pursuit of more money as the highest-order objective.
I’ve seen a number of creators and providers I admire - who have spent years on a build - take a detour from that path this year to embrace their creativity, move beyond a topic area, honor their physical needs, or simply take a break from the relentless pace of the content hamster wheel that’s honestly required to grow an audience.
YouTuber Ali Abdaal has been posting a video twice a week for seven years, amassing almost 5 million subscribers, and writing/publishing a book. And he recently posted an transparent video called “Everything’s Changing.” In this video, he talks about his journey to growth and how he’s ready to take a break from the content schedule that started the flywheel in the first place.
From the video (~26 minutes in)
Am I really going to continue living like, you know, I’ve made more than enough money to sustain my basic needs, I could probably still continue to make reasonable amounts of money if I just make videos when I felt like it and wrote books on my own terms, so why am I chasing more money?
What’s going on there? And that led to a whole soul searching about like scarcity and about self worth and about status and about like, what if all of this comes crumbling down? Do I need even more millions in the bank to like friggin send the kids to school and like make sure my family is healthy and stuff.
And then I was speaking to some speaking to another friend who has also incidentally sold a company for like over 100 million. And he said that he speaks to the community of post exit founders. These are all people who have sold companies for loads of money and now they don’t need to work anymore. And one of his big realizations from speaking to other founders who have been through this is that basically that it’s okay to leave money on the table.
And often if you want to live a life that you genuinely love, that comes at the expense of making more money.
One of my creator inspirations, Khe Hy, has been writing and teaching about productivity for seven years and grew his Rad Reads audience to 50,000. But he retired his course and productivity as his platform this year, though his signature course was making multiple six-figures per year even after cohort-based courses hit their peak in 2022.
I became obsessed with productivity content in my 20s. Being “productive” was an accelerant for my career, finances and owning my time. But productivity falls short on teaching you what it means to lead a “well-lived life.” As we launch our last productivity course EVER, I share the entire course for free as a podcast episode.
You can listen to his explanation here.
And a few of my predecessors in the business training and education space - Tara McMullin, Sarah M. Chappell, Jenny Blake - have all or will be taking a detour from the more scalable group-based businesses they’d built - each with hundreds of members and a seemingly steady revenue. Tara and Sarah have both pursued writing books and paid Substack newsletters, and Jenny launched her own creative writing project and is putting her podcasts on a sabbatical in the new year. (I am a paying subscriber to all of their writings as I follow their journeys and learn from them.)
You can hear about Tara's decision and read about how learning she's autistic changed her relationship to work in 2021.
Sarah and Khe (worlds collide!) have guested on each other’s podcasts, talking about their pivots, what it means to leave a business behind and searching for meaning in a post-achievement world.
I think it’s important to know where they are in their journeys versus mine or yours.
All of these creators and business owners have been doing this for at least 7 years. They’ve built up a reputation, a larger audience, and trust over time - which is a recipe for banking goodwill and relying on "1000 true fans" during a business pivot.
I am not in that place - I’m still building my business and trying to do good work as I grow my presence in the space.
But the question remains… for what purpose am I working? And why would I keep hustling when I am sick?
Would I be working to achieve a 'nice, round' revenue number for the year?
Would I be working to avoid a slower revenue month, even though my expenses are covered?
Would I be working for status?
To potentially “get to a launch” faster than a competitor?
I do want to birth these ideas I have - that deep desire hasn’t changed.
But in this case, I want to reference a card that might be poignant to this time, the 4 of Cups.
In this card, the person is sitting with 3 cups, and the fourth is being offered but not taken.
Quoting my teacher Lindsay Mack:
When we pull Four of Cups, what can often happen is this card often comes up when, not all the time, but it can come up a lot when we’re trying to rush into the next thing. F.O.M.O. can come up with this card, fear of missing out. It can be like, “Oh my gosh, like what if I miss that fourth cup? Like what if I miss it? What if it never comes back?”
…
So Four of Cups is the energy we want to draw forward in helping ourselves to allow an experience to take the time it takes. That is very much a part of intuitive autonomy, reclamation. Things take the time they take. We heal at the rate we heal. We process at the rate that we process. And typically, what winds up happening in this card, what’s actually happening, is that we’re making full space for something new.
…
We’re not pushing anything away. We’re not ignoring that fourth cup. We’re saying, “I respect and acknowledge how, like, the bigness of this, to the point that I’m letting all of these things move through me. I’m moving through a full digestion process, a full clearing process in order to make the kind of space that this project, creation, relationship, endeavor in my life deserves.”
The ideas I have? I’ll bring them to life when it’s time. But I’m in this for the long haul, and that means working at a pace I can sustain, for the right underlying reasons, and making the time and space for ideas to really mature.
So as we wind down for the year… I’d like to offer the idea that, where possible, how can we move forward through a lens of sufficiency.
Acknowledging that driving forward for speed might be counter to our definition of a well-lived life.
That pushing forward an idea for the sake of money or status might actually dilute the power of the creative idea.
I’m not saying don’t take action, and don’t make money moves if that’s what you need to do. Because capitalism be capitalism, and we need to do what we do to keep our bills paid.
But I am advocating that we look at the primary emotion that’s keeping us trapped on an unsustainable pace, and get curious as to if it’s serving our highest self.
With this message, I’m winding down for the holidays. I’ll be back with a new issue on January 7. Thank you for letting me in your inbox this year!
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Build your business - and your business-building intuition with foundational frameworks and practical application.