262: 🪜Climbing Down the Entrepreneurial Ladder — Rolling in D🤦🏻‍♀️h

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We don't need new Phoria, we need old. For you the joy in what already exists. We need simple for you the joy in streamlining. We need enough. For you the celebration that what we have and who we are is already enough.

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 you can 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.

Welcome back Free Timers. I've got another Rolling In Dough crossover for you today. This is one of the most popular posts in recent weeks from my substack Rolling in Divine Disaster Diaries from a breadwinning business owner living in New York City. I've had this rolling for seven months now, if you can believe it, after I got the news that my contract would be ending with my favorite former client. Rolling in doe is my project to document what happens after that. What happens when you lose your biggest client? I've been posting twice a week, pretty much without fail, for these last seven months. So if you're not already subscribed, I encourage you to check out any of my three substacks, do pivot and free time by visiting my profile@substack.com ennyblake without further ado, I bring you climbing down the entrepreneurial ladder, sidestepping status games to find the bliss in simplicity.

From one of my favorite humorous writer substacks, Shalom Oslander's fetal position. He writes, things today are way better than things capital T have ever been. Cavemen had sticks in the Middle Ages. They had typhoid. We have iPhones and Herman Miller chairs and shoes with air in the soles inside the souls. How do they get the air inside the soles? We are living in the golden age of things. In the golden empire of things. This is from his post Beckett Drove a Deux Chavau. I don't even know if I'm saying that right, but I'll put the link in the show notes. That article is hilarious. I first encountered the Apple billboard a few days after Christmas. I was walking down 14th street in the Meatpacking District and there it was. New for ya. Hallelujah. New jargon for the rampant consumerism of the holidays and beyond. New and shiny plus fleeting hedonic treadmill euphoria equals New Phoria. Side note, I probably was so triggered by this billboard because I find the holidays stressful as is and I feel so much pressure at Christmas time, especially not just to spend a lot of money on plane tickets to go see family, but the gifting I just feel like spending on material things becomes so stressful and out of control. And so here was this big Apple billboard blinking at me saying New Phoria. Alas, I digress back to the post. Fifteen blazes like a beacon for the Apple Store below, luring and ensuring that passersby upgrade to the latest greatest device. The ad features an intimate face down photo of the newest iPhones. Somebody tell me why this is so special. Camera. The lenses look like oversized eyeballs or lily pads leading to the promised land of newforia. Now this billboard almost sent me on a signage rant. I did a rant in a previous post. I'll put that in the show notes right then and there. But instead I quietly snapped a photo with my lowly iPhone 13 Pro Max and tucked it into my digital pocket so I could remember to vent at a future date. Maybe it's just a holiday promo to incite phone fomo, I thought at the time. But there it was again this week, still standing, taunting me, begging me to respond. Don't mind if I do. You know what? We don't need Apple. We don't need New Phoria. We need old Joy in what already exists. We need Simplephoria, the joy in streamlining. We need enough for you, the celebration that what we have and who we are is already enough. Newphoria so often becomes a mirage. Greener grass always just out of reach. New Phoria is the shine of the long tail. The tiny tip that we see, hear and read about atop the peak of success. While most of us content creators exist and subsist in the very long tails trough Newphoria, at least as it relates to running a small business is not always all it's cracked up to be. I was fortunate to get featured in the New York Times one magical time throughout the last decade plus of trying to land coverage for three books and I couldn't be happier at the headline Climbing down the Corporate Ladder. This tickled me. It still does. I was so happy to wave the flag for moving back down, just as I had while working at Google People Management was not for me.

We'll be right back just after this.

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Burlington encuentras precios increibles y regal los geniales Jesus energia del protagonista porque in Burlington los ahoros festivos no son lo unico que llama al attencion descubria jasgos de calidar y regalos perfectos paratodos and tulista des de jugetes hijollas hasta nuevas marcas de belles.

Para de bajo del armol in serios para.

After my promotion to Team Lead early in my career and my time there, a junior role bogged down by pushing pixels across PowerPoint strategy decks, slogging through performance review write ups and attending never ending back to back meetings, I looked up the rungs at my possible future in middle management and said, not for me. So I moved back down cross if we're being generous and into an individual contributor role. Less than a year later, as I further explored this idea that not all of us aspire to some tiny peak atop success mountain, I premised one of my earliest keynote speeches circa 2011-2013 pre pivot on treating your career like a smartphone, not a ladder. I encouraged people to download apps, skills, projects and experiences that make their phone rewarding functionality and unique. After all, no two screens are alike. We don't compete for who has better apps, just who has the best apps for you. Of course, every now and then there are bugs to work out through bigger operating system upgrades too. The entrepreneurial world has its own ladders of status and success. In his article on the ladders of wealth creation, Nathan Barry, the founder of ConvertKit, writes, There's a reliable progression that anyone can take to earn more and build wealth. In fact, I like to think of it as a series of ladders side by side. Each one can climb to different heights in both the quality of business and potential earnings. To illustrate this idea, he includes a graphic that has a very short ladder on the far left. Time for money. The second ladder is a little bit bigger, three rungs instead of two, called your own service business. The third ladder has four rungs now about productized services and then the fourth ladder is the highest of all and it's about selling products. And that includes things like marketplaces and social networks, SaaS, software as a service, subscription software, physical products, and e commerce products sold into an existing system. In theory, this tallest ladder has the most opportunity for scale and wealth building. But what few people seem eager to talk about what if you're terrible at operating at those higher rungs like I am? What if you're merely competent at managing teams but it drains your life force? What if you get altitude sickness when dealing with this level of complexity As I approach my 13th year of self employment, I can look back and say that my most miserable months coincided precisely with when I ran the biggest team, one that was still tiny by most outside standards. I thought it was what I was supposed to do have a growing coterie of consultants on retainer, an attorney, a sales agent who sold nothing, a program manager for corporate licensing and speaking clients, two entry level admins, a community manager for my membership program, and a podcast production team, as my friend Charlie Gilkey calls it in a free time episode. The social overhead of managing that many people made me increasingly miserable. I couldn't hear myself think no matter how many systems I devised or how much I delegated. So shortly after FreeTime launched, I let everybody go, leaving just me and the podcast production team for the summer of 2022. I was instantly happier. I had peace again in my heart, my inboxes and my slack channels. Today I work with a wonderful part time VA and I'll even be pausing the podcast soon. Simple, Creative, Tiny for you. One of my favorite explorations of this topic comes from my friend Jonathan Fields from his blog Archives. In a classic piece called the Unfortunate Middle, he writes, with a rare exception, the middle is not the easier, most comfortable place to be, but rather the hardest to sustain and the least rewarding on nearly every level. Sure, it protects you from the anxiety of growth and the stress of survival, but it also ends up feeling like the worst of both worlds. I am obsessed with stories of people who purposefully downsize their small business, a category the US government defines as fewer than 500 employees, mind blowing to even smaller, particularly after experiencing success at, quote, higher levels. It reminds me of one of my favorite childhood board games, Chutes and ladders billed as an exciting up and down game for little children. If only these swerves are so exciting as adults when it often feels like our very survival needs are at stake, maybe they can make one for creatives and small business owners get featured on Substack Climb the ladder two rows. Failure to delegate. Down you go. Land a wheel of a client. Hike up seven levels. Lose that client to economic contraction. Curl into a fetal position at square one. Double down on the creative arts. Build the ladder your damn self. I appreciated Catherine Ross's financial transparency in her recent post on closing the second location of her Fern Scene business in Tacoma, Washington. She writes, most importantly, I have hope again. For the first time in a long time, I feel like I'm running a manageable operation, something that fits my life, not constantly chasing the dream of growth that exceeds my capacity. Stay small, friends. Trust me on this one. As I reflected on climbing back down my own entrepreneurial ladder past a construction site just a bit further down 14th Street, I laughed when I saw it and an actual ladder lying flat on the ground. Ha. I thought to myself. What if it's that easy? What if instead of a vertical climb, you just lay that ladder down and stroll right across? Or even skip through hopscotch style? I looked up and chuckled again. The back of that same Apple ad was still in view. Serendipity signage flipped and reversed. Here's to soulforia.

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