🪜 Climbing Down the Entrepreneurial Ladder

Side-stepping status games to find the bliss in simplicity

“Things today are waaayyyyy better than Things have ever been. Cavemen had sticks. In the Middle ages they had typhoid. We have iPhones and Hermann Miller chairs and shoes with air in the soles. Inside the soles! How do they get the air inside the soles??? We are living in the Golden Age of Things, in the Golden Empire of Things.”
—

Shalom Auslander's Fetal Position

via Beckett Drove a Deux Chevaux

I first encountered the Apple billboard a few days after Christmas. I was walking down Fourteenth Street in the Meatpacking district, and there it was:

Newphoria!

Hallelujah, new jargon for the rampant consumerism of the holidays and beyond! New and shiny + fleeting hedonic treadmill euphoria = neeeewphooooria!

“15” 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 iPhone’s somebody-tell-me-why-this-is-so-special camera. The lenses look like oversized eyeballs, or lily pads leading to the promised land of Newphoria.¹

This billboard almost sent me on a signage rant 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.²

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 newphoria. We need oldphoria, the joy in what already exists. We need simplephoria, the joy in streamlining. We need enoughphoria, the celebration that what we have and who we are is already enough.

Newphoria so often becomes a mirage, greener grass always juuuust out of reach.

Newphoria 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 verrrrrrry looooooooooooong tail’s 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.³ This tickled me! Still does.

I was so happy to wave the flag for moving “back” down, just as I had while working at Google. People management wasn’t for me.

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” (across, if we’re being generous) into an individual contributor role less than a year later.

As I further explored this idea—that not all of us aspire to summit Success Mountain—I premised one of my earliest keynote speeches (circa 2011 - 2013, pre-Pivot) on treating your career like a smart phone, not a ladder.

I encouraged people to download apps (skills, projects, and experiences) that make their phone rewarding, functional, 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.⁴ In his article on The Ladders of Wealth Creation, Nathan Barry, 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 the following graphic:

What so few seem eager to talk about:

• What if you are terrible at operating at those higher rungs, like I am?

• What if you are 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 thirteenth 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 career EA (aka highly paid) 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, 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.⁵

So, shortly after Free Time launched, I let everyone 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 VA, and I’ll be pausing the podcasts soon. Simple, creative tinyphoria.

One of my favorite explorations of this topic comes from my friend

Jonathan Fields

’ blog archives in a classic piece on The Unfortunate Middle:⁶

“With 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 U.S. government defines this as fewer than 500 employees 🤯—to even smaller, particularly after experiencing success at “higher” levels.⁷

It reminds me of one of my favorite childhood board games, Chutes & Ladders, billed as “an exciting up and down game for little children.” If only these swerves were 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 whale 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 yourself!

I appreciated

Katherine Raz

’s financial transparency in her recent post on closing the second location of her Fernseed 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, I passed a construction site just a bit further down Fourteenth Street.

I laughed when I saw it: an actual ladder, lying flat on the ground.

Hah! I thought to myself. What if it’s that easy?!

What if, instead of a vertical climb, you just lay that damn ladder down and stroll 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 soulphoria.

❤️

1. Okay fine, a quick search to the sizzling sales page tells me that:

For iPhone 15 Pro Max, we designed a 5x Telephoto camera with the longest optical zoom of any iPhone ever to fit in our compact Pro camera system. Now you can take sharper close‑ups from farther away.

I highly recommend reading

Shalom Auslander

’s full article on just these types of acquisitive desires—it’s hilarious:

Beckett Drove a Deux Chevaux

2. If you want to geek out further on idea gathering process: here’s a Loom walkthrough of my Collection Bucket in Notion. And a recent Free Time workshop by

Stephanie Huston

with a template for creating and batching content for the year ahead:

BFF 105: How to Create + Customize Your Annual Content Calendar with Stephanie Huston

3. Big thanks to

Rob Walker

for including me in this Workologist column! It’s still a career highlight. He’s now here on Substack at

The Art of Noticing

:

4. I’m not immune from status-chasing—none of us are. In his book, The Status Game, Will Storr categorizes these games into three types: dominance, success, and virtue.

My two all-time favorite books on this topic are Alain de Botton’s Status Anxiety and Wanting by

Luke Burgis

who is on Substack at

Ride or Drive

and

Anti-Mimetic

.

For further exploration on this topic, check out these two conversations with Luke and Khe:

5. See also:

Emily McDowell

’s experience of running a small business that blew up—in a good way—but also led to burnout in her generous, honest posts: The truth about going mega-viral, part one and part two.

The truth about going mega-viral, part one

The truth about going mega-viral, part two

6. Listen to the audio version of

Jonathan Fields

reading “The Unfortunate Middle” here:

7. Here are some of my favorite Free Time conversations with small business owners who downsized their operations:

• 016: IP Licensing and “No Full-Time Employees” with Lee LeFever

• 131: Scaling Joy While Streamlining Business Overhead with Kaneisha Grayson

• 157: Downshifting to a Delightfully Part-Team Team with Laura Roeder

• 173: Cut Your Losses—Even While Pivoting in Public with

  khe hy

• 205: Turning Down a $200K Two-Book Traditional Publishing Deal with

  Paul Millerd

• 241: Finding Freedom and Financial Reciprocity through a Paid Newsletter with

  Nic Antoinette
  — Nic just just launched a monthly column called Tiny Biz Letters, offering transparent updates on her two guiding questions:

  1. What does a right-fit life look like for me right now?

  2. How can I close the gap between what I say I want and what I actually do (without being an asshole to myself along the way)?

Last but not least, you might enjoy these two solo episodes:

138: ⛵️ Stop Sailing the Sea of Shiny Shoulds

210: ⛵️Knot a Care—Sailing the Free Time Seas with Joy and Ease

🎉 🎉 🎉