🫥 How are you feeling about the state of your business this week?

🔘 Open this message and scroll down to cast your vote . . .

Hi Free Timers,

Did any of you find yourself oddly optimistic about your business forecast in 2020 despite any short-term losses, only to find that for each subsequent year that you thought ThE eCOnOmy was sure to turn around and things would return to “normal” (lol), they only became rockier?

Is it just me? We’re almost halfway through 2025, and I’d like to grab my 2020 self by the shoulders and say: BATTEN DOWN THE HATCHES!

I’m in a small business mastermind, and in 2021, we all poured more money than we’d ever previously dared into our respective companies. That’s how hopeful we were, relying on a lifetime of sunny optimism and a decade of boom-time number-go-up business returns. We figured that by doubling down while the market was down, we would be rewarded; you know, the creative risk-taking that inspired us to launch our own businesses in the first place!

By the time Free Time book launched in early 2022, and as lockdown restrictions continued easing up, I was sure things would turn around any day now. What things? Who knows! THINGS! For me, that’s mostly in the form of speaking engagements; I went from averaging two a month pre-pandemic to a small handful each year since.

Okay fine, I spoke too soon. Surely by 2023. Nope, not for tech companies, my biggest clients, who declared it their year of efficiency and austerity while announcing waves of mass layoffs. (

Melanie Ehrenkranz

’s

Laid Off

Substack is a favorite recent find.)

Hey, at least Pivot is more relevant than ever, and Free Time teaches operational efficiency through smarter systems. I was onto something. No matter, because in summer 2023, my largest licensing client cancelled our contract, representing over $200,000 per year in lost revenue. It was such a shock (even though I braced every Christmas for seven years for that very possibility) that I started writing twice weekly essays about what I was feeling—and suppressing—and I haven’t stopped since.

I knew that 2024, an election year, wouldn’t prove to be any easier. Survive ‘til 25! became the small fish mantra many of us shared.

Okay, but now 2025 is here, and when I tried to order my husband a $200 baby-blue bass guitar from Germany last week as congratulations for hitting a major milestone, UPS slapped a $350 tariff onto the package, due upon receipt—on top of the $100 for international shipping that we already paid the vendor.

Sorry, but we’re not paying $650 for a $200 guitar. Sadly, we turned “Daphne” away at our front door step, sending her back to whence she came, alongside any remaining hopes that the economic turbulence would let up any day now (lololol).

For years, so many people I have spoken with have seemed anxious, and not just the small business owners. Out of care and concern for my financial anxieties as a breadwinner, many of my loved ones ask why I don’t just get a job (ye ol’ refrain), but I’m not sure that’s any easier.

One friend, a product manager in Silicon Valley, was laid off in 2023 and is still looking for full-time work, while stringing together consulting gigs in the interim; the market is so saturated with PMs who are also out of work that he has a hard time gaining traction during the interview process. Another Director-level friend was laid off from a lucrative job at one of the FAANGs, and the entrepreneurs I know are getting more leads this year, but not necessarily more clients.

Former guest of the pod and Pathless Path author

Paul Millerd

shared a fantastic article from

Rosie Spinks

along these lines, “Everyone I know is worried about work,” whether “finding a job, keeping the one they have, or what will happen when the work they do no longer exists.”

The New York Times published a depressing piece about Gen Xers’ career meltdowns, “It’s the end of work as we knew it.” I’m a geriatric Millennial and latch-key kid, so right there on the cusp.

On the other hand, one friend’s Delightfully Tiny company received three six-figure requests for proposals the day after the election, and renewed interest has been bubbling up for them ever since. I have been fortunate to receive a few big leads and clients this year, but trying to plan even a month out still feels like staring into a business abyss.

Or is that just my Millennial midlife crisis talking? You tell me . . .

💬 I’d love to hear from you:

💬 Comments are open, so if you are willing to share more details about your response, we can commiserate—and/or celebrate—together!

🎙 Related Episodes

205: Why Paul Millerd Turned Down a $200K Two-Book Traditional Publishing Deal

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

🍩 Recent at Rolling in D🤦🏻‍♀️h with Jenny Blake

👾 "I'm an alien," part one

🏐 Cast Away Confidence

That’s all for now—thank you for being here, and if you’re in a similar boat, hang in there!

❤️ With Gratitude,