What If You Leap...And The Net Doesn't Appear?

Bracing for the uncomfortable landing

watercolor image of a woman on the edge of a cliff waiting to dive

“Leap and the net will appear.” My coworker’s voice trailed off as he passed me in the hallway. I turned to respond, but he was already disappearing through a doorway, one hand on the doorknob, the other poised in the air in a goodbye wave.

This was last November, my final trip to the New York office of my employer. I’ve worked remotely since 2017, before COVID made “WFH” a mainstream acronym. I traveled back and forth to Omaha, Nebraska many, many times before trading that role for one that took me to the Big Apple regularly.

I had given my notice in October. Rather than the standard two weeks, I offered to stay through the Thanksgiving holiday. My departure was a surprise, and I didn’t want to leave my boss in a lurch heading into the annual sales meeting in December. Besides, I wasn’t on anyone’s timeline.

I was on a freefall into self-employment.

My coworker’s words of affirmations in the hallway that day shot me back a quarter of a century. My first husband, an aspiring actor, often recited that phrase. I always resented those words, presuming they were his way of shirking responsibility.

Now, as the six words echoed down the small stone hallway, I wondered if they would ring true for me.

I couldn’t drink (or yoga) my way out of this one

My level of bravery has amplifed tenfold in my eight years of sobriety. When I got sober, I acted as if I were making up for four decades of lost time (rough math revealed that my blackouts accounted for nearly three months of my life, so I literally lost days).

Over the next few years, I became sobriety’s version of an adrenaline junkie. It wasn’t fast cars or bungee jumps that thrilled me, but the idea of setting my mind to a goal and achieving it, something that eluded me during a lifetime of black-and-white thinking and self-sabotage.

In 2021, I self-published my sobriety memoir. I hosted my first women’s retreat on our property in 2022, two years past my desired goal thanks to the aforementioned pandemic. Midway through 2023, I started my 200-hour yoga teacher training. I doubt most graduates finish and open a yoga studio, but what did I have to lose? The doors to The Rooted Soul Yoga + Wellness opened in January 2024.

I was as big of a thrill-seeker as any former perfectionist, people pleasing alcoholic could be. Calculated risks. Practicality with a dose of eternal optimism.

Leaving my safe job for entrepreneurship might have seemed like the next logical move in my big, bold life, but 2025 had me spinning. For the first time in sobriety, I didn’t know which end was up.

I would learn that menopause, and late-diagnosed ADHD along with it, had its hooks in deep. At the time, I blamed a declining yoga business and Trump’s tariffs for the constant barrage of stress that I thought I could handle.

The pressure relief valve was a corporate exit I’d been contemplating for nearly a decade

Ten years ago, when I worked for a boss who encouraged me to quit the company we worked because of his own discontent, I vowed to “quit retail and write full time.” Instead, I made a career pivot into sales, working for small companies that brought me contentment for a time.

The corporate exit goal has taken on various iterations: by 2020, by my 50th birthday. Each milestone passed and I’d done little to make it a reality.

The dream always came with a strict savings plan I could never adhere to. My husband and I made huge financial strides when we sold our house at the height of the pandemic, but our life still required two incomes.

I built more passion projects than Taylor Sheridan, but nothing seemed to stick. I rarely filled retreats on our sprawling 20-acre hobby farm, usually breaking even with the ad spend.

I dabbled in public speaking and pitched the occasional essay to online forums. My most consistent writing gig was as a columnist for Tiny Living, but like the name of the publication, circulation was tiny, my prose unpaid.

I’m all in, Universe

When we sold the hobby farm last summer, I knew my time had come. The reason nothing had been more lucrative, I rationalized, was that I hadn’t fully committed to faith in a bigger plan, one that would reward my creative endeavors with limitless abundance.

The bold move, therefore, was to push all my chips across the table and tender my resignation. I’m all in, Universe.

Leaving my job felt freeing. At first. There was little fear because countless Case Kenny posts assured me that no matter how delusional I felt, success was headed my way.

Then came an ice storm that cost me thousands in refunds. A service launch that came and went with no enrollment. Ten and twelve hour days spent at the computer trying to convince my nervous system that I was going to be fine.

But what if I wasn’t? What if I took this leap and the net was never going to materialize?

Nobody talks about the freefall.

Sure, entrepreneurs talk about the early failures. Those stories make for incredible tension on the speaking stage. An inspiring hero’s journey.

What nobody talks about is the gap between the leap and the landing.

I have yet to hear about the actual sleepless nights, the tears, the disappointment, and the second-guessing that permeates the early days.

If I had a dollar for every course that promises a 7-figure income, or assures me I can make $2,300 daily, I’d be as rich as those course creators. Americans have always loved overnight success stories, but they are few and far between, despite social media’s attempts to prove otherwise.

I’m still in the freefall.

Maybe someday, I’ll stand on stage and tell the story of the seventeen people who started a bet that we’d lose our house. And I won’t hold back. I’ll describe in detail the early days, the ones nobody talks about because they are a distant memory once you’ve arrived.

I’m in them. And they aren’t fun. But documenting this journey, warts and all, will remind me that regardless of what comes next, I’m writing.