A couple weeks ago I realized that March 12, 2024, is an important professional milestone: half my life owning this business. I had to stop for a minute and think about how that happened. This post isn’t about lessons learned – I did that first on the 25th anniversary and last year on the 30th. Instead, what I’m serving up is a slightly rambly reflection of where I’ve been and how I got here. Thanks in advance for reading.

31 years ago today I left my state job and started my own business. Not for nothin’, but 31 years is half my life.

I honestly didn’t think it would last very long and I was looking for full-time gigs most of the first year. But I did get some business cards and letterhead just in case.* I got and stayed busy enough o stick with it. Even so, I did not have 3 decades of business ownership on my Bingo card.

After all, the odds are against any of us accomplishing that. Data from the U.S. Bureau of Labor Statistics (BLS) show that:

  • 20% of new businesses fail in their first two years
  • 45% during the first five
  • 65% during the first decade
  • 25% make it to 15 years or more.

I am, it turns out, a freakin’ unicorn.

How it started...

I so easily could have joined the roadkill ranks – and at times I thought I might. I began this adventure in 1993 when the Internet was really starting to come into its own. Since then, I’ve lived through:

  • The decline or bust of several major sources of revenue, including general assignment business writing for newspapers and magazines, consulting with tech startups, reporting on real estate and development, freelancing for in-flight rags, and marketing budget freezes during the first two quarters of the pandemic.
  • 3 official recessions: the Tech Bust, the Great Recession and the COVID Recession
  • 2 cross-country relos
  • 2 marriages, 2 former business partners and 2 divorces
After relocating The Word Factory to Hollywood in 1998 and becoming a Playboy contributing writer.
(This was my headshot snapped by Justin Colt Beckman)

...How it’s going

As the inimitable Elaine Stritch sang, I’m still here.

How? I'm not 100% sure myself, but I think it has something to do with pivots. Aside from knowing I'd be writing and problem-solving, I never gave much thought to a "vision" for my business or being an entrepreneur. I didn't set out to do most of the things I ended up doing. Gigs arose and I said yes. Trends moved in a certain direction and I built service lines around them.

I didn’t jump at every opportunity, but the ones I did, I did because my gut gave me a hard YES. I trusted that and went for it. And it worked, even when it kind of didn’t.

  • I talked my way into my first book deal from a guy I met in a bar (and he published my second book, too!)
  • I landed a dating and sex advice deal after telling some pals about a string of bad dates, a conversation that led to a decade of content creation for Match.com and Playboy (link is safe for work, I swear).
  • I got into radio first doing voice-overs and then co-hosting a talk show, when two acquaintances called looking for referrals to emergency fill-ins and I volunteered myself.
  • I became a commercial real estate reporter because an editor said, “can you cover this” and I said yes even though I didn’t know ‘net absorption’ from ‘triple net’. (I learned and was on that beat for 13 years in one of the largest CRE markets in the country!)
  • I grew from a one-person shop to an eight-member collective when a client asked if I knew any freelancers and I said, "Yes, and why don't you let me manage them"?
  • And during COVID when that park ranger suggested I bring my marketing and advocacy skills to environmental education and climate communication, I didn't think twice about following through on it.
A cute picture of writing coach Margot Lester and Be a Better Writer
With my second award-winning book in 2016 (photo by Alex Maness)

When I go with my gut, even the failures are opportunities. And I don’t mean that in a toxic positivity kind of way. I legit learned a lot from each one -- and that contributed to successes down the road.

  • Dissolving my first business partnership taught me a lot about governance, oversight and a good bookkeeper.
  • Scope creep almost broke me physically and financially once. Now I develop clear scopes of work and definitions of done. I even break down the difference between revision and rewrite.
  • Finding out I charged half of what everyone else on the consulting team did (and I got better reviews) was a good lesson in the concept of “left on the table” – and prompted me to go to value pricing and raise my rates.
  • And that time I calculated my business travel incorrectly owed more taxes than I could pay and the IRS slapped a lien on my checking account? I learned the importance of record-keeping and a good CPA real fast.

How did I get here?

There’s definitely some connective tissue supporting my longevity:

Always be closing learning

I’m curious and confident. I like new experiences. Chalk it up to my astrology (Aquarius sun, Scorpio rising and moon) or my extroversion (extreme), but whatever’s at the root of it, it’s been a huge factor in my dodging the slings and arrows of leading an organization through three decades.

Death Birth of a salesman

Selling, pitching and what my Mom called “working a room” are proficiencies I showed very early in life (alongside writing, natch). My parents encouraged these tendencies – especially my Dad, a Madison Avenue ad exec. I like solving problems. I like chasing deals. I know these tasks are difficult for a lot of people and I’m grateful that the baseline traits I need to do this came factory-installed.

I get by with a little lot of help from my friends

Looking back on half my life as a founder, I'm overwhelmed with gratitude for so many people who walked some or all of this way with me. I wouldn't be here if folks weren't willing to pay me, so thanks to anyone who's ever written me a check. But the real VIPs are my kitchen cabinet, the mentors and advocates who took a chance on me, professionals who promoted and referred me, a handful of customers who've brought me along to every job they've had over the years, and my bleacher people – friends who cheered me through all of it. Y'all are the real ones. The magic that breathes life into this unicorn.

The bottom line

If there’s anything to take away from this, I guess it’s that you don’t need a plan or a vision or lots of cash to be a successful business owner. What you need is heart, intuition, luck, curiosity, a squad – and a little stardust.

* Somewhere around here I have my headshot from that first year of sole proprietorship. If I can find it, you bet I'm posting it here.

Hero illustration by Lisa Drake

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