Oops, it’s my 10-year anniversary

Fly like an eagle, let my spirit carry me

Ten Years in Business—And Still Here

This topic was previously covered in one of my weekly newsletters. To get other timely tips, make sure you’re on the list: www.thejilljames.com/newsletter 

This week, I’m thinking about the immortal words of that eminent philosopher, Ferris Bueller: 

“Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.”

With the end of school and the political drama playing out in Los Angeles this week, I almost cruised right past my tenth business anniversary. 

My business started over lunch. After a failed negotiation of maternity leave from my job, I waddled my 7-months-pregnant self into Tavern in Brentwood. I walked out with a commitment from my first client. Shoutout to Amber Allen of Double A Labs for being a trailblazer. 

While the pandemic ate my five-year plan, I’m not missing out this time. About 35% of businesses make it to the 10-year mark, and less than 15% of women-owned businesses make it to my level of revenue. As one of my mentors said, you’re successful if you’re still here.

The Milestone That Matters Most

But that’s not the thing that I’m most proud of. I’ve noted before that I was both an excellent and terrible employee. Because I got laid off so much, my income history looks like I was interval training. 

Since I started my company, I’ve never not paid myself.

Ten years of never missing a payroll. Closest call was in the second year, when I got distracted by someone else’s vision of a content business and a full-time job offer with a fancy title. I solved for that lull in my pipeline by selling my car and getting deadly serious about monthly pipeline tracking. That’s about the time I started this newsletter.  

What It’s Really Been Like

Ten years of making it work around being a caregiver. Working from hundreds of locations around the world, from my parents’ basement to Paris’ Left Bank. I went fully remote in 2017, long before the pandemic, after stressing over yet another late daycare pick-up in the molasses swamp of traffic between Santa Monica and downtown LA. And I found my centering principle: we always show up for our people.

Ten years later, I’ve worked with thousands of small business owners, from those laying the groundwork to leaving corporate to securing multi-million dollar exits. The highs, lows, pivots, tears, celebrations. And all the days we hauled ourselves out of bed, showed up, and kept things going. 

Does this business look like what I expected on the first day? Not a bit. Do I want my life to be any other way? Burned those boats a long time ago.

Whether it’s your first day or you’ve been an entrepreneur forever, take a moment today to celebrate that you’re here and you’re doing your thing. What’s your next milestone, and how will you celebrate it?

Your Milestone Matters Too

Thank you for doing all the things that keep me going: opening this email every week and giving your encouragement, feedback, comments, sharing, and likes.  Thank you to my advisors and partners for listening, advice, and valuable time. And thanks to my clients for trusting and paying me.

Thank you to my kiddo for asking me what my job is and saying, “Mom, yikes, that is WAY too hard.” Every time I start to drift back toward overprioritizing work, or doing it more conventionally, you remind me why I designed it around life with you. 

If you’re curious about how I got from Day 1 to the present, I talked to Erin Austin about it this week on her podcast, Scaling Expertise. Check out Episode 113 on YouTube, the Think Beyond IP website, or the podcatcher of your choice.

Recent Posts

Not sure where to start? Click here to book a free strategy session with Jill.

More From Jill James