Reflection on My EO Presidency
A year of leading, losing, and learning: why I don’t regret the hardest role I’ve ever taken.
I think raising young kids is this crazy dichotomy: exceptionally rewarding, but also so very difficult and frustrating.
And my recent term as president of Entrepreneurs Organization (EO) Sacramento was the same.
Another parallel? I’ll never do either again! LOL
But, after four months of reflection, I decided to memorialize what I learned from the experience. And I’m sure many of you can relate. Many of you have done hard things. Many of you have stepped into roles you were unsure you could succeed in. Many of you have awoken in the middle of the night, imposter syndrome raging, wondering why you ever said yes to “that thing.”
And I’m right there with you.
So here you go: the four lessons I learned from leading a beautiful, challenging, teeth-gritting group of 100+ entrepreneurs:
How Much I Genuinely Love Entrepreneurs
Entrepreneurs are a really odd subset of our society. They’re quirky, complicated, opinionated, and obsessive. They’re also inspiring, kind, thoughtful, and about as fun as any group you’ll be with.
And I love them. I really do.
There is something about them that I connect with. I’ll meet entrepreneurs from, literally, the other side of the world, and within minutes we’re connected and chatting about all sorts of shared pain and success. It’s invigorating. We speak the same language, and really, deep down, have many of the same struggles.
So while I knew, generally, how much I liked my fellow EO-ers before serving them, the love only grew deeper. For most of them. 😉
The Importance of Properly Assessing Capacity
When I accepted this role in October of 2022, things were different. I had not launched my newest business. The economy was booming, and my core business’s economic future looked strong. We had not yet experienced the “Meltdown of 2023” at kitchen & bath CRATE. And another board I was on, while challenging, had not yet driven me to near insanity.
So, in summary, I was future-ignorant.
And if I had really, honestly sat down and “counted the cost,” I may have declined the role.
My takeaway: among my many flaws is an inability to truly factor in future pain. And that gives me boldness, but also puts me in miserable situations. I need to be better at this.
The Delicacy of Navigating Tragedy
My term saw two deaths in the chapter, unrelated and unexpected.
For context, I only knew of one other member passing in the chapter in my prior 7 years of membership.
The news of both of these departures hit the chapter hard. One was a beloved founding member of the chapter, the other an incoming board member loved by everyone who knew him.
I learned a lot about grief and the different ways people process it. I learned the importance of prompt, clear, and compassionate messaging in the wake of tragedy. I learned, quite frankly, a bit more about the delicacy of life.
I also learned how willing many in the group were to rally around the families of those who passed, their fellow chapter members, and even me. The support was palpable. I won’t forget it.
Genuine “Service” Is Hard
I’m not used to doing things that don’t have an upside for me. As I write that, it sounds terrible. But I’m being honest. Even some of the things I’ve done in the past in the name of service have had an ancillary benefit. It helps take the edge off the commitment.
But a role like EO chapter president is not that. There is little upside. If you do your job well, the chapter improves a bit or at least doesn’t regress. And, like a football offensive lineman, success is not being noticed too much.
It makes me think of the hundreds of thousands who do thankless work each and every day. In non-profits, in religious organizations, in our schools, and in our hospitals.
I have newfound respect for those who serve, knowing the upside is nonexistent or negligible, and knowing there is a lot at risk.
Wrap Up
Do I regret serving in this capacity?
I do not. Not now. But I did along the way. And maybe that’s just the nature of hard things. Especially hard things you’re going through in the midst of a lot of other hard things.
But in the end, I learned, I grew, and I deepened relationships.
And who could ever consider those things a “regret?”
Thanks for reading this post. I appreciate you. In return, please share this with those you know who may be interested.
Free Guide: 🧠 Build Your 2026 Business Plan Using AI
I just released my full framework for building a 2026 Playbook: a simple, AI-assisted process to help you plan the year ahead in hours, not days.
If you lead a business or team, this is the exact tool I use every October to clarify goals, align strategy, and make next year’s planning effortless.
Things I've Enjoyed Lately: I’ve tried dozens of software and apps over the years to manage my to-dos. I’ve tried Evernote, Google Tasks, a paper notebook, a remarkable, a Google Sheet, and many more. But for the last 3-4 years, Trello has been my go-to. It’s one of many Kanban-style software tools that let you create “lists” and “cards.” We use Trello for a dozen or so “operating systems” within our business. I also use it for my personal “operating system.” Highly recommend!



