Twenty years ago, I started Equinox with a vision: to provide businesses with strategic legal counsel that felt accessible, personalized, and impactful. Two decades later, I find myself reflecting on the journey — the triumphs, challenges, and moments in between that shaped not just the company, but also me as a leader.
When I started, I knew I had a lot to learn. What I didn’t realize was how much I would evolve, both personally and professionally, in the process. Along the way, I’ve picked up lessons that have guided me through uncertainty, helped me build a stronger team, and made Equinox the thriving organization it is today.
To celebrate this milestone, I wanted to share 20 of those lessons. These insights reflect what I’ve learned about business, leadership, and life over the years. Some of them came from mentors, peers, and experiences; others were hard-won through trial and error. I hope these resonate with you, whether you’re just starting out or reflecting on your own 20-year journey.
20 Lessons in 20 Years
1. Know Thyself
It’s easy to beat yourself up for not being good enough – but the key is knowing who you are and who you are not – and building your team around that. You’ll be happier and your team will be more successful.
2. No One Teaches Us How to Be CEOs
We often know how to do the work, but not how to pull ourselves out of it and focus on what’s important. It can be hard to work on the strategic, planning all alone. Find the people and tools to help you get out of the weeds and do the important strategic work. For me, this was a peer leadership group – Vistage, Entrepreneurs’ Organization and Women Presidents Organization – and a business coach. Being around others helped me do the big thinking and be held accountable.
3. Leadership Is Not Management
I remember my executive coach asking me if I wanted to lead this team – and I wasn’t sure. Hashing out what is management and what is leadership helped clarify that “yes” leadership is for me. There are lots of people who can support me who excel at managing and growing people.
4. Self-Accountability Is Critical — and I’m Not Good at It
Figure out the support you need to stay accountable — and use it.
“If you can’t hold yourself accountable, you have no business holding others accountable” – unknown.
5. The Journey Is Not a Straight Line
There will be setbacks. Be financially prepared for them. Having a savings account with multiple months of operating capital gave us flexibility during some of the most challenging times and opportunity in some of the best times.
6. Yes, You’ll Have a Lawsuit
I was told that if you’re in business long enough, you’ll eventually be sued. And yes, it happened. And even as a lawyer, it is scary. That’s why risk planning is so important.
7. Be Not Only a Good Boss — Be a Good Employer
Just because my Gen X workplace demanded 60 hour weeks, doesn’t mean my modern workplace must as well. A multi-generational workplace is powerful, and I am grateful to have learned from my Millennial and now Gen Z workers. I had an employee (actually a Gen X’er) tell me many years ago, “I work to live; I do not live to work.” It has stuck with me. That, alongside encouragement from younger generations, has made Equinox a great place to work.
8. Test the Resilience
I moved to Ireland in 2014 for two years. I knew the business operations could function without me. But I learned quickly that the culture could not. I had not built a team with common culture and it nearly collapsed the business. That test of resilience was powerful when I began to rebuild.
9. Stick With It — But Be Grounded
I knew we could build and scale a new and different way to deliver legal services to businesses. But I struggled to communicate that vision to the team — maybe it felt like just another “shiny object.”
But I stuck with it, and eventually, we got there — thanks to:
a. CFO who helped us understand the financial aspects of the business model.
b. Experienced lawyers who could reaffirm my “shiny object” into reality.
c. Data that guided our business decisions.
Many industries have figured this out — why not us? There were plenty of times I could’ve walked away, but I stayed grounded in what I knew was possible.
10. Surround Yourself With Your Tribe
A tribe is people who “get” you, inspire you, and build you up. My business is stronger, and I am a better leader because of these connections. My business is stronger and I am a better leader because of Entrepreneurs’ Organization and Women Presidents Organization, and dozens of entrepreneur friends and mentors.
11. Mentoring Matters
I wanted the team to learn and grow, and gave them a lot of freedom to run with new projects. I was always available to help them if needed. But in truth, I really wasn’t. I was busy doing 100 other things, and they really couldn’t reach out for help. We lost some great people because I trusted and delegated, but didn’t mentor or train.
12. Hiring Is Tough
Talk about a tough one. “Hire slow, fire fast.” “Always be hiring.” Is it even possible to get it right? We are talking about people – there’s no wrong person or right person. There’s a fit. If possible, use your culture to make these decisions.
13. Core Values Are Internally Focused, Not Externally Focused
When I started, I created core values and put them on the website for our customers to see. I’ve learned that core values are how we behave, how we work, and what makes us unique in the world. They’re not for your customers; they’re for your team. Values anchor your culture.
14. Curiosity Is a Powerful Tool
It can get you through tough conversations and open doors.
“Curiosity is the kryptonite of judgment” – unknown
15. Process Is Magical
While I personally struggle with process, it is mission critical for growth. Core processes have empowered our team and accelerated our growth. We lost excellent employees due to a lack of clear roles and structure for doing their jobs.
16. Clear Is Kind
We often want to be “nice” and so we are indirect. This isn’t fair. Being clear is the best way to provide feedback and direction. It also sets expectations and provides a foundation for accountability. We had difficulty making decisions because of a lack of clarity.
17. Doing What You Like to Do vs. Doing What Is Important
Hopefully these are the same, but often we jump into what we like to do which distracts us from what’s important. I needed to build in time to prioritize the important to move the business forward. I love working with clients – but now my most important work is in building the business.
18. Recognize Urgent vs. Important
It’s easy to react to the fires and immediate demands – these make us feel important. In reality, these reactions are a distraction from the important work that makes a huge difference in results. I am good at firefighting – but I can’t get the important things done if I’m firefighting all day.
19. Gosh, I Miss In-Person Meetings With Whiteboards!
My best thinking happens with one or more partners and a whiteboard. I haven’t found a good substitute for this.
20. The Pros and Cons of Routine
I learned during COVID how much I rely on routine for health and productivity – and I see it still. I wake up, get ready, follow my calendar’s commands for 8+ hours – rinse and repeat. I love the routine – but I also miss out on many opportunities for creative and social connections that are not scheduled.
