How my definition of success has changed over the last 18 years
On May 9 (next Friday!), I will celebrate 18 years of being an entrepreneur.
It’s hard to believe. The years have gone so quickly.
My entrepreneurial anniversary always inspires me to reflect on my journey. One thing that really stands out to me this year is how much my definition of success has evolved since I first started a company—and the parts that have remained the same.
Let’s start with what hasn’t changed.
Since day one, I’ve found tremendous meaning in helping others. I love to help people grow. I love to pour into them and help them uncover what they have inside of them. I love to help them bring it out and surpass limits they thought they couldn’t.
Aside from that, my definition of success has changed in every other way.
When I first started my business as a 19-year-old, there was no limit to how big I wanted it to become. In those early years especially, I was always pushing for more, more, more: a big team and a bigger office to go with it; a Student Maid branch in every single college town in the country; double the revenue than the year before . . . I was a walking billboard for the phrase, “Go big or go home.”
Thinking back on those days, I thought the startup life was absolutely thrilling. I loved the challenge and excitement of having so many different balls in the air and the twists and turns that meant we were constantly innovating and problem-solving. I loved emergencies and having to figure out how to resolve them. I loved working into the wee hours of the night and on the weekends. I turned down party invites and trips with my friends so I could keep working on the business because that’s truly how I wanted to spend my time.
In those early years, I was thriving. My growth goals got me out of bed better than my alarm clock did. I never once considered that my goals or my working style would change. I never once considered that one day, I might want something different.
But over time, I noticed a shift in myself: The growth started to feel stressful. I began to daydream about having a smaller operation. I began to imagine what a business that was calmer and more manageable might feel like.
That was an inflection point for me. The startup life I had once reveled in was now more draining than exciting, and leading a large company became synonymous with being stressed out 24/7. When my phone rang, it was always a crisis, and one that I didn’t want to have to solve. I got to a place where I didn’t want to turn down the trips with friends, and I didn’t want to work on the weekends. I wanted to make memories with my loved ones and find new hobbies. All of a sudden, there was more to life that excited me than working on and owning a business.
As I was going through this evolution, I could feel it. I knew that the way I defined success was changing, but fear kept me from allowing myself to evolve to align with that new definition.
Looking back, I think I was so afraid of being judged. We don’t often hear about CEOs who want smaller companies or who choose to downsize, not because they’re forced to, but because they want to. It's only the CEOs who are responsible for explosive growth that we see in the news and who we've learned to call successful.
In many ways, I felt like something was wrong with me for wanting a smaller, more focused, and more calm business. But at the end of the day, I couldn’t deny that it’s what I wanted.
If you’ve ever been in a place where you are living out of alignment, you know what I was going through. It becomes all you can think about—that you aren’t being true to yourself. I eventually got to a point where the pain of living inauthentically was too much to bear. I had to make a change: I didn’t want to get to the end of my life and have regrets, and I knew I certainly would if I continued living life the way that I was.
On May 9th, 2021, I did one of the hardest things I've ever done. My leadership team—who supported me every step of the way—and I stepped into a new chapter. We transitioned beyond Student Maid and partnered with two of our competitors to make sure our clients were taken care of, helped our team members find their next steps, and went all-in on the things that I am most passionate about: leadership development, teaching, and speaking.
We went from a team of hundreds during our busiest seasons to a team of four, including me. We went from a physical office to not having one at all. We went from a 24/7 business to one that closes for six weeks a year and has a four-day workweek. We went from constant emergency calls to having hardly any.
It was an incredibly hard decision to make, and I don’t want to discount that. But it’s also a decision I look back on with a lot of pride because it was the first time I had the courage to admit out loud that my definition of success had changed. I had finally given myself permission to align my life with what I truly wanted.
Today, I define success a lot differently.
First, I want my work and my life to work together. I want to have a life that work is a part of—not a life where it’s the whole thing. I love my work. It lights me up and gives me incredible purpose and meaning. But I don’t ever want to resent it because it’s in conflict with other things in my life that are important to me.
And second, to me, success is also about being authentic and following my heart. I want to continue to have the courage to do the things that I'm passionate and excited about and not always have to have a business-case for doing them. I want to feel like I am always staying true to myself.
There's a concept I think about now that really helps me. It helps me give language to feelings that I’ve had a hard time articulating in the past. It comes from Kim Scott, the author of Radical Candor. In the book, Kim talks about two types of people—superstars and rock stars—and how growth means something very different to each of them.
A rock star is a specialist. This is someone who wants to find their thing, learn everything they can learn about it, become an expert in it, and do it every day. Growth to a rock star is going deeper into their area of specialty.
A superstar, on the other hand, likes variety. They crave upward, fast growth. Superstars thrive on taking on more responsibility, and they are excited about the idea of moving up. They don’t want to be working in one area for a long time.
One isn’t better than the other; we need both. And at different points in your life, you may feel more drawn to embodying one or the other. It’s really common to evolve between the two—that’s what happened to me: When I started my company, I was a total superstar. But now, I’m in my rock star era.
The thing is that our world is programmed for superstars. Especially here in the U.S., we’re constantly encouraged to go for more. Bigger is better—and that goes for titles, salaries, responsibilities . . . the things superstars are excited to work toward. That’s why I felt a lot of shame about being a CEO who wanted less.
Superstars are amazing. And there are also a lot of rock stars who want to rock the thing they are good at and keep their focus there—rock stars are amazing, too.
Whether you are a superstar or a rock star, I hope you have the courage to own it. I also hope you have the courage to own a new definition of success, should yours change like mine did.
What do you think? At this point in your life, are you a rock star or a superstar? Do you want more out of life or less? How has the way you define success evolved over the years? Hit reply and tell me more. I’d love to learn about your own reflections on this topic.
I can’t end this post without saying thank you.
Thank you to you.
Whether you’re brand-new here or you’ve been with me through it all, I’m so grateful that you are walking alongside me on this journey.
If you’ve been a longtime member of our community, thank you for being with me in all of these different phases over the last 18 years. Anytime I announced a change, especially the big transition in 2021, the support from you is what encouraged me to keep following my authenticity and to have the courage to keep doing that. It would be a lot harder to own my definition of success without your support, so thank you.
May we all have the courage to remain authentic and to define success for ourselves!
Here’s to the next 18 years.
Big hugs,
