5 things I no longer chase after 19 years as an entrepreneur
On May 9th, I celebrated 19 years of being an entrepreneur. 19 years! Can you believe it?!
Over those 19 years, I went from cleaning houses between college classes to starting a business and falling in love with leadership, which helped me uncover my true passion: speaking and leadership development. I never imagined that putting an ad on Craigslist to clean one house would lead to me igniting human leadership in workplaces all over the world.
I always take a moment around this time of year to reflect on my journey and all it’s taught me. This year, I’ve been thinking about how much my perspective has changed since those early days and how I’ve let go of or stopped doing things I used to think were so important.
One of those things is chasing. When I first started my business, I chased anything and everything I thought might give me and my business a better chance at success: opportunities, growth, relationships, approval, etc. I clung to the mindset that I could control and achieve anything if I just worked hard enough. I lived for the hustle.
But nearly two decades in, I’ve learned that hustling isn’t the only way to success—and in fact, if you’re not careful, hustling too hard can hinder you. Now that those days are in the rearview, I thought I could walk you through some of the things I’ve stopped running after in favor of living a bigger, brighter, more peaceful life.
After 19 years as an entrepreneur, here are five things I’ve stopped chasing:
1. Making something fit that doesn't
I used to believe that if something almost worked, it was worth it to find a way to make it work. Whether it was an opportunity for growth or a new client, I would tell myself that if I could just be more flexible, get more creative, put in more effort, reduce my pricing, etc., I could make it happen.
In the early days, that mentality made sense: I took on every new opportunity I could so that I could learn what was a great fit for me—and also so I could make payroll. I didn’t always have the option of turning down business, even when I didn’t think it was the right fit.
What I learned over time, though, was that the opportunities, the client relationships, and the growth I had to force were the most challenging and draining in the end. Because they weren’t in alignment with my strengths or what I truly wanted, I had to use up even more energy to try to make them work.
I know now that if something is a good fit, there’s little friction. That doesn't mean that there aren't barriers to overcome or problems to solve, but when things are in alignment, there’s an underlying sense of ease throughout the process.
I really believe that if something is right—the right client, the right opportunity, the right direction, etc.—you can feel it, and I’ve learned to surrender to that feeling. At first, it was really scary: One of my mental blocks was a fear of missing out. I thought that if I turned down an opportunity, we would miss out on the revenue that came with it, and then, I’d worry that we would never make it up. But by saying yes to everything, I ended up with a calendar so packed that when the opportunities that were completely in alignment came along, I didn't always have the capacity to take them on. So now, that’s why I only say yes to the things that feel 100% aligned.
2. Convincing people to stay
I used to view someone wanting to leave my company as a personal failure. I thought it meant I was a terrible leader and that my company and its culture were terrible, too. When someone told me they wanted to leave, I would go to great lengths to try to convince them to stay. Sometimes, it worked, and people would stay far longer than they’d planned. But in the end, they’d usually leave anyway after some time.
It wasn’t until I was ready for an evolution of my own that I learned how important it is to have the freedom to change your path. When I decided I was ready to move on from Student Maid and become a speaker full-time, I learned what it felt like to want something different for myself. Now, I don’t take it personally. I make sure that everyone in my company has the freedom to evolve, even if that evolution takes them somewhere else. It’s not fair to convince someone to stay when something is pulling them elsewhere; instead, it’s better to support them.
True leadership isn’t holding people hostage. It’s empowering them to get their wings and then standing back so they can fly wherever they want to go.
3. Growth for the sake of growth
There was a time when my company couldn't be big enough. I wanted us to keep growing, keep bringing in revenue, keep reaching new heights. I had no clear reason or goal; I just wanted more, more, more—and living that way led me straight to burnout.
I’ve since realized that growth needs to come with intention. Instead of saying yes for the sake of it, I say yes when it aligns with my goals and the direction I want to grow. I ask myself if the opportunity in front of me gets me closer to my end goal or farther away from it.
A big theme in the most recent years of my entrepreneurial journey is the value that I’ve placed on my life outside of work. It’s no longer worth it to me to chase growth at the expense of my relationships and how present I’m able to be when I’m not working. I still hustle and I still have tremendous ambition, but I’ve learned to put limits on it: Instead of hustling 24/7, I have seasons of hustle. I’m more intentional about what I go after, and I make sure that I am taking care of myself in the process. Figuring out how to grow while not losing myself in the process has led to some of my best work and has attracted my best clients and opportunities.
4. Control
When I started my business, it really did feel like my baby. It felt like an extension and a reflection of me. So from the very earliest days, I wanted to be involved in every part of my business. Deeply involved. Like, if Student Maid got a Google review that wasn't great, I would take it so personally that it would make me want to double-check everyone's work. It came from a place of caring about my company, but I can see now that if that's how you lead or run your business, the business can only go so far. I started to realize that if I was involved in everything, my team could only grow so much.
Over time, I’ve learned to step back so that other people can step up. But I can’t deny that this is still a challenge for me at times, especially because my business today is literally my name. The way I’ve learned to manage it is by asking myself how much I care about something on a scale of 1 to 10. If it’s an 8, 9, or 10, I allow myself to be more involved. But anything less than that, and I tell myself to let go. That doesn't mean that I always like the outcome, but I can live with it, and if it goes wrong, I know we’ll learn and grow from it. Often, though, I’m pleasantly surprised by how things turn out. Sometimes, they end up way better than I would have ever thought.
I think that part of letting go of control is recognizing that people aren’t going to do it like me, and that can be a great thing. It’s so worth it to give up that control because not only am I helping my team grow, but our company goes farther, too.
5. External validation
I used to really care about what other people thought of me. When I started speaking, I’d pay close attention to how my message was received and whether people liked it (and me), and that’s how I would measure my success.
But a Q&A session I led after one of my speeches changed that way of thinking. One gentleman in the audience told me that he didn't agree with what I’d shared. He pushed back and challenged me, and though I held my ground, I left thinking I’d failed and done a terrible job.
My dad happened to be in the audience that day, and I’ll never forget what he told me when I shared how the interaction made me feel: He said, “You know, if everyone agrees with you, you haven't made it clear what you stand for.” He helped me see that because I had said something that made this gentleman disagree with me, I had made it clear what I stood for.
That totally changed the way I saw the situation, and it helped me realize that I don't want universal approval. I want to live by my values and what I believe in, and that might mean there will be people who don't agree. As long as I am living in integrity with myself and being the caring and courageous leader I want to be, I’m doing it right. I now measure my success by meeting my own standards, and that's what brings me peace when I put my head on my pillow at night.
Nineteen years in, I certainly don’t have everything figured out. I'm still learning every day. But now, I know success is not necessarily about chasing more. It's about choosing more intentionally and living a more intentional life as a result. The lessons I’ve learned in my entrepreneurial journey apply everywhere in my life.
So now, I want to ask you: Which of these five resonates most with you? What is something you’ve stopped chasing as you’ve grown in your career and life? Hit “reply” and tell me all about it! My team and I love reading your reflections.
Cheers to 19 years! And many more ahead.
Big hugs,
