
Self-employment is a journey unlike any other. It’s a path that offers immense freedom and creativity, yet it also comes with challenges that can test your resilience, adaptability, and sense of self. Over the years, I’ve learned invaluable lessons from being my own boss—lessons that have shaped not only my career but also my personal growth.
You could say I started self-employment when I set up a pen pal company in the summer of 1995. It was the first summer I stayed home alone, and my mom got me a post office box so I could advertise in the pen pal section of the magazine Girlfriends. I even have the same pen pal today, 30 years later, named Sunny, too!
I went on to promote myself and work often as an independent contractor in the theater, both as an actress and on production teams. Later, I built a thriving babysitting business on the Upper West Side of Manhattan starting in 2007. About ten years ago, when I left the entertainment industry, I pursued a Master’s in Leadership with a focus on business, entrepreneurship, and nonprofit management. This education solidified my self-employed career and minimized the unknowns that often come with this path. I wanted to possess the confidence of my maternal grandfather, who ran a deli and fish store as a migrant from Sicily, and my father and his brothers, who were original tour operators in the greater Boston area. My mother gave me the ability to dream, and I wanted the confidence to take those dreams into reality.
Here are some of the key takeaways from my self-employment journey:
1. Your Time Is Your Most Valuable Asset
When you’re self-employed, time becomes your currency. According to a report by the Small Business Administration, effective time management is one of the top predictors of small business success. Unlike traditional jobs with set hours, your schedule is entirely up to you. While this freedom is empowering, it also requires discipline. I’ve learned that structuring my time—with clear work hours, breaks, and boundaries—is essential for productivity, mental health, and engagement with others.
2. Boundaries Are Key to Avoiding Burnout
As I talk and teach about often, there are many benefits to boundaries. In the early days of my self-employment, I said “yes” to everything. Every opportunity felt like it might be the one to propel me forward. And I still believe that when you’re starting out, this is critical if you need to support yourself and build your reputation. Over time, as I became established, I realized that overcommitting led to burnout, not success. Research from the American Psychological Association supports this, emphasizing that setting boundaries is crucial for sustainable productivity and well-being.
3. Flexibility Is a Double-Edged Sword
Self-employment offers unparalleled flexibility, yet that flexibility can quickly become a lack of structure if you’re not careful. I’ve learned the importance of creating systems and routines that work for me, whether that means blocking out specific days for client work or reserving mornings for creative tasks. According to the Harvard Business Review, successful entrepreneurs often attribute their achievements to consistent routines.
4. Networking Is Still Essential
Even though you’re working for yourself, you’re never truly working alone. Building relationships with other professionals, attending events, and maintaining an active network have been crucial to my growth. Collaboration and community support have opened doors I couldn’t have found on my own. On the flip side, I am not required to work with anyone who does not value or respect my work, and I can walk away at any time (or with a 30-day contract notice 😉).
5. Self-Employment Requires Constant Learning
Being your own boss means wearing many hats. One day you’re the marketing department, the next you’re the accountant. I’ve embraced the necessity of lifelong learning, whether through online courses, books, or advice from peers. Staying curious and adaptable has been vital to my success. I’ve also engaged in higher education over the last 14 years, earning a self-designed undergraduate degree in media and journalism, a Master’s in Leadership, and I’m currently completing a Master’s in Psychology. Lifelong learning allows me to evolve alongside my business.
6. Your Health Is Your Wealth
Running your own business can feel all-consuming; however, neglecting your health ultimately hinders your ability to perform. I’ve learned to prioritize exercise, sleep, and mental wellness as integral parts of my workday—not afterthoughts. According to a study published in The Lancet, entrepreneurs who prioritize physical and mental health report higher levels of satisfaction and productivity. I am my own boss, and the boss says staying healthy is a job requirement.
7. Celebrate Small Wins
When you’re self-employed, you are the boss who has to pat yourself on the back or give yourself a promotion—and that isn’t easy when there’s lots of work to be done! I’ve made it a habit to celebrate small wins, whether it’s landing a new client, finishing a project, or simply having a productive day. These moments of recognition keep me motivated.
8. Failures Are Just Stepping Stones
Not every venture or idea will succeed, and that’s okay. Failure is a natural part of growth. Over time, I’ve come to see setbacks as opportunities to learn, pivot, and improve. Each failure has brought me closer to success in ways I couldn’t have anticipated. Every single door that has closed has absolutely made space for something better. It has taken me a lifetime to truly embrace that idea however now I trust it as I’ve seen it happen repeatedly.
9. Know Your Why
Self-employment isn’t easy, and there will be days when you question why you chose this path. For me, having a clear understanding of my “why”—my purpose and motivation—has kept me grounded. It’s what pushes me forward during tough times and keeps me focused on the bigger picture. For me, my “why” is a life on my own terms, time and financial freedom, and contentment knowing I am making the best choices in any moment for myself and my purpose. Being in charge of myself makes that possible.
10. Success Looks Different for Everyone
One of the greatest lessons I’ve learned is that success isn’t one-size-fits-all. For some, it’s about financial freedom; for others, it’s about creativity or flexibility. Defining what success means to me—and not comparing my journey to others’—has been a game-changer. As Forbes notes, entrepreneurs who define success on their terms report greater happiness and fulfillment. Remember, we are each blazing our own trail.
Self-employment is a dynamic, challenging, and deeply rewarding journey. It’s taught me to trust myself, embrace uncertainty, and continuously grow. While the road isn’t always smooth, the freedom to create a life and career on my own terms is worth every bump along the way.
What lessons have you learned from your self-employment journey and what questions do you have? I’d love to hear your thoughts and experiences!
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