What I’ve Learned in Five Years as an Entrepreneur

In January of 2011, after 14 years of working for other firms, I opened my own. I was nervous but determined. Five years seems like a worthwhile anniversary to celebrate; a benchmark that in small entrepreneurial business means “you’ve made it.” Here are some lessons I’ve learned in my first five years as a small business owner:

1. The conversations you have today may result in business eight years from now. Lead time can be very long, so keep having those conversations and meeting new people.
2. Don’t waste time with worry. There are better ways to spend time! There was a single day in my second year of business that two large clients ended their engagements. (They were both restructuring.) It was a panic-inducing shock, and I’ll admit, I spent a full 24-hours freaking out about it. And then I stopped, and got busy finding new work. I’ll never kill that kind of time with worry again.
3. Get the signed contract and, especially if there’s some concern about client cash flow, a deposit. I was royally stiffed by a client in the second year of business (it was a bad year, all around. I got divorced, too, and going through that kind of personal trauma while trying to run a business is unbelievably hard). And you know what? I am GLAD now, because that experience taught me such valuable lessons. I also found the courage to fight back and won, a feeling not as gratifying as not making a mistake in the first place, but a relief all the same.
4. Eat breakfast. This is probably a life lesson, in general, but a morning routine that includes getting some protein in my system (and, possibly some caffeine as well) makes it possible for me to rock through a morning without being distracted by something as boring but insistent as hunger.
5. Delegation is critical to success. When I find myself doing something I know another team member could do better, for less, I stop and turn it over. It took me awhile to get to that point but now delegation is much more routine. I can recognize much earlier what MUST be done by me, and what should be assigned to another (eager) team member.
6. Take care of your people. My firm is run as an S-corp of which I am the sole employee. I like it that way and plan to keep it structured like that for the long haul. I have contract employees — freelancers — who do client work such as editing, writing, researching, web development, graphic design, SEO, etc. I do my best to keep them as busy as they want to be, with work they enjoy. I try to pay them as fast as I can. And if it’s a good year, and they did especially well, there’s a little something extra for them. I’ve been able to provide work for people who are good at what they do, and who enjoy the benefits of working a flexible schedule from home (or wherever they are). I’ve worked with a dozen or so contractors over five years and have developed a wonderful, dependable team over that time.
7. Take time off. This was harder to do early on, but I’ve achieved good balance with this and find that a break now and then really resets my energy. I’m not much impressed with people who humblebrag/complain about how busy they are and how many hours they work. I am impressed with people who recognize that time with friends and family, time for self-care, time to think about the big picture and progress toward goals is just as important as earning a paycheck.

I’m so grateful to the clients I’ve worked with since the earliest days of 2011. I’m so appreciative of my team members who have made so much of this business possible. I’m excited about the future and know how rare it is to get to a fifth anniversary (and beyond) through a recession and other obstacles. It’s great to feel confident about the future of this business, and delightful to have you paying attention along the way. Thanks for reading, and for being here to learn along with me.