We’ve got a big community here at HBS that runs the gamut from first-time business owners to serial entrepreneurs. And while some folks were definitely born with the entrepreneurial gene and have always been their own boss, a lot of us—myself included— have had to make the transition from working for others to working for ourselves. So with this group in mind, here is some advice on navigating the winding but rewarding road to professional independence.
One of the things I found most helpful to keep myself going when I got started—and something that I continue to practice today—is to set small, achievable goals for myself each week. Things like calling a specific client prospect, finishing a piece I’m working on, and getting started on a new project. Writing these goals down and looking at them each day may sound like a small thing, but it helps to ensure that you’ll actually complete them, and crossing them off your to-do list provides the sense of accomplishment and frees up the head space necessary to move on to the next set of goals.
Just because you’re working for yourself doesn’t mean that you don’t have anyone to turn to for advice or encouragement. When I set out on my own I connected with a few old colleagues whom I hadn’t seen in a long time but who had also left the corporate world for entrepreneurial ventures. All of them were more than happy to answer my questions and to provide guidance and mentorship that really helped underscore the fact that I was making the right choice for myself. I even wound up setting up a weekly meeting with one of them where we would compare notes, share ideas and just generally look out for one another.
In addition to reconnecting with these folks who’d decided to follow a similar path to my own, I also made the decision to stay in touch with some of my former colleagues who were still working for big firms. While this may seem a bit counter-intuitive when you’re looking to make a clean break, it actually served two important purposes. First, listening to their tales of doing the same old thing day after day made me feel better about my decision to embrace the unknown. Second, and more importantly, they turned out to be a great source of income. Some of my former employers and coworkers have turned into my best clients and sources for referrals.
The final piece of advice I have to offer isn’t particularly in genius but it will save you a great deal of time and headache: hire a good accountant who has experience working with entrepreneurs. The tax consequences of working for yourself are profound and can help inform nearly every decision you make, from where to open an office to whom to have lunch with today. I had an accountant who was great handling my affairs when I was in the corporate world but had very little experience working with entrepreneurs, so it made sense, and saved me money in the long run, to find additional help. Make sure your accountant has the expertise necessary to handle your changing needs.
I wish all of you currently making this big shift the best of luck, and if any of our readers has additional tips on making the transition to business owner that they’d like to share with the HBS community, we’d love to hear them.