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It’s been 5 years since I became self-employed. I remember at the time, it was right around the holidays in late 2015, I was terrified. The company I’d help found had just been sold and I wasn’t going to transition over to the new owners. I planned to strike out on my own and give the entrepreneurial life a real go. I had a financial runway of about 6 months should everything go to hell immediately but I’d been fortunate enough to build my practice and learn how to run it inside the safety of my former company. I knew the work. I knew how to sell it. And I knew how to deliver it. It was time to try it out without the assured paycheck every 2 weeks.
There was a lot to lose. My kids were 9 and 12 years old and, along with my wife, the four of us lived comfortably in the suburbs of New York City. I felt a ton of pressure to maintain that reality for them. As I started down my entrepreneurial path I realized there was way more to learn than I’d anticipated. I have a tendency to jump out of the airplane and build the parachute on the way down. So I jumped and realized, very quickly, that building that parachute was going to be far more complicated than I expected. I need insurance to run my business? Why do I have to offer workplace compensation for a business of one? How do you run payroll? Did I pick the right kind of corporation type? Where do I find an IP clause for a contract?
These questions might seem obvious, and they do to me now of course, but at the time I was unprepared to answer most of them. The good news was that I wasn’t the first person to do this. I began pinging my friends, acquaintances and other practitioners I respected for answers to these and many other questions. It turns out that many of them struggled to answer them when they started out and, in some instances, were still looking for good answers when I reached out. I wondered if there was a community we could join where we could ask these types of questions and receive honest, practical insight into improving how we ran our respective businesses.
I began to look online. There was Google. It helped but finding answers specific to my needs was tough. There was Quora which was also helpful but the kind of personal endorsement from practitioners whose opinions I valued was missing from there. I tried groups on LinkedIn and pinged my Twitter community as well. All were helpful but none provided the kind of support I needed to learn how to run my specific type of business.
It dawned on me then that perhaps the most effective way to find this kind of supportive community was to build it myself. I’d never done anything like that before but figured it was worth a shot. I launched a Slack group using their free tier service and invited about a dozen folks to join me there. They were coaches, consultants, trainers, facilitators and mentors—all individual contributors working in my or related fields. The group launched with (and maintains to this day) only three rules:
That group is still in existence today. In the nearly 5 years of its life it has taught me an immeasurable amount about how to run my business as well as how to build and maintain community. On a daily basis we ask questions, share experiences, vent, offer collaboration opportunities, coach each other and make each other laugh. We teach each other how we did something that worked or how to avoid something that didn’t work. We help promote each other and we function as a sounding board for new ideas. Inevitably, when life happens, we’re there emotionally for each other as well. And, I’m proud to say, that last year, for the first time in our existence we managed to get about 50% of the group together in person to spend a few days skiing and hanging out together.
A few members of the group posing for a snowy picture last year
Community building and management is incredibly hard work. I had no idea how to do it and I’m not confident I’m much better at it today. What I do know is that, based on the longevity of the membership in the group, the group brings tremendous value to its members. We’ve learned how to curate the conversations in ways that drive a high signal-to-noise ratio. We’ve learned what the approximate right size is for the group and we’ve learned the hard way, how to deal with members that don’t work out.
As with anything, we’re still working out the kinks. Diversity continues to be an issue and one we’ve been actively working on for a few months now. Politics inevitably seeps into the discourse posing questions about what to do when conversations and differing points of view clash. In addition, we’ve been exploring how to democratize management of the group. Since its inception it’s been “my group.” We’re experimenting with models that broaden that responsibility to the community and I’m hopeful that we will begin to implement a new model this year.
I know that my business wouldn’t be where it is today — launching into its 6th year after 5 years of YoY growth — without the support of this little group. I know that the likelihood of me finding a group like this is very small. So I encourage you, as you set out to build your next step or pursue the path you’re on, to seek out folks in your situation and adjacent ones as well. Start the community you want to be a part of. Share the information you have and ask the questions you need answered. Over time and with greater trust, the conversations will grow and bring not just business success but new friendships, collaborations and opportunities you never expected.
I help orgs build better products, executives build the cultures that build better products & you build a better career.
Making the leap to self-employment, or onto any new path, inevitably brings up unfamiliar challenges—and Google can’t always find you the specific and detailed answers you need. So what can you do? When I went all-in on self-employment 5 years ago, questions popped up that I’d never faced before. I need insurance to run my business? Did I pick the right kind of corporation type? Where do I find an IP clause for a contract? When Google, Quora, and everywhere else didn’t offer the precise answers to my questions I needed, I decided to start a Slack group of similar self-employed consultants. Nearly 5 years later, it has proven to be one of the best accelerators for success for all of us. The conversation in the group has grown from practical advice into real-world friendships and collaborations. If you can’t find exactly what you need for your journey, like I couldn’t, I encourage you to start the community you want to be a part of. Read this week’s newsletter to learn how. hashtag#ForeverEmployable hashtag#Community hashtag#ProfessionalDevelopment hashtag#Collaboration hashtag#SelfEmployment
