10 Years, 10 Lessons

In June 2007 I made a bold choice: I voluntarily quit my full time job to venture into the work of self-employment. Let me be clear: my full time job was awesome. I was working for a great company and was involved in some incredibly interesting projects. I had the chance to work alongside some truly amazing co-workers—and I’m lucky enough to still work with many of them as clients today. And, the job came with great pay, great schedule, and great benefits. It was probably the best full time job I could (and still can) imagine.

But, however much I enjoyed working there, running my own business has been, and continues to be, incredible. Exhausting but exhilarating too. I have often been told that self-employment comes with the highest of highs and the lowest of lows (I wish I remember who first told me this or where I first read it). And this last decade has provided ample evidence of just how true that is. (Several of the best moments are happening this year after last year with some of the worst.)

As I reflect back on a decade of self-employment, here are ten of the lessons I’ve learned…

1) Give It A Go

When people ask me if they should start their own business my advice is always the same: it is the best thing you can ever do, but also undoubtedly one of the hardest. There are safety nets built into full time work. If you screw up, most companies offer some kind of warning program. If you really screw up, you can file for unemployment. But if you screw up running your own business, the whole company is on the line—especially in the early days. Despite that, if you are thinking of running your own business, go for it. If you fail, you can move on to something else. And, whether you mean to or not, you will learn something from your experience running a business win or lose. That is knowledge you can take with you on the next adventure.

2) But Don’t Be Stupid

If you are going to start your own business, make sure you have a safety net in place. I’d run my own business part time for four years before I quit and I had a handful of reliable clients I could count on for work. The year before I quit, I also put a priority on building up my savings and watching my cash flow closely. I knew what I would need if things went horribly, horribly wrong.

One piece of advice though, once you have your safety net in place don’t obsess over it. Initially, right after I started working for myself full time, I’d check it every single day. I’m not sure why…maybe I thought aliens would come down and wipe out my savings account? This got to the point where it was distracting so I got to a better place where I know the safety net is there, I check it once a quarter to make sure it is still at the right level and then get back to work. Which brings me to…

3) Clients Come First

Well, sort of. I care deeply about serving my clients and always have. But, I also realize I can’t serve clients non-stop. I’ve tried and at a certain point, clients will get diminishing returns. I’ve found I need to take a break from work in general but also that I need to take a break from client work to focus on other projects. As well, if you only ever serve clients you don’t leave yourself time to find new clients to serve or time to learn new ways you can help clients. Gerald Weinberg refers to this as the oxygen mask in More Secrets to Consulting—put your own mask on before helping clients.

4) Specialize

This one is sort of business 101 with so many people talking about finding your niche. Initially, I resisted. I was going to be a jack of all trades for websites. I could write code, optimize content, analyze data sets, and more. To be sure, this worked okay for a few years but ultimately it got harder and harder to pull off, especially as the web grew increasingly sophisticated and each role became increasingly specialized.

I credit my business partner, Andrea Streff, at Elementive for finally helping me see the reasons to specialize in what we were both really, truly good at: using data and analytics to help companies succeed. At first, I found it hard to leave behind all the other things I can do but the more we’ve specialized, the more we’ve been able to gain even more knowledge about data and analytics, which helps us serve clients even better, which helps drive even more success.

5) Giving Back Is Fun

I’d blogged on and off from the start. But if you read some of my early posts you’ll notice a lot of them suck and are kind of overly promotional. Starting around my 6th year in, I decided to try public speaking. It was so much fun to stand in front of a group and teach them something I knew. Compared to my current presentations, those first presentations I did were awful, but I realized how much fun giving back can be. Now, I focus on blogging, making videos, answering Q&A forums, teaching workshops, and public speaking as a way to share some of the things I’ve learned (oh yeah, and I wrote a book too, hint hint). Sure, this helps us attract new business but that to me is a secondary priority; giving back comes first.

6) Pacing

The world doesn’t move at the pace you’d prefer. I’d prefer it if clients spaced their projects out throughout the year so that I could have equal amounts of projects to work on each month. I’d prefer if clients spaced their emails throughout the week instead of everybody emailing me on the same day and often the same hours of the same day. But that isn’t how life works. You’ll have slow days waiting for people to get back to you on everything and you’ll have days where you can’t keep your head above water. Stop expecting things to work a certain way and learn to love the feast/famine pacing instead.

7) Default To Trust

Most business owners I know are optimistic and tend to expect the best in people. I’m no exception to this largely because in the last decade I haven’t amassed a lot of evidence to make me change my outlook (and I’ve not talked to any business owners who had a horror story so awful that it would make me change the outlook). Most people who give me their word hold to their word. An area where trust comes up a lot is with invoices. In all these years, only one client stiffed me on an invoice. A few have been late (see the part about pacing) but the tardiness wasn’t maliciousness. In most cases, it was simply that the client forgot to pay the invoice because of other things in their life. That said, obviously don’t take abuse. If people make excuses or try to coerce you into delivering more than was agreed upon in scope or routinely aren’t paying their invoice on time, say something and fix the situation. But, generally speaking, I find you are better off erring on the side of trusting people unless you have a good reason not to.

8) Sales Is Your Friend

Like many business owners, I have a love/hate relationship with sales. Ultimately though, running your own company means taking charge of sales or else you will quickly find yourself applying for a full time job working for somebody else. So, find your own approach to sales. I’ve tried a whole lot of different sales programs and worked with a few different coaches. None of the programs or advice was exactly right for me but out of all of it, I’ve found my own way to approach sales in a way that works and delivers the results I need. My advice is to try some different approaches, see what fits or doesn’t, then find a way to make it your own (actually, that is true in many categories beyond just sales).

9) Get To Know Yourself

My greatest success (financially and otherwise) comes when I work as a consultant. I enjoy working one-on-one with a client helping them figure out a problem. A close second is when I work as a teacher sharing what I’ve learned with an individual or group (see point 5). Along the way though I’ve tried to deviate from these areas to work in other ways. For instance, I tried to found a software company (twice!). I do a great job consulting for software so I thought I could be the founder. Nope. Didn’t work. Being the founder of a software company didn’t fit my personality type well at all and success didn’t follow. Instead, what followed was a whole lot of money gone from my savings account and a lot of lessons learned the hard way. But, despite the failure, I don’t regret trying something different. Play with different roles, try different things, and get to know where you work best. For me, that is consulting and teaching.

10) Have Fun

You are going to spend a lot of time working on and at your company. It will fill up a lot of room in your brain. So, find something you enjoy doing. This is different for every single person. For me, fun is finding clients I enjoy spending time with, who need help in the areas I specialize in, and who run companies I want to see grow. Having fun means always learning new things and taking on interesting projects. But remember, too, that what you find fun will always shift and change. So, don’t be afraid to shift and change your company, or your role in it, to the things you have the most fun doing and can be the best at.