I've been an independent contractor a few times in my life now, and I've loved it each time I've done it. I've had to learn a lot of lessons – some of them easy and some through the school of hard knocks. I wouldn't trade any of them for an easier path.
The first time I was an independent contractor was around 1998 when the company that I was working for, Datalytics, was purchased for pennies on the dollar by another local company, MTC. I knew enough about MTC that I decided that a career with them was not something I wanted to pursue. One of my managers at Datalytics came up to me after the announcement and asked if I wanted to do some contracting work for another local company, Emerson Electric. They needed work done on their warranty claims site. I was working without a formal contract on a system that didn't have formal requirements. You can see where that is going. I was also not able to do time and materials billing. There were a ton of things that I learned from this experience. The biggest is that you either need a formal contract in place, or a VERY good relationship with your client. I learned a ton about how to communicate and how communication can break down. I learned that formal requirements and change processes are absolutely needed on a fixed bid contract. I also learned, from the school of hard knocks, about client management. I worked on this contract for about nine months and then I was blessed to receive a call from another former manager at Datalytics who had landed at Chase Home Finance for a position there.
For the next decade I mostly working as an architect and sometimes developer at businesses large and small around the Cincinnati area. I worked for big banks, retail ecommerce brands, startups and others.
In 2009, I was working for a startup, Balanced Insight. It was a good position, and I was learning a ton. Balanced Insight had decided to grow through investment, and unfortunately, 2009 was not the right time to be growing through debt. I was laid off at the end of October in 2009 and had just had twin daughters in March. There were a number of interesting lessons learned through this layoff that I wouldn't see until years afterwords. The first, is that I had around five months to spend with my wife and baby daughters. I got to watch them crawl and learn how to walk. I got to practice some of my nascent bushcrafting and survival skills. For that time, I'm very grateful. At the time of the layoff, I actually had the offer to go independent and work for a local insurance company. That offer would come again that next spring, but at the time I thought that I would find something else quickly. That was one of the other lessons. Sometimes you strike while the iron is hot, not when you think that you should. I actually ended up starting a job with the AMIG insurance company east of Cincinnati for about a year, working on the rearchitecture of a significant internal system. That was the beginning of a relationship with a local consulting group, Callibrity. My second layoff as an independent came at the end of that year. I was accused by the client, not Callibrity, of not wanting do the work that was being put before me. That couldn't have been further from the truth. I had asked architecture questions to the manager that I was working for there that called some of the decisions that were being made into question. There was also a lack of work at the time. Either way, I was laid off a week before Christmas. I found a consulting position within a month and a half, but learned some important lessons there too. Most importantly, always have a second client, even if it is just a few hours per week. Never rely on having only one client. Even if the relationship is comfortable with the end client, if you're subcontracting, always have, or notify, your direct client when you might be presenting controversial ideas.
From there I went "back inside" a consulting company and did some Java work, but also got to do some Groovy/Grails work for a client in Kansas. About that time, one of my friends, Jeremy Kahne, had been continuing to talk to me about Ruby on Rails and how he was working for a great small company in Loveland, SCRIP-SAFE, International. When the consulting company was having large financial issues that year, they gave me a month or so of "runway" to go find another job. They were really nice to do that. I interviewed and went to work for SCRIP-SAFE that same year.
Fast forward to 2014, when Credentials Solutions of Chicago bought two of the products from SCRIP-SAFE and aquired all of the employees that went with those products. SCRIP-SAFE had one more product, but no techincal employees to support it. That started my current and longer term indepenent consulting work.
Since that time I've had SCRIP-SAFE as my longest and one of my best clients. I do everything from running servers to wrangling code for them. We have a great relationship and I look forward to many more years with them.
For a year, through Callibrity, I did some long-distance contracting work for IPC, the payment processor for Subway. I leared a lot from this high powered team. I grew a ton, but also learned how relationships, if not fostered and understood correctly, can turn caustic.
Around that time, I was contacted by RoleModel, a consulting company in North Carolina. I worked for them for the better part of a year. That was also a high-octane time. I learned a ton about how to run a business transparently, more sales knowledge, and a ton of Rails knowledge. It was late in 2016, when I was putting in a lot of hours at RoleModel and then occasional other hours with two other clients, that I hit burnout and had to make some hard decisions. While I loved working with the people at RoleModel and liked working for McKesson, one of their clients, I knew that the stress that I was feeling at McKesson was one of the reasons for the burnout. To RoleModel's and McKesson's significant credit, they did everything that they could do to retain me.
For the last year, I've had a wonderful relationship with three long-term clients, and I've worked the least amount that I have in years. That's not saying that I'm not putting in a full week. I'm looking forward to that time in the future. I'm working generally about 40 hours a week now and I was doing 50-80. My health is slowly improving. There are more things that I can change and do to improve. Overall, though I'm on the right track.
I can say that while I wish I had learned some lessons earlier in my life, I would not change a thing. I'm really blessed where I am and am looking forward to the future. Being an independent contractor and having a growing business is one of the most rewarding things that I've done.