“I feel like I lost my job.” 27 years old and this was the second time I had ever said those words. The first time was three years earlier, when I launched out to start my freelance web business. Always an adventure.

This may be one of the hardest articles I have ever had to write. I’m not announcing anything profound or revealing some trade secret, nor am I exposing some dark section of my inner psyche. (You get enough of those posts already.) This is an honest look at an honest business, plus the decisions that have brought about the rise and fall of my trade over the last three years.

2010: Venture

Freelancing in Springfield, Missouri was a rough beginning to a lot of rough continuums. Earlier that year, I had been employed by a local web company that didn’t know what to do with a self-starting always-learning entrepreneurial-minded web guy like myself. That job ended when I finished all of the simple HTML/CSS projects they had and they asked me if I wanted to become a full-time ColdFusion developer.

The man who ran that company (wisely) asked me if I really wanted to be a full-time programmer at a desk, or if my self-employment bug was going to win out. I turned down the position, they phased me out, and I became unemployable…the day before I signed my first apartment lease.

That was a terrifying time. There were plenty of things that I had in my bag of tricks, but I had rent due the next day and it was time to make things happen. I took my “Gun For Hire” image as a stoic self-portrait while living in that apartment. My days consisted of listening to books, discovering podcasts, writing code, and trying to understand why nobody wanted to pay me for what I knew how to do.

Perhaps one of the biggest lessons I learned during that first year had to do with educating clients. It’s one thing to provide a solution, but when you have to spend 5-6 hours on Skype with someone as you write their code, it forces you to learn how to explain what you do in a new way. This is one of the most important skills for any knowledge worker, a skillset that is often overlooked; learn how to explain what you do.

Once you can confidently explain what you are doing, or at least communicate what VERB you will be using to reach the desired NOUN, things get a lot easier. You spend less time defending your work and more time showing it off.

2011: Withdrawl

The following year went a little better, but I made a lot of small mistakes that I’m (literally) paying for today. I tried to suspend financial burdens so I could focus on building up a client base, which basically meant that I was throwing expenses on a credit card. I got set up with family services, tried to work the system and arrange payment agreements, and generally wanted to establish myself as a good worker without making money.

Listen: It is never a good idea to lean on someone else for your daily bread while you work on something else. Your work may not bring you into the presence of kings, but deferring things for too long can dig you a deeper hole than you realize. I was (and am) blessed to have parents who helped provide perspective during that season, which ultimately ended with me realizing that I needed to charge something consistent and reasonable for my work.

It sounds silly, but I’m built to be a helper and don’t have a greedy bone in my body. I had to really work to charge a decent rate every time; in some ways I still struggle with this today. 2011 was definitely the year when I poured everything back into the business, hoping enough sparks would start a fire somewhere.

That year ended with my humble recognition that I didn’t know how to run a business on my own. I moved back to Omaha for two months so that I could work with my father. He was going to show me some business tips and help me learn to take things more seriously. I learned a lot while I was up there, and though leaving what I had started in Springfield was tough, I look back and see the wisdom in getting some perspective to breathe and grow.

2012: Investment

In the spring of 2012, I moved back to Missouri to try my hand at the freelance business once more. I had more of a defined business plan, a few small projects under my belt, and lots of ideas for how to pitch website packages to businesses. I knew the business would require a time of “buy in” which would make things tight yet again. Fortunately, I had a new apartment, some new equipment, and a new-found excitement for making stuff happen.

My father had helped me land a big project before leaving Omaha; by far the largest I have ever touched. That helped establish me here in Springfield and provide the stability I needed to re-shape some of my business practices. I wish I could say that the large paychecks gave me the boost I needed to fix the problems from the years prior, but it didn’t work out that way. I certainly did not squander any of the money, but I did mis-appropriate it for current work instead of paying off old debts. Lesson learned.

I think one of the most important things to keep in mind when freelancing is that you don’t truly know what will happen next. Though there is debate among the folks I love to listen to about what “job security” actually means, we can all agree that there is something to be said for a steady paycheck.

I really do believe that having your bookkeeping worked out before you take on a big project is just as important as the project itself. That sounds odd, but you would be amazed at the headaches that can be avoided with a dedication to that principle. Work your fields before you build your house.

2013: Infidel

I know what you’re thinking: “This is the part where he tells us that his business had been acquired by GoogTwitAppleSoft!”

No such luck. The first four months of 2013 saw the worst slump in business since I started back in 2010. Actually, since I never officially went 100% on my own before 2010, I guess I can say that this has been my worst year of business…ever!

This may be too much information, but I want to be honest; I’m running on empty over here. For the past three years, I have fought and struggled to make this small company turn a profit, with varying levels of success. The kicker is that I have been working almost completely on my own. Until late last year, when I began to email other web professionals here in town, Twitter had been the only real place I could go for business chatter. My clients were the only lasting colleagues, and to this day no one in my close spheres of friends/family have any real understanding of what I do.

Want to know a secret? I have not taken a single web class…ever. While a business class or two might have been good for me, I’ve learned much of my craft from good ol’ fashioned “view source” and I’m good at it. You won’t find many people who have the blended skillsets I possess.

But reality must come knocking at some point, and generally you have to pay for the door unless you want it in your living room. Freelancing has been a long, lonely road to this strange place where I find myself today. Not exactly a confidence-instilling track record.

Over the last two months, I began searching for other work outside of freelancing. My thought was to find something consistent to work on, earn enough to pay rent, and use the rest of my time to slowly build my business back up for another leap. So far, this has looked like me filling out job applications on public wi-fi, helping with a paper route to relieve some of the pressure, and working on every web development project I can get my hands on. Not really the best way to build a business.


Recently, I have been spending some time with 40Digits (whom I am very thankful for) and they let me get out of the house to work around other developers for a little while each week. They’re the best. It has been critical for me to gain these interactions and meet other web folk in my little town.

Home office, remote office, paper route, part-time gig, personal/church projects…things have been crazy as of late. I’m running at full speed right now to redeem every moment of every day. I can honestly say that I have never had the clarity of purpose nor the confusion of pursuits that I do right now. Everything is all-in all the time, which is not a good way to live, but things are starting to shift. I see little glimpses of the future here and there, even if that means spending 8 hours in a remote office, 5 hours at McDonald’s, and 2-3 hours at home some days.

So why go to all this trouble? What purpose could be there be for all of this toil – why not just pack up and move to a town where I could work for someone else? There must be more to this story, right?

As I seek an answer to that question, I see two basic lines of thought: I move, live alone, and lose the connections I have made here in Springfield. Sounds dangerous, until I ponder staying put. It may mean more time spent working alone, building toward the future in the wee hours, the dry seasons, the fitful nights. Either way I see my former timetables being stretched out over multiple years…again.


“To be a successful entrepreneur, one needs a vision of one’s work. If we dream, we will be inspired beyond the straight jacket of the everyday world. There is a profound connection between art and enterprise, which allows businesses to overcome its limitations and break the rules…Connect, connect, connect with artist-friends. The sorcery and charm of sharing our view of the world make it one of the most treasured of all creative arts.”
Bernardo Medina

It took awhile to get here, but eventually I realized the complete futility of the work of my hands. It is obvious to me that God alone could actually take my labor and produce a profitable return. I mean, He cursed the ground, so doesn’t make sense that He would could bless our efforts?

Any amount of toil produces a profit, but it doesn’t really mean anything unless we’re doing it as unto Him. All I know to do is wake up, dedicate everything I do to His leadings, and try to apply myself in the ways laid out in His word. I’m certainly thankful that I am not wholly responsible for the results, and can only pray that He will multiply the return if I keep Him at the center of everything I do.

My efforts are inadequate of their own accord, but done through Him, I see them do things that go far beyond my abilities. I really do not wish to wrestle with Him in a battle for power or preeminence in whose labor is being applied to these tasks.

I don’t know exactly what the future holds, but I do know that this road stretches on for a while. Whatever it takes to build, “A family who will stand the test of time…” is what I’m after. Along the way I hope to meet great people, build great stuff, and take tiny steps each day that point to a great future in, well, whatever I call my freelance business in the future.