In March 2011, I decided to perform an experiment: what if I tried self-employment?
Before Going Solo
By springtime in 2011, I had eight years of professional experience. I’d worked as a full-time employee for various companies in their software and technology departments. By accident I ended up specializing in ERP: Enterprise Resource Planning (exactly how that happened is a story for another day). I quickly realized I’d found my niche and something I really loved (and still do).
After stints with businesses supporting their ERP software, I joined a Microsoft Partner firm. Our purpose was to sell ERP implementations and services to companies around the USA. I had several roles at this firm: Consultant, Project Manager, Technical Advisor.
It was challenging and a great experience for all the wrong reasons: the business effectively collapsed 12 months after I joined, due to a massive churn of consultants (another story for another day). My experience there taught me many valuable lessons about how not to run a consulting business. 🫠
Yet for the first time in my career, I was unemployed without another job already lined up. This was very troubling and nerve-wracking.
Making the Decision
“So now what?” I asked myself. My first experience at a consulting firm had been disastrous; I was burnt out, and very reluctant to retry at another firm.
Yet I’d also spent years in traditional, full-time employment. I knew where that road probably led: I would work extremely hard and shine bright…for about a year or two. But I would inevitably feel held back and get frustrated. I had huge energy and ambitions. Tech life in the 2000s was very different from today.
But there was a third option: continue being an ERP consultant and developer, but a self-employed one. I had a family history to reflect on; both my parents and grandparents spent most of their professional careers self-employed. Not in technology like me, but the core concepts are identical:
- Find clients and work.
- Perform that work as best you can.
- Send invoices and collect payment.
- Rinse and repeat
Why It Worked Out
The short answer is networking. Before I went independent, I’d already spent many years:
- Attending local meetups with people working on the same software.
- Networking with functional experts, developers, and consultants in the Microsoft ERP ecosystem.
- Attending conferences and conventions. At first just listening and mingling. But later I began speaking, leading breakout sessions, and teaching pre-conference courses. In 2014 I received one of the first AX User Group awards for excellence in the Dynamics AX community.
So my early success with self-employment came almost exclusively from referrals and reputation. Work found me because I’d previously participated and contributed. Between that and a measure of good luck, I didn’t need to spend much time on marketing. Sure, I wasn’t on track to become a millionaire or build my own consulting firm. But I was doing very good work and living comfortably.
What I Enjoy
There are many things I love about self-employment, but here are some big ones:
-
The wide variety of clients and problems. Work is never dull or boring. Even when I meet clients with challenges I’ve previously solved, each has their own unique spin or nuances. If variety is the spice of life, then I like my work with plenty of Cajun and curry. 🌶
-
The ability to say “No thanks”.
In corporate environments, technologists rarely control their clients, tasks, or priorities. You can voice disagreement, but leadership decides. Merging companies, overloading clients, cutting staff, relocating HQ to the Sahara—you’re either on board, or you find a new job.
Self-employment changes that. Too much work? Decline it. Bad client fit? End it. Your decisions have consequences, but you finally control them. The autonomy to refuse what you disagree with is both refreshing and empowering.
-
Pride in my work. I have a very real, tangible impact on my clients and their successes. What I’m doing matters. And if I ever sense I’m -not- being effective? Then I can change my own strategies and tactics to achieve a better outcome. I can experiment and be creative. I can be conservative or adventurous. So long as I’m adding value through hard work performed with honesty and integrity, it feels good to be doing good.
Perks
-
Depending on your career and preferences, you’ll likely save on car expenses, clothing, dining out, and more — though higher taxes may offset those gains. 🤷
-
Work conditions are your choice. Enjoy having the radio on all day? Go for it. Prefer absolute silence? Sure, why not. There’s no one to argue with you about these things. Brew the coffee of your choice, put popcorn in the microwave, or have some durian pizza for lunch.
What I’ve Struggled With
Doing the Unwanted Work
Beyond the work you want to do, there’s the work you have to do. Without discipline, it’s easy to procrastinate administrative tasks—timesheets, invoices, billing, or whatever falls outside your core expertise. Self-employment means handling everything that needs doing, even tasks you’re not proficient in or comfortable with. It gets easier with practice and commitment.
Planning Your Workload
Imagine someone contacts you and says: “Hey, heard great things about you! Can you help me with Project XYZ starting in March?”
Well, that’s a surprisingly difficult question, isn’t it? Will you actually have the availability and bandwidth next month? What about your existing clients and relationships? There’s nothing on your calendar for March (yet). However, that project you’re doing for Acme Corporation may not finish on schedule. And what happens if Sarah and Sam call you with another data migration request?! 😬
It’s nearly impossible to know how busy I’ll be in the future. And there’s only one person doing the work: me. If I take on too much, and I’m lucky, I’ll be working late nights and weekends to compensate. Worst case, if I overload my schedule, it could result in poor/delayed work for my clients.
Likewise, I’d really prefer doing billable work as much as possible. It’s really no fun going a month or two with tiny paychecks. Or none at all.
Ultimately, I’ve found that predicting availability is far more art than science. I tend to be conservative and favor quality over quantity. Other consultants enjoy playing it more loosely, and don’t mind burning the midnight oil regularly. When in doubt, there’s always the infamous Magic 8 Ball to rely on. 😉
Advice on Working From Home
Discipline and boundaries have helped me.
-
Work Consistent Hours. My alarm is set for the same time, every day, whether I have projects and meetings or not. If I don’t have client work, then I’m spending time planning, learning, networking, side projects, marketing, etc. It’s important to form good habits. You’ll thank yourself when the busy times later arrive, and you’re already comfy and accustomed to working a solid, productive day.
-
Take Regular Walks. I cannot stress this enough: take lots of breaks and go walk around. The human body was not meant to sit with butts planted in a chair for 8-10 hours at a time. It’s not healthy. Go for a stroll, stretch everything out, and get some cardio. It’s far too easy to stay heads-down focused, only realizing later it’s been more than a week since you left the house.
-
Have an “Office Area”. When you work from home, your home may become nothing but work. It’s critical to maintain balance. Designate an office area. Try to keep your work and laptop inside those boundaries.
Places like my living room, bedroom, and kitchen are non-work areas for me. Sure, I may -talk- about work. Same as I talked about work in the evenings back when I commuted home. But try to actually perform your work in designated areas. If you’re in this area, you’re working. If you’re outside of it, then you’re off duty.
Having these boundaries is helpful. In your office area, you’re focused and doing work things. Everywhere else, you’re a friend, partner, parent, or whatever you need to be. When you mix them together, work inevitably tries to dominate or disrupt the rest of your life.
My Current Challenges
In 2019 I deliberately left Microsoft ERP behind and switched to ERPNext. I put a lot of thought and planning into that transition: years of learning new programming languages, platforms, pitfalls, and ERP know-how. It was a huge endeavor.
But besides the technical effort, this -also- meant “starting over” in terms of community and social networks. In the Dynamics AX world I’d been well-known and respected. But there were hardly any ERPNext customers in the USA, much less community. “I’ll tackle this problem in 2019 and 2020”, I told myself.
But then Stuff Happened. Medical things. Covid pandemic things. I leapt at the first opportunity that knocked on my door, and ended up working exclusively for one client for 4.5 years. I had very little community outside that project.
So nowadays I’m trying to play “catch-up” in terms of networking. Trying to explain who I am and what I do. With an ERP platform that, while very capable and cool, -still- hasn’t achieved name recognition in the USA.
Lesson I Learned: Get involved in communities early, and keep it up. Don’t get too comfortable. Stuff happens.
Hope for the Future
Fifteen years in, I’ve never felt more capable as a software developer. I’ve got everything I need for myself and my future clients. And I’m not doing this completely alone anymore: two years ago I took on an apprentice and protégé, who’s learning The Way Of The ERP under my mentorship. I’m hopeful we can collaborate on new projects.
I’m working with a coach to help me navigate this next phase. And slowly but surely, I’m building connections in the Portland and Vancouver community — people who value the same things I do.
The transition was harder (and far longer) than I expected. But I’d rather be here, doing work I love and believe in, than anywhere else.
If any of this resonates—or you’re thinking about making the same leap—I’d be happy to chat with you.
~Brian