After Two Years, Do I Find Self-Employment Worthwhile?


In March 2015, I started working for myself exclusively. That is to say, I went from working for someone else full-time while also operating my own company full-time to working strictly for my own company. How am I feeling after nearly two years of self-employment?


Working for myself has proven to be fulfilling. I like the correlations to be found among opportunity, effort, risk, reward, and failure. I can weigh all of those things, make a decision of how to proceed, and benefit (or suffer) directly in accordance with my decisions. That is fulfilling to me.

Suffering, by the way, isn’t a bad thing. We could all stand to do a bit more of it today, so that we do a bit less of it tomorrow.


I am free of silly processes that cripple my ability to get things done, not that I believe process is inherently bad. With my own company, I still have to define processes, but I can keep them both streamlined and fluid. I’m also free to let the people that work with me define their own processes, with me providing only the input required to achieve the desired result.


When working for other employers as an IT professional, I labored long hours, well beyond the normative forty. I was often part of a 24×7 on-call rotation for which I was typically not compensated. Depending on the employer, I was required to be reachable at any time no matter where I was, i.e. lunch, family vacation, a trip to the mountains, etc. For some employers, I was even required to carry a tetherable phone and laptop on backpacking trips — just in case. Some employers were more caring and considerate in this regard, allowing IT staff to truly disconnect from the office. Most were not.

The nature of IT operations work is that production-impacting projects are to be done outside of regular business hours. I do not miss these sorts of projects. Hovering over a laptop, pasting in pre-built configuration changes while sitting on the floor of a droning, freezing data center at 2am is never a good time.

My wife was always supportive of my late night projects and on-call disruptions to our personal lives, but it wore on her. She covered for me at social events or with the kids when required, and never complained about the long hours I was frequently gone. But still.

After twenty years of that lifestyle, I’ve found a much better balance between work and my personal life working for myself. My schedule is more predictable now. I can break away from the office without the nagging fear of being called or having to lug a laptop everywhere I go. I can take a day off whenever I need to. Yes, I find myself at airports more often due to my work, but that’s predictable now. I usually know months ahead of time where I’m going and can plan accordingly.

Balance is important. It’s taken me almost two years to get to the point that I can sleep consistently. I no longer dream about some crisis or other at work that might demand my attention. I haven’t been awakened by a manager asking me to take a look at an issue for a long time now. I no longer obsessively monitor infrastructure status screens, seeking dead canaries.

These days, when I’m at work, I do my work. Yes, I have a schedule. I have deadlines — lots of them, in fact. I have meetings. I have a busy calendar. But when I leave for the day, I’m done. As a company owner, I could obsess and fret over any number of details, but I’ve found that I’m much more effective when I take time each day to step away. Working for myself allows me to maintain that balance.


Running a company, even a small one, is complex. I have employees and contractors. I have a business partner to make joint decisions with. I have customers. I have city, county, state, and federal governments that collect taxes from my company, me, or both. I have cash flow to monitor. I have payrolls to fulfill. I have insurances that require periodic review. I have bills to pay. All of this comes in addition to doing my work as a content creator.

While I farm as much of this back office operational work out to other companies as possible and automate where I can, it’s still ultimately my responsibility as a business owner to make sure all goes well.

But, returning to the point about fulfillment, I don’t mind the extraneous work. I’ve become increasingly efficient at it over the last two years. As the people that support our back office learn our company better, they, too, have become more efficient. The complexity of running a small business has gotten easier over the last couple of years — not harder.


There is a manageable amount of stress in my life as a small business owner, related to the complexity itemized above. I can summarize my stress points thusly.

  • Taxation is complex. I lack the legal expertise to comprehend what is required of me and my business. To relieve this stress, I retain a tax accountant at a reputable accounting firm.
  • Payroll is similarly complex. To relieve this stress, I have farmed out payroll to a company that specializes in paying not just my employees, but also the various groups that take deductions from the paychecks of my employees. They also handle the quarterly filing and reporting related to payroll.
  • Cash flow is a jagged line, not a straight one. To cope with this stress, I maintain a larger than ideal cash balance in business accounts. This irons out the lumpiness of accounts receivable.
  • Forgetting deliverables bothers me. To reduce the stress of deliverable fulfillment, all contracts live in a job tracking system. We also have a weekly meeting to be sure all obligations to our customers are being met. With this system, very little falls through the cracks.
  • Losing track of leads also bothers me. Sales cycles can be long, and we’ve learned to be persistent to keep up with inbound queries. Conversion takes time. Keeping track of sales conversations using a leads database has relieved the stress of keeping the sales pipeline full.

In summary, putting systems in place is critical to reducing the stress of running a small business.

Beyond the systems themselves are the people operating those systems. For example, the Project Manager position is the hub around which my small company revolves. As a company owner focused on content creation, I lack the time required to properly manage projects. I rely heavily on my project manager to make sure we’re on track. Thankfully, she’s gifted in this role.


I’m glad I didn’t move to self-employment in the hopes of getting rich, because I am not on a fast track to wealth. That said, the paycheck is fine, the net outcome being similar to what I was earning as a network architect. Plus, I own part of my company. That could be worth something someday.

Might I go back to working for someone else?

Yes, perhaps, but that’s not a situation I’m looking for right now. Even so, working for someone else once again is not a scenario I dread, either. If I need to do that someday, I will be just fine. But I find the fulfillment, balance, and reward of working for myself outweighing the stress and complexity. At least on most days.

There’s a key element to all of this, though. That is that the business I’m in makes financial sense. We are able to pay the bills without worrying from week to week whether or not we can keep the lights on. That’s at the root of why self-employment is working out for me. If I was constantly anxious about whether or not we’d land sufficient business, I don’t believe my psyche would tolerate it. I’d de-stress by going to work for someone else so that I didn’t have to be concerned as much with a paycheck.

However, as it happens, we don’t have that challenge. If you’re thinking about taking the self-employment plunge, that’s a big consideration you’ll need to reflect upon seriously. How well can you tolerate lumpy cash flow and long sales cycles while your business is ramping up?

In my case, business ramped up for over 5 years as a side project. Only then was it de-risked enough for my personal tolerance levels. That slow ramp-up scenario is different from taking a headfirst plunge into unproven waters.

About the author

Ethan Banks

Most people know me because I write & podcast about IT on the Packet Pushers network. I also co-authored "Computer Networks Problems & Solutions" with Russ White.

Find out more on my about page.


Most people know me because I write & podcast about IT on the Packet Pushers network. I also co-authored "Computer Networks Problems & Solutions" with Russ White.

Find out more on my about page.

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