It all started back in 1999. I’d been using Linux since 1996, and I decided to take a hiatus from a successful stage acting career, simply because my mind wanted to expand its horizons for a bit. That led me to studying Computer Science, where I could put my experience with the Linux OS to work.

While studying Comp Sci, I happened upon the university’s Linux User Group and decided to join. After three meetings with that group, a representative from TechRepublic walked into one of the meetings and asked a single question:

“Anyone here interested in writing about Linux?”

I wasted no time, shot my hand in the air, and said, “Me. You want me.”

That was some seriously misplaced confidence, as I’d never written for the tech industry before. I’d written short stories, I’d written poetry, I’d written countless essays. Tech articles? Not so much. But that was the arrogance of a college student who was older than his peers and, in some cases, older than the people teaching the classes.

The TechRepublic rep gave me his card and said to contact him as soon as possible.

One month later, I signed a contract to write four articles per month at a pay rate that had me dancing in the streets. This was at the beginning of the dot-com era, so companies were spending like there was no tomorrow.

Four articles. I was young and new to this whole working from home thing.

SEE: IT pro’s road map to working remotely (TechRepublic download)

How I used to work from home

Given my assignment, I did the math:

30/4 = 7.5

I could write one piece every seven and a half days and complete my monthly assignment.

Again… I was young.

What if, instead, I held off until the last week of the month and wrote all four articles? That gave me three weeks to do whatever I wanted! After all, I dropped out of the Comp Sci program, so I had all the time in the world. I already had a BS and an MFA degree, so tacking on another BA seemed like overkill. Besides, I was making more money than I’d ever made to that point–remember, I was an actor, so I lived on ramen and Pop-Tarts in those early days.

I had a plan. Play for three weeks and glue myself to my desk for one.

All went well for the first month or two. And then, all of a sudden, I found myself crushed under the weight of those deadlines. I was stress writing for seven days and found myself thinking, “Is this the best way to go about professional writing?” After all, I was no longer in college, so there was nothing to gain by putting off my responsibilities.

So I swallowed my pride, grew up a bit, and started writing one article per week. That would give me seven days to make sure the article was finished and polished.

Life calmed down a bit. I could breathe during that last week of the month.

Then, something fantastic happened. I received a call from a different person from TechRepublic saying they’ve decided to build a new product called LinuxRepublic (RIP) and wanted me to take charge of it.

Are you kidding me?

Dreams. Come. True.

I immediately said yes, packed up my work-from-home attitude, and took a desk job for the first time in my life.

If I had known then what I know now about working from home…

Working in the TechRepublic offices was amazing. It was fun, inventive, and exciting, and there were some incredibly cool people to collaborate with (those sentiments still hold true today). I loved every minute of it.


There’s always a but.

Something was missing. It was the freedom to work at my own pace, in my pajamas, while listening to whatever music I wanted as loud as I wanted.

Even in those early days, I knew I was built to work from home. I am exponentially more efficient in the comfort and solitude of my home office than I am surrounded by others. There are no distractions, there are no meetings, there are no office antics–not that I mind a good shenanigan now and then.

Isolated, my words flow like butter dripping off a hot biscuit. When there are others around me, that butter coagulates into a thick, chunky mess. It’s one of the reasons why I write all of my fiction at night. With the wife and cats asleep, I can focus my concentration in ways I cannot when the sun is shining and people are milling about.

I didn’t know this early on, and the escapades of working in a dot-com was exciting. However, I was far from productive. And I missed those days of working from home.

Working from home isn’t ideal for everyone

The truth of the matter is quite simple: Some people are self motivators and can make the transition from working in a busy company to working in a quiet home office with ease. Others have a lot of trouble retaining their focus. Once the latter type of person is at home, the world is their oyster and…

  • Laundry calls

  • Kids cry

  • Spouses interrupt

  • Games can be played

  • Errands can be run

  • The outdoors beckons

  • TV can be watched

  • Shopping needs to be done

  • Pets want attention

Working from home requires a different level of concentration and dedication than when working within the confines of a company. You can’t put everything off until the last week and get your work done with a modicum of success–you must schedule your work life and stick to it.

Unlike how I worked back in the late 1990s, I now depend on Google Calendar (almost desperately so). Of course, back then I was writing four articles per month for one client. Now? I write around 70 articles per month for multiple clients, covering a multitude of topics. On top of that, I film a lot of video, and there’s also the fiction side of my life.

I average over 100,000 written words per month.

So, yeah, I’m incredibly busy now. Because of that, I have to be incredibly regimented in my work. I have to live and die by that calendar and ensure my spouse understands that every time she interrupts me, I lose my flow, and it takes me extra time to get back into the groove.

In fact, two paragraphs up, I was interrupted and completely forgot what I was going to say. And then one of my cats entered my office, demanding treats and pets. The wife knows to limit those interruptions. The cat? Not so much.

I’m now holding said cat and typing with one hand.

Cat is now on the floor.

You see how that works?

Yes, I could shut the door to my office to indicate that I am not be disturbed, but that’s not the environment I want to work in.

I know how I work best. It’s taken me a long time to get there. For me, the perfect work-from-home environment:

  • Is filled with music

  • Is set up so that it flows seamlessly into my daily life

  • Functions at my pace

  • Is dictated by no one but me

  • Is open and free to (limited) disruption

  • Includes cats

  • Allows me to wear as many (or as few) hats as needed… and pajamas

  • Allows me to use my creative nature

Would such a work environment function for you? Maybe. Maybe not. Very soon–or even now–you’re probably going to find out.

COVID-19 is changing how many people work

Some never thought that a pandemic would grip the world and cause tectonic shifts in how we live our lives. It’s happening now due to the coronavirus, and many people will have to work from home.

To some employees, this is a chance to prove to the powers that be that working from home is a legitimate option—they can finally shine while working in their pajamas. For others, it’s a rather frightening unknown. Not so much the “how,” but the “can.” It’s not about technology–we all have the technology to work from home. You have a computer? You can work from home. End of story.

The truth of the matter is the “can” is a bit more daunting than the “how.” Sure you might need a new printer, a scanner, or some other piece of technology, but that’s easily acquired. The big unknown is that most people don’t know if they are capable of working from home—if they have the personality, the ability to drown out distractions, or even demand of those they cohabitate with to give them the necessary space and time required to do their jobs.

I speak from experience. It’s not always easy to look your spouse in the eye and say, “Not now.” I tried it for a while, but eventually realized I couldn’t do it. I have to let my wife interrupt me, because it is how we live our lives. To that end, I had to make serious adjustments to how I work from home.

Why? Because I want my work-from-home life and my home life to blend together. I don’t want “Work Jack” and “Home Jack” to be two different personalities. My writer voice is an extension of who I am, and I will not stifle that. So, I adapted and made it work for me.

That’s the biggest challenge to working from home. If I had the ability to go back in time and tell my younger self how to best navigate the waters of working from home, I’d simply say, “Be true to who you are at all times, and your work will always be honest, organic, and worth reading.”

So, to those who are facing the prospect of working from home because of the COVID-19 pandemic, give yourself a bit of time for adjustment. While you’re adjusting, allow yourself to do things differently. Don’t read a bunch of bullet point articles on how to work from home and call it a day, because what works for someone else might not work for you.

Develop your work environment based on your personality and your abilities, and you’ll find yourself far more productive than you can imagine.

Above all, be honest with yourself. In the end, you may find that working from home simply isn’t for you; however, if working from home does suit you, play your music loud, wear your pajamas proud, and be productive.

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Image: TechRepublic/Jack Wallen