Remote Work Refined — A Short Personal History

Remote Work Refined — A Short Personal History

I have alluded in the past about my goal of finding remote work. I’d like to take the time now to fill you in on the past fifteen years, so that my remote job search has some context for you.

High School Dreams — Yachts, Girls, Mansions, Jets

A drone's perspective of a boatyard.
Photo by Josh GUnsplash

I was a pretty typical guy during high school, especially when it came to my dreams of the future. I had my objectives pictured so clearly in my mind. So did my best friend, and turns out we shared the same vision. We envisioned a flashy lifestyle.

Yachts. Girls. Mansions. Jets.

How we would get them, we had no clue, but get them we would.

(Now, we are both stuck in IT jobs and desperately trying to get out. Go figure).

Experimental 20’s — Marriage, Business, Corporate America, Failure

Photo by Tim MossholderUnsplash

After high school life became very interesting.

I did a single semester at a local college. Not for me. At all.

Started taking flight lessons. Flying and being a pilot has been a dream of mine for as long as I can remember. Maybe I could be a career pilot of some kind?

Long story short, for now, I didn’t finish. I got so close, but a few different things contributed to me not finishing.

As far as work during this time, I went from selling stuff on eBay for myself, to selling stuff on eBay for someone else, to managing a warehouse and handling logistics for trade show equipment. No prior experience for any of this, just learning as I go.

Next up, marry my high-school sweetheart at 21, quit the warehouse job, work for my dad, quit that, almost open a coffee bar in a corporate center, that falls through, land a call-center job and last a month there, interview well enough at an IT consulting company and get a job that I excel at and keep for 2 years.

I quickly learn that corporate America is as good a fit as college. I hate it. Every. Single. Second. So I begin the early morning and late night hustle.

I start with writing. Applying for writing jobs, looking for guest blog posting opportunities, submitting articles to magazine and news paper articles, grasping at anything I could get my hands on.

Nothing landed.

So I started a personal finance blog with my wife. We wrote new articles daily. Started a podcast. It was awesome. It was fun. It was 2008.

Just when it was getting good, we stopped. The site was probably brining in $300 per month from ads and paid posts. I was making money with my writing and I quit. I got distracted is what happened and is what stuck for the next 10 years or so…

Ok, that was 2008. Here’s what happened next until 2015 or so: -

  • January of 2009 we decide we want to move. We pick Wilmington, NC. We plan a vacation there for June.
  • My IT job is now technical writing…which is so boring.
  • I start a business on the side selling screencasts. I do it for free to build a portfolio, and quit my job in July because I thought I could.
  • November of that year we move to Wilmington.
  • My business flounders once we move.
  • I have to get a job and become a barista (and love it — but minimum wage is unrealistic).
  • We move back to where we came from in 2010.
  • More floundering. I work for my dad for a minute.
  • I’m promised an internship and a job at a church. Turns out the pastor lied to me. Go figure.
  • I start my own business again — this time building websites. I do pretty damn well at this. This one goes from 2011 to 2014. A good streak for me.
  • Summer of 2013 — our son is born.
  • December of 2013 my business bombs out and I find a job to keep finances up.
  • I climb the ladder quickly. It is IT again and I’m determined to succeed.
  • By January of 2015 I’m over it. But I’m not sure where to go next, so I stay. And I’m still there. But I begin actively searching for what is next. I start with writing, because that is what I love, but get distracted.
  • Then, a year later, I turn 30.

Realistic 30’s — Family, Priorities, Maturing

A focused man working on a sticker-covered laptop in a coffee shop
Photo by Tim GouwUnsplash

When I turned 30 things really clicked for me. I knew for a fact that being a desk-jockey, a paper pusher, a Corporate America lifer, was not at all for me.

Sitting at a desk all day doing work for someone else kills me. It is boring. And boredom is probably one of the best ways to torture someone.

So the year I turned 30 is when I began to look at working remotely. On my own business or someone else’s. I first started looking into building a business of my own (because that has always been my dream and goal). I went down this path for 2 solid years. I experimented with niche websites, authority websites, internet marketing (scams), hand-letting, Etsy (getting desperate at this point), creating an online course teaching people how to build an online business…and then, in January of 2018, back to writing.

The foundation of those two years was very simple. I felt, and still feel, that a desk job is the worst job if I want to see my family. Evenings and weekends is not enough for me. I am entirely unsatisfied with this type of life and cannot continue any longer. I want work that I enjoy, that provides for our financial needs, gives me freedom to be with my family as much as I want to be, and also freedom to travel as much as we want to.

Writing fits all of that. Perfectly. And it is a literal full-circle back to what I was doing 10 years ago. Writing and making money at it.

Writing — My Refined Remote Work Goal and Strategy

A pair of glasses and a pen on an open notebook next to a laptop
Photo by Trent ErwinUnsplash

Not only does writing fit perfectly, it is what I actually want. It’s what I have always wanted. But I became so distracted with what other people outside of my immediate family (my wife and I) thought I should be doing that I lost myself in the process.

So here I am. Once again back to writing and looking for ways to make writing a full-time thing. Hoping that all of the technical, procedural, and process oriented writing I have done for the past 5 years will help more than hinder my search.

Remote work is the ultimate goal for me. Remote work writing is the perfect scenario that I am now working on. Writing will meet the requirement of doing what I love to do. The remote part will meet the requirements of seeing my family more and allowing us to travel more as-well.

This is going to be an open-ended conclusion. I am not sure where this is going to lead, or how it will go. But I plan to document things here as I progress down the path of attempting to create a life of writing full-time, more time with my family, and hopefully traveling along the way.

Aaron Aiken @aa