I am coming up on my two-year anniversary of quitting my W2 and walking away from my career here in a month. And what a wild ride it has been! However, I will not lie to you and say that I wouldn’t have it any other way. That is pure, unadulterated horsecrap. The first 8-9 months were ROUGH. But that’s putting the cart before the horse.

Timeline

The first thing you should understand about the process is that you need to have a timeline. You need to have a moderately hard date set in stone to reverse engineer your pathway to making that date work.

Look, we humans are creatures of comfort. We default to complacency if we don’t force ourselves out of our comfort zones.

But a little more background is due to my personal story. I was not an entrepreneur, or at least I never considered myself one. But by looking back at my youth and adolescence, that proves untrue. Working for someone else hasn’t ever worked out all that well for me.

• At 15, I got fired from my job of bagging up sacks of squirrel feed. I have no clue how you suck enough at this to get fired.

• Also, as a teenager, I worked for the same grocery store in my small hometown three separate times.

• The most money I ever made as a teenager was when I worked for myself mowing yards and doing other manual labor.

Most of my money went toward my lifelong goal of learning how to fly airplanes. I was blessed to be located near a nonprofit organization that taught teenagers how to fly for very little money. Still, it was not free, and I was no fortunate son with a silver spoon. I paid my way through my pilot’s license, which took me four years to do.

But that is a byway for another time.

Back to the timeline.

2016

It all started in 2016, although I didn’t know it at the time.

I had spent over 13 years of my life in the Air Force, and if have ever been around the military community, you know that it is a way of life, not a career. However, in late 2015 my military career came to a screeching halt.

Thankfully, I was in the reserve component, so it was no longer my livelihood, but it was a major part of my identity. Getting pushed out hurt. I’d planned to be a lifer, and it gave me a sense of purpose. Of course, looking back, I am so much better for not being in that community anymore, but you don’t know that when you’re in it.

But my reserve pay was about $350 per month (net); at that time, we needed every cent.

Looking for a way to make up that money, I stumbled onto Upwork. Say what you want about it, my writing career wouldn’t exist if I hadn’t found Upwork. Besides, back then, it was much smaller and way less scammy.

2018

My wife had been busy raising our kiddos while I worked, which was especially important for the years that I was still running around in the National Guard.

In April 2018, she signed up for a multi-level marketing company to sell fingernail polish strips. Yes, it plays heavily into the story.

2019

Nothing really happened for those first few years. I was earning some supplementary income on the side, which basically replaced my income from the National Guard, but that was about it.

But then, in 2019, something happened at my W2 that made me rethink everything: it went underwater. Not metaphorically. The Missouri river flooded in 2019, and the airport that I used to manage (yes, that was my job before I started freelancing full-time) sits on the Missouri river. Like, right on it. Stupid design IMO.

Ok, so actually, the thing is that my job flooded twice in 2019. First in March, then again in May/June. That is what got me thinking about my future. If the design was that dumb, and the Army didn’t want to spend any money on improving it (they did end up building a better levee right before I left)

It dawned on me that I should take my writing more seriously, especially when I returned to my workplace in the late summer of 2019, and they didn’t even give us bathrooms for months. Yeah. They put a couple of porta-johns out back and called it good. And they also didn’t rip out the sheetrock in the basement commons area for months, so we were upstairs breathing in all that mold. But I guess mold is NBD for the military.

2020

The whole world went retarded.

I wasn’t even a year removed from the above carnage, and the world went insane.

My job felt fairly secure, but it was mostly an illusion. But my wife kept pushing me (thank you, babe😘) to take writing more seriously. Toward the end of 2020, it was becoming clear that the vaccine would be mandatory even for civil servants, and I'd had enough of mandatory vaccinations as a military member.

But I could not envision how to scale my writing. I wasn't really earning much.

2021

My wife had me convinced to leave my job in December 2020. I even typed up a formal letter and signed it. She still has it, actually.

But the military had become so intolerable in 2021 that I had to leave. We weren’t nearly as ready as I wanted to be (not really ready at all to be honest), but the writing was on the wall. So in April 2021, I resigned for real.

Next week: preparations

I could sum up next week’s issue in one sentence: we didn’t have anything set aside, which was a bad idea. Ok, that is a little too doomer-y, but it isn’t altogether wrong.

We made a lot of mistakes, and I know that’s what y’all want to read about, so I’m not going to hold back. Man, that first year of freelancing was rough. Talk about broke.

But don’t worry! It does have a happy… continuance? It’s not an ending because I am just starting to break through and really make it. And I’ll share those Ws with you, too, but just understand that those Ws are the results of a ton of Ls.