It’s three years and counting working for myself, and that’s amazing

Now entering four years.

Should have posted something about this in October, but forgot to. In mid-October 2014, I quit my full-time job in marketing to start working for myself. It was a decision I had long pondered. A few years prior, my work situation has changed drastically and suddenly after 13 years with the same company, and while at the time I was blindsided, it was a good thing. Kicked me out of a rut. I had been deeply unhappy and seeking change, and suddenly change was forced on me. It was a blessing.

Almost got caught in a new rut, but talked a lot with the Mrs., about goals, about ideas, about different ways to live.

I remember the day I decided I was really going to do it. We were at The Wonder Bar in Asbury Park, surrounded by dogs because we decided to go during Yappy Hour. This isn’t code. They let dogs roam the place on Saturday Yappy Hour!

It was a gorgeous autumn day. Sun was amazing. The ocean was crashing nearby. We were talking through this stupid idea I had, this notion of not working for The Man anymore and instead carving out my own path. It was a terrible idea. An idea no mature adult considers. But I considered it, and she supported it, and we went round and round until I realized I wasn’t trying to sell her, I was trying to sell myself, and before long I said to her, “Holy shit, I guess I’m really going to do this, aren’t I?”

And I did. Went into work on Monday, talked to the right people, made arrangements, “quit” and instead became a part-time contractor for them, and started working for myself.

I was, of course, a little uneasy about the whole idea. I had been brought up on the notion that you got up, went to work, came home, and rise/repeat the rest of your life until you died. It’s what Real Men did, so it’s what I did.

But holy shit, what a miserable existence.

Won’t say it’s been easy or smooth or anything of the sort. Money is up and down. Clients come and go. Sometimes the work is great and sometimes it’s soul-crushingly mundane. Sometimes I have to fight to get paid by the people who hire me. That sucks. Sometimes I have crunches where I work non-stop, every single day, long days for weeks and have to turn down social engagements, and other times I have a week where I twiddle my thumbs and practice balancing spoons on my thumbs and wish someone interesting would text me.

It’s MY time, though. Any success is mine. Any failure is mine. I feel like that’s how it should be.

It didn’t all turn out the way I thought it would. Thought I’d feel freer and more refreshed to pursue creative projects, but instead I’m creatively burnt from being focused on work all day, especially since I work in the same place I create. No separation, therefore no escape. I make this post from the same place I write about the loss of great people for Legacy or pen website copy or surf Reddit for threads to get annoyed at or upload my podcast or whatever. Had a lot of bullshit money-making writing projects I didn’t pursue (including writing erotica under an assumed name!) and I’m mostly glad I didn’t. Still managed to independently publish two books of television criticism during that time (The Walking Dead and Mad Men), so that’s good. And finding new work? It’s a struggle. I can’t sell myself. I’m bad at it. I actively hate it. All my work comes through word of mouth (so I guess I’m blessed for that). And while good times are good, bad times are thin, thin, thin.

And yet, whatever. Whatever! Those may be real things I need to tackle, but the fact remains that I have been doing it myself for three full years now. THREE YEARS. Holy shit!

How did this happen? How on Earth did a broke ass dude who most certainly did not win the lottery and whose main skill involved being a sarcastic asshole manage to just toss aside the idea of working like normal people do and make his own way? I have no idea.

I mean, I have some. A supportive wife is a huge part of it. Huge. Couldn’t do it without her (but don’t tell her I said that). Having a plan and a more importantly a fallback plan was a big deal. And having an amazing butt helps. I can sit with the best of them.

But mostly, I couldn’t write a guide. I’m still mostly baffled by it. And if I’m honest, entering my fourth full year, I wonder if I’ll be starting year five working for someone else. Depends on the money. There is, after all, a roof over our heads that needs to be kept there, and for budget reasons I’ve lost a few clients along the way. They’ve generally been replaced with other clients, but it’s been a holding pattern rather than a gain, and I’d like to gain.

All the same, I’m here. I’m where I need to be. I did it (sort of). I maybe haven’t written the novels I’d hoped to and all that — was invited to a writers’ retreat last summer and realized just how far behind I am in that regard — but if you’d have asked me 20 years ago if I thought I’d be determining my own course I’d have thought you crazy. Still going to try, though.

I’m only 45. Keeping this shit up for another 20 (or 30!) years is a total pipe dream.

But I’m going to focus on the “pipe” part instead of the “dream” part.

Because pipes are real.

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