The year was 2015. I was happily married and living in the quaint coastal town of Sebastopol, California, my second child had just arrived, and I was no longer a freelancer. I’d gotten hired by one of my clients a few months prior to work full-time at their consultancy.

“I guess the freelance or solopreneur lifestyle just isn’t for me,” I told a friend at a holiday party. “It’s so nice to have a regular job that pays a decent wage. Freelancing was just too stressful, too uncertain.”

“Ah, I wouldn’t count it out just yet,” replied my friend wisely. “You might find yourself itching to get back in the game sooner than you think.”

Little did anyone realize I would soon be forced to get back in the game in short order.

Why I’d Left Freelancing Behind

Most of my career I’ve been a freelancer. I started building websites and getting paid for the privilege all the way back in 1997. It all began because I’d created a website for my family Celtic band, Distant Oaks. Pretty soon other folks in the Celtic festival circuit started coming to me asking for help in building their websites. “And how much do you charge?” they’d ask. “How much are you willing to pay?” I’d rejoin as I twirled my teenage peachfuzz of a mustache. Kidding! I pulled an hourly rate out of my hat, and it seemed agreeable enough. My freelance business was born.

Many years and harrowing tales later (some of which will be covered in this very series!), I’d had enough. I was fried, extra-crispy. I was sick of all the headaches of finding clients and tracking down payments and dealing with the overhead of taxes and insurance and other administrivia. My wife was pregnant with our second child and I knew I’d need to take time off to help her, watch over my firstborn, and get acquainted with my latest offspring.

So I approached my biggest client and asked if they were hiring. A short while later, they opened up a position for me and I was all set. My life as a freelancer, over. A salaried man once more.

“We Need to Talk”

Months later, in the early days of 2015, I’m at my desk in an industrial-chic office overlooking the Petaluma River, when my boss comes over. “Hey Jared, we need to talk. Let’s go grab a coffee.”

“Yes bosmang” I respond in my thick Belter Creole dialect. (Haha, I wish! I’m such a fanboy of The Expanse…)

Anyway, we head outside, grab a pleasant table overlooking the water, and we have The Conversation.

“Jared, it’s been great working with you over these past months. You’re doing a terrific job. Unfortunately, our business is headed in a different direction. As you know, you’re the only person working in your particular division right now, and we’ve decided to close that division. I’m sorry, but I’m going to have to let you go.”

So much for being a salaried man.

Uh, Now What?

I’d effectively shut down my previous freelance business, I had lingering debts my salary had barely made a dent in, and I had a growing family to take care of. While the consultancy graciously passed their client off to me I’d just recently begun working with, it certainly wasn’t a full-time income. I needed new clients and I needed them fast.

Or, do I simply spruce up my resume and find full-time employment elsewhere?

Decisions, decisions.

Honestly, it wasn’t much of a decision. As much as I hated to admit it to myself, I actually hadn’t been that happy working for The Man (even though it was a very, very nice Man). My friend at the holiday party was right. I was itching to get back in the game. Being a freelancer—even with all the risks and twists and turns—suited my personality. I have always been, and shall always be, a solopreneur at heart.

Six Years Later…

That first year was hard. 2016 was even harder. I’d arrived at the end of my first year with no clients left. None! Thankfully a couple of new projects emerged at the last minute right before Christmas, and so I wasn’t simply twiddling my thumbs come January. But it would take quite some time and much gnashing of teeth to bounce back.

Thankfully, I’m here now (in Portland, Oregon no less!) with an established client base, solid income, and a growing reputation in many web dev communities online. I think it’s safe to say freelancing has finally worked out. But I still think about those crazy times in the mid 2010s and wonder what would have happened if I’d taken another full-time position. It might have been smooth sailing. It might have been the path to Easy Street.

But I would have been miserable.

Instead, I feel alive.


Stay tuned for next week’s installment of Tales from Decrypt where I chronicle everything you shouldn’t do to treat a problematic client. Hooray!