Strap in kids… it’s about to get heavy.
It might surprise you to hear this, but my career trajectory was far from being a straight line from Point A to Point B… it was all over the friggin’ map.
And at one point, I hit a very clear crossroads.
I was living in the SF Bay Area at the time, and was about to lose the apartment I was living in because I couldn’t afford it anymore and couldn’t afford to move.
I was surviving off unemployment benefits and desperately trying to build my freelance hustle with little to show for my efforts. My friends and family begged me to get a job, any job, just to make it work.
But I had this little voice yelling at me, from somewhere deep in my gut. It told me I was where I was supposed to be, and that this was the career move I needed to make.
To this day, I can’t explain it logically. I had people that love and care for me, who were willing to take me in while I got back on my feet. All it would require was me going back home to Texas to live with my parents, and probably crawling back to my old job waiting tables.
It was either that or stay in California and live in my car.
Can you guess which choice I made? (Hint: it’s the one that seems pretty fucking stupid and reckless)
I chose to live in my car. My parents were NOT happy.
Hell, I was not happy.
I cried myself to sleep most nights thinking about what I was getting myself into, worried about how I was going to support myself.
One image is burned into my brain from that period:
I remember sitting alone in the apartment on a mattress one rainy night, applying for any and all copywriting and marketing jobs I could find, and crying. All I had left was the mattress and a suitcase packed with toiletries, a few changes of clothes, and my laptop/business cards. I’d put everything else (what little I actually possessed) in storage, and figured I’d just make up the rest as I went.
With a couple days to go until I had to be out, I had secured a sleeping bag and some window coverings for my car. I’d found a cheap insulated bag to carry ice for my cat’s insulin. I’d scoped out places to park my car that seemed relatively safe, and less likely to be hassled by cops and passers-by.
The final day, I handed over the keys, grabbed my suitcase and my cat, and set off for the great unknown.
Thankfully in that part of California, most days are fairly mild in terms of temperature. I let the cat bask in the sun on my front seat with the windows down as I sat outside at Starbucks.
And I shit you not, checked my email to see that I had a job offer. The VERY SAME DAY I was out on the streets.
I saw a glimmering of hope… I wasn’t quite out of hot water, but this was a great sign. I’d applied for that job months back and had gone through multiple writing tests. This was the first time I felt like a legitimate writer… someone wanted to hire me for a writing JOB!
So I stuck to the plan that first night… camped out in the car.
The next day, I tried to find the cheapest no-tell motel I could, figuring it’d be temporary.
I’ve stayed in some pretty cheap places before, as I’ve driven across the states multiple times by myself. But NEVER had I stayed in a place quite like this.
The room was about 10-ft by 10-ft, with a Murphy bed (the kind that folds up into the wall) and a small sink. It smelled like the only cleaning they’d ever done was to walk in, sprinkle some scented carpet powder, and walk right back out.
No ensuite bathroom – to feel any semblance of clean, you had to wander down the hall to the shared bathroom/showers.
The first morning I woke up and found a shattered crack pipe outside my door as I headed to the communal shower.
I readied myself as best I could, fed the cat and gave him his insulin shot, and met up with a prospective client to put on a happy face and pretend everything wasn’t horrible. It must have worked, because I left that meeting with a signed agreement and a check.
Later that day, I was sitting at Starbucks again, getting started on my new project. Some friends stopped in and wandered over to my table to ask me how I was.
That was the first time the facade cracked… I’d meant to say, “hey I’m great! How are YOU?”
What I actually said was something unintelligible about being in a horrible motel in between snot-bubble sobs.
They graciously offered to let me crash on their couch, and my fierce Southern pride instantly and adamantly denied it. They hugged me and said it was good to see me… and left me to my work.
Later that night, back at the horrible motel, I cried myself to sleep again while the cat did his best to calm me down.
The next morning, I got up to shower. Some random lady was drunkenly staggering down the hall, and informed me “someone made a mess of the bathroom”. Someone (probably her) had Exorcist-barfed ALL OVER the communal bathroom. No surface was spared.
I ran back to my room and immediately called my friends from the day before and sobbed as I asked them if their offer was still good… I quickly ran down what I was dealing with in the motel and they invited me to come over immediately.
Never in my life has checking out of a motel felt so good.
The rest of the story is actually kinda anticlimactic by comparison…
Over the next few weeks, I couch surfed as I got acclimated to the new job. When I got my first paycheck, I reached out to my network to look for a roommate. I met someone amazing and wonderful (she sold wine for a living – it was a match made in heaven), and moved in shortly thereafter.
I slowly rebuilt my trainwreck of a life, one painstaking day at a time.
Eventually I outgrew that role, as it was a part-time, junior writer role. When I started feeling restless and like I needed more of a challenge, I tried my hand at a full-time salaried role… and got it, instantly tripling my take-home pay. I went on to build and train a team. Earned a promotion to senior copywriter. Eventually felt confident enough in both my copy and my survival skills to try that freelancing thing again.
And now you’re all caught up.
I tell you my story for a reason…
I hear all the time how people think I’ve always had everything figured out.
“You look so put together, it’s hard to imagine you struggling.”
Consider this: sometimes everything has to fall apart for you to know how it all gets put together. That’s been my experience, at least.
If you’re trying something new and scary and you’re not making the progress you’d hoped… that doesn’t mean you’re a failure or you’re not cut out for this. It just means you found a couple ways that aren’t working for you, and now you need to find another way.
I’ve got a bit of potentially shocking news for you… none of us has it all figured out. Not even your gurus. They’re all guessing as to what their next big thing is going to be and hoping it’ll work like they imagine.
Just like you and me.
Every single one of us has to fail to find the best way forward.
I mean, theoretically there could be a few lucky SOBs who fall into the right gig and never have to struggle.
But for the rest of us, failure is part of the process.
You could let it kill your hopes and dreams, stopping you dead in your tracks…
Or you can keep moving forward, knowing someday it’s going to make a killer story.