150 Days Without Pants: The Business Casual Story
Nearly five months ago, I quit my job as an SEO for a digital agency, packed up my keyboard and took four steps around the corner from my bedroom to chase the glamorous dream of hunching over a keyboard and writing for other people.
I left an environment I’d spent almost five years in – a place where I could come in at 10 without raising an eyebrow, worked with a group of friends and had a lot of control over deliverables. I was also leaving a lucrative field with a scarcity of talent that all but guaranteed a six-figure income if I wanted it.
Instead, I opted for a notoriously undervalued job, where half the writing tells you how poor you’re going to be and the other half tells you how hard it is to get steady work. I had no formal training in writing, spare a few English courses here or there. No journalism or communications degree.
Five months and a 40% raise in my income later, it’s becoming obvious that I couldn’t have possibly made a smarter decision.
That’s the short version of the story. The long version is a little more interesting.
It’s not often I indulge in personal storytelling – at least, not to the community at large. I’d like to call that modesty, but it’s more fear than anything. And five months as a “freelancer” (a word I still cringe at) is hardly enough for me to start waving the victory banner and giving people advice.
Still, I think I’ve got a story worth telling. I’ll let you be the judge.
“She’s absolutely terrible, Jen!”
I was back at my desk at the agency, reviewing the writing of a freelancer we’d hired for a project. Jen, a good friend and a project manager, was often a sounding board in moments of frustration.
“Listen to this,” I said, holding a crumpled up printout – the first draft. ”"This golf course is occupied by luxurious trees.” Occupied? What is this, the blitzkrieg of Poland? Who the hell wants to golf on a course that’s occupied by trees? And how can a tree be luxurious? Just awful.”
This was just one of four batches of writing I’d reviewed so far. In every case I’d had to almost completely throw out what I was given and rewrite it – this in addition to juggling my regular work in SEO. I was not a happy camper.
I had grown up writing, aced my English classes, volunteered for local papers (they had free pizza on Wednesdays) and had accidentally published a book (a story for another time). Still, I didn’t see any future in writing. Newspapers weren’t for me, and I’d rather chew off my fingers than write technical manuals.
I was oblivious to there being any other option.
“What are we paying this chick?”
“$40 an hour.”
“$40 AN HOUR!? Are you SERIOUS?“
At the time, $40 an hour was, in my mind, an incredible sum equivalent to the lofty incomes of civil engineers, lawyers and perhaps Warren Buffet. It hit me like a tonne of Hardy Boys paperbacks: People actually made money writing – a revelation laughable in its simplicity and revolutionary in its truth.
I thought to myself: If a terrible writer could command $40/hour, what would someone who knew what they were doing be worth? I talked to my boss, convincing him to fire the writer and pay me her wage instead. He agreed. The seed was planted.
I was sitting in a church, watching the Tallest Man on Earth.
I sat with a new friend, Chris Pecora – a local graphic designer. I mentioned to him that I was moonlighting as a copywriter. He said if he had any projects, he’d let me know. I wrote it off as a pleasantry.
So when Chris wrote me an e-mail introduction to a friend looking for a writer, it was a bit surreal. Of course, not nearly as surreal as my first meeting with David, a local marketing consultant who had a job that needed doing.
We sat in a coffee shop – him cool and collected, me sweating bullets in my nicest button-down shirt, darkest jeans and newest sneakers. I’m pretty sure I even got a haircut. I had two goals going in to that meeting.
1. To avoid revealing how little professional writing work I’d actually done, and
2. To make at least $40/hour in the process.
We chatted. He liked my little portfolio. And then he asked me, “Alright, so what do you charge?”
I almost pooped my pants.
What do I charge? Thinking as fast as I could, I blurted out an absurdly overcomplicated response.
“Well, we’ve never worked together, so the first 10 hours will be $40.”
“Alright. And the next?”
Crap. I hadn’t even thought about the possibility he’d accept. WhatdoIdowhatdoIdowhatdoIdo?!
Not wanting to sit there making scrunched up faces like a constipated gargoyle, I finally spat out the only answer I could think of.
“After that, it doubles.”
It took everything in me not to fall out of my chair. My first official freelance gig ever, and I had somehow landed $80/hour. I felt like I could buy France. I smiled all the way back to the office.
Fast forward two years.
I’d picked up a handful of writing jobs on the side that made for some excellent beer money. I had also managed to make friends in the digital world – mostly by changing my strategy from “kiss a lot of butts” to what came more natural: “make fun of everything.”
People appreciate humour – most of the time.
Despite having a great boss, SEO was feeling less fulfilling. I began to see limitations in my ability to be effective; the agency and I were moving different directions – them towards the analytical, myself towards the creative – though interestingly I felt like SEO itself was moving the creative route, too.
It was the year after the first Panda update had rolled out – the first blow that got everyone talking about content again. When Penguin finally rolled out, demand for good writers went absolutely Hiroshima.
People were going bonkers bananas for content, and I could create it.
I started thinking seriously about writing full-time, but everything I read said that freelance writing was a terrible career choice. And frankly, spending 10 minutes browsing oDesk is enough to make any creative want to curl up in a ball and cry.
But then again – did I really want to keep trying to force a future in SEO? Despite unparalleled flexibility in my job and being surrounded by friends, trying to win the Google game was turning me into a jaded bastard. My usual sarcastic humour turned into bitter, unfunny tirades. My family noticed how little I was smiling, how low my energy was, how much I seemed to brood all the time.
It wasn’t the job, the people or the pay – I’d simply lost my spark. Writing seemed like the way to get it back. I needed a change.
People might say they want great content – but few put their money where their mouth is.
I was told it was low-paying work; that it took years to break through and that it’d never pay what I could make doing SEO. Over and over, I heard how hard it would be to make a living and that it’d be hard to find steady projects.
I thought I might have a chance.
I had a business background; I could see the big picture. I’d spent almost five years analyzing data to help make clients make business decisions. My history in digital had given me two enormous assets: a network who would trust me with work, and an understanding of exactly what digital agencies were trying to accomplish with content.
But more than any of those reassurances, I wanted to be able to say I went for it – that when my fictional children sat on my lap in the future and asked me “Dad, why are we wearing potato sacks?”, I could at least explain myself with the poetic notion of living your dreams.
So in June of 2013, after struggling with the battle between comfort and adventure, I submitted my month’s notice.
I went freelance as of July 1st. Jobs were coming in, my website launched; things were looking like they might just work out.
And then I got the biggest curve ball of all.
While at MozCon, I got an e-mail from a recruiter, asking me to interview for the role of SEO Director at a massive firm that handles accounts for a whole lot of household names. It came with a lot of responsibility, control and a 6-figure paycheck nearly double what I’d been making prior.
It’d be hard work that would test the business training I’d been longing to use for years.
But this was a huge wrench in my plans. I’d only just finished branding Business Casual; I’d put my heart and soul into that little cartoon character and everything it meant for me. And now, just as soon as I’d taken a risk and stepped out on my own, comfort came calling with a nuclear-powered megaphone.
So tell me, what kind of idiot would turn down a title and pay grade like that for the “work-a-day life” and “meagre income” of a freelance writer?
This kind of idiot.
After going through three rounds of interviews and receiving an offer, I ultimately chose not to take the job. This is no hippy love-in, but I realized after a few sleepless nights that success meant more than just a healthy bank account.
I was happier than I’d been in months. I was building something new. I had total control over whether or not I succeeded or failed. I had clients – and I still get giddy over the fact that they are MY clients. As in, they chose to work with me.
This was where I wanted to be.
And while I felt peace in my decision, the fire of uncertainty still burned bright. I printed off the job offer and pinned it to my bulletin board with a circle around the dollar figure I’d just walked away from.
This would be my reminder. Every morning, I’d look at it and remember exactly what I gave up to chase this idiotic dream of bashing a keyboard for profit.
It paid off.
I plan to share my strategy for success in another post, but so far, I have been affirmed many times over in my decision.
It’s been just about 150 days since I chose to leave my old job. 150 days working without pants in the comfort of my tiny little home office.
I’ve consistently earned 40% more than what I was making at my previous agency. And though I know work will always ebb and flow, last month I actually turned a profit higher than what my salary in the SEO director role would have been.
I celebrated by buying myself the cheapest dual monitor I could find and a keyboard that didn’t have things growing in it.
I’m not looking for pats on the back. This is not an exercise in self-congratulation or a chance to wave ambiguous income figures in people’s faces like I’m some kind of genius big shot.
Let’s be serious ladies and gentlemen, it’s been just 5 months. I have no misgivings about the fact that work could dry up or that something could go horribly wrong (like a sprained wrist). I’m still making all kinds of mistakes – but I’m growing through them.
But though it may sound bizarre coming from someone known for his cynicism, I wrote all this because I want other people to believe the same tired cliché that I had almost written off:
Do what you love, and the money will follow.
Then again – when you do what you love, the money might not matter so much anyway.