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.”

“Hmm… Ok.”

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.

27 Responses to “150 Days Without Pants: The Business Casual Story”

  1. great view to a brand. it’s admirable for someone to deny comfort in exchange for the unknown. im happy to know of business casual’s immediate success, yet i dont see reason for otherwise.

    i feel like wherever the business story takes you, you’ll see the good in the writing itself. keep dreaming and writing.

    • Joel says:

      Thanks buddy – I just hope this is all sustained. I’m planning for it to, but I also live in reality.
      And in truth, I sincerely hope you start seeing some returns on your side, friend. You are too talented and too kind a soul to lose your spark; I hope it lights some powder kegs.

  2. Saul says:

    Well done! Your writing has quite a unique style in the fact I think I can skim the content and get a picture of your story or read it in full if I want to read more. I was at a conference the other day and a speaker said “The most expensive copywriters are usually the best”. What are your thoughts on this? I think in the SEO/online content industry there is alot of people trying to rip you off and I have discovered good writers who write for less than others who produce tripe (IMO).

    • Joel says:

      Saul – Thank you.
      As for the comment, “The most expensive copywriters are the best” – yes, and no.

      Factually, those who are worth their salt and have the portfolios to prove it are going to charge a LOT more than the college kids and overseas workers are going to – as they well should. I would say that if you come across a copywriter with consistently strong work, they are worth every penny of that fee because their writing should actually make you money.

      But, it is a bit of a game. Most copywriters lack a business sense and operate in a constant state of fear. “Will I make rent? Will I get that next job?” – and so they don’t raise their rates because they don’t know their worth. There are certainly some diamonds in the rough out there who charge less than you might expect.

      In the end, the key to evaluating any writer is too look at their body of work before you ask about rates. If you love their work and can afford their rate, do so. The hunt for a bargain can leave you worse off, anyway.

  3. Saul says:

    Yes- I am feeling you on the “Will I make rent” issue.

    I have worked with some content providers and sent back article after article with the same old excuses thrown back “This writer is usually one of our most respected writers”. I think it’s vital to have a copywriter you know is going to deliver instead of your request being put into a pot for any writer to put their hand to it.

    I also think there is a massive gap in the market for a quality content provider who are filled with good writers but also allow agencies/SEOs to have conversations with the individuals.

    But that business can only be created by someone who possesses both an eye for content and an eye for business and like you say these people may be a rarity.

  4. Cam Secore says:

    If you wanna get really crazy maybe you could buy yourself a new mouse pad next month.

  5. Tony Dimmock says:

    Hats off to you Joel. Doing what you love is key and the stuff that’s in your basement will continue to pull you through, when times are hard.

    Like you, I turned down a decent role with a tidy pay-check. You know what? A day doesn’t go by when I thank my lucky starts for the opportunities that come my way because of my decision, which at the time bordered on the insane.

    Stay strong, remain focused and keep believing :)

  6. Emma says:

    Such an awesome story, Joel. Happy to hear things are going well. Keep it up and you may just be able to buy TWO waterproof couches.

    High five, friend.

  7. This reminds me a little when I left my job as an electronics engineer to join the SEO industry. Change is often a challenge and your story confirms following passions is the right thing to do. Congratulations, Joel, keep it up! :)

    • Joel says:

      Thank you, Giuseppe! I am reading your story right now, actually. Very interesting! I hope you are loving the decision you made.

  8. Joel,

    it was the best read of the month, seriously.

    Thanks for sharing your experience. Wish you good luck in further steps to happiness!

    BTW, how many hours a day do you work? Do you work on weekends?

    • Joel says:

      Thank you, Ksenia!

      As for how much I work – a lot. Like, a lot a lot. My first three months I turned in 12 hour days most days, taking maybe two days a week off (or at least part of those days). Now, I still work longer hours at times, but I’ve hit more of a rhythm and I’ve become better at allocating my time and avoiding distractions.

      I still work the odd weekend when I’m on a deadline.

      Thanks for reading!

  9. Jeff Sauer says:

    Great story Joel. I recently did the same thing – left the comfortable job for similar reasons to yours. It was not necessarily a secure financial move, but it’s hard to put a price on freedom. Best of luck to you moving forward. You are well positioned for the future.

    • Joel says:

      Thank you Jeff. Financially, this move to writing should have been suicide. I think the fact that I had a plan and a network coming into it has been invaluable – and the fact I have virtually no overhead. It’s been a serious ride, though – and even though income may have gone up, I’ve lost balance in some other areas of life (like fitness) that I’m learning how to take back. Appreciate your comment.

  10. Sean says:

    Congratulations man, it’s great to see that you’re thriving working for yourself :)

    Some people can’t adapt to working for themselves, particularly within the writing game. These are the people who complain about how little money you earn and how difficult it all is.

    You’re proving that if you’re smart and willing to work hard you can do really well. Hopefully we’ll get another recap after 6 months/a year.

    • Joel says:

      Cheers, Sean! It’s funny, but things started to change for me online after you picked up some of my stuff and let me write the antihero post. I attribute a lot of my network to you. And yes – there will be future recaps. Lots more stories to share.

      • Sean says:

        No worries man, funnily enough I think your anti-hero post may have helped me as well (not too much of course…) I think it’s the most read post on 0110 :)

        What’s the plan? Are you going to turn business casual into an agency eventually?

  11. Iain says:

    It’s great things have started so well for you. You write like you’re happy and I hope you stay happy for a long time.

    I like to believe that we make our own opportunities – those of us fortunate enough to be in a position to have options at least – and it’s always encouraging to read/hear about people doing that and making it work out well.

    All the best.

  12. Adam says:

    Working whilst not wearing pants. A true North American dream.

    Seriously though, props for taking the step into the infinite abyss. It’s all about the journey anyway, isn’t it?

  13. Christoph says:

    Joel, I really liked reading your story. Definitely motivating. I’ve been on the edge of doing the same kind of step, but never pulled the trigger. I think I really have to re-evaluate things a bit more. Congrats on your success. You deserve it and you are working hard for it.

  14. Gent says:

    As a non-native English speaker, I’ve got to sit down some day and study each word of yours that I can find online.

    Seriously man, I really admire your style.

    I really enjoyed the story and I wish you all the best.


  15. [...] Joel has published recently says a lot about him: he’s refused a double wage as an SEO to go freelance as a copyrighter. Having done something similar in my career, I can completely understand him, but it’s not [...]

Leave A Comment