How I Earned $10,000 From 1 Awesome Grand Prize Blog
The award-winning blog post that earned me $10,000, changed my life, and helped me start a new career making money on the Internet
Have you ever had a single blog post change your life? It happened to me.
It was 2009. My wife and I had a 1-year-old baby at home, and another on the way. I was the sole breadwinner for our small-but-growing family. At the time, I was working at a full-time day job at a big bank, doing technical writing for regulatory compliance documentation.
Unfortunately, at a moment when families need stability, health insurance, and a steady paycheck more than ever, I had reached an uncomfortable, distressing breaking point in my career. The people at my job were kind and the corporate benefits were generous, but the cubicle lifestyle had worn out its welcome. I was bored. The work felt highly repetitive and mostly meaningless; my old job has probably been replaced by AI by now. Worse than that, I was feeling desperate and trapped in my cubicle. I was having panic attacks within the gray, windowless walls.
I wish I could say that 2009 was a simpler, more innocent time, but anyone who’s seen The Big Short knows that wasn’t true. This was the era of the Global Financial Crisis and the Great Recession. Millions of Americans were losing their jobs and homes and retirement savings. The stock market was plummeting, big-name banks were failing. It seemed like Capitalism itself was collapsing. But my problems at the time were smaller and more personal. I wasn’t focused on the GFC and the Great Recession; my job was never in jeopardy because of it, and the bank where I worked survived and prospered despite the GFC. Instead, I was worried about overdrawing our checking account and putting food on the table.
Ever since our baby was born and I became a sole breadwinner, my day job paycheck hadn’t stretched far enough to comfortably pay our bills. And the idea of a promotion or pay raise was out of the question (since, uh, the entire financial industry was collapsing). Even though I was a privileged white guy with a fancy college degree and some impressive-looking work experience on my resume, I still felt like a failure. I was 30 years old with three beloved mouths to feed, and I was burning out. I felt like I had no viable future ahead of me. Everywhere around me I saw nothing but dread and gloom and unaffordable expenses stretching to the far horizon.
I needed to find a new way to make more money. There had to be a better way. All I wanted was to be able to work from home and be with our children, and the corporate cubicle world of 2009 would never let me.
That’s when I found out about Elance (now Upwork). I randomly read in a Newsweek article about how hip young people in New York City were making money as freelancers and gig workers, and how Elance (Upwork) was a site where they found projects. This was what I needed! After work, I went home and set up an Elance (Upwork) profile and immediately started using my nights and weekends to bid on freelance writing projects.
It took a few weeks, but finally I got my first Elance client. It was a corporate consultant from Australia (the 15-hour time zone difference meant that she was online during “business hours” at the same time I was moonlighting). I got paid $200 to help ghostwrite corporate training materials about Diversity in the Workplace.
The project was fun, the client was grateful, and suddenly I had $180 (the project fee minus Elance’s commission and transaction costs) in my bank account.
This moment changed everything for me. It blew my mind that I had just gotten money from the Internet. And all by doing a fun project that didn’t even feel like “work,” that took me a few hours, that paid me more than I would’ve made from sitting for 8 hours in a gray windowless fabric-padded box.
A few more months went by and I got more freelance work on Elance (Upwork). It became my new fun hobby. I was grateful for every project, every paycheck. In December 2009, Elance announced that they were having a contest: $10,000 first prize for freelancers who could creatively show how Elance and the “New Way to Work” of online freelancing had changed their lives.
I was galvanized. I knew instantly what I had to do. The idea came to me like the clouds parting, like golden letters appearing in the sky. I sat down at my laptop and cranked out a blog post, called Cubicles are the Phone Booths of the Future, that was a passionate cry from the heart, a full-throated defense of remote work and working from home. All of my hours of my twenties that I spent confined in windowless rooms doing Office Stuff had led up to this.
And then? I won! I won the Grand Prize. $10,000. But then: my day job found out about my side hustle, and I almost got fired. But it all worked out in the end! I rallied under pressure, improved my day job performance and got back in my boss’s good graces, and eventually resigned from my corporate job on good terms. And today, after more than 15 years of working from home, making a living on the Internet as a freelance writer, I’m glad I did what I did. It couldn’t have happened any other way.
I want to share the original blog post from December 2009. This article took me about 45 minutes to write, and I got paid $10,000 for it. That’s a pretty good hourly billable rate!
Cubicles are the Phone Booths of the Future
December 1, 2009
Note: This post won the Grand Prize in the Elance “New Way to Work” contest.
I’ve hated almost every job I’ve ever had.
OK, “hate” is too strong of a word.
Let me put it this way: I have often felt deep frustrations and resentments toward every job I’ve ever had.
I haven’t hated the work itself or the people that I’ve worked with, or even the organizations that I’ve worked for. I’ve done really good work and had some great times with some really great people.
But what I’ve hated are the limitations and confinements and pointless restrictions of the “job” itself.
I don’t like having to work “standard hours.” I don’t like having to show up at 9 a.m. (or earlier) and work the same amount of time every day. I don’t like never getting to see daylight (my office has no windows). I don’t like the enforced idleness – I hate those days where even if there’s not enough work to do, you still have to sit there for three more hours, just to “put in your time” and keep up appearances. I don’t like having to get all my groceries and run all my errands at night and on weekends – what if I want to go to the store at 10 a.m. on a Tuesday? What if I want to play with my child in the park on Thursday at 3 p.m.? What if I want to go jogging on Wednesday at 1 p.m.? I can’t do any of that when I have a “job.”
Most of all, I hate having a cubicle.
Think about it. Do you know of anyone who truly likes their cubicle? Do you like your cubicle? If you had a choice, would you ever in a million years choose to work in a cubicle? Isn’t there something fundamentally pathetic about the way so many of us spend the majority of our waking hours, hunched inside these fabric-padded boxes, peering at computer screens, eating our sad little microwaved lunches off our desks?
This is America, right? “Land of the free, home of the brave” – but this “old” way of working in a cubicle – the isolation, the sensory deprivation, the bad lighting, the walling-off-of-oneself from the wider world – doesn’t feel very “free” to me, or very brave.
Fortunately, I believe that we are on the cusp of something better – much better – than life in a cubicle.
With Elance, I’ve discovered the start of a new way of work – and a better way of life.
Cubicles are the phone booths of the future.
Someday, people are going to look back at cubicles with the same sense of disbelief that today’s kids have when they look at phone booths.
When was the last time you used a phone booth? (When was the last time you even saw a phone booth?)
It sounds absurd, right? Who needs a phone booth in this day and age, when everyone carries phones in their pockets? Imagine, having to sit in one specific spot and use one specific phone just to make a call!
Well, someday – probably sooner than most of us expect – people will look at cubicles the same way.
(“Wow,” future visitors to the Cubicle Museum will say, “you had to sit in that thing all day, just to earn a living? You couldn’t go work at the park in the middle of the day, or sit with your laptop by a sunny window at the library, or work from your home office while your children are sleeping?”)
It’s true that there are some jobs where you need to be on-site and work set hours. If you’re a 911 dispatcher, you definitely need to be on call at set hours each day. If you’re an attorney or consultant who works on a billable hour basis, you need to put in a set amount of time to demonstrate your productivity (although the billable hour system is under pressure, as clients look to rein in costs). If you’re a retail store manager or a restaurateur, you need to be where your customers are. If you’re a waiter in a restaurant, serving food, or if you’re a nurse in a hospital helping patients, you need to be “there” in order to do your job.
But for most of us who sit in cubicles – those of us who are “knowledge workers,” who work with information and numbers and words and ideas – there is no “there” there anymore.
You’ve heard of this thing called the Internet, right? You’ve seen some of the smart phones that people are carrying around?
Questions for managers everywhere:
Why is it so important to you to have your people sitting in their cubicles for an arbitrary length of time each day? Why is 8 hours so important? Why not 7.569 hours? Why not 3 hours? Who cares, as long as the work gets done?
If the only way you have to measure your people’s productivity is the amount of hours they spend at work, shouldn’t you find some better metrics? (This is 2009 – we have the Internet – everything is measurable now. We are all effectively “on commission.”)
If the only way you can be sure that your people are working is to force them to sit 10 feet away from you in a cubicle all day, why did you hire them in the first place? (If you’re hiring real professionals, they shouldn’t require such close supervision – don’t you trust your people? And if not, fire them and hire someone better – there’s plenty of great talent in the labor market right now.)
Now more than ever, it’s possible to be available – and highly productive, and totally engaged – while still having the freedom and flexibility to choose when and where and how we work.
With the New Way of Work on Elance, we can work for clients worldwide, and we can do the work from anywhere. Who needs a cubicle?
Elance has changed my life.
Ever since I started my freelance writing business on Elance, I’ve worked with clients in Australia, Tokyo, England, Canada and the Kingdom of Jordan. (As well as all corners of the U.S. – from Seattle to Cleveland to Orlando to Los Angeles.)
I hold conference calls via Skype – for free – with clients whose time zone is 15 hours ahead of mine.
I send draft documents to the client via e-mail before I go to bed at midnight, and I get feedback from the client when I wake up the next morning.
I make much more money (on an hourly basis) working for myself, from home, than I’ve ever made working in a cubicle for someone else. I can make more money in two or three hours than I make sitting in a cubicle for eight hours.
Best of all, I love the work. I should have started doing this five years ago. The work is fun, it’s creative, it’s full of variety and new challenges, and it’s for real customers who are grateful for the help.
Most big companies aren’t ready for the new way of work. (Best Buy is one exception – they’ve implemented a “Results Only Work Environment” at their corporate headquarters which allows employees to basically come and go as they please, as long as the work gets done.) But smaller companies, sole proprietors, and even some innovative larger organizations are going to realize some great benefits from hiring skilled professionals on a flexible, project-by-project basis.
It’s easier than ever before to use sites like Elance to find qualified, vetted, reliable professionals to help on almost any project. You can quickly and easily put a project out for bid and mobilize a talented team from all over the world – and it doesn’t matter that you aren’t all sitting in the same row of cubicles together.
Of course, not everyone wants to be self-employed. There are still going to be “cubicle jobs” for people who want the more traditional idea of job security, or who love working for a particular company. There are still going to be jobs that require a kind of group synergy that only results when everyone is on-site together, or that require a level of confidentiality that is hard to achieve via e-mail alone.
But for those of us with a certain kind of skills, energy and ambition – this is a new day, and the sky’s the limit. We can work for anyone, anywhere, all over the world. It doesn’t matter where you live – all that matters is your skills, your hustle, and your demonstrated reputation for delivering results.
Thank you, Elance for introducing me to the new way of work. I think we’re on to something big.
####
Looking back on this essay now, from 2025, in some places it sounds a little snarky and arrogant and over-confident. I don’t mean to sound that way. I was just young and excited and impatient. I had discovered a pot of gold on my kitchen table, and I wanted to share it with the world.
The past few years have seen the rise and fall of remote work and Work From Anywhere, as more corporate employers have required their people to go back to the office. I was probably naive to think that “everyone will work from home” in the future.
And yet? This article still encapsulates some of my best, most hopeful thinking about what work can be, how people can relate to their work at its best. Online freelancing has been a dream come true for me and my family. We’ve gotten to be part-time digital nomads, traveling the world: Tokyo, London, Berlin, Paris, Madrid, Glasgow, Montréal. I’ve gotten to spend lots and lots of time watching my kids grow up, picking them up after school, going to their soccer games, being around for lots of lazy weekday afternoons and precious everyday moments that I never would’ve seen if I’d been stuck in a cubicle. And I’ve been able to grow my income, and earn a much better living than I could’ve had in the corporate world, while still having fun and enjoying a flexible schedule.
Our dreams have come true. It all started with this one blog post. Everything changed for the better, because I sat down at my laptop and started talking to the Internet.
I still believe in the Internet. My career and my life wouldn’t be possible without the Internet. Everyone’s tired of social media spam and AI slop. We need the Internet to get back to basics — back to the authentic interpersonal connections and shared humanity that made the Internet feel so exciting in the first place. In my own small way, my career as a freelance writer has been dedicated to trying to make the Internet a little better, a little smarter, a little more fun.
That’s what I’m trying to do now, with my new website, FunMoneyDad.com. I want people to have more fun, make more money, feel better about their money and life. I believe talking about money can be fun AND responsible. We can be prudent about investing for the future AND have fun today. Over the years in my career, it hasn’t always happened in a straight upward line, but I’ve managed to make money AND have fun along the way. I wish the same for everyone.