I know I was lucky to land the first freelance job I ever applied for. It was a straightforward transcribing job for a New York Times writer based in Melbourne, Australia. Naively, I thought that a one-hour audio file would take me about two hours to transcribe.
Man, was I wrong. I think I spent four or five hours earning my first freelance paycheck, even with my voice-to-text software assisting. Not a great start.
But I learned two critical things:
My very next move was to hit up the University of Google for help. Searching ‘How to make money on Upwork’ brought me to several people claiming to have the key. One of them offered a course that would set me back $47, which was tempting if for no other reason than the price. But the info appeared to be a couple of years old.
Another one was by some guy named Danny, who claimed to have made over $100K in a year, but his course was going to cost me several times more than the other one.
One thing was obvious, though. I was never going to make $100K a year as a transcriber, not even in ten years, no matter how many courses I did.
Searching Upwork a couple of days later, I came across a job for a virtual assistant, posted by another guy named Danny. He was looking for help posting blogs to his website, which he’d also listed in the job post. Clicking through, I realized it was the same guy who ran the course on how to make $100K on Upwork.
On a very well-written and persuasive landing page, he urged me to sign up for his five free hacks on how to crack the Upwork market. I decided it was just meant to be. I handed over my email address for the keys to the Upwork kingdom.
As promised, Danny sent me several, okay five, emails over the next few days, each one revealing a little bit more of the puzzle. And it was stuff that I could use straight away. He even sent me a personal welcome email, asking why I’d signed up for the free hacks. Surprised and impressed that he was a real person who actually wrote his own emails, I replied, saying I was unconvinced that his course was going to help me, but I hoped that he might consider me for his assistant position.
I’d been working a day job as an executive assistant for over 15 years. I didn’t really see myself as a copywriter. A writer, yes, I’d been doing that all my life. But copy writing, and the thought of getting paid over $100 an hour to do it, scared the crap out of me.
Danny promised me that whether or not I took up copywriting, and regardless of whether he chose me for the job (he didn’t L), he would help me learn something of value. And a little voice in the back of my mind whispered that I should believe him.
So, after lots more research (read Internet stalking) into whether this guy was for real, and with more than a little hand wringing and a healthy dose of what the hell, I signed up for his course.
Over the next 12 hours I did nothing else but listen to Danny’s voice leading me through a series of videos. Then I sent him this email:
“Danny, I put off joining your course because I thought it might be too copy writing oriented for me - but I was wrong! I ploughed through half the course last night...couldn't put the laptop away. My eyes are so red this morning and I just didn't want to come to work. I still have a full-time job as EA to a demanding CEO, hopefully not for much longer. THANKS for your brilliance.”
Despite Danny’s continued encouragement to try my hand at writing, since he somehow knew that was what I wanted to do, I still resisted. I kept applying to simple admin jobs and more transcriptions. Unfortunately, I kept winning them. I say, unfortunately, because my fairly effortless success at winning these smaller jobs kept me from having to face my fears and apply for a writing gig.
Then the day came – I finally landed a freelance writing job, doing up a blog post from a podcast interview. It was exhilarating. But when I thought about actually doing the writing, I panicked. I went over and over and over my work, making sure I’d done the best I possibly could. I attached it to the email and hit send. Then I went to pieces because I didn’t hear from them for ages. Danny reassured me that that was a good thing. Clients reject work they don’t like relatively quickly.
I learned something very important:
The fear of success is more debilitating than the fear of failure.
I found my mojo and started applying for writing jobs. And when I won them, I only panicked a little bit. But my confidence grew and pretty soon I started getting invites to jobs without applying. The Hidden Upwork Economy that I’d thought I’d never find finally kicked in.
I was still working full time as an executive assistant. I was really working two full time jobs, because after I got home from my day job, I immediately went to work on my freelance jobs. Often, okay mostly, that meant working till 1 or 2 a.m. just to keep afloat. For months, I went to my day job in total resentment mode with road map eyes, just wanting to be back home at my keyboard.
I actually got to the point where I couldn’t take on any more freelance work because of the day job. I knew I could get more jobs, and more lucrative jobs, if I just had more time!
Then life stepped in and threw the curve ball that knocked everything else into place – my brother disappeared. It might sound like a strange thing to be a good omen, but life’s like that. Doors close, doors open, as they say. And it was the impetus I’d been needing to hurl me out of my comfort zone and into the freelance abyss.
I suddenly needed to be free of the rat race, to be able to work anywhere, at any time, so that I could deal with all the other issues that came with having a missing person in the family.
The day I handed my boss my resignation, one of my co-workers looked me in the eye and made a perceptive remark that really hit home: these kinds of things only happen to those who can cope with them.
I knew I could do it. I told myself I could do it. I believed I could do it. So, I did it.
I took a deep breath…and leapt into the abyss. And you know what? Nothing bad happened. The world didn’t end. In fact, just the opposite.
Since then I’ve had more (Up)work than I’ve needed. I’ve been able to pick and choose the freelance jobs I want. And I’ve got over 200 connects left in the kitty because I’ve rarely had to apply for jobs.
One thing I’ve learned on the SSFU course is not to take too much notice of the client’s proposed budget. Sometimes they’re not sure themselves. The client in the screenshot below invited me to a job for a 2500-word article for $50. I submitted my proposal as usual, following all of Danny’s proposal criteria, but changed the bid to $250. Without even questioning my price, the client hired me, literally within 15 minutes.
I currently have five permanent, high-quality clients who pay me an average of $100 an hour to do what I love – write. Write, write and write. Blog posts, landing pages, web content, business articles. And when I want more work, I just arc up Danny’s videos, review the proposal guide, and win more jobs. It really works. It’s like opening the freelance vault and withdrawing what I need. But it never ceases to make me smile. And thank Danny – again.
I no longer do freelance transcribing, except for the journo in Melbourne, of course. I will always do her transcribing when she needs it because I owe her a great deal. She made me think it might be possible. Danny showed me how to make it happen. I’m forever grateful to them both.
I’ve even found the time to complete my book, a travel memoir spanning over ten years of living, working and traveling the world. Check it out!
If you’re hesitating about whether or not Danny’s Secrets of a Six-Figure Upworker course is for you or not, think about this:
Whether you think you can or you think you can’t – you’re right. Henry Ford
If you enjoyed this post, please leave a comment below and tell me about your own jump into a freelance lifestyle.