How I landed My First Freelance Client

Image Credit: PIxabay

Image Credit: PIxabay

By Chris Gillespie, founder of Find A Way Media

An exercise in self-belief


On the very last day of July, 2015, our company's sales director slid into a glass-walled conference room and motioned for my boss to join him. Both glanced my way. I knew I was about to be fired. 

My gaze returned to my computer screen but the images swam. The overwork and lack of sleep had wrecked my nerves. I had made exactly zero sales this month and I felt the surreal sensation of floating. Was I really being let go?

At this startup it wasn't uncommon for teammates to return from lunch to find a coworker gone, save for their still-steaming cup of coffee. Honest to god I considered slipping out the back stairs but was anchored to my seat. I was mortified. I couldn’t run. Instead, I just started writing about it.

That article would become a blog post and that blog post, my new career, though I didn’t suspect it then. I was simply hungry to prove to anyone who cared to read that I knew a lot about my job, and had lots of other nice qualities thank you very much -- even if I couldn't close a deal. And if I'm being honest, I also wanted to be paid. The marketing team offered cash prizes for articles. So began my love affair with writing -- not with a bang, but with something much simpler.


Here's that very first article: How to Make People Fall In Love With Your Cold Call.

Do you keep the day job?


In the beginning, I was so flattered that our company would publish my articles on the blog that I didn’t aspire anything more. I got better at selling and when the threat of being fired lifted, it was hard to complain. But when things would go wrong, I'd start to think of writing as my backup plan.

On one Friday in particular, I purchased a box of cookies and steered my battered old Honda Civic to a prospect’s office. I waited in their lobby for two hours before they could no longer pretend to be busy and reluctantly signed the contract. Back at the office, my teammates applauded my aggression but inside, I was retching. I had to be doing something more meaningful than act like some software debt collector. I shuttered myself in a room and wrote, hard. And on that day, I started to plan.

My job was a golden handcuff.

People will always tell you not to quit your day job. I followed this advice for about six months and looking back, I highly recommend quitting. If you’re working full days, your best and brightest hours go to fulfilling someone else’s dream. Your passion project only gets the dregs. Working nights also conflicts with just about everything fun. When you have to decide between blowing off steam or grinding at home alone, the latter rarely wins.

My job was a golden handcuff. I never wrote for myself or tried to get published elsewhere. I talked about taking flight but really, I never did much more than stroll. My moonlighting was half-hearted.

The day I delivered the cookies, I finally got up the gumption to create profiles on the freelancing sites Upwork and Freelancer. I scrolled through an endless sea of miserable postings offering third-world pay. As an untested writer with zero reviews, I earned zero responses. 

After running out of messages, I didn’t touch the platform again for months.


When lightning strikes


I returned to Upwork in a panic in January of 2016. One week later, I’d be jobless. My firing hadn’t come, but my fiancée’s had. The startup she worked for had flamed-out after the CEO overspent on flashy events. That night we enjoyed a nice dinner out and, arms entwined, agreed to travel Europe. I was elated. I was terrified. I needed a client.

If there was one thing I understood from my sales career, it was how to begin selling. I knew there was a market for my writing because I frequently spoke with marketers who opined not having enough written content. I also knew that our own marketing team thought about buying written content in blocks of 10. As in, how many multiples of $10,000 does something cost? This, I could already tell, was a world apart from the tens of dollars most freelancers accepted and I was certain I could fairly demand much more. But as the pressure mounted and my final day approached, I lost my nerve. 

Looking back, my rate was a reflection of my self-confidence.

I accepted my first client – someone I reached out to on Upwork – for $25 per article. After edits and revisions, it was a fraction of the minimum wage. 


Afraid of hearing ‘No’ from clients? Read this piece I wrote at the time about dealing with rejection.


Looking back, my rate was a reflection of my self-confidence. I didn’t feel I was worth more. I also thought that I needed to write for small, obscure companies where I could afford to make mistakes. I didn’t even feel comfortable referring to myself as a writer. It was too much pressure. I didn’t want people to confuse me with an author or ask about my upcoming novel.

My first client turned out to be a great guy. He coached me, referred me more business, and eventually increased our rate and doubled his spend. I owe a lot of that early success to his honest feedback. And once I had reviews on the platform, I started to win more bids.

I found other clients through Upwork, some of whom were rubbish and some of whom were nice people. I was soon eking out close to $1,000 per month while my fiancée and I wandered from Copenhagen to Mallorca. Freed from rent and utilities, the trip actually saved us money and relieved some of the burden of being officially jobless.


upwork client

This is the post I replied to that landed me that first client.


And here’s what I started writing for them: 4 Marketing Psychology Tips so Obvious You Forgot to Use Them


At this point, I wasn’t as much nervous as I was determined. I had a safety net of sales commission and company stock. In a pinch, I could dig into my 401k. But there was no backup plan. Once it was gone, it was gone, and I felt it. I was finally hungry.

I’d write furiously at night, building a client base and my confidence. I was stung by feedback. I was rejected. I acceded to outrageous timelines. I hardened. Clients called my writing “too cute,” or “not quite it.” Sometimes, they didn’t respond and didn’t pay. But I started to believe that this was something I could do. By the time we settled in New York, I was ready to come back in from the proverbial writing wilderness and find some real clients. 



Money, yes. But mostly, self-belief


After three months of full-time writing, I graduated from Upwork. Each time a new client would agree to my rate, I’d realize I could ask for more and I’d double it for the next one. I started seeking outside feedback. I pursued what I’ll call ‘real’ companies and I poured everything I knew about outbound sales into building a book of clients who could pay real money. When I landed my first true retainer with a venture-funded startup, I knew I was there.

Looking back, it seems clear that I could have done this all faster. I put myself through a lot by leaping out into the writing wilderness. I could have quit my job earlier. I could have started by approaching better companies and charging more. I could have been more aggressive. And at the same time, I couldn’t have. I didn’t ask for more because I didn’t believe I was worth more. The real transformation happened inside. 

Now, I call myself a writer. Perhaps someone else could have done this more effectively. But for me, I think it happened on exactly the timeline it needed to happen. Landing my first client was partly about the money, but mostly, it was about me.


Want tips for finding clients? Read The Big Book of Freelancer Sales Strategy.