Case Study: How Jenn Escaped The 9-5 and Started Working For Herself

By: Jennifer de la Chevotiere

How do you feel about your job?

If you feel trapped, unfulfilled, bored, or frustrated, I get you. If there is a desperation swelling into your chest, screaming that you just have to get out, trust me, I get you.

I spent a lot of time stuck in dead-end jobs that I hated, unable to see a way out.

And even though I’ve worked since I was 15 (I’m 26 now), I never really felt like my career started until I began working for myself.

Currently, I’m a full-time freelance copywriter, and I absolutely love my job.

But it’s been a long journey to get to this point. I mean, if you told me about a year and a half ago what my life would look like today, I would’ve laughed in your face!

Today, I tell anyone who will listen that they can jump into the freelance game with the right attitude, a bit of research, and some hard work.

I hope that by sharing my story from beginning to end, I can help inspire a few people to get started.

The Road to My Breaking Point

Like a lot of people, I started my work life in retail.

In fact, I spent about 10 years in retail.

At 15 I started at my local grocery store’s deli counter. I came home everyday smelling like meat, but on the bright side, my dog LOVED licking my shoes.

Then, I got my first taste of working for a large corporate chain posing itself as a local boating store.

This place was a masterclass in how layers of red tape can destroy the customer experience.

After years of putting up with improvements that were promised and never delivered, I had earned a big fancy degree and made the mistake of thinking I could move to a larger city and easily get a job.

Too bad thousands of grads all thought the same thing.

I spent months perfecting my resume and my LinkedIn. I sent out hundreds of applications. I got friends and family to double and triple check everything I sent out. But the phone wouldn’t ring.

So, I went with the comfortable option: going back to school and getting another retail job for $11.75 an hour. Some readers may think that’s big money for retail, but:

  1. I was helping manage the store I left in my hometown for $13.50.
  2. I live in Canada where that was minimum wage at the time.

This was the worst job yet. I’ll spare you all the gory details, but I worked in a bad area of town, and a customer once threw a laptop that narrowly missed my head.

FINALLY, I got what I thought was my big break. A research company wanted to hire me full-time, salary. I could use my degree and make a difference!

My family started to tell me that having a 9 to 5 job isn’t all it’s cracked up to be. But, after years of struggling in part-time jobs, of not making more than $10,000 in any given year, I could not have been more happy to have the stability.

That feeling lasted about three months.

The job had a lot of problems, not the least of which was the fact that I had a desk in a literal closet, which made it very difficult to get to know my coworkers. It was boring and lonely, and I simply couldn’t stand it.

As someone who has been through the ringer, who knows what it is to have my income and 40 hours of my week at the mercy of someone else, I get the mix of emotions that goes along with thinking about making a change.

But having made the leap, I can safely say it’s worth it!

What I learned: before I start telling you about how things changed, let me give you the takeaways from this era of my life.

During this time, I had a lot of prospective employees tell me that my time in retail didn’t count for anything. They wanted to see “professional experience.”

Don’t ever accept that.

If you have the right attitude, you can learn from any position you’re in, no matter how much others look down on it.

I learned leadership, empathy, communication, time-management, and teamwork from my years in retail. And I use those skills every day now.

That’s not nothing.

The Turning Point

When I say my desk job was boring, I mean I got about 3 hours of work in the average 40 hour work week.

I didn’t want to waste the rest of my time, so I learned as much as I could about business and coding HTML (by the way, I highly recommend Codecademy if you want to learn to code!).

I spent hours reading inspirational stories about people who had been unhappy, and decided to start their own business.

The problem was that most of these people already had an Ivy League education, major business connections, or a once in a lifetime idea.

Didn’t exactly feel achievable from my lofty position in the closet…

But one day, I read a story about a guy who had no fancy degree, no special skills or connections, and no brilliant ideas. What he had was the frustration of a crappy job and the desire to gain back some control in his life.

He got online and taught himself about copywriting. He became a freelancer, pushed through the setbacks, and made a damn good living doing it.

Simple, achievable!

Now, when I read this story, I still had my doubts about freelancing. I’ve been told my whole life that it’s risky, that it’s hard to make good money, and that I shouldn’t get my hopes up with something like that.

And even though the story stuck under my skin and wouldn’t let go, I sat on the information for months before making a move.

After all, I’d been on freelancing websites before and witnessed all of the $5 offers for 10 hours of work. And I didn’t have any experience, so I’d be making pennies a day, right?

If people spent years trying to convince people to pay them a decent wage for their time, what hope would someone like me have? This story was definitely just a fluke.

But I did start spending more of my time learning about copywriting and marketing from sites like Copyblogger and Hubspot, and by reading books like Contagious and Wired for Story.

What I learned: During this time in my life, I learned how important it is to find what you can control when it feels like everything is decided for you. Even though I wasn’t ready to start freelancing, I didn’t just give in to the boredom.

I learned as many new skills as I could to work toward something better.

Fear, the Wicked Ruler

As we round into the third act of this story, you’re probably thinking a bit deeper about your job and all the little things that make you unhappy.

Or maybe, even if you like your job, you know in your bones that it’s time to move on and build something for yourself.

Either way, your brain is probably starting to make simultaneous excuses for every thought that says: “maybe I can become a freelancer too.”

That my friend, is fear.

The reason it took me months to make a move was that I had a crippling fear of where it would go.

What if no one takes me seriously?

What if people think I’m a joke when I have no experience?

What if someone actually hires me. then hates my work?

The thing about fear is that it feels like the truth.

My big fancy degree is in Psychology, so I can tell you with confidence that it feels this way because our fear response developed to deal with predators.

It’s not meant for things like sending proposals out to clients.

If you take one thing away from this article, let it be that your fear is not real. It’s not the crystal ball showing you your dismal future. It’s not the friend protecting you. It’s the thing standing in your way.  

And don’t get me wrong. The feeling never goes away.

I am still afraid of every proposal I send out and every first draft of work I send to my clients. Hell, this is a commissioned piece of work and I’m terrified to send it to my client in case he hates it.

But the point is, I’m going to send it anyway. And I’m going to keep working and learning from my mistakes, no matter how loud the fear in my brain is yelling at me to stop.

What I learned: You need to trample your fear like it’s nothing, because it’s not telling you anything of value. If you want to learn how to freelance, there are practical steps you can take. It’s not a fluke or pipe dream.

The False Start and the Start of Something Big

After spending weeks toying with the idea of freelancing, obsessing really, I decided I wasn’t going to let fear stop me, I told myself I would write a proposal in Upwork (a freelancing website) no matter what.

I spent hours crafting the perfect proposal. I even wrote a short sample piece similar to what was being asked for, to show my skills.

(by the way, DO THIS if you don’t have a portfolio, or you don’t have anything similar enough to show. This is some excellent advice being snuck into this story!)

But as the seconds ticked away, I started to lose my nerve. I started to think how impractical it was that it was taking me so long to write a proposal. I was plagued by the thought that I had no business seeming so confident in essentially untested abilities.

Again, I let fear win and it took me another few months to send out my next profile.

In this time, I got miserable. I could barely get out of bed in the morning, and I came home grumpy every day.

I started to look for new jobs, but I couldn’t help thinking that I would get out of the frying pan and into the fire. I mean, to this point I had been frustrated in every job I’d ever had.

I knew that I wasn’t the type of person who could fall in line and just take orders. And it was starting to eat at me.

After a few more dead end applications and one really bad interview where the guy looked like he was about to fall asleep listening to me, I decided that enough was enough.

I wasn’t going to let anyone control my future anymore, I was going to get freelancing jobs and make it a career, damn it!

I crafted every aspect of my Upwork profile to be more appealing, and I started sending out proposals like mad.

It took me awhile to get someone to bite, and even when they did, they disappeared sometimes. But I didn’t let it stop me, I kept pushing.

I got better at sending out proposals, and after a bit of practice, I could send them out in a matter of minutes.

Finally, I met Greg. And Greg was floored by my proposal, so he decided to give me a shot the second we interviewed on Skype.

His faith in me made me feel more confident, and I happily accepted the job.

He was an amazing client, and he absolutely loved my work. If you’re curious, you can read the work I did for him here.

It turns out that the fear that was holding me back was just stopping me from an amazing experience.

After that first job, I was hooked.

And I haven’t stopped since.

About 8 months ago, I was able to quit the job that was making me miserable and work from anywhere with a wifi connection.  

These days, I don’t have to worry about sending out proposals often. I usually get invitations through Upwork at least a few times a week.

If you’ve never used Upwork, clients can search for freelancer profiles with skills that match their needs.

If they find you, they can invite you to apply for their job, instead of you having to do the searching. It’s magical!

I’m also lucky enough to have a group of amazing clients who only want to work with me. So any small issues I’ve experienced during this change have been more than worth it.

What I learned: Trust your instincts. If your gut says that you’ll only be happy working for yourself, why bother putting yourself through misery?

My family was ADAMANT that it was too risky, that everyone has to put up with things they don’t like, and I should focus on being thankful that I actually got a job. It got into my head and it slowed me down.  

4 of My Best Actionable Tips To Get Started NOW

Here are a few more tips that will show you how to get started as a freelancer:


  • Don’t expect a traditional cover letter to work as a freelancing proposal.


I made this mistake when I started. You want to be a lot more friendly and conversational than you’re used to being.

It’s going to feel wrong at first, but people are just people at the end of the day, and they have to like you before they hire you.

If they include a link to some of their work, start by complimenting something they’ve done well, then offer some suggestions for how they can improve (without being too pushy).

This shows you’re already thinking critically about their work and that you have the skills to work on the project.


  • Not everyone is looking for the same thing.


You need to become a communication chameleon! The way one client may like to speak with you may be a complete turnoff for another client. Take note of how your prospective client writes their job listing.

Are they short and to the point? Are they conversational with flowery language? Do they use a ton of smiley faces?

Take note and mimic their tone. I can’t tell you how many jobs this has helped me get!


  • Do your research!


You will never thank yourself for cutting corners!

If you know what company the prospective client works for, read about them. If you aren’t 100% comfortable with the type of project you’ve been given, make some time to learn the the best practices.

And for the love of god, if you’re writing something for your client, PROOFREAD.

You’re client is going to notice if something is sloppy, or if you’re heart isn’t  in it. Don’t rush, take your time, and be humble. The learning never stops and you can always do things better.


  • The time will never be right


There is no ‘right time’ to get started. There will always be obstacles in your way, and it’s up to you to find ways to remove them.

Easy money doesn’t exist, simple doesn’t exist, freelancing jobs handed to you on a silver platter don’t exist.

Waiting for the perfect time just means more time you spend in misery daydreaming of how your life could be better.

Start now, because it’s going to take some time to get in position that feel comfortable.

You’re going to have to roll up your sleeves and work for it, but it’s going to feel damn good in the end.

Now I want to hear about your experiences! Are you still stuck in the fear stage? Have you started sending out proposals? Gotten any bites? I’d love to hear about it!

Leave a comment below with your story!


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