Escaping the 9 to 5: How I Did It

Escaping the 9 to 5 by Trying Everything

(Listen to this post ⬆️)

I dreamed of escaping the 9 to 5 for 11 years before it finally happened. 

I believe if you dream something long enough (and you work hard enough), your dreams can come true. 

If you believe the same, I want to tell you EXACTLY how I escaped the 9 to 5 — so you can escape too!

Below is my journey broken down by year. It was a long one but read the entire thing through. You'll learn from my mistakes and get an idea of what you need to do to strike out on your own.

Escaping the 9 to 5 by Trying Everything (2011 – 2015)

Escaping the 9 to 5 by Trying Everything

The first step to leaving your 9 to 5 job is figuring out what you’ll do OUTSIDE of your 9 to 5. 

This isn’t always easy. 

From 2011 to 2015, I juggled a million different things I wanted to do. In fact, I started several side hustles, including:

✅ Blogging

✅ Freelance writing

✅ Selling info products

✅ Running a “business freebies” newsletter (with affiliate links)

✅ Virtual assistance

✅ Freelance proofreading

I couldn’t for the life of me decide what I wanted to do. 

I just knew I wanted to be the boss

I didn’t want a salary cap. And I also wanted to do something I enjoyed that didn’t zap the life out of me.

This might be the reason you want to escape the 9 to 5 too! 

But because I juggled so many different things and ideas…it took me 11 years to finally strike out on my own and leave the 9 to 5 life behind. 

⚠️ Heads up: it WON’T take you this long IF you pick something and stick with it. 

If I had gone all-in on ONE thing since 2011, I probably would have escaped the 9 to 5 a lot earlier.

And if you go ALL-IN on *one* thing for a few years, you’ll probably end up leaving your 9 to 5 a lot faster than I did! 

But enough about the past.

Let’s fast forward to 2015 when I finally found the thing that helped me escape the 9 to 5 and become a full-time freelancer (with a digital course business) in 2022.

Deciding on a Freelance Service to Offer (2015)

Escaping the 9 to 5 with a Freelance Service

I’ve had multiple side hustles over the years because I'm multi-passionate. (Can you relate?)

I like blogging, digital marketing, creating info products, affiliate marketing, and email marketing. 

There’s just so much that I enjoy doing online. 

But by the end of 2015 (after struggling to find my perfect ‘thing' since 2011), I realized that blogging, creating info products, and earning small bits of affiliate income wasn’t bringing me enough money fast enough to leave my job.

I didn’t realize it at the time, but performing a service for people was actually my golden ticket out of the 9 to 5, because it came with a faster (and higher) payday.

But I figured this out by accident.

At the end of 2015, I was doing research for my “business freebies” newsletter, and I stumbled upon an opportunity to help a woman from a Facebook group.

She needed help setting up a lead magnet on her website. And hey, I knew how to do that with all of my years as a blogger!  

And it turned out, she was willing to pay me to help her set up her lead magnet. 

At first, I was shocked.

Someone wanted to pay me to do something outside of my full-time job? Mind-blowing. I thought, hey, maybe there's something to this!

So the woman sent me about $65 to help her add a lead magnet to her blog. 

At the time, this was the most money I had ever made outside of my full-time job. 

I couldn’t believe I had finally earned more than a few dollars outside of work!

This was when a light bulb went off in my head. I thought: Wait a minute, I could help people with their blogs for side income!

At that moment, I decided to take my years of experience blogging to become a virtual assistant for coaches and entrepreneurs who needed help. 

At the end of 2015, THIS was going to be my way of escaping the 9 to 5. 

Going All-In as a Virtual Assistant to Escape the 9 to 5 (2016)

Become a Virtual Assistant to Escape the 9 to 5

Starting in 2016, I put everything I had into becoming a virtual assistant (VA) to leave my full-time job. 

I enrolled in programs that taught me how to price my virtual assistant services and decide what those services should be. 

I also built a basic website on WordPress listing my services and qualifications. 

And I applied like crazy for virtual assistant jobs on job sites like Hire My Mom and FlexJobs

Then, after about a month of applying like crazy, I landed my first VA gig as an editor for a spirituality coach. I was completely beside myself with joy — my very first client! 

It wasn't exactly blogging help, but I was excited none the less.

Then, over the next 3-4 months, after applying like crazy, I eventually landed enough VA gigs in May of 2016 to add about $1500 to my monthly income. 

I couldn’t believe it — I was about halfway to making enough monthly income to leave my job!

But the problem was…I wasn’t happy as a VA. It was a lot of work and the work wasn’t exactly what I enjoyed. It included:

✅ Copywriting emails

✅ Proofreading/editing

✅ Publishing blog posts

✅ Designing landing pages in LeadPages

✅ Setting up email automations

✅ Account management

✅ Online course setup

Now, don't get me wrong. I was THRILLED with the supplementary income.

But at the end of the day, I was burned out. 

I was working nights and weekends, and I was exhausted. But I didn’t know what to do.

I was happy that I’d started earning money on the side with my virtual assistant work, and I didn’t want to start from scratch and do something completely different. 

So I decided to choose the service I enjoyed doing the most as a virtual assistant — and that was proofreading.🤓

I decided to be a freelance proofreader and make that service my main source of income. This, I decided, would now be my ticket out of the 9 to 5.  

Deciding to Become a Freelance Proofreader (2017)

Freelance Proofreader

Making the decision to become solely a freelance proofreader happened sometime in late 2017. 

And even though I wanted to drop all of my virtual assistant clients and focus solely on proofreading, I stuck with them a while longer while I figured out my transition.

And it was during this time that I felt stuck again.

Because while being a freelance proofreader sounded great, I realized I didn’t want to be just any old freelance proofreader.

I wanted to proofread online course curriculum and online course marketing content. 

As a virtual assistant, I spent a lot of time with course creators. 

I saw first-hand how much passive income they were bringing in with online courses, and I got a ton of experience helping them publish and promote them.  

So when I dove head-first into becoming a freelance proofreader, I knew I wanted to stay in the course creator niche. 

It was fun!

And not only because I loved proofreading online course copy, but because I loved learning! 

I figured getting paid to learn would be the best job ever, so at the end of 2017, I created Proof Mango: a proofreading service just for online course content. 

Growing Proof Mango and Pivoting…Again (2018 – 2019)

My Escape from the 9 to 5

Right at the start of 2018, I enrolled in B-School, an online course by Marie Forleo that teaches you how to build an online business you love.

So at this time, I put everything I had into Proof Mango, and into creating the ultimate proofreading service for online course creators.

And for the next two years, that is all I did: try to grow Proof Mango.

I enrolled in coaching programs, tried lots of marketing strategies, and took many online courses.

I don’t want to say I wasn’t successful. I used blogging as my content strategy to grow Proof Mango and saw a decent amount of traffic using SEO. 

I had also been really consistent in emailing my list with valuable content (even though I only had about 20 subscribers for the majority of 2018!). 

But it was really hard to grow Proof Mango. I didn’t know the right tactics to target the course creator audience, and I felt like it was taking me a really long time to grow. 

All the while, I was growing increasingly unhappy at my day job. 

I worked for an online advertising company doing compliance for online advertisements. 

I had worked there since 2010, and while I made some great friends (including my current boyfriend!), there was no room for growth for me there.

Not to mention, I had to look at some pretty unsavory online ads from time to time, and the entire experience left me feeling icky and to be honest, pretty depressed.  

So while I was still open to proofreading for course creators and growing Proof Mango, I couldn’t wait any longer for that business idea to take off. 

I decided to go ham on freelance proofreading for all types of content.  

Going All-In on Freelance Proofreading (2019)

Going All in on Freelance Proofreading

In the spring of 2019, I went crazy applying for remote proofreading gigs. I set up a Google Job Alert for “remote proofreading jobs” and got emails every day with new job opportunities. 

I also searched on Flex Jobs and Hire My Mom, my two favorite job boards, for full-time freelance proofreading gigs. 

Then, after all of my wishing, hoping, and hustling…

…in August of 2019, my dream of leaving my full-time job to do freelance proofreading was FINALLY realized — I landed a contract proofreading gig with Anthem, the health insurance company (now Elevance Health). I was free! 

As you can imagine, I was stoked! 

It was only a 6-month contract, but I knew this was the start of something great. 

My long-time dream of striking out on my own and taking on proofreading gigs on a freelance basis was finally becoming realized! 

I figured that by the end of my 6-month contract with Anthem, I would easily get more proofreading opportunities since Anthem would be on my resume. 

And sure enough, after my 6-month contract was almost up at Anthem, I found another proofreading contract opportunity with another Fortune 500 company, Cardinal Health.

At this point, it was December 2019, and I felt free to choose who I wanted to work with and when. I was on fire!🔥

Going BACK to the 9 to 5 and Creating an Online Course (2020-2021)

Creating an Online Course

Come February 2020, I was still happy to be doing contract proofreading work. But my contract gig at Cardinal Health started wearing on me a bit. 

The work wasn’t always steady, and the group organizing the contract work didn’t seem very organized. Also, the hours were super early — 6am–3pm PT. 

On top of it all, pandemic fears were brewing across the country. I was still loving life away from my old full-time job, but I was itching for something new and feeling pretty scared about COVID-19. 

Then, about a week later (still in February of 2020), my old boss at Anthem sent me an email.

She said they had an opening for a full-time proofreader at Anthem and wanted to know if I’d be interested in returning for a salaried position. 

Now, even though this was technically going BACK to the 9 to 5…I couldn't help but think about all of the discomfort I was feeling at my Cardinal Health gig.

So I immediately said yes. 

Even though I was super happy to be a contract proofreader, the thought of working with my friends at Anthem again and the opportunity for health benefits and salaried pay doing something I loved was just TOO good to pass up!

So from March 2020 to December 2021, I went back to a 9 to 5. This time, working as a professional, full-time proofreader for Anthem. 

Now, before we move on, let's talk about those first few months after I started working at Anthem again as a full-time employee.

It was May of 2020, and I received an email invite to become an affiliate partner for Digital Course Academy.

Digital Course Academy is an online course by one of my favorite online course mentors, Amy Porterfield. It teaches you how to create your online course from scratch and launch it with a webinar.

Now, truthfully, I bought this program in 2019 because I loved Amy Porterfield.

But in practice, I never made it past the first few modules of the course. Because at the time (in 2019), my focus was on leaving my full-time job and finding a proofreading gig.

However, in 2020, when I was invited to be an affiliate partner for Digital Course Academy, I knew instantly that I wanted to do it.

Being an affiliate marketer works best when you’re passionate about the product you’re promoting, and I was SO passionate about all things Amy Porterfield. 

I knew I could promote her online course (Digital Course Academy) to my audience in a genuine way. And I knew she would deliver an amazing experience to anyone I referred to her program.

On top of that, she was offering a pretty generous commission to her partners. So I applied to join her affiliate partner program in 2020 and was accepted!  

So in September of that year, after an insane amount of hustle and work, I promoted Digital Course Academy to my email list, which at that point, had ballooned to 320 people. 

I referred 10 people into her program, which gave me a little over $10,000. I had also ushered a few people into her smaller program, List Builders Society, so I earned a bit more income than I anticipated. 

Now, let's get one thing straight: This was an insane amount of money to earn with affiliate marketing. I had never, ever earned that much from anything other than a day job, and NEVER all at once. So I was feeling like a million bucks!

Not to mention, after that launch, in October 2020, I was inspired to create my own online course. 

So at the end of 2020, I decided to create my signature online course. My plan was to eventually put it on evergreen, so that one day, I could leave my 9 to 5 (again). 

So for the remainder of 2020, and into the beginning of 2021, I created my online course, Course Copy Essentials

Launching My Course and DCA…Again (Jan – Sept 2021)

Launching My Online Course

By March 2021, I had finished creating my online course, and I was about a year into working for Anthem. 

Unsurprisingly, I started to get fidgety again.

I still didn’t like the idea of being tied down to a 9 to 5, even though Anthem was a nice work-from-home opportunity that paid well, and I loved the work and the team.

But I got restless. 

At this point, I had a ton of proofreading experience and a finished online course that was ready for launch. 

I REALLY wanted to be a freelance proofreader with multiple clients, without being tied down to specific working hours.

And I REALLY wanted to launch my course and eventually, put it on evergreen.

However, I still didn’t have enough money saved up to strike out on my own.

Sure I had received a massive payday for being an affiliate for Amy Porterfield in 2020, but after taxes and paying off credit card debt? There wasn’t much left to fall back on. 

So I felt stuck. 

I decided the fastest way to generate some quick income was to officially launch my course with a webinar, the way Amy Porterfield teaches in Digital Course Academy (DCA).

So in June of 2021, I dove into DCA and learned exactly how to: 

✅ Create my entire webinar from scratch

✅ Write all of my email content for the launch

✅ Promote my webinar launch (and course) on social media

And by the end of July 2021, I delivered my first webinar and launched my course to about 400 people on my email list. (And to a few hundred people who followed me on Instagram, Facebook, and Twitter.)

At the end of my own course launch, I brought in about $1,000, which was pretty disappointing. It wasn't huge numbers by any stretch! But I was happy to have launched my course and made some kind of profit. 

And to me, the fact that I had actually LAUNCHED my course and did my first webinar, was enough to make me feel successful. 

Then, to my utter surprise and delight, I was invited AGAIN to be an affiliate for Amy Porterfield!  

I didn’t mention this before, but very early in 2021, Amy had announced that she wasn’t going to do affiliates that year. 

So when I was invited back in 2021, I basically felt like I had been pulled out of my body and into some next-level, metaphysical experience.

It was a beyond cloud 9 experience — like I was on a supergiant star somewhere in another galaxy, floating higher than high.   

So in September of 2021, I promoted DCA again to my email list. This time, I had about 500 people on my list — so about 180 more people than I had for the first affiliate launch. 

And after it was all said and done, I made a little over $14,000 from being a DCA  partner for the second time.

With this added income, leaving my full-time job was starting to get even MORE real. And I was starting to put together my escape plan. 

The Final Sprint to Escaping the 9 to 5 (Oct – Dec 2021)

Escaping the 9 to 5 Finally

After my successful partner launch for DCA in the fall of 2021, I knew my time to escape the 9 to 5 was close. 

Even though I still had more debt and taxes to pay with this second round of DCA affiliate income, this time, there would still be enough left over to act as my own personal ‘severance’ if I decided to strike out on my own. 

And while I was excited at the thought of eventually launching my course again and potentially putting it on evergreen for steady income, I knew that if I wanted to escape the 9 to 5 quickly, I had to start with service income again — specifically, my proofreading service.

I felt like I had a leg up because, at this point, I had a ton of proofreading experience, as well as big names like Anthem and Cardinal Health on my resume.  

So in late November of 2021, I decided to go ‘ham’ again and find as many proofreading gigs as possible.

This time, I wouldn’t be looking for full-time contract gigs, but smaller, temporary gigs for multiple people.

I’d also picked up a book called The Six-Figure Freelancer that gave me some great tips for making my freelance dream possible. 

Now, while escaping the 9 to 5 felt closer than ever, I knew I had to think seriously about my plan and make some key decisions so I didn't drown when I put in my two weeks' notice.

I decided that I wouldn’t quit my full-time job at Anthem until I had found enough proofreading clients to replace about half of my monthly salary.

My plan was to rely on my ‘severance’ to make up the rest. At least in the beginning.

It was a gamble, but I knew that leaving my full-time job would also free up a ton of time for me to actually search for proofreading gigs. So I felt confident this plan was a good start. 

So my first step in early November 2021 was to find enough proofreading clients to make up half of my monthly salary. 

First, started emailing previous clients. I reached out to an agency I used to proofread for, and much to my delight, they welcomed me back with open arms (and even accepted my newer, increased rate!).

Next, I reached out to a few people who had LEFT that agency to see if their new jobs needed a proofreader.

And sure enough, a gal I worked with at the agency had moved to a SaaS company that needed a proofreader, so I grabbed another gig quickly that way too! 

Then, I decided to jump into Upwork and see what gigs I could get. 

It takes a long time to start making regular income on Upwork. But I enrolled in an Upwork course and dove in.

And while I didn’t make enough money on Upwork in November or December of 2021, I DID end up with enough proofreading work to make up half of my monthly Anthem salary by the end of November of 2021.

So I took a deep breath, had a discussion with my boyfriend about it, and TOOK THE LEAP! 

(Cue Bon Jovi’s Livin’ on a Prayer!)

FINALLY Escaping the 9 to 5 (2022)

Finally Escaping the 9 to 5

When I put in my two weeks’ notice at Anthem in December of 2021, I knew two things for sure: 

I had enough proofreading income to pay half a month’s worth of bills. And I had a ‘severance’ to cover the rest. 

For about 3 months. 

And this scared the crap out of me. But there were a few things that helped me realize that I COULD strike out on my own. For example: 

➡️ I had a marketable skill that could always get me work

➡️ I had free time to explore new opportunities 

➡️ I had GRIT — with no reliable income, I knew I was capable of doing everything and anything I could to make the freelance life work

➡️ I had a finished online course, which I knew could bring me steady passive income on the side

➡️ I had great affiliate partnerships that I could promote to add new revenue streams

➡️ I had a growing, engaged email list who enjoyed the content I sent out each week

And as of today (July 25th, 2022), I’m still making it on my own as a freelance proofreader. And I'm promoting both my online courses and affiliate products. 

I eventually got the hang of Upwork in January of 2022. Now, it offers me about $1,000 in steady proofreading work per month. This is a great addition to the clients I already have! 

I'm also routinely running promotions for my favorite affiliate products, in addition to promoting my own online course on evergreen.

My system isn't perfect. But hey, those first three months of the year have come and gone, and I'm still here!

Resources for Escaping the 9 to 5

Resources for Escaping the 9 to 5

If you’re looking to quit your 9 to 5 in the near future, I encourage you to do the following:

  1. Figure out what you’re good at (and stick to it)
  2. Don’t be afraid to diversify your income (between service and info products)
  3. Save as much money as you can to give yourself a ‘severance’ (so you’re not depleted when you quit your job)

That being said, here a few resources I highly recommend to get you started: 

Job sites for remote freelance work or other gigs:

Resources to start a freelance gig: 

Resources to learn how to build an email list:

Resources to learn how to create an online course: 

Resources for engaging your email list: 

Resources for blogging:


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Monique is an online course proofreader from sunny Los Angeles. She creates info products related to writing course copy, like her flagship course, Course Copy Essentials. And she loves helping course creators look good in copy. You can find her curled up with coffee and a good book when she's not proofreading course content and absorbing everything related to online learning.