How I Started Working From Home Two Years Ago

I started working from home as a pure accident. If you're a person of faith, it is the work of God looking back, but I didn't know it at the time. If you're thinking about working from home but think it's impossible, I hope this post will help you change your mind!

Trust me, if I can do it, you can too!

April 2018 marked my two-year anniversary of working from home (most of the time). Although it hasn't been a vacation, it's better than what I did for the seven years before!

What I Did Before I Started Working From Home

trains long 1449071

When I say anybody can work from home, I mean it. There are very few entrepreneurial bones in my body, I flipped burgers in high school, and changed my career path three times in college (but I kept the same major–Political Science–the entire time) and only went to college to get the piece of paper which has sat in the original cardboard tube since the graduation ceremony in May 2008.

If you're a long-time follower of this blog, you may remember my first job out of college was as an operations supervisor with a large transportation company. While this job was a great experience, I knew from the start that I would need to find a different career path or become a miserable old man at the age of 40.

Thankfully, I met my wife along the way through a mutual friend and I finally found a great reason to leave. After crunching some numbers to make sure we could afford a career change, I turned in my notice and two weeks later we moved three hours down the road and I started my new job. This is the short version of this story.

How My Old Job Prepared Me To Work from Home

For the last four years as a supervisor, I was assigned to a territory that was roughly 200 miles long. I was given a company car, cell phone, and a laptop with a mobile wifi hotspot. Although we had an office, I mostly worked out of the car and my house. Since I was on-call 24/5 for these years, you learn real quick to get your work completed ASAP because you don't have regular office hours.

When everybody else goes home at 5, I would still have another three hours to the entire evening left to work depending on the day.

Having to set my own schedule and work pace was a huge blessing in disguise. I still had a superior to report to, but for the most part I was my own boss. And this liberty was great, because I could disappear when the operations were slow. If you didn't, you'd burn out quickly because the job will consume you.

While working from home isn't a 24/7 work cycle, it's not structured shift work with designated working hours and time off. At least not when you first start out.

How I Started Working From Home

So after I quit my job as a supervisor, I ended up taking an unplanned eight month sabbatical. Some people go to Hawaii or backpack Europe during their sabbatical, but I was pouring sweat equity into our house. Yes, my wife taught ballet one day a week and this income paid our monthly expenses during the transition.

When I wasn't working on the house, I started this blog (Money Buffalo) as a way to make passive income. This blog is still a hobby, but it ended up launching my freelance career so I can work from home four days a week!

As April rolled around, I needed to find a way to start making money. I kicked a few tires with local employers but it just didn't feel like that was the direction we were being led to. So, I stumbled across a freelance platform called Upwork and started pitching clients that were looking for freelance writers. Since my personal blog was about seven months old at this point, I referred potential clients to Money Buffalo for writing samples.

Where You Can Start Working From Home

I found my start on Upwork, but you might also consider joining Fiverr. Both of these sites are platforms where you can find gigs for the following income streams:

  • Freelance writing
  • Graphic design
  • Programming and coding
  • Video and animation
  • Translation
  • Music and audio

While I highly encourage joining a freelancer platform if you have zero online presence, the competition can be fierce and the pay isn't the best. Plus, most of the projects are one-time affairs. To diversify your income streams, I also recommend pursuing one of these side hustles to land additional, ongoing gigs.

Is Upwork Legit?

Yes! But, I recommend freelancing on other platforms too! (Freelance writers might try Target Writers)

Below is a screenshot of my Upwork bio to prove I'm a real person who's made real money from Upwork:

Working From Home

Although I got my start on Upwork, I only have one long-term client on the platform presently. I still do some one-time gigs periodically, but my other clients are all from word of mouth from other personal finance bloggers.

With that being said, Upwork was my sole online income stream for the first year where I usually had two clients at any time. Although, I did go two months without a client because one decided to sell their website and the other had a drop in blogging income and needed to cut writers.

If you decide to freelance on Upwork, take these tips to heart:

  • Only converse with clients that have a “Payment Verified” icon, non-verified payment clients are scams
  • If you're a freelance writer, never write for less than three cents a word (try to get 5 cents per word)
  • Look for work from established companies when possible

In my experience, most of the blog clients are worked for were brand new blogs that had a limited budget. If the site didn't gain traction in the first few months, the contract was terminated because they could no longer afford a staff writer. I found myself pitching new clients as much as writing for the clients I already had, this gets old but it's part of the business until you can establish a name for yourself.

Network With Others Online

My “big break” finally came about a year ago, thanks to a conversation with another blogger friend who I probably can never thank enough. For the last year, I've had the privilege of writing for established websites and haven't had to pitch new clients. Although I still pitch article titles on a regular basis, this is far different.

If you want to work from home as a freelancer, you need to get a website. I personally host mine with Wealthy Affiliate (the name's a bit cheesy but it's web hosting platform and they also have a blogging course too). Plus, you can host multiple websites for one flat annual fee; my wife and I have about four websites for our different self-employment ventures.

I write one post a week and I try to spend more time visiting and commenting on other blogs. I haven't been as diligent in 2018 about visiting other blogs since I overcommitted to some local projects at our local schools this year and we now have two small children under the age of three. I'm scaling back on work commitments starting in June though so I'll be more active in the blogosphere in the near future.

If it wasn't for this networking, I don't know where I'd be right now as a freelance writer. I never expected to become a career freelance writer when I started visiting other bloggers, we were just looking to communicate with like-minded people.

Learn New Skills

During my sabbatical–and even now–I took a few online courses. Thankfully, they aren't like going back to grad school or the such.

My favorite online learning platform is Udemy. I've taken writing courses on here for $10 each. They have courses on everything, so if writing isn't your cup of tea, there's still a course for you!

There's plenty to choose from, so I recommend reading the feedback ratings or watching the intro videos before you purchase a class.

Take Your Job On The Road

One benefit of working online is that you can work from anywhere with an internet connection. Although we still need to stick close to home during the school year because we both teach part time, we usually travel three weeks a year as a working vacation.

As a freelancer, you no longer get matching 401k contributions or paid time off, but the flexibility is awesome if you use your time effectively.


I could go on longer, but I'll wrap it up here. If you're just exploring the possibility of working from home, I hope my testimonial has helped. My wife and I enjoy the flexibility of working from home and never want to return to Corporate America. Although you might not have sick time, paid vacation, or other employee benefits (as a freelancer), the freedom to work when you want and where you want is awesome.










Josh founded Money Buffalo in 2015 to help people get out of debt and make smart financial decisions. He is currently a full-time personal finance writer with work featured in Forbes Advisor, Fox Business, and Credible.