In 2012, at the age of twenty six, I got my first “real” job.

I had been substituting in the charter school where my wife worked. They offered me a full time position with the Title 1 department. The salary was modest—just $26,000—but it was the most money I had ever made.

It also had health, vision, and dental benefits. I went to the doctor for the first time since college.

Combined with my wife’s (also meager) salary, we were livin’ as high on the hog as we ever had. We did our grocery shopping at the Farmer’s Market. We would even stop for gyros on our way home from work on a whim. My record collection grew by leaps and bounds.

We even bought a house! We were truly living the Millennial’s version of financial success.

But then something happened that we didn’t anticipate.

I got laid off.

And instead of trying to jump back into subbing or find another teaching job (note: I don’t have a degree in education), I decided to try writing freelance.


Four and a half years later, through some twists and turns, I’m still here, and my love for freelance is stronger than ever.

Here’s why.

The Demand is Growing

When I first hopped onto four years ago looking for clients, it was work. Not many people had ever heard of content marketing, let alone search engine optimization. Most of the writing work out there was super technical and didn’t pay what it was worth.


Now, everyone is worried about their ranking on the SERPs. SEO firms like Fanatically Digital have too many clients to handle in house, so they’re turning to freelancers.

I’ve even had local clients approach me to help them implement content marketing on their website. And without doing anything to advertise myself.

And that demand is only sure to grow, which is good news for me.

Can’t Beat that Freedom!

I forgot to mention my daily schedule at the school.

The school day ran from 8-5. Yes, the students were there until 5.

Staff was required to arrive thirty minutes early and stay thirty minutes late—though we often ended up staying later.


I had one free period, during which I did all of my grading and lesson planning. It wasn’t unusual for that prep period to be eaten up with meetings with administrators. It was even more common for my to support another teacher during that time.

Any grading and prep that I didn’t finish in that free period was completed in the evening.

The only thing that saved my marriage during this time was that we were working at the same school. Otherwise, we would never have seen each other.


Cut to present day.

My wife and I ease out of bed somewhere between 8:30 and 9 (p.s. she’s self employed now too). We eat a nice breakfast, do some yoga, and take our dog for a walk. Sometimes, we might have some friends over.

I generally grab my laptop around eleven and check my emails and build my to-do list. I either spend the day at home listening to records, at my wife’s shop, or at one of my favorite coffeeshops.


If a friend wants to grab lunch, I can. If I need to take care of something around my house, I can.

Some days, I don’t do any writing at all until 8pm. And those days are still just as productive.

I forgot to mention it earlier, but I’m a musician. I play in two fairly active bands in town. And managing those bands take a lot of time that I didn’t have when I was teaching.


Freelancing allows me the flexibility to give time to the things I love without sacrificing my paycheck.

The Pay is Great

There’s something I didn’t realize when I decided to pursue freelance.

Not only does it give me enough money to cover my bills, but I live pretty comfortably.


In the last four years, I haven’t missed a single mortgage payment. We still go to the farmer’s market every once in a while. And my record collection is still growing.

And keep in mind: my wife doesn’t pay herself from her business yet. My income alone is enough to pay all of our expenses.

This year, my take-home from freelancing will be more than my salary at the school. With about ten percent of the headache.


Freelancing is not without its drawbacks though: I have to set aside my own money for taxes. My insurance comes out of my own pocket.

But that’s a small price to pay for time freedom.

So excuse me if I’m not chomping at the bit to get back into a 9-5.