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How my wife & I accidentally became profitable full-time freelance teachers

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When my wife, Jamie, and I graduated from college in 2010, there were two things we never thought we’d be doing for a living: freelancing, and teaching.

Who wants the stress of not knowing when your next paycheck is going to come in, and how much can someone really make on a teacher’s salary?

Fast forward to 2014.

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Life Before Freelancing

After working as a motion designer at a production company in LA for nearly five years, Jamie and I were ready to start a family.

She had already been freelancing from home as a graphic designer.

Through connections and friends, clients started asking me to create graphics for their projects in my spare time. Before I knew it my nights and weekends unintentionally became filled with side work.

I realized that my day job was actually taking away from my side work, and that I had basically become a freelancer myself. Knowing that a baby was on the horizon, if we were going to make the jump to full-time freelancing, now was our chance.

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Making the Jump

So in December of 2015 I put in my two weeks notice, went on Christmas vacation, came back to LA in the new year and started a new life as a family of freelancers.

At the beginning of this career-shift I had plenty of work already coming in, but I knew that could change at any moment. So I explored other potential sources of income to act as a financial safety net for the slower months.

Teaching for Skillshare.com

At the time I had one class on Skillshare.com teaching motion graphics.

Skillshare is an online learning subscription platform that allows teachers to post pre-recorded project-based classes. Most of the work is done up-front, which makes for a nice form of residual income.

My first class brought in a decent amount of income when I first posted it a year before, so with a little nudge from the Skillshare team I decided to try teaching again.

It was something I was passionate about and really enjoyed doing, but I didn’t know if it would actually be worth the effort.

My second class ended up being a success and doubled my student following in a month. So I decided to teach another class.

And another…and another..suddenly Skillshare was an important contribution to our monthly income.

Making Teaching on Skillshare.com Our Income

That’s when I turned to Jamie (who was the one that got me to teach in the first place) and told her she should be teaching too!

It took her a few months to warm up to the idea, but her first class was a huge success and a great jumpstart to building her own following on the platform.

We’re now making more from Skillshare alone than I did at my day job of five years.

On average, it makes up 50% of our monthly income.

Where We’re at Today

Today we’re a family of three (four if you count our pup, Pixel) who accidentally became full-time freelancers and teachers.

We’ve come up with a structure for our monthly workload that begins with Skillshare. Our goal is to each post a new class on Skillshare every month to bring in regular income.

Posting new content consistently on Skillshare creates a snowball effect that regularly builds our following and income.

Next I set aside time for a few clients who bring in consistent work.

Then with our remaining time we’ll decide how we’d like to spend the month as a family, and I take individual freelance gigs that line up with that schedule.

Wrapping it Up

Having multiple sources of income, especially the residual income from Skillshare, allows us to live the lifestyle we want.

A lifestyle that’s not consumed with busy commutes, limited vacation days, or working for someone else’s dreams.

Instead we get to spend 100% of every day together as a family. We’re able to do what we love for a living and get to raise our son in an environment that promotes creativity.

That’s something we never even imagined was possible; but now our hope is that as Elliot grows up he’s able to see that if you set goals and work hard, it’s completely possible to make a living doing what you love.

And hopefully he’ll have a few Skillshare classes of his own before too long :).

So even though this lifestyle wasn’t what we thought we’d be doing originally, we’ve embraced it as a family and will never look back.

Have you made the jump to full-time freelancer? Tell us in the comments!

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About Jake Bartlett

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  1. Great inspirational story… just what I needed at this time.

  2. Kathy Mcneil says:

    Great story-and gives me ideas for what I want to do in my career at this point. What do you do about health insurance?

    • Unfortunately those kinds of benefits don’t come with the freelance lifestyle. Life, health, and any other type of insurance is out of pocket. But the benefits that really matter to us as a family, like taking as much time off as we want, outweigh those drawbacks.

  3. Thanks so much for sharing your your story!

  4. Loved reading this! Seriously thinking about teaching at Skillshare! I’ve been looking for something like this and it just clicked in place for me. Not sure what I should teach yet…any ideas? Or how did you decide on your first course?


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