Why I’m Still Making Time to Side Hustle

“Wait. You’re still writing?”

You might think that’s in reaction to people learning that The Little Blog That Could is still chugging away. But the truth is, very few people in my real life know that I blog. And only one person–my husband–knows the name of it.

That’s actually the comment I get from people when they learn that I’m still side hustling. Yup. Even now. Mid pandemic, mid Zoom/hybrid/in-person school, mid pregnancy.

While I’ve really had a love-hate relationship with side hustles over the course of my life, I’m really glad that I’m still making time to side hustle at this particular juncture.

In fact, it’s been helpful beyond measure. And I realize that maybe if I talked about that more, people would be less shocked when they find out that I’m still happily freelancing.

It feels like fun.

While there are definite dangers to monetizing your hobbies, freelancing continues to prove to be a beautiful blend of both for me. Writing is a true passion of mine.

The fact that people will literally pay good money for my words is something that never ever stops filling me with wonder. It is a thrill.

One day, I’ll run the word count on my honors thesis and see how much VTSAX I could have had by now had that been a paid writing gig. Wink!

Of course, I don’t ever want to only write for money. But the fact that I’ve been able to monetize something that I love to do really is absolutely fun for me.

It also feels like freedom.

Teaching feels a little bit like existing in a fishbowl. As outside pressures mount, it’s hard to not feel that every move you make is watched and documented, so you can later justify it.

Of course, I still get to shut my door (in non-COVID years–this year, it’s open for ventilation!) and do my own thing most days.

But freelancing is a different kind of freedom. I relish the fact that I’m free to make as big of a mess during the process as I’d like so long as the product turns out well and deadlines are kept. It’s a different type of autonomy.

And the fact that there’s no push to standardized the practice? Well, that couldn’t be more different from education this past decade. What used to be very much the art of teaching has now become a science–prescriptive, formulaic, data-driven. So, perhaps, the least science-y part of science.

Writing? Freelancing? It’s the complete opposite. And I relish that freedom.

I value the relationships.

Part of why side hustling used to be so challenging for me is that I used to say yes to every opportunity. Even if it meant working for Some Real Big Jerks.

For the past few years, though, I’ve learned that the best way to side hustle is to say no more than you say yes.

That way, the work you do take is more meaningful. I’ve really gotten the chance to build relationships with clients, and I can honestly say that I enjoy working with these people as much as I enjoy spending time with my coworkers and my friends.

It’s a nice reminder that there are options…

I don’t have to be a teacher forever.

Spoiler: I probably will be.

Most days, most years, I can’t fathom a world where teaching isn’t part of my life. I just love it too much.

But teaching can and will break your heart. Everyone knows that. Whether you teach for five minutes or fifty years, you’re going to get your heart broken. The problem now is just how long the heartbreak lasts.

Listening to my profession be constantly maligned is taking a toll on me.

Sure, there’s the usual “But you get summers off!” crowd, but I can and do mostly overlook that sentiment. This year, it’s different. It’s unveiled vitriol, and it’s everywhere–newspapers, radio stations, social media posts from families in my own community.

While I don’t have any real intention of leaving the classroom anytime soon, I’d be lying if I didn’t admit that knowing I’ve already laid the foundation for something else is deeply satisfying.

…and that not everything is different.

Ask any teacher. Most of us feel most like ourselves in our classroom. But given this school year, what my classroom looks like has changed more times than I can count. Truthfully, it’s unsettling. Not just from a midnight-oil planning perspective either.

Teaching is very much a part of my identity, for better or for worse.

That means that not only has my classroom been turned upside down this year, but who I am as a person has as well.

The fact that I’ve been able to more-or-less keep plugging along in my writing world, though, brings me so much peace. That isn’t to say that I didn’t lose clients or that the pandemic didn’t impact freelancing or freelance budgets. It absolutely did.

But freelancing ebbs and flows naturally anyway. And it’s one constant that I’ve really savored this past year.

So Tell Me…Is side hustling fitting into this season of your life? Have you ever side hustled?


  1. Robert Larkin

    I share your love of writing and teaching. My side hustle for the last 23 years has been teaching online. I retired from my 9-to-5 job in archaeology and environmental planning about six years ago. However, I simply cannot stop teaching or writing.

    I recently realized that over the last 23 years of working as an adjunct faculty member, I have had in excess of 4000 students. Interestingly, I never met a single one of them, although I am connected with a number of them on LinkedIn.

    I continue to develop courses and to teach, but the majority of my writing is now attempting to be humorous on Facebook.

    Thank you for your great posts and articles!

  2. PENNY! “Teaching feels a little bit like existing in a fishbowl. As outside pressures mount, it’s hard to not feel that every move you make is watched and documented, so you can later justify it.”

    Yes– I feel this so much as a government employee! That was such a perfect way to put it. I’m glad you’ve been having a great side hustle experience in 2020-21.

  3. Teachers have been through it this year.

    It’s gonna be a long, difficult road. I’m so glad people like you are still here–especially ones who have other choices.

  4. I used to think that side hustle was just way too intense for me to be interested in getting to. Turns out, side hustles are AMAZING. You get to control your own destiny without having to make a 100% risky jump to a new venture.

    Risk free with unlimited potential is an opportunity that can’t be found anywhere else in the world. Side hustles for the win!

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