5 Reasons I’m Still Side Hustling Even Though I Don’t “Need” To

If my relationship with side hustles had a status, it would be this: It’s Complicated.

As someone who worked multiple jobs as soon as I got my work permit at 14, my relationship with side hustles is as varied as it is long. Even at moments when I absolutely hate it, even now that I don’t actually need the money, I just can’t quit. Right now, we don’t need my side hustle income. That is dramatically different than the reality leading up to my maternity leave. During the unpaid portion of my leave, we realized that while we save half of our income, my husband doesn’t earn half our income.

And that, friends, was that ever a doozy of a math problem. Insert side hustling. In addition to scrimping and saving in the time leading up to my leave, I side hustled as much as my exhausted and sick self would let me. It should surprise exactly no one that I found myself burned out on side hustling. I went so far as to declare its stupidity.

And yet, here we are. I’ve maxed out my salary (though I won’t see the full benefits for another two years thanks to some contract language shenanigans). My husband has landed another raise. We can pay our bills and save without a side hustle. And yet, here I am. Still side hustling. While I know part of it is habit and part of it is pressure (good pressure!) from the money people I surround myself with, I have actually come to see side hustling in a different light. For now.

1. I finally learned how to say no.

I can’t guarantee that this is a lesson everyone will learn side hustling. But I can tell you it’s a lesson that I’ve been trying to learn for the bulk of my life, and it was a side hustle that finally taught me how to do it. I worked for a jerk with a Capital J. And like any relationship with an awful power dynamic, it took a lot of time and effort to finally say no and actually stick to it.

But my goodness if it wasn’t the absolute best feeling in the world to wish their child well, send a list of other resources, and hit the block button with a Capital B on my phone. And in my email. It’s really empowering to learn how to put yourself first. 10/10 would recommend. And I’m forever grateful that a side hustle taught me how to do it.

2. It’s great for networking even if you’re not.

Like most bloggers, I started this blog as a hobby. Unlike most bloggers, it’s been 3.5 years, and it is still 100% hobby.

Meaning I make no dollars directly from my site. Meaning I still don’t have Google Analytics. Meaning I got a lot of weird looks at FinCon. (But whatever, my blog won an award! I’m an award-winning hobbyist!)

But what this blog has done for me is helped me network like gangbusters. To say that I’m out of practice networking in the education world is the truth. Sure, I attend and lead professional development. I take my career very seriously and want to be the best version of a teacher for my students. But after being bounced around so much at the start of my career, I’m not leaving my current position unless I’m kicking and screaming.

Blogging, though, has helped me make connections to other people. Even though I am hecking awkward, I have still made so many blogger buddies. And once I started layering in freelancing, so many networks unfolded.

Why? I suspect because people on the Internet understand a secret: there’s always money and there are always clients. I might have started teaching with a scarcity mindset, but I am 100% abundance when it comes to realizing someone will always need copy written or edited for a new site. And there are so many new sites.

3. I love to learn.

Part of what makes me a good teacher is I understand how awful boredom is in the classroom. While there’s nothing I can do to spice up the directions on standardized tests, I do spend a lot of time thinking about how I can infuse my lessons with critical thinking, creativity, and movement.

Why? Because I remember loving some classes and hating others. Those classes I loved? I’d stay in them forever. Honestly, I think the reason I’m a teacher is that it’s the closest thing to Professional Student there is. And freelancing lets me learn so many new skills that are similar to my work but not identical. I love the challenge, and I love the new knowledge.

4. I’m enjoying Total Flexibility.

My blog, my rules. Total Flexibility is now A Thing. And I’ve got it.  I made a promise to myself that I would only side hustle if it didn’t interfere with time with my son. Because he was a snoozing pile of adorable baby last year, I didn’t have to worry about this too much. But now that he’s a toddler, I want to soak up all of my seconds with him.

Until he throws a fit when I stop him from headbutting the fridge.

The best part of the side hustling the way that I am currently working is that I feel very little guilt about it. Because I don’t look at it as lost time, I can really savor the work that I do.

5. You never know when that status will change.

With the economy in a bit of a tailspin, it’s been interesting to hear people talk about how recession-proof teaching is. As someone who experienced a lightning strike not just once but twice during the last recession, I can assure you most certainly that Teaching. Is. Not. Recession. Proof.

Yes, we will always have some type of schooling. Yes, there will always be a need for teachers. But unless you’ve been inside a school district to see the budgetary gymnastics that school boards and superintendents are capable of, you will have to take my word for it. In fact, remind me to tell you the story of the year that I could only run 15 photocopies a day and taught over 90 kids.

See. Budgetary gymnastics, but I digress.

Even if you or I have stumbled upon a recession proof job, there are bad bosses, bad coworkers, and all sorts of other possibilities to contend with. Plus, unless things change dramatically for me in this next contract, it looks like if I were to ever need to take another maternity leave, it will be just as unpaid as the first one.

Just because I don’t need a side hustle now doesn’t mean I won’t need one in the future.So I choose to monetize more of my passions, keep my skills sharp, and side hustle away.

Final Thoughts on Why I Still Side Hustle

I don’t know if I’ll side hustle forever. I don’t know if I’ll still side hustle next year. All of that uncertainty is just fine with me. Why?

I’m finally at the point where side hustling is a total choice, and it’s a choice that I’m happy to make right now.

So Tell Me…Have you side-hustled during a certain season of your life? Or you do you think you’re a lifetime side hustler?

Penny is a married millennial and first-time mom living in the suburbs of Chicago. She and her husband have joined forces to repay over $90k of debt on two teachers’ salaries. She chronicles her adventures in side hustling and frugal fun with a side of sass on her blog She Picks Up Pennies. 

Image via Unsplash