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 for his graduate work.
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 look 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 because 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 one 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.
6. It’s good to work for someone else.
I can’t speak for the World At Large, but I can say that bosses in education are interesting. Teachers generally long-outlast administrators for a multitude of reasons, but administrative careers aren’t short either. In fact, I’ve been at my current job for nearly a decade, and I’ve only had two principals (I have had 5 assistant principals, though).
Side hustling is a prime opportunity to see what it is like to work for different people. Call them clients or bosses, but it’s largely the same in the sense that I have a chance to work with other people who choose to employ me. And it’s good to have that experience.
Not only does it help me see the contrast between the education space and the World At Large, it also helps me realize what I’ve long assumed as normal doesn’t have to be. Just the other week, one of the people I side gig for said, “I’m here to eliminate roadblocks. What can I do to make you even more efficient?” As education becomes increasingly, let’s say, complex, I feel like the entire concept of efficiency has been long forgotten. Single-tasking is back in vogue in so many spaces. Education is not one of them. Quite frankly, if I’m not wearing at least 12 hats at once, I feel like I’ve forgotten something.
Side hustling doesn’t solve problems at my full-time job; but it does remind me not to accept everything as is.
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?
This post was originally published in January 2019. As my side hustling tenure increases, I’ve realized that I have new reasons to continue my side hustle even though I don’t have to. This post now reflects those realizations. Now who wants to help me pitch the idea of single-tasking to my principal?
This is like totally my own fault, but I just don’t know how to break into the whole side hustle game. I’ve written for some companies but they’ve mostly been unpaid (I know, I know). If I ever did properly break into side hustling, I think it would a long term thing because I’d be saving for longer term things like retirement and paying off my mortgage.
That’s what we are doing with my side hustle money. After I am absolutely positively certain that I have done my taxes correctly, we put it toward the mortgage!
I didn’t know how to get started with anything that I could do remotely. Tutoring was easy because I’ve been doing that for as long as I’ve been teaching! But once I let one person know I was interested in writing, I was shocked how fast it snowballed!
What do you do with your side hustle income? Do you put it with the rest of your money or do you treat it differently?
I keep it separate, and I actually don’t spend any of it until after taxes have come and gone! Afterward, we put a good hunk of it toward our mortgage.
The only exception to this is our teaching stipends. Since our schools taxes those through our W-2, I’m less nervous about that. We put those toward travel or a house catastrophe.
It took me 3+ years of my Uber side hustle to learn to say no. Whether that be a ride request too far away (that would result in me actually losing money on the trip, if I value my time at anything) or cancelling the ride when the overly-intoxicated passenger came stumbling up to my car.
And I’m all sorts of thankful for #2 when it comes to this blogging thing. I consider my blogging buddies to be the best friends I’ve ever had, and while some might consider that sad, I truly appreciate the advice, acknowledgement, and positive peer pressure (ahem Penny) to continually strive to improve and be my best self. And when I get to spend time with members of this community, I feel like I’m floating on clouds, because everyone is so uplifting. I can’t wait for FinCon friends to re-assemble in DC!
I agree! There’s a lot of good that comes from these interwebs, Josh!
I stopped for two years because I was working too many hours at my day job. That was a big mistake! Cutting back to enjoy your little one while he grows up is important. Trust me, they grow up fast!
That’s what I’m learning! So now I stick to evenings and nap times (on the weekends). I do regret missing out on those naps, though!
Sounds like you are doing well. If your savings are above your projections, perhaps you may want to readjust your goals to increase investments or plan to retire earlier. Great to be ahead.
You’re absolutely right! I do need to decide what exactly I’m aiming to do with this income. Right now, we use it to pay down our mortgage (it’s not math, it’s psychology for me!), but we do need to rerun our numbers re: retirement!
I’m all about the side hustles.. they help diversify immensely, which I think is as important in professional life as it is in investments. I do need to be better about turning down SOME work, though 🙂
I feel so much more confident about our money situation with a side hustle. We have a solid emergency fund, but I much prefer a second income stream. After getting canned twice (after I was formally rehired!), I don’t think I’ll ever truly trust a W-2.
Side hustling is something that’s very new to me, but I’m looking to expand more into it! I too do not need it as my W-2 income is more than sufficient, but I know that anything on top can help me reach my goals faster! One thing I’ve learned from my current side hustle (charging electric scooters) is to not to take myself too seriously. I’ve been laughed at before as people see me riding a couple scooters at once and all I do is smile back knowing it’s helping me get that much closer to freedom!
Isn’t it funny what people will take the time to concern themselves with?! Good on you for doing it anyway!
I just signed up to be a Lime Juicer (the electric scooter) because you get to ride the scooters for free in between the time you pick it up and when you release it… I don’t think it’ll be too lucrative, but it could be a decent side hustle since we live right next to scooter release points.
In all seriousness, my writing started as a side hustle and has turned into my primary way to produce income. It got us through Rob’s last three years of school, and it allows me plenty of flexibility to be home with the kids. To me, the main value of a side hustle is that it allows us to increase income when we need it, and we can back it off when things are a bit more secure.
You are my continue source of inspiration, Hannah! And you know I am going to need to know ALL THE THINGS about Lime Juicing 😀
Give me a couple of weeks and I’ll guest post for you! Post to be entitled- How to get free pizza and scooter rides (subtitle- what I learned about hustling and life from my high neighbor).
Nice post. Had a chuckle about the 15 photocopy comment. Yeah, we’ve been there….my wife’s school ran out of paper back in November. We have bought her more, but she needs to keep it in her car to prevent it from getting stolen by other teachers. So yeah, crazy times.
Oh, and she has to bring in extra food each day, since she has kids that usually have not eaten a meal since the previous school lunch. (Monday’s are especially tough.) The good side benefit is that the kids are easier to manage and learn better with the extra food….turns out that starving kids don’t really learn well. Go figure. Not sure that people realize the social issues teachers have to deal with every day ?
It’s so true! I used to always just keep stashes of food in all my drawers, but it’s gotten increasingly hard with needing permission. Our school tried to get us to send home a photocopy of an ingredient list and nutrition facts for everything single thing we let kids eat. UM. WHAT.
Now I send home a permission slip asking if kids can have snacks or rewards, what their restrictions are, and go from there.
Props to you for supporting your wife. Teaching is hard. Being married to one is hard too 😉
Hehe great post. I too make nothing from my side hustle. Is it called a side hustle if you make no money?
I am at the point where I don’t want to put in the effort to make a ton of money, marketing, quentity of posts. I don’t post often but when I do I want it to be good content.
And while reading your post, there is one tskeawsy I got. You are a terrific writer.
Thanks, Mark!
Thankfully, I have plenty of actual paid side hustles. I just haven’t/don’t/won’t monetize this one. But it’s a great reminder (for me!) that you don’t have to monetize everything. It’s led to a bunch of work indirectly!
Side hustling is a great way to learn to say no! When I first started, I took on waaaay tooo many projects, and spread myself really thin trying to get everything done. Now I’m a lot better about balancing everything. It’s such a hard (but rewarding) lesson!
I’m definitely a side hustler! Having my My side hustle and blog are what help me make it through the day at my regular job and give me something different to look forward to everyday. I’m not a natural people person, and my side hustle pushes me out of my comfort zone in that respect which is a good thing for me. It also helps pay the bills for sure – I couldn’t make it on my regular salary, and yes, I have been doing it long enough that I’ve become better at setting boundaries. And as for my blog – I am an insatiable learner, and my blog really helps tick that box for me as well.
Love your blog, Penny – it’s one of my favorites.
Oh, that means so much to me. Thank you for saying that, Barbara!
I love that you use your side hustle to move outside your comfort zone. That’s a great one to add to the list!
This is one of my favorite posts of yours Penny. You are so honest, entertaining, and insightful. We are all learning from you and your selfless tone. I feel conflicted about side-hustles right now as a new mom too. I really needed to hear this, so thanks! I’ve always loved to learn, grow, connect, and journal. I’ve enjoyed turning some of my writing public, but right now I’m typing over my child while he sleeps on me… I’m not sure what to make of this crazy world!
I think there are seasons, and just because you aren’t side hustling now doesn’t mean that you won’t in a year or month! And vice versa. I messed up the timing tonight, and I didn’t get to say goodnight to HP. So now I want to delete this entire post 😉
But I think that’s the new mom thing I’m still sorting out myself. I want to give him as much of my time as I can, but I know that doesn’t mean I need to give him *all* of it. I just need someone to tell that to the Mom Guilt I feel!
Keeping all these spigots at standby is such a wise choice, too. You can always say no to more. It is harder to begin the attraction of work though.
It’s so interesting to hear about others’ careers because it’s so easy to lose sight of what works or doesn’t in our own careers. Your side hustles give you the opportunity to learn how non-academia works, which I’m sure is completely different from how health care works. This reminds me I need to explore side hustle options again.