1. 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!

    • 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.

  2. 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!

  3. Tre

    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!

  4. Carolyn

    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!

  5. 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.

  6. 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!

  7. Hannah

    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.

      • Hannah

        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).

  8. Jim @ MSW

    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 😉

  9. Mark

    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!

  10. 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!

  11. 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!

  12. 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!

  13. 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.

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