Is hustling actually a good thing?

This week’s edition of Wishful Working was written by my friend Stephanie Mickelson of The Simple Freelancer. You can find my guest post on her newsletter here: Not All Pivots Are Permanent. Thanks for sharing your thoughts, Stephanie!

Hello Wishful Working readers! I’m Stephanie, a freelance writer, lover of hot coffee with heavy cream, cozy mysteries, and funny shows. I also run The Simple Freelancer over on Substack where I offer simple tips for freelance success. I’m also a practicing perfectionist and workaholic in the best way.

When Kara and I talked about doing a newsletter swap, she suggested that I write about times that hustling can be good, and I jumped at the chance. Kara is one of my earliest freelance friends from way back in the Twitter days. I’m so happy that we’ve kept in touch over the last few years and even making the switch to LinkedIn around the same time (come say hi!)

I’ve been working for almost as long as I remember. When I was a kid, I started a club where we did chores for the neighbors and then used the money to give them anonymous gifts. When I got a little older, I mowed lawns, had a paper route, and helped my aunt with her landscaping business. At 16, I immediately got a job at a restaurant (which I hated) and then worked at a belt kiosk in the mall and a flower shop (both of which I loved).

Throughout most of my 20s, I had lots of jobs at once. Often three or four. For quite awhile, I worked as a reading teacher full-time and also worked at three restaurants. Teaching high school English was one of my easiest jobs, mostly because it was my only one…for the most part. But when my husband and I really put our heads down to pay off my student loan debt, I taught, worked at the after-school program, and milked cows. One summer, the school paid me $13 an hour to, I kid you not, paint a chainlink fence silver.

Despite all this, I’ve never worried about “hustle-culture” or ended up burnt out. I just really like to work.

I also love to hang out with my family, do puzzles, eat snacks and watch a show, read, do escape rooms, and have coffee chats.

I understand, however, that for many, work is separate from the things they truly enjoy. I also understand that there are times to work and times to rest, and that living in perpetual hustle, while it can be invigorating, isn’t a sustainable way to live forever.

So I’m here to break down three times when hustling is a very good thing.

You’re working towards a short-term goal

When my husband and I were paying off my student loans, we both worked our behinds off. I was a full-time English teacher and then worked at the elementary after-school program. We both milked cows at a local farm. My husband was also working multiple jobs. Over the first two years we worked on paying that debt off, we paid off about $20,000 of the total $60,000. In the last year and a half, when we were pushing, we paid off the remaining $40,000.

If there’s a short-term goal you’re working towards achieving, getting deep into the hustle can help you meet that goal faster. Our initial goal was to pay off my loans in five years, and we ended up doing it in three and a half.

You’re in transition

Sometimes, when you’re transitioning from one position or one job to another, there’s some overlap or additional tasks to wrap up. For a period when I first moved to Virginia, I worked at a daycare, and it was awful. I quickly realized that I needed to find a different job, so I got a job as a bartender, but that wasn’t going to cover all of my expenses. Then, I convinced a new friend to hire me to work as his assistant in his kitchen remodeling business (you can listen to the story here).

As soon as he hired me, I put in my two weeks’ notice at the daycare but wanted to start with him right away. For those two weeks, I worked with him from 7 am to 11 am, went to the daycare from noon to 6 pm, and then hustled to the bar and worked until 11 pm. I was tired, sure, but I also knew it was for a very short time and would help the transition.

You love it

I genuinely love working. Pre-kids, I almost always had multiple jobs that included (but weren’t limited to) a confectioner’s assistant at a popcorn factory, a car salesman at CarMax, a receptionist at a modeling agency, a server, a bartender, a reading specialist at a daycare, a landscaper, a construction assistant, a cow-milker, and more.

Even when I was a teacher, I was in the classroom and on a lot of committees. I was also a co-advisor for Prom and Student Council. I even toyed with taking on the drama class, but then we had our son, and I decided not to.

Working has always been a hobby of sorts, especially when a new job means learning a new skill and taking on a new challenge. When I was at the popcorn factory, I revolutionized their way of making cotton candy without waste. I also nearly blinded myself with a piece of fudge. For me, work is exhilarating and I find a lot of fun in the hustle.

Out of Office (Stephanie’s Version)

What I’m doing when I’m not working

• As I write this, I’m watching Harry Potter and the Chamber of Secrets with my family. I’ve been reading Harry Potter to them at bedtime, and we just finished the second one. It’s been so much fun introducing it to them!

• I just launched the Freelance Foundations course! (This doesn’t count as work!) My client work slowed way down, so I spent some time pulling together lots of things I’ve learned over the last six years of freelancing. More about the course below!

• My friends and I love escape rooms, and we do at least one every year. We did the Halloween one in town a couple of weeks ago. It’s at an old house turned museum, and the Halloween one is set up in the basement. 

When you buy the Freelance Foundations course ($79), you’ll get:

✅ 6 modules that each focus on a different aspect of starting and growing a freelance writing business
📝Activities along the way to help you focus or refine your mindset, niche, tools, and more
💭A Notion Course Companion where you can do the course activities
🎯An income tracking spreadsheet that totals monthly and yearly income
❔3 opportunities to join a Q&A session where I’ll answer any questions you have about the course or freelance writing in general

If you want to check it out before you buy the entire course, you can get Module 1: The Foundation for FREE!

Stephanie Mickelson is a freelance writer focused on home goods, home tech, home improvement, beauty, and lifestyle. She writes The Simple Freelancer and publishes twice a week on Substack. When she’s not writing, she’s probably playing cards with her kids, drinking coffee on the porch with her husband, or eating a snack and watching a show.