How many Second Jobs or Side Hustles are too many?

I’m not sure!

Over the past few years, I’ve ebbed and flowed in my desire for side hustles vs. second jobs, and back again. I’ve decided to pull back hours on one of my second jobs, to pick up more side hustle hours, to now picking up another second or third job or fifth place of work or maybe a 3rd side hustle? I don’t even know anymore, I’m losing count!

A decade ago, we hit our hardest financial struggle as a married couple, 2 1/2 years into marriage. This month, ten years ago, we were facing unemployment and the end of our contracts without anything in sight. The economy tanked, it hit our careers hard, and we were at a loss as to what was going to happen to us. This was our first major meltdown financially, which we managed to pick ourselves up, dust ourselves off and get down to work with a lot of luck, spit, and duct tape.

From there, we hit hard times once more about a year and half later, which drove us both to pursue not just one main source of income each, but side hustles as well. We considered hobbies we could turn into income, helping others in various ways for pay, or anything we could come up with to increase our income, savings, and emergency funds for another rainy day to come. We sold a ton of “stuff” and detached ourselves from things. We never wanted to be in dire straights again, surviving on the cheapest of pastas for months.

At this point, we’ve never set down those side hustles or second jobs that we’ve collected over the years. I feel as though Chris and I get fulfillment from having more than one place of “work” and also find the financial advantages useful for our goals.

We love that our children see us hustling and working for all sorts of projects on a regular basis and hope it instills a bit of “hustle” in them as well. Our oldest loves to clean houses for money with his vacuum collection… he loves hustling the neighbors to schedule a cleaning! All the older ladies love him for cleaning their vacuums, showing them how to use them, and of course, cleaning those hard to reach places with the crevice tools!

We’ve never stopped looking for more opportunities to increase our income in the past 8 years, and I doubt we’ll ever stop. It’s been an increasing part of who we are and just what we do. We enjoy working, we enjoy a variety of sources of income and it takes the pressure off the main source when things may get tough or stressful to deal with at work.

As of now, when I stop to consider all avenues for our income it’s astonishing. In a short decade, we went from single job earners, with Chris in a long-term sub position without concrete income after six months… to both being full-time employed, in addition to a myriad of side hustles or second or third or fourth or fifth jobs!

Chris works his full-time job, a second job as an adjunct college professor at a large university, and announces high school sports games as he did years ago. In addition, he announces our summer county fair annually, and he still keeps a professional podcast going (the work he puts in is amazing!). PLUS he edits several other professional podcasts on a weekly basis. How he gets it all done and spends time with his family sometimes is impressive! Not to mention, he loves doing home improvement projects and builds things out of wood beautifully!

To that count, he has 1 full-time job, 1 second (but like a full-time) job, and 3-5 side hustles…

I work my full-time job, a second local college adjunct librarian job, while also side hustling for not one, but now two online remote positions online as of last fall. In addition, this month I landed a THIRD place of work I’ve wanted to work for for a number of years 🙂 I’m super excited to be in the role of a college adjunct librarian position at the same large university as Chris and even better, it’s remote!

To Chris’ count, add that I have 1 full-time job, 2 second jobs (though cutting hours at one to add more of the other), and 2-3 side hustles…

In total, we have over 2 full-time jobs, 3 second/third/fourth jobs, 5-8 side hustles at any given time during the week. Is that a lot?

In my entire career, since working as of the age of 16, I don’t believe I’ve ever had one year where I didn’t have more than one W2 arrive for tax season. Typically, up until 2008, it was because of job changes within those years, but now it’s usually just additions to the growing number of second, third, fourth, or side hustles mailing me W2 or 1099 forms.

I wonder at times where it’ll all settle. Will we use our second or third jobs to parlay those into a second or third careers in a different area, or will we keep those for fun side hustles as long as we enjoy them? I feel like I’ve worked toward building multiple sources of income for two reasons.

The first reason is obviously to avoid the financial walls we ran into during the last major recession. We don’t want to go back there, but if we had, we’re better prepared to handle it this time. We aren’t truly attached to our stuff (we sold a TON of it back then – I still miss our Nintendo Wii!). We know we can make it through and just sell off what we don’t need to keep afloat beyond our emergency plans.

Secondly, having another income outside of our main source of income, for me at least, takes the pressure off of that first role. While the income is larger in my full-time job, and the source of health insurance is major, having something to fall to in times of distress provides a small peace of mind. This third job I’m adding to the mix has the opportunity to replace a good portion of my main source of income if something were to change.

I’m so grateful that we’ve hustled our way to this place. Our main careers have grown with our second jobs in more prestigious positions, albeit part-time for now, and our side hustles allow us to enjoy helping others in new ways and learning new things while making some extra income.

We’re always learning and growing, which is the point for us. Lifelong learning, growth, hustlin’, and seeing what we can do. We still manage to cook home cooked meals, spend A LOT of time with our boys, and enjoy our summers together. I’m interested to see how this new role will fit into the mix, but I’m excited at the same time. I may cut back on my other remote hours, but for now it’s full steam ahead.

And all of this is why… I workout at 5am. If I didn’t make that a priority, the rest of the day was getting ahead of me. Now that I get “me” done first, I am so relaxed to handle all that’s thrown my way, even spending a day in the ER with my Mom over the weekend. That was scary, but everything is OK.

Lent is a beautiful season of reflection for me.

During this time of year we’ve battled some of our hardest times over the 17 years we’ve known each other. Chris and I met in March 2003, and started dating in April that year. We both knew from the start we made a great team, and here we are 12 years into marriage still rocking high fives, silliness in our every day, and hustling for ourselves, and our family.

I take every early spring season to reflect back on our years after I’ve survived the darkness winter. To renew and reflect on how far we’ve come, and where we’d like to go. I’d love to have closer relationships with some family and friends in my life. In due time, warm spring will be here and we’re gearing up for a fun summer ahead! It’s almost scooter season 🙂

How many sources of income do you have? If it’s just one, do you have a desire to add a little something on the side?