How Side Hustles Changed My Financial Life

Who doesn’t love side hustles? Millennials are the side hustle generation, thanks to wage stagnation and the Great Recession. They give us breathing room in our budget, allow us to pay down debt, build our savings, or even just make rent on time.

Here’s a fun fact about me: I’ve never held a traditional job. I have never worked a 9-5. I’ve never been salaried, or even a full-time employee. My post-college work career has exclusively consisted of internships, both paid and unpaid, and side hustles.

I’ve worked as a social media manager, a caterer, a gym receptionist, a waitress, a nanny, a high school lacrosse coach, a van driver, a content research manager, a non-profit Development Director and a freelancer writer. At my peak, I worked five jobs at the same time. Right now, I work three jobs: freelance writing, CEO of Bravely, and catering.

Side Hustles Were a Game Changer

While side hustles have been my life since I was 23, they didn’t always work for me. I needed to learn how to use money as a tool before I could do anything with it. That lesson smacked me in the face when I was 26, making $900 a month, and carrying tens of thousands in student loan debt.  I didn’t make over $30,000 until 2015.

In 2014, I realized that if I didn’t change what I was doing, I would stay in that low-income cycle forever. I would carry my debt until I died. I would never make more than $25,000 a year. That thought scared me to my core, and I freaked out.

My situation was atypical- it wasn’t simply a matter of re-routing money I was already earning. It wasn’t a matter of cutting back on my over the top spending. It was a matter of making more money and using my money to make my life better. 

I changed nearly everything in my life in pursuit of becoming debt free and beginning to build wealth for myself.

I started tracking my spending with budgeting. 

I focused on building my emergency fund from $1,000 to $2,000.

But the thing that had the most impact was the way I used my side hustles.

Instead of seeing my lack of a 9-5 as a failure, I saw it as an opportunity. My flexible schedule meant I could work different jobs at any time, and in any industry I wanted. I could work over time, and I could work as much as I wanted.

Make More Money

Realizing that, the first thing I did was ask for a raise at my catering job. When I had my financial awakening (or crisis, whatever), it was July 2014. I was working about 18 hours a week as a receptionist and caterer. I’d been catering for nine months and hadn’t received a single raise. I asked for $1 more via email and got it. That immediately impacted my finances.

The second thing I did was set out to find more work. By September, I had picked up a part-time job at a new non-profit. I worked ten hours a week for them at $11 an hour. I also started working way more for my catering company.

My new average was about 32 hours a week across three jobs.

By January of 2015, I’d paid off $2,000 worth of debt. I knew I needed to keep increasing my income to keep paying off the debt fast.

I replied to an ad on Craigslist looking for social media help and picked up 10 hours a month at $12 an hour as a freelancer.

In January I was also promoted at my catering company. I was made an event lead, which lead to a $2.50 raise and more responsibility. Spring is a busy time for catering, so I was thrilled to get the raise. I knew a lot of hours would be coming my way starting in March. My new pay raise meant more debt to pay off.

January 2015 was also the month I got my first paid writing assignment. I made $10 off an article for Red Debted Stepchild. My article was picked up by Rockstar Finance and generated a lot of views for the site. I used that information to pitch myself as a staff writer to Cat Alford, the owner of the site. She hired me for two articles a month at $12.50.

I started blogging about my debt payoff journey (which was the BEST decision I could have made) and wrote more freelance articles for pay. Blogging led to getting freelance writing jobs, speaking gigs, and provided a platform to showcase my writing abilities.

Looking back, starting a blog to track my own debt payoff journey was the single best investment I have ever made. I eventually sold that blog to get part of the start up capital for Bravely, which has gone from a side hustle to my full time, six figure career.

By the way: freelancing can be great side hustle money, but make sure you’re tracking your income. I use Freshbooks to send invoices and track income. You need to pay taxes on your freelance income and I didn’t know that when I started writing!

In February I started working as a lacrosse coach. I was paid a stipend of $5,000 for three and a half months of work.

At this point, I was working five jobs: catering, coaching, writing, social media management, and working for the non-profit. 

More Money, More Debt Payoff

I regularly worked seven days a week, and I was exhausted all the time. But my income had risen dramatically. I had months where I paid off $4,000 in student loan debt. All my side hustles allowed me to send thousands of dollars to my debt each month. It felt incredible to watch the balance drop quickly.

On June 5th, 2015 I made my last debt payment. Less than a year from the lowest point in my life, I had paid off all my debt and more than doubled my income. Thanks to side hustles, I broke free of my low-income cycle!

I kept working four jobs through the end of 2015 and was able to save $5,500 in my IRA account. That was the first serious money I had ever put away for the future, and it felt amazing. I finally felt like I was standing in a place of financial security.

I still catered throughout 2018 for two reasons: the catering paycheck came every two weeks, and I used the money for savings.

Some of my early freelance paychecks came 30-40 days after I invoice the clients. With such a long time between doing the work and getting paid, saving is sometimes a challenge. My catering income allowed me to sock money away for travel and retirement every two weeks.

I also formally started Bravely in 2017, but it was very much a small business for the first two years. It profited each month, but not enough to save or invest. I wasn’t willing to sacrifice doing those two things so catering allowed me to work on Bravely AND invest.

After all my side hustling, I can honestly say that starting my own business was crucial to changing my whole financial life. It started as a side hustle that helped me pay off debt, then helped me save more money, and now my business is a global six figure business.

My finances are looking good, but my new focus is retirement savings. I’d like to have $50,000 saved by the time I’m 30, which will be a little bit of a stretch.

Side hustles changed my financial life. They continue to help me achieve financial milestones at a faster rate than I would without them. Tell me what your side hustle is, and how it changed your financial life!

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