Thinking of a Creative Career? Learn How This Millennial Actress Became a Money Expert

Michelle Jackson — First Jobs

Stefanie O’Connell is a former actress turned millennial personal finance expert and author of The Broke and Beautiful Life. She’s been featured in Forbes, The Wall Street Journal, and the Today Show spreading her #BreakingBroke movement and sharing insights from her days as a globetrotting, struggling artist.

I decided to speak with Stefanie about her transition from actress to personal finance maven because I was completely fascinated by how she managed to change her financial life while living in New York City—one of the most expensive cities in the world. I called her up in NYC and got the details about how acting in a rags to riches tale ultimately led to a modern-day financial fairytale.

Michelle: What is it that you do now? We’ll start there and work backwards.

Stefanie: I write about millennial money from paying down debt, to earning more, to growing your wealth longterm.

Michelle: And how did you get into that? How did your first job influence your current career?

Stefanie: My first job out of college was as an actor on the international tour of Cinderella, so, not about money at all. But it had a huge influence on [why] I ended up writing about money.

I found out that my journey as an artist trying to figure out my money was kind of commonplace for all young people trying to figure out their money in the post-recession economy. My experience really resonated with them in a relatable and digestible [way], as opposed to stuffy advice you can’t really connect to. So that’s kind of how that all happened. I know that’s not a traditional transition, but it ended up being the best of both worlds.

Michelle: So, in terms of money and creatives, walk me through it.

Stefanie: It was 2008. It was maybe the worst timing ever because I had graduated that summer and two weeks later I was on a plane to the Philippines for the show. I had contracts for the year that were supposed to extend and be open-ended, but by December the producers had flown out and said, “Actually, we’re going to be sending you home earlier because of the economic crisis.” I wound up being unemployed in January of 2009.

Michelle: When you were doing the tour, what was the pay like?

Stefanie: I made $450 a week and that went through direct deposit. This was actually one of my better jobs [as an actress]. I had consistent income and I had a per diem on top of that. It was great because your money goes a long way when you’re in China and the Philippines and such. I lived exclusively off my per diem and I didn’t spend any of my salary. Even though I was only making $450 dollars a week and it was only a seven-month job, I made over $12,000, so when I came back to New York I had a $12,000 emergency fund.

Michelle: Wow.

Stefanie: And that is what really enabled me to take the time to figure things out when I got back. And why I was super, super, money savvy, because I wanted to make that money last as long as possible and I definitely relied on it. Like when I was babysitting and stuff…it didn’t cover everything, but because I had that buffer from that first job I had a lot more flexibility.

Michelle: What happened next?

Stefanie: So, the next step was auditioning to get a job and also hustling to make ends meet. When you’re an actor you’re always in this precarious balance. You’re pursuing what you want to do—and hopefully for money—but in the meantime, you can’t ignore the financial reality of your day-to-day. To satisfy that demand you have to hustle, and so I was hustling. I worked at a restaurant. I was a babysitter. I was a personal assistant. Basically, anything that enabled that flexibility to leave at a moment’s notice so that I could do a show if I got one, but also paid enough to pay my bills.

The problem is, traditionally those [side] jobs aren’t exactly high-paying. That said, if I knew then what I know now I would have been a lot more strategic. There’s so much that you can now do online. For example, if I had been a virtual assistant … or even Pinterest image designer, that’s what I wish I would have been doing then.

““If you always make the assumption the price you see isn’t the only price available, you’re going to find there are a lot of great savings to be had.””

Michelle: What’s the number one money lesson you learned [from your acting days]?

Stefanie: I basically learned how to challenge every single expense. I think there is this thing where we accept that something costs what it costs and that it just is what it is. [But] for the most part, you can negotiate, or find an alternative, or hack the cost of just about anything.

Because I was determined to not touch my salary and only live on my per diem, I was always on the lookout for deals. We had four days off from [Cinderella] when we were in the Philippines and there was this island called Boracay that I wanted to visit from Manila. I had found this super cheap flight and everything there was going to be super cheap, it just was the hotel that was expensive.

So, I’m looking for a way to hack it and I finally found this expat deal. Because I was living in Manila for two months I was actually able to [be considered an expat] and pay 50 percent off. But, only because I took the time to look and challenge it. If you always make the assumption the price you see isn’t the only price available, you’re going to find there are a lot of great savings to be had.

““…Even if you have a traditional 9 to 5 job, if you’re 100 percent reliant on that one income stream, you’re not diversified and you’re putting yourself in jeopardy.””

Michelle: What’s the hardest financial lesson that you learned during that time?

Stefanie: That I had no security. Being reliant on a single income stream is dangerous. And I know that, yeah, I was an actor and it was a little bit different …But even if you have a traditional 9 to 5 job, if you’re 100 percent reliant on that one income stream, you’re not diversified and you’re putting yourself in jeopardy. I wish I had started thinking earlier about ways of cultivating additional income streams so that I was never going to be with zero coming in.

Michelle: What skills did you take from that first job that you still use today?

Stefanie: I would say those skills you learn as a performer and you implement by speaking in public, by connecting with other people, by learning to improvise, learning to manage in the moment when things go wrong, are all invaluable in any field—and what I use in my career today.

It’s unfortunate that people kind of cast aside the skills of artists because they are actually very highly valued, just not within the context of a traditional artist’s job. If you take public speaking off the stage and you bring it to finance, all of the sudden it’s a highly valuable skill.

““There was something really empowering about this idea of managing money because my life was so outside of my control.” ”

Michelle: How did you go from acting to what you do now?

Stefanie: I was about four years into my acting career when I was given my first personal finance books…. Suze Orman; The Millionaire Mind; Rich Dad, Poor Dad.

There was something really empowering about this idea of managing money because my life was so outside of my control. When you’re working in a creative field, you kind of feel like you’re always at the mercy of when someone is going to give you an opportunity.

While my income fluctuated a lot, I could control how I spent my money. I started tracking every single penny in spreadsheets and that’s a practice that I continue to this day.

As I did that, I started to feel more and more empowered. I was like, “this is an amazing feeling to have as someone who typically feels so out of control in her life.” I needed to share this with other creative people that I knew, other New Yorkers, other young people, because I feel like there’s so many of us with that sense of feeling out of control.

I started a blog just to kind of chronicle that experience, and in doing so I was exposed to so many other personal stories of people going through their financial journeys, and that enabled me to learn even more.

I had been focusing on the spending side of my life and finding empowerment through that, but then once I started reading blogs I saw how much opportunity there was to take control of the income side of my life: cultivating those additional income streams, negotiating for higher rates, and being aggressive about my earnings. By sharing those stories and by sharing my own story of financial transformation, not only did I build a profitable business—I built an entire lifestyle that I love more than anything I ever did when I was performing full time.