From Broadway to Business and Back: One Man’s Journey to Debt Freedom and Career Fulfillment

Ryan PortraitTotal Debt Paid Off: $30,000
Months using ReadyForZero: 20
Accounts paid off: 5 of 5

“I’d gotten into credit card debt because I wasn’t being a very good manager of my money. ReadyForZero helped me to see there was a finish line.”

Think back for a moment to when you were a child. Do you remember what you wanted to be when you grew up? Perhaps you wanted to be a firefighter, a ballerina, or a famous musician. One thing is certain, when we’re kids, we tend to dream big.

As we grow older, our dreams morph as our personalities and expectations for our futures evolve. But for some, the dream remains the same forever. Now imagine if you were one of those people…but on the first day of college you’re given the following statistic:

Less than 1% of people in your profession “make it.” In other words, you have a less than 1% chance of earning a living doing what you love.

Talk about a punch to the gut. What would you do? If you’re like our most recent success profile, Ryan, you surge through the uncertain future in pursuit of your passion.


The road to our dreams isn’t always easy though – and Ryan’s path is no exception. He’s faced career upswings and downturns and multiple bouts with debt; but he has come out on the other side with two successful careers and a bright financial future ahead. Find out how Ryan was able to achieve his dreams and how the path to debt freedom helped him get there!

First Foray Into Adulthood – and Debt

Just like with momentous events in history, many people remember exactly how their journey with debt began. For Ryan, it all started with an insatiable love for music.

“I remember distinctly where my debt started. I was in Chicago waiting tables and it was the first time I had a money job… I would go to [Blockbuster Music] after almost every shift and just listen to music – hundreds of CDs – and I just spent all my money. I pretty soon had to start putting it on my credit card then that sort of spiraled into other things. I had this credit card, which was new to me,  and ironically that felt like freedom. Little did I know it was the beginning of sort of putting me into jail. It was a hard life lesson but I’m better for it now.”

Ryan wasn’t the first collegiate or post-collegiate youth to be fooled by the “freedom” of credit cards and he certainly won’t be the last. Credit card companies are known for marketing to young adults who can be lured by the promise of access to credit by speaking to them in their own language. In Ryan’s case, while the debt didn’t come until after college, the first foray into a credit card came in the form of a specifically branded credit card:

“Well it’s interesting, the credit card that got me. I grew up in Michigan, I was a huge University of Michigan fan, so the credit card company offered a card that had a picture of the stadium on the card. It was a University of Michigan American Express. That to me was the coolest thing ever. Now I look at it as just a trick that the credit card companies do to get you to sign up for a line of credit.”

Luckily, Ryan came to the realization that he needed to eliminate his debt and change his habits. However, a turbulent career in show business led to more changes.

Les Miserables…The Musical, The Career Change

In 2001, Ryan came back from a tour of Les Miserables and started interviewing for restaurant jobs to pay the bills until his next show or tour. It was then that he realized he was going down a path he didn’t want to sustain: auditions → show → more auditions and work as a bartender → rinse and repeat. As much as he wanted to be in “the business”, he no longer wanted that lifestyle.

So he took a break and, during that time, began helping friends with their computers. What started out as very simple tasks eventually turned into a legitimate business. Eleven years later, he’s now running a Macintosh and PC support company that has become so successful that he was forced into a longer break from acting to run the company.

Ryan at work-12

Now, Ryan is serving a “dual life” of business owner by day and actor by night. He’s currently on a national Broadway tour of Evita that has him on a rigorous schedule of eight shows a week while working full time during the day Monday-Friday. This is Ryan’s first foray back into acting after years of focusing on his business; and an important factor of being able to handle the schedule is the mental freedom of having become debt-free.

Getting Debt Under Control

Ryan’s debt started because of a bad habit – but much of the reason it continued was because of a fast-paced lifestyle. Running a business and living in the city that never sleeps left Ryan feeling like he couldn’t track his finances at all. That’s when he found ReadyForZero.

Ryan had already been in and out of debt once before when he found ReadyForZero and he knew that the simplicity could be the key for him to reach success permanently this time.

“I’d gotten into credit card debt because I wasn’t being a very good manager of my money. ReadyForZero helped me to see there was a finish line. It was like having a personal assistant just focused on, ‘Hey, you have got to pay this off this month or put money toward this account this month’. I would ask different people, ‘Should I pay off the highest interest first or the lowest amount first?’ Everyone had a different answer. Whether it was the right way or the wrong way if there is one, it was nice to have something simple that said, ‘try it this way’.”

This simplicity gave Ryan the gusto he needed to get moving on his debt payoff plan, but he knew it was going to take more than just that to help him reach final debt freedom. Ryan decided to approach his debt the way a recovering addict would – that he had bad habits that lurked in the background and could always come back. He knew he needed a plan to ensure that these habits never took his life over again.

Seeking additional help, Ryan reached out to a financial advisor: SFmoneycoach. She taught him about something called the periodic savings account, which he fought her tooth and nail on in the beginning. Over time he found that this kept him from swiping his credit card when an unexpected expense arose.

How it works is, by putting away a small amount in your periodic savings account per week, you’ll build up a fund over time that will be used to handle expenses that catch you by surprise, but that you don’t want to take out of your emergency fund:

“It’s designed to be used for those months when you have those unexpected purchases like you go to the concert or you really want to buy this suit or something but you didn’t budget for it. So you pull it out of the periodic savings, which you’re regularly putting money into. She said if you don’t do that, what you’re going to do is you’re going to put it on your credit card and you’ll say I’m going to pay it off next month. Then you’ll have another unexpected thing happen next month and you won’t be able to pay off this purchase.

I didn’t believe her. I said ‘I think you’re wrong but I’m going to trust you’, meaning I said I should be putting my money towards paying off my debt. She was right. It was one of those where I learned the hard way and I didn’t get back into debt because I had the periodic savings account. I had this plan, again that was the plan. If I do come across that thing that I want to buy I have the money to do it outside of my normal checking account and I don’t have to use my credit card.”

The simplicity of ReadyForZero’s plan and the periodic savings account helped Ryan get on track to get rid of his debt for good. But he had two more things that helped him stay on track: visual tools and accountability:

“ReadyForZero kept telling me, ‘here’s how much money you could save if you pay this one off’. There were a lot of little simple things, and the interesting thing was all of these things I could have done on my own, but I feel like we all have 50 things we could all do on our own but we don’t because we have life to live.

I also set up accountability partners and it was one of those things that really worked. One of those where I got the email from my mom and my best friend saying, ‘hey congratulations’, or ‘you’re doing a great job.’ That was nice. It was like someone patted me on the back. It almost spurred me to say I want to put more money towards paying this off because there were a lot of positive feedback.”

The simplicity, the plan, the accountability…all of these things helped Ryan reach an incredible goal: $30,000 in credit card debt paid in full. As if that weren’t great enough, this success has spurred on a momentum to achieve even more.

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Living the Dream – in Life After Debt

We asked Ryan if paying off debt helped him get back into acting – and it turns out it did that and then some:

“Well, you know, it’s interesting. I don’t think until right now I really linked up a lot of things in my life. I think there was a definitely change in my life when I got out of debt, and I’m sure it did spur me toward going back to auditioning, but it spurred me toward a lot of things like getting back in shape. That is a good feeling and I felt better about myself. Going out with friends more often, taking trips, there was definitely a sense of freedom. It was like I was getting out of jail and I thought, ‘Okay, I can live my life now’. But it wasn’t conscious. I didn’t think that until you just mentioned it…but I was like ‘wow’, there were a lot of things that came since I got out of debt and I can only imagine they’re all connected to the sense of the burden was gone.”


Of course, Ryan doesn’t intend to stop there! Besides pursuing two careers that he loves, he’s also focused on improving his credit score and saving for retirement. Before he paid off his debt, he never thought about saving for retirement but now he wants to build his wealth and live a life of financial freedom. And, of course,  he doesn’t want to forget the lessons learned…

“I still think I’m a recovering addict…So right now the goal is how to get my credit score higher and to start saving for retirement, then eventually start looking at investing outside of retirement funds on top of continuing to become more healthy with money.”

Given the amount of drive Ryan exhibits, we’re pretty sure he’ll get exactly what he wants in his future. From that first day of college being told only 1% of his peers will make it to achieving a successful acting career and a successful business, it seems like there’s nothing Ryan can’t do!

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  • Billiam

    This story resonates with me.

    Hits home:

    Back in the CD era I used to buy music almost every paycheck.

    I bounced between fulltime and part-time jobs trying to make a living while doing short tours with a band.

    Looking back:

    I think instead of being told discouraging career statistics by advisors during college, arts focused people need to be told and retold about the long lasting implications of not getting their personal finances off to a good start. Regrets don’t come from career choices as much as from debt and savings choices.

    • Shannon_ReadyForZero

      That’s such a good point! A lot more people could chase their dreams early on if they were coached on how to create a solid financial picture! Thanks for sharing your story with us :).

  • This story sounds familiar… 🙂 Scheduled to go on tour this fall again, don’t know how I’m gonna keep up with my business during that time. But now I have some inspiration!

    • Shannon_ReadyForZero

      You can do it, Stefanie! 🙂 What show are you going on tour with?