Lifestyle,  Money-Savings

Financial Freedom: My Debt-Free Story


Debt is a subject close to my heart, knowing that a staggering 40 million Americans are juggling student loans. The Wall Street Journal reports that approximately 250,000 Americans with student debt file for bankruptcy each year, breaking my heart and exposing the flaws in a system that favors privilege.

In many ways, I’ve had some privilege. Born into a lower-middle-class family that climbed to the middle class, I was told the usual tale: get a degree, get a job, and watch your loans disappear.


Financial Freedom: My Debt-Free Story

As many millennials know, that didn’t play out for a lot of us. After my degree, I found myself in a minimum-wage job for the next 3 years. Even after I moved to Seattle, 12 years ago, my loan balance didn’t shrink — it grew, thanks to interest.

You may be thinking “why didn’t you read the fine print?” or “what a rookie mistake” and that’s because I was barely 18 when I signed my loans. Little did I know, those debts would tag along for the next 17 years.

Emotional and Financial Challenges

There’s this feeling of complete and utter dismay when you hit rock bottom. For me, I had to have gallbladder surgery. At the time, there was exactly $7.14 in my checking account and a savings account of exactly $100.

It was terrifying.

I didn’t know how I was going to pay off surgery, even with part-time medical insurance, nevertheless groceries. Looking back, I could have called home but I was so embarrassed and scared of being criticized for my miscare of money. By this point, I had gotten my first credit card – one of my biggest mistakes.

Please note that I’m not using the term “regret”. I don’t regret any of the decisions I’ve made leading up to my current life. I am proud of the woman I am today and I wouldn’t be her without these lessons.

When things got worse, I didn’t call home. Instead, I eventually broke down in tears and called my cousin in Virginia. That led me to leave Florida for a job that paid a little more, but the decision wasn’t easy. Especially surrounded by people from wealthier backgrounds, I began to grasp the reality of the poverty gap. One co-worker had parents who bought her a 2-bedroom condo for her minimum-wage job. My privilege was much smaller but impactful – a fully paid pre-owned car as a graduation gift. Different forms of privilege. Right?

Motivations and Promises

I found myself stuck in a recurring debt cycle. Each month, I’d start and end with the same financial weight – $500 in the red. I’d justify purchases with excuses until the day I took a hard look at my overall loan situation. That’s when I decided to start a path to financial independence. I kept seeing glimpses of myself without student loans and I couldn’t get it out of my head.

The one thing I was good at was “tricking” myself into putting a little cash away for a rainy day. I noticed that if I had cash, I wouldn’t spend it. So, I began stashing physical cash – a sort of modern envelope system. If you’re unfamiliar, many people use this method, including my mom when I was little. She also was an avid couponer. I figured if she could do that for a family of 6 – I could do that for just myself.

When my last job came with a 35% pay increase, I created a strict structured plan and spent the next three and a half years making intentional payments pushing myself to the limits to pay off every dime. I even set up a challenge to make an extra $200 every month just to see if it would motivate me enough to hit my goals faster – it did. I lived off of next to nothing outside of my means during those years. I worked so hard and said “no” to 90% of the people who asked me to go out to dinner or happy hour, etc.

Why Am I Sharing This Journey on My Blog?

Debt’s Loneliness and Impact on Self-Worth

Debt is painstakingly lonely. It’s brutal and it makes you feel inadequate. Inhuman, almost. I promise to write another blog post all about this in the coming months.

Societal Pressures vs. True Needs

Often people overlook the struggles you face with debt, while simultaneously placing undue emphasis on material possessions, like the latest Stanley Cup – which, by the way, isn’t a necessity. Trust me, you’ve got plenty of water bottles.

I understand the allure of staying trendy and fashionable, and there’s nothing wrong with that. However, it’s essential to recognize that trends are transient. Stanley Cups may lose their allure as they become more common, making way for the next fashionable water bottle. The truth is, you’ll likely feel left behind regardless of the trend. Embracing what you already have can be surprisingly fulfilling.

As a little secret, a pasta sauce or mason jar serves as an excellent iced coffee cup. It’s a cost-effective option, and the jar is both BPA-free and FDA-approved. Sometimes the simplest choices are how you can stand out from the crowd.

Guidance for the Next Generation

I also want to share this story because I think it’s supremely important for the next generation to understand what they are walking into. There are a lot of things I wish I had done differently. One that I go back and forth on is college. There’s a part of me that wishes I’d have waited to go until I knew what I wanted to do in my professional career. Especially because I majored in a degree I do not use. The best thing I ever did for myself was accept an internship at Disney World while I was in college. I learned the value of hard work and customer service. That has gotten me further in life than my degree.

Am I saying not to go to college? No – not at all. My degree helped vet me for every interview I got but what sold them on the job was me. I’m also suggesting that college isn’t for everyone and it’s perfectly okay to embark on a non-traditional college experience. You can get an amazing education by going to community college and reading about your interests in your spare time.


I want you to know that if you are struggling with paying off your debts – you are not alone. It’s one of the most infuriating experiences to watch a huge chunk of your paycheck go to a bank but the day you make your last payment will be one of the best days of your life.

The next post in this debt-free series is all about budgeting my way out of debt.

If you’re interested in learning more about my debt-free journey, this series, and also travel tips and tricks – please consider joining my email list! My goal this year is to grow it and also send out personalized emails every other week with insights on my travels, personal stories, and essentials!

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Wishing you th best in your financial independence journey! 💕

Love Alli // On the Trip side Signature

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2 Comments

  • Amanda

    oh my friend, what a great and important post! i hate the way we people are so averse to talking about money – it’s so isolating! excited for the rest of this series!

    • Alli B

      Eeep! Thank you for reading, my friend. 💕 That means so much to me. I will definitely keep up with the series. I’m aiming for the first Monday of every month!