From debt to over 20 credit cards: the story of my personal finance journey

Feb 14, 2020

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While I grew up loving travel, points and miles, I wasn’t always financially secure enough to afford to travel. Even though I now hold over 20 credit cards in my wallet and frequently travel, I once had mounting credit card debt.

The good thing about finances is that you can almost always fix or improve yours with the right steps.  I wanted to take a moment to share my journey to financial independence. Stay tuned for more articles on personal finance coming soon with advice and steps on how to handle your travel and finances at every stage in life — whether you’re a student, business traveler, home owner, about to get married, raising a family or nearing retirement.

The beginning: Getting into debt

My 20s were a wild time for my finances. When I was about 20, I started by getting my first credit card through the University of Pittsburgh (my alma mater) which offered zero rewards, except for a free t-shirt. I quickly learned that the allure of using credit was addictive and I ended up in debt. This was a major mistake that took me several years to fix.

After I graduated from college, I moved to New York. Confronted with the realities of living in a very expensive city on an entry-level salary, I found it near-impossible to pay rent, live comfortably and pay off my credit card debt — not to mention student loans. Looking back, getting into debt while still in school was a mistake that prevented me from having a fresh start after college.

Another huge mistake I made was switching houses during my college years without changing my address with my cell phone company. I wasn’t aware of some bills as they were sent to my previous home, therefore, I never paid them. This resulted in a hard ding on my credit score for years following.

While that last mistake may seem like a silly one, it didn’t just disappear. In fact, no credit mistakes can suddenly go away. So don’t avoid dealing with credit issues and try your best to keep track of all the little things. Nowadays, with online bill payment options it’s much easier. If you forget to change your mailing address, you can still pay that cell phone bill online.

Although my first credit card wasn’t even a card that earned rewards, it may be tempting for people to get these high-reward cards to earn points and miles. Just remember that if you spend outside of your means, the high interest rates and fees on these premium cards will negate any of the points or rewards earned. Don’t just charge things and expect to figure out the bill later.

If I could give my 20-year-old self some advice, I would have sternly explained to myself that as much as I wanted to go on spring break in college, I shouldn’t have had that ‘you only live once mentality.’  I wish I’d realized I’d have plenty of other options to travel in my life, and that the debt I accrued (which would later be extra-difficult to pay off) would make any extravagant spring break trips later not seem to be worth it.

The middle: Paying off debt and moving forward in my credit journey

In my mid-twenties, I got my act together, getting a job at Morgan Stanley. I was able to get a corporate American Express® Credit Card with a $95 annual fee that earned Membership Rewards®. That’s when my points financial life began to change for the better.

Even though I wasn’t earning a very high salary at Morgan Stanley, being smart about airline and hotel loyalty programs during business travel helped me to maximize spend on my corporate card (especially during the recession).

This led to me earning even more points, as well as hotel and airline elite status. Through earning points on this card, I was suddenly points-rich and able to travel the world.

This is really where The Points Guy began, as I carefully began navigating the credit card points world during a recession. I was the definition of cash-poor, but points-rich.

I did make some positive financial decisions in this period of my life, though. Morgan Stanley had a one-to-one 401K match program, which I put money into. It’s been fun to watch that account slowly grow over time.

(Photo by Wyatt Smith / The Points Guy)
(Photo by Wyatt Smith / The Points Guy)

Moving into my financial future

Now that I have my finances back on track, I invest, max out my 401K and have a financial team I trust. I meet with them twice per year to go over all my finances, especially to predict any changes coming in my life so I know exactly what I need to plan for in the future.

I also invest in smart real estate, but always carefully, as I spent many of my formative years during the recession. I’m always prepared for a rainy day, as I know that markets will not continue to go up and up. Having a balance of stocks, 401K, real estate and wise investments (like start-ups I believe in) is my current and future strategy.

The  most important thing I invest in, though, is myself. I did this when I started The Points Guy and I strongly believe in our parent company, Red Ventures which has helped TPG to grow immensely.

Investing in yourself, especially if you have a truly great idea that you believe in is important. Make sure you have a solid understanding of personal finance and money management before you begin investing in order to best achieve your goals.

I started The Points Guy with a $10 website domain purchase and a few blog posts. Several years later, TPG has turned into something I never could have imagined.

The Points Guy started with a $10 domain purchase and a few blog posts.
The Points Guy started with a $10 domain purchase and a few blog posts.

My best tips for building, fixing and maintaining credit

Building credit is easier than you think, while fixing it is harder than you think. With a lot of phony sites out there promising to fix your credit report, it may seem simple, but there’s really no easy fix. Slowly paying off debt and reestablishing your credit is the best way to go.

There are tools you can use, and you can always dispute anything that seems off about your account, but all of this takes time. Finance is serious, and if you make a mistake, you can’t just expect that banks and credit cards will just let things go.

That being said, usually if it’s a first and honest mistake, contact the company to see if it’s possible to fix things or take them off your report. The main takeaway here is to deal with these problems and don’t just let them sit around and negatively affect your credit.

Maintaining a healthy credit score starts by educating yourself. Start reading about what goes into a healthy credit score, things like paying your bills on time and keeping your balances low. My best suggestion is to always pay your card balance off in full.

For those using corporate or business cards, get those expense reports in early so that you don’t run into issues not getting reimbursed in time to pay your bill in full. If you get hit with interest fees, any rewards earned become less valuable.

Some people think all credit cards are bad and this just isn’t the case. If you are unable to budget or live within your means, they can be bad. But for most, if you can properly budget, credit cards give rewards like points, miles, lounge access, statement credits, free checked baggage, upgrades and more. Besides that, something people often forget about are the added protections credit cards offer.

Credit cards have helped me in more ways than just points and miles -- I've used purchase protection too.
Credit cards have helped me in more ways than just points and miles.


I once bought a Moncler jacket using The Platinum Card® from American Express. Shortly thereafter, I lost the coat in Iceland. Amex totally had my back here and their shopping benefits helped me recoup as much of my loss as possible. And, with so much fraud happening these days, if someone manages to compromise your debit card and drain your bank account, you’re in trouble. Although your bank may reimburse, you might just be stuck without cash for awhile which could be really stressful. With credit cards, most banks handle it without an issue and you’ll be off the hook without forking over any cash.

Bottom Line

When you're credit score is finally high
When your credit score is finally high.

My financial journey has been a crazy one, but I managed to come out on top and with a healthy credit score. I now have over 20 credit cards in my wallet and I’m meticulous about paying each and every one off on time. And you, too, can have a healthy credit score, pay off debt and maximize the benefits credit cards offer — even if you’ve had credit issues in the past. Stay tuned for all the coming posts in our personal finance series that will help you with topics like tracking expenses, financially prep to buy a home or have a child, build credit, take a budget vacation and much, much more.


Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.