One Of The Scariest Money Conversations I Ever Had (And How It Changed Everything)

Here's what you can learn from it.

My congressional press pass from more years ago than I’d care to admit.

Hi there, my friend.

I’ll never forget it. I was standing in my studio apartment in Arlington, Va., just across the river from Washington, D.C., talking to my girlfriend on the phone.

“We should take a trip somewhere,” she said from her apartment in Austin, Texas.

I don’t remember where she wanted to go or when, but I distinctly remember how terrified I felt.

Oh, my goodness. I’ve got to tell her. It is time.

I had no idea how to do it. More importantly, I had no idea how she would react. We had been living a time zone away for several months while I tackled my first real journalism job out of college — covering bank regulatory compliance for a banking trade publication in D.C., which was about as fun as it sounds — but we had been together for years. Still, she didn’t know how much debt I had run up.

I knew it was possible that I’d tell her and she’d run screaming, but I just had to do it. Right then and there. She needed to know.

I don’t remember exactly what either of us said – the emotions around the conversation are more vivid memories for me than the actual dialogue -- but the gist of it was this:

• Me, with sweaty palms and trembling voice: “Umm, so I don’t think that’s a great idea. I have about $10,000 in credit card debt right now, and I just don’t think I can afford to go anywhere.”

• Her: “Oh wow. Ok. I had no idea.”

• Me: “No one does, but I felt like you needed to know.”

• Her, calmly: “Thank you for telling me. Now, let’s get to work knocking that down.”

She didn’t hang up and ghost me. She didn’t mock me or laugh at me. She didn’t try to convince me that I should go on the trip anyway. She didn’t interrogate me about how it happened. (Mostly through my own bad choices, to be honest.) She just wanted to help.

That changed everything.

What happened next

From then on, she helped me stay disciplined. I devoted the vast, vast majority of my income that wasn’t going to paying basic bills to paying down my credit card debt. I didn’t have any grand strategy beyond that. I didn’t use balance transfer credit cards. I didn’t call any card issuers and ask for breaks. I just slashed my spending and whittled away at it over time.

In all, it took four to five years to pay it off. During that time, I changed jobs multiple times, moved from D.C. back to Austin and then off to San Diego and Oakland.

In the process of paying down the debt, I did get a break in being able to live in an apartment above my girlfriend’s coworker’s garage in Austin for significantly less rent than I would’ve paid elsewhere, which was hugely helpful. I was also lucky to stay healthy during that stretch. However, the biggest help was that I was able to boost my salary substantially by changing jobs during that period. If I had stayed in that job in D.C., the payoff would’ve taken far longer.

Another big event happened while I was paying off that debt: I got married, to the same woman I’d had that terrifying conversation with a few years earlier.

We’re still married today, and so much of what we’ve been fortunate to build over 26 years of marriage can be traced directly back to that conversation in my studio apartment all those years ago.

The big takeaway

It is hard to be vulnerable with the ones you love. That’s certainly true when it comes to money. So many of us feel an enormous amount of shame around our debt. We feel stupid, like a failure or loser. Believe me, I’ve been there. Those feelings consumed most of my 20s.

Here’s the thing, though: You’re none of those things, and people want to help you. Your family, friends and colleagues want to help. Countless organizations, from lenders and nonprofit credit counselors to community and religious groups, want to help. The problem is that they can’t do it unless they know you need the help.

Some may offer financial help. Others may just offer emotional or spiritual support. It is all important. Paying down debt can be a herculean task when you’re doing it by yourself. Having a group of people cheering you on can make all the difference in the world. It can help you keep moving forward when you don’t feel like you can anymore.

Lastly, you may not believe it, but your credit card issuer may want to help you, too. A 0% balance transfer credit card can be perhaps the best weapon in your battle against credit card debt. Also, lenders have so-called hardship programs designed to help people through short-term rough patches. These programs can include: temporarily lower interest rates, waived or reduced fees, delayed or deferred payments and other breaks that can be hugely helpful when wrestling with credit card debt. But you won’t get the help if you don’t ask.

Why would they do that? Return on investment. They know that if they help you when the times are darkest, it will create so much goodwill that you’re likely to remain a customer for a long, long time. When that happens, banks make far, far more money off you than what they gave you in those breaks when times were tough. That’s good for the bank’s bottom line, which is ultimately what matters most.

If you still don’t believe it, consider this: 76% of people who asked for a lower interest rate on their credit card in the past year got one, according to a report from LendingTree. (Full disclosure: They’re my employer.) And that success rate has been steady for years. I’ve talked about that a million times in interviews, newsletters and more, and it even inspired me to write my book, which includes a chapter on exactly how to ask for a lower rate.

However, they can’t help you if you won’t ask. But if you are brave enough to ask, amazing things can happen. It can change your life, just like that conversation I had so many years ago.

Share your scary money conversations

I know I’m not alone in having a terrifying money-related conversation. Tell me about yours in the comments below.

Until next time,

Matt