9 Realities of Debt Repayment that No One Prepares You For

The lessons I learned the hard way while climbing my way out of debt.

Going into debt is easy, it’s the paying it back that’s difficult. At the time I’m writing this, I am one or two months away from paying off the rest of my unsecured debt. As I reflect on this major financial milestone, there are several realities about debt repayment that I learned along the way.

Some of the lessons learned I’m glad that no one shared with me because I’m sure I would have given up. Other lessons I wish people would have shared with me so that I would have been mentally prepared to deal with them. Learning how to get out of debt doesn’t exactly come with a handbook. So I’ve taken notes to share with others.

Here are nine lessons I’ve learned about getting out of debt the hard way…

1. Debt Repayment Sucks

Seriously, it really does. And, paying off debt, especially a significant amount of debt is harder than most people can imagine. That’s why people love going on the Dave Ramsey show and doing their “Debt-Free” scream. These people know how hard paying off debt can be, especially when you’re bombarded with constant consumption messages and how spending will make you happy.

Well, I spent to the point where I was no longer happy and hated owning other people money. Each time I paid a bill off I just thought to myself, I am so thankful that I’m able to pay this bill and why in the heck did I think it was a great idea to purchase:

• Coffee
• Vacations
• Shoes

And other pointless items with a credit card? Or, just using money that I didn’t really have at the time. Each payment became a moment to reflect on all of my previous financial choices. And, I had to stop beating myself up each time I paid a bill. The reality is that most people make choices with the information that they have at the time. As a result of my debt-free journey what I know now about money, my personal financial habits (I’m a natural spender), and what makes me happy completely different from a billion years ago when I began paying off my debt.

Oh, and paying off thousands of dollars of debt is harder and more emotional than I could ever imagine and, yes, I would do it again.

2. No More Creditor Love

As you begin paying your bills off you’ll discover how much white noise debt creates in your life. As I paid off more and more bills, I discovered something by accident-creditors (even if you’re in good standing) contact you a lot. Below are a few examples of what I discovered.

• Creditors send helpful payment reminders each month to keep you in the loop with your bills. While this is actually a great thing, imagine multiplying these email notifications by 25 services, subscriptions, and other miscellaneous bills.

• If you’re in good standing with a bill you may receive a call every once in a while with an upsell for a “better” product. You may also receive calls to check on how your happiness with a product or to follow up on an incomplete upsell. Maybe you vaguely agreed to purchase something better from your creditor or service provider and then changed your mind.

• Then, there are the calls that you get when you’re in bad standing. It pains me to admit that I’ve received more than my fair share of calls concerning overdue items. This was especially the case when I began my debt-free journey and had at least 30 creditors that I owed money to. It sucked, was very mentally draining, demoralizing, and scary.

The calls have basically stopped. I still have a few minor debts and I still have to talk to them on and off, but I can tell you right now that I the one thing that I wasn’t prepared for as I paid off my debt was finding out how often I was being contacted about money-related issues.

3. It’s complicated

Debt-life is so complicated. Especially if you owe money to a number of different creditors. Currently, I pay on fewer than 20 items, including business-related expenses. The majority of those expenses I try to prepay as much as possible, or their due dates fall at the same time. It’s pretty easy for me to figure out when something is due.  A couple of years ago that just wasn’t the case.

• The more expenses you have the more entities you are connected to.

• Even though I had automatic payments for the majority of my bills, I still had to watch my accounts to make sure that payments were being made on time.

• Each organization has a different way to communicate with their customers. My least favorite way to communicate with a creditor is if they only have a chat box available or if I get an overseas call center versus stateside. Each time that happened, I always ended up having to make an additional call to address the issue that I originally called about. And, I worked with international students for 10 years and lived abroad. I’m very comfortable working with professionals who speak English as a second language. But, for some reason, overseas call centers almost always have been a frustrating experience for me and those interactions make the debt-repayment process incredibly stressful.

Going from at least 50 entities that I was dealing with to just under 20 has decreased the level of financial complexity that I was dealing with and I have a lot more mental energy to focus on earning more to pay on my debt.

4. I Was Paying How Much?!

For a long time, my money was on autopilot. I really had no idea how much I was paying toward debt each month because I didn’t have a well-organized system (read-budget) tracking where my money was going.

Imagine my surprise when I started tracking my expenses and discovered how much I was spending each month. It was an incredibly painful and illuminating experience.

5. What to do when you want to quit

No one tells you that there will be points during your debt-payoff journey when you want to give up. Quitting happens because as I mentioned before, debt-repayment is hard. I’ve quit several times during the past six years of my journey and now I like to joke that I needed to take a vacation from my plan. Paying off significant amounts of money takes a lot of mental focus, time, and energy. There are moments when I just had to recharge and start over again. Each time this would happen, I was amazed at all of the progress from when I began my debt-free journey. In fact, in the past year I took a break because I was mentally tired. And, I’m back at it again with just six small bills to go.

6. You don’t have to go it alone

There is no way you can pay off debt alone. I found a community of like-minded people who cheered me on, shared fun and exciting tips about how they were paying off debt, and listened to me when I was feeling down.

I’m friends with these amazing and supportive people to this day, and I attribute a lot of my success to their support. Where to find a community like the one I’m in?

• Read personal finance blogs. It helped to discover that I wasn’t the only person struggling with debt.
• Join closed Facebook groups that share debt-repayment ideas, side-hustle suggestions, and more.
• Follow Instagram threads that shared debt-payoff journeys.

Participating in these spaces will help you find your tribe.

7. A positive mindset is everything

What you think, is what you believe. The hardest part of every debt-free journey is believing that you can become debt-free. This surprised me. Currently, I spend a significant amount of time telling myself that I can, and will, achieve my goal. Focusing on mindset is a daily task and it’s non-negotiable. Doubt will kill your process, make you question your goals, and weaken your resolve.

Every day for five or 10 minutes, I make a point of focusing on my mindset. And, that focus has made all the difference in my journey.

8. Small wins snowball to bigger ones

I’ll admit that I’m a bit conflicted about Dave Ramsey. I’m a fan of a lot of his teachings, I just wish he wasn’t so grumpy! The one thing that he is 100 percent right about is that experiencing small wins by paying off your smallest bills helps to set the stage for larger successes.

Each time I paid off a bill I would experience an energy boost! One less business to deal with and my list of creditors was getting smaller.

9. Remember that it’s a journey

Never in my wildest dreams did I think it would take me almost seven years to get to this point. I’ve had the good fortune to speak with a large number of people who had seven, eight, and 10-year financial journeys. They all agree that it feels like the time goes by in a blink of an eye.

These same people are also accumulating a lot of wealth now because the money they used to spend paying off their debt is now used to invest in their future. And, most importantly, they no longer make the financial mistakes that created their original financial mess.

No matter where you are at on your debt journey, I want to encourage you to keep working on it. There will come a day when you look back and are amazed at the progress that you’ve made. My financial life isn’t perfect right now, but the amount of progress that I’ve made is phenomenal.

About The Author:

Michelle Jackson is a personal finance writer who has learned everything about money the hard way. She has paid off thousands of dollars in debt and is excited to help educate others on how to grow their money, stay debt-free, and live their best financial life. When she’s not geeking out about money, you can find Michelle hiking in her home state of Colorado.