What are your Biggest Challenges with Paying Off Debt?

As many of you know, this past weekend I attended the Financial Blogger Conference in Chicago. The atmosphere was amazing and I learned so much about what I should be doing better to build the Enemy of Debt community. I won’t get into the details of the conference here, but if you are interested in seeing just how awesome it was simply sign on to Twitter and search for the hashtag #fincon11.

I will say this though. Meeting most of Team EOD in the flesh was absolutely awesome! I am so lucky to have such talented writers contributing to my vision here at Enemy of Debt. The only guy I’m still waiting impatiently to meet is Clair but I’m sure it will eventually happen. To Travis, Suzanne, Paul, Ashley, & Jessica; I really enjoyed the entire weekend and you guys played a major role in helping make that possible. Here’s to lasting friendships! ๐Ÿ˜€

Now I want to boldly go in a new direction with what I’ve learned by asking you one simple question.

What are your biggest challenges with paying off debt?

Paying off debt is a difficult journey and the one thing I want to do here on Enemy of Debt is to help you as much as I can. Perhaps the most important piece of information I learned at the conference was that I need to focus on YOU and write about the things that matter the most to you as you work towards becoming debt free.

I am not unsatisfied with what I have done in the past but I would be a fool to say that there is no room for improvement. After returning from the conference I took a peek into my archives to see what resonated with the readers the most, what received the largest response, and more importantly what inspired you the most. It didn’t take me long to realize that the articles that were about my own struggles seemed to inspire the most amount of feedback.

An article I wrote last year called No Restaurants in November was a complete success because not only did I build my readership because of that challenge, many of you emailed me to let me know how much of an impact that challenge had on your life. Some admitted to never having even thought about how much they went out to eat while others claimed the amount of savings they experienced (even though they may not have done the challenge perfectly) helped them pay off more debt than they would have otherwise paid down.

What I like most about what I’ve done up to this point on Enemy of Debt is mostly related to articles that ask you to do something. I like action steps and try to implement them whenever I can but one thing I noticed was that I seemed to focus (a little too much) on why you were in debt. I do think it’s important to know why so you can address where to go from there but I am going to make it a point to open up with the possible problem or reasons but then focus more on the steps needed to move forward.

The one thing I don’t want to do is sound arrogant by always beating you up about why you are in debt. For the record, that has never been my intention and I think most of you know that, but I can definitely see how some might walk away from the computer feeling like a failure. My ultimate goal here is to build you up, empower you,ย  and to make you believe in yourself so that your debt free journey doesn’t feel impossible.

Becoming debt free is more than possible but one thing I’ve realized is your debt free journey might not look like my debt free journey. During a conversation with Ninja from Punch Debt in the Face and Suzanne from CareOne, we all agreed that there is more than one way to skin a cat. Ninja pointed out (as a fellow enemy of cats), that it wasn’t important how you do it, just that you do it…literally.ย  Ninja has the best sense of humor! I hope you have a sense of humor too. I’m not going to really skin any cats but that doesn’t mean I have to like them either. ๐Ÿ˜€

Anyway, expect Enemy of Debt to go through some changes in the near future. My goal has always been the same — to make Enemy of Debt the best debt free motivational tool around — so now it’s time to put some of what I learned from the awesome speakers at FINCON11 into action.

In order for me to start that process I need to know how I can best help you reach your financial goals:

What are your biggest challenges with paying off debt?

Let me know in the comments section and I will develop articles based on your answers. Feel free to also include challenges with managing your money or personal finance in general. I’ll do my best to address it all. And lastly, thanks for reading Enemy of Debt and I sincerely look forward to building the community and creating a powerful resource for you all.

About Brad Chaffee

38 Responses to “What are your Biggest Challenges with Paying Off Debt?”

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  1. Sun says:

    We are just starting out with our journey. We are still struggling with a debt. We spend beyond but knowing where to cut has been contentious. What I vaLue as important may not be the same as my wife. The other issue is actually cutting back. Last month we spent $1200 eating out (we had Vegas and a wedding) but this month we targeted for $400. Delaying now for the future is a downer. Hopefully, we will make progress and see our sacrifice bear fruit.

    • Brad Chaffee says:

      Sun thank you for the great feedback. It sounds like we have something in common with the eating out stuff. Look for No Restaurants in November 2011 coming up soon. Not completely sure by your comment but it sounds like you are saying you and your wife may not be on the exact same page. If that’s true, you’re not alone, my wife and I had the same problem but constant communication and completing our goals resolved that issue over time. We still don’t see eye to eye on everything but who does? ๐Ÿ™‚

      Expect big things from EOD in the coming future and if my readers think they have seen passion up to now, wait until I step out of the phone. Motivation on CRACK! LOL seriously though, hang in there and you gave me some good bits of info to process and turn into something helpful for everyone. Thanks for the great comment!

  2. Lynda says:

    The biggest challenge and it’s why I’ve searched out blogs like yours is to stay motivated. Let’s face it, the initial enthusiasm of determining to be debt free begins to wane in the months and even years it takes to stick to your plan. Life always brings new challenges that add to your ability to get off track, so finding others who are in process or succeeded gives a nudge in the direction you want to keep going.

    My family and I just completed a months challenge by another blogger to spend nothing outside of budget that wasn’t absolutely necessary for the whole month of September. We did this in conjunction with others who signed onto her blog challenge and found it interesting and truly a test to not buy anything for the month. So with a freezer and pantry full we were off, and found the amount saved by not running out for an item here or there, that always turns into more we saved ALOT!! Just the gas alone these days saves by not using. Having the accountablility and encouragement of what were before this total strangers, was what made you stick to the plan.

    The articles your blog provides are interesting and useful, I think it’s the personal stories of others who’ve made real strides that encourage me the most. You feel less isolated in your pursuit. And when you get there hopfully there are those you’ve found along the way who can celebrate your success with you, because it is a test of will and discipline that doesn’t generally have a quick finish line to aim for, it’s more a marathon than a sprint.
    Glad you found more inspiration by being around others who are like minded. Keep passing it on, it is needed and appreciated.

    • Brad Chaffee says:

      Lynda, motivation was why Enemy of Debt was born in the first place. I was so motivated and passionate I had to release that pent up energy somehow. not to mention the roller coaster ride that becoming debt free feels lie at times, especially when you hit the big debts with less quick wins along the way. I know that feeling oh so well and have kind of experienced it with building our emergency fund after becoming debt free. I’ll tap into that frustration to knock out some inspirational articles on staying motivated. Thanks for the comment and thanks for reading Enemy of Debt! ๐Ÿ˜€

  3. For me, it’s earning enough money to live off of AND pay on my debt. I realize that I’m a unique case though since I’ve been unemployed for so very long.

    It was so great to meet you (and the rest of TeamEOD, minus Clair) at FinCon. I look forward to more collaborating and of course, FinCon12

    • Brad Chaffee says:

      earning extra money? I’ve got some great ideas for you and let me just say I loved meeting you this weekend! You are a riot and I am so glad you ended up making it. Now all we have to do is get Clair to come to FinCon12! ๐Ÿ™‚

  4. Vicki says:

    For me, it is motivation and not having a partner who does not see my POV. My budget is so limited, and so there really is no room for extras, but each month I manager. What keeps me going is that on my blog, I have a weekly U-rah to those bloggers that I follow who have had success, no matter how large or small. By cheering them on, I am cheering myself on. One of my followers indicated that they loved getting an U-rah from me, and now it is sort of a competion.. LOL! I know you have the feature for those who are debt free (which I can’t wait to become a member of that club), but it would be nice to get motivational boost from someone who has either been there or is going thru it.

    • Brad Chaffee says:

      Vicki, Vicki, Vicki! I feel your pain. I learned a lot while beginning our journey back in the beginning of 2008 and would love to write a comprehensive post outlining my experience, what I would have done differently, and where we are right now. If you could, and feel comfortable doing so, give me a few example s of things you and your spouse bump heads on. If you’d rather not do it here feel free to email me at freedom@enemyofdebt.com letting me know specifics There are so many mistakes couples make when dealing with money and I know from experience. I was a bit too aggressive with my wife and at first didn’t really listen to her POV but as I realized that I was able to adjust and realize sometimes it takes time for someone to see what you want them to see. I pushed when I should have been a little more patient.

      That is a GREAT idea to have stories from readers who are still working on their debt free journey! Thank you for sharing that! I will definitely put something together that accomplishes that. The best part of FPU groups each week was that everyone was coming from the very same place and could relate and give each other hope. I can’t believe I didn’t pick up on that earlier and do something based on that dynamic. Thank you for the idea and I would love to know what blogger currently runs that series. Thanks! ๐Ÿ˜€

      • Vicki says:

        I don’t know of a particular blogger that currently runs that series, but when I see that a fellow blogger has low morale, I try to write something for them.

        • Vicki says:

          Oh… I am sending you an email regarding the particulars about the spouse.

        • Brad Chaffee says:

          Oh okay, I misunderstood. I just re-read your comment and understand now. It’s awesome that you take time out of your day to congratulate and help celebrate the wins and achievements of others! ๐Ÿ˜€

          Oh and looking for that email. ๐Ÿ™‚

          • Vicki says:

            I think it is important to provide support. It helps others and encourages them, and in turn, they encourage me. It is true what they say.. United we stand – Divided we fall.

  5. Dena says:

    You are the very first blog I ever signed up for.Your personal approach is what pulled me in.It doesn’t matter if someone made $100,000 or $20,000 a year.We all have to start taking control back.You gave me that courage and will power.It’s saved my behind so many many times.I never even knew what an emergency fund was back then.But I’ve got one now.I loved the no restaurant challenge you did.I still do it every couple of months.It’s a super easy way to add to your savings.For me personally,my biggest hurdle is how long it takes to reach a goal.There are times I feel like I’m banging my head against the wall and getting nowhere.Burnout is my enemy.If you could find a cure for that I would be set.You’re doing a great job on this blog.And I appreciate all the work you put into it…….. Dena

    • Brad Chaffee says:

      Dena how many times do I have to tell you YOU ROCK! You really know how to make a guy blush. It’s reading comments like yours that make me feel like I am doing the right thing by continuing to keep EOD alive. I love the fact that even though I’m not a big dog (yet) I still get to hear from readers like you who have taken something away from something I have written. I just love that and it truly means the world to me. Congratulations on evolving your emergency fund from nothing into something. That is really a hard thing to do when you’ve never had one before so great job!

      As far as the motivation thing when it comes to reaching your goals, I know what you mean. When we were paying off the last $8,000 to Sallie freaking Mae, who I may have pimp slapped if she were a real person, we hit a low and even had a few months where we didn’t make the progress we had previously made on other debts. It inspired me to write the post about how to break up your larger debts into smaller achievable goals so that you can have some quick victories along the way. It’s really a mind game because you know it’s not separate debt but if you right it down EVERYWHERE as if it where it really helps fool the mind. Look for some more posts from me on that topic.

      And again, thank you for making a guy smile so big! Any time you need anything just email me or something. In fact I would love to connect with you on Skype or something someday! The Financial Blogger Conference has gotten me to come out of my shell and I hope to connect with people face to face like that way more often. One thing I’ve learned is that face to face tends to be more productive and valuable and has a way of inspiring great ideas. Skype is the closest thing to having that face to face moment.

      YOU ROCK!!!!!! ๐Ÿ˜€

  6. Brad, you talk about coming out of your shell at the conference….I could definitely see something ignite in you as the conference went on. Just being around you made me take another look at myself and look for ways I can do better. That’s what I’ve always loved about your blog is that you don’t pull any punches.

    Are you in debt? FIX IT.
    Think you’re doing well? YOU CAN DO BETTER.

    That’s what I get every time I visit your website. Love it.

    Dena and I are alike in that you were one of the very first blogs that I latched onto when I entered PF blogosphere last December. You’re restaurant only challenge was my very first interaction with you.

    I found it amazing that you took the time to interact with me even though I was clearly brand new to the PF space. And as I told you at the conference, I find it mind blowing that I’m now actually contributing to EOD.

    I can’t wait to see what’s in store for EOD in the future, and am excited to be a part of it.

    Now, to answer your question….what is my biggest challenge in paying of debt? I don’t know what you’d call it…maybe it’s fear. I start off a budget, and make a mistake. Have an unplanned expenditure in a moment of weakness. At that point I’m afraid to look at the numbers out of fear that they’re going to tell me I’m in trouble. That they’re going to tell me I have to have a discussion with my family that we have to cut something else out because I made a mistake.

    I’m afraid to admit that I make mistakes. I’m afraid to not be the perfect husband and father to my wife and family. Which is stupid because I’m not perfect. I’m sure they know that.

    But admitting it over and over…..yeah, that’s my biggest challenge…..

    • Brad Chaffee says:

      Travis I’ve told you many times why I admire you man! You and Vonnie have jumped on a voyage that must have seemed like raging waters in the beginning but you pushed on. Dude that says a lot about your character, integrity and how dedicated you are to doing what’s right. I’ve known more than a few people who decided bankruptcy was the right choice though they weren’t facing raging waters at all but something a little closer to a kiddie pool after a tennis ball caused a ripple. You and your wife rock man and it is an honor to have you on this team. I love ya like a brother my friend and am really glad I got to meet you finally!

      I definitely appreciate all of the nice things you have to say about me and this blog. That stuff keeps me going and gives me the drive to continue to wear my Enemy of Debt costume yet another day.

      Now to address your concerns about your own behavior and fear. This isn’t going to eliminate any future articles on this subject btw, I just want to say one thing. Fear isn’t the worst thing in the world. fear keeps us on our toes and keeps us thinking about ways to avoid the things we are afraid of. what you should do however, is take that fear and place it in a different location. Use your fear to your advantage by being more afraid of NOT knowing what a mistake has done to your situation and journey.

      Let me just say I know exactly what you mean though because I experience that same feeling. We all probably do. That is what I try to do. I try to place the fear on what I don’t know and what that will cause rather than making the mistake in the first place. In other words your fear of not finding out, not wanting to have the meeting to admit failure will more likely cause a bigger problem than your original mistake.

      Okay so that was a BIG “one thing” but I hope it at least made sense. ๐Ÿ˜‰

      Not sure if I said all that in a way people will understand but that’s what I try to do. Now if I could just use that same example to make myself get on the scale after messing up with my weight loss program. This is where I believe we can help each other my friend!

      Great comment as usual Travis and you’ve given me lots of ideas to write about in terms of the fear we face daily with our own unique circumstances and mistakes. You seriously rock man, but you already know that because you already clicked the YOU ROCK button to submit this comment. ๐Ÿ˜€

      Keep doing what you’re dong my friend and I’ll fly out to your house and celebrate with you once you become debt free! That is not a threat, it’s a promise! LOL I’ll do it!

      • That makes perfect sense, friend! Unfortunately, it’s one of those easier said than done things for me. I just have to push myself to do it…just like I pushed myself to start eating better and exercising at the beginning of the year.

        To be honest with you, this is the first time I’ve ever been ever to really articulate why it is I do what I do. Therapy EOD style in the comments section…..

        I’d love you to celebrate my “debt freeness” with my family and I! You’ll have to go to Baltimore though – we’ll all hook up with Suzanne and the CareOne friends. ๐Ÿ™‚

        • Brad Chaffee says:

          Don’t I know it. LOL That’s why I threw the example out about the scale. I looks like we struggle more with the opposite thing. LOL

          Baltimore makes it even easier! ๐Ÿ™‚ I’ll be there dude!

  7. Julie says:

    Love your articles! My biggest challenge in getting out of debt is “TIME!”. For one, my family is always on the go. For a working mom, it is hard to organize dinners. It is hard to “shop for the best bargains”. It is hard to “coupon”. I just don’t have the time, or energy. It is also hard to find the time to sit back, and refocus on how to save. We just Go, Go, Go! Hopefully ONE DAY, I will pay off my debt! And no longer be a slave to the lender!

    • Brad Chaffee says:

      Time management is a pretty big issue. I have written about it in the past but not too in depth. I could definitely use the lesson I’ll get from writing an article about time management.

      Keep your head up Julie, you’ll get there. Replace “hopefully” with DEFINITELY because you WILL do it. It may take you more time than others but as long as you take a bite at a time you’ll make to your destination. ๐Ÿ˜€

      Are you a single mom or is your family a two income family? Just wondering because that’s a subject I would like to touch on. How many kids do you have? ๐Ÿ˜€

  8. Glen Craig says:

    Biggest challenge in paying off debt? Having the cash! That’s something we are always working on.

    It was great to meet you at FINCON11 Brad! Thanks for sharing the cab ride and the great conversation.

    • Brad Chaffee says:

      Likewise glen! I really enjoyed getting to know you man! I’ll go ahead and give a shout out to stay at home dads everywhere! ๐Ÿ˜€

      I’m feeling a extra income related post with regard to your comment. Thanks for the inspiration. ๐Ÿ™‚

  9. Nancy says:

    I agree with everyone who mentioned keeping up motivation while paying off debt for the long-haul. For me, motivation specifically means other people’s success stories (your debt-free reader success stories are what drew me to your blog originally). I love reading about how people paid off $X amount of debt in X amount of years/months because it reinforces that some day (22 months from now), that will be me! If I could make one suggestion, maybe your debt free success stories could be longer and not just a quick Q&A.

    • Brad Chaffee says:

      Yeah Nancy I love your suggestion. It’s about time I change the format of that series up anyway and your idea is a perfect way to do that. AWESOME! Yep, you ROCK! ๐Ÿ˜€

  10. Nate says:

    While getting out of debt is rewarding, you’re right, it still seems challenging to always keep motivated with it. If life could stop so we could pay off debt, that might be easier, but life goes on and so it can be challenging to keep paying off while other demands of life come up. We feel saying “no” to some of the enjoyable things of life is tough and sometimes that is what is required when it comes to that or getting the debt paid off.

    • Brad Chaffee says:

      Sacrifice is definitely an integral part of paying off debt. I’ll be the first to admit that while my wife and I have saved a crap ton of money over the last year we could have done much better. You know what though, life happened to us along the way and it definitely put a damper on our progress.

      We feel our progress is not happening fast enough but we are doing things to change that too. My new business will account for the income part. This past year has been a big year for extra expenses due to a new baby, unexpected trips, and upgrading our vehicle so I am hoping for a super 2012! ๐Ÿ˜€

      One things is for sure though…life happens whether we want it to or not.

      • Nate says:

        Congrats by the way on the new baby. Yeah, I hear you on the unexpected expenses. That happened to us this year with not just one, but two vehicles which we weren’t planning on at all, but yeah, life happens.

  11. Den says:

    I agree that having the patience to keep slogging away at our debt is hard. Sometimes we hit all our goals and are flying high and other times we get hit in the face with “life”….but we keep telling ourselves to keep moving forward and we’ll eventually get there.

    I love the reader stories and your stories Brad – so much more interesting than dry financial information. I also love all the “hacks” people do to save money!

    Keep up the great work – I enjoy reading EOD every day!

    • Brad Chaffee says:

      Thanks for the compliment Den. I know what you mean, personal finance is a slippery slope and can sometimes get very boring in nature. I’m glad you enjoy Enemy of Debt and will strive to give you more of what you like. Thanks for the feedback! ๐Ÿ˜€

  12. Brad it was truly a pleasure meeting you and the rest of Team EOD (minus Clair) at FinCon11–I had an amazing time getting to know everyone and realize they are all real people like me, facing the same life struggles. What I love the most about personal finance bloggers is their willingness to share their stories even though they are often very personal in an effort to help others.

    I am so thankful to be part of the AMAZING Team EOD–I look forward to getting to know everyone even better and of course FinCon 12!!

    • Brad Chaffee says:

      Yeah FinCon11 was completely awesome and I can’t wait until we get to do it again! ๐Ÿ˜€

      We’re gonna rock the pants off of the end of 2011 and into 2012. Yeah that’s an inside joke based on Will from Wisebread talking about blogging in his underwear. LOL

  13. Jenn says:

    I’m enjoying reading each of these comments!

    Brad I was drawn to your site because it connected me with folks like you who have the anti-debt mindset that is unusual in society today. Even when I was convinced that driving a very used paid-for car was the right thing to do, for example, it was difficult for me to hold my head up among my professional peers with new (certainly financed) vehicles. I’m not normally an approval-seeker, but it was awkward even for me to justify my decisions though I knew they were right. And then it trickles down to smaller things… are my kids deprived if we don’t buy school pictures? order pizza once a week? Go to amusement parks and other costly weekend activities? Folks on these blogs can relate and remind me that it’s not only okay, but it’s actually better to think long-term.

    Just as I look at ‘before and after’ weight loss pictures to motivate me to be physically healthy, I like to see real budgets for folks getting out of debt. It motivates me to be financially healthy. And like weight loss, when I see someone who started out in worse shape than me and they succeeded, well I know that I can do it too. I like that your style isn’t finger-wagging, but REAL and that you often use yourself as an example for both good and bad patterns of behavior. Thanks for keeping this going, and thanks for listening.

  14. Great meeting you at FINCON, Brad!

    I think my biggest challenge is trying to figure out how fast to pay down my debt, and if I should save money on the side before I have zero debt. Currently, I have about $3k in low-interest student loans left to pay off. I want to get rid of this quickly, but I also want to keep some money in the bank for short-term savings. I know it makes the most sense, in terms of interest, to pay the debt off first, but I don’t always feel comfortable doing that.

    • Brad Chaffee says:

      Jeffrey you had me hooked with your credit card post my friend! I am glad that I found your site and look forward to getting to know you.

      Dude, you are almost there! $3,000 left to go and you will be singing the debt free song! That is awesome! Now when you say short term savings are you referring to a sinking fund or an emergency fund? I just want to be sure.

      While we were paying down our debt we kept $2,000 in our baby emergency fund. This amount of money was plenty enough to cover unexpected emergencies so anything more than that I would have used to pay off my debt. Some people (like Dave Ramsey) only recommend having $1,000 in that fund but it just wasn’t enough for my wife so we pumped ours up another $1,000 but rarely did we have an emergency that cost us more than $1,000.

      We also carried a sinking fund to cover irregular expenses such as car repair, Christmas, etc., so that we wouldn’t have to use our E-Fund. Whenever we had a car repair we would replace the money and then start paying down our debt again once it was replenished.

      Good luck man. I am excited for you and look forward to hearing about you kicking Sallie Mae out of your life! She’s a real NAG! ๐Ÿ˜€

      • I guess you made me rethink this a bit, Brad. I was thinking it’s more for short-term spending (i.e. within the next year) for things like vacations. I suppose that’s a sinking fund of sorts, although I haven’t set an amount to replenish, too. Sounds like something else I should think about!

        I do have a dedicated baby emergency fund of $1,000. I live pretty cheaply and don’t own a car, so I feel at least somewhat secure with this.

        Glad you liked my post, Brad! I’m hoping to be back here soon announcing that I’m debt-free!

        • Brad Chaffee says:

          Awesome man, BRING IT ON man I can’t wait! Debt freedom is amazing and I wish could convince EVERYONE of this but you know how that is; you can lead a horse to water but you can’t make them drink. LOL I’ll still try my best though. ๐Ÿ˜€

          The important part about your plan is that you are thinking about it and open minded to new ideas. Here’s an idea for you based on what we did. I realize my wife and I were a bit extreme (mostly due to me being so hardcore about it) but we made the very hard decision to skip any and all vacation plans until we were debt free. We had to say no a few times to special invitations to see family but in the end we were glad to have gotten rid of our debt as fast as we did. As far as our vacation life has gone since; well we still haven’t taken that big cruise or trip to Europe like we want to because we wanted to build our emergency fund to $15,000 before doing so. The problem with that is that LIFE punched us in the face a few too many times last year but we have taken small trips so we’re not doing all that bad either.

          I’m looking forward to that cruise. If my business takes off and we can double our combined income that cruise will happen next summer. That is the goal anyway. ๐Ÿ˜€

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