April 29, 2016

Hey everyone, we have a great new Dear Debt letter from Pamela. Pamela is a personal finance blogger that likes to help other millennials eliminate their debts. Her professional and educational background is in accounting/finance, but she has not always been good with her own money. After some learning some life lessons, she and her husband embarked on a journey to pay off $120k of debt in 2.5 years. They now live debt free and are building their wealth while she blogs at her site, MyMoneyCounts.org. This witty letter comes from her experience with debt.


Dear Debt,

It’s been a roller coaster ride with you, but it’s time we part ways. I don’t know how much more uncertainty I can take from you. You said you would always be there for me. I thought you had my back, but you lied to me.

There were so many secrets and lies you kept from me. How can a relationship grow that is built on lies? Like the time you said you had my back and convinced me to buy my living room furniture on credit. You told me we could afford it. You said we would be OK, so I listened. Or when you told me that you would take care of me once I was done with school and encouraged me to spend the little I had and more without giving a second thought. But I am done with school now and your words were just empty promises. Where is the help? Where were you when I needed you, debt?

Why am I even surprised? You were never satisfied with what I could give you. You always wanted more and more from me. The more I got for you, the more you wanted. I felt like I could never do enough for you. Like the time I got us the big screen TV and game system, but that wasn’t enough for you. You wanted the new laptop and cell phone too.

Was it ever enough for you? Did I ever make you happy? You used to make me happy. I used to get so excited to see you. We had some of the greatest times together, you and I. Like the time we went on the road trip together or bought all those cool things together. You use to whisper sweet nothings in my ear. You had me wrapped around your finger. Then the trips, gifts and promises stopped coming. Then you stopped coming around. Now, when I look at you, I can’t trust you anymore. You deceived me… so I am moving on.

I will just come right out and say it, I met someone else. His name is cash and he is so good to me. He never lies to me or deceives me. He always has my back and is satisfied with what I can give him. We are building new memories and going on our own adventures together, cash and I.

I want to say thank you though, because if it wasn’t for you, I would never know how great a healthy relationship could be. Cash is the love of my life, and I have you to thank for it.

So long, and have a good life. Please change your ways so you don’t mess up the next girl’s life. Oh and don’t forget to lose my number.

Your Ex


This post is in: dear debt letter

April 27, 2016

Hey Everyone! We have a fiery new dear debt letter from Lindsay. Lindsay has always been the outdoorsy type, which is why she got two degrees in wildlife biology and conservation. After graduating, however, she was crushed when the only job she could get was as a lab animal caretaker. As her finances started tanking, she decided to learn more about how to manage her money. Eventually, she started a blog to document her journey, and then began freelance writing to start saving and work her way out of debt. She hopes to one day find her way back into the wildlife field, but will continue writing as long as she can. Check out her blog at NotoriousDebt.com.

Dear Debt,

F@<% off. It’s time for you to go.

We used to have a great relationship. You convinced me that with your help, I could do anything I wanted. Because of you, I moved across the country just two weeks after graduating from high school to start my adult life and get two college degrees. Because of you, I bought a house and a truck to go with it. Because of you, I paid for a surgery when my husband got sick, and to fix my house when it needed major repairs.

But the truth is I didn’t need you for any of this.

I could have saved the money I made while working through high school and college. I could have worked harder to get more scholarships. I could have saved up to buy a cheaper vehicle outright. I could have saved up money in an emergency fund and a health savings account so I could have paid for the doctor’s bills and the home repair bills in cash. But instead of realizing this, I became more dependent on you.

I wanted more things, but I didn’t know how to save up for them. Instead, I relied on you more and more when things went south. Over time, much like my little cousin Kelly*, you began barging more and more into every aspect my life. I couldn’t just go out with friends; you wanted to come too. I’ve never been on a real vacation with my husband, because I had to stay and work to take care of you instead.

No more. It’s over. You’re not the savior I once thought you were.

Instead, I’m going to save up for myself, like I should have been doing from the start.

I’m working on saving up an emergency fund of three month’s living expenses, so I don’t need to rely on you when shit hits the fan. I’m saving up for my husband’s education. I’m saving up to go on a real vacation this summer. I’m saving up to buy a car.

Truth be told, I’ll still need you at some point in the future. I don’t know if I’ll be able to save enough to buy a car outright by the time I need one. I’m saving up for a down payment on a house, but I won’t be able to buy it outright.

But you will no longer be my crutch. I’m standing on my own two feet now.
So get ready – because after I’ve saved up my emergency fund, I’m coming at you full-force.

Peace out,


P.S., Eat a d!<%.

*Name changed to protect identity and prevent awkward family reunions

This post is in: dear debt letter

Hey debt fighters! I’m in Italy with my mom, finally crossing my debt-free dream off the list. Feels so good and like all the hard work I did for years finally paid off.

I’m excited to get back to focusing on Dear Debt when I get back. After winning best debt blog and paying off my debt, I want to help others get out of debt. While I am doing what I can to financially help others get out of debt, of course I want to provide content that you will actually read and find helpful.

This year has been a bit insane from working on my book, moving out-of-state and traveling.

Even though life has been full of transitions and growing pains, this blog is still my baby.

So, I want you to tell me what you want, what you really, really want 😉

Do you want more content on how to get out of debt? More info on side hustles? How to start your own business? More emotional vomit from me? (ha!) More about overcoming money mindset issues? I want to hear from you! It’s important to me that I don’t just ramble in my own universe and I connect with readers.

So, comment on what you want to see or send me an email.


This post is in: debt

Hey everyone! I’m in Italy, so enjoy this awesome dear debt letter from Andrew. Andrew runs the site FamilyMoneyPlan.com where he writes about how he paid off his $320,000 mortgage in 6 years, and is now focused on finding financial freedom. If this letter resonates with you, I invite you to sign up for his newsletter. You’ll get a free copy of his e-Guide Money Guiding Principles for a Happier Life, which will help you along in your money journey.

“I’ve got another confession to make, I’m your fool…
Everyone’s got their chains to break,  Holdin’ you” – Foo Fighters,  Best of You

Dear Debt,

I think we both knew this day was coming. Frankly we have been putting this off way too long. I could say: “It’s not you, it’s me”.  But that’s not the whole truth, it takes two.

The truth is I’ve grown tired of you. I know it might sound fickle. You’ll probably say: “I’ve always been there for you when you’ve needed me,” and you would be right. Except, we were just too damn dangerous together.

I remember when we used to go out on a Friday night. It was so much fun. The early years, as we used to call them… Those nights where we were the king and queen of the party, living like we didn’t have a care, spending in the lap of luxury.

Then you would disappear, only to come back in the form of a letter. A simple statement. A statement that was telling me how much I owed you for the good time.

Those three little words you loved to say: “You owe me…”

You would come and go from my life for months at a time, and just when I thought I was over you …BOOM! You would magically appear. Ready for another great night, fun-filled weekend or quick trip. You always had a way of making me enjoy the moment. Forgetting whatever consequences would come from it.

Then that moment would be over, and as the memory faded, you grew to be more and more demanding. You became unbearable at times. Always nagging at me,  “You owe me! You owe me!” you would chant it like a broken record.

Just when I would get close to breaking it off with you, you would find a way to sneak back in. “Let’s get this!” you would whisper in my ear. “You totally deserve this!”

Like a fool I would blindly follow. You always knew how to bend my arm.

We just never fit together well. We were good in the moment, but I think we knew it could never last. So here I am, telling you it’s time for our “Goodbyes”. We have tried going our separate ways before, but this time it’s different.

You see while you have been busy making your statements to me, I’ve been busy too. I’ve been spending more and more time with a certain someone.

Her name is Cash. She’s not as seductive as you, but she sticks around longer and I feel good when I’m with her. I love holding on to Cash and I never want to let her go!

It’s funny… Cash would always show up whenever you disappeared. Probably a coincidence, but still… something to think about.

You see Cash and I — we’ve always had a thing. Bit by bit, we have grown fonder and fonder of each other. She’s nice to me, and she’s never once said/demanded: “You owe me!” because, well… it’s just not in her nature to do it.

Look Debt, I’m not saying you are a bad person. I know you will make others very happy, but you aren’t the one for me. So I’ll be packing up your stuff in the next few months. You can leave your forwarding address because I need you out of here ASAP.

I’m sure I’ll still see you around, flirting with my friends when we go out. You have a habit of showing up wherever I go.

That’s ok.

I need to get used to seeing you with other people on a regular basis. I’ll smile and be friendly. They (my friends) will have to learn my lessons on their own. It’s hard to watch, but I’ve learned my lesson.

I’ll be happy in just knowing that you just weren’t “The One” for me. It’s OK. I know you will find someone else. You always do.

My only wish is that you don’t do the same damage to them that you did to me.



This post is in: dear debt letter

I just got off a great call with Kara of From Frugal to Free who is preparing for her journey into self-employment.

I excitedly told her that quitting my job and working for myself is one of the best things I’ve done. It’s true. What I also told her was that you will never work as hard as you do when you work for yourself and there will be moments when you want to pull out your hair and throw a tantrum because nothing is working.

There are many joys to self-employment, including a flexible schedule and having a theoretically limitless income.

Over the past couple of years, I’ve enjoyed not waking up to an alarm (unless I have a meeting — as a policy, I think alarms are evil), working whenever I want and I’ve also grown my income more than I ever thought possible.

But being your own boss is also freaking hard.

Over the past few weeks with the move and my upcoming vacation, I’ve been working like a fiend so I can take two weeks off and go to Italy with my mom.

I’m currently in one of those “what the eff am I doing with my life” moments and feel like the amount of stress I’m under makes the vacation not even worth it. I know I’ll sing a different tune next week when I’m drinking espresso in Rome, but now it just feels hard and unnecessary. But if I don’t work, I don’t get paid.

And let’s be honest. If you have a full-time job, you are NOT productive for eight hours straight. The same goes for being self-employed, but the difference is I don’t get paid for checking emails and doing something loosely related to work. There’s also a lot of unpaid admin and promotion time. There’s always something to do.

Also, things that use to be “first world problems” like being frustrated when the internet goes out are now big deals. I make my living on the internet and over the past few weeks have been searching for a good connection like a fiend is looking for their next fix.

WHERE IS THE WIFI?!?!?! So I end up at Starbucks. Starbucks is not my first choice, but they have reliable internet so what can I say.

It’s kind of funny because lately, I’ve been that person who brings their whole office to Starbucks. I have my mouse and mousepad, my laptop and just stay there for hours.

Today I’ve already been to two Starbucks in-between a meeting (plus side: last week I worked at a brewery).

There’s also the issue of taxes and healthcare. During a particularly vulnerable moment this week, my accountant called me to discuss the damage for my quarterly taxes.

I almost cried on the phone, but if I’m honest I was crying before he called. My tax bill is not cute. Not one bit. And now I feel broke, right before my trip. Also, I pay a pretty penny for health coverage that in a word, blows.

Back to the crying…when I had a “real job” I was good at “putting on a face” if I was going through some emotional crap. Now that I work for myself I feel all the feelings all the time because I can be myself, by myself.  

While it’s great to not have to put on a social face for others, it really sucks to try to work when you are having a OCD panic attack or after fighting with your boyfriend, or feeling overwhelmed and stressed.

I want to tell my brain “STOP. Now. No, really.” It’s a struggle, especially if you suffer from any sort of depression and anxiety to continue to work when everything is up to you and you have to rely on your own internal motivation.

And let’s not forget about the never-ending impostor syndrome. I still get a rush when I submit articles and feel like, “Will they find me out this time? Will they realize I’m not really a writer and I’m just a good faker who likes to play with words?”

Or the panic/fear that I’ve messed something up. Or missed a mistake. Or that all my clients will leave.

But even after all of this, I wouldn’t change anything. I’m more resilient than ever and through the struggles and fear, I’ve realized that most of my issues stem from me. Nobody else.

As a perfectionist, I put a very high standard on myself, but I realize that I’ve dealt with a number of situations being self-employed and you know what? The world doesn’t end. You move on. And keep going.

Just wanted to share a glimpse into the other side as I think it’s easy for people to think you have it all figured out when you don’t. You’re just doing the best you can. Just like everyone else.

This post is in: freelance, life

Hey everyone! We have a unique dear debt letter from Aaron. Aaron has a love/hate relationship with debt. He’s convinced not all debt is bad, it’s just misunderstood. He writes about personal finance, mortgages, and buying a home at Mortgage Monks. He hopes that by educating themselves, people can learn how to use debt as a tool & avoid becoming trapped by it.

Dear Debt,

This just isn’t working for me anymore.

Look, I know we’ve had some good times. We were inseparable. When I was younger you were always part of the gang – together we were living the life and anything was possible.

For better or for worse, you have always been there for me and I appreciate that. You supported me through school. Without your help I could have never gone to college, and for that I am truly thankful.

But once I finished school and started working our relationship changed. We went to Europe together, but things were different. We both felt it.

The thing is, you have been really needy lately. Every few weeks you nag and nag and nag. You are relentless and I can’t take it. It’s ruining me. Because of you, I’m turning into a workaholic. You’re keeping me from my friends. From doing the things I love.

I’m sorry if this letter seems like it’s coming out of nowhere. But I’m in love with a girl. She’s amazing. I actually think you two could be friends under different circumstances.

Honestly I think she is the one. And there’s just not enough room in my life for both of you. We want to travel the world. We want to buy a house. We even built an Igloo together. I can’t do those things with you lurking in the background.

I know this seems harsh, but I just can’t have you around right now. It’s going to be hard for me, but my friend Earnest is helping me stay strong. I hope you can respect my decision.

I’m not saying this is goodbye forever. I’m fairly certain we are going to cross paths again in the future – I’m just hoping next time we can see each other for what we really are. If we can get to that point I think we can have a healthy, mutually beneficial relationship.

But until that time comes I’m going to have to go ahead without you.

Until then,


This post is in: dear debt letter

This post is part of the TaxAct #DIYtaxes blog tour which empowers you to take ownership of your finances by doing your own taxes. TaxAct provides the tools and guidance to help you confidently file your taxes easy and fast. Do your own taxes today at TaxAct.com. You got this.

“Did you do your taxes?,” I said to my boyfriend.

“Uhhh, not yet, but I got the forms from work,” he said.

“It’s April 5th. The tax deadline is right around the corner,” I said.

Realizing he was cutting it close to the deadline, I saw panic wash over his face. Now, I don’t like tax time any more than the next person, but my boyfriend has absolutely zero patience for anything administrative. As a personal finance nerd (and good girlfriend), I decided to help him out in exchange for dinner and dish duty.

Little did he know my secret that made doing his taxes a breeze: TaxAct.

TaxAct is an online tax software that helps you prepare your tax returns. If you have a simple tax return, it’s completely free.

It was easy to create an account with TaxAct, and since we had organized all of his forms, all I had to do was follow the prompts and fill in the blanks. Easy peasy!

If you’re also rushing to beat the tax deadline, you don’t have to go out and spend a ton of money on getting your taxes prepared by someone else. You can DIY-it and do your taxes yourself. Here are some tips for doing your taxes yourself and getting them done ASAP.

Gather All Your Paperwork

Before you do your taxes, you must get all your paperwork ready first. If you don’t, there’s going to be a lot of stops and starts, and doing your taxes will be a pain.

You’ll want to gather your:

If you’re a freelancer or even a superb side hustler, you will want to gather all of your receipts that may be considered business expenses.

Depending on your unique tax situation, you may have more forms to include. On the other hand, some of these may not apply to you at all. The key is to get all of these forms in one place so that you have them readily available when doing your own taxes.

Typically, your bank or student loan servicer will notify you when your forms are ready and you can download them from your account.

Pick a Tax Software

Once you have all your info, pick out a tax software to get started. As I said, we used TaxAct and it was pretty straightforward and easy to use. The instructions are clear, and if you have your paperwork ready, you just plug in your numbers as directed.

Make sure you understand any fees or fine print before choosing an option. The cool thing about TaxAct is that they have a price match guarantee to ensure you’ll get the lowest price. Score!

Once you pick a tax software, carve out at least 30 to 60 minutes to complete your taxes. To make it more fun, put on some good tunes, get some coffee and JUST DO IT.

Once you submit your tax return, you’ll feel a huge weight off your shoulders! Either you’ll owe or you’ll get a refund. I ended up owing this year because I made good money last year and didn’t quite pay enough in quarterly estimates (that’s right, self-employed folks get to pay taxes FOUR times a year!). My boyfriend ended up getting a $1,300 refund, which is great.

If you do get a refund, I recommend getting direct deposit so that your refund can go straight to your checking account. Cha-ching! That way you’ll avoid any mail drama and you can get it even faster. Wondering what to do with your refund? I recommend taking $20 out for “fun money” and then save and pay off debt with the rest. How is that for some balance?

Why You Should Do Your Own Taxes

If you’re an employee with minimal tax paperwork, you can save big by doing your own taxes. You don’t need to drop hundreds of dollars on help when the tools are out there for you to do them yourself. You don’t need to worry about messing them up so long as you read the prompts carefully and double check your work.

In addition to saving money, doing your own taxes can empower you to understand your finances better. You’ll understand just how much money you made last year, how much you paid in student loan interest and more. Knowing the numbers can be eye-opening and help you get a more accurate picture of your finances.

Beating the tax deadline doesn’t have to be stressful. With TaxAct, everything you need to confidently prepare and e-file your taxes is right at your fingertips. You got this. File your simple federal and state return FREE today with TaxAct.

This post is in: taxes

Hey everyone! We have a great dear debt letter from Dr. Joseph Chiweshe. Dr. Chiweshe is finishing his residency as Preventive Medicine Physician with a Master’s in Health Management and Policy. He is Founder and Chief Editor at MedSchoolFinancial.com where he writes with a focus on personal finance, health and the business side of medicine. Connect with him via Twitter @ChiwesheMD

Dear Debt,

It’s been real, but it’s time to move on.

I fully understand that if it weren’t for you that I may not have had the opportunity to travel along the path I’m on thus far.

However, over the years you continually grow and continue to request way more than we ever initially bargained for, and with your compounding interest, I see clearly that the only “interest” you have is in your own well-being.

What’s worse, is you grow without remorse and you would think after reaching a certain point, like the price of what many would consider a very nice home, you would be content but unfortunately that is not the case.

And as if that weren’t enough, the insidious nature in which you slowly took more chairs at the table where I sit and make important decisions for not only me but those I love was definitely never part of the deal, thus it’s time to go.

However, for what it’s worth, there are no wasted experiences in life, so thank you for teaching me lessons in finance, credit, wealth, and the knowledge I have acquired in health.

Thank you for spurring the ingenuity to start MedSchool Financial as a way for me to adhere to my mission of making a positive difference in helping others lead healthier lives with better financial literacy.

In addition, thank you for the opportunity to connect and share with others, like Melanie and the DearDebt community as we all bid you farewell and move on.

Undoubtedly, I know you won’t simply go without a fight. But as we part ways, there is a good quote I would like to leave you that may help you keep perspective: “life is short, even at its longest” and thus as you can see, you are fresh out of time and although it’s been real, it’s time to move on.

Best regards,



This post is in: dear debt letter

April 4, 2016

I’ve been back in Los Angeles for a week and I can already tell my whole mood has shifted. I’m happy to start the day, throw on jeans and a t-shirt and go for a walk to the local Starbucks to work.

In Portland, I often dreaded getting up. The weather had a severe effect on my motivation and productivity. Sometimes I would just stay in the house for days, hoping it would get better. When I first moved to Portland everyone told me I’d get used to the weather and get over it. I never did. That, coupled with the fact that it never felt like home, I always felt sort of out-of-place and was never quite at ease. Though I made friends and had some great times in Portland, it just wasn’t meant for me in the long run.

I can see now how much I needed this change. This change of location, in just one week, has had an immense impact on my productivity and happiness.

I’m becoming that annoying person that posts how happy they are on social media, because I really am happy to be back here.

It’s funny. Six years ago I left LA vowing I’d never come back. I was sick of the traffic, the smog, the people. I left for New York and had my love affair with the city for a while, before moving to Portland to be with my partner. For the first couple of years when we’d visit family here, we thought, “Glad we don’t live here!”

It wasn’t until the past year or two, that we started to shift. The six years away changed our perspective. We had new eyes to see LA. And as we have changed in six years, so has LA. The things that Portland could not give me (namely sunshine, diversity, arts and culture) LA could.

It started to become an attractive option. My boyfriend, who is a musician, also was feeling like he hit a ceiling in Portland…so LA made sense for him, as the music industry is great here.

I know that I’m in the honeymoon phase right now. Things still don’t seem “real”. I still feel like I’m on an extended vacation — part of that is because we are staying with my partner’s parents for at least a month, so we don’t have a place to call our own yet. We decided that would be best while he looks for work and I travel to Italy in two weeks.

But even though we are in a transitional phase and we don’t have a place to call our own, it still feels like home. LA feels right. It feels like I belong.

I’m excited to start the next chapter of my life. I wanted to update everyone on where I’m at and also remind you of why it’s so important to get out of debt — so you can afford what you truly want! I stayed in Portland for six months longer than I originally planned because I knew I could be debt-free before moving. And let’s face it, moving is expensive.

Between rental cars, hotel stays, food on the road and more we’ve already paid close to $1,500 to get here. Then we’ll have to pony up for higher rent, security, furniture and all that jazz.

It’s a lot of money. It makes me feel a little uncomfortable, but I know I made the right decision. I truly believe I will be able to earn even more money because I’m happier and more productive here. It’s a bigger city, with hopefully more networking opportunities, which could equate to more money. I’m confident it will all work out and even though my money situation will not be “normal” for a little while, at least I’m not sending multi-thousand dollar payments to debt.

Even though we’re slowly settling in, I can’t get too comfortable as I’ll be on the road in two weeks. I’m going to Italy the second half of the month with my mom! I’m so excited as this is one of the main inspirations for me becoming debt-free. My mom has never been to Europe and I’m so excited to go on this adventure with her. It’s a bit scary as I’ve let all my clients know I won’t be available for two weeks. Last year when I went to Spain and Portugal, I worked here and there. This time, I’m not working at all. It feels weird and scary, but I want to be present with my mom and not be working.

So pretty much I’ll be working like a fiend before and after my trip, but it will be worth it. Here’s to hard work and new adventures! The start of a new chapter!

What’s new with you?

This post is in: end of month update

Happy Friday! We have another dear debt letter for ya. Markita from Shewasdebtful.com is currently working her way through her student loan repayment plans while holding herself accountable to paying off debt. 

Dear Debt,

Do you have any idea what you’ve done to me? You remind me of my last relationship, where I kept running back to them, even though they treated me like crap.

Was it their fault that I sought the normalcy of the relationship? I say no. I got used to the treatment, but like that relationship, I am calling it quits. With them and with you.

There will not be anymore tears of frustration looking at the overwhelming number for two degrees that have yet to help me get a full-time professional job.

My depression will not stem from the knowledge that I will have to pay for 10 years worth of debt plus interest well into my 30s. Something that I promised myself I would NEVER do.

Freedom. I was doubtful that I could see the end of the tunnel, but just having the vision is already making me feel elated and confident that the future struggle will be worth it.

The credit cards are done too. My car will be paid off and any future large purchase will be paid in full. What, no house? Not in the near future.

Because you see debt, I plan to travel. By myself or with friends. Not with you or any form of you. I’m gonna be free from you and the chains you hold on me. It will all be over. I choose to move on. I choose to be free from you, debt. It will happen.

Markita from Shewasdebtful.com

This post is in: dear debt letter