November 25, 2015

Hey debt fighters! Today’s dear debt letter offers a fresh perspective, from someone who has to clean up debt’s mess. Today’s letter is from Ted Michalos, a bankruptcy trustee and co-founder of Hoyes, Michalos & Associates Inc. Hoyes Michalos was founded as a firm that takes a respectful and personalized approach to debt management and recovery, to help people gain a lasting fresh financial start.

Dear Debt,

We need to talk.  I’m the guy that has to come along behind you and clean up the mess you create. Credit is a “good” thing – we congratulate people for having achieved enough status in their life to qualify for credit.  Unfortunately, as soon as someone uses credit it turns into you, Debt.  And sorry, but you sir are “bad”.

I am not holding you wholly responsible – there is more than enough blame for everyone involved, but someone needs to warn people about you.

You start out harmless enough.  A person qualifies for their first credit card or loan.  You make them feel so proud, so grown up. However, from that magical moment forward you put them at risk of having you take over their life. Until the card gets used there is no debt, so there is no problem, but you’re always waiting for your chance to grow. You entice them with the concept of having it all now, and you’re pretty quiet about the cost.

Here’s the thing that you don’t remind them about, so I will – credit should be a replacement for cash. It is not a replacement for money.  You should only use credit when you have sufficient money to pay off the balance so Debt doesn’t find you.  If you don’t pay off the balance every month then Debt takes over and he asks for something in return. He charges interest.

Interest is the cost of using someone else’s money – the cost of incurring debt.  The truly crazy part (of course you know this Debt) is the more debt a person has the more expensive the interest charges become.  So just when a person needs a break or a little help, you tell them, “sorry, but you owe so much now that I’m afraid you may not pay me back.  I’m going to have to charge you even more to use my money…”  Shame on you.

Why am I writing you this letter?  What do I want you to do?

I guess I’m just venting.  You won’t change.  The only solution is to change the behaviour of your consumer.

The problem with this is our entire economy is built around the use of credit, the incurring of debt.  The newest greatest gadget comes on the market and people want it today.  No money?  No problem.  You slyly pre-approved them for more credit.  It’s your way of keeping people tied to you.   You must be proud of yourself – you’ve done one helluva job getting everyone onside with your program.

I thought after writing you this letter I‘d feel a little better – I don’t.  Tomorrow I know I will have that senior citizen couple in my office that incurred a bunch of debt to help their family members out, and you’re not really there to help them.

I’ll get to see the single mom that incurred a bunch of student debt to make a better life for herself and her children, only to find out, she can’t earn enough to make you go away and pay her living expenses each month.  Or maybe it will be the guy from the plant that has had all of his overtime cut.  He was living the good life based on the overtime never ending – now he makes 25% less and you want a bigger share of the pie.

Well, hopefully just one person reading this will be wary of you Debt; before it becomes too late. Before you consume so much of their pay that they are one of the people I meet with every day. Perhaps we can tackle you with education, one person at a time.


Ted Michalos,

Co-founder of Hoyes, Michalos & Associates Inc.

Debt Management Experts

This post is in: dear debt letter

Hey everyone! Today we have a fantastic dear debt letter from Latoya. Latoya is a wife and mother of two who lives in Columbia, SC.  She is working towards paying off $79,733 in debt to be exact. Her goal is to be finished paying off her debt within the next 5 years.  Latoya is a freelance writer for hire who writes at Life and a Budget about life and money.

Dear Debt,

I really can’t stand your ugly ass.

You weigh me down and cause me unnecessary stress.  I think about you all the time when there are much better things to be concerned about.  I wonder what I’ll feel like on that special day when you will no longer exist in my life.

The day your ugly ass can no longer call a place in my life home, will be the best day ever.

You lured me in with your enticements when I was only a baby.  Fresh outta high school without a dollar to my name, you made me fall in love with you.  I’ll admit you had me whipped.  Had me acting a fool over you.  I loved you hard.  You supplied all of my young needs.  I was so eager to use you – never thinking of how I would pay ten times over for enjoying the temporary pleasure you provided.

I had no protection from you.

I didn’t know what I was getting myself into because I wasn’t taught any better. In school we’re taught to protect ourselves from unwanted pregnancies and diseases, but taught little about your ugly ass and how you can taunt us for decades if we don’t take precautionary measures against you.

If I’d known what I was up against, I could have prepared mentally and financially.

The income from my summer internships wouldn’t have been wasted on providing you with your minimum monthly maintenance.  I could have invested that money and watched it grow.  I could have practiced the art of self discipline.  Instead, I’m trying to teach my 31-year-old self tricks I could have learned years ago.

Half of the stuff you brought into my life I didn’t even need. College students didn’t need the latest from Victoria Secret, Foot Locker, or Macy’s.  The only thing I needed was my mind and the education which I set out for.

Anyway, I’m tired of your ugly ass stalking me.

I have become exasperated by your ability to multiply even though we aren’t cool like that anymore.  I want you to leave me alone and I’ve decided to do something about you. I’m coming for you.

I’m an ex-lover scorned and I can’t wait to annihilate your ass.  The clock is quickly winding down on your ass, so I hope you’re prepared.  You can’t do this to me anymore.  I will not let you have anymore of my present or my future.

I hope you’re prepared to say goodbye. The day is coming quickly and there isn’t a thing you can do about it.  Got any questions?  I hope not because I’m no longer answering to you.


This post is in: dear debt letter

If there’s one thing that’s for sure, I definitely lean more on the ‘earn more’ side of the personal finance spectrum, rather than the ‘cut back’ side. I see the value in both, and in tandem, they can be a powerful combination.

But lately, I’ve been focusing my side hustle energy on scoring cool things for free. It feels weird, because it seems so unlike me to spend time on trying to get things for free. It’s not like I’m spending all day on Swagbucks  (affiliate link) trying to earn a Starbucks gift card or anything, I’m spending maybe 5 minutes a day or less.

I got interested in entering giveaways when a music festival was happening over the summer and I couldn’t justify the expense. So I decided to enter a giveaway for tickets. And I won!

This summer I won, not one, but two giveaways to music festivals. I don’t talk a lot about music on this blog, but music is my one true love. I live on music. I can’t work without it. There’s a reason I’m obsessed with karaoke and singing (which some of you saw at FinCon14) and dating a musician. Music is electricity for my soul. Sadly, while paying off debt, I haven’t budgeted a lot for it until recently.

I won two tickets to MusicFestNW and Project Pabst and got to see Weezer, Blondie, Run the Jewels, Thee Oh Sees, Modest Mouse, and more. It was a blast! I did the math and those two giveaways were worth $450 (they were multi-day festivals).

I won them via PDX Pipeline and from what I know, it’s NOT a random drawing and people pick you based on your comment. Which means you have to be more clever than just saying “Pick me!”

My first winning comment went for the heart-strings. I mentioned that my boyfriend and I hardly see music together, as I’m almost always watching him play music. I mentioned that his birthday was coming up and it would be great to spend it together and enjoy a true passion of ours: music.

Not even three weeks later, I won again. But this time for a purely ridiculous comment.

I said, “If I don’t have more live music in my life, I’m going to spontaneously combust!”

While we were at this festival, we ran into one of Ryan’s musician friends who told us about Tixie, another ticket giveaway site.

Tixie gives away concert tickets and local drink and restaurant tickets. They give you ten “coins” a day and you can “spend” them in a certain category. The more coins in a certain category, the greater possibility that you will be randomly chosen.

This week, I won a $25 gift certificate to a fun cocktail bar that we’ve only been to once. Score!

My point in all this is you could score big on giveaways that are worth it to you. Don’t spend all your days and nights entering giveaways, because it would be cheaper to just earn more in that case. But I’ve literally spent 2-5 minutes per day and gotten close to $500 in free entertainment!

Now, my turn to spread the giveaway love. I have a free pass for a newbie to go to FinCon next year. The code is only valid for people who have NOT been to FinCon before. If you are interested in heading to San Diego next September to go to FinCon and you think it would change your life (because it totally changed mine), share this post and write in the comments below why you want to go to FinCon and what you’d get out of it.

Our panel of very biased judges will email the winner 😉

This post is in: Uncategorized

November 18, 2015

Hey debt fighters! We have another great dear debt letter by Chonce who blogs at My Debt Epiphany. Chonce is a personal finance freelance writer and blogger working her way out of $30,000 in debt. You can follow her on Facebook or Twitter.

Dear Debt,

You’ve officially trapped me. Everywhere I turn, I see you. If I want to move forward, I need to get past you. You lured me in with fantasies and dreams of a more fulfilling life. Once I took the bait, I realized only I can make my life more fulfilling and worthwhile.

I can’t blame you completely though. I am part of the problem as well. I tried to take responsibility. I tried to go over you. Tried to peek around you to see what would await me on the other side but you pushed back with a remarkable force.

I’m trapped by you. Every time I try to break free, I feel you tugging at my arm as if we are in this together…As if I need you to survive and make it.

When you’re trapped for a while, you start to lose hope and forget what your life was like before you fell under. You start to settle and believe that things will never change. You may even consider giving up the fight.

I have heard stories of people who broke free from the trap and I believe in life after debt.

So dear debt, my message for you is to enjoy your time. Cherish it actually. Because the harder you try, the harder I will try. I promise you I won’t be trapped by you much longer.


Your best-frenemy, Chonce

This post is in: dear debt letter

I know many of us are already thinking about 2016 and planning to make it our best year yet. I am too. At the top of my list? Making more money and continuing to rock my freelance career.

I’m going to put it out there — even as scary as it seems — but I’m gunning for six figures. That’s what I want, and it’s not some arbitrary number. It’s a number that I know will help me pay off the last of my debt (currently at $11,700) and will help me catch up in other areas of my financial life, namely investing. It will afford me peace and comfort and help me accomplish my dreams.

While six figures still seems far away from my current income, I’m a hell of a lot closer than I was last year, or any previous years.

Times Have Changed

Three years ago when I started this blog, my net income was $20,000. I struggled more than I ever had to get by, and it was a truly humbling experience. Now, I’m super proud that this year alone I’ve paid off $20,000 in debt!

I’m not saying this to brag and never want people to think that’s what I’m doing. I’m sharing because I want people who are currently in the same situation to know what is possible. If it weren’t for so many others that showed me the way, I would have never known that freelancing full-time while paying off debt is possible.

But it is! And you can totally rock your finances being your own boss — even with the erratic income. I’ve found that being my own boss has been the only path toward building wealth.

Here’s the thing, though. So many people still believe that they’re meant to be a starving artist. Asking for money, or even wanting money, is dirty and bad. It feels like it’s tainting our work and spoiling it. But let’s be real. All of our work — especially our creative work — is of value. It’s time, resources, heart, and hustle. You deserve to get paid for your work.

And I want to help you. I’m so excited to announce that I’ve partnered with to teach creative professionals how to manage their finances and pay off debt.

The Workshop

The workshop will be over three days, January 4-6 at 7pm EST, and for one hour each night, we’ll be going through how you can manage your money, ask for more money, and build your network so that work starts coming to you.

I’m so excited to get back to teaching and share what I love! The best part? I have a killer deal for you. The workshop is $97, but with the discount code DearDebtVip, the workshop is only $37. This code is only valid until December 1.

Let’s break it down — with the discount code, that’s about $12 per hour for each class. Even with the full price, it’s only about $32 per hour.

My Passion and Pursuit

So, why am I so passionate about this? Or why am I even qualified? Because in the past year, I’ve more than doubled my income and paid off more than $20,000 in debt. I’ve learned the hard way about working for peanuts and sticking to low-paying work just because it was comfortable.

For some perspective — as recently as February, nearly all my clients fell into the $25 to $75 range. I was writing like a fiend and cranking things out. It didn’t feel particularly fun or useful, but I was “producing”. After a full month of working, I kept seeing that I was barely making $3,000 each month. After self-employment taxes and paying for my own health insurance, I was barely competing with my old nonprofit salary.

I did the math. If I wanted to make $5,000, I’d have to write 100 articles per month at $50. That’s 25 articles per week. I knew something was wrong and that something had to change. After looking everything over, I knew I was going after the wrong clients and the wrong pricing.

So I made a lot of changes, got rid of four clients in one month and relentlessly pursued higher paying clients. With a lot hard work, motivation, and branding, it worked. Now nearly all of my clients are within the $200 to $400 range (for one article).

I am living proof that you can make money being your own boss, and that you can make changes quickly, with a few small, but powerful shifts.

Now, I want to help others make more money and rock their finances. Freelancing doesn’t have to be feast or famine. You don’t have to be a starving artist. You can be a #Girlboss (or #Broboss?) that makes what you deserve and live a life you never expected.

I sure didn’t expect any of this when I was on food stamps three years ago. But I’m beyond grateful and have learned a lot.

I hope that you’ll join me in this workshop. Use discount code DearDebtVip to get it for only $37. If it’s not your thing, please share!

Are you ready to rock your finances in the new year?

This post is in: creativity

Dear Debt,

How many seconds, days, months do we have left together? You know you’re on your way out and you’re trying to test me.

You want to make things hard for me. You want to see me squirm as I try to stay strong and get rid of you. You keep playing mind games with me, but I know you are just messing with me, because you’re the one scared of being alone.

I won’t deal with your crap any longer. I don’t care whatever you throw my way in the next few months, but I’m kicking you out.

Even if it’s the hardest thing I’ve ever had to do.

I am saying no to the depression you cause me. I am saying no to the anxiety and fear you have instilled in me.

I know I’m worth so much more than you ever had me believe. You did a good job of convincing me I was worthless, but I’ve gotten smart.

If there’s one thing I know about you, it is that you’re sneaky. You like to play tricks. But I’m done with playing games. You are a man-child and need to grow up.

I am older and wiser and I have changed, but you’re still the immature child I met when I was 17.

It’s time for me to move on and experience real life. Real adulthood. Not some stunted adolescence.

Good riddance.

This post is in: dear debt letter

Millennials entering the workforce may be overwhelmed with stress about the economy. In truth, the American economy is not in the same place that it was when older generations were entering the workforce. For this reason, it is key that millennials begin thinking about money differently.

Lack of proper financial know-how is affecting young people from all walks of life. It was recently reported that Wesley Edens, owner of the Milwaukee Bucks NBA team, was holding financial planning classes for his young players due to the high number of professional basketball players ending up bankrupt. While we don’t all have a coach to help us plan our financial futures, we can take some basic steps to begin building healthy money habits as soon as we enter the workforce.

Learn to Budget

Let’s face it, making money feels good. After your first month of putting in 40 hour weeks, that paycheck is burning a hole in your wallet. And while, yes, making more money means that you should be able to spend more, it is important that you think through how to spend it before going on a shopping spree. Before you receive your first check, it is vital that you create a budget.

There are many formulas for healthy financial living, but most will have you spending the bulk of your money on housing and food. After this comes transportation, debt repayment, and savings. Finally, you have entertainment, clothing, and medical expenses.

Based on your current salary and living situation, put together a budget that will allow you to know how much money you have each month to spend on each budget item. Then make sure that you keep up with your spending. You can do this manually or using a budgeting software. Mint provides a great free budgeting tool, which pulls information from your bank accounts and alerts you when you are spending too much in one budget category. Just like a diet, sticking to a budget will pay off big time in the long run.

Save, Save, Save

Saving money may not seem like a priority when you first start working, but it should be. As mentioned above, when you create your budget, you should have a line item designated to savings. In general, you should try to save between 10 and 30 percent of your salary each month.

You should try to save more early on when you have fewer expenses (such as a family or mortgage). Create goals for yourself to work toward. For example, you may want to buy a new car or put a down payment on a home. By creating savings goals, you can make headway toward these objectives without depleting your savings account or acquiring massive amounts of debt. Put your money in a savings account, which accrues interest and is not as easy to access for best savings results.

You should also make plans to begin saving for retirement as soon as you have a solid income. If your company offers a 401(k) or pension plan, go ahead and participate. You can decide how much you would like to contribute and it is taken directly out of your paycheck, making it a mostly painless way to begin saving. Your company also contributes to this account. The sooner you start saving for retirement, the better off you will be in the long run.

Be Sure to Pay Down Debt

While you definitely shouldn’t plan to go into debt, it is important to note the different kinds of debt you can have. Credit cards are not a great kind of debt. Generally, spending money that you do not have is never a good idea and can catch up with you.

Most people, however, do not have the money to pay for things like college. In this case, you may have to take out student loans. Luckily, when you take out student loans and you make consistent on-time payment, you begin to acquire points toward your credit score.

Your credit score tells banks how reliable you are at paying back money. The more reliable you are, the more likely they are to loan you money when you want to purchase your first car or home.

Using these three tips, you can build a solid financial foundation for yourself — so you can worry less and enjoy life more.

This post is in: Other

The holidays have arrived. Red cups are back and nearly all the stores are already filled with holiday-related swag.  Although my partner and I love celebrating with our family and friends and keeping things minimalist, maintaining my debt plan isn’t easy around the holidays. There’s so much pressure to spend and from my own perspective, I want to be generous.

But I’m so close to paying off my debt, so I want to keep my spending in check, while still spending some money to go see family and spend time with them. I spoke with the people at Canterbury Law Group and they suggest treating your holiday spending like a business (remember YOU are the boss).

So this holiday season, my plan is to stay on track and keep things frugal during the most expensive season of the year.  I created these five tips with some expert advice from the bankruptcy attorneys in Scottsdale.


  1. Strategize. Begin by creating a holiday spending plan. Decide how much you can afford to spend this season, including gifts, travel, parties, decorations, and any other holiday expenses. Make a shopping list with who you want to purchase gifts for. Determine how much you’ll earn between now and the holidays and decide how much you’ll need to set aside each paycheck to save the amount you will need.


  1. Track your spending. If you realize you don’t need to spend as much as you planned in some categories, move the extra funds to your savings. Or even better, pay off debt!


  1. Shop without your credit cards.  Yes, leave them at home unless you know you need them for a specific purchase and you already have a specific plan to repay the debt. You don’t want to accrue debt during the holidays, right? That is NOT the holiday spirit, my friend.


  1. Shop smart. Shop online first so you can price compare multiple retail locations.  It’s also wise to ignore most of those “big” sales.  In reality, deals such as “Buy 2, Get 1 Free” often leave you spending more and acquiring items that you don’t need. Remember, a sale is NOT an excuse to spend.


  1. Avoid purchasing on impulse. Instead, make a note of the product, where you saw it and how much it was. Only buy things on your list!

I’d love to hear from you! How are you saving money this holiday season?


This post is in: Other

Here we are at another start of another month. A new beginning. A fresh start. I’m excited to try to rock November and make some changes in my life so I can be happy, rested, creative and fulfilled.

October was not bad, it was just stressful and seemed to drag on. I felt like I didn’t have my head on straight. It was hard to focus and hard to stay in the moment.

I was always thinking of the future, or dwelling on the past, or letting Larry David get too far into my head. I’m trying to practice more mindfulness and gratitude and let go of perfectionism and OCD. It’s so very hard, but I know that’s what I need to do. Let go.

I think I have too much mental clutter. Though I espouse the benefits of minimalism and live with very little stuff, I seem to have a lot of mental clutter that needs to get disregarded.

I suppose some of it was exacerbated by the fact that October was an emotional month for me. It was my birthday month, which always gets me reflective in a certain kind of way.

In addition, there’s been some big changes for my family. My 93-year old grandpa recently moved from Michigan to live with my parents in California, after his wife passed away. That of course is a huge transition — but the good news is that I will now be going home for Thanksgiving for the first time in nine years, so we can all spend time together. I cannot wait as this will be the first time my partner will meet my grandpa, who I think is the coolest person ever.

In addition to that, I received some bad news about a friend that has affected me deeply. My friend is suffering from cancer. I am just in shock as they are not much older than me and it feels so wrong.

It’s in these moments that you really start looking at your life. I’ve been filled with questions that I can’t answer.

What is my purpose in life?
How can I live every day to the fullest?
Am I doing everything I can to be happy?

Yeah, I’m in total existential mode — which is why I guess I’ve been a bit quiet. I don’t know what to say. I don’t have the answers. Focusing everything on money seems silly when Real Problems arise.

But I’m moving along. I’m making things happen. Trying to find some balance in the hustle and enjoying all that life has to offer while keeping up with my debt repayment goals.

This month I put $3,300.02 toward debt. The two cents was to kill off the final interest on one of my loans! My current numbers:

Undergraduate loan: $4,791.52
Graduate loan: $9,171.08
Total: $13,962.60

I’ve been using the avalanche method of focusing on highest interest debt first. For me, the math just made sense. My undergrad loans were relatively small at 2.3% while my graduate loans had nearly triple the balance of my undergrad loans, with interest rates of 6.8% and 7.9%. In short, it was costing me too much money! At its highest, my interest was costing me $11 per day, so I knew that I had to knock this thing down.

My goal for the next two months is to continue paying off my debt at this pace and learn to relax and enjoy life. Try to be happier. I guess I also have a case of the blahs — the rainy season has officially hit Portland and the constant gray really does a number on me. Also, I’m not excited about it getting dark so early, but I have to remember that seasons change.

It’s time to turn a new leaf!

What are your goals this month?

This post is in: end of month update

Hey everyone! Today’s dear debt letter is from Keshna. She is from New Jersey and has a total of $40,882.95 in debt. Follow her blog/website,

Dear Debt,

You’ve followed me around everywhere. It’s time I let you go. You are like a dark cloud that I cannot escape. I can see the sun rays. I can feel the warmth. I’m leaving you and I needed you to know IT’S OVER! Many people are misinformed about you. They think there are good versions of you. You’ve fooled this designer enough. I am ready to start my business and I won’t let you hold me back any longer. Good riddance, goodbye, and I will never see you again!

P.S. I’m telling all my friends to stay away from you!

This post is in: dear debt letter