Lindsay VS her debt: Part 4 – BUDGET AHOY!!!!

Lindsay VS her debt: Part 4 – BUDGET AHOY!!!!

Budget Island

*The following is part 4 of a year-long series. If you want to start from the beginning, learn about who Lindsay is, and check out how much debt she started with…  check out PART 1.*

Well, friends, remember that time I was going to try and pay off over $1000 this month?

That didn’t even happen a little bit.

May ended up being a crazy busy month – it flew by before I realized it had even started. Along with it being busy work wise, I’ve found myself a bit, well… distracted as of late. So I didn’t budget. And then the month ended. And then I found out I only had $490 to pay towards my debt… so that’s where I’m at. UGH!

The amazing thing about failures is that they have the ability to become amazing learning experiences. The biggest thing I learned from last month, is that I seriously… SERIOUSLY! need to use a budget.

I’ve been using YNAB (à la Chris) for about 8 months or so now, and I use it fairly consistently. To be honest, I thought it was a good thing to have, but I didn’t really understand why it was important. (I’m on top of my finances because I use budgeting software! Look at me! Gold star!)

I basically never stick to my budget. I constantly adjust and move amounts and overspend – it’s pretty much always in flux. So if I was adjusting it all the time, it really didn’t matter that much, right?

WRONG!!!! (more…)

Lindsay vs Her Debt: Part 3 – Breaking all the Rules

Lindsay vs Her Debt: Part 3 – Breaking all the Rules

Lindsay vs Her Debt - From Rags to Reasonable

*The following is part 3 of a year-long series. If you want to start from the beginning, learn about who Lindsay is, and check out how much debt she started with…  check out PART 1.


Hello again, friends! I can’t believe two whole months have gone by since I started. Time flies!

Today I wanted to talk a bit about my debt paying strategy, why personal finance is personal, and why I’m breaking the rules. I feel like a bit of a debt paying bandit!

Somewhere out there, Dave Ramsey just had a chill up his spine, but has no idea why…

Anyway! Let’s start from way back at the beginning, because to me it’s extremely important that if you ARE going to break rules, you need to know:

  • that you’re breaking them, and
  • why you’re breaking them.

Why I’m breaking the rules:  (more…)

Lindsay vs her debt: Part 2 – Debt-free without the deprivation

Lindsay vs her debt: Part 2 – Debt-free without the deprivation

Debt-free without the deprivation - From Rags to Reasonable

*The following is part 2 of a year-long series. If you want to start from the beginning, learn about who Lindsay is and check out how much debt she’s starting with…  check out PART 1.

Alright my friends! The first month of my debt-paying challenge is over, and let me tell you, it’s been a roller coaster.

Like the start of any good financial challenge, it began by my going on a 4-day juice cleanse, and taking a purely personal trip to New York City for my birthday.

Wait… what?! (more…)

Lindsay vs Her Debt: Part 1 – the $12,372.95 challenge

Lindsay vs Her Debt: Part 1 – the $12,372.95 challenge

*This is a guest post by fellow artist and financial tinkerer, Lindsay. Here’s part one of what will be a 12 part series tracking her debt repayment process throughout the year. Enjoy!*

Hello friends! I’m Lindsay. I’m a singer, and I want to share a huge goal with you: I intend to pay off my credit card and line of credit debt by the time I turn 30. (SIDE NOTE: I turn 29 in like, 2 days.)

Lindsay is a singer, almost 29, how wants to pay her debt. Her debt is 12, 372.95

Now, this isn’t my first time attempting to pay off debt – I actually knocked out a pretty significant chunk (around 15k) about a year ago, but the way I was doing it just didn’t line up with my values. 

I was EXHAUSTED.  (more…)

8000 reasons you should go see your dentist … right now

8000 reasons you should go see your dentist … right now

8000 reasons for the dentist

I celebrated an anniversary two weeks ago… The anniversary of last year’s disastrous American thanksgiving, when a slightly sensitive tooth flared up into a full-blown infection leading to the first of what would be many dental procedures over the next 12 months.

You see, for the 10 years before that date I had been avoiding the dentist.

Some of my favourite excuses were:

I know there’s stuff that needs to be done, but I don’t have the money.
It doesn’t really hurt that badly.
I don’t really need my teeth… I can just live off of milkshakes… they’re good…

But the truth was, I was just pretty scared of the dentist. Ever since I was a little kid, I hated it there. The sounds, the smells, they just made my muscles tense up.

Plus…there was the money thing…

So it was an occasion worth celebrating when, a year after that first root canal, I was CAVITY FREE for the first time in years. I had bitten the bullet, gotten the work done… and doggone it… it was worth it.

Well done, past Chris, you’re finally growing up into an adult.

And the very next morning after my joyous anniversary I woke up with a terrible toothache… (more…)

ARTIST 2 ARTIST: HOW I PAID OFF MY DEBT… BY TAKING ON MORE DEBT

ARTIST 2 ARTIST: HOW I PAID OFF MY DEBT… BY TAKING ON MORE DEBT

How I paid off my debt by taking on more debt- From Rags to Reasonable

Lots of artists have lots of debt. But tons of those artists are managing to pay it back, all while living this crazy variable life.

I recently put out a call for artist debt stories and got this email that I just had to share.

Meet Charlotte. She’s a Canadian opera/musical theatre singer based in Toronto. This is her debt story…


“It’s an unconventional debt repayment story – I paid off all of my debt by taking on more debt – but it’s worked out beautifully and given me more stability and peace of mind than I ever thought was possible while still pursuing a full-time performing career.

The short version is this: four years ago, I was freelancing and working part-time at a law office – and I felt like I was drowning in dept. In 2008, I graduated from Western with $26,000.00 in student loans. By 2011, my student line was still sitting at $18,000.00 – due largely to the constant strain on my income from continuing to re-invest in my developement i.e. summer program tuitions, lessons, coachings, travel expenses, audition expenses, etc. I also still owed my parents $4,000.00 and my credit card was maxed at $1000.00. Eeek.

So I bought a house.

With ZERO financial backing from any outside source (not even a mortgage co-signer), at 25 years old, with an annual average income of $24,000.00 gross – I bought a rental property.

In four short years, my rental income has paid off the following: my student line, my parents, and all of my consumer debt – not to mention it also pays my mortgage and all operating expenses (property tax, house insurance, utilities, maintenance and updates, etc.)

I wasn’t simple by any means – it took a LOT of creativity and hard work – but really anybody could do it.”

– Charlotte


I was super fired up by her awesome solution to her debt problem… I also had a ton of questions. (more…)

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