Blogiversary: Double Debt Single Woman Turns 5 Years Old

On Nov 21, 2012 I made my first post. The picture on that post really reflected where I was with regard to my finances. I was beaten down, overwhelmed, and lost. I guess I started this blog as a way to vent my frustrations with money. (It has certainly served that purpose over the years!)

It’s hard to believe that I’ve been blogging for this long.  Happy Blogiversary, DDSW!

A number of things have changed for me and for my money in the past 5 years.

5 Things That Have Gone Well

ONE. Since beginning this blog, I’ve paid off nearly $80,000 of debt. My total debt has dropped from ~$142k down to ~$63k.

TWO. I now have $10k in savings (a safety net).

THREE. I became ‘worthless’ (hit $0 net worth) and then crossed over into positive territory for the first time in my adult life.

FOUR. I was quoted in a few articles relating to carrying large amounts of debt:  MarketWatch | New York PostStudent Loan Hero. I was profiled in Less Debt More Wine’s Student Loan Conqueror Profile Series.  Plus, my post about reaching Net Worth $0 was featured on Rockstar Finance. Pretty cool stuff!

FIVE. Financial fallout aside, I was FINALLY able to take an international trip, my first in over 10 years. Woot! It was amazing! And now that I’m getting some traction on my debt and finances, I plan to travel much more often in the future. In fact, I’m already planning my next trip.   Read More

[-$61,835] 3 Things I’m Thankful For

I have some things to be thankful for.


Another student loan payment made. Now down to $61,835. So close to being out of the 60’s now!


I received a gift of money from a family member in the sum of $3,500.  I have added this money to my emergency fund, which raises my balance to a perfectly even $10,000!

I’m not comfortable accepting money from anyone, which is part of the reason that I’m not spending this money or putting it towards debt. I’m keeping it in savings and accessible to give back if needed. This is not ever likely to happen, but it gives me peace of mind.  Now that my e-fund is at $10k, I’m going to stop contributing money there and put those future dollars towards clearing out the credit card debt.   Read More

[-$63,453] Not Halloween Anymore, but Still Scary

Seeing my balance creep HIGHER these past couple of weeks has been scarier than Halloween was.  Even more scary is that I am now carrying a credit card balance again! Yes, I know.  😦

For my 2018 trip, I have most of my big ticket expenses (airfare, hotel) booked already, hence the card balance. But there is more to go. First order of business is paying the card off, of course.

I started having some tooth discomfort and was back in a quandry about whether I should go back to my old dentist, even though you guys told me to ditch him and find a new dentist. Well, as it turns out, I discovered that my old dentist recently retired and sold his practice. The new person there doesn’t have any skill or accomplishments presented that make me want to stay. I feel free, like I’ve escaped a bad relationship. LoL. I don’t know why I stayed for so long. Read More

[-$63,299] Falling Off the Track

I’ve made my required monthly $1,720 student loan payment and now owe $63,299. The balance looks practically unchanged to me compared to before the payment. Sigh.

However, when I get my next paycheck in a couple of weeks, very little of it will go toward debt at all instead of my target of $1000 extra. Why?

There are three things that are contributing to drastically slowing down my debt repayment, for the next few months at least.   Read More

Student Loan News: Earnest Acquired by Navient

If you have a student loan and are looking to re-finance with Earnest, or already have refinanced with them, news broke today that they have just been acquired by Navient for $155 Million.

Read about it here (BizJournal), here (Wall Street Journal) , or here (Earnest Blog).

Earnest, has been a popular financial technology startup since it’s creation in 2013. Like SoFi, CommonBond, and other such lenders, Earnest uses technology and data analysis to identify lower risk borrowers in ways that were not readily available in the past. This kind of lending model is a lucrative area that Navient has been eyeing for a while.   Read More

[-$64,900] Deficits & Daydreams

This is now the second month that I’ve paid less than my target bi-monthly payment amount. As I mentioned in this post, I have a mid-month payment that is required by my servicer, but I also have an end-of-month surplus payment that I use to pay extra on my loan. My end-of-month target payment has been $1,000. So far this year, I’ve managed to hit that  target, until recently. I’ve been having a long standing battle with overspending my budgeted allowance. It’s a battle that I’ve clearly been losing.  Read More

[-$65,348] Data Breach Edition

I’m feeling exhausted and in need of a break. Not just a break from work, but I also need a financial break. Like over 140 million Americans, I’m simultaneously infuriated and apathetic about the Equifax data breach. I’m furious that Equifax (and likely their competitors as well from what I’ve been reading) can be so lax in their data security.

On the other hand, I’m also numb and jaded given that I’ve already been affected by multiple large breaches already (university, state gov’t, retailers, data companies). My social security number has been compromised so many times, it doesn’t know which way is up anymore. And this Equifax data breach is the worst of all.

These organizations and corporations never appear to face any consequences. Needless to say there is something wrong with this. Companies that can profit from their own lax protocol and data handling will never have any incentive to do any better. They are like bad student loan servicers that misplace paperwork and neglect proper record keeping, then profit even more from the resulting slew of borrower defaults. Read More

[-$66,952] My Health Sinking Fund Has Sunk


Short post today, as things are hectic with work. I am looking forward to the long weekend!

Instead of my customary $1,000 payment at the end of the month, today I only put $700 towards the student loan. Why? Overspending in my budget. In particular, I’ve been spending a lot of money on health care. My health fund, which I funded at an unusually high $2.5k early this year, is already exhausted.

The bad news is that all of these tests and supplements are expensive. Thus, my health fund, a sinking fund, has sunk.  Read More

[-$67,520] Making Hay While the Sun Shines

Why do I make such large payments on my student loan debt? Because, for now at least, I can.

In the past month, I’ve dodged a bullet that would have raised my rent by over 50% (losing a new roommate because of discord in the house). So far the climate in the house is improving. I’m really hoping it continues.

I’ve always known, and written here, about how my cheap (for this area) rent will not last. At some point in the future, LL (landlord) will stop… landlording and we’ll all have to leave. When that happens, my rent will go up significantly as soon as I move anywhere else. So I must pay as much as I can now  toward this debt, while I have this cash flow. In other words, I have to make hay while the sun shines.  Read More

[-$69,127] Another Public Transit Rant


If you look through the window, even the guy on the next train is like, “Really, chick?!”

The woman in the red shirt is just … over it. I can so empathize right now.  It’s time for another public transit rant.

I’ve written before about public transit. I am, of course, very grateful for the convenience, but I pay more than one price for it.  Here are some things that I deal with… If you also take public transit and recognize these things, feel free to sing along…

If you don’t take public transit, run outside and kiss your car right now. RIGHT NOW, I said!  LoL.

Read More