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.

5 Things That Have Not Gone Well

ONE. A few months after starting this blog, I lost my job. I was on unemployment for 4 months before I found another job. Moving to a high cost of living area for said job also added expenses. It had the effect of delaying any debt repayment by almost a year. It wasn’t until November of 2013 that I was able to really start making progress on my debt.

TWO. Sacrifices that I have had to make to kill this debt include living with roommates. I’ve written about this here, here, and here (among other posts). (I REALLY want my own place.)

THREE. I fell ill and had to have major surgery a couple of years ago, which set me back financially. I believe the trigger/accelerant for this illness was the extreme stress and poor diet I had after losing my job with so much debt around my neck and the subsequent downgrade in my standard of living. I’m still monitoring my health because all of those factors are still present (albeit to a somewhat lesser extent as I get used to this way of life.)

FOUR. Within the past few months, I’ve slammed into a wall of ‘Debt Fatigue’. I’ve gone back into (temporary) credit card debt while booking travel related purchases for my upcoming trip. In order to pay the credit I’m halting my extra monthly payments and only paying the $1720 minimum due every month.

FIVE. I’m still single AF. The title of this blog will never let you down on that front, it seems.


5 Things I’d Like To Do/Have Within The Next 5 Years

ONE. Be completely debt free!

TWO. Have $30k cash in an Emergency Fund.  (My hammock)

THREE. Have at least $300k in retirement savings and investments

FOUR. Have my own place to live! Preferably near a good gym and grocery store. No roommates!  My OWN kitchen.  Ahh, to dream…

FIVE. Have a couple of solid, researched, and viable business/second income ideas that I can fund/get funding to launch.

I thought about putting ‘Be in a committed relationship’, but I decided to only list things that are entirely within my control.  The hope is still there of course.


Thanks for hanging out and celebrating my blogiversary with me! I’ve so appreciated your comments and words of advice and encouragement over these past five years. Thanks for sharing your own experiences. It helps me to know that I’m not the only one in the battle.


“Debtor’s prison is real, and opportunity cost is a bitch.” (DDSW Archives)



  1. Jena · November 28, 2017

    Wow! 5 years blogging is pretty awesome! Thank you for sharing your journey with all of us on the interwebs… 🙂


  2. Solitary Diner · November 28, 2017

    That’s a huge accomplishment! Congratulations on making so much progress in a relatively short time, even though I’m sure it seems like it took forever. Looking forward to hearing about you progress over the next five years.


    • Double Debt Single Woman · November 30, 2017

      Thanks! I just read your post about resisting the tendency to nest and can totally relate. Will be checking out more posts. 🙂


  3. Fiscally Fit Chica · November 28, 2017

    Congrats! I’ve loved reading about your journey!!,


  4. zeejaythorne · November 28, 2017

    Woohoo! You’ve shown such dedication and made incredible progress! I hope you continue to celebrate yourself.


  5. Akiko · November 29, 2017

    Haha. I am still single AF too. One of my goals was to be DF or near when I get into my next relationship. But this journey is taking longer than expected (health too). I better get my debt moving or I will remain the cat lady.


    • Double Debt Single Woman · November 30, 2017

      LoL. When I hear women say that they are taking a break from dating and relationships I just don’t understand.
      Where are they meeting all these people? It’s completely foreign to me.

      Liked by 1 person

  6. Amanda @ My Life, I Guess · November 29, 2017

    Happy Blogiversary! You have made so much progress in the last five years, I’m sure you’ll achieve even more in the next 5 years. 🙂


  7. nicole · November 29, 2017

    Congrats on your 5 years! I do hope by blogging you realize how far you have come. What a great way to track your progress.
    You will reach all your goals. I am certain of it. Now, to write my own next 5 year goal list. Thank you for the idea!


  8. Maria · November 30, 2017

    Happy 5th blogiversary! I enjoy your blog so much. 🙂


  9. Michelle · December 1, 2017

    Wow! You have done so incredibly well despite those setbacks that you outlined! Way to go! I am also single af and at 35 its becoming a bit concerning- but i remind myself that when the time is right the right guy will come into my life.


    • Double Debt Single Woman · December 7, 2017

      It’s good to keep a positive attitude about it. 🙂 There are so many other things to keep us down…


  10. C@thesingledollar · December 6, 2017

    You’ve come SO FAR. I reread a few of your early posts and your situation now is just infinitely better. Whee!


    • Double Debt Single Woman · December 7, 2017

      Yeah, whee indeed!! 🙂 Things are looking up! When I first started writing this blog, I couldn’t even imagine paying off $80k of debt and what it would take. Having this blog helped me stay accountable. I haven’t been perfect, as I’ve documented, but I’ve stayed truer to the course of debt payoff than I would have if I didn’t come here to write about things.


  11. Josh @ Biglaw Investor · December 7, 2017

    That’s awesome! 5 years of blogging is quite the accomplishment itself, plus all that other stuff. 🙂 I like to reflect from time to time like you do as well. Having a net worth chart that stretches back to when I left law school with $200K+ in student loan debt helps. Thank god those days are over.


    • Double Debt Single Woman · December 7, 2017

      Hey Josh! Thank you.

      I was just reading one of your posts (‘Do You Hate Paying Off Debt?’) a few days ago and could relate to your experiences and lessons learned. I like to joke that I have a law school sized debt, but without the lawyer sized salary. 🙂 😦 It was a really inspirational write-up.

      Congrats on your massive debt payoff. Applause! I can’t wait to be where you are in a couple of years.


  12. Four Pillar Freedom · December 10, 2017

    Five years is an incredible amount of time in blogging years, nice job with the consistency! It was encouraging to read about your debt payoff and savings over the years. I’m sure you’ll continue to hit your financial goals over the next 5 years and best of luck on your journey 🙂


    • Double Debt Single Woman · December 17, 2017

      Thank you! I’ve really enjoyed reading your blog, particularly the posts about saving the first $100k.
      Likewise, I wish you well on your FI journey.


  13. Paul · December 15, 2017

    A big congratulations from London. In the last few years student fees in the UK have been increased from £3,000 a year to £9,000 so I fear there will be many people here in the situation you faced. What is your debt amount where it’s no longer a huge mill-stone, if it falls below about $25,000 would that make it an irritation more than a burden?
    Best wishes.


    • Double Debt Single Woman · December 17, 2017

      Thanks, Paul. 🙂 Well, I’ve already paid off $30k of credit card debt, so I think once I get the balance down into the $40k range, I’ll be in more familiar territory. If all goes well I’ll be there, or in the $30k range, by the end of 2018!


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