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17 People Share Their Biggest Financial Failures of 2016

   Posted On: December 30, 2016  |    Posted In: Debt  |     Posted by: Broke Millennial®

The only face you’re required to show online is the carefully curated one you’d like others to see. You use the filters to remove the bags under your eyes. You crop to keep soft parts of your body out of sight. You post updates about how in love you are with your spouse on an anniversary, even though it’s been the most trying year of your marriage. You wax poetic about all the books you read, especially how you were trying to cover a more diverse authorship, but you watched far more hours of reality television than you had your nose in a book. The danger in this careful curation of our lives is the aliennation we feel in sharing everything from our small missteps to massive failures. How can you share online, or heaven forbid speak to someone in person, about your mistakes when everyone is fronting as #flawless?

Today, we’re not posting the successes of the last 12 months. Instead, I and 17 other money nerds are sharing our biggest failures of 2016.

My year included everything from spending screw ups to down right defying Uncle Sam.

  • Mistake 1: Not keeping spending in check when my income changed. It’s a classic tale. Girl starts blog. Girl starts freelance writing. Girl decides to quit full-time job and become a full-time freelancer. Sure, there’s a bit more to why I took the risk to work for myself this year (*cough* book *cough*). I saved a healthy nest egg for the transition, but I didn’t fully prepare for the change in my monthly income. Not merely about the size of checks, but the frequency of when they actually came in. Alas, my spending habits stayed pretty similar to life with a stable income. I ended up my raiding one of my savings accounts more often than felt comfortable.
  • Mistake 2: I didn’t pay quarterly estimated taxes. Last year, despite being employed full-time all year and paying extra taxes from my paycheck to offset freelance income, I stilled owed to the tune of $8,000. This year, I was traditionally employed for 8 months and then became self-employed. I again defied the rules and didn’t file quarterly-estimated taxes. I’m probably going to get punched in the teeth with a penalty this year on top of what I owe in taxes. Goodie.
  • Mistake 3: I got real lazy about returns. This year saw in uptick in online shopping. Probably because I detest going out and buying clothes. I tried to solve this hatred by ordering online. Of course I sometimes got items I didn’t love, but several times I just got lazy about having to actually get on the train, brave the brick-and-mortar location in Manhattan and return the item. I probably wasted at least $100.
Here’s what everyone else had to say.


  • “Ours was the same consistent failure nearly every month this year. We consistently blew our monthly budget for groceries. And it wasn’t eating out/food because that’s a separate category for us. We just couldn’t stay under our allotted amount for household items and groceries. Every single month in 2016 we had to take money from another category to get through the month. Needless to say, we’ll be upping our grocery allotment in 2017 and decreasing somewhere else.” – Nick True, Mapped Out Money
  • “Twice this year, I caught myself with the case of the ‘fuckits’ after going slightly over budget. As in, I already broke my budget, might as well buy $300 worth of new clothes that I kinda need, but don’t need right now.” – Emilie Lima Burke, Burke Does
  • “$429 in traffic violations in under 24 hours. We could have done much better things with that money!” (Read the full story here.) -Hélène Massicotte, Free To Pursue
  • “In November, I was optimistic about doing a ‘No Spend November’. Instead…. that was my highest spending month of 2016! Ultimate fail. However, just because I failed at not spending any money doesn’t mean I regret it as part of the overspending was an unexpected opportunity to donate to charity.” – Gwen, Fiery Millennials
  • “I had more than one month of dropping ~$1,000 on food and drinks this year. I justified my ballooned expenses because earning more meant I ‘deserved’ delivery, eating out, or extra drinks.” – Kate Dore, Cashville Skyline
  • “I spent $500 on an online weight loss course that sucks…no refunds.” – Lisa Phillips, Affordable Real Estate Investments
  • “I haven’t done the numbers yet, but I’m pretty sure I spent more than I made. However, I enjoyed the travel I spent the money on, and I’d probably do it again, though I can’t afford to do it every year.” Teresa Mears, LivingOnTheCheap


  • “We failed to save up in advance for a new front door and storm door that we knew we needed. The cost ended up on a credit card and even at no interest, it still took the whole year to pay off.” – Gary Weiner, Super Saving Tips
  •  “Made more money and didn’t save enough for taxes. Depleted my emergency fund to pay my tax bill. This was tough as I just rebuilt my emergency fund after paying off my debt. Lesson: save more for your EF and your taxes!” – Melanie Lockert, Dear Debt


  • “I don’t know if this is too vague, but hopefully it’s still useful…. I lost around 6k and nearly depleted my emergency fund this year because of the roller coaster ride that is my personal life. That said, I don’t know if I’d have done anything differently. I allow myself to take risks and fail in my business all the time. It costs money and I learn. Why shouldn’t we give ourselves the same permission in our personal lives? That said, I hope it doesn’t happen again. And the lesson learned, I need a bigger emergency fund.” – Stefanie O’Connell,
  • “The only real money mishap was I wish I would have spent the money I put into my business more wisely. There was a LOT of wasteful spending. I already have a budget planned for more mindful spending next year.” – Jessica, Every Single Dollar
  • “I spent $40,000 on my business this year, which is more than I took home. While I’m all for investing in yourself and your business, it should be done strategically while keeping ROI in mind.” – Lauren Bowling, Financial Best Life


  • “We’re getting ready to give our home back to the bank through a deed in lieu of foreclosure.” – Lindsay, Notorious D.E.B.T.  Here’s an excerpt from Lindsay’s post expanding on her story: A home of your own is the American Dream—or at least that’s what I’ve been led to believe my whole life. Unfortunately, I wasn’t given the skills to know how to actually achieve this goal growing up. Instead, my husband and I have gotten ourselves into a pickle that we can’t get out of now—unless we give up our home.  (Read the full story here.)
  • “We did a major house remodel in 2016 – basically we built a new house. I had budgeted 10% for cost overruns, and it ended up closer to 30%. Some of that was us choosing more expensive options, some of that was my builder’s fault, but the contract was pretty poor. Note for next time: a couple of hundred dollars at the lawyer up front may save you thousands in the long run.” – Kate Horrell, The Military Finance Coach
  • “We didn’t double check a price on fixing a problem in our new house before we accepted a price reduction. It’s apparently going to be far more expensive than the sellers indicated.” – Kathleen Celmins, For Profit Blogging

Will you be honest and share your biggest financial failures from 2016?

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12 responses to “17 People Share Their Biggest Financial Failures of 2016

  1. I’ll own up to some terrible investment market timing.

    I put 20% of my portfolio into bonds in September in preparation of my “year off from work” for less volatility. Bonds have gone down about 4% since then. There was no way to know that in advance of course.

    If I made that move in January instead, it would have triggered less taxes. I did know that in advance, but I made the move anyway. Oh well!

  2. I made a lot of mistakes this year too. I ended up spending 132% more money in 2016 compared to 2015 due to lifestyle inflation and many spending/savings equation getting out of whack. It’s a great idea to get these out into the open.

    I feel you about those quarterly taxes. I got burned last year and owed $11,000 extra dollars. This year I hired a tax expert and an accountant! Paying for professional advice is sometimes really worth it.

  3. One of my biggest mistakes in 2016 was I didn’t commit to making more money with a side hustle or looking for higher pay outside my job. I made some good progress on saving/ cutting expenses but need to see more improvement on the income side in 2017.

  4. I know we have done lots of mistakes especially on finances, but it’s completely fine as long as it has taught us something to better our financial status. Next year, let’s do something to improve our finances to reach our own financial goals and to achieve financial independence.

  5. Great list! I totally understand yours Erin for not sending in quarterly taxes… I also didn’t do that this year and may be regretting it. Hopefully, I can get my act together in 2017. Thanks for including me!

  6. After reading this post I am shaken. I intend to start work on my new business this year and charter out all the financial plans, to begin with. Learning from the mistakes of others I will have to take care to minimize the possibility of any major blunders. Thank you for sharing this piece as it has made me a more alert person than ever.

  7. It is important that we learn from our mistakes and the mistakes of others as well. Sharing tips and experiences help us to grow. Thanks for sharing!

  8. wow..I am glad to see some of my friends screw up too. 2016 was the worst financial year for me. I made poor decision and screw up everything. I used all my savings to take unnecessary financial risks and I ended up jobless. Now from November till now I have been working. It cost me my holiday..urgh

  9. The most successful people will tell you that at some point in their careers, they thought they were going to fail. Not because they didn’t have enough confidence in themselves, but because they had risked everything.

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