Surviving $350,000 of My Biggest Financial Mistakes

Nobody is perfect and that includes me. We all make money blunders. The good news is despite making (some big) mistakes, you can still come out the other side! To prove this, I thought I’d share my biggest financial mistakes.

I’ve estimated that these mistakes have cost me at least $350,000. Meaning that if I didn’t make them, I’d have at least that much more money saved. Big sigh.

Here are the biggest financial mistakes I’ve made and survived to date:

#1. Cashing out my old work’s 401(k) plan & selling company stock

I started a coveted job at Morgan Stanley in 1999 right after college. It was the height of the tech boom. My starting salary was $50,000 + a small guaranteed bonus. (I made the same as a resident in 2012!) My first 6 months was in London with all expenses paid.

I was an ex-pat there – meaning I was paid my U.S. salary but received free housing (picture beautiful 2 bedroom, 2 bath furnished apartment with marble bathtub, heated towel stand across the street from Hyde Park, neighboring the Grosvenor House) and a generous cash per diem. I did not have to spend any of my actual salary to live in London.

Now I don’t totally regret this part – I was able to explore Europe on the weekends – weekend trips to Paris, Spain, Amsterdam. Priceless. Back then, friends and family from NYC could visit me in London for less than $400 roundtrip.

Plus, I had access to a 401(k) plan for the four years I worked there. I’m pretty sure I didn’t max it out, but I still had a nice chunk in that account.

Still, I cashed it out in 2004. Yup, it gets worse. In addition to a company match, we also got free stock as part of our retirement plan. I sold it.

#2. Barely saving despite high earnings as a 22 year old

I listed my starting salary in mistake #1. About 1 year later, I got a $22,000 raise and a $25,000 bonus. This meant I hit 6 figures at the tender age of 23.

My only wish is that I had some savings to show for that! I lived paycheck to paycheck despite a high income. I guess I can blame NYC.

#3. Racking up $20,000 in credit card debt before starting dermatology residency

Yeah …. someone went a little nuts during intern year in NYC. I had awesome clothes, though. I paid it all off before graduating residency. Thankfully, I no longer carry any credit card debt and pay off cards in full every month.

#4. Not funding a Roth IRA until 2014

The Roth IRA was enacted in 1997. I’ve been earning money since at least 1992, so I’m not even counting opportunities to fund a regular IRA prior to that!

I actually never heard of the Roth IRA until sometime during residency so I feign ignorance prior to that. I couldn’t imagine forking over $5,500 a year as a resident, but I totally could have.  This is especially true because I moonlighted most of residency.

#5. Not paying off student loans during residency

Every year during internship and residency I meticulously applied for deferment or forbearance on my student loans. Isn’t that what everyone does? Apparently not.

By the end of residency in 2015, I had almost $50,000 of interest capitalized onto my loans.

Surviving My Biggest Financial Mistakes

You can always earn more income, but you can’t create more time. That’s why some of these financial mistakes really sting.

Despite these awesome mistakes, I should be able to reach Financial Independence within 15-20 years and pre-Financial Independence within 10 years or less.

Feel free to share your mistakes below!]]>


  1. VagabondMD on October 29, 2017 at 4:42 pm

    My biggest mistake was buying a fancy European automobile (Volvo) before receiving my first attending paycheck. Of course I financed it, of course I regretted it a couple weeks later, and of course, I really did not NEED a new car at the time. It was also quite embarrassing when the new guy (me) had the nicest car in the practice.

    My other big mistake was to encourage my wife to pay down her student debt rather than contributing to her 401k (and GET THE FREE MONEY OF THE COMPANY MATCH!). We probably only did that for a year or less, I wised up, and we went on to do both (maxing our her 401k and paying down her debt at an accelerated pace). Within two years of our marriage, her debt was gone.

    The good thing is that both mistakes were made early, we learned from them, and moved on. In retrospect, they seem like obvious blunders, but years later, they have had negligible impact on our long term financial picture.

    • Miss Bonnie MD on October 30, 2017 at 8:19 am

      Thankfully our mistakes were early in our careers.

  2. Physician on FIRE on November 3, 2017 at 10:57 pm

    In hindsight, it’s probably a good thing I went straight through from high school to undergrad to med school. If I had started making big money in my twenties, I’m sure i would have blown through it, too.

    The biggest mistake of my grownup life came as a relatively new atteending, when I way overbuilt a house in a small town. Within a few years, I found out that town coudn’t support a hospital, and I was stuck with a great home in a place with no job and almost no one who could afford to buy a house like that.

    Eventually, a car dealer came along and took it off our hands for about a quarter million dollar loss.


    • Miss Bonnie MD on November 5, 2017 at 8:31 am

      The buying a home too early seems to be a common one for docs.

  3. Hatton1 on November 5, 2017 at 7:57 am

    I think the stupidest thing I ever did was to become “friends” with an interior decorator. I spent an ungodly amount of money going with her to “the market” in Atlanta. I still find stupid crap I bought with her and donate it to charity. My house is way over-decorated.

  4. Shivam Sahu on January 30, 2018 at 5:57 am

    Another mistake I see people making is deferring loans by continuing with higher education.

    Yes, your loans can be deferred while you’re working on a graduate or doctorate degree, but they are still incurring interest, and you’re probably taking out new loans for the higher degree, which just adds to your overall debt.

    So not worth it unless you have a very specific career plan that requires a higher degree. This post is very much helpful and a lot of students didn’t know where they are getting themselves into and then regret it afterwards.

    Hopefully more students would be able to reach this post for them to be reminded. Thank you for sharing this list!

  5. […] even tasked with taking care of aging parents. That’s a lot to figure out! I’ve made a TON of mistakes and started “late” (finished residency at age 38!) to all this. Yet, I am on my way […]

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