Biggest Financial Regrets – Have Any?

Someone recently started a thread on Reddit asking “What is your biggest financial mistake/regret?” I posted a couple articles on our biggest mistakes in the past and so I perused the Reddit thread to see if our misery had some company.

Here were the responses – in order of how often people mentioned them:

Spent too much on college/an impractical major (6)

  • I was surprised that this was the top financial regret, as investing in your education is generally a good thing, but many Redditors are younger and still dealing with the cost of college.

Mistimed the real estate market/bought too much (5)

  • Pretty much anyone who bought a house in the early-2000s probably had this experience. It’s amazing how many of these commenters were in California!

Expensive divorce (3)

  • One respondent has been given this advice: “Instead of an expensive wedding, just find a woman who hates you and buy her a house”

Stayed too long in bad paying job (3)

  • There is a lot of inertia to being in a job and looking for a new one requires a lot of work (and can be emotionally taxing). Still, people often get ahead by finding out what they are worth to other employers (or starting their own companies).

Starting saving too late (3)

  • This one is one that millions of Americans realize each year. Retirement savings are less than half of what experts say is needed to reach a comfortable retirement.

Large/luxury car loans (3)

  • Cars are about the most expensive depreciating asset that people make. The article I wrote on this suggested fancy cars can cost people 4 extra years of work. That doesn’t include the interest you might pay to buy fancy cars.

Bad individual stock pick (2)

  • Someone wrote they “sold Apple stock figuring that Steve Jobs was out of tricks after the iMac”. We’ve got beat on company stock a few times, but generally shy away from individual stock picking.

Afraid to invest in stock market after the 2008 crash (2)

  • That would be quite a bull run to miss out on since the S&P500 has risen about 400% since it bottomed out in early 2009.

Not buying Bitcoin at 75 cents (2)

  • This one is a little like regretting you didn’t win the lottery. Still, many people were interested in Bitcoin early on but didn’t buy in. (BC is @ $6,300 today)

Some of the other comments …

  • High fee mutual funds
  • Buying luxuries on credit
  • Making 401k withdrawals while working
  • Having a smoking habit
  • Having a gambling habit
  • Making loans to family members

Which of these financial regrets have you run yourself into?  Which ones might be missing from the list these people experienced?

Image Credit: Pixabay

10 thoughts on “Biggest Financial Regrets – Have Any?

  1. Invested in Limited Partnership which invested in currencies, commodities, and alternatives through a prospectus I didn’t understand. Lesson learned: Never invest in something you don’t understand.

    Liked by 1 person

    1. I had an investment like that presented to me last week at our Angel Club. I couldn’t figure out what the value proposition of the service was and the presenter couldn’t articulate it!


    1. Yes – that would have been about the top of the market, especially in certain cities where the bubble was more inflated than others.


      1. I wrote a “financial failures” article about the house we built in 2009. I still don’t think we are close to what we paid for it yet.


  2. I joined one of the largest tech companies back when it was a startup and worked my tail off there for 15 years. I made a lot of money but not even a small fraction of the $300 million I would have made if I kept all the shares until today.

    The stock has gone through multiple 80+% declines in its history, and I was a young man who used some of the proceeds to buy a house to live in and to replace a 15 yr old 2nd hand car. But there is some regret in selling all those shares. Some particularly interesting notes: many current employees made more from the stock than I did due to explosive growth in recent years; the 1.5% of shares I still own comprise a big chunk of my portfolio; shares I gifted to younger relatives are worth $200k each now, more than enough to pay college expenses; shares I sold to buy my house would be worth $80 million now. 😀


    1. Those numbers always amaze me, Joe! I guess you have to make decisions on the information you have at hand and can’t look back. Especially when you’ve done so well overall. Sometimes when we spend money on something expensive – like Super Bowl tickets – I’ll tell my wife “I’m going to tell you how much we spent ONCE, then we’re going to enjoy ourselves and NEVER mention it again!” 🙂


  3. Mine would be: Started investing too late. I’m surprised no one mentioned it (or maybe it’s included in the ‘started *saving* too late?’)
    Anyway, my point is around financial literacy, and the fact many of our schools are simply not teaching it. I had to learn everything myself as an adult, and although I have been lucky enough to do quite well at growing (and protecting) our capital, I could have started 10 years earlier!!


    1. Yes – I think that saving/investing are the same on people’s responses, although investing is more accurate. Yes also on financial literacy. I was lucky to have taken a ‘Business Law’ class in high school, but most people don’t get a good grounding in personal finance. I was a merit badge advisor for Personal Management when my son was in Boy Scouts and I know that kids that age (high school) don’t know much about it, even though many are driving & have part time jobs.


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