5 Biggest Financial Mistakes that 50-Year-Olds Regret The Most

Updated: May 14, 2024

I had the chance to talk to future retirees during a recent speaking engagement. Among the topics that we discussed were the biggest financial mistakes that they regret now that they’re in their 50s.

Today, I’m sharing with you a few of their stories, which I hope you’ll find valuable.

Read beyond their sentiments and learn from them. There’s still time for you to avoid their mistakes.

1. I regret buying all this stuff that is now useless.

“Whenever we get a significant amount of money, my husband and I would spend it on something unnecessary.

We often bought cars, renovated and redecorated our homes with new furniture, and splurged on gadgets and appliances.

Our children now have their own families and are leading their own lives, so we’re left with an empty house filled with all the material stuff we’ve bought over the years.

Looking back, we should have made smarter spending decisions. If we had bought rental apartments or started a business, we wouldn’t be worried now about our retirement.”

2. I regret waiting for my income to increase before investing.

“When I was still single, I was able to save regularly. But I put all of it in a savings account because I thought that one needs a lot of money before one can start investing.

When I earned more from my job, that was the only time that I began investing in mutual funds. But it was already difficult to invest because I also got married and had children during that time, and cash flow was tight.

I calculated it and discovered that if I invested all those savings that I had during my 20s, then it would have been around P20 million today. I could have quit my job and retired yesterday.”

3. I regret not planning for retirement.

“Next year, I will be forced to retire. And despite having a good amount of savings and an adequate retirement package, I’m still so worried about my finances.

What if that amount is not enough? Where will my wife and I get money if our savings run out? I’ve been working in the corporate world my whole life, and I don’t know how to do anything else other than my work.

If only I had planned for my retirement, then I wouldn’t be so lost today. I could have explored business opportunities that would ensure continuous cash flow during my retirement years.”

4. I regret trying all those get-rich-quick scams.

“I’ve always been attracted towards get-rich-quick schemes. And as the story usually goes, all of them just ended up being scams.

I’ve lost a lot of money from those “guaranteed profit” investments. In fact, I’ve lost money repeatedly from different scams because I was too greedy to admit to myself that they don’t really work.

Sometimes, I imagine what would have happened if I had invested all that money in legitimate investments like the stock market or mutual funds. It makes me sad when I realize how much I could have earned today instead.

5. I should not have relied on SSS alone.

“I’m retiring soon, so I asked our HR Department about SSS and its pension benefits. I was shocked to find out how little I would receive, just around P10,000 per month. The monthly cost of my maintenance medicines is almost half of that already!

Now, I’m trying to delay my retirement and asking the company to give me a few more years. I’m also cramming to start a business or find a freelance consultancy job if the company doesn’t ever grant my request.

All these years, I thought SSS was enough — but it’s not. The monthly pension you’ll receive will never be enough for your cost of living when you retire. I learned this the hard way.”

What to do next: Click here to start your financial journey with IMG Wealth Academy


  1. So true, i regret also for not having any savings all i thought my SSS pension is enough am now in my late 50’s. It’s been years that i had been reading your blogs it inspires me a lot.

  2. Thanks for sharing this. I will show this to my wife since we always talk about my father (now on his 80’s) depends on his sss pension alone. It’s fortunate for us that we have invested our money on rental properties (we are both in our early 40’s).

  3. a lot of my friends invest their money, some on business, some on stocks, some on mutual funds, some said I should have continued my SSS, some says I should have saved money in the bank. they all have regrets. you will never know if you will get lucky or you’ll lose your money. How many entered business and succeed. how many invested and got lucky? You may do everything to save and invest and still get nothing. Do not deprive yourself today just to prepare for your future. the future will take care of itself. buy what you need, don’t overspend, any excess then invest it. if it succeed or not atleast you have lived well. good luck. 🙂

  4. Thanks for sharing, just to share my life now I’m 31 blessed to engage in investing in small amount from my little salary. Very thankful for the financial literacy I’ve read, i remember Bo Sanchez book of how he teach his maid how to invest in stock market. I hope before turning 35 I put up my own Electrical Engineering service firm.

  5. I just turned 60 y.o. and proud to share my younger years was never wasted. My 4 yrs stint in the M.E. provided me the seed money that saw me buying cheap but potential properties instead of developing my residential house or buying a car. Until now my house is the same undevelop house . The properties i bought at hundred pesos were sold at millions each, …Now my problem, i cannot get my 18 months SSS Lump sum pension because im a Businessman. The 250000 investment i made in 1997 now turned into a 24 room hotel in the city i lived. My message …..put your money in real estate. thank you

  6. Yes regrets come, what would you advise 50+ yr old then? I know its late but what meager retirement fund options can they still do? I think this is an impt question and a lot is waiting for the answer. Kindly gve a few mins to advise . Thank you

  7. @P

    It’s important to plan for what’s ahead. Focus on your cashflow and find ways to increase your income and decrease your spending. Be realistic with your expectations. And remember that your greatest enemy at this point is procrastination.

    Lastly, personal finance is personal. So if you want specific advise, it’s better to consult with a financial planner.

  8. Most of the list, I can check off as done fairly well. Not perfection mind you but done to the best of my ability and things have worked for me as I look back well over six decades. My regret pile is centered around mostly bullet point #1, STUFF that is now useless. “Investments” I made but I was not ready for and allowed something that could have worked out to become an almost total loss. It is true, most of us get wiser as we get older.

  9. I loved to work work work and focussed only on paying for my children school until I lost my job at 55 with only a property. I was at least able to live without rental pressures but my children school fees continued to be a pressure. Out of the small gratuity I build another property which has cushioned my pressure at least for school fees. My pension barely covers my expenses. Luckily I have medical insurance. I had accumulated a lot of assets (equipment, cars, etc) around which I disposed off, and invested in a tiny house. I’m planning to sell my car and build another tiny house.

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