You can learn from your mistakes. Hindsight is 20/20. History forgotten is history repeated. These may be clichés, but there is more than an ounce of truth to them. That’s why I decided to reach out to my friends and ask the question, “What is your biggest financial regret?”

My friends being as awesome as they are, the answers I got were not only interesting but thoughtful. And as our first commenter notes, there is a common theme:

The two things that I see with almost every client is experiencing is that they did not start saving early enough towards retirement, or for financing for the education of their children. The result is, in many cases, having to cut back on lifestyle to finance these two goals. The alternative in the education financing often is burdening their children with exorbitant student loans.

Next up is someone who works in the financial industry with some of their own inside information:

The biggest financial regret I made is that I put my children’s private high school and university education at a higher priority than my own retirement.  

Today, as a professional comprehensive financial planner,  I sometimes counsel my clients differently.  

Of course, it’s unique to each client, but some clients should save into your tax deferred accounts first because those funds aren’t counted in the university’s scholarship and grant pool. And today, there are so many more opportunities for the children to qualify for grant and scholarship money — and are often needs-based.

If the child needs to take out subsidized Stafford loans in junior or senior years (interest starts six months after graduation) the parents’ funds continue to grow in the interim and when the parents turn 59-1/2 they can withdraw funds to cover the children’s shortfall — if there is one.

Depending on where the child begins his career, there are also many more sign-on bonuses where a company will cover the child’s student loans once he/she is hired.

Retirement surfaces again in this next testimonial, but it also brings up the issue of “staying home with the kids”:

1) Not scraping together the money when I was 26 years old to buy a townhome in Hoboken. I could see that it was just ready to emerge and since then real estate has done very well there.

2) Although I have saved more than most people my age for retirement, as I approach 50 (I just turned 48), retirement and the amount of money needed for that seems “right around the corner” and I am worried about my ability to save enough to live as comfortably as I want.  I wish that I had saved more, earlier. Especially because this would have not been a huge impact on my overall lifestyle yet would have meant the difference between buying 5 new shirts that month or 1. Even that small amount would have added up to a lot so that now it would not feel so daunting! I know I”ll make it there but wish I was further along.

3)  I took 1.5 years off when [my son] was born and another 2.5 years. Although I know I did the right thing for him by being around more, it was a big financial impact and I lost 4 years of income in my highest earning years. So although I don’t know if I ultimately would have done anything differently, I do sometimes lament that I could have been a lot further along now in securing financial security.

Some comments were as humorous as they were insightful:

  • That I did not get Long-Term Care insurance when I was young enough to make it affordable.
  • I didn’t start a retirement savings plan early in my career.
  • That my husband is also a self-employed person!!!!!!!!!!!!!!!!!!!!!!

And lastly, the single, solitary bit of wisdom that didn’t mention retirement:

  • Purchasing a timeshare with my partner that we never use and cannot sell!
  • Breaking the lease for our office space and being taken to court with the result being tens of thousands of dollars of rental to be paid out of pocket!

My friends have spoken. Now it’s your turn: What was the worst financial mistake that you have ever made?