Want To Help Someone? Let Them Fail


That’s the sound of some people who I know falling flat on their faces.  It’s also the sound of a lesson learned the hard way.  And, in some ways, it’s the sound of a fair bit of guilt, but that too shall pass.

I’ve been sharing the stories of friends and family on this blog for years, as long as there is a financial lesson to be learned.  I’m trying very hard to keep the anonymity of my friends and family going, so pardon me if I slip into third party jargon here.

It all began long, long ago.  Some friends who I’m pretty close with have been helping their family members out financially for years.  I’m going to say that this stretches back over twenty years. The parents had been financially supporting their grown daughter’s family – constantly bailing them out of financial woes time after time.

Once, the parents, who were retired and who should have been living the good life in their golden years, went as far as mortgaging their own home to ensure that the daughter’s family would be okay. There the parents were, elderly and paying a mortgage that should not exist, because a grown adult could not control their own finances.

Year-after-year this went on, and these same bad financial habits were passed on to the children. The children grew without a sense of individual responsibility. They had, afterall, watched the grandparents fund the lifestyle of their own parents their entire lives.

As things happen, the children come into a good bit of cash, but instead of taking care of their financial obligations, they chose to spend foolishly. They quit perfectly good jobs because they no longer needed to work, because this money, more than they had ever seen, would last for a long time.

Fast forward three years later and the money is gone. The children find themselves once again in a financial bind.  What do they do?  They look to the grandparents for a handout. This time though, grandpa has long ago gone to meet his maker and grandma is even more elderly and no longer in control of her own finances. Those in control say firmly, “No, it’s time to stand on your own feet.” The children are, after all, twenty and thirty year old adults who are fully capable of taking care of themselves.

The moral of this story is that sometimes you hurt someone by helping them too much. That old parable of teaching someone to fish holds true. If the individual who you are trying to help would rather eat only after you’ve done all of the fishing, cleaning, and cooking, then there is no helping them. Sometimes, they just have to go hungry.

If you find yourself helping the same people over and over again, and if they don’t seem to be learning a lesson, you are doing a disservice to yourself and you are reinforcing their behavior. Don’t be the one giving handouts all of the time. I know that it can be hard to watch someone fail, especially when you can help them, but sometimes it’s actually the best thing to do in order to make them learn.

If you’re on the other side and find yourself constantly needing help over and over again, stop being a leech.  Evaluate how you come to be in the same situations time and time again. Remember, the people who you depend on might eventually tire of helping you and then you’re on your own.

Here comes the hate mail, but if you’re a stay at home parent, don’t depend on your spouse for 100% of your income either. I’ve seen this happen so many times where a stay-at-home mom is blindsided when the husband leaves. The last mom who I spoke with in this situation went from a six-figure income household to food stamps.  Make sure that you keep your skills sharp and be on the lookout for something that you can do on the side as well.  You never know.

Finally, if you’re helping someone financially, never lend money that you need to get back. Kiss that money bye-bye and say a prayer for the time that you spent together.

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4 thoughts on “Want To Help Someone? Let Them Fail

  • Interesting tale. I’m very sorry for the older folks involved. Sounds like they shouldn’t have left the kids that money outright, but perhaps in a trust for when they were older.

    My (ex) in-laws gave a bit of money to my kids. But, they also put the fear of Gd into those kids. That money is earmarked for one thing, and one thing only: a down payment on your first home, whenever. NOTHING else. Maybe, but just maybe, your own business, IF you have the idea of the century.

  • Thanks for sharing this valuable lesson. There’s a reason my generation (I’m 39) is called the sandwich generation; many Baby Boomers have lived the good life and never saved enough for retirement, so they are now relying on their children for help and support. This is on top of the obligation of being a parent to far too many children that have been “helicopter parented” to the point where they cannot fend for themselves. Then, the cycle is most likely to continue because feeding that many mouths often leads to very little (if anything) leftover to fund your own retirement.

    I’ve had the honor (and obligation) of helping out my parents for a number of years, but there is no way that my 3-year old son will grow up with expecting to be gifted by the Bank of Mom and Dad. We are saving for his college and a seed fund for his wedding/house down payment, but neither of these will fully take care of his obligations. He will need to choose to ratchet down expectations, or he will need to work his tail off to earn scholarships or take on student loans to pay for college.

    My wife and I believe in teaching Timmy about choices and consequences of those choices. He may hate us at times, but, in the end, it will be the best thing for him as he establishes what kind of man he will grow up to be.

  • Thank you for this helpful and all-too-important reminder.

    I find myself in a situation that as a landlord of a two-family house (and a sympathetic kind of fellow)I have allowed my tenants to forgo rent for the last 7 months. They have also borrowed my car to bring their child to school in the mornings and pick him up in the afternoons.

    Now, crucial utility bills have gone unpaid in this time period and I fear the tenants will leave without paying the back-rent. It looks like they may be splitting up and I see it as a possibility that I will be left holding the bag on the utilities and all that the lost rent would have paid for.

    • No, no, no! You can not, as a landlord be too nice. I learned that the hard way with tenants who had constant sob stories. It will tug at your heart strings but while they are living rent free, you are footing the cost of putting them up and they are saving money for a new apartment. Stop the gravy train now.

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