FREE NEWSLETTER

The Catch-22 of Success: How Our Achievements Shape Our Children’s Choices

Go to main Forum page »

AUTHOR: Mark Crothers on 9/16/2025

I’ve just got a hug from my daughter as she heads out our door to make her way home. I always have a sense of regret when a visit from one of our children ends. It’s always lovely to see them, but with my youngest child I admit to normally heaving a sigh of relief. Not very fatherly, but she truly vexes me.

Let me explain my difficulty. My daughter is 27 and, to my mind, going on 13 when it comes to her ability to hold firm financial opinions. Around finance, it seems whatever is the flavour of the day on TikTok becomes the firmly held conviction of the moment. Trending narrative is, to my daughter’s mind, the last word on the subject.

This situation presents a tough challenge. Do I keep trying to offer advice that she’s likely to reject? Or do I step back and let her learn her own lessons, no matter how painful they might be? It’s a difficult balance to strike, and there’s no easy answer.

At present I’m in a non-committal phase of our relationship. Whatever financial wisdom is imparted by my dear child is acknowledged with a generic response like “very good” or “I see” before moving our chat onto a more promising avenue.

The difficult part is that the anxiety doesn’t just disappear. While I’m no longer debating with her, I’m still worried about her future. This, I guess, is one of the challenges of being a parent: we can’t always save our children from themselves, but we can always be there for them. By choosing to step back from the debates, I’m ensuring I’ll still be a safe and supportive presence in her life if and when she needs me.

While my approach is working in the sense of “keeping the peace,” I truly find it an unsatisfactory impasse, and I can’t see a natural pathway for a better resolution. I guess sometimes in life, knowledge and understanding has to be experienced to be learned, even if the financial consequences could be messy. It’s hard to step back. I find this doubly frustrating because I feel her generation has a more difficult path than mine.

I console myself with the thought that my parents maybe had doubts about my financial choices, although by 27 I very much doubt that. I was two years away from starting my own business and already owned my own home. I guess being successful in all areas of life is too much to expect, but it would be lovely to eventually succeed with this thorny problem.

The only possible positive outlook is that future security for both my daughters is reasonably good due to the successful financial lives my wife Suzie and I have achieved. Although that won’t be until both our passing—hopefully, for us, a long time in the future! But at least we all have a crutch to lean on, even if it’s for different reasons between our two generations.

But the question has to be asked: does our success influence the very problem I worry about? Is it a catch-22 situation? Have I created a dilemma due to our very different experiences, causing a different relationship with money? I have no answer. Sometimes family life doesn’t present a neat solution.

Subscribe
Notify of
26 Comments
Newest
Oldest Most Voted
Inline Feedbacks
View all comments
Molly McIlhenny
3 months ago

Speaking as a 37yo who knew very little of personal finance 10 years ago, but was and still is always looking to connect with her dad in any way, I think that she’s probably just trying to relate to you, bringing up a subject that she knows you find fascinating. I would take it as a sign that she loves you and wants you to think that she’s smart. She is also probably savvier than you give her credit for and likely knows that you post here. A simple google search of your name would probably yield this article. Parents don’t think that their kids google them occasionally, but we totally do 🙂

Dan Smith
3 months ago

Thanks for this post, Molly. Thinking back half a lifetime, to when I was 37, I’m sure my folks didn’t approve of all my decisions. I recall having conversations with them as well. At the end of the day, most of the good stuff I learned, was from them.
Wish I’d had Google back then🙂

Elon Musk
3 months ago

I generally tell my adult children what I think once and then leave it alone. One of them can be quite stubborn, he tries to time the market with stuff like leveraged bitcoin ETF’s. I told him he was gambling in the market but nothing has changed.

Anyway, I think your daughter might pay more attention to being wise with her finances if you were to let her know that the safety net underneath her might not be as large as she thinks it is. You might tell her that the cost of long term care could use up all of your money before you die. This may or may not be true.

In general I believe you are right. Your success allows your own children a safety net or margin for error.

normr60189
5 months ago

I think of M. Scott Peck’s book “The Road Less Travelled” and in the first paragraph there is the statement that “Life is difficult”.  

”it’s hard to teach an adult kid new tricks.” Very true. Preparing a child for life begins early. It is a process of ever-increasing complexity. Some of it sticks and some does not. One hopes that there will be sufficient life skills acquired by adulthood, or eventually.

One thing I could not teach them was how to deal with certain types of relationships. That they had to learn on their own, and one marriage ended in an acrimonious divorce. Some things are more difficult than others. I did tell them to “choose wisely” but in affairs of the heart that side of the brain can become very clouded and reason can be overcome. However, we are resilient beings and we can overcome just about anything. Who we are in the face of adversity is a choice. That too can be taught, but is more difficult to learn.

Montessori advocated involving very young children in chores at home. As a part of the family unit, they had responsibilities even if barely able to walk. Children are eager to participate with their parents and can be very helpful, but awkward. Over time they become proficient in all manner of things.

We talk about “muscle memory” which is something acquired via repetition. It’s a neurological process that allows one to retain and execute certain motor skills without conscious effort. We also talk about acquiring good habits. These things do not occur in a vacuum.

Rather than lectures, I preferred leadership by example. When the children were very young I assisted them with cleaning up their rooms. We washed and dried the dishes together. We cooked together. I mowed the lawn and weeded with their assistance. Ditto for snow shoveling in the winter.

When I did home maintenance projects I enrolled them and gave them tools. They helped paint the trim, etc. The lists goes on.

Now, I could have hired someone for many of these “chores” but chose to use them as a means to train and develop. One of my neighbors was very opposed to what I was doing and I had to put her in her place because of interference. I lectured her with the children present. It was a teaching moment for them.

They wanted to join a youth organization to learn camping, canoeing and backpacking. Initially I tagged along but these organizations only exist on a local level because of willing volunteers. So I became a volunteer and acquired the necessary skills and was trained. The boys were part of a group of self-led explorers. It required training, planning and preparation on their part. They acquired basic life-saving skills, too. One trip was 50 miles into Canadian wilderness via canoe. 15 of us were on our own.  Along the way I, and they, collected awards. One I was given was the “District Award of Merit” as outstanding volunteer from a group of 6,000. I appreciated the acknowledgement, but I think it and the work we did together had a larger impact on the children.

In high school I took them to the office and gave them tasks on the Computer Aided Design equipment. We designed the complex decks, etc. for the home and we built them, from scratch, together. We took the drawings and pre-cut all of the lumber. My youngest son, in middle school declared it wouldn’t work. I replied “How do you think they are building the space shuttle?”  We cut and numbered each piece per the drawings. When it came time to assemble it all came together, perfectly. He admitted he was amazed. It was an excellent lesson in planning and preparation.

Finances were not as easy. They saved a portion of any earnings and I did involve them slightly in my investment decisions.  They worked their way through college. They could have gotten a free ride, but chose out of state private colleges. As part of our agreements, they were required to pay a part of this, and they did. The point I made to them was that by making a financial decision of this magnitude they would take on some of the financial burden. With decisions come responsibilities. 

There were breakdowns along the way. One memorable one was when the youngest, who was quite brilliant, got carried away with projects in college and failed a course simply because he didn’t complete the work in a timely manner. Ultimately, this required an adjustment to his curriculum and an additional semester. Frustrated, he declared he wanted to take a semester off as a sabbatical. I gave him the hard truths. 1) If he did this, it was likely he would not complete college, 2) If he came home to live, he would be required to get a job and contribute to the finances of the home, 3) There would be no “couch-potato” internet gaming sessions, 4) His share of college costs would be adjusted upwards because the purpose was to complete. He made the difficult decision to return to school.  He did complete but it took a few years for him to settle into the realities of a working life.  

Last edited 5 months ago by normr60189
Scott Dichter
5 months ago

Have you tried going on TikTok and sending her things from people that you think have a more grounded approach? I think that’s a lot easier than having arguments about it.

Mike A
5 months ago

You better hope she or her friends don’t read HD, or you’ll have much bigger problems.

Dan Smith
5 months ago
Reply to  Mike A

Mike, I often consider your point when posting.

Mike Xavier
5 months ago

Hey, we all have one. Similar boat as you and quite vexing. Trying to not get triggered by their lack purpose and overall drifting isn’t easy. Daily prayer and hope that the light bulb will come on one day is where we are currently. It could be worse, I guess.

David Lancaster
5 months ago
Reply to  Mike Xavier

Hey, we all have one.”

Or maybe not!

My two children when it comes to cars:

My daughter makes almost 200K and drives a 10 year old car that was purchased lightly used. She lives in Orange county so rust is not the problem it is here in New England. The car is starting to look a little tired but she won’t buy a new one as she doesn’t want a car payment.

My son and his wife make about 200 K as well. He has always driven used cars until they are worn out. At 37 just bought his first new vehicle.

They follow in their parents footsteps.

Joe
5 months ago

Just read an article on Marketwatch last week that 10% of millennials and Gen Z are purposefully not putting any money into their retirement accounts because they expect to receive a big inheritance later on in life. I’m sure it will work out for some but not all of them…

Dan Smith
5 months ago
Reply to  Joe

My question is, if the kids have been irresponsible with money all their lives, will they suddenly become fiscally wise when they hit the inheritance jackpot?

David Lancaster
5 months ago
Reply to  Dan Smith

How many of them will not receive the inheritance Jackpot they expect because their parents, like us, plan to eventually move to a CCRC?

quan nguyen
5 months ago

Many studies show that for young adults (18–29), the top priorities are exploring their own identities and gaining independence from parents and traditions. Fitting in with peers—both in person and online—generally takes precedence, especially in today’s Western cultures. The tug-of-war between parental influence and support may generate all sorts of conflicting feelings.

Take my niece, for example. As the only child, her parents were thrilled when she graduated from UC Berkeley at the top of her class in math, hoping she’d pursue a prestigious academic career. Instead, influenced by her newfound “Berkeley” identity, she chose to become an avid environmentalist and organic farmer. With no parental wealth to steer her but plenty of emotional support, she built an international reputation for innovative farming, even advising top chefs on sourcing herbs and vegetables.

On the flip side, a friend’s daughter in her mid-twenties, despite growing up with significant family wealth, currently lives at home, somewhat adrift—reluctant to engage with her father’s affluence but still searching for a clear path and meaningful peer connections.

In my view, it’s not parental wealth but the quality of the parent-child relationship—and the freedom to explore—that truly shapes a young adult’s journey.

quan nguyen
5 months ago
Reply to  Mark Crothers

My brother and his wife spent years encouraging their only daughter to excel in math and science, preparing her for a tech future. They gave her flight lessons, but she charted her own course on the open sea – becoming a true organic farmer in a tech-driven county. The world our children will inhabit is unseen, but love can be always their launch pad.

Last edited 5 months ago by quan nguyen
David Lancaster
5 months ago
Reply to  Mark Crothers

Wow! To Mark and Quan. Two articulate philosophical writers.

Dan Smith
5 months ago

Oh, this is a tough one, Mark. I agree with Dana; it’s hard to teach an adult kid new tricks, and you have to tread lightly.
I had one thought, and it may garner some down arrows. If she is influenced by online content, perhaps she’d take a liking to Dave Ramsey. He’s not my cuppa, and his disciples are a wee bit fanatic, still, he dishes out some common sense advice. 

David Lancaster
5 months ago
Reply to  Mark Crothers

From time to time I send my children articles that I think offer good basic knowledge with the message for what it’s worth. My daughter consults with me annually. I am essentially her financial advisor. My son and daughter in law not so much, but they are occasionally asking me questions.

Last edited 5 months ago by David Lancaster
DrLefty
5 months ago

I have found that you pretty much can’t tell adult children anything. Or aging parents. The best I can do is to casually bring up something in a “here’s what happened to me” storytelling kind of way but with no moralizing or advice. I don’t give advice to family members unless they specifically ask for it. (I’m known as the family travel planning expert, so sometimes they do ask me about that!)

David Lancaster
5 months ago
Reply to  Mark Crothers

Simple answer, “everyone has their own financial philosophy/plan that they think is best for them.”

baldscreen
5 months ago

Mark, every kid is different. At 27, your daughter is an adult. I am sure you tried to teach her well, though. Have faith in those early lessons, I am sure they will come back to her. We try to be totally hands off in regards to our kids’ finances. We are not at a time in life where we can gift them money, but I hope we will be someday. We did help them get their first houses and cars with modest gifts at the time. Chris

Free Newsletter

SHARE