Giving Our Kids a Head Start Without Taking Away Their Drive

The uncomfortable business of raising independent adults when you have the means, and the inclination, to make their lives easier.

JJ and I talk about our kids almost every day. Sometimes the conversation starts with something fairly ordinary, like a bill that needs to be paid, a decision about school, a job opportunity, or one of the many responsibilities that seem to accompany being an adult but somehow still find their way back to our kitchen. Other times it becomes a much larger discussion about what we are trying to accomplish as parents, whether we are helping too much, and why something that should feel like the privilege of being able to provide for our children can occasionally leave us both frustrated.

Before I go much further, I should probably offer a disclaimer, particularly for the benefit of my wife. As usual, these are my thoughts, my observations, and my occasionally overenthusiastic attempts to make sense of something we are still figuring out. JJ and I talk about these issues almost daily, and while we share the same love for our kids and the desire to see them become happy, capable adults, we don't always agree on the best way to get there. Frankly, she does a remarkable job of helping me find some balance between wanting to provide every opportunity and recognizing when I need to back off. She is also considerably more private than I am, which makes being married to someone who feels compelled to write publicly about whatever happens to be occupying his mind an occasionally questionable arrangement. So, in advance of whatever trouble I may get myself into by sharing too much, please understand that the opinions expressed here are entirely my own and do not necessarily reflect the views, policies, or recommendations of upper management.

We have four children, all young adults now, and I am discovering that parenting them at this age is considerably more complicated than I expected. When they were little, the job seemed relatively straightforward. Keep them safe, teach them right from wrong, encourage their interests, help them become good people, and hopefully send them into the world with enough confidence and common sense to make their way. Nobody mentioned that the sending-them-into-the-world part could go on for another decade, or that the world we were sending them into might look substantially different from the one we entered.

I recently listened to a discussion about something called an inheritocracy, a term describing a society where the opportunities available to young people are increasingly determined by the financial resources of their parents rather than simply their own education, effort, or earnings. It is a provocative idea, and while I don't believe we have reached the point where hard work no longer matters, it is difficult to argue that having financially secure parents doesn't provide a considerable advantage. The ability to help with college, provide a place to live, make an introduction, finance a business idea, or help with a down payment can change the trajectory of a young person's life.

That conversation got me thinking about something much closer to home. If we have worked hard enough, and been fortunate enough, to give our kids some of those advantages, aren't we supposed to? Isn't that part of why we worked so hard in the first place? And if we do, how do we keep from creating adults who are dependent on the very advantages we hoped would make them independent?

I think this is a particularly difficult question for parents who have spent much of their adult lives trying to create some financial security for their families, especially those of us who remember how uncertain that security once seemed.

The Roller Coaster Nobody Sees

I should probably explain something about our own financial journey, because I don't want to give the impression that JJ and I have spent our lives enjoying some comfortable, uninterrupted accumulation of wealth. Whatever net worth we have today is the result of decades of hard work, persistent effort, some very fortunate breaks, and more than a few decisions that could have gone either way.

There were times when things were going exceptionally well, when we could afford to extend a vacation a few days simply because we were enjoying ourselves and had the freedom to do it. There were also times when the financial outlook was so uncertain that we seriously wondered whether we might end up living in one of our parents' basements with four children.

Those are two very different places to find yourself, particularly when your primary motivation has always been to provide for your family and keep everybody safe.

I have spent much of my adult life on what can best be described as the roller coaster of making your own way. Businesses, investments, opportunities, setbacks, decisions that worked beautifully, and others that made me question my judgment. Some years it felt like we had finally figured things out, only to discover another unexpected turn waiting around the corner. There is something exhilarating about building your own future, but it can also be exhausting when the people you love are riding along with you.

Looking back, I don't think money was ever really the objective by itself. It was what money represented: security, choices, the ability to take care of our family, and eventually perhaps a little freedom from the constant pressure of having to figure out what comes next. I have always been optimistic about our ability to work through problems, although I suspect JJ might occasionally have preferred a little less optimism and a considerably more predictable financial picture.

I am sure there are lessons our children absorbed from watching all of this, but I also suspect they remember different parts of the ride than we do. Children tend to see the life their parents provide, while parents remember the decisions, anxiety, work, and occasional good fortune that made that life possible.

And perhaps that is exactly as it should be. One of the reasons we worked so hard was to keep them from having to worry about the same things we worried about.

But there is an interesting contradiction in that accomplishment. If we succeed in shielding our children from the uncertainty we experienced, how do we help them develop the resilience and confidence that came from working through it?

The Problem With Being the Solution Guy

I have written before about my tendency to see myself as a solution guy. Give me a problem and I will research it, find somebody who has already solved something similar, assemble the available options, and generally become convinced that we can figure it out. I am an optimist by nature, and I have spent much of my life operating under the assumption that almost anything is possible if you are sufficiently creative, persistent, and willing to do the work.

Unfortunately, combining an optimist, an idea guy, and a father who wants the best for his children can produce a rather exhausting parenting style.

When one of our kids comes to us with a problem, I don't necessarily see it as a problem. I see possibilities. There are careers they could explore, businesses they could start, people they should meet, schools they might consider, and a seemingly endless collection of opportunities I would be delighted to help them pursue. I can become enthusiastic about their future considerably faster than they can, and I am pretty sure that what I consider an encouraging conversation occasionally feels to them like being cornered by an unpaid career counselor who has consumed too much coffee.

The intentions are good. I genuinely want them to discover what excites them, find something meaningful to pursue, and experience the satisfaction of building a life they enjoy. But I am starting to recognize that my enthusiasm can become a form of pressure, even when I think I am simply being helpful.

There is a difference between presenting an opportunity and making somebody feel obligated to take it. There is an even larger difference between helping somebody pursue their own ambition and trying to supply the ambition for them.

That last distinction is particularly uncomfortable because I think I have spent a fair amount of time doing precisely that.

I can see the opportunity so clearly that I sometimes forget it isn't mine.

The Economics of Growing Up Have Changed

Part of what makes this difficult is that the traditional expectations of adulthood have not kept pace with its economics. For much of our generation, there was a relatively understandable progression. Get through school, find a job, move into an apartment, buy a modest house when you could afford one, and gradually build a life. It wasn't necessarily easy, and plenty of people struggled, but the relationship between working, saving, and eventually achieving some financial stability was more recognizable.

Today, housing costs alone can make that progression difficult. For young adults, including those living in communities like ours in Central Oregon, the cost of renting or buying a home has become a substantial obstacle. A person can be working, making responsible choices, and pursuing a worthwhile career without earning nearly enough to support the lifestyle that would have been considered modest a generation ago.

This presents an interesting problem for parents. We want our children to develop independence, but are we really teaching independence by insisting they struggle against financial circumstances that we have the means to improve? If our daughter wants to pursue a profession she loves but cannot afford the rent in the city where that opportunity exists, is helping her with housing an investment in her future or an unhealthy dependency? If one of our sons wants to start a business, is providing seed capital any different from investing in somebody else's promising idea?

I think the answer depends on considerably more than the money.

There is a meaningful distinction between supporting a person who is working toward something and supporting an arrangement that allows them to avoid working toward anything. The problem is that the distinction becomes much less obvious when you are dealing with your own children, because you love them, understand their circumstances, and can usually construct a fairly reasonable explanation for why a little more help might make sense.

And of course, there is always the possibility that the next opportunity really will be the one that changes everything. Being an optimist makes that particular argument dangerously persuasive.

Are We Removing the Very Experiences That Build Confidence?

One of the things I remember about being young was the satisfaction of figuring things out. Sometimes that involved making mistakes, not having enough money, taking a job I didn't particularly enjoy, or realizing that a decision I had made was going to be considerably more expensive than anticipated. I would not describe every one of those experiences as enjoyable, but they taught me that I could deal with problems, adjust my expectations, and find a way forward.

That confidence is difficult to give somebody. You generally have to acquire it through experience.

I wonder how often, in our efforts to make our children's lives better, we inadvertently remove the very experiences that would help them become more capable. If every financial shortfall is covered, every difficult conversation is handled, every career decision is researched, and every inconvenient consequence is softened, when exactly do they develop the confidence that comes from resolving those things themselves?

On the other hand, I don't believe unnecessary hardship is particularly noble. There is no character-building benefit in making somebody struggle simply because we had to struggle, especially when the struggle has little to do with the skills or values we hope they develop.

I have heard people argue that giving children too much creates entitlement. Perhaps it does in some circumstances. But I suspect what creates entitlement isn't necessarily the amount of assistance. It may have more to do with whether the assistance becomes an expectation, disconnected from any sense of responsibility, appreciation, or personal effort.

A young adult who receives help with college and works hard to complete a degree has not somehow accomplished less because their parents paid the tuition. Somebody who receives financial help starting a business still has to build the business. We can acknowledge that family resources opened a door without pretending that everything accomplished on the other side of that door belongs to the parents.

That matters to me because I don't want our children to feel that accepting our help somehow diminishes their accomplishments.

I would like them to be able to say that they were fortunate to have opportunities, that they took those opportunities seriously, and that they built something worthwhile with them. Those ideas are entirely compatible.

Should Our Kids Know How Much Money We Have?

This question has become particularly interesting to me. Is it better for children to know their parents are financially secure, or does that knowledge quietly diminish the motivation to become financially independent?

There is a theory that you should never tell your children what you are worth, because the possibility of a substantial inheritance might discourage them from pursuing their own success. I understand the argument. If somebody believes their financial future is already secure, perhaps the urgency to establish a career, save money, or take risks disappears.

But I am not entirely convinced secrecy is the answer.

Our children are not oblivious. They see where we live, how we spend our time, the businesses we have been involved in, and the things we can afford to do. They have a general understanding of our circumstances whether we discuss specific numbers or not. Keeping our net worth confidential might prevent them from knowing the details, but it probably doesn't prevent them from forming assumptions.

Those assumptions may be more damaging than an honest conversation.

There is another problem with using today's net worth as a measure of anything permanent. Having experienced both sides of the financial roller coaster, I know how quickly circumstances can change. What appears secure today can become uncertain tomorrow, and what seems like a disastrous setback can eventually lead to an opportunity you never anticipated. I don't want our kids growing up with an expectation that whatever financial position we have reached is somehow guaranteed to continue indefinitely.

Nor do I want them to assume that everything we have accumulated is simply waiting to be distributed someday. We have our own lives to live, responsibilities to meet, risks to manage, and hopefully many years ahead of us. Money that exists today is not necessarily money that will be available to somebody else thirty years from now.

More importantly, I want them to understand that financial independence is about considerably more than the amount of money in an account. It is about making decisions, accepting responsibility for those decisions, developing useful skills, establishing relationships, and having the confidence to build a life that isn't dependent on somebody else's continued generosity.

A person could inherit millions of dollars and still lack those qualities. Another person could earn a modest living, receive occasional help from family, and be entirely independent in the ways that matter most.

Perhaps we are asking the wrong question when we wonder whether to disclose our net worth. Maybe we should be asking whether we have adequately explained what money can and cannot provide, and what responsibilities accompany the opportunities it creates.

The Problem With Expectations

Several months ago, I decided we needed to be clearer about what we expected from our children as they entered adulthood. I even went so far as to create something called the Bramscher Standard, a document outlining some fairly reasonable expectations about responsibility, initiative, contribution, and becoming an independent adult.

I thought it was a pretty good document.

As you might imagine, publishing a standard and getting everybody to enthusiastically embrace it turned out to be two entirely different things.

I have since wondered whether the problem was the document, the expectations, or the idea that I could produce a sufficiently thoughtful set of guidelines and somehow solve the complicated emotional business of parenting adult children.

Probably some combination of all three.

The truth is that our children are four different people. They have different personalities, interests, strengths, motivations, and timelines. What works for one may be entirely inappropriate for another. One child might need financial assistance to pursue an opportunity that already has a clear direction. Another might need the time and space to discover a direction. One may respond well to encouragement and suggestions, while another may experience the same conversation as pressure or criticism.

Treating them equally does not necessarily mean treating them identically.

But there has to be some consistency in the underlying principles. We can be generous without making the generosity unlimited. We can be understanding without eliminating responsibility. We can acknowledge that adulthood has become more expensive without accepting that growing up is therefore optional.

And perhaps most importantly, we have to recognize that our expectations are not the only ones that matter.

Our children have expectations of us, some reasonable and some perhaps not, just as we have expectations of them. Those expectations have developed over many years, often without anybody explicitly agreeing to them. When an adult child assumes their parents will provide something and the parents assume the child should have started providing it for themselves, the resulting frustration can feel like a failure of character when it may actually be a failure of communication.

I suspect a remarkable amount of the friction in families like ours comes from things everybody believes should be understood, but nobody has clearly discussed.

What If We Changed the Way We Help?

I have been thinking about what a different approach might look like, one that allows us to remain generous and supportive while placing more responsibility for the direction of our children's lives in their hands.

The first change might be surprisingly simple: stop offering solutions before somebody has asked for them.

This would be a considerable adjustment for me.

Instead of hearing about a problem and immediately presenting five possible solutions, I could ask what they are thinking about doing. What options have they considered? What would they like to accomplish? What help, if any, would actually be useful?

I suspect the answers might surprise me. I also suspect I would occasionally find it almost impossible not to improve their plans. But perhaps the point isn't to produce the best possible plan according to my standards. Perhaps it is to help them become better at making plans of their own.

A second change would be making financial support more intentional and less reactive. Instead of deciding each request independently, often in the middle of a busy day or at the last possible moment, we could establish a clearer understanding of what we are willing to support and what responsibilities accompany that support.

For example, helping with education might involve an agreement about the student's goals, progress, and contribution. Helping with housing might involve a conversation about how long the arrangement makes sense, what the young adult is working toward, and what responsibilities come with living in a shared household. Supporting a business idea might involve asking for a plan, understanding the risks, and establishing whether the money is a gift, a loan, or an investment.

Not because we want to make every family interaction a business transaction, but because unclear expectations have a tendency to create resentment on both sides.

There is also something to be said for allowing the kids to make mistakes that we can clearly see coming. This is where the theory becomes considerably less comfortable in practice. If I can see a poor decision developing and know exactly how to prevent it, remaining quiet feels almost irresponsible.

But if the consequences are manageable and the decision genuinely belongs to them, I may need to accept that learning to make decisions includes making some that don't work out.

I think that may be one of the hardest adjustments for parents who have spent much of their lives solving problems. We become good at recognizing patterns, anticipating risks, and avoiding mistakes, then struggle to understand why our children don't automatically benefit from all the experience we are so eager to share.

Unfortunately, listening to somebody describe an experience is not quite the same as having it yourself.

The Responsibility Goes Both Ways

One part of this discussion that I don't think receives enough attention is what all this continued involvement means for the parents.

JJ and I are in a different stage of our lives now. We have spent decades raising children, working, building businesses, making sacrifices, and organizing much of our lives around the needs of our family. There were periods when the central concern was simply keeping everything moving forward, making the next decision, meeting the next obligation, and hoping the risks we were taking would eventually produce a little more stability.

We are fortunate to be in a position where we can offer our children some opportunities, and we genuinely want to do that. In many ways, having the ability to help is one of the rewards of all those years of effort. But that doesn't mean we want to spend the rest of our lives managing everyone else's responsibilities.

We also want time together. We want the freedom to make plans without every decision being influenced by what somebody else might need. We want to enjoy the things we have worked to build, and we want to have relationships with our adult children that are not dominated by discussions about money, responsibilities, school, careers, or the next problem that needs to be solved.

Sometimes I think our frustration comes less from the amount of help we provide than from the feeling that we are still responsible for managing the process.

There is a difference between being available when your children need you and remaining the administrator of their adult lives. The former is something I hope never to lose. The latter is a job I would be quite happy to retire from.

And we parents have responsibilities in this transition too. We need to be clear about our boundaries, consistent about what we offer, and willing to let our children make decisions we might not make ourselves. We cannot keep volunteering to solve every problem and then become irritated that everybody continues bringing us problems.

I am particularly guilty of that one.

There is also a danger that our generosity can become a subtle form of control. If we provide financial assistance, do we expect our advice to carry additional weight? Does accepting our help mean our children should organize their lives around our preferences? Are they free to pursue careers, relationships, or lifestyles we might not have chosen, without worrying that our support will disappear?

Those are uncomfortable questions because I like to think our help comes without strings. But I am not entirely certain that is always how it feels from the receiving end.

We may need to distinguish between reasonable conditions attached to financial support and the much broader expectation that our children make decisions we approve of.

What Does Success Actually Look Like?

I think much of this comes down to how we define success, both for ourselves and for our children.

For a long time, I probably assumed that successful parenting would eventually produce four capable, financially independent adults with satisfying careers, stable relationships, and enough personal ambition to keep moving forward. I still think those are worthwhile things to hope for, but I am less certain that every child needs to get there by the same route, at the same age, or with the same degree of financial success.

One of our kids might become an entrepreneur. Another might find tremendous satisfaction in a profession that will never generate substantial wealth. Another might take longer to discover what they want to do, perhaps changing directions a few times along the way. I don't want them measuring their lives against mine, and I certainly don't want their sense of accomplishment diminished because we were able to help them get started.

What I do want is for each of them to feel that their life belongs to them.

I want them to know they can figure things out, that their contributions matter, that they are capable of supporting themselves and the people who depend on them, and that they can recover when things don't go as planned. Perhaps that last part is particularly important to me, because I know how much of our own journey has involved recovering from things that didn't go as planned.

I don't wish the frightening parts of that roller coaster on any of our children. I would happily spare them the sleepless nights, the financial uncertainty, and the moments when the future felt considerably less secure than we wanted it to be. But I do want them to discover that they are capable of dealing with uncertainty, taking responsibility, and finding their own way forward.

I want them to recognize the advantages they have without feeling guilty about receiving them, and to understand that gratitude and personal achievement are not mutually exclusive.

I also hope they develop some awareness that not everybody has the same opportunities. Having parents who can help with education, housing, or a business doesn't make somebody more deserving than a young adult who has to manage all those things alone. It simply gives them options that other people may not have.

Perhaps one of the best things they can eventually do with that advantage is create opportunities for somebody else.

That seems like a considerably better outcome than spending their lives either depending on the family money or pretending it had nothing to do with their success.

Learning to Get Out of the Way

I wish I could say JJ and I have figured this out. We haven't. We still have the conversations, still get frustrated, still wonder whether we are doing too much or too little, and still occasionally disagree about what the right approach should be. I expect there will be plenty more of those discussions before we find a balance that works for everybody.

But I am beginning to reconsider what my job is supposed to be at this stage of parenting.

For most of their lives, being a good father meant being actively involved. I was supposed to help them solve problems, protect them from things they weren't prepared to handle, provide opportunities, and offer direction when they needed it. Those responsibilities don't disappear when children become adults, but I suspect the way we fulfill them has to change.

Maybe the next stage requires me to become less of a solution guy and more of somebody who is genuinely interested in the solutions they come up with themselves. Somebody who can offer resources without taking ownership, provide advice without requiring agreement, and watch a decision unfold without assuming it needs my involvement.

That doesn't mean abandoning expectations or pretending every choice is equally good. It means recognizing that the ultimate goal was never to raise four people who would make exactly the decisions I would make.

It was to raise four people who could make their own.

As for whether we should tell them our net worth, I am leaning toward believing that the number itself is less important than the conversations surrounding it. They should understand our values, our expectations, the opportunities we are willing to provide, and the fact that whatever financial security we have managed to create came from years of work, persistence, risk, and some luck along the way.

I want them to appreciate the opportunities without feeling indebted for them, and to recognize the work behind those opportunities without believing they are obligated to follow the same path.

I don't want to manufacture hardship to teach them lessons, and I don't want to remove every difficulty simply because I can. I want to give them a meaningful head start without making that advantage the defining feature of their lives.

The challenge, of course, is figuring out how to do that while resisting my natural inclination to develop a comprehensive plan, explain it in considerable detail, and then become disappointed when nobody seems particularly interested in following it.

Which may be why JJ and I keep having the same conversation.

Perhaps our children are not the only ones who still have some growing up to do.