Each generation is shaped by its upbringing and the defining events of its time.

In this episode of Couchside Conversations, Wealth Advisors Sophie Leahy, Austin Overholt, and Beau Wirick explore how these influences shape financial decisions across generations: Baby Boomers, Gen X, Millennials, and Gen Z (we still need more time to let Gen Alpha cook). Through personal anecdotes and real-life examples, they reveal how family money conversations change over time and why passing down core values, rather than just wealth, creates lasting impact.

Tune in if you’re interested in…

* How different generations approach money, saving, and retirement

* Why financial values are shaped more by experience than age

* How to have better money conversations within your family

* Teaching kids about money through values* Balancing spending, saving, and giving across generations

* What each generation can learn from one another

Watch previous epsiodes here:

A Family Meeting: Creating Shared Understanding Around Wealth | Morton Wealth

Where to Live In Retirement | Morton Wealth

Today I am joined by two wonderful wealth advisors, Sophie Lahey and Austin Overholt, to talk about how different generations view wealth. Last year we had this conversation, and it’s one of my favorite conversations. We kind of made a caricature of baby boomers and millennials. This year, we’re doing the opposite.

Instead of putting generations in a box, we’re going to talk about how every person is an individual within a generational context. We’ll try to see things through more of an individual lens. However, you can’t talk about generations without generalizing just a little bit. So with that, I’d love it if Sophie and Austin could take us through a bit of a collage of each of the generations we’re talking about.

Sure. And before we do that, I think we need to hear from someone else who has a little insight on these generations. Boomers are all about money. Gen X is like, is it all about money? Millennials are like, where is the money? And Gen Z is like, what is money? That’s my bad stand-up routine.

Okay, Sophie, I believe you are technically, surprisingly, a baby boomer — just technically — so you have the honor of walking us through that generation.

Hi everyone. My bet is that many of us in the room today are baby boomers. Baby boomers are typically those in their later working years or in retirement. Take a look at the screen and see if you recognize the toys you may have played with growing up, the music you listened to, or the movies you enjoyed.

Any baby boomers here looking at this and thinking, that’s me? Amy Poehler told us that baby boomers think it’s all about the money. That may be because they benefited from the economic boom following World War Two. They’ve often been good savers, able to own homes, build retirement savings, and in many cases retire after long careers, now enjoying more leisure in life.

So Austin, tell us about Gen X.

I’m not technically Gen X, but I kind of identify as one. I’m right on the border between millennials and Gen X. This generation tends to be independent, resilient, and maybe a little skeptical — or a lot skeptical.

That really comes from their upbringing. They were the latchkey kids, taking care of themselves after school while waiting for their parents to come home. As they entered the workforce, they experienced major economic downturns early on. They built back, only to face another downturn later. That resilience shaped how they approach money.

Now, as they look toward retirement, it may not be a hard stop like it was for baby boomers. Instead, it may be more flexible or phased.

It’s amazing to think about that generation, because they were hit early in their careers, then again not long after. Tough timing.

All right, next up we have millennials. Millennials are my favorite generation — as a self-proclaimed millennial. They grew up with computers and phones and are very tech-savvy.

When they entered adulthood, they faced a difficult job market. Many took on student debt expecting high-paying jobs that didn’t materialize. To bridge the gap, we saw the rise of side hustles, gig work, and social influencing.

For many millennials, retirement feels far away. Instead of a fixed retirement goal, the focus is more on financial freedom — the ability to choose whether or not to work.

And then we have Gen Z. These are younger individuals who grew up fully immersed in digital life. Social media, the internet, and the pandemic have shaped how they socialize and work.

They tend to value flexibility, purpose, and nontraditional career paths. Their relationship with money is different — often more digital and less tangible.

There’s even a story of someone offering cash to a younger person, and they didn’t recognize it, asking instead to be paid digitally.

So with that, that’s the generalization of the generations. I want to move into something more individualized. One thing about Sophie and Austin is that both of you are very values-driven. I’d love to hear how your individual values were shaped — how they were passed down to you and how you’re passing them forward.

Sophie, let’s start with you. How did your upbringing shape your financial journey?

I was raised in France by parents who grew up around World War Two. The values they passed on were centered around family, education, and saving. There was a strong emphasis on investing in education to build a future.

Compared to today, there were fewer outside influences. It was more family-centered, and it was easier to save and avoid overspending because there were fewer temptations.

What about you, Austin?

My parents are baby boomers, but financially they were more focused on experiences than accumulating wealth. Growing up, I sometimes wished we had a bigger house or more material things. But instead, my parents invested in experiences and relationships.

They made our home welcoming, hosted friends, and created lasting connections. Looking back, that taught me contentment and that we don’t need to spend excessively or keep up with others.

Did either of you ever resent your parents’ approach to money or rebel against it?

I didn’t, but my brother did. Same upbringing, different reactions.

I didn’t rebel, but I definitely questioned things at times. As a teenager, I wanted more, but I understand now why we didn’t have those things.

You both have kids now. What do conversations about money look like in your own families?

My kids are still young, so we focus more on values than technical financial details. Kids are always watching — how you spend your time, energy, and money. They may not articulate it, but they understand.

We talk about choices. For example, we might not buy something today, but that doesn’t mean we can’t afford it. It’s about priorities.

We also teach them to divide money into spending, saving, and giving. They’re learning that money isn’t just for consumption but also for planning and helping others.

We also have intentional conversations about what money is and what it means in our family.

That’s amazing.

For me, with older children, the conversations evolved over time. As they grew up, we talked about careers, education, and trade-offs. We discussed decisions like paying for college and the implications of different choices.

Now, as adults, I see them making their own decisions. They don’t necessarily follow everything we modeled, but they’ve developed their own perspectives.

Did your kids adopt your values or take a different path?

They didn’t rebel, but they do spend more than I did. That reflects the environment they grew up in — more exposure, more experiences, and different expectations.

Final question for both of you: what’s something you admire about another generation?

I admire the long-term mindset of older generations — their discipline in saving and planning for the future.

And I admire how younger generations are willing to take risks, seek balance, and define success differently.

I hope the takeaway here is that every family is a multi-generational unit, and the goal is to have better conversations, build stronger connections, and understand each other more deeply.

We have time for a quick question.

A question about younger generations came up.

That generation is still very new, and it takes time before we can really define patterns. It was the same with millennials — it took years to understand them fully.

Another question: what would you have done differently?

I wish I had invested earlier and taken advantage of opportunities sooner.

I wish I had invested outside of retirement accounts earlier for more flexibility.

I think we’re at time. Thank you so much for joining us. If you have any questions, feel free to come talk to Sophie or Austin.

Disclosures: Information presented herein is for discussion and illustrative purposes only and is not intended to constitute financial advice. The views and opinions expressed by the speakers are as of the date of the recording and are subject to change. It should not be assumed that Morton will make recommendations in the future that are consistent with the views expressed herein.