What happens when you take real-life financial decisions women face in midlife… and turn them into a game?

In this bonus episode of The Iconic Midlife, I’m joined again by wealth advisor and financial life designer Hayley Dickson for a rapid-fire round of “Worth It… or Not?”

We put some of the most common midlife money dilemmas on the table — the kinds of choices many women quietly wrestle with:

Should you prioritize experiences now or build more long-term wealth?

Is it worth staying in a high-paying job you’ve outgrown?

How much risk actually makes sense in midlife?

And when does a financial decision stop being strategic… and start being emotional?

There aren’t always obvious answers — which is exactly why these conversations matter.

Hayley shares how she helps clients think through these trade-offs so their financial decisions support the life they actually want to live.

Because at the end of the day, money isn’t just about accumulating wealth.

It’s about designing a life.

About Hayley Dickson

Hayley Dickson, CFP®, CEO & Founder of RIPPL Wealth Management

Hayley Dickson, CFP®, is the CEO & Founder of RIPPL Wealth Management. A former SVP of Global Acquisitions at Fremantle Media who walked away from a six-figure entertainment career to revolutionize wealth management, Dickson became the fastest-growing advisor in Northwestern Mutual's history before launching Rippl Wealth Management in 2025.

As a financial life designer, Dickson provides truly comprehensive planning, democratizing sophisticated strategies for everyone from first-generation wealth builders to self-made entrepreneurs to seasoned professionals seeking discerning counsel that’s often reserved for ultra-high-net-worth individuals. Unconventional and bold in her approach, she builds her practice on radical transparency and trust.

Exclusive Offer for Listeners

Hayley is offering our listeners a complimentary 30-minute one-on-one Life Design & Wealth Strategy Session (a $500 value). This private offer is capped at 30 individuals – simply mention this episode when you reach out to reserve your spot.

To claim your session, send an email to rippl@nm.com mentioning the podcast in the subject line or fill out the contact form directly on their website:

https://rippl.nm.com/contact.htm

Connect with Hayley:

LinkedIn: https://www.linkedin.com/in/hayley-dickson

Instagram: @hayleywdickson

Join the Inner Circle: https://the-iconic-midlife-with-roxy-manning.kit.com/3433416614

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Let’s Connect

Social media: @theiconicmidlife (show) | @redcarpetroxy (host)

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As long as you have enough cash reserves for three, six or 12 months of living expenses, it is so not worth it to keep anything beyond that because you are losing purchasing power and not keeping up with inflation, then you're going to run out of money at 77 and that's going to really suck.

That would not be fun.

If you can put away 20% of what you earn and you're in a place that you can earn more and save more and live more, that works. But if it puts you in a position where you have your paycheck to paycheck, that doesn't make any sense.

Taking a major financial risk risk in midlife.

As long as you have a phased

out plan, prioritizing travel and experiences in your 40s and 50s instead of maximizing long term net worth.

That's the myth. You do both and you can do it beautifully. This is the secret that nobody believes.

All right, Haley, welcome back to the iconic midlife. Are you ready for a game? Yes. We're gonna have so much fun.

We are gonna be playing a quick rapid fire game and this game is called Worth it or not Worth it. Okay, so basically these are real life financial decisions midlife women have to make sometimes. So you just let me know what you think.

The first thing that comes to mind when I read these scenarios.

Okay. Worth it or not worth it?

Yes.

Perfect.

All right, number one, keeping a second home, that isn't a great investment but deeply improves your quality of life. Worth it or not worth it?

Depends. But worth it.

Like if it's joyful, it's not like

an insane burden and just a really, really drain.

And those dollars go towards like what you would spend at a hotel or what you would spend, you know, the opportunity cost, like, then yes, it's worth it.

It's worth it. Staying in a high paying job you've outgrown for five more years to dramatically increase long term wealth, not worth it. Ah, okay.

So joy overrides like the financial benefit in that case, like your peace of mind and your happiness.

These are so hard for me because I typically do so much design and iteration and forecasting.

But my, my thoughts is that this person has probably already amassed quite a bit of wealth and therefore does the additional five years in expanding that net worth. Is that suffering or everyone to call it like worth the, like the, the marginal increase in joy that person would get afterwards? Probably not.

And they just don't know that. And so putting that on paper and like helping to, you know, I love to model things to like to to, to, to assist in decision making.

But if this person is, you know, just gotten this job and it's three times their pay and they're kind of behind, you know, then yes, for sure.

Helping launch your adult child financially if you can afford it, even if it slightly delays your own wealth acceleration. Worth it or not worth it?

Worth it. If the child presents a business plan to you about what they plan to do with the money, the timeline, all of that.

Not worth it if you just want to help your child because that's turns into enable, like enabling them.

Right. And probably a never ending ask on their.

Right.

Yeah, yeah.

This is the agreement. Here's the business plan. This is the agreement. And then, you know, there we go.

I remember I had a friend in high school whose dad was an attorney and anytime she brought something to the table that she wanted, he literally made her sign a contract and was like. And it was like.

But she learned, you know, like, okay, like I need to prioritize first of all and things are serious, you know, and she had to follow through, which I thought was really interesting.

Pitch me like, I'm an investor, you know, it doesn't, you know, an investor in what this money's going to go towards both in terms of, you know, you know, just supporting you in.

And with rent in a place you can't afford because you have access to, you know, internships or, or you know, positions at a certain job, it's going to turn into something else.

Or even if it's just, you know, like, hey, I need a gap year and here's my business plan as to how this is going to, you know, support me emotionally and then on this date I'm going to do this, this and this. Like, you know, it's like, I just think there has to be a plan with exactly, like you said, like a contract and an end date.

Choosing a more expensive city or lifestyle because it excites and energizes you. Even if you'd save far more living somewhere else worth it. Who stayed in LA after like the pandemic.

Right? But as long as you. I talk about that 20% planning budget.

If you can put away 20% of what you earn and you're in a place that you can earn more and save more and live more, then that works, you know, but if it puts you in a position where you have your paycheck to paycheck, I mean, you know, that doesn't make any sense. Especially in your mid.

Yeah, exactly.

When you don't want to be struggling necessarily, you Know keeping money in lower risk, lower growth places because peace of mind helps you sleep at night.

Not worth it. As long as you have enough cash reserves for three, six or 12 months of living expenses.

It is so not worth it to keep anything beyond that because you are losing purchasing power and not keeping up with inflation. And you feel so safe and you have the best sleep. But then you're going to run out of money at 77 and that's going to really suck.

That would not be fun. No, no.

It's just so real.

What do you do in a case like that?

Like if you get no in a case like that?

I'm very kind and gentle because there's real legitimate fear there and just because it doesn't logical sense, it's real and it's been, they've been holding onto this for a long time.

And so if somebody has, like I said, let's say if someone has, you know, they spend 10,000amonth and they have 36 months of expenses in cash, 360,000. I'm not going to say, hey, hey, Roxy, like you, we're just going to take, you know, 330,000 and throw it into the stock market. And now you have 30.

Good luck. That's going to be a psychologically damaging and absolutely traumatic for that person.

So we, we drip it, we say, okay, let's get you from 360 to 180, okay. And we really talk about why that's safe. And then they see it and they see what happens.

And then the next meeting in three or six months, we reduce it a little bit more. And so we drip it in so that they experience it and feel it and believe it themselves. It's not just words coming out of my mouth.

Yeah, that's a good point. You kind of like drip it in, do it slower, kind of get them used to it. Okay.

Such a destructor of wealth that makes people sleep better at night. It's. Don't do it.

Prioritizing travel and experiences in your 40s and 50s, instead of maximizing long term net worth, we do both.

That's the myth. People think that they live in the or world.

I'm either going to travel and do everything I want and because I'm not going to wait to do all this stuff and experience the world, you know, in time old, you do both and you can do it beautifully. This is the secret that nobody believes until I show it to them. You can be so savvy and building your net worth and saving and making smart choices.

And paying less in taxes and spend way more than you could ever imagine on travel. At the same time, I'm telling you, people think it's either or.

It is not taking a major financial risk in midlife, starting over professionally or investing heavily because the upside could change everything.

Worth it all the way, as long as you have a phased out plan. So when my clients are looking, let's say they want to start their own business or they want to, you know, let's use that.

They've been in the corporate world for 25 years or, you know, whatever, and they want to start a consulting business. We set out phases, say, okay, the worst thing you can ever do is immediately start to freak out about where am I going to earn money?

You might need six to 12 months of just thinking time right after you leave that job, just planning, building the business, strategic materials, client base, whatever.

And so we want to say, all right, we're going to, we have a bucket of capital that is going to be used for the transition and we do not need to earn any money for an entire year. That piece allows them to actually succeed in this transition. You're safe, you're good. Now month 13, I'm just making this up.

I need you to earn, you know, start. Think about earning at least 60, whatever it is in the next three months and then this and then this and then, and then we kind of benchmark it.

And if within two years you're still, you haven't earned anything, well, then that's the red flag. So I'll have conversations the other day, I did. They're like, am I at red flag yet? I'm like, no, you're a yellow flag. You got about four months left.

So get going. Your yellow flag, you know, and I tell people, like, they know when they're red flag and it's time and.

But I mean, I very rarely, honestly, like, I don't know if I've had a red flag, to be honest. It's typically yellow flag. Yellow flag, yellow flag.

Yeah.

And then, and then, you know, people typically don't go back.

Yeah, it's like the, the warning is enough for them at that point.

Yeah.

The last one. Intentionally planning to spend most of your money in your lifetime rather than preserving a large inheritance. Worth it or not worth it?

That is so individual, you know, like what matters to you? Again, you can do both. Especially if you get life insurance early on, that's structured to never expire.

That's like the best because it pays out whenever you pass away and it pays out Tax free, and it's quite a large chunk, so if you start planning, you know, through that lens. But, you know, I really think that if you do, like, my.

My belief on estate planning, I think a lot of people don't think they need to do estate planning until they're, you know, in their 60s or they have enough to plan with. But my philosophy is, if you have stuff and you love people, you need an estate plan.

Like, what happens to your stuff, like, when you're no longer here and just talking about kind of basic trusts and stuff like that. But I think that, you know, you can live such. You should live your best life, like, while you're alive.

Yeah, right. Enjoy what you have. Right?

Enjoy. And I think this is a whole nother topic, but inheritance and gifting, you know, our gender, our parents, the boomers. Right? No one talks about.

No one talks about anything. What's love? What am I gonna. Like, you know, I really coach my clients on having conversations with boomers about inheritance because it's so taboo.

And so, you know, I think our generation, we need to be like, for me, like, I want to spend my money on my kids, like, while I can see it while I'm alive and experience it with them. I'm not saying I just want to give them a bunch of money, but help with a down payment or let's do a safari together.

Like, you know, like, that kind of stuff I think is going to be a lot versus, like, I'm just going to die, and then you're going to get all this money, you know, or whatever it is. So, yeah, I would say a combination.

First, I think it's most important to live life in the way you want to live it, you know, while you're on this planet.

And secondly, I think children, you know, I mean, will benefit from accelerated gifting and accelerated life experience because they want to spend time with you and do awesome things with you while you're alive. And thirdly, you know, if you have the ability to get, you know, permanent insurance, that's a great way to inject capital to the estate.

That's great grandbaby money, too, you know, versus saving money to gift.

Good point. Oh, my God. So much amazing information. I feel like I have to go back now and look at my financial plans and kind of get.

Make sure everything is correctly in order, because that does. I mean, you've given so much amazing knowledge and information.

So for those of you guys who have not listened to Haley's full episode, go back to Tuesday's episode, because she's amazing. I mean, you could, you know so much about this, about this whole topic and, you know, for those who want to come find you, where can they find you?

You know, we can, you can fill out a form on, on the website. We're at ripple R, I P P L dot NM like New Mexico dot com. I'll also put my, you know, email that goes to the general inbox.

And I had had shared with Roxy that the first 30 listeners like mention the podcast and the subject. We will do a complimentary, like 30 minute, one on one consult with which we typically charge thousands of dollars for.

So excited to just lift up your listeners and see how we can give them some clarity and confidence if they already have a plan. If they don't have a plan or if it makes sense for us to work together, we can explore that as well.

So that is exciting. Everybody should check her out for sure because like I said, even taking that call with you, I mean, they probably will glean so much information.

So it's really valuable, right?

It's really valuable.

Fun and sexy. Doesn't have to be heavy. Yes. Yeah. I'm not a numbers person and I should have, could have, would. No, no, no. Yeah, let's go.

I mean, come on. It's never too late, right? It's never too late. Never.

Never.

Amazing. Well, thank you so much, Haley. It's been such a pleasure to talk to you. Thank you for everything.

I really appreciate it.