The Hardest Money Conversations Usually Aren’t About the Money

By
Steve Rowe
September 1, 2025
6 Mins
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By
Steve Rowe
September 1, 2025
6 Mins
Share this post

Introduction

We all know certain conversations are important—about retirement planning, long-term care, family legacy, or simply making a big decision. But that doesn’t make them easy. In this short reflection, written by Steve Rowe, we’ll explore why those topics feel hard, and how we can begin them in ways that feel safer, slower, and more human.

A reflection on why we hesitate—and how to begin again

Let’s be honest: most of us have avoided a money conversation we knew we needed to have. We don’t ignore it because it’s unimportant. We don’t delay because we don’t care.

We do it because something about the moment feels… heavy.

Or awkward. Or risky. We say, “Let’s talk about it next time.” We make a note to revisit it after the weekend. We stare at the budget line or estate planning form or college savings worksheet… and quietly move on to something easier.

That doesn’t mean we’re doing it wrong. It just means we’re human.

And if you’ve ever felt this way—about a financial decision, or a family discussion, or a conversation with a partner—you’re not alone. You’re also totally normal. Because talking about money isn’t just about maths. It’s about meaning.

We Avoid It… Then Feel Worse for Avoiding It

Research shows that people consistently overestimate how uncomfortable a “hard” conversation will be—and underestimate how much relief, clarity, or connection they’ll feel afterward. In other words, we predict pain. But what we often get is perspective. So why do we still avoid these moments? Because knowing what to talk about doesn’t mean knowing how to start.

What I’ve Learned (the Hard Way)

As a financial adviser, I’ve seen this happen dozens—maybe hundreds—of times. A client walks in ready to talk about something important: inheritance tax planning, a legacy gift, long-term care, retirement decisions.

But then the moment comes… and the words catch in their throat. Or one partner goes quiet. Or a simple question—like “What do you want to spend?”—suddenly feels like too much.

They knew this conversation was coming. But that doesn’t mean it’s easy.

And that’s not a failure. It’s actually a sign that what we’re talking about matters. Because beneath every financial decision is something personal: A story. A memory. A hope. A fear. Something we were taught, or something we’re trying to unlearn.

The Side Door: A Softer Way In

There’s a concept I often share with clients and colleagues alike. I call it “the side door.”

The side door is an approach to tough conversations that doesn’t start with the data.

  • It doesn’t push for precision too early.
  • It doesn’t jump right to the question we’re afraid to ask.
  • Instead, it eases in through curiosity and story.

It might sound like:

“When you were growing up, how did your family handle big expenses?”

“Have you ever seen someone age in a way you admire—or maybe want to avoid?”

“When you picture your kids getting into college, what kind of moment are you imagining?”

These questions aren’t nosy, and to be sure, I’m not that interested in such gossip! They’re narrative. They invite people to talk about their experience—not just their answers. And more often than not, they open up a path to deeper clarity, even if we don’t land on a final decision right away.

Because Money Is Rarely Just About Money

We like to think of money as rational. Clean. Logical. But for most of us, money is wrapped up in emotion: safety, identity, worth, trust.

That’s why something as straightforward as setting a college savings target can feel loaded. It’s not just about the number—it’s about what that number represents.

  • Is it sacrifice?
  • Is it love?
  • Is it fear of letting someone down?

The best conversations don’t ignore those emotions. They make space for them. They help translate feelings into insight—and then into action.

You Don’t Need to Have It All Worked Out

One of the most important lessons I’ve learned is that financial conversations don’t require perfection. They require presence. You don’t have to know the right answer to start the conversation. You just have to be willing to walk toward it. And sometimes, the best way forward isn’t a straight line. Sometimes we go sideways for a while.

We talk about family first. Or we share memories. Or we pause to name what’s hard before we talk about what’s next. That’s not a detour. That is the work.

What This Means for Our Work Together

If you’ve been feeling stuck, hesitant, or unsure—whether it’s about a plan, a choice, or a conversation you’re trying to have with someone else—you’re not alone.

There’s no shame in avoiding a topic. But there’s often relief in returning to it—slowly, gently, and with the support of someone who’s here to listen without judgment.

That’s part of what I’m here for. So, if there’s something on your mind—a financial decision, a worry, a hope—let’s find a way to talk about it.

  • Not with pressure. But with permission.
  • And maybe we won’t go through the front door.
  • Maybe we’ll try the side.

A Question for Reflection

What’s a money conversation you’ve been postponing—not because it’s too hard, but because you didn’t know how to begin?

This month, our newsletter is about inheritance tax planning. There is more about the nuts and bolts of this, further down and in sperate articles in the newsletter. If ever there was a money question that was loaded with emotion, this is it!  

  • They don’t deserve it – the government and / or your kids!
  • I worked hard, they need to too
  • I don’t want to talk about this, its tempting fate / I don’t want to talk about my demise

Write it down. Speak it out loud.

Then bring it with you next time we meet.

We’ll figure out how to work it out together.

Death and inheritance tax – the discussion most avoid

Death – that’s an exciting subject! And one that we all know is coming for us. I’d say, a lot of us are happy to talk about our own demise, in a dark humour kind of way. But less so, about the death of our loved ones.

And yet, we are super excited to talk about Rachel Reeves amendments to inheritance tax, with some naming her ‘Rachel Thieves’ and the sign on the M40 saying ‘Rachel Reeves: Grave Robber’.

“I can’t worry about my problems, I can’t take ‘em when I’m gone"

A Bar Song (Tipsy) – Shaboozey

Is this a problem, and since we can’t take it with us, what can we do instead? Here are some thoughts about how a conversation may go, with us or in your mind.

Leaving a large inheritance tax bill, is a financial problem, and it may rankle, but in the grand scheme of things, is it a problem that is worth you wrestling with, if you’re not going to do anything about it?

This is the first decision: Are you going to amend how you live, the things you do and most likely the amount of financial administration you have to do in order to reduce the inheritance tax bill you leave.

I’ve come up with this handy, memorable mnemonic and you’ll note that spells CRUD.  

Clarity / Realisation / Urgency / Do Something

Clarity: First, let’s run the numbers, how much are you likely to leave to your children (or whoever) as it must surely be a large sum, in order for a large inheritance tax bill to be left. For example, if each child is going to receive £400,000 gross of inheritance tax, and after inheritance tax that was, say £320,000…

£320,000 is still a lot of money! A life changing amount of money. It’s most likely more than you ever received as an inheritance. In light of this, would you be bothered?

Realisation: OK, you are bothered, even annoyed by it, or whatever other emotion it is that you cannot bury, and you keep thinking about it in your mind! Over and Over. It seems, you will carry on doing this until you put in place some plans to mitigate the bill.

Urgency: You don’t know when you are going to die. Sudden deaths happen all the time, so the time is now.

Do Something – carry on moaning or do something about it. The options are:

  • Spend it – My favoured option for you and the easiest for financial planning
  • Exemptions – use the full suite of annual exemptions, eg £3k pa gifting allowance
  • Gift it – likely to take 7 years before out of your estate for inheritance tax
  • Gift to trust for more control – don’t think the done can handle the money yet? Gift to trust and maintain control but be careful of lifetime inheritance tax charges, periodic charges and additional administration
  • Insure the bill – set up a life insurance to pay the bill when you’re gone.
  • Invest in inheritance tax exempt investments (returns may not be as good as stock market-based ones
  • Wills – make sure your Will is set up in the best way to meet your wishes and to reduce inheritance tax

A Silver Bullet to slay the Inheritance tax were-wolf

It’s a were-wolf because it comes in the night and not for everyone! That’s a good link, isn’t it? Yes, I made that up myself (I think).

There are a myriad of things we can do to reduce inheritance tax and usually, it is a combination of the above. But there is no silver bullet to kill this were-wolf! You need to look at it every year because things change:

  • Your investments will most likely increase in value.
  • Your expenditure will most likely decrease as you get older – why? Because you’re too knackered to spend it.
  • You may inherit money or not spend the larger sums you thought you would.
  • Inheritance Tax law will change

If you’ve got a problem with inheritance tax, if you can't stop thinking about it, you can find us in Solihull, UK.  

Lucent Financial Planning – here to help!

Disclaimer: This article does not constitute financial advice. We recommend that you speak to a qualified financial planner for advice tailored to your individual circumstances and goals. Financial markets may go up or down, and you are not guaranteed a return on your investment. Past performance is not necessarily a guide to future performance.

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