Spend the Money: Tackling the Emotional Side of Retirement Planning

I’ve spent a lot of time helping people figure out if they can retire. But what surprises many is that the harder part often comes after that: convincing them it’s okay to actually enjoy their money.

On a recent episode of The Wealthy Barber Podcast, I talked with Dave Chilton about this very problem – how even the most financially secure retirees can freeze up when it’s time to spend. They’ve won the game, but can’t seem to leave the field.

That’s where the real value of financial planning comes in – not in the spreadsheet, but in the emotional coaching that helps people align their money with their values.

Why Good Savers Struggle to Spend

It’s no mystery why so many retirees are reluctant to open up the spending taps.

They’ve spent 30 or 40 years accumulating. They’ve maxed out their RRSPs and TFSAs, avoided lifestyle creep, paid off the mortgage, maybe even helped their kids with education or down payments. They’ve done everything right.

But when the paycheques stop, their entire financial identity gets flipped upside down. The same instincts that made them successful savers – discipline, restraint, long-term thinking – can work against them in retirement.

Now they’re looking at their portfolio and thinking, “If I take money out, I’m going backwards.” It doesn’t feel like income. It feels like loss.

The Fear Beneath the Numbers

I work with many clients who are in excellent financial shape. Their plans say they can spend $90,000 or $100,000 per year with ease. But their actual spending is closer to $60,000.

Why?

– They’re afraid of outliving their money – even when the numbers say they won’t.

– They feel guilty for spending on themselves after decades of deferred gratification.

– They want to help their kids but worry about giving too much, too soon.

– They’re anxious about the market, interest rates, health care costs, or the next unknown curveball.

These fears aren’t irrational. They’re human. But they do need to be addressed if you want to get the full value out of the money you’ve worked so hard to save.

Conflict-Free, But Not Emotion-Free

When I say I offer “advice-only” financial planning, people often think that just means fee transparency. No products. No commissions. No conflicts or hidden agendas.

All true.

But what surprises clients is how much of our work has nothing to do with investment returns or tax optimization. Instead, we spend a lot of time talking about values, identity, and purpose.

Yes, I’ll show you how delaying CPP can boost your inflation-adjusted income for life. But I’ll also ask what you’re waiting for – and whether holding out is really about maximizing value or avoiding uncertainty.

Yes, we’ll talk about withdrawal strategies. But we’ll also talk about why it’s so hard to stop saving and start living.

Sometimes people just need permission – from someone objective and unbiased – to take the trip, upgrade the vehicle, or pay for the big family reunion. And that’s what I’m here for.

Behavioural Coaching in Action

This isn’t therapy. But it’s not just math either.

Let’s say your plan shows you can comfortably spend $100,000 per year. That includes covering your fixed expenses, some travel, a new car every ten years, and gifts to your kids. You’ve got a well-diversified portfolio and guaranteed income from CPP, OAS, and maybe a defined benefit pension.

And yet, you’re still hesitating to book that river cruise or splurge on business class.

That’s when I pull up the projections. Not to show you a number – but to tell you a story. What does your life look like if you do take the trip? What if you don’t?

We explore scenarios, set spending targets with confidence, and create space for what I call values-based indulgence – not reckless spending, but intentional joy.

Why This Matters More Than Ever

Investment advice is cheap. Literally. You can build a low-cost, globally diversified portfolio with one click. You can automate rebalancing. You can find hundreds of blog posts (some of them mine) showing how to optimize your TFSA, RRSP, or non-registered accounts.

What’s scarce is the human side of financial advice – the kind that recognizes you’re not just a spreadsheet.

Good advice-only planning offers two things that an index fund or a robo-advisor can’t: context and coaching.

– Context means we look at your whole life: family, health, goals, risk tolerance, spending patterns, and personal quirks.

– Coaching means I help you stay on track – not just with the plan, but with your mindset.

Especially in retirement, this kind of support is more valuable than ever.

You’ve Won the Game. Now What?

If you’re reading this and thinking, “Yep, that’s me. I know I could be spending more – but I’m stuck,” you’re not alone. Many of my clients have plenty of financial capacity and still worry about running out of money.

My job isn’t just to build a plan. It’s to help you follow through. To nudge you, gently, toward a life that feels fulfilling – not just financially secure.

Retirement isn’t about having the biggest pot at the end. It’s about getting the most value out of the resources you’ve got – while you’re still healthy, mobile, and able to enjoy it.

So if you’re waiting for permission, here it is:

You don’t need more spreadsheets. You need to spend the money.