Four Retirement Regrets I See Time and Time Again

By Adam Stewart, Compound Wealth

Over the years, I’ve helped hundreds of Kiwis plan for retirement, and I’ve also seen the same regrets surface, often too late. While every person’s situation is different, there are a few themes that come up again and again.

1. Waiting too long to retire

This is sadly one of the most common regrets I come across. People work hard, make responsible choices, save diligently, and then retire late only to find that time, health, or energy has slipped away.

I’ve seen this in my own life. My dad passed away in his early 60s. He was a hard worker, and that was his choice, but there were things he never got around to doing. He could have slowed down a few years earlier and made space for some of the experiences he’d talked about. That stays with me.

Retirement isn’t a finish line you have to cross after decades of sacrifice. It’s a window of time and one worth protecting.

2. Not spending more earlier in life

Reading Die With Zero earlier this year reinforced what I already believed. Most people are too cautious with their money during their healthiest, most capable years.

It’s easy to say “maybe later” to holidays, experiences, or even simple pleasures. But later doesn’t always come. I’ve seen people pass away with money left over but a bucket list still full.

Being financially responsible doesn’t mean always playing it safe. It also means knowing when it’s time to enjoy what you’ve built.

3. Not tracking progress early enough

This one often shows up as uncertainty. Questions like “Have I done enough?” or “Can I actually stop working?”

Without tracking your progress over time, it’s hard to know what’s possible. You can end up over-saving and missing out, or under-saving and feeling stressed. Neither is ideal.

That’s why we help clients define what a meaningful life looks like, then put a plan in place to make it real. It’s not just about having a good retirement. It’s about living well on the way there too.

4. Relying only on KiwiSaver

KiwiSaver is a great tool, but too many people treat it as their only investment strategy. The downside is that you can’t access it until age 65 unless you’re buying your first home, and that can limit your flexibility.

Investing outside of KiwiSaver gives you options. You can draw income earlier, make decisions without being tied to withdrawal rules, and adapt your plan as life changes.

Having a mix of investment options helps you stay in control, not just of your retirement but the years leading up to it as well.

Retirement is about more than money

The biggest regret I see isn’t missing a market return or picking the wrong fund. It’s missing life.

If you’re in a position to make choices earlier - retire part-time, take a big trip, spend more while you’re healthy - take them. A financially secure retirement matters. But a fulfilling one matters even more.

If you’re unsure whether you’re on track for that kind of life, we’d love to help.

Adam Stewart
Compound Wealth