The 3 Biggest Retirement Mistakes—and How to Avoid Them

How you can avoid the 3 biggest retirement mistakes and set yourself up for a secure and meaningful retirement.

After helping hundreds of people transition into retirement, I’ve noticed a few common patterns—the same mistakes come up again and again. And unfortunately, they can lead to stress, financial instability, and a retirement that doesn’t quite match the dream.

So today, I want to share with you the 3 biggest mistakes people make in retirement—and more importantly, how to avoid them. Last week Benjamin Brandt joined me to discuss the key takeaways from his book “Retirement Starts Today”; this week’s episode is actually pulled from my appearance on Benjamin’s podcast. Let’s dive in!

Mistake #1: Starting Social Security and Pension As Soon As You Retire

One of the most tempting choices in retirement is to start collecting your Social Security and pension benefits the moment you stop working. After all, you’ve earned it—why wait?

However, rushing into these decisions can lead to significantly less income over your lifetime. Social Security offers delayed retirement credits—about an 8% increase per year you wait past full retirement age. That’s a guaranteed return, and in today’s low-interest environment, it’s tough to beat.

Plus, if you’re married, the decision impacts your spouse too. Delaying can enhance the survivor benefit, providing more financial security down the road.

Instead of defaulting to the earliest option, ask yourself: What’s the smartest long-term move for my situation?

Mistake #2: Misunderstanding Longevity

Here’s the thing—most people underestimate how long they’ll live. Many plan for a 20-year retirement, but the reality is, a 30- or even 35-year retirement isn’t out of the question. That’s great news for enjoying life, but it also means your money needs to last a lot longer than you might expect.

When you enter retirement with an inaccurate understanding of how long your retirement will last, you’re bound to run into unexpected challenges. That’s why I am such a big proponent of using LongevityIllustrator.org to get a personalized estimate of your longevity. 

When I work with clients, it is very common to see someone’s personalized estimate come back higher than they expected (hooray!). It’s better to have money left over than to run out in your 80s or 90s.

Mistake #3: Planning Just for “Day One” of Retirement

This one might surprise you. A lot of folks prepare only for their initial retirement needs—the “go-go years” filled with travel and fun. That’s important, no doubt. But retirement isn’t just one stage. It has multiple phases: the go-go, slow-go, and no-go years, as Benjamin puts it.

The problem? Many people only plan for the front half. They create an income plan based on what they need in year one or two, without thinking about how that income will support them in years 15, 20, or 30.

A good retirement plan has to evolve with your life. Expenses might change. Healthcare needs will almost certainly increase. Inflation will chip away at your purchasing power. Planning across your full retirement timeline—not just the first few years—is essential.

At the end of the day, retirement planning isn’t just about math. It’s about mindset. It’s about having a vision for your future and creating a strategy that supports that vision through every stage of retirement.

If you prepare yourself to learn from the mistakes of those who have gone before you, the chances of securing a retirement that fits your needs are far greater–and that means a more meaningful retirement.

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Apple Podcasts: https://podcasts.apple.com/us/podcast/retirement-revealed/id1488769337

Spotify Podcasts: https://bit.ly/RetirementRevealedSpotify 

Additional Links:

• https://www.longevityillustrator.org/ 
• Benjamin Brandt’s Podcast: https://retirementstartstodayradio.com
• Benjamin Brandt’s Website: https://retirementstartstoday.com/ 
• Benjamin’s Book: Retirement Starts Today
• Benjamin Brandt on LinkedIn: https://www.linkedin.com/in/benjamin-brandt-cfp%C2%AE-134232a8/ 
• Retirement Revealed Episode 235: Retirement Starts Today with Benjamin Brandt

Connect With Jeremy Keil:

• Keil Financial Partners
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• LinkedIn: Keil Financial Partners
• YouTube: Retirement Revealed
• Book an Intro Call with Jeremy’s Team

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