A woman I recently met expressed that the thought of retiring felt depressing to her. In stark contrast, her husband said he was excited about it and looked forward to having time to pursue his passions. Such reactions are not uncommon. Every person nearing retirement could find their next chapter more meaningful and positive if they approached it with careful thought and a bit of planning.

Coasting into Retirement

As financial planners, we often observe people coasting into retirement without much foresight. To address this, we've introduced two hard-hitting questions into our financial planning process. These questions can be uncomfortable and sobering, but they're necessary for a liberating financial planning process that alleviates anxieties and provides clarity.

The Two Vital Questions

We don't expect immediate answers to these questions. Instead, we encourage people to take some personal time to reflect and journal their responses. When they return for their next meeting, they often seem more confident about their future. They've identified what's important to them and what could make their next phase of life exciting and meaningful.

Question 1: If you were told that you would be 100% healthy for the next five years, but at the end of year five you would die, What are the things you'd like to see happen in those five years?

Question 2: If you were told you had 30 days to live, what things would you regret?

The second question can hit hard, making you feel it right in your core. That's why we don't expect an immediate response. Your initial thoughts, however, could hold significance.

Why ask these two questions? It's because we follow a one-page financial plan that centers around what money provides and goals. Both questions prompt reflection, with the second one being notably more challenging than the first.

Top Desires and Regrets

I once knew a man who retired in the mid-90s. He had many happy years as a successful retiree, but in his final weeks, he revealed a regret: he wished he had spent more time fishing in Florida's warmer weather. This revelation was shocking as he seemed content with his retirement.

Working on these questions can make your next chapter full of purpose. Ideas might surface that you hadn't been intentional about before. This is a game-changer in retirement planning. Instead of focusing on escaping work or crunching numbers, there's a newfound passion for the next season. Writing it down makes it real and tangible.

Here are the top three things people told us they wanted to see in their next five years:

1. Spending time with friends and family

2. Exploring new places and making lasting memories

3. Embarking on a spiritual journey

And here are the top three regrets people shared:

1. Not spending enough time with loved ones

2. Putting too much focus on work

3. Holding back on sharing feelings

The Power of Reflection

These questions are powerful tools to guide your retirement planning:

1. If you had five healthy years left, what would you want to see happen?

2. If you had 30 days to live, what would you regret?

Reflecting on these questions can lead to a more fulfilling and meaningful retirement. So, take some time, reflect, and journal your thoughts. It could very well change your perspective on retirement.


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Ready to secure your financial future and optimize your retirement? Contact Nick Davis, your trusted Certified Financial Planner, for expert guidance in Dallas, Ft. Worth, Frisco, and beyond. Whether you need retirement planning, wealth management, 401k rollover assistance, or IRA guidance, Nick Davis Financial Advisor is here to help. Take the first step towards a brighter financial future – schedule a consultation here!