5 Things People Regret at the End of Retirement - Root Financial

In this post, we’ll be cover the five common regrets people have when looking back on their life and how to avoid them.

Watch James Conole discuss the topic, or continue reading below.


Retirement is supposed to be a time of enjoyment and fulfillment, but for many people, it can be a time of regret. According to nurse Bronnie Ware, who spent her career taking care of patients in their last three months of life, there are five common regrets that most people have when they look back on their life. By understanding these regrets, we can take steps to avoid them and create a retirement that is fulfilling and purposeful.

Regret #1: Not Living True to Themselves

The first regret that Bronnie shares is that people wish they had the courage to live a life true to themselves, not the lives others expected of them. Too often, people get caught up in doing what is expected of them, whether it is because of societal pressure or pressure from friends and family. They may work jobs they hate to earn an income so they can buy homes and cars to impress people they don’t really care about; or because they are afraid to disappoint their boss or coworkers by going in a different direction. 

To avoid this regret, it is important to be intentional about the choices we make in life. We need to think about what we want and what is best for our family, rather than simply following the expectations of others. This means having the courage to step out of our comfort zone and pursue our dreams, even if it means disappointing others. It also means being true to ourselves and not compromising our values or beliefs to please others.

Regret #2: Working Too Hard

The second most common regret that people have is that they wish they hadn’t worked so hard. It’s easy to get caught up in the rat race and sacrifice our personal life for our career. While hard work is important, it should not come at the cost of time with family and friends or pursuing our passions.

It’s important to find a balance between work and personal life. This may mean setting boundaries at work, such as not checking emails after hours or taking regular vacations. It could also mean pursuing hobbies and activities that bring us joy and fulfillment outside of work. By finding a balance between work and personal life, we can avoid the regret of working too hard and missing out on the important things in life.

Regret #3: Not Expressing Their Feelings

The third most common regret that people have is that they wish they had the courage to express their feelings. Suppressing our emotions can lead to feelings of regret and resentment later in life.

One way we can avoid this is to express our feelings openly and honestly, both to ourselves and to others. This means being vulnerable and admitting when we are struggling or when we need help. It also means expressing our gratitude and appreciation for the people in our lives who bring us joy and support us through difficult times.

Regret #4: Failing to Stay in Touch with Friends

Bronnie shares that the fourth most common regret people have is that they wish they had stayed in touch with their friends. As we get older, it is easy to lose touch with friends as we move away or get busy with work and family. But friendships are critical for our mental and emotional well-being, and staying in touch with friends can bring us joy and fulfillment in retirement.

Making a conscious effort to stay in touch with friends, even as we get older, can help maintain golden friendships that we otherwise might have let slip. This could include scheduling regular phone calls or visits, joining social clubs or organizations, or simply reaching out to old friends on social media. When we stay connected with friends, we can avoid losing touch with the people who matter most to us outside of our immediate family.

Regret #5: Wishing They Chose to be Happy

The fifth regret mentioned is that people wish they had let themselves be happier. 

Of course, everyone has different circumstances and some people have lives that are much harder than others. But Bronnie found that in general, happiness is a choice. Focussing on all of the negatives isn’t a productive choice. Instead, we should focus on being mindfully grateful and pursuing the things we love to choose being happy.

We can avoid these most common regrets by living with intention and pursuing what we truly enjoy. What does this have to do with finance? The focus should not solely be on financial planning, but rather on creating a fulfilling retirement that aligns with our values and goals. 

Money is only a tool to support the life we want to live. If we’re not living the right way first, living with intention and living with happiness, no amount of money can fix that. Having the best tax strategy, social security strategy, investments and allocation won’t do any good if it’s not supporting a bigger vision for a wonderful, meaningful, purposeful retirement. What we’re designing is the investment, tax and withdrawal strategies to support that vision of a meaningful retirement. 

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