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Avoiding Regrets In Your Financial Life

future regrets get in the way of your ideal future

❝Life is too short to be in a hurry.❞ -Henry David Thoreau

I feel nervous as I pick up the phone. I have to call customers today as part of my job. I work as a bank teller during college and the word came down today that tellers have to start calling customers to try and to get them to open more accounts. I guess they think they have untapped salespeople. Our main objective is to get as many accounts open as possible. We even have limits we are supposed to meet if we don't want to get in trouble. They are incentivizing tellers with big bonuses if we open the most accounts.

This is all well and good if I believed a new account would be good for customers. If they could benefit from opening a savings account and moving a portion of a large checking account balance into it, I would be on board with that. If I could help a customer with a large balance in a low-interest savings account open some higher-interest certificates of deposit, that would be my pleasure.

I really struggle with forcing customers into subpar products, though. I know some of these customers would be better off with their money invested, possible through a brokerage account, but we don't offer that and we're definitely not allowed to send money away.

Every time I'm on the phone with a customer I feel uneasy. I know it would be good for me financially - and I certainly need the money as a broke college kid. I know it would be good for my career if I want to stay in banking. Unfortunately, it's not always right for the customers and I can't do it.

I'm lucky to be able to say that I left banking. If not, I most certainly would have regretted my career choice.

it's uncomfortable when we live inauthentically


Bronnie Ware, who worked as a palliative caregiver working with those who were at the end of their lives, noticed some themes as she talked to her patients. Many people felt regret over various areas of their lives, and she started to pick up on various themes. There were five regrets that kept showing up over and over. She wrote about these in her book The Top Five Regrets of the Dying.

The top source of regret people experience was that people wished they lived a life that was true to themselves instead of living a life that was expected of them. In other words, they didn't live in alignment with their values.

bronnie ware top 5 regrets of the dying inauthentic

The second top regret of people looking back on their lives was that they worked too hard. By working too hard, they didn't leave room in their lives for the things that were truly important to them. Many of these people worked hard so that they could, at one day in the future, eventually use their time in ways that were important to them. Unfortunately, they ran out of time and ended up regretting it.

bronnie ware top 5 regrets of the dying worked too hard

The third most common regret is that people wished they had the courage to express their feelings. By extension, people wish they were better able to understand their emotions and feelings. People, for reasons that seemed right in the short run, never told their loved ones how they really felt. They didn't express themselves and kept their feelings to themselves, leaving things unsaid.

bronnie ware top 5 regrets of the dying didn't express myself

The fourth regret is that people drifted apart from their friends. People, reflecting on their lives, wished they had stayed in touch with their friends. It's easy to lose touch with friends, especially when life happens. However, this seemingly small decision compounds over time and becomes a major source of regret.

bronnie ware top 5 regrets of the dying lost touch with friends

The fifth top regret people experience is not allowing themselves to be happier. Many people put off their happiness until at some point in the future. They may tell themselves they will be happy as soon as they retire, once the kids are out of the house, when they get that promotion, or after they find someone to have a relationship with. Others never let themselves be happy because they didn't realize happiness is a choice or that they don't deserve to be happy.

bronnie ware top 5 regrets of the dying didn't allow myself to be happy

You might be wondering the point of learning about the regrets people have on their death beds. It's uncomfortable for many to contemplate the uncomfortable truths of their lives, particularly when thinking about the shortness of life.

However, we can understand the main sources of regret so that we can not only recognize if we are heading down a path of regret, but more importantly, we can realize them now when there's still time to do something about it.


Who are you?

Really? Who are you underneath all the social identities you have?

Your true self is the person you would be if there was nobody to impress. It represents the kind of person you would be if you had perfect confidence to be yourself.

Understanding your true self is an important first step toward living an authentic life so that you lessen your chance of experiencing the first regret.

true self underlies our social selves


Understanding who you are and living authentically doesn't mean you don't have public personas. We can't act like a jerk, for example, and justify it by saying we are just being ourselves.

You might be a slightly different person at work than you are with your kids, or with your partner. You might act differently with your family than with your in-laws.

The problem with authenticity isn't that we have social personas to take on. It's only a problem if we don't know who we are without our masks on. Not knowing who we are at our core is summarized nicely by the group Blue Man Group in their Persona:

In the evening I take it off

But there's another one underneath

And I can't seem to find the bottom of the stack

I might just lose my mind and never get it back

social self and persona masks


If I ask 100 people whether or not they are going to live forever, 100 people would be able to tell me "no." But alas, that's the logical side of them talking. Most people live their lives as if they are going to have more time in the future.

Now, it is true that most of us most of the time can reasonably assume we will be here next year. We do have more time...until we don't...and we experience the regrets that Bronnie Ware writes about.

As morbid as it may sound, having a healthy relationship with the fact that life is short helps us appreciate the time that we do have. It gives us a sense of gratitude and awe that nudge us to not waste the time that we do have so we can look back on our lives from our deathbed and say that we would do it again.

life is short gratitude


Contrary to popular belief, money is not a goal. Nobody on their deathbed has ever said they wish they could have spent more time with their money, or wish they sacrificed more relationships so they could have more money.

In the end, money is a tool. It's a tool that you can use to support the kind of life you would be happy to look back on.

But that's the trick. You can't very well use your money to support the kind of life you would be happy to look back on if you don't know who you are or what you want out of life. This is the first step toward living on purpose, with purpose.

Knowing who you are and what's important to you helps you understand what your money is for. It helps you define your financial purpose. Having confidence in your financial purpose helps you align your life (including your financial life) with the things that are the most important to you.

intentional living and financial purpose

Life is short and if we forget to keep that fact in mind, we may end up looking back on our lives with regret. You don't have to seek money as a goal. Instead, you can use it as a tool to live the kind of life you would be happy to look back on.

You get one life; live intentionally.

With gratitude,


If you know someone else who would benefit from reading this, please share it with them. Spread the word, if you think there's a word to spread.

Related Money Health® Reading
References and Influences

Ben-Shahar, Tal: Choose the Life You Want

Burkeman, Oliver: Four Thousand Weeks

Burkeman, Oliver: The Antidote

Dunn, Elizabeth & Michael Norton: Happy Money

Emmons, Robert: THANKS!

Glasgow, Joshua: The Solace

Irvine, William: Guide to the Good Life

Irvine, William: The Stoic Challenge

Lindsay, James: Life in Light of Death

McKay, Matthew, John Forsyth, and Georg Eifert: Your Life on Purpose

Millburn, Joshua Fields & Ryan Nicodemus: Essential

Sinek, Simon: Start With Why

Sivers, Derek: Hell Yeah or No

Solomon, Sheldon, Jeff Greenberg & Tom Pyszczynski: The Worm at the Core

Wallace, David Foster: This is Water

Whelan, Christine: The Big Picture

Yalom, Irvin: Staring at the Sun

Note: Above is a list of references that I intentionally looked at while writing this post. It is not meant to be a definitive list of everything that influenced by thinking and writing. It's very likely that I left something out. If you notice something that you think I left out, please let me know; I will be happy to update the list.



About the Author

Derek Hagen, CFA, CFP, FBS, CFT-I, CIPM is a speaker, writer, and coach specializing in financial psychology, meaning and valued living, resilience, and mindfulness.


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