No One Ever Wishes They Had Worked More

I've spent the last two days at the funeral of a co-worker who was a mere 42 years old. While at the funeral, I received news that another friend and her two young children had passed away. While we all understand the inevitability of death at a cognitive level, actually experiencing a loss makes death real in ways that cause a mix of emotions and real perspective. This post is my attempt at applying that perspective to my work. 

Bronnie Ware is an Australian nurse who has spent her career in a palliative care unit, caring for those with very little time to live. As someone who interacts with the dying, she has had the privilege of speaking with these people at the things that make their life worth living, as well as what they wish they’d done differently. Ms. Ware summarized the top five regrets of those about to pass on in her excellent blog, “Inspiration and Chai.” The “Top Five Regrets of the Dying” are:

1.    I wish I’d had the courage to live a life true to myself, not the life others expected of me. 
2.    I wish I hadn’t worked so hard.
3.    I wish I’d had the courage to express my feelings.
4.    I wish I had stayed in touch with my friends.
5.    I wish I had let myself be happier. 

Notice, not one mention of money and the only mention of work is to say that (especially male patients) had done less of it. If you are like me (and perhaps like most people), you are chasing the wrong dream and setting the wrong goals. As you sit and evaluate your life as it draws to a close, I promise you that you will never regret the money you didn’t make, but you may well regret lost time spent chasing a counterfeit notion of happiness. 


In a money-obsessed world that has socialized us to chase the almighty dollar, it can be weirdly unsettling to learn that money isn’t everything. As much as we whine about money, having something that is the physical embodiment of happiness is nice. We can hold it, save it, get more of it, all while mistakenly thinking that getting paid is how we “arrive.” Realizing that money does not directly equate to meaning can leave us with a sense of groundlessness but once we’ve stripped away that faulty foundation, we are able to replace it with things that lead to less evanescent feelings of happiness. Breaking your overreliance on money as a substitute for real joy is a great first step, here are two ways to move forward upon having made this important realization:

Spend money in ways that matter – Let’s be balanced in the way we talk about and think about money. It’s not the key to happiness, but it’s not nothing either. A lot of our troubles with money stem from the way we spend it. We think that buying “things” will make us happy. We engage in retail therapy which is quickly followed by feelings of regret at being overextended. Before  we know it, we’re surrounded the relics of our discontent; the things we bought to be happy become constant reminders that we’re not. 

Instead of amassing a museum of junk, spend your money on things of real value. Spend a little more on quality, healthy food and take the time to savor your new purchases. Use your money to invest in a dream – pay yourself to take a little time off and write that novel about which you’ve always dreamt. Give charitably and experience the joy of watching those less fortunate benefit from your wealth. Finally, spend money on having special experiences with your loved ones. It’s true that money doesn’t buy happiness, but it can do a great deal to facilitate it if you approach it correctly.

Find a new metric – Part of the appeal of money as a barometer for happiness is that it’s so…well…quantifiable. Meaning, joy, happiness, fulfillment are all abstractions that can be hard to get our hands around. Thus, we aim for something we can count (but end up sadly disappointed). So, take things that really will make you happy and try to come up with metrics for those things instead. Maybe you enjoy painting and you could set a goal to complete three new pieces by the end of the summer. Perhaps you want to be more service oriented and you could set a goal to engage in a charitable act each week. The impulse to measure happiness is a natural and good one, let’s just make sure we’re using a yardstick that delivers on its promises. 

For more perspective, check out "You Will Never Have Enough Money." 

For nearly 300 pages of mind meets markets, please take a look at Dr. Daniel Crosby's new book, "The Laws of Wealth."