We’re all familiar with the motto of living with “no regrets.” It means you should always make choices that you can live with for the rest of your life. And when you don’t … well, we’ve all seen that scene in a movie when someone is on their deathbed wishing they had spent less time working and more time with their kid. 

But when I read the book, The Power of Regret by Daniel Pink, I came away with a different take on the concept of regret. Pink suggests that we embrace regret rather than avoiding it; that taking a look at our feelings of regret can be productive and a powerful force in our lives. 

Instead of dismissing our regrets or feeling shame in them, Pink argues that working to understand them can be more instructive for our future choices. This is different from the urge to wallow in regret or get down on ourselves; rather, we’re making productive use of regret when possible. Can we easily fix an action that has caused us regret? What can we learn from our feelings of regret? How can we use regret to improve our lives  and move forward with an enlightened viewpoint? 

Pink’s perspective got me thinking about all the ways in which we regret things we do with money, and how we get stuck in our financial journey because of those regrets. Pink categorizes different types of regret, which, when applied to our money, would fall into what he calls “foundational regrets,” or those related to our stability in life. Here’s a sampling of some financial regrets we’ve heard in our work with clients:

• Not paying attention to my finances earlier and educating myself.  
• Spending so much money on stupid things.
• Not saving enough when I was younger.
• Being too cautious with my money. 
• Not investing more in myself. 
• Being so focused on accumulating money or material possessions.

We’ve all experienced these regrets in some form or another. And maybe we’ve done some reflection on them, too. But the next step is to ask how we act going forward. Might we notice ourselves holding onto money when spending it could make our lives a little easier? Or that we’re dwelling on how “bad” we are with money instead of finding a financial planner to help us? How can this reflection help us correct our current actions, change our behaviors, and bring them into alignment with what we feel is right for our lives? 

We also have the opportunity to understand how our money regrets could be connected to our money beliefs or even a mindset of scarcity, which I’ve recently written about. Could extreme vigilance over our money cause us not to take the bold steps in our lives that would enrich it? Could believing that money is bad cause us to spend large amounts, thereby jeopardizing our security? Identifying specific beliefs and mindsets around money can help us examine and learn from our fear of regret. Money vigilance might make you regret not spending money on something important to you, like a much-needed vacation with your family. But if you’re aware of that money belief, you might decide to book that trip because you now recognize what’s motivating your fear in the first place.  

Harnessing your Money Regrets

So how can we harness this new awareness and knowledge for a more fulfilled life? Think of your future self from a place of abundance. What would your future self gain by making potentially “regretful” decisions about money? Some examples come to mind:

• Will my future self make sense of the fact that I took a break from work, spent some savings, and went back to school for something I love? 
• Will my future self be happy that I saved a little less each year to enjoy a more comfortable home with my family? 
• Will my future self be okay with spending all the money I’ve worked so hard to save or do I need to take action to ensure my security?
• Will my future self appreciate sacrificing short-term desires to provide more security and money later in life? 

As we examine the concept of regret and how it applies to our money, we can better understand what we’re doing with our money and why we’re doing it. You’ll rarely be able to tell if a decision might become a regret, but if you can reframe regret, you can make more confident decisions about your money moving forward. Spend some time thinking about it — you won’t regret it!

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