Yes Regrets?

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By: Abbey Henderson CFP® RLP® CPCC® CAP® AEP® – CEO, Wealth Advisor & Coach

Do you believe in the “No Regrets” approach to life?

A life where you take every opportunity. A life where you always take risks. A life where every decision works out. On the surface, it does seem appealing and a reasonable aspiration. But what are you giving up? Is this perspective really about avoiding being uncomfortable more than it is about outcomes? Is it actually grounded in fear?

Engaging with Discomfort

I had the opportunity to hear New York Times bestselling author Daniel Pink speak on regret at our annual industry conference in Las Vegas this fall, and it changed how I think about it.  Now, I would argue that someone with few regrets has missed an enormous opportunity to learn about themselves and to practice the very important skill of working with (and not against) discomfort. I know it sounds counterintuitive, but leaning into discomfort actually reduces it over time (for more on that topic, check out Brené Brown’s work).

According to Pink, most regrets fall into one of four categories: boldness, moral, connection and foundation. Here are some examples I have seen with clients:

According to Pink, most regrets fall into one of four categories: boldness, moral, connection and foundation. Here are some examples I have seen with clients:

  • Foundation – regrets about stability/security: If only I had saved more money when I was younger.
  • Connection – regrets about relationships: If only had I resolved issues with my parents before they passed away.
  • Boldness – regrets about meaning: If only I had quit that job I hated because it paid me well and taken a chance on what I really loved to do.
  • Moral – regrets related to being the person you want to be: If only I had been more generous with my time and money.

The “Learn from Regrets” Approach

Using our regrets for good requires intention and practice. It is far too easy to get wrapped up in letting our brains replay (on repeat) what we could have or should have done. From a neuroscience perspective, when our brain wants to ruminate, the best strategy is to give it a task to do. I loved one of Pink’s ideas: a failure resume. And you can do this as an exercise now or as a regret appears.

To write a failure resume on past regrets, choose five regrets or failures (any five will do). For each failure, write down what you’ve learned and then write down at least one “action item” for the future. Here’s an example:

Regret: “If only I had saved more money in my twenties and thirties, instead of spending my money on things that didn’t matter, I would have more flexibility and options as I head into retirement.”

Lesson Learned: “This regret has taught me that early decisions can compound over time and have significant impacts. I also learned that spending choices should be made with thought and intention – not on impulse.”

Action Items:

  • “I am going to be more thoughtful about my spending decisions now – are my choices meaningful and aligned with my values?
  • I am going to share my financial regrets with my children and grandchildren so they can see a different perspective and perhaps begin to approach their decisions with more thought and intention.”

As a side note, I recommend handwriting your resume. There is a lot of research around the merits of handwriting vs. typing.

You can work with regrets from any of the four categories in this manner, and if you want to work on any financial regrets, we would love to help you. In addition to being wealth advisors, we are also coaches and are uniquely positioned to help you incorporate learning from your regrets into a comprehensive plan. Get in touch if you would like to explore this further.

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