You Have Them, I Have Them – How To Contend With Financial Regrets

“You don’t hear anyone on their deathbed saying I wish I would have spent more time at the office” became the flagship phrase for pursuing a life well lived.  Yet, regret remains the emotional catalyst for guilt, shame, fear and angst.  Many regrets have financial roots or implications.

There are two ways to address regret and the financial entanglement, as we are human and they are unavoidable –  Minimize them and/or learn from them.

First, minimize the regrets we have in life.

George Kinder in his seminal work as one of the founders of financial life planning developed three contemplative areas of questioning that may lead to fewer life regrets.  These questions changed the life trajectory for myself, family, friends and clients.  To get the most out of this exercise, don’t read the next question until you finish the one before.

First:  “Imagine you are financially secure, that you have enough money to take care of your needs, now and in the future. How would you live your life? Would you change anything? Let yourself go. Don’t hold back on your dreams. Describe a life that is complete and richly yours.”

Second:  “Now imagine that you visit your doctor, who tells you that you have only 5-10 years to live. You won’t ever feel sick, but you will have no notice of the moment of your death. What will you do in the time you have remaining? Will you change your life and how will you do it?” (Note that this question does not assume unlimited funds.)

Third: “Finally, imagine that your doctor shocks you with the news that you only have 24 hours to live. Notice what feelings arise as you confront your very real mortality. Ask yourself: What did you miss? Who did you not get to be? What did you not get to do?”

There may be some sadness, a pause – regret that bubbles up with the last questions.  You get very clear on what is important at a heart level.  The power of using this framework when looking at your financial life is that it enables you to align your life values with your choices.  You create an emotionally charged vision that has meaning and purpose.  It will help you to make financial decisions that profoundly impact your life, may be uncomfortable, even scary as you live your version of true wealth.

The next area of grappling with regret is to learn and grow from them.

Dan Pink and his latest book ‘The Power of Regret: How looking Backward Moves Us Forward’ challenges us to reframe our experiences and partner with regret to find lessons and facilitate growth.

Pink and his research teams found four core categories of regret that spanned the domains of romance, education, and finance.  Let’s look at them through a financial lens.

Boldness regrets come from missed opportunities.  Even when taking a change didn’t play out as hoped for, research found that people who took action extinguished the nagging “what if” feeling.  Client examples of this type of regret include “I wish I’d bought that house or investment,” or I should have quit that job and pursued the career track I loved.”

Foundation regrets are like compounding interest and gather steam over time.  “I wish I would have saved more when I was younger”; or “I wish I would have stuck with a spending plan and avoided debt.”

Moral regrets happen when you shift outside of your financial integrity, boundaries or value system.  “I regret paying my son’s rent after realizing he was an addict,” or “I stay in my unhealthy marriage because I am afraid of the financial implications”.

Connection regrets.  By far the largest category in Mr. Pink’s research was around relationships.  I have seen fallings out over finances “I regret not talking to my brother after he didn’t pay me back.”  “My mother and I disagree over how I spend my money – so we don’t talk anymore”.

Mr. Pink suggests that our regrets are a “photographic negative of the good life we want, a value, a purpose or other components of a life well-lived”.  Use these regrets as an opportunity to move forward, to grow.  We need to be kind, forgive ourselves and others and make course corrections in what is the next best step to become bold, build a foundation, live in our integrity and renew connections.

Don’t fall short of your potential as you simply put a number on some financial goals ascribed by the traditional wealth management or financial services line of thought. The keys to minimizing, learning from or growing around financial regret is to acknowledge they exist, and sit with the feelings it brings up.  Find the professionals that will support you in the process of aligning your financial decisions with your vision of a life well lived.