When a client walks into my office for our first planning meeting, they see something different depending on the time of day. Earlier in the morning the blinds are open. One window looks out into a beautiful little yard the neighbors have spent considerable time nurturing and gardening. Later in the afternoon, the blinds are mostly closed. But the sunlight shines through another window and refracts rainbows across the walls. It is beautiful either way.
But no matter the time, I ask them the same things in that meeting. Without giving it entirely away (though many of you have been through it yourselves), there are several scenarios I invite everyone in the room to contemplate. One scenario is about freedom from money worries. It invites you to imagine and dream a little. Another scenario makes you think about how to spend our finite time on the things that really matter.
The last scenario is about regret.
Knowing you are out of time, is there anything you would regret?
A melancholy thought, to be sure. Interestingly, people respond differently to this one. Most clients answer quickly when I ask them what they would do differently if they didn’t have to worry about money anymore. Some talk about travel, quitting their job, buying things that would make their life better, volunteering, spending more time on hobbies, or helping their children and communities.
But when I ask them about regret, the response is very different. The pause is longer. People often have plans to do all kinds of things and experience all sorts of places eventually. Many financially successful people sacrifice in earlier years for “One day when we get to…”. The idea of all that time and effort for naught in a moment is not something most of us dare to think about.
Despite that pause, over 90% of people say the same thing.
“I wouldn’t regret or change anything.”
Some add a caveat, but most people land in the same place. They speak to their past actions getting them to where and who they are today, and most clients are comfortable with the life and choices they have made. If that is truly their perspective, wonderful—it is the answer we hope for.
About 10% of clients have something else to say. For them, regret is why they came to see me. For them, regret is their teacher, their compass, and I daresay their motivator. What do they say?
A handful regret not saving enough or making investment mistakes. They wish they had saved more for the ones they care about. Some wish they had learned about basic financial ideas like compound interest sooner. Some regret making poor investment choices, usually selling in the middle of a market downturn.
Some regret not living enough for today. For older clients, some ruefully remember days living overly modest lifestyles. They look back now and realize they had plenty of time to make money. They recount times raising their children when less saving might have made life easier in the moment. That sentiment is tempered by gratitude that they at least had good habits.
Many wish they had better relationships and communication with loved ones. Many of our clients are old enough to have seen their parents pass away. Some wish they had taken more time to understand the stories and values of their loved ones. Most of the time there is a will or trust in place, to their credit, but that doesn’t mean their parents communicated what they wanted their legacy to be. Mom might not have left behind that Christmas cookie recipe she knew by heart, or their uncle may not have said which of his belongings were important or carried stories beyond their basic material value. Clients often regret not taking the initiative with family conversations.
The first instinct is to feel bad for them, hearing their regrets. However, I have learned that regret is a powerful tool that can enact positive change in our lives if we recognize it for it is.
Regret is the shadow of an unrealized value. Regret is feedback that helps us understand how to live according to what matters most.
- If you regret not saving sooner, you value future freedom.
- If you regret not talking to your kids about money, you value communication and family.
- If you regret charitable intentions that were never realized, you value impact.
I ask about regret because great financial plans are built on understanding what you want. People worry about allowing regret to keep them stuck in the past, but recognizing what regret is allows us to look forward with purpose. Rather than avoid our regrets, we should honor them.
I also remind clients that though there are all kinds of ways to help them save money, reduce taxes, or improve investment returns, it can’t be at the expense of what matters most. We need to look back five, ten, even twenty years from now and be glad we implemented advice because it brought you closer to what matters most.
Does retiring at 55 help you worry less about money, or more? Does retiring allow you to have more meaningful relationships with the people you care about? Or will you regret eliminating your daily schedule and conversations with colleagues too soon?
Is selling your business all cash and leaving some money on the table worth it so you can truly step away and travel without regret? Or would you regret selling and instantly divesting because the business is too big a part of who you are right now, and you want to see it through a successful transition?
Is it worth it to set up a complicated estate plan strategy to pass on more money to your kids? Or will you regret the way you decided to transfer your wealth and legacy? Will you regret leaving the vacation home to your three children, knowing it could be a bone of contention instead of a place for family to gather?
Will you regret how you spent your money some day? Will the things you buy now keep us from having some of the choices we want later in life? Will Future Me want (or need) to retire but can’t because Today’s Me couldn’t help it?
If we always have our heads down on the day in front of us, we sometimes lose sight of why we decide what we decide. Evaluating what we regret or would regret can pull us out of today and give us broader context. Regret can help you lead a deliberate life.
Regret framed properly gives you agency.
DID YOU ENJOY THESE MUSINGS?
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