Why We Procrastinate, and How To Fix It

I hope all successfully emerged from yesterday’s April Fool’s Day unscathed. Last week’s post pointed out the dangers of procrastinating, which can be particularly costly in estate planning. This week, let’s dive deeper into the risks of procrastinating and the rewards of getting your planning done. Failing to plan can be a very harsh way to make your family feel they’ve been fooled. As my friend Tom Rogerson of GenLegCo. cautions: “Failing to plan is planning to fail.”

To illustrate, consider this real-life tale of two families described by family business consultant Jeff Savlov in his Family Business Minute blog on February 21, 2024. Savlov tells the horror story of an entrepreneur who procrastinated, followed by the success story of a matriarch (Savlov’s own mother) who did it right.

First, the bad story. At age 60, a car accident killed a serial entrepreneur whose attorney had tried unsuccessfully for years to get him to plan. He left behind five kids who had never been trained, suddenly thrust into managing two operating businesses and complex real estate assets. The eldest child had to step up, juggling his own career and family, while grieving the loss of his father. “The lawyer had seen the possibility of a train wreck like this and was unable to help the father manage it more proactively. . . . ‘We have plenty of time,’” or so we think. But as this story shows, that’s not always the case.

Now the good story. Savlov’s mom is a role model for doing it right. After her husband died, she made a commitment to get her affairs in order. “Her driving priority was that all of us [three] siblings would continue to love and support one another. . . . After her death, she wanted us free of administrative hassles and surprises.” To that end, she did detailed planning, including “who would hold onto the infamous twisted soup ladle for future generations.” She also named Jeff as her healthcare representative to manage her end-of-life care, and they discussed her wishes in detail. What a gift to the Savlov siblings!

My niece Jessica Wilen, Ph.D. (an ICF-certified executive coach with significant experience as a psychotherapist and educator at Yale and at Washington University) writes a weekly newsletter called “A Cup of Ambition.” In her February 15, 2024 article, Jessica tackles “Why You’re Procrastinating . . . and What To Do About It.” Given that procrastination is the greatest obstacle in estate planning, I read it with great interest. Jessica covers five reasons why we procrastinate, and what to do about it.

1. You’re waiting for motivation to strike. It may never happen. What to do: Break the task into smaller sub-tasks. Doing step one motivates you to step two, etc.
2. You expect too much of yourself, beating yourself up for procrastinating, further paralyzing you. Everyone procrastinates. Don’t be so harsh on yourself.
3. As a perfectionist, you obsess over details, delaying completion of the task. Consider therapy and coaching to help you manage “toxic perfectionism.”
4. You’re trying to avoid conflict. You took on a task that you just don’t want to do. “Rip off the bandaid and be honest.” Otherwise, you build up anger and resentment.
5. You just don’t want to do it. Examine the consequences of not doing it, and if “you can live with the repercussions of not doing it, then this is your official permission slip to not do it.”

Jessica confesses how she put off opening a retirement account. Following her first piece of advice, she broke it into smaller tasks: (1) call the bank and get the paperwork; (2) then fill it out; and (3) then mail it in. One motivated her to do two; two motivated her to do three. Done!

We all have our own stories. As a young lawyer, I struggled with doing tasks that I dreaded. I remember when my boss “volunteered” me to solicit contributions for the Arts Council, and that uncomfortable task kept falling to the bottom of the stack. I got chewed out for that but learned a lesson. I adopted a methodology to do the most dreaded task first, and it really brings a gift of freedom. I give credit to Laurie’s mother Aimee Kriger for training us to “do it now.” She lived that way, and it’s part of the legacy she left to us. I highly recommend it.