I was speaking with a sad and dejected physician. She told me about the retirement plans she and her husband discussed a decade ago. Shortly after she retired she became a caregiver for her mother. Then her husband was diagnosed with disabling medical condition.
She said, “We had all of these plans, but we missed our window of opportunity. It’s shut now. We’re not going on that around-the-world cruise. Going to the grocery store is a production for us now.”
Regret is a paralyzing emotion. Your brain tells you, “If I made different choices in the past, I would have a better reality today.”
Regret can also be a powerful planning tool as you work with your doctor clients. You can say, “Imagine we’re having a conversation thirty years from now. What would you most regret if you didn’t take action today?”
The saver might say, “I regret all the times I said no to getting together with family opportunity because I was saving money. My niece was married in Italy, and I convinced my wife we could not afford to go. We could have afforded it! It’s just that I get anxious spending money.”
The spender might say, “I regret losing all that money in dumb doctor deals. Sometimes I imagine how different my life would be.”
Here are some more specific ways you can harness regret to work for you and your clients.
Using Regret as a Planning Tool
1. The “Future Self” Conversation Regularly ask clients to imagine themselves at retirement or key life milestones: “What would 65-year-old you most regret if we don’t address this now?” This creates emotional urgency around current decisions.
2. Identify Their Regret Profile Help clients recognize whether they’re typically “regret-of-action” people (who regret things they did) or “regret-of-inaction” people (who regret missed opportunities). Tailor your recommendations accordingly – conservative clients often need encouragement to take calculated risks, while impulsive clients need guardrails.
3. Create “Regret Insurance” Strategies Frame certain financial products and strategies as protection against future regret. Emergency funds become “peace of mind insurance.” Disability insurance becomes protection against the regret of not being able to provide for family.
Behavioral Interventions
4. The Two-Column Exercise When clients face major decisions, have them write potential regrets in two columns: “What I might regret if I do this” versus “What I might regret if I don’t do this.” This clarifies the true cost of inaction.
5. Set “Regret Minimization Deadlines” Create specific timelines for decisions to prevent endless deliberation. “We need to decide on this practice acquisition by March, or you’ll regret missing this opportunity when similar practices are selling for 20% more next year.”
6. Build in “Regret Prevention Reviews” Schedule annual meetings specifically focused on reviewing potential future regrets. Ask: “What financial decisions are you avoiding that might cause regret later?”
Addressing Spending Patterns
7. The “Values-Based Spending” Framework Help clients distinguish between meaningful expenses (the Italy wedding) and wasteful spending (speculative investments). Create spending guidelines that align with their core values to minimize both types of regret.
8. Implement “Regret-Proofing” Rules Establish automatic systems that prevent common doctor financial regrets: automatic retirement contributions, disability insurance riders, and investment guardrails that prevent emotional decision-making during market volatility.
9. The “Small Regrets vs. Big Regrets” Perspective Help clients understand that the regret of spending money on a family vacation pales compared to the regret of not having enough saved for retirement. Reframe short-term financial discomfort as prevention of long-term regret.
10. Document Decision Rationales Keep detailed notes about why clients made specific financial decisions. During future reviews, this helps them remember their reasoning and reduces the likelihood of second-guessing themselves, which often leads to poor reactive decisions.
These strategies transform regret from a paralyzing emotion into a practical planning tool that motivates better financial behavior and deeper client engagement.