Our past experiences don’t just live in our memory. If we let them, they can also be some of our greatest teachers that inform the choices we make today. I was recently lucky enough to attend the Schwab IMPACT conference in San Francisco, where this theme was literally center stage. Author Daniel Pink, who penned the popular book The Power of Regret was one of the featured speakers. Listening to him share his insights was a real highlight of the event.

We’ve all had experiences that make us look back and think, “If only I’d done things differently.” Pink breaks down regret into the four main categories below. What struck me most is how so much of this wisdom applies to financial planning.

• Foundation regrets: These are things that didn’t pan out the way we wanted due to a lack of responsibility on our part. That can include failing to save more money, eat better, exercise, or work harder in school.
• Boldness regrets: This refers to missed opportunities and the chances we didn’t take. Maybe you were too afraid to start that business you always dreamed of, or share your feelings with a romantic love that “got away.”
• Moral regrets: A moral regret refers to something you did that goes against your values. In other words, you behaved badly and wish you would have done better.
• Connection regrets: When you look back on your life, are there any relationships you wish you’d maintained? Maybe you had a falling out with a family member, or simply lost touch with an old friend.

Identifying Financial Regrets

The start of a new year is a wonderful time to reflect on the past 12 months and count our blessings. As you look back, do any financial regrets come to mind? Start by reflecting on your financial goals, which may be related to saving, investing, paying down debt, expanding in your career, or preparing for retirement. Taking stock of the year behind us can help bring things into focus.

Pay special attention to anything that didn’t work out the way you hoped. Maybe you didn’t:

• Hit your savings targets
• Take that professional risk you really wanted to explore
• Go on that dream trip
• Buy a vacation home for your family to make memories in
• Invest in a way that aligned with your values
• Consider what you really want out of retirement, which can help guide your financial plan

This exercise is valuable because it can clarify the things we feel regretful about. From there, you can use your financial plan to help set things right.

Using Regret as a Financial Tool

Don’t underestimate the power of hindsight. Once you’ve identified your regrets, they can be used as a compass that guides you back to your True North. Remember: Money is a tool that can help us live a life that supports our values, brings us joy, and leaves a positive legacy after we’re gone. Regrets are really just past experiences that don’t align with that idea. The good news? It’s never too late to set things right.

At JJ Burns & Company, we help our clients move through financial regret in a no-judgement zone. We don’t have to be defined by our past mistakes. Instead, we can use them to recalibrate how we move forward.

Remembering That Finances and Emotions Are Intertwined

When thinking about your regrets, you’ll probably find that it’s impossible to separate your emotions from the nuts and bolts of financial planning—and we shouldn’t try to. Retirement planning is a great example. For decades, I’ve been helping clients plan and save for fulfilling retirements. The first question I ask is usually some variation of, “What does retirement mean to you?” The way they answer inevitably steers the financial plan.

For example, one person might say they want to retire abroad and have far-flung adventures, while another dreams of doing volunteer work and spending more time with their grandchildren. Someone else might want to nurture a passion project or mentor up-and-comers in their industry. No matter how you answer, your vision can help us set a savings target and create retirement income streams to support you when you’re no longer working. It’s also important to consider the emotional transition of retirement, which is a huge (and often overlooked) factor.

The same applies to other major financial milestones, whether that’s launching or selling a business, building your legacy plan, or saving for your children’s education. Our financial goals are usually fueled by our desires and emotions. Understanding that is a key part of financial planning.

Putting It All Together

With 2025 now underway, we all have a wonderful opportunity to pause and reflect. Thinking about our regrets can put us on a financial path that’s more aligned with what really matters to us. When it comes to regret, we can either stew in the past and feel bad about ourselves, or forgive ourselves for being human and learn from those missteps.

At JJ Burns & Company, we prefer the latter. I’ll even take it a step further: I believe that regret can teach us powerful lessons about who we want to be and what we want to experience in this life. Connect with us today to help ensure that your financial plan reflects that.

financial planning retirement retirement planning