By Spencer Sherman, MBA, CFP®

When I was 10 years old, my aunt and uncle and their children, who had lived across the street from me my whole life, disappeared. Suddenly, I no longer saw Aunt Lilly on my walk home from school. I never saw my cousins again. I didn’t know it at the time, but a money conflict led to my family’s division. The inability of the adults to have a courageous money conversation (CMC) caused a rift so great, my father found out about his sister’s death two years after the fact and 40 years after he last spoke to her.

When I became an adult, I asked my father about his sister. He said “I’ve come to a place of forgiveness for all the money that my brother-in-law stole from me and my business. But when I finally extended the olive branch to them, they had both already died.” That motivated me to reach out to my first cousin, Steve. Without any contact information, I hired a private detective — the most fruitful $500 I’ve ever spent. I agreed to fly to NYC to meet him. Over a pleasant lunch, I was aware that the conversation didn’t venture beyond safe and superficial topics.

Suddenly, I felt terrified (my knees were vibrating); when would I address the elephant in the room? What if I left without bringing up the topic? And then, in that moment, I remembered my father’s regret and inability to have a courageous conversation with his brother-in-law. I knew I had to say something, but how?

“Steve, do you know why our families have been completely out of touch for the last 35 years?”

“We just drifted apart. It happens.”

Did he not know? Or was he dodging my question? This was my moment to take a risk.

“Steve,” I began. “My understanding is that your father was stealing money from my father.”

He looked down and then slowly lifted his gaze and said “It’s true.”

“How do you know?” I asked.

“My father confessed to me before he died.”

In that moment, I realized that we had broken the family’s solemn rule to never speak about money. We were free not only to speak about taboo things, but to heal our family. And then I realized there’s a good reason why I’m helping people with money: I’m both healing myself and being a role model for others to address their money afflictions.

That was one of, if not, the most courageous money conversations I’ve ever had. What about you? Is there a conversation with a friend, child, parent, sibling, business partner, boss that you think about initiating, but keep postponing? Of course, there are times when a CMC might not go as planned. But, when I look back at my life, I can’t name a time when my intentional, well-planned money conversation didn’t produce more positive than negative outcomes. To me, this is a risk with outsized potential rewards. We have a bias to ignore the topic of money, but I’m suggesting you challenge yourself and do the opposite.

There’s a lot at stake with CMC’s. Here’s a list of potential conversations that could release blocked vitality and lead to a transformed relationship with the other party and with money itself:

1. Tell your adult children that you’re going to leave them less than they might be expecting. Or that you’re going to leave one child $1 million and the other child $500,000 [you’re going to leave one child more than the other] because of their different circumstances. From my experience, not having these conversations before death often has unintended consequences. Your children will assume that you left less money because of love. But, when it’s done in advance of death, it can be neutral at worst and connecting and empowering at best.
2. Tell your friend that you can’t afford the vacation trip or restaurant they’ve proposed. This again, is a chance for real intimacy with your friend, and to lower the stress to your body and to your wallet.
3. Tell your boss that you want to earn more money. If you don’t have this conversation your resentment might affect the quality of your work.
4. Tell your parents that they will run out of money if they don’t change their current lifestyle (or that they can spend more and not worry about leaving their money to you). This is an opportunity for intimacy and straight talk about the future.
5. Tell your spouse that you want to make financial decisions jointly. Despite that appearance of unity, you don’t feel like an equal partner. Again, not having this conversation, will likely lead to more resentment and a further erosion of connection.

Here’s how to have the conversation:

1. Write down your positive intentions for this conversation. Maybe it’s to get closer to your children, spouse, or friend. Maybe it’s protecting the financial wellness of your parents and yourself.
2. Role-play the conversation and ask a neutral person to act out the role of the other person. This neutral person will be much more objective and probably offer you some sound suggestions for what to say and not say. Experiment by asking the neutral person to reply with your biggest fears. When you debrief after the roleplay, listen to their feedback as well as to the feelings and intuition in your own body.
3. Set up a time to speak without interruption with the other person. Let them know the amount of time so you don’t feel rushed. Make sure it’s a comfortable space.
4. Start the conversation by saying something you appreciate about them. Next, say your intention and how you’re hoping that this conversation produces something positive for both of us. Stick to starting your sentences with the word “I” instead of “you.” In other words, say, “I’m concerned about you running out of money,” instead of “You’re terrible with money and almost broke.”

I cherish my belated relationship with Steve. Having a CMC, like any risk, might not produce a specific outcome, but it can heal and energize any relationship. It can also help you to feel powerful and effective with money.

Steve and I can’t recover the lost years, but when I called him last week, he told me he loved me. Hearing that made me see that taking risks can yield great rewards.

This article has been adapted from one originally published in Mindful Magazine.

Spencer Sherman, MBA, CFP® is a Search Inside Yourself mindfulness teacher (sourced at Google). He founded a sustainable financial firm and has an MBA from Wharton Business School. He is the author of The Cure for Money Madness and The Money & Spirit Workshop, and believes that all of us can feel ease and purpose with money, regardless of how much we have. His 30-year meditation practice supports him in helping others create an equanimous, powerful, and spacious relationship with money. He is a graduate of the Seven Stages of Money Maturity® Training and he has had a profound friendship with George for over 25 years.