Brain Dump #2: The Cost of Avoiding Hard Conversations

Note: Brain Dumps aren’t articles—they’re just thoughts I find worth sharing. Some will be short, others long or convoluted. Take what resonates.

It’s always sad to see relationships—whether professional or personal—fall apart simply because people failed to address challenges, differences, and expectations early.

Often, we hold back from giving feedback because we think it’s too early or because we want to avoid awkwardness. But by delaying these difficult conversations, we risk creating a situation that is not only emotionally draining but also financially costly—for others and often for ourselves.

My Advice:

• Have the conversation early. Sit down with the person and share your discomfort.
• Give the feedback you’ve been holding back. There may never be a “perfect moment.”
• Push back on bad ideas. If you’re being asked to endorse something that doesn’t sit right, speak up.
• Clarify expectations—early and often. Make sure you’re aligned before investing more time, money, and well-being into a partnership.

The result? Some relationships and projects will end sooner. But the ones that survive will flourish, because they were built on transparency, alignment, and trust.

As Mark Cuban once said about high-risk, high-reward endeavors—friendships, marriages, companies: “You only have to be right once.”