Issue: Financial Professionals

Money talks, bullshit walks, but most of us would rather not listen. This issue, we're tackling one of the most uncomfortable yet crucial conversations: your relationship with financial professionals.

Whether you're flying solo, working with a team of advisors, or somewhere in between, your answer to this question reveals more than just your investment strategy—it unveils your entire approach to securing your family's future.

Today, we share two real stories that highlight why this conversation matters more than ever.

Mark's Wake-Up Call: A GenX Reality Check

Mark Rodriguez, 52, sits in his kitchen at 6 AM, laptop open, coffee growing cold. The numbers on the screen haven't changed in the past hour, but he keeps staring anyway. His 401(k) balance: $47,000. His savings account: $3,200. His retirement goal: "Sometime before I die."

"Nobody ever taught me this stuff," Mark admits, running his hands through graying hair. "My dad worked for the same company for thirty years, got his pension, and called it good. My mom balanced the checkbook. That was 'financial planning' in our house."

Mark's story mirrors millions of GenXers—the forgotten generation squeezed between Boomer pensions and Millennial financial literacy apps. He started his first "real job" in 1995, when 401(k)s were new and financial education was nonexistent. He contributed the minimum when he remembered, cashed out twice during job changes, and assumed he'd figure it out later.

"Later" arrived with his daughter's college acceptance letter.

"I'm looking at $200,000 in tuition costs, and I've got basically nothing saved," Mark says. "I always thought I'd catch up. There was always going to be more time, a better job, a raise that would fix everything."

The wake-up call came during a casual conversation with his brother-in-law, who mentioned his financial advisor's retirement projections. Mark realized he didn't even know what questions to ask, let alone who to ask them to.

"I've been avoiding financial professionals because I was embarrassed," he admits. "How do you tell someone you're 52 and basically starting from scratch? But avoiding them didn't make the problem go away—it made it worse."

Last month, Mark finally scheduled his first appointment with a certified financial planner. The conversation was humbling but not hopeless.

"She didn't judge me," Mark reflects. "She just laid out the reality: I can't retire at 65, but I can retire. It'll take aggressive saving, some career moves I've been putting off, and yes, working longer than I planned. But there's still a path forward."

Mark's advice to other GenXers in similar situations: "Start the conversation now. Today. Not when it's convenient or when you have more money or when you feel less stupid about it. The best time to plant a tree was twenty years ago. The second-best time is now."

Dorothy's New Chapter: Learning to Lead When You've Always Followed

Dorothy Chen, 73, inherited more than just her husband's estate when he passed two years ago—she inherited the weight of decisions she'd never had to make. For forty-seven years of marriage, Robert handled everything financial. She managed the household, he managed the money. It worked, until it didn't.

"Robert was brilliant with numbers," Dorothy explains from her sun-filled living room, surrounded by binders full of statements she's still learning to decipher. "He had spreadsheets for everything, accounts I didn't even know existed. I trusted him completely, which I now realize was both a blessing and a mistake."

The blessing: Robert left her financially secure with a diversified portfolio, a paid-off home, and detailed records of everything. The mistake: Dorothy had no idea how any of it worked.

"The first time I met with his financial advisor after the funeral, I felt like I was listening to a foreign language," she recalls. "Municipal bonds, asset allocation, required minimum distributions—I nodded along, but I understood maybe twenty percent of what he was saying."

Dorothy's situation is common among widows of her generation. Studies show that 85% of women will be solely responsible for their finances at some point, yet many have never been the primary decision-maker for major financial choices.

What makes Dorothy's story unique is what happened next. Instead of simply delegating to the existing advisor, she decided to educate herself.

"I realized I wasn't just managing money for me anymore," she explains. "I'm the steward of what Robert and I built together, and I'm responsible for how it gets passed to our children and grandchildren. I owed it to all of them to understand what I was dealing with."

Dorothy enrolled in a financial literacy course at her local community college, joined an investment club for women, and began interviewing different financial advisors to find one who would teach, not just manage.

"I needed someone who would explain the 'why' behind every recommendation," she says. "Robert's advisor was lovely, but he was used to talking to Robert, not to me. I needed someone who would respect that I was learning but not talk down to me."

The process revealed surprising gaps in the estate planning. Despite Robert's meticulous record-keeping, there were tax implications he hadn't considered and outdated beneficiary designations that could have cost the family thousands.

"I thought I was just learning to maintain what we had," Dorothy reflects. "Instead, I discovered I could actually improve on it. Last year, I restructured some investments to better support my grandchildren's education funds while reducing our tax burden."

Dorothy now meets quarterly with her financial advisor and has become the family's unofficial financial educator, teaching her adult children about estate planning and encouraging her grandchildren to start investing early.

"I spent forty-seven years trusting someone else to handle our most important decisions," she says. "I don't regret that—it worked for us. But I regret not being curious about it. Every spouse should understand the family finances, not just trust them to someone else."

The Conversation Starter

Both Mark and Dorothy's stories illustrate a fundamental truth: your relationship with financial professionals isn't just about money—it's about taking ownership of your future and your family's security.

Whether your answer to our card's question is "I have a comprehensive team" or "I've never talked to anyone about money," the important thing is honesty. From that honest assessment, you can build a plan.

Looking for a Financial Advisor - Questions to consider:

What's holding you back from seeking financial advice?

• If you work with advisors, do you understand their recommendations?

• How prepared are your spouse and children to handle finances if something happened to you?

• What financial conversations have you been avoiding with your family?

This Month's Family Discussion Prompt:

Share your financial comfort level with your adult children. Discuss not just your current situation, but your concerns, your goals, and your plan (or lack thereof). Consider involving them in a meeting with your financial advisor, or in the search for one.

Remember, the goal isn't perfection. It's preparation. And preparation starts with conversation.

Next issue, we'll explore the question: "How comfortable are you discussing your medical history and current health status with your family?" Until then, Pardon the Questions, but keep asking them.

Have a story to share or a question you'd like us to explore? Email us at [email protected]