The Beach House Decision That Reminded Me Why I Became a Financial Advisor

By Roger Bair, MSF, CFP®, CIMA® 

“Am I going to be okay?”

It’s the question every newly widowed person asks—sometimes out loud, sometimes just to themselves at 3:00 a.m. When a woman in her 60s was referred to our office after losing her husband, she was asking that question too. Her husband, a physician, had handled all the finances. Now she was alone, overwhelmed, and terrified of making a mistake.

She needed someone she could trust. She needed to know if she could make it.

When Everything Feels Overwhelming

Her husband had done a good job with their money, but like many people, he’d kept assets spread across multiple accounts. She had no idea where to start or what any of it meant.

If you’ve been in this situation, you know the feeling. While you’re grieving and exhausted, suddenly you’re supposed to make major financial decisions about things you may have never handled before.

As Bob, one of our CPAs, and I began working with her, we knew we had to move quickly without adding to her emotional burden. We broke everything into manageable pieces, consolidating accounts tax-efficiently while building her trust one small step at a time.

What I realized early on was that because she wasn’t financially sophisticated, our responsibility to her was greater than usual. If we told her to do something, she would do it. I had to be right. We absolutely couldn’t be wrong.

You Don’t Have to Do This Alone

After each meeting with this client, Bob and I would huddle: What did we hear? What’s our next move? How can we take small steps for her while making giant leaps in organizing her financial life? If I had a complex estate planning question, I could tap Drew or other colleagues. 

We consolidated her accounts and went through her tax returns. We reviewed her insurance policies, examined her estate plan, and created comprehensive financial projections. We put together what we call a Financial Physical™, a complete picture of where she stood and what needed attention. We brought order to what had initially seemed chaotic, at a pace she could handle.

The Question That Really Matters

By the fall of that first year, we’d made tremendous progress. She was feeling better, though grief doesn’t follow a timeline. Her finances were consolidated and organized. We’d updated her financial and healthcare powers of attorney and worked with an estate attorney to set up a trust in her will.

Most importantly, we could finally tell her with confidence: “You’re going to be okay.”

That’s when she asked me something that had nothing to do with spreadsheets or account balances.

“Roger,” she said quietly, “each year, my husband and I rented an expensive beach house at the Outer Banks for our large extended family. Can I still do that?”

I didn’t need to run the projections right then, though I would later. At that moment, I knew the answer went beyond the math.

“Let me tell you something,” I told her. “This is a life decision. You have four children with spouses and extended families. We need to support you in living your best life. You must rent this house and be with your family.”

The numbers did work out fine. But even if they had been tight, we would have found a way. This wasn’t about dollars and cents, it was about relationships, memories, and giving her permission to keep living—not just surviving.

What This Means for You

Five years later, she passed away rather suddenly. When I heard the news, I thought immediately about that beach house. It had cost around $12,000 each year, and it was worth every penny.

If you’re reading this as someone who recently lost a spouse, here’s what I want you to know:

Your money should work for you, not control you. It shouldn’t dictate whether you can gather your family at the beach each summer or limit the experiences that matter most. Yes, we need to make sure you won’t run out of money. But we also need to make sure you actually live.

This is what financial wellness really means. There has to be a balance between shielding your future and living your life today.

At Financial Consulate we understand that when you come to us after losing a spouse, you’re not just looking for someone to manage your accounts. You’re looking for someone who understands what you’re going through, who will move at your pace, and who will help you make decisions with confidence, not fear.

We’re CFP® professionals and CPAs who, working as a team, prioritize education, not sales. In many cases, at the end of meetings, we hug. Because this work is deeply personal, and we treat it that way.

Sometimes the most important financial advice we give has nothing to do with investment returns. Sometimes it’s simply saying, “Yes, you’ve worked hard and saved well. Now go make those memories with your family.”

That beach house? That was money well spent. And helping her get there… that’s why I do this work.

If you’re facing financial decisions after losing your spouse and aren’t sure where to start, I’d be honored to speak with you. There is no pressure—just a conversation about your situation and whether we might be able to help. You can reach me and our team at (410) 823-7283, or you can schedule a time to talk at your convenience through our website.

You don’t have to figure this out alone.

Frequently Asked Questions About Financial Planning for Widows

What should I do if I’m newly widowed and overwhelmed by finances? 

Start by finding a fee-only fiduciary advisor who can help you organize accounts, review your tax situation, and create a comprehensive plan. Look for a team approach where CPAs and CFP® professionals work together.

How do I know if I can afford to maintain my lifestyle after my spouse dies? 

Start by listing all your income sources (Social Security, pensions, investment accounts, life insurance proceeds) and your monthly expenses. A financial advisor can use projection software to model different scenarios and show whether your money will last based on your spending needs, life expectancy, and investment returns. This analysis should account for inflation, healthcare costs, and major expenses like home maintenance or family gatherings.

Should I hire a financial advisor or a CPA after losing my spouse? 

Ideally, you need both working together. You’ll face immediate tax issues (filing final returns, handling inherited accounts) and ongoing financial planning needs (managing investments, estate settlement, retirement income). Look for an advisory firm where CPAs and financial planners collaborate, so you don’t have to coordinate between separate professionals during an already difficult time.

About Roger

Roger Bair, MSF, CFP®, CIMA®, is a Senior Wealth Advisor at The Financial Consulate, where he helps clients bring clarity and confidence to their financial lives. With more than 30 years of experience in the investment and advisory profession, Roger guides individuals and families through major life transitions with thoughtful planning and steady support. He is especially passionate about helping clients align the financial and non-financial parts of their lives—conversations that often bring a sense of relief and reduce the stress many feel around money. Roger advises on tax, estate, investment, and retirement planning, coordinating each strategy within a cohesive, purpose-driven plan.

Roger holds a Master of Science in Finance from Loyola University Maryland, is a graduate of McDaniel College, and maintains the CERTIFIED FINANCIAL PLANNER® and Certified Investment Management Analyst® designations. Known for his personable style and calm, constructive guidance, he builds lasting client relationships through trust and clear communication. Outside the office, Roger enjoys spending time with his family (especially his children and grandchildren) grilling, gathering outdoors, and creating memories together. To learn more about Roger, connect with him on LinkedIn.