Forest Hill's Jeff Judge in MarketWatch: The DIY skill that gets you to $1.2 million isn't the one that gets

By Jeff Judge, CFP®, AEP®, ChFC®, CLU®, Managing Partner, Chesapeake Financial Planners, Forest Hill, MD.

A reader wrote to MarketWatch this week with a question I hear constantly. Fifty-two years old, $1.2 million saved, still working, and wanting to retire in three to five years. She had done it all herself for years and asked whether she still needed to pay for advice.

When MarketWatch asked me to weigh in, my answer was straightforward. The skill that gets someone to $1.2 million on their own is not automatically the skill that carries them cleanly through the next five years. In her case, $900,000 sat in a 401(k), and $150,000 of that was Roth money. How and when that gets rolled over is a decision that happens once, and getting the sequence or timing wrong hands the IRS money that didn't have to go there. Add a second home into the plan and you stack property taxes, rental income questions, and estate coordination on top of it.

This shows up constantly in Harford County and the Baltimore metro. Families in Fallston and retirees in Aberdeen who built real wealth on their own often assume the DIY approach that got them here will carry them the rest of the way. Commuters heading into Towson from this side of the county tell me the same thing: they don't need someone managing a portfolio every day, they need someone for a short list of decisions that only happen once.

The takeaway: if you're within five years of retiring and you've never used an advisor, the value isn't in ongoing management. It's in getting the handful of one-time decisions right.

This piece builds on "I'm 52 with $1.2M. I want to retire in 3 to 5 years. Can I make this happen myself?" in MarketWatch (August 2026).

Jeff Judge, CFP®, AEP®, ChFC®, CLU®, is Managing Partner at Chesapeake Financial Planners in Forest Hill, MD. Book an intro call.