Alisa Wolfson at MarketWatch brought me a reader question: 52 years old, about $1.2 million in assets, $900,000 of it in a 401(k) with $150,000 in Roth inside that plan, a $300,000 mortgage and a lake house, and a goal of retiring in three to five years. Can they do it themselves?
My answer was that the decisions coming up are bigger than the investing. The $150,000 in Roth inside that plan matters a lot depending on how and when you roll it. A rollover strategy in your first years of retirement, before Social Security and RMDs compress your income flexibility, is the kind of single decision worth more than a year of solid investment returns. The lake house adds another layer: property taxes, potential rental income treatment, liquidity planning and estate coordination. Each of those compounds the picture.
On how to pay for help, I was specific. At this asset level and life stage, flat fee is almost always better math. This reader is not adding significant new assets. What they need is hourly or retainer access to a planner for a specific set of decisions, not ongoing investment management.
DIY is fine for the portfolio. It is the tax and sequencing decisions in the first five years that are hard to unwind.
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