At the time of writing this, the Red Sox are in the thick of their 2025 postseason push. Every game matters. Every at-bat and every out matters; September baseball is unforgiving, but also the most exciting. One bad at-bat, one bad inning, and your season can slip away. You can’t rely on one bat or one pitcher to carry you. Depth, balance, and timing make all the difference. Does your team get to ride the duck boats and wander down Boylston late at night? Or is your team also sitting on the couch in October?
Financial planning works the same way, especially when you’re in the retirement red zone, the five years before and after retirement. Like September baseball, every move counts more in this window than it did back in May and June when the season was just getting underway, much like the beginning of someone’s long-term career.
Trade Deadlines & Financial Strategy
Think of the trade deadline. It’s a balancing act between winning now and building for the future. Teams want to take advantage of what they have in the moment, but they can’t spend the entire farm system for a quick fix at first base. The best GMs find ways to strengthen their roster today while maintaining the long-term health of the franchise; those are the same goals as a family financial planner: build for tomorrow without sacrificing today.
That’s exactly what retirement red zone planning is about. You want to increase your income and opportunities as you approach retirement, but not at the expense of your future stability. Decisions about Social Security, retirement portfolio allocation, and withdrawal strategies carry far more weight in this window than they did when you were 35.
Injuries, Slumps, and Market Volatility
Injuries are around every corner in baseball. Roman Anthony’s oblique strain was a gut punch, a little more than a month out from the postseason, as would be a layoff or health issue, as you near retirement. That’s why depth matters. A team that builds around one star is exposed the moment something goes wrong; the same goes for portfolio diversification combined with financial planning.
In investing, it’s no different. Portfolios built around one “hot stock” or one asset class can leave you vulnerable when markets shift. Blue chips, like foundational players, give you consistency to build around. However, resilience stems from a balanced roster: growth, income, and cash reserves all play their role. Being able to adjust a plan and hopefully hold on to that playoff spot, or retirement date, is something your personal plan can help you answer.
Every Market Is Different and So Is Every Team
Not every team plays with the same resources. Some franchises have deep pockets; others build slowly (or never, ahem…Pirates). Your financial strategy/evolving strategies work the same way. The right strategy depends on your starting capital, time horizon, and risk tolerance. A DIY investor might piece together a plan on their own, but just like managing the Sox in crunch time, you may prefer to have a GM making those calls.
After all, wouldn’t you rather have someone else making the tough trade deadline decision than blaming yourself if it doesn’t pan out? Ask any Red Sox fans about Pablo Sandoval if you need a reminder of how wrong those calls can go. You don’t want to be explaining to your partner that you made the Pablo Sandoval or Mookie Betts trade equivalent of a bad financial decision.
Financial Strategy: Wildcards vs. Championships
The wildcard gets you in, but it doesn’t win you the championship. Short-term tactics might get you across the line this year, but the real goal is building a plan that can last a full season and beyond.
The question is: do you want to take those at-bats alone, or run your ideas past someone who’s seen the season play out before?
If you have retirement decision questions or would like to lament about Cora’s in-game strategies, please book a call. My door is always open.
This material is for general information and educational purposes only and is not intended to provide specific advice or recommendations for any individual.
Investing involves risk, including the loss of principal. There is no assurance that the views or strategies discussed are suitable for all investors or will yield positive outcomes.
Asset allocation does not ensure a profit or protect against a loss.
There is no guarantee that a diversified portfolio will enhance overall returns or outperform a non-diversified portfolio. Diversification does not protect against market risk.
