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Most Plans Get Reviewed Too Infrequently
A plan that made sense three years ago may not make sense today. Tax laws change. Goals shift. Life delivers events the original plan wasn't built around.
The Reassess & Refine step of Chesapeake Financial Planners' R.U.D.D.E.R. Method is how the firm ensures plans stay aligned with reality. But the maintenance schedule goes beyond an annual check-in. Seven categories of events should trigger a plan review regardless of when the last one occurred.
According to a 2023 Edward Jones survey, 56% of Americans haven't reviewed their financial plan in more than a year. 25% have never reviewed it at all. That's a substantial gap in a world where tax law, interest rates, income, and life circumstances can change significantly in twelve months.
Jeff Judge is direct about this: "Your plan is a living document, not a snapshot. The market doesn't wait for your annual review. Neither does a job change, a new grandchild, or a tax law update that narrows your Roth conversion window. We need to know about those things when they happen."
Here are the seven events that should send you back to the plan.
7 Events That Should Trigger a Financial Plan Review
1. A Job Change or Career Transition
A new position means new benefits to evaluate, a 401(k) to roll over or leave behind, a potential salary change affecting savings capacity and tax brackets, and possibly a new employer match to take full advantage of.
Leaving a long-term employer might involve unvested benefits, deferred compensation decisions, and a change in health coverage that carries Medicare implications for clients near 65. None of these are simple transitions. Each deserves a coordinated look.
2. A Major Income Shift
A significant increase or decrease in income changes contribution strategy, tax bracket positioning, insurance needs, and the logic behind existing recommendations.
A business owner with a record revenue year has Roth conversion and deferred compensation windows that may not open again the same way in a slower year. A client moving from two incomes to one needs the plan to reflect that reality now, not at the next scheduled review. The IRS 2024 401(k) contribution limit is $23,000 ($30,500 for those 50 and older) — if your income has changed substantially, it's worth revisiting whether you're using these limits as effectively as you can.
3. Marriage or Divorce
Marriage changes tax filing status, beneficiary designations, insurance coverage, and potentially the estate plan. A new spouse's assets and liabilities become part of the shared financial picture.
Divorce reverses most of that: it separates accounts, changes beneficiary designations that often get missed, creates alimony or child support income considerations, and splits retirement assets through a qualified domestic relations order (QDRO). Jeff is specific about the risk here: "We've seen clients go through a divorce and not update their ex-spouse as the beneficiary on a $400,000 retirement account. That's not a mistake anyone intends to make."
4. Retirement — or the Years Just Before It
The five years before a planned retirement date are the most consequential for financial planning. Social Security timing, Medicare enrollment, Roth conversion windows, sequence of returns management, and the shift from accumulation to income distribution all require coordinated attention during this period.
The plan should be updated at minimum annually in these years, more often if circumstances shift. Many of these decisions are difficult or impossible to reverse once made. Getting them right requires current information.
5. A Significant Inheritance or Wealth Event
Receiving an inheritance, a settlement, or proceeds from a business transaction changes the plan. A large influx of assets carries tax implications, allocation implications, and potential estate planning implications.
A plan update immediately following a wealth event produces better outcomes than one done twelve months later, after several decisions have already been made by default. The window for optimal tax positioning is often short.
6. A Change in Tax Law
Tax legislation doesn't announce itself clearly to individuals. The SECURE Act and SECURE 2.0 Act changed inherited IRA rules and RMD ages for millions of people. The potential expiration of many Tax Cuts and Jobs Act provisions at the end of 2025 is a known inflection point that is already affecting Roth conversion strategy for clients with larger traditional IRA balances.
When tax law changes in a material way, the plan should be reviewed to assess what's affected. Jeff puts it plainly: "Don't wait for something to cost you money to find out the rules changed."
7. A Health Change or Long-Term Care Consideration
A new diagnosis, a change in health status, or simply reaching the age where long-term care planning becomes relevant is a trigger for a plan review. Health changes can affect life insurance coverage, disability insurance needs, long-term care insurance eligibility, and the timeline assumptions in the retirement income plan.
Long-term care planning is frequently deferred longer than it should be. Insurance premiums increase significantly with age, and some clients become uninsurable before they've had the conversation about whether coverage is appropriate for their situation. Earlier is almost always better here.
How the Reassess & Refine Step Works in Practice
The final step of the R.U.D.D.E.R. Method isn't simply an annual calendar event. It's an ongoing commitment to keep the plan aligned with the life it's supposed to serve.
Chesapeake reviews each client's plan on a scheduled basis and after any of the events above. The output isn't necessarily a full plan rebuild. It's targeted updates that address what's changed while leaving intact what still makes sense.
Jeff describes the goal clearly: "The plan should always reflect your actual situation. Not who you were when we first built it, but who you are now and where you're trying to go from here. The Reassess step is how we make sure that's always true."
Frequently Asked Questions
How do I let Chesapeake know when one of these events happens?
Reach out when something significant changes. You don't need to wait for a scheduled review. The R.U.D.D.E.R. Method is built around ongoing communication, not a once-a-year call.
What if I'm not sure whether my situation warrants a review?
If you're asking, it probably does. A brief conversation is enough to determine whether a full update is needed or whether the change is minor enough to note for the next scheduled meeting.
How often does Chesapeake schedule routine plan reviews?
At minimum annually. Client situations that involve more complexity, particularly in the years surrounding retirement or a major transition, often warrant more frequent reviews.
What does a plan review actually produce?
A review produces targeted updates to the recommendations, sequencing, and assumptions that have been affected by what changed. It may also identify new opportunities or risks that the previous version of the plan didn't address.
Keep Your Plan Current
If any of these events have occurred recently and your plan hasn't been updated to reflect them, schedule a no-obligation consultation with Jeff Judge at Chesapeake Financial Planners. The Reassess & Refine step of the R.U.D.D.E.R. Method is built for exactly this.
The information provided is for educational purposes only and should not be construed as investment advice. Investment strategies should be tailored to individual circumstances, risk tolerance, and goals. Past performance doesn't guarantee future results. Consult with qualified financial professionals regarding your specific situation.
Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through Great Valley Advisor Group, a registered investment advisor and separate entity from LPL Financial.
Chesapeake Financial Planners | 2402 Scotlon Ct, Forest Hill, MD 21050 | (410) 652-7868 | www.chesapeakefp.com