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Insights from The Mind Money Spectrum Podcast Episode #154
Seasonal Financial Planning: Focusing on the Right Topics at the Right Time
Published: Tue, 14 Oct 2025 06:00:00 -0400
Managing your financial life can often feel like juggling too many balls at once—taxes, investments, insurance, retirement savings, estate planning, and more. For high-performance professionals pursuing financial security and freedom, this sheer volume of tasks can seem overwhelming. But what if you could break down your financial to-do list into manageable, timely pieces, aligned with the rhythms of the calendar year?
Welcome to the concept of seasonal financial planning. As a fee-only fiduciary financial advisor, I encourage clients to leverage the timing and natural deadlines in the financial calendar to focus on what really matters, when it matters most.
This approach not only makes your planning more effective but reduces the stress of managing everything simultaneously. By prioritizing the right topics in the right season, your financial picture ultimately runs like a well-oiled machine.
Why Seasonal Financial Planning Matters
When you look at financial planning as an ongoing process, it’s important to remember that many financial tasks have natural deadlines and best times to address them. Tax deadlines occur once per year; employer benefits open enrollment happens annually and often only lasts a few weeks; year-end is crucial for tax-loss harvesting and retirement account strategies. Setting up regular, seasonal check-ins helps prevent important issues from slipping through the cracks and eliminates the feeling of looming, unmanageable workloads.
Think of your financial planning like maintaining a high-performance vehicle. You don’t overhaul the engine every day, but you do regular oil changes, tire rotations, and safety inspections according to the manufacturer’s schedule. The same principle applies to your finances: establish a rhythm of care, checkups, and maintenance at just the right times.
Fall: The Season of Open Enrollment and Life Insurance Review
For most professionals, fall is a crucial season because of the open enrollment period for employee benefits. This window, often stretching from September through November, is your annual opportunity to:
- Review and select health insurance plans
- Adjust Flexible Spending Accounts (FSA) or Health Savings Accounts (HSA) contributions
- Evaluate group life insurance coverage available through your employer
- Make changes to other employee benefits such as disability insurance and commuter benefits
It’s during this period that I strongly recommend clients take a close look at their life insurance needs. Job changes, new mortgages, or starting a family can drastically alter the amount of coverage required. Employer group life insurance is often a convenient and affordable option, but it might not be sufficient for your total protection. Fall is a natural time to ask:
- Has my income or financial responsibility changed?
- Do I need to increase or supplement my life insurance?
- Is the provider or policy changing in the new plan year?
Beyond insurance, fall also tends to bring tax-related deadlines for business owners, especially those who file tax return extensions. If you operate a business or have a solo 401(k), aligning your retirement contributions with your tax situation usually happens this time of year. The true bottom line here is to use fall for financial checkups — reviewing known priorities with an eye toward setting you up well for the last quarter and the coming year.
Winter (December to Early January): Finalizing Year-End Strategies and Setting Up the New Year
The close of the calendar year is the busiest time for financial planning activities that directly impact your taxes and investments. Key tasks to consider are:
- Year-End Tax Planning: Harvest tax losses to offset gains, plan Roth IRA conversions, and prepare for any required minimum distributions (RMDs) if you’re age 73 or older as of 2025.
- Optimizing Retirement Contributions: If you haven’t maxed out your 401(k) contributions, this is often the last chance to do so for the current year.
- Preparing for Equity Compensation: For professionals with stock options or RSUs, year-end is often critical to determine exercise strategies that minimize tax consequences.
December is generally a time to solidify your game plan, not to make rushed decisions. I typically advise clients to finalize strategy discussions early in December and then execute specific financial moves before year-end deadlines. This helps avoid the stress of last-minute errors and maximizes tax efficiency.
As January arrives, it’s also important to set up new-year financial rhythms, such as confirming your updated 401(k) deferral rates, establishing systematic investment plans, and if applicable, beginning to take RMDs in a monthly or lump sum fashion.
Spring: Filing Taxes and Portfolio Sanity Checks
Spring is often associated with tax filing and the wrap-up of tax-related financial planning:
- Tax Filing and Refund Planning: Whether you’re filing on time or with an extension, you want to ensure that all income sources, especially from investments and equity compensation, have been properly reported.
- Reviewing Beneficiary Designations: It’s critical to confirm that your retirement plans and investment accounts name the correct beneficiaries. Life changes such as marriage, divorce, or births can necessitate updates.
- Estate Plan Review: Spring offers a good opportunity to revisit your wills, trusts, and healthcare directives to ensure your documents reflect your current wishes.
- Portfolio Checkups: After tax season, it’s useful to review your investment allocations and rebalance if needed, keeping your asset mix aligned with your risk tolerance and goals.
Importantly, spring tends to be lighter in terms of urgent financial moves, allowing space for reflection and strategy adjustments.
Summer: Maintain Momentum Without Overwhelm
Summer is typically the most challenging season to schedule financial focus, simply because kids are out of school and vacations take priority. In recent years, I’ve adopted a light-touch monthly check-in approach with clients during summer months, sending brief, no-pressure reminders or checking if any looming issues need attention.
Summer should be about maintaining your financial health without pressure. This can mean ensuring ongoing investment contributions are on autopilot, reviewing cash flows, or simply letting your well-structured plans work in the background. It’s okay to take a step back during this period but remain mindful so nothing festers unattended.
Breaking It Down: Checkups vs. Check-Ins
One framework I use to keep clients on track is dividing their financial journey into two categories:
- Checkups: These are more comprehensive reviews that happen two to four times per year, depending on your needs. During checkups, we address substantial items like insurance coverage, retirement planning updates, estate changes, and tax strategies.
- Check-Ins: These are lighter touchpoints, often monthly, where you receive reminders or quick prompts. Most months, these won’t require action—but if something like open enrollment or a tax deadline appears, the check-in serves as a gentle nudge.
This cadence prevents you from becoming overwhelmed, ensures key issues don’t linger unresolved, and creates accountability to take care of one thing at a time.
Why Ongoing Partnership Makes All the Difference
The reality is that most people do not complete their financial to-dos on their own without some form of accountability. It’s easy to say, “I’ll do that next month,” only for months or years to pass without action. Working with a fiduciary advisor—someone who acts in your best interest—helps cut through inertia. We create a prioritized checklist tailored to your life and financial goals, then chip away at it together, one essential task at a time.
Sometimes just getting started is the hardest part. But with that momentum, your financial engine begins firing on all cylinders. Your portfolio stays aligned, your insurance protects your family, taxes are optimized, and your retirement plan becomes a powerful wealth creator. By following a seasonal financial planning rhythm, you transform your finances from chaos to confidence.
Action Steps For Your Seasonal Financial Planning
- Mark Your Calendar: Note important financial deadlines and open enrollment periods early to plan ahead and avoid rushed decisions.
- Schedule Regular Checkups: Aim for at least two comprehensive financial reviews annually to cover evolving priorities and updates.
- Use Monthly Check-Ins: Whether from your advisor or self-directed, maintain financial awareness with brief reminders on what to focus on each month.
- Prioritize One Thing at a Time: Avoid getting overwhelmed by breaking your checklist into manageable tasks. Celebrate progress, no matter how small.
- Maintain an Ongoing Relationship With a Fiduciary Advisor: An advisor committed to your best interest can help guide the seasonal planning, provide accountability, and adjust strategies as your life changes.
Final Thoughts
Seasonal financial planning aligns with the natural ebb and flow of your personal and professional life. It’s a practical, sustainable way to pursue financial security and freedom without unnecessary stress. Whether it’s reviewing your life insurance during open enrollment or finalizing your-year end tax moves, focusing on the right financial topics at the right time will keep your wealth engine running smoothly for years to come.
If you’re ready to refine your financial planning rhythm and stay on top of your priorities with purpose, let’s connect. Together, we’ll build a plan that respects your time, goals, and need for clear accountability—so your money truly works for the freedom you seek.
Stay focused, stay disciplined, and invest forever.
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Need More Help?
If you’re ever in need of guidance, these blog posts may be of help. But be sure to contact a financial, tax, or legal professional for guidance and information specific to your individual situation. And as always you can reach out to me directly here with questions or concerns about your personal situation.