The calendar is more than dates on a page. Spread across the year are financial actions and deadlines that can boost your tax savings, keep you compliant, protect your investments and make travel less stressful. Treat these moments as checkpoints—small, timely steps that add up to stronger money health.
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Start of the year: set the tone
- Collect and organize documents. Gather last year’s pay stubs, investment statements, receipts for deductible expenses and any tax forms you expect to receive. A tidy folder speeds up filing and planning.
- Review your tax withholding and estimated payments. Life changes—a raise, a new job or a side gig—can change your tax picture. Adjust withholding or estimated payments early to avoid surprises.
- Check retirement and health accounts. Confirm contribution amounts for retirement plans, IRAs and health savings accounts (HSAs). If you missed changes during the year, update payroll contributions now.
- Plan big purchases. If you expect to buy a house, car or make major home improvements, map out the timing so you can optimize financing and tax consequences.
Quarterly check-ins: stay on track
- Pay attention to recurring due dates. Many obligations—estimated taxes, sales tax filings, or business returns—come up on a quarterly cycle. Mark them on your calendar and set reminders.
- Rebalance investments. Regular rebalancing keeps your asset allocation aligned with goals and risk tolerance. Quarterly or semi-annual reviews work well for most investors.
- Monitor cash flow and expenses. A quarterly review of budgets, subscriptions and recurring charges can reveal savings and prevent costly surprises.
Mid-year review: adjust and refresh
- Assess progress toward savings goals. Are you on track for emergency savings, college funds or retirement targets? Make adjustments while there’s time to catch up.
- Look for tax-saving opportunities. Mid-year is a good time to consider tax-loss harvesting, changing investment allocations, or reviewing charitable giving strategies.
- Update insurance and estate basics. Revisit life, disability and property insurance coverage. Ensure beneficiaries on accounts and policies reflect current wishes.
Fall: benefits, enrollment and travel planning
- Open enrollment season. Review employer benefits, including health insurance, HSAs, dependent care accounts and voluntary benefits. Choosing the right plan for the coming year can save thousands.
- Lock in travel plans early. If you travel for work or pleasure, booking flights, hotels and car rentals well in advance usually gets better prices and flexible options. Check your passport and visa requirements before committing.
- Harvest points and perks. Use credit card rewards, loyalty points and airline miles before any expiration dates. Confirm whether your cards require travel notifications.
Year-end: the most powerful window for tax and investment moves
- Maximize retirement and tax-advantaged accounts. Make contributions to retirement accounts, HSAs and other tax-advantaged plans before the calendar or tax-filing deadline to capture full benefits.
- Review capital gains and losses. Consider selling losing positions to offset gains, or lock in gains strategically. Be mindful of holding periods and transaction timing.
- Use flexible spending account (FSA) balances. Some FSAs have use-it-or-lose-it rules or limited grace periods. Spend or plan accordingly before funds expire.
- Charitable donations and gifting. If charitable giving is part of your plan, year-end contributions can reduce taxable income while supporting causes you care about.
- Check required distributions and filing deadlines. If you are subject to required distributions from retirement accounts or have business filing obligations, review rules and timing so you don’t incur penalties.
Ongoing actions that protect your money health
- Keep an emergency fund. Aim to maintain several months’ worth of living expenses in liquid savings to weather job changes, health events or unexpected bills.
- Monitor credit and identity signals. Check credit reports periodically and use alerts for suspicious activity. Strong credit and quick detection reduce financial damage.
- Stay compliant with local obligations. For business owners: maintain licenses, file annual reports, and remit payroll and sales taxes on schedule. For individuals: stay current on local tax installments and property tax payments.
- Review subscriptions and recurring fees. Cancel unused services and renegotiate contracts where possible.
Quick annual checklist
- Organize income and tax documents
- Adjust withholding or estimated tax payments
- Max out tax-advantaged accounts where possible
- Rebalance investments and review asset allocation
- Plan travel and check travel documents and banking alerts
- Confirm insurance coverage and update beneficiaries
- File required business or personal returns on time
Small, well-timed actions beat last-minute scrambling. Use the calendar as a financial tool: mark key dates, set reminders and treat each checkpoint as an opportunity to save taxes, stay compliant and protect what you’ve built. If your situation is complex, consider consulting a tax professional or financial advisor to tailor deadlines and strategies to your needs.