Master Your Money in 2024: The Complete Financial Health Check-In Guide

As the new year unfolds, it’s the perfect moment to evaluate your financial standing and ask yourself the tough questions that matter most. Whether you’re working toward wealth growth, retirement readiness, or simply better money management, having the right financial questions to discuss with your advisor can transform your entire year. This guide walks through the essential conversations you need to have and why January is your golden window for financial reset.

Investment Performance & Strategy: Your Portfolio’s Report Card

Start by understanding what worked and what didn’t last year. Ask your advisor to break down your portfolio’s performance against relevant benchmarks—not just overall returns, but how each component performed. If your tech-heavy holdings soared while bonds lagged, you’ve learned something crucial about your current risk exposure.

This leads naturally to your next financial questions: Does your investment strategy still match your life stage? If you’re approaching retirement, shifting toward a more conservative mix with higher bond allocation might make sense. Conversely, with a longer time horizon, growth stocks could serve you better. Markets constantly shift, so a static approach rarely delivers optimal results. Your strategy should adapt to market conditions, economic forecasts, and any personal life changes.

Understanding Fees and Custodianship: Transparent Money Management

Never skip the uncomfortable conversation about costs. Ask precisely how your advisor is compensated—whether through a flat fee, percentage of assets under management (AUM), commissions, or a hybrid model. Fee-only structures typically minimize conflicts of interest, while commission-based compensation can create incentives to recommend higher-commission products.

Equally important: know where your money actually lives. Third-party custodians like Fidelity or Charles Schwab provide crucial safeguards that prevent fraud and mismanagement. These firms offer FDIC and SIPC insurance protection and allow you to verify your holdings independently. This wasn’t always standard—the Bernie Madoff scheme highlighted why independent custodianship matters.

Tax Optimization: Lower Your Burden Now

January offers prime timing to discuss tax-saving strategies before tax season arrives. Ask your advisor about contributions to tax-advantaged accounts like 401(k)s, IRAs, and 529 plans. Tax-loss harvesting can offset capital gains strategically. Work together to identify deductions and credits applicable to your situation. When it comes to financial questions about minimizing tax liability, your financial advisor and tax professional should be completely aligned.

Retirement, Debt & Savings: Building Your Foundation

Three interconnected questions demand your attention: Are you saving enough for retirement? Should you accelerate your debt repayment? How can you strengthen your emergency fund?

Your advisor can assess whether your current retirement savings rate hits the mark and suggest adjustments—whether that means boosting contributions, exploring different investment vehicles, or extending your retirement timeline. Simultaneously, develop an accelerated debt repayment strategy if high-interest obligations burden you. Prioritize which debts to tackle first and explore consolidation options. Finally, ensure your emergency fund can cover three to six months of expenses.

Protection & Risk Management: Safeguarding What You’ve Built

Growing wealth matters, but protecting it matters equally. Discuss insurance coverage across life, disability, and long-term care scenarios. Review your estate planning documents—wills, trusts, powers of attorney, and beneficiary designations—to confirm they reflect your current situation and wishes.

Ask how rising interest rates affect your specific situation. Higher rates impact loan repayments, mortgages, and fixed-income investments differently depending on your portfolio composition. Your advisor can help you refinance debt or adjust your holdings accordingly.

Life Changes & Future Goals: Staying on Track

Major life events—marriage, starting a family, home purchases, career changes—carry significant financial implications. Alert your advisor to any upcoming transitions so adjustments happen proactively rather than reactively.

Reassess your financial goals holistically. Are they still realistic given your current circumstances? How far are you from key milestones like homeownership, education funding, or comfortable retirement? Let your advisor help recalibrate timelines and strategies.

Forward-Looking Strategies: Emerging Opportunities & Charitable Impact

Stay alert to new investment opportunities as markets evolve—sustainable investments, emerging markets, or innovative sectors might align with your goals and risk tolerance. Your advisor can evaluate which fit your overall strategy.

If charitable giving matters to you, explore tax-efficient approaches like donating appreciated securities or establishing donor-advised funds. This maximizes impact while optimizing your tax position.

Your Action Plan: Setting Priorities & Creating Momentum

End your meeting by asking your advisor to help you prioritize your financial goals for the year ahead. Clear priorities allow efficient resource allocation and provide a roadmap for tracking progress. This clarity reduces decision-making stress and prevents impulsive spending that derails long-term plans.

Preparing for Your Meeting: Do Your Homework

Bring financial documents—account statements, tax returns, insurance policies, and a written list of financial questions you want addressed. The more prepared you arrive, the more productive your meeting becomes.

If you don’t have an advisor yet, January presents the ideal recruitment window. Look for someone with solid credentials, relevant experience, and a fee structure that aligns with your values.

Final Thoughts

How often should these conversations happen? At minimum annually, but more frequently during major life transitions. Your financial advisor relationship works best when treated as ongoing partnership, not annual obligation.

Begin this year with intention. These financial questions and an open dialogue with your advisor create the foundation for a prosperous 12 months ahead. With proactive planning and expert guidance, you can transform financial anxiety into actionable confidence.

FAQs

Why meet with your advisor in January specifically? It’s ideal for reviewing the previous year’s performance, establishing goals for the new year, making necessary adjustments before the year unfolds, and addressing tax questions before season peaks.

How frequently should advisor meetings occur? Annual meetings are the baseline, but semi-annual or quarterly check-ins make sense depending on your circumstances. Significant life changes warrant additional meetings.

What shouldn’t you forget to bring? Account statements, recent tax returns, insurance documents, and a written list of questions maximize your time together.