Before making financial decisions, get clear on what retirement looks like for you.

• Where do you want to live? Will you downsize, relocate, or stay put?

• What will your days look like without work on the calendar?

• What role will travel, hobbies, or family play in your life?

• Are your goals aligned with your spouse or partner?

Writing things down brings clarity and ensures your money is working toward something specific.

Retirement planning gets messy when you’re dealing with a scattered financial picture. Organizing your assets helps you see what you have and how to use it more effectively.

• List all accounts: 401(k)s, IRAs, pensions, brokerage, HSAs, annuities, insurance policies

• Categorize each by tax treatment: taxable, tax-deferred, or tax-free

• Identify accounts that are redundant or unnecessarily complicated

• Consolidate where appropriate to reduce noise and make your income plan easier to manage

A streamlined setup makes the rest of the planning process more efficient and less error-prone.

This is where a theoretical retirement becomes a real one. The focus shifts from growing wealth to using it wisely.

• Separate your spending into essentials (housing, food, insurance) and discretionary (travel, hobbies, gifts)

• Fund essential expenses with reliable income sources like Social Security, pensions, or annuities

• Use a guardrails-based system to adjust discretionary spending based on market performance

• Take advantage of Roth conversions during low-income years to reduce future tax exposure

• Sequence withdrawals tax-efficiently to avoid higher brackets and minimize the long-term tax bill

The right income strategy should give you structure, flexibility, and peace of mind without relying on guesswork.

Your portfolio has a different job in retirement. It needs to provide growth, income, and protection, all without taking on the wrong kind of risk.

• Assess how much market volatility you're comfortable with and how much liquidity you need to feel secure

• Place yourself on a grid that accounts for both risk tolerance and liquidity preferences, not just one or the other

• Adjust your allocation based on where you fall. Some clients need more stable income sources. Others can afford more flexibility

• Make sure your portfolio is stress-tested to handle a major bear market in the first five years of retirement

• Structure assets into time-based buckets for near-, mid-, and long-term needs

• Prioritize tax location. Income assets typically belong in tax-deferred accounts; growth assets are often better in Roths

• Consider tail risk hedging strategies to reduce exposure to catastrophic losses

• Some risks are worth taking. Others just increase the chance of loss without improving your outcome. Be cautious of investments that add risk without adding enough benefit.

Ultimately, your portfolio shouldn't be too aggressive or too conservative. Like Goldilocks, it needs to be just right — aligned with your specific goals, timeline, and temperament.

Healthcare planning is one of the most overlooked parts of retirement and one of the most expensive.

• Understand how Medicare works: Parts A, B, D, plus Medigap and Advantage plans

• If retiring before 65, make sure you have a plan for coverage until Medicare kicks in

• Budget for out-of-pocket healthcare costs. The average 65-year-old couple can expect to spend at least $165,000 during retirement

• More than half of retirees will need some form of long-term care, which can cost over $100,000 per year

• Consider hybrid long-term care insurance, earmarked reserves, or other funding options

Waiting until you need care is too late. Planning ahead means more options and fewer financial surprises.

A good financial plan includes making sure your wishes are clearly documented and easy to carry out.

• Review and update your will, powers of attorney (financial and medical), and healthcare directive

• Double-check beneficiary designations on retirement accounts, life insurance, and bank accounts

• Store these documents securely and make sure someone you trust knows how to access them

• Consider whether a trust makes sense based on your goals, family situation, or state laws

This isn’t just about legacy. It’s about making sure the right people can step in if something happens.

The emotional side of retirement is real. You’re not just leaving a job. You’re entering a new phase of life.

• Think about how you’ll spend your time once the structure of work is gone

• Explore purpose-driven activities like volunteering, travel, mentoring, or family involvement

• Build social connections outside of your professional identity

• Talk with your spouse or family about how your new routines might affect shared responsibilities or schedules

Retirement success depends just as much on your mental and social wellbeing as it does on your finances.

It’s not usually one big error that ruins a retirement plan. It’s a series of avoidable missteps.

• Holding the wrong kinds of risk at the wrong time or thinking diversification alone is enough

• Overlooking the long-term impact of taxes, especially when it comes to RMDs and IRMAA thresholds

• Chasing returns instead of optimizing income, cash flow, and tax efficiency

• Treating your financial plan as static instead of something that evolves with you

A good plan adjusts. A great one makes those adjustments before they’re necessary.