9 factors to consider in your pre-retirement years

For many people approaching retirement, the focus shifts from how much money they need in savings to how they can turn that savings into a life they enjoy without running out of choices later.

For this reason, the years leading up to retirement can feel like a mix of opportunity and uncertainty. “Even for people with strong incomes, financial complexity tends to increase over time,” said Sascha Fincham, financial planning manager at BOK Financial®.

Taxes, healthcare decisions, aging parents, concentrated investments and competing goals all can add to that complexity—and, with retirement fast approaching, the stakes are high. “Markets move unpredictably, and big decisions—such as when to stop working or when to take Social Security—can carry long-term consequences,” Fincham said.

Financial planning helps bring clarity to this chapter. It coordinates income, investments, taxes, healthcare and lifestyle goals so people approaching retirement can make decisions confidently. As Fincham puts it, “A plan connects today’s realities with tomorrow’s goals—so you’re choosing with intention, not reacting to the moment.”

Below are the essential areas to consider if you’re approaching retirement—and how a well‑built plan ties them together.

1. Start with lifestyle and goals, not numbers
Before running projections, define the retirement you want.
• What does a fulfilling week or year look like?
• Will you travel often, spend more time with family or pursue hobbies?
• Are you thinking about downsizing your home, relocating or keeping multiple properties?
• Will you support children, grandchildren or aging parents?

A financial plan translates your goals into clear spending categories: essentials, lifestyle choices, one‑time expenses and family or charitable giving. “Clarity about what ‘great’ looks like in retirement is the first metric that matters,” Fincham said. “Once you have that, the math will follow.”

When your goals are clear and quantified, planning becomes about aligning resources, not guessing or hoping you’ve saved enough, she continued. “Decisions get easier when every dollar has a job tied to your priorities.”

2. Build a reliable retirement paycheck

Retirement requires a shift from saving to spending. A financial plan helps create a dependable income structure, so your money lasts through changing markets and long lifespans, Fincham explained.

A strong retirement income plan addresses:

• Where income will come from (such Social Security, pensions, investments and real estate).
• When to claim Social Security and how timing affects lifetime benefits.
• The optimal withdrawal order from taxable, tax deferred and tax-free accounts.
• Cash reserves for short-term needs and unexpected events.
• Spending guardrails that guide adjustments during market swings.

“Think of it as building your own paycheck—one that’s resilient to markets and personalized to your lifestyle,” Fincham said. “Instead of wondering if you can afford something, you know what’s sustainable, and how to adapt if conditions change.”

3. Protect yourself against market downturns

One of the greatest risks early in retirement is experiencing a market drop right when you begin withdrawing from your portfolio. This is known as sequence-of-returns risk, and it can reduce long-term sustainability even if average returns look fine.

To help avoid this risk, you need a planning-driven strategy that organizes money by timeframe. This includes:

• Cash for near-term expenses and emergencies.
• Stability assets (short-term bonds, fixed income) for the next several years.
• Growth assets (stocks, equity funds) for long-term inflation protection.

With this approach, you avoid being forced to sell long-term investments during a downturn because you have dedicated buckets for different time horizons. “We don’t try to predict every market move,” Fincham explained. “We design cash‑flow buffers so you’re not forced to sell assets at the wrong time.”

4. Use tax planning to keep more of what you’ve earned

Taxes don’t disappear once you retire. In fact, tax efficiency often becomes one of the biggest levers for improving lifetime outcomes. For this reason, effective retirement tax planning includes:

• Choosing which accounts to draw from first.
• Evaluating Roth conversions during low-income years.
• Planning for Required Minimum Distributions (RMDs).
• Coordinating Social Security and investment income to avoid bracket creep.
• Managing capital gains and annual tax drag.

Smart tax sequencing such as this can extend portfolio longevity, increase after-tax income and avoid future tax surprises, according to Fincham. “A few well‑timed moves, like Roth conversions in low‑tax years, can compound into meaningful savings,” she said.

5. Make healthcare a core part of the plan

Healthcare is often one of the largest, and most misunderstood, retirement expenses. Costs include more than Medicare premiums; they also involve deductibles, dental and vision care, prescriptions and long term care considerations. Consequently, you need a plan that accounts for:

• The transition from employer coverage to Medicare.
• Supplemental coverage decisions.
• Realistic healthcare inflation.
• Options for long-term care (insurance or self-funding).

“When healthcare is built into the plan, it becomes predictable instead of a major unknown,” Fincham explained. “Plan for long‑term care sooner rather than later. Coverage is typically more affordable, and you tend to have more options available, the earlier you evaluate it.”

6. Align your insurance with your new life stage

As you enter retirement, your insurance needs change. The focus shifts from protecting income to protecting assets, lifestyle, and family.

Key areas to review include:

• Life insurance, including determining whether your existing coverage is still adequate.
• Liability protection (umbrella insurance).
• Home, auto and property coverage based on new routines or residences.

“A proactive review ensures you’re not under or over insured and that coverage reflects your actual risk profile,” Fincham said. “Right‑sizing coverage protects what you’ve built without paying for protection you no longer need.”

7. Simplify and organize your financial structure

Many people approach retirement with a complicated mix of old 401(k)s, IRAs, brokerage accounts, savings vehicles and outdated beneficiary designations. “This complexity raises the likelihood of mistakes and can make managing finances feel overwhelming,” Fincham noted.

Financial planning helps:

• Consolidate accounts where practical.
• Streamline investment strategy.
• Update beneficiaries and titling.
• Create a simple system for required withdrawals and ongoing management.

Simplicity is a risk‑management tool,” Fincham said. “When accounts and beneficiaries are organized, fewer things can fall through the cracks.

8. Make legacy and giving intentional

Legacy planning is not just about estate documents; it’s about ensuring your financial structure matches your values and goals.

Planning includes:

• Reviewing wills, trusts and powers of attorney.
• Coordinating these documents with account titling and beneficiaries.
• Planning tax efficient giving strategies, if meaningful to you.

An intentional approach reduces future complications for your family and helps direct your wealth where you want it to go, but your legacy plan must be updated regularly, Fincham said. “Treat your estate plan like living infrastructure; review it after major life events and at regular intervals,” she explained.

9. Use your pre‑retirement years strategically

Decisions made in the five-to-10-year window before retirement—such as work adjustments, tax planning, saving rates, debt management and investment allocation—can meaningfully shape your flexibility later.

With this in mind, your financial plan should evaluate scenarios such as:

• Working part time versus fully retiring.
• Moving or downsizing.
• Paying off a mortgage versus having more money on hand.
• Diversifying concentrated stock or business interests.

Seeing the trade-offs clearly helps you choose the path that best supports your long-term goals.

“These years are leverage years,” Fincham said. “Small, deliberate changes now can create more freedom later.”

When coordinated, these elements support each other instead of competing. Retirement becomes less of a leap and more of a guided transition—built around clarity, confidence and flexibility.