5 Common Financial Planning Questions
By Luke Sullivan on October 28, 2026
How much money do you need to retire? It’s one of the most common questions people ask when evaluating their financial future. Some look to national averages, others compare themselves with friends or colleagues, and many rely on familiar retirement savings formulas.
But the amount one person needs may be entirely different from what another person requires.
In this week’s episode of Upticks, Jake Falcon welcomes Jake Cross, CFP®, Director of Financial Planning and Partner at Falcon Wealth Advisors, to discuss common financial planning questions. Their conversation explores how spending, investment risk, healthcare expenses, taxes, and changing personal circumstances influence retirement readiness.
Why comparing retirement savings can be misleading
It’s natural to wonder how your savings compare with other people your age. Someone approaching retirement might see a headline suggesting a particular account balance is necessary or hear that a neighbor has accumulated a certain amount. Those comparisons provide limited information.
Two households with identical investment balances may have entirely different financial situations. One may have a pension, limited debt, and relatively modest expenses. Another may have higher spending, different tax considerations, and substantial financial responsibilities.
Even the types of accounts matter. Assets held in traditional retirement accounts, Roth accounts, and taxable brokerage accounts can produce different tax consequences when money is withdrawn. Jake Cross encourages people to evaluate their own circumstances rather than adopting another household’s financial decisions. A strategy that makes sense for a friend or sibling may not be appropriate for someone with different assets, income needs, and objectives.
How much money do you need to retire?
Retirement readiness is often reduced to a single number. The 4% withdrawal guideline is one commonly referenced approach. Another involves multiplying a person’s salary by a certain amount to estimate a retirement savings target. These formulas can offer general reference points, but they cannot fully account for individual circumstances.
Someone earning $250,000 annually may spend only a portion of that income and save the remainder. Another household earning considerably less may spend nearly everything it earns. Using salary alone to determine retirement needs would overlook that distinction.
Jake Cross explains that Falcon begins with cash flow. The planning process considers expected spending, retirement timing, investment assets, account types, Social Security, pensions, and other sources of income. These factors are evaluated together to estimate the withdrawals a household may need from its investments.
The analysis also considers market fluctuations and the possibility that investment returns may occur in an unfavorable sequence, particularly early in retirement. The resulting financial plan provides a framework for evaluating retirement readiness. It is not a guarantee of future results, and the assumptions require ongoing review as circumstances change.
Your portfolio should support the financial plan
Investment performance matters, but it should not be evaluated without considering the purpose of the portfolio. Jake Falcon and Jake Cross discuss how investors can become overly focused on comparing their returns with a benchmark or another person’s investments. A portfolio designed to support regular retirement withdrawals may have different objectives and risks than a portfolio intended primarily for long-term accumulation.
For example, someone drawing income from investments may benefit from maintaining appropriate reserves and fixed-income exposure to reduce dependence on selling stocks during unfavorable markets. The appropriate allocation depends on the financial plan, investment horizon, income needs, and tolerance for risk.
Seeking a higher return can also involve accepting greater volatility or potential losses. The objective is not necessarily to maximize performance in every market environment, but to maintain an investment strategy consistent with the household’s financial needs.
Preparing for long-term care and healthcare expenses
Healthcare is another important consideration, particularly for people planning to retire before Medicare eligibility. Health insurance premiums, deductibles, and out-of-pocket expenses can represent a substantial portion of retirement spending. The cost depends on age, location, coverage, income, and other circumstances.
Jake Cross emphasizes the importance of evaluating those expenses before retirement rather than waiting until coverage is needed. Long-term care presents another planning challenge. Some households may have sufficient resources to fund potential care expenses themselves. Others may consider insurance to transfer a portion of that financial risk.
The appropriate decision depends on available assets, anticipated care needs, policy terms, premiums, family circumstances, and the potential effect on the financial plan. Medicaid planning may also arise in certain situations, but eligibility requirements, asset-transfer rules, and applicable look-back periods make professional legal guidance particularly important. There is no universal answer that applies to every household.
How AI is changing financial planning
Jake Cross also discusses how artificial intelligence is being incorporated into certain planning workflows. AI tools can help professionals locate and summarize information from sources such as the IRS, potentially reducing the time required for initial research.
However, the information still requires verification. Tax rules, financial regulations, and planning considerations can be complex. AI-generated answers may be incomplete, outdated, or incorrect, even when presented confidently.
Jake Falcon shares an example of encountering incorrect information while researching education savings rules. The lesson is that technology can support research and organization, but it should not replace careful analysis or the application of financial information to an individual’s circumstances.
Tax planning creates additional flexibility
The conversation also highlights the relationship between account structure and future retirement decisions. Traditional retirement accounts, Roth accounts, and taxable brokerage accounts generally have different tax characteristics. Maintaining assets across different account types may provide flexibility when determining how to fund spending in retirement.
For example, the source of a withdrawal can affect taxable income and potentially influence healthcare-related costs or other financial considerations.
Jake Cross explains that tax planning involves evaluating current and anticipated future circumstances rather than assuming the same contribution or withdrawal strategy will remain appropriate indefinitely. The discussion reinforces the importance of coordinating financial planning with qualified tax professionals when evaluating individual tax consequences.
Why regular financial planning meetings matter
A financial plan should not be treated as a document that is completed once and forgotten. Spending changes. Families grow. Healthcare needs evolve. Tax laws change. Investment markets fluctuate, and retirement priorities may look different over time.
Jake Cross encourages clients to meet regularly with their advisors, even when they believe little has changed. These meetings provide opportunities to review assumptions, revisit goals, evaluate investment allocation, and address questions before they become larger concerns.
He also recommends submitting questions ahead of time so the advisor can prepare and make the conversation more productive.
A financial plan should reflect your life
The amount needed for retirement cannot be determined by a single savings target, a friend’s account balance, or a universal withdrawal percentage. It depends on the life someone wants to live, the resources available to support that lifestyle, and the risks that may arise along the way.
A thoughtful financial plan brings those considerations together. Just as importantly, it provides a framework that can be updated as life changes.
The better question may not be whether you have as much money as someone else. It may be whether your financial resources are organized to support your own goals.
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