Financial Planning Questions, Answered

Oswego Legacy Partners works with entrepreneurs, executives, professionals, and multigenerational families—often people transitioning from building wealth to using it to support retirement, family, and legacy objectives. Many of our clients have between $1 million and $20 million or more in investable assets, although complexity and fit are more important than a particular account balance. We frequently help clients coordinate employer benefits, equity compensation, concentrated stock, retirement income, taxes, insurance, estate planning, and significant life transitions. Our objective is to organize complexity into clarity so each financial decision supports the larger purpose of the family’s wealth.

Yes. Oswego Legacy Partners has developed specialized planning resources for Nike and Intel employees and for professionals working within Portland-area healthcare organizations, including Providence, OHSU, and Kaiser Permanente Northwest. These employer relationships can involve combinations of equity awards, retirement plans, pensions, deferred compensation, retiree healthcare, and employer-specific deadlines. We begin by identifying the employee’s actual plans, grants, service history, and governing documents rather than relying on a generic description of the employer’s benefits. Nike, Intel, Providence, OHSU, Kaiser Permanente, and their affiliated organizations are not affiliated with or endorsed by Oswego Legacy Partners or Prudential.

The first conversation is simply a conversation. We listen to what is happening in your life, identify the decisions creating the greatest uncertainty, and explain how we would approach them. You do not need to organize every document or know exactly what type of planning you need before contacting us. There is no cost, no pressure, and no obligation to move forward. If we believe we can help, we will outline the information needed, the planning process, and the next steps. If another professional or resource would be more appropriate, we will be straightforward about that as well.

Compensation depends on the services and financial solutions involved. Securities and investment advisory services are provided through LPL Enterprise, and insurance services may involve compensation from the applicable insurance company. Depending on the relationship, compensation may include advisory fees, securities-related compensation, insurance commissions, or other compensation described in the applicable client agreements and disclosures. Before any engagement begins, we explain how the relationship would work, how the financial professionals and affiliated firms may be compensated, and any material conflicts that should be understood. The initial conversation is provided without cost or obligation.

Oswego Legacy Partners is located at 4550 Kruse Way in Lake Oswego, Oregon. We serve individuals and families throughout Lake Oswego, the greater Portland area, and other locations where our financial professionals are appropriately licensed and able to conduct business. Meetings may be held in person, by phone, or through secure video conferencing. Many employer-benefit and retirement-planning engagements combine virtual meetings with secure document sharing, which allows spouses, family members, and other professional advisors to participate even when they are in different locations.

We begin with one household balance sheet, one income and tax timeline, and one set of family priorities. Employer plans, investment accounts, equity awards, insurance, estate documents, and tax decisions are then evaluated as parts of the same financial life rather than as separate products. A recommendation involving stock compensation, for example, may affect taxes, portfolio risk, charitable giving, retirement timing, and estate planning simultaneously. When appropriate, we coordinate with the client’s tax professional, estate-planning attorney, and other advisors. Oswego Legacy Partners does not replace the legal or tax professionals responsible for providing advice within their respective disciplines.

The outcome depends on the official separation date, how Nike classifies the departure, and the documents governing each benefit and equity grant. Before access changes, download pay records, benefit elections, equity agreements, vesting schedules, ESPP records, deferred-compensation elections, and the complete Fidelity 401(k) statement. Confirm final payroll, healthcare and insurance end dates, severance terms, vesting and option-exercise deadlines, deferred-compensation payments, and any outstanding 401(k) loan. If the 401(k) contains appreciated Nike shares, complete an NUA analysis before selling the shares or rolling the account to an IRA. Preserve every available option until the irreversible decisions have been evaluated. Current Nike plan documents, award agreements, and participant records control.

RSUs and stock options should be treated as different forms of compensation. When an RSU vests and settles, the value of the shares delivered is generally wage income, even if some shares are withheld or sold for taxes. Keeping the remaining shares is then a separate decision about owning Nike stock. A stock option normally creates the right—but not the obligation—to purchase shares at the exercise price. A typical nonstatutory option generally creates wage income when exercised, based on the difference between the market price and exercise price. Options can expire or become worthless, while RSUs generally retain value as long as Nike stock has value. Retirement and separation treatment can also differ significantly by grant, so each award agreement must be reviewed separately.

Nike’s ESPP can provide meaningful value through its 15% discount and lookback feature, but the purchase benefit does not automatically make the shares an appropriate long-term investment. Nike’s public plan materials describe six-month offering periods ending March 31 and September 30, with shares purchased at 85% of the lower applicable offering-date or purchase-date value. Employees should establish a policy before each purchase: sell promptly, retain a defined portion, or hold specific tax lots for a documented reason. Keep every Form 3922 and transaction record because brokerage cost basis may not reflect ESPP compensation income correctly. Also measure ESPP shares alongside RSUs, options, 401(k) stock, future awards, and career income. Current plan terms and tax records control.

Begin by contributing enough through pre-tax and/or Roth deferrals to capture the available Nike match, which current public filings describe as 100% of the first 5% of eligible pay contributed. Pre-tax contributions may reduce current taxable income, while Roth contributions use after-tax dollars and may create tax-free qualified retirement income. Nike also permits a separate non-Roth after-tax contribution of up to 3% of eligible compensation under current public materials. That after-tax source is not Roth money by itself; its value may depend on whether an in-plan Roth conversion feature is available, activated, and working as expected. The appropriate mix should reflect current taxes, future income, liquidity, deferred compensation, and the household’s existing tax diversification. Current Nike and Fidelity materials control.

Net unrealized appreciation, or NUA, may deserve consideration when Nike shares inside the qualified retirement plan have appreciated significantly above the plan’s cost basis. A properly structured transaction can move actual Nike shares in kind to a taxable account, with the plan cost basis generally taxed as ordinary income and qualifying appreciation generally taxed as long-term capital gain when the shares are sold. The strategy normally requires a qualifying event, distribution of the entire balance from qualifying plans of the same type within one tax year, and delivery of actual employer shares. NUA is not automatically better than an IRA rollover, and it is not a recommendation to continue holding Nike stock. Cost basis, taxes, concentration, liquidity, estate objectives, Fidelity procedures, and Form 1099-R reporting must be verified before any sale or rollover.

Nike salary and PSP deferrals are separate elections and can use different deferral percentages. An election made in 2026 applies to salary earned in calendar year 2027, while the PSP election made in 2026 applies to the performance year ending in fiscal 2028. The PSP choice therefore reaches approximately two calendar years into the future. Income tax is generally postponed until distribution, but Social Security and Medicare tax are usually applied when the compensation is earned, vested, or otherwise taken into account under the special FICA rules. Once properly taxed for FICA, the amount generally is not taxed again for FICA when distributed, and attributable growth generally avoids Social Security and Medicare tax. Each election also determines future payment timing, liquidity, and exposure to Nike as an unsecured creditor.

A Nike retirement date should be tested grant by grant rather than against one general retirement rule. Publicly disclosed award terms identify age 55 with five full years of service as an important threshold, but treatment can also depend on the grant date, first grant anniversary, separation classification, and whether the award was granted before or after the September 1, 2024 annual grant. Certain current RSUs may receive prorated vesting, while older stock awards may have no retirement treatment. Certain options may continue vesting, accelerate, or receive an extended exercise period—even though options carry greater investment risk. Compare the proposed date with the next vest, grant anniversary, age-60 milestone for applicable older options, PSP period, deferred-compensation schedule, healthcare transition, 401(k), NUA, and tax year. Each written award agreement controls.

The result depends on whether the departure is voluntary, involuntary, or classified as a qualifying retirement. Before access changes, preserve pay and bonus records, every equity agreement, ESPP statements, SERPLUS elections, Fidelity records, pension information, and retiree-medical documents. Intel’s public materials state that unvested RSUs are generally cancelled on the last day worked, while certain stock-option or other award treatment may improve when grant-specific retirement criteria are met. Bonus eligibility can depend on remaining on payroll through the applicable performance-period end date, and leaving before an ESPP subscription period ends generally produces a refund rather than a stock purchase. Review healthcare deadlines, SERPLUS payments, 401(k) sources, loans, Intel Stock Fund basis, and potential NUA treatment before initiating transactions. Current Intel documents control.

First identify the actual award: a service-based RSU, a PSU, a stock option, or a special retention or new-hire award. An RSU generally creates wage income when vested shares are delivered. A PSU adds another variable because the number of shares earned depends on the applicable performance formula and service requirements; publicly disclosed Intel programs have allowed outcomes ranging from 0% to 200% of target, although metrics and terms vary by grant year. Model the number of units that could settle separately from Intel’s future stock price. Then evaluate withholding, portfolio concentration, trading restrictions, and the amount of Intel exposure already present through ESPP, the 401(k), future awards, SERPLUS, and career income. Vesting determines what is earned; retaining the settled shares is a new investment decision.

Intel’s current public materials describe purchases at 85% of the purchase-date market value for subscription periods beginning on or after February 20, 2025, without the earlier beginning-date lookback. Employees should confirm the formula applicable to their own subscription period. A qualifying Section 423 purchase generally does not create federal taxable income when shares are purchased; tax consequences normally arise when the shares are sold or otherwise disposed of. Holding for the statutory periods may improve the character of part of the income, but it also increases market and concentration risk. Preserve Forms 3922, W-2s, purchase confirmations, and sale records because brokerage basis may require adjustment. If employment ends before the subscription period closes, Intel’s public departure guidance generally describes a refund of contributions without a stock purchase.

These are different tools and should not be treated as one election. Begin with enough pre-tax and/or Roth 401(k) contributions to capture the available Intel match, which current public filings describe as dollar-for-dollar on eligible deferrals up to 5% of eligible compensation, plus an annual true-up. Pre-tax contributions provide current tax deferral; Roth contributions may provide future tax-free qualified income. Voluntary after-tax contributions can create an additional Roth-conversion pathway, but they are not Roth until converted and the current Fidelity process must be confirmed. SERPLUS is a separate nonqualified plan that can defer eligible salary and bonus and may provide a make-up match. It is not a 401(k), cannot be rolled to an IRA, and remains an unsecured obligation of Intel. Liquidity, taxes, payout elections, and Intel credit exposure must be evaluated together.

NUA may be relevant when qualifying Intel Stock Fund shares inside the 401(k) have a low plan cost basis relative to their current value. A properly structured NUA transaction generally moves actual Intel shares in kind to a taxable brokerage account. The plan cost basis is generally taxable as ordinary income in the distribution year, while qualifying appreciation is generally deferred until sale and then treated as long-term capital gain. The strategy normally requires a qualifying event and distribution of the participant’s entire applicable plan balance within one tax year. A partial distribution, annuity election, sale inside the plan, or poorly sequenced rollover may change the outcome. Compare NUA with a direct IRA rollover after considering taxes, liquidity, diversification, estate objectives, Intel concentration, Fidelity procedures, and Form 1099-R box 6 reporting.

There is no universal percentage that is appropriate for every Intel employee. Begin by aggregating Intel shares held in taxable accounts, ESPP accounts, vested-award shares, and the 401(k). Track options, unvested awards, and future purchases separately because they can rebuild concentration after a sale. Then consider salary, bonus, future grants, and SERPLUS as additional forms of dependence on Intel. The position becomes too large when a company-specific decline could materially impair retirement timing, required spending, liquidity, or another important goal—particularly if employment income could be affected at the same time. A written stock policy can establish a target, an action ceiling, and rules for new awards. Transactions must also comply with Intel’s current trading windows, preclearance requirements, material-nonpublic-information restrictions, and any applicable 10b5-1 procedures.

IRMP and SERMA are related but separate benefits. Under Intel’s 2026 retiree-medical materials, IRMP eligibility may be available at age 55 with at least 15 years of eligible service, at age 65 without a minimum-service requirement, or under the Rule of 75. SERMA has additional requirements, including applicable hire or rehire dates, and is a finite premium-reimbursement account rather than medical coverage or cash. Build a calendar showing the end of active coverage, IRMP, COBRA, a spouse’s plan, Marketplace coverage, Medicare Parts A and B, and the date HSA contributions must stop. Model how long SERMA may last and coordinate reimbursement deadlines, eligible dependents, IRMAA, and potential SSA-44 relief after retirement. Eligibility, premiums, deadlines, and coverage options can change, so current Intel and Medicare records control.

Work becomes optional when dependable income, investments, benefits, and available reserves can support the household’s spending, taxes, healthcare, and important goals under both expected and adverse conditions. We recommend comparing at least three dates: the earliest practical retirement date, the next meaningful employer or age-based milestone, and a later comparison date. For each date, measure compensation, equity vesting, retirement benefits, healthcare, taxes, debt, portfolio withdrawals, Social Security, and required liquidity. Then add the nonfinancial considerations—health, family time, caregiving, purpose, flexibility, and the personal cost of continuing to work. The strongest retirement date is not necessarily the date producing the largest gross benefit; it is the date that best supports the family’s lifetime plan after taxes, risk, and life priorities are considered.

Begin by mapping income year by year rather than treating retirement as one tax event. Include salary, bonuses, equity vesting, option exercises, deferred-compensation and SERPLUS payments, pensions, Social Security, investment gains, charitable gifts, and future required distributions. This timeline can reveal years when pre-tax contributions are especially valuable and later years when Roth conversions or capital-gain realization may be more attractive. Also evaluate Medicare IRMAA, Social Security taxation, net investment income tax, estimated-payment requirements, and state residency. Payroll withholding from a bonus or equity award may not equal the household’s final tax liability, so withholding and estimated payments should be reconciled throughout the year. Tax diversification creates choices; it does not require predicting future tax law perfectly.

Yes. A direct contribution of publicly traded shares held for more than one year to a qualified public charity or donor-advised fund may allow the donor to avoid realizing capital gain on the donated appreciation and may support a charitable deduction based on fair market value, subject to itemization, adjusted-gross-income limitations, substantiation, and other tax rules. The shares should generally be transferred directly rather than sold first. Tax-lot selection matters because different lots can have substantially different basis and holding periods. An ESPP gift requires additional care: the gift is a disposition, and the ESPP discount may still create ordinary income even when the donor receives no sale proceeds. Coordinate the transfer with the receiving organization, custodian, and tax professional before initiating it.

Financial planning determines whether the family’s resources can support its lifetime goals. Estate planning creates the legal documents and structures governing incapacity, asset transfer, guardianship, and decision-making. Legacy planning addresses the purpose behind those arrangements: what the wealth is intended to protect, encourage, teach, and make possible for others. Oswego Legacy Partners’ Legacy Trilogy approaches this through three connected ideas. The Legacy Foundation identifies the values, relationships, and responsibilities beneath the wealth. The Legacy Blueprint organizes the people, structures, and decisions required to carry those intentions forward. The Legacy Practice turns the plan into an ongoing process of communication, preparation, and adaptation. Estate documents remain essential, but documents alone cannot prepare a family to live with the responsibilities they create.

Healthcare professionals often have multiple retirement programs, highly variable compensation, pension decisions, deferred compensation, student-loan considerations, and employer-specific retiree-health rules. At Providence, the legal employer, represented status, and governing agreement can change 401(k), 457(b), pension, and student-debt-match benefits. At OHSU, an election between the University Pension Plan and Oregon PERS can be one of the most consequential decisions, while clinicians, house officers, and other employee groups may have separate programs. At Kaiser Permanente Northwest, the legal employer and professional group can determine pension, savings-plan, retiree-medical, incentive, and private-shareholdership rights. The first planning step is therefore to identify the exact W-2 employer, employee group, hire date, service history, and controlling plan documents before applying any general benefit description.