Does This Sound Like You?

These sample retirement scenarios reflect the kinds of questions we hear every day—from when to retire to how to draw income.
While fictional, each story is rooted in real-life concerns that many of our clients share.

Middle-aged couple in cycling gear sitting by a lake, symbolizing pre-retirement reflection and planning.

Sample Scenario #1: Pre-Retirees Juggling Family Support and Retirement Timing

(Age 50-60s | Still working)

They’ve done a solid job saving—but competing priorities like college tuition, aging parents, and market uncertainty have left them unsure whether early retirement is realistic. They’re looking for clarity on when they can retire and how to coordinate income if one stops working sooner than the other.

Family: Aging parents and two children, both currently in college

Retirement Status: Still working, but ready to set a target retirement date

Current & Future Expected Resources:

  • A $1.5 million investment portfolio, mostly held in Traditional 401(k)s and IRAs

  • A pension (which includes a monthly income option or a lump sum option)

  • Railroad Retirement Board income

  • Social Security income

Top Questions & Concerns:

  • Retirement Timing & Lifestyle:

    • If we retire in the next 5 years, can we maintain our current lifestyle?

    • If our parents need more care, will we still be able to retire on time?

  • Early Retirement Income Strategy:

    • How can we generate income from our investments before age 59 ½?

  • Ongoing Savings Decisions:

    • Should we keep contributing to our Traditional 401(k)s, or consider other account types?

  • Family Support & Tradeoffs

    • How can we help our kids with college costs while still saving enough for ourselves?

Recently retired woman relaxing in a backyard chair, representing peace of mind from retirement income planning.

Sample Scenario #2: Recently Retired and Focused on a Tax-Efficient Paycheck

(Age 60-70s | Just Retired)

After a recent retirement, this individual has done a strong job of accumulating resources and is now focused on feeling confident in their retirement income plan. They’re especially interested in tax-efficient strategies and finding ways to support causes that are meaningful to them.

Family: Multiple siblings, nieces, and nephews

Retirement Status: Recently retired

Current & Future Expected Resources:

  • A $1 million Traditional IRA

  • $100,000 in a taxable brokerage account

  • $20,000 Roth IRA

  • Social Security income (has not yet begun collecting benefits)

Top Questions & Concerns:

  • Social Security Timing

    • When should I begin collecting Social Security benefits?

  • Withdrawal Strategy

    • Which accounts should I begin withdrawing from first?

  • Tax Reduction Opportunities

    • Could Roth conversions help reduce my lifetime tax burden?

  • Charitable Giving Strategy

    • How can I support causes I care about in a way that’s also tax-efficient?

Close-up of elderly couple holding hands in a wheat field, representing long-term partnership and retirement experiences.

(Age 70-80s | Retired for years)

They’ve been retired for over a decade and are comfortable with their current lifestyle. But as they continue to age, they want to feel confident their spouse will be financially secure if something happens to one of them—while also finding ways to create lasting memories with their family.

Family: Grown children and multiple grandchildren currently in school

Retirement Status: Retired for over a decade

Current & Future Expected Resources:

  • A $750,000 investment portfolio spread across Traditional IRAs and non-qualified annuities

  • Pension for the husband (with a 50% survivor income benefit)

  • Social Security income

Top Questions & Concerns:

  • Loss of a Spouse & Income Impact

    • If one of us passes away, will our surviving spouse be financially okay?

    • What income sources would change, and how do we prepare for that?

  • Protecting Long-Term Financial Wellbeing

    • How can we feel confident spending on meaningful family experiences while still protecting our long-term financial stability?

  • Future Planning Considerations

    • Now that our annuities are out of their surrender period, what are our options going forward?

Sample Scenario #3: Retired Couple Seeking Long-Term Financial Security

Professional woman smiling in office setting, symbolizing confidence in handling equity compensation and financial planning.

Sample Scenario #4: Working Executive Navigating Complex Investment Choices

(Age 40-50s | Still working)

She’s worked hard to advance in her career and now enjoys a comfortable income and a growing list of complex benefits. As new investment options become available—like stock options and employer equity—she’s looking for help navigating these choices and building a savings strategy she understands and feels confident in.

Age: 45

Family: Long-term boyfriend

Retirement Status: Still working, with no plans to retire for at least another decade

Current & Future Expected Resources:

  • $1.25 million in a Traditional 401(k)

  • Unvested RSUs (Restricted Stock Units) through her employer

  • Vested and unvested Non-Qualified Stock Options (NSOs)

  • Future Social Security income

Top Questions & Concerns:

  • Equity Compensation Planning

    • How can I develop a clear, coordinated plan for my stock options and equity compensation?

    • I have access to an Employee Stock Purchase Plan (ESPP)—should I participate, and how does it fit into my broader strategy?

  • Tax-Efficient Retirement Savings

    • I make too much to contribute directly to a Roth IRA. What are my options for building tax-free retirement savings?

  • Insurance & Risk Management

    • Do I have an appropriate amount of life insurance in place for both my current needs and long-term goals?

Have similar questions to any of the above examples? Let’s talk through yours.