Planning Examples

The kinds of decisions Keystone is built for.

Four hypothetical composites drawn from common planning situations. They show what coordinated planning can look like when tax, income, and investment decisions stop being handled by different people.

The stories on this page are hypothetical composites drawn from common planning situations. They are not specific clients, are not based on any one client experience, and should not be understood as referencing a real person. Names and financial details are representative only.

Fast-Growing Business Owner

Composite #1

Fast-Growing Business Owner

Age ~40

Marcus came in with a profitable business and almost no personal wealth outside of it. The question wasn't whether the business was working. It was how to translate the business working into a life that didn't depend entirely on the business continuing to work.

What was on the table:

  • Business was profitable, but nearly all personal wealth was tied up in it, with no diversification.
  • No clear framework for deciding how much to reinvest versus pull out for personal financial goals.
  • Tax planning was reactive, handled at year-end instead of built into business decisions.

What we did:

  • Connected business and personal finances: Built a single plan that linked business cash flow decisions to personal wealth-building milestones.
  • Created a reinvestment framework: Set clear thresholds for when to reinvest in the business and when to diversify into personal accounts.
  • Proactive tax strategy: Shifted the work from year-end tax scrambles to quarterly planning aligned with retirement contributions and distribution timing.

By the end of the engagement, decisions about reinvestment, retirement savings, and tax timing were coordinated rather than reactive. That's the kind of decision Keystone is built for.

Business Owner Selling Practice and Approaching Retirement

Composite #2

Business Owner Selling Practice and Approaching Retirement

Age ~60

Linda had a buyer for her practice and a closing date six months out. What she didn't have was a coordinated read on what the sale would do to her tax bill, her retirement income plan, or her estate documents.

What was on the table:

  • Faced a significant tax bill on the sale. Asset versus stock sale structure had not been evaluated.
  • No plan for converting a lump sum into reliable retirement income across a 30-year horizon.
  • Estate documents had not been updated to reflect the post-sale financial picture.

What we did:

  • Pre-sale tax structuring: Evaluated asset versus stock sale tradeoffs and timed the closing around tax impact.
  • Retirement income architecture: Designed a withdrawal sequence across taxable, tax-deferred, and Roth accounts.
  • Estate plan coordination: Worked with her attorney to update beneficiary designations and trust structures.

The sale stopped being a single transaction and became a coordinated transition. Tax, income, and estate decisions were aligned before the closing rather than scrambled together afterward.

Executive Navigating Equity Compensation

Composite #3

Executive Navigating Equity Compensation

Age ~45

James had over 60% of his net worth in one company's stock through a mix of RSUs and options. Nobody owned the whole picture.

What was on the table:

  • Held a concentrated position in employer stock through RSUs and options.
  • No clear plan for when to exercise options or sell vested shares without triggering unnecessary taxes.
  • Investment accounts, equity compensation, and retirement planning were managed separately.

What we did:

  • Diversification roadmap: Built a multi-year plan to reduce concentration risk through timed exercises and sales.
  • Tax-aware execution: Coordinated option exercises with estimated payments, charitable giving, and retirement contributions.
  • Unified strategy: Replaced three separate advice tracks with one coordinated plan.

Diversification happened on a schedule rather than in reaction to the next vesting event. Tax consequences were anticipated rather than discovered in April.

Pre-Retiree Couple Preparing for Retirement

Composite #4

Pre-Retiree Couple Preparing for Retirement

Age ~58

Tom and Ellen came in with retirement accounts at four different firms and a clear sense of anxiety about whether the math actually worked.

What was on the table:

  • Had retirement accounts at four different firms with no unified withdrawal strategy.
  • Had not evaluated Roth conversion opportunities before Social Security and Medicare began.
  • Worried about outliving savings but could not get a clear answer on whether their income plan was sustainable.

What we did:

  • Account consolidation and clarity: Brought scattered accounts into a single view and designed a withdrawal sequence.
  • Pre-retirement Roth strategy: Identified a window for partial Roth conversions before Social Security income began.
  • Sustainable income modeling: Built a retirement income plan stress-tested against market downturns, inflation, and long-term care scenarios.

They went from scattered accounts and vague anxiety to a single coordinated plan with clear answers. More than the numbers, they got confidence that their decisions were working together.

Continue exploring

If one example feels familiar, go deeper there.

Business owners

For owners whose tax, cash flow, retirement, and business decisions are starting to overlap.

Read more

Pre-retirees

For people close enough to retirement that timing, taxes, income, and risk need to be modeled together.

Read more

Equity comp

For executives and professionals making tax-aware decisions around RSUs, options, and concentration.

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If any of these stories sound like the kind of decision you're working through, the next step is a 15-minute Explore Call.

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