Financial Planning Case Studies
These cases are a collection of example situations and services that we see and provide every day.
Ascent
High-Income Household
The Good Problem With No Defaults: A Savings Hierarchy for the Naidus
A physician household with maxed accounts needed a savings hierarchy, a home purchase analysis, and an independent review of a permanent life insurance proposal.
Current State of Finances
Priya Naidu, 36, is an anesthesiologist four years out of residency; her husband Dev is a software engineer. Household income is about $710,000, the retirement accounts are maxed, the backdoor Roths happen every January, and a taxable brokerage account is accumulating cash faster than they’re deciding what to do with it. Everything is going right, which is precisely the problem: past the obvious moves, there are no defaults.
The open decisions have stacked up. A $1.2 million home purchase, now or after Priya’s partnership decision in two years. Education funding for two children under five. And a “physician financial specialist” has been persistent about a permanent life insurance policy that sounds airtight and feels off. They don’t want to hand their finances over. They want to know if they’re missing something.
The Preflight Check: What are we thinking about?
Ordering the next dollar
With the standard accounts maximized, we build the savings hierarchy: the priority order for every surplus dollar across additional tax-advantaged space, the taxable account, education funding, and cash reserves, with the reasoning documented so the order survives busy months.
Making the house a number, not a mood
We model the purchase at both timelines, now versus post-partnership, against their plan: down payment sourcing, carrying costs at current rates, and the effect on every other goal. The output is a price range the plan supports, not a feeling about what they can afford.
Reviewing the policy independently
The permanent life insurance illustration gets taken apart line by line: the internal costs, the projected versus guaranteed values, and the comparison against term coverage plus investing the difference. Because we sell nothing and earn nothing from the outcome, the analysis has no side.
Right-sizing education funding
We size 529 contributions against realistic college cost projections and the competing goals, funding education deliberately rather than reflexively.
Ascent
Building the Structure
High Income, Late Start: Building the Structure for the Brandts
A newly minted partner household with lumpy income needed cash flow plumbing, a deferred compensation decision, and a work-optional target instead of a retirement date.
Current State of Finances
Tom Brandt, 44, made partner at his consulting firm two years ago; his wife Elena, 42, returned to full-time work as a nurse practitioner once their youngest started school. Household income just crossed $500,000, dramatically higher than five years ago, but the balance sheet hasn’t caught up: about $900,000 saved, uneven retirement contributions from the lean years, a mortgage, and a vague sense that people earning what they earn should be further along.
They are not behind in any way that matters, but they are unstructured. Partner distributions arrive quarterly and get absorbed. Tom’s firm offers a deferred compensation plan he doesn’t fully understand. And they may never want to retire in the traditional sense, both like their work, which makes every standard retirement calculator feel beside the point.
The Preflight Check: What are we thinking about?
Building around lumpy income
Quarterly distributions require different plumbing than a salary. We design the cash flow structure: what happens automatically when a distribution lands, in what order, so saving stops depending on quarterly willpower.
Evaluating the deferred compensation plan
Nonqualified deferral is a real opportunity and a real risk, tax deferral against creditor exposure and distribution inflexibility. We model participation levels against the Brandts’ brackets and the firm’s stability rather than treating the enrollment form as a yes-or-no question.
Planning for work-optional, not retired
Since neither Brandt wants a hard stop, we model financial independence as a threshold rather than a date: the asset level at which continuing to work becomes fully a choice. That reframing changes the savings targets and the investment horizon.
Catching up deliberately
The plan sequences the catch-up: maximizing the qualified space available to each of them, deploying the accumulated cash on a schedule rather than all at once, and documenting the order so progress continues through their busiest years.
Ascent
Equity Compensation
Equity Comp Arrives: RSU Strategy for Maya Lindqvist
An engineer whose compensation stopped looking like a salary needed a standing vest policy, corrected tax withholding, and a plan for the growing single-stock position.
Current State of Finances
Maya Lindqvist, 39, left a stable engineering role for a growth-stage software company eighteen months ago, and the equity she took in the trade has started vesting. Her salary is $340,000; with RSU vests, her total compensation last year exceeded $520,000, and her company stock position, about $450,000 and growing with each quarterly vest, is now her largest holding outside her 401(k). Total portfolio: roughly $1.4 million.
Maya’s questions are the ones equity compensation always generates and rarely answers: sell the vests immediately or hold? What did the vesting actually do to her taxes, and why was her refund so wrong last year? And underneath those, a structural one, her financial life was built for a salary, and her compensation no longer looks like one.
The Preflight Check: What are we thinking about?
Setting the vest policy
The central decision is a standing rule for each vest, sell, hold, or a documented ratio, made once and deliberately, rather than quarterly by mood. We model the concentration trajectory if she holds by default: at her vesting schedule, the position compounds into exactly the problem our Glide clients spend years unwinding.
Fixing the tax plumbing
RSU withholding rates routinely fall short of actual marginal rates at her income, which explains the April surprise. We map the real liability, the estimated payment schedule that prevents penalties, and the interaction with her other income.
Rebuilding the savings structure around variable compensation
Like a salary, but lumpier: we set the order of operations for each vest’s proceeds, tax reserve, then the priority ladder across her accounts, so the windfall quarters build the plan instead of drifting.
Stress-testing the single-name risk now
At $450,000 the position is manageable; the point of modeling a sharp decline today is deciding the policy while the stakes are moderate, not after the position has doubled twice.
Glide
Retirement Transition
Two Years Out: Retirement Timing and Income Design for the Calverts
A couple two years from their target date needed timing, withdrawal sequencing, Roth conversions, and spending capacity quantified before giving notice.
Current State of Finances
David and Susan Calvert, 61 and 59, have done nearly everything themselves. David spent three decades in pharmaceutical operations; Susan teaches at a community college with a modest pension. Between his 401(k), their IRAs, and a taxable account they built through steady saving, their portfolio totals $4.2 million, and David has managed every dollar of it. Their house is paid off. Their spreadsheet says they can retire. David no longer fully trusts the spreadsheet.
The questions have stopped being about accumulation and started being about sequence. Retire in 2027 or 2028? Which pension election, single life or survivor, and how does that interact with Social Security timing for each of them? When do Roth conversions stop making sense once Medicare premiums enter the picture? And the question Susan actually asked first: after forty years of saving, are we allowed to spend it?
The Preflight Check: What are we thinking about?
Testing both retirement dates
Rather than debating 2027 versus 2028 in the abstract, we model both against sequence-of-returns risk: what each date looks like if the market falls sharply in the first years of retirement. The comparison turns a stressful open question into a quantified tradeoff with a defensible answer.
Sequencing withdrawals and conversions together
The Calverts’ savings sit mostly in tax-deferred accounts, which means required minimum distributions will eventually force income they don’t need. We map a year-by-year withdrawal order and a multi-year Roth conversion schedule, sized to fill lower tax brackets in the early retirement years while watching the IRMAA thresholds that would raise their Medicare premiums.
Pension and Social Security elections as one decision
David’s pension options and both spouses’ Social Security claiming ages are usually presented as separate choices. They aren’t. We model the combinations against survivor needs and longevity assumptions so the elections work as one coordinated income floor.
Quantifying spending capacity
The plan concludes with a number: what the Calverts can spend annually, including the travel budget Susan has been quietly deferring, with the modeling behind it documented so the number can be revisited as markets and circumstances change.
Glide
Concentrated Position
Sixty Percent in One Stock: A Tax-Aware Diversification Plan for Marcus Osei
A twenty-year employee approaching financial independence needed a sequenced diversification strategy with the tax consequences modeled in advance.
Current State of Finances
Marcus Osei, 54, has spent twenty-two years at the same publicly traded industrial company, and his loyalty shows on his balance sheet. Of his $5.8 million portfolio, roughly $3.5 million sits in employer stock, most of it inside his 401(k), with a cost basis under 15% of its current value. Every year he told himself he would diversify; every year the stock rose and the tax bill looked worse.
Now “financial independence at 57” has moved from daydream to spreadsheet. Marcus wants to know two things: whether he can actually leave, and how to unwind a position he knows is too large without handing back a decade of gains in taxes. He has never seen the scenario he actually fears, the stock cut in half the year he retires, modeled on paper.
The Preflight Check: What are we thinking about?
Showing the risk before solving it
We stress-test his plan against a significant decline in the single position. Seeing how far a 50% drawdown moves his independence date reframes diversification from a chore into the central decision of the plan.
Comparing the exit routes on the numbers
Diversifying inside the 401(k) is simple but converts every future dollar to ordinary income. A rollover defers the problem. Net unrealized appreciation treatment, moving employer shares to a taxable account, paying ordinary rates only on the low cost basis, and capital gains rates on the appreciation, may fit his situation unusually well given his basis. We model all three paths side by side, in dollars, across his expected retirement.
Sequencing the sales
Whichever route is selected, the unwind happens on a multi-year calendar built around tax brackets rather than market feelings, with each year’s planned sales documented in advance.
Anchoring the independence date
The plan ties his exit timing to conditions rather than a guess: the portfolio level, the diversification progress, and the spending plan that has to hold for thirty-plus years after the badge gets turned in.
Glide
Retirement Restructuring
Already Retired, Newly Self-Directed: Restructuring in Retirement for Joan Whitfield
A retiree leaving an assets-under-management relationship needed an orderly transition, an RMD strategy, and a portfolio she could run herself.
Current State of Finances
Joan Whitfield, 68, retired three years ago from a hospital administration career with $3.1 million, a paid-off home, and an advisory relationship charging her roughly $28,000 a year against assets under management. She recently concluded she no longer knows what she’s paying for. Joan is organized, numerate, and increasingly hands-on; what she wants is not someone to hold the accounts, but someone to check her thinking as she takes them over.
Her open questions have accumulated: required minimum distributions begin in five years and her tax-deferred balance is large; she claimed nothing yet on Social Security and isn’t sure whether to keep waiting; and her children keep asking whether she has “done anything about the estate stuff.” She hasn’t.
The Preflight Check: What are we thinking about?
Making the transition orderly
Leaving an assets-under-management relationship involves more than a transfer form: cost basis records, holdings that don’t travel cleanly, and positions chosen for someone else’s model portfolio. We inventory what she owns, flag what to keep and what to unwind, and sequence the exit so nothing triggers avoidable taxes.
Defusing the RMD problem early
Joan’s window between now and required distributions is exactly when Roth conversions do their best work. We size a five-year conversion schedule against her brackets and Medicare thresholds, coordinated with her Social Security timing rather than decided separately.
Building a portfolio she can run
The plan specifies an allocation Joan can maintain herself, simple enough to rebalance annually, with the reasoning for each holding documented, and identifies the handful of moments each year that actually require decisions.
Putting the estate questions in order
We coordinate with her attorney on beneficiary designations, account titling, and the documents her children were right to ask about, so the structure matches her intentions rather than her account history.