Planning Illustrations
Three situations, and what we would look at first.
Three composite illustrations, not actual clients. Each shows the questions coordinated tax, investment and life planning works through, and why the answer depends on the details.
The Tech Founder
$4M net worth · Business Owners
This is a composite. Not an actual client. Illustration only.
Situation
Founder of a B2B software company organized as a Delaware C corporation, with about $4M in net worth and about $800K a year in salary. The company has no retirement plan. Much of the salary falls in the top two federal brackets, with payroll taxes on top.
Challenge
No workplace retirement plan, so years of tax-deferred saving room going unused. Pay set by habit rather than by plan, with no review of how salary, bonus and any dividends are taxed. No quarterly tax planning cadence with CPA.
What We Would Look At
- ✓Whether an S corporation election fits at all. Not every company can elect (no more than 100 shareholders, one class of stock, and limits on who may own shares), and switching from a C corporation can end qualified small business stock treatment under section 1202 and bring a built-in gains tax on later asset sales. For a founder who may sell, those costs can outweigh the payroll tax saved.
- ✓Which retirement plan the business can support. A Solo 401(k) is only for an owner with no employees other than a spouse; with staff on payroll, a standard or safe harbor 401(k) is the comparison. For 2026, total additions to one person's account are capped at $72,000, or 100% of pay if less, before any age-based catch-up.
- ✓A quarterly tax projection with the CPA.
- ✓Moving retirement savings from a single target-date fund to a low-cost mix that fits the household's whole balance sheet.
What the Work Produces
A written recommendation on entity, pay and retirement plan that the CPA can act on, with the trade-offs stated.
The RE Investor
$6M net worth · Real Estate Investors
This is a composite. Not an actual client. Illustration only.
Situation
Real estate investor with residential rental properties across three states. $6M net worth. Still working a W-2 day job at $180K. Self-managing most properties. No formal asset protection strategy.
Challenge
Zero cost segregation studies on any property. A recent sale closed without an exchange, so the whole gain, including tax on past depreciation, was taxed that year. Properties split between LLCs and personal names, with no umbrella policy.
What We Would Look At
- ✓Which properties justify a cost segregation study, starting with the highest-basis ones, and what the extra depreciation is worth in each case.
- ✓A planned 1031 exchange for the next sale, with a fallback if a replacement is not identified within 45 days or closed within 180 days (or the tax return due date, if earlier).
- ✓An attorney licensed where the properties sit to decide the entity structure, including whether a series LLC is recognized in each of the three states, and an umbrella policy.
- ✓Whether real estate professional status is realistic. It requires more than half of all working hours, and more than 750 hours, in real estate the investor materially participates in, and hours worked as an employee count against it. Alongside a full-time job that rarely works for the job-holder alone; on a joint return, a spouse who works in real estate can qualify instead. If the status is not met, at this income the $25,000 rental-loss allowance is fully phased out, so the extra depreciation offsets the portfolio's own rental income and any unused loss carries forward.
What the Work Produces
A property-by-property plan for depreciation, exchanges and entity structure that the CPA and attorney can carry out.
The FIRE Couple
$3.6M net worth · FIRE Followers
This is a composite. Not an actual client. Illustration only.
Situation
Dual-income couple, both 48, combined $340K income. $3.6M net worth: $2M in traditional 401(k)s, $600K taxable brokerage, $400K Roth, $600K in home equity. Target: retire at 52.
Challenge
No withdrawal sequencing plan. $2M in pre-tax accounts with no Roth conversion strategy, so required distributions later could push them into higher brackets. Healthcare costs for 13 years of pre-Medicare coverage completely unmodeled.
What We Would Look At
- ✓A withdrawal order across all account types, stress-tested with Monte Carlo analysis, with every assumption written down: returns, inflation, spending, Social Security timing and how long either of them might live.
- ✓A 10-year Roth conversion ladder of up to $200K a year in the low-income window between retirement and Social Security, sized year by year against tax brackets and the healthcare bridge below.
- ✓Spending part of each year abroad while keeping the primary residence, with the cost difference, visa limits and tax-residency rules checked before any of it goes into the plan.
- ✓The healthcare bridge for the 13 pre-Medicare years: each year's conversion amount weighed against the marketplace premium credits it would cost, so some years convert less and keep the subsidy, with expat insurance as the backup.
What the Work Produces
A month-by-month retirement income plan the household can follow, with the assumptions behind it written down.
Fees follow the published schedule on our pricing page.
These illustrations are hypothetical composites. They are not actual clients and do not describe any client's experience or results. The facts are assumed, and the strategies named may not suit your situation. Tax rules described are federal rules as of 2026 and can change. No outcome is promised or implied. Wealth In Yourself is a state-registered investment adviser; registration does not imply a certain level of skill or training. This page is not personalized investment, tax or legal advice. Consult qualified professionals about your situation.
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