WF-36 · Workflow · 3 Tools · Career Transition & Mobility

Job Separation Financial Playbook

Three decisions that must happen in the right order when you lose or leave a job: coverage (COBRA vs. marketplace), cash flow (severance vs. UI sequencing), and equity (option exercise before the window closes). Each has a hard deadline. This workflow addresses them in priority order.

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Step 1 · AL-141 · COBRA vs. ACA Coverage Optimizer
Find Your Cheapest Health Coverage Path
Key InputsCOBRA monthly premium, household size, expected AGI for the coverage year, state (for Medicaid thresholds), HSA eligibility.

Do this on Day 1 — you have 60 days from the qualifying event to elect COBRA and 60 days to enroll in marketplace coverage. They don't overlap cleanly. The tool models COBRA full-premium cost against ACA marketplace net premiums using the 2026 §36B baseline PTC table (enhanced subsidies expired 12/31/2025; the 400% FPL cliff is restored). At 3.5× FPL your subsidy cliff warning fires; at 4.0× you're fully on your own. The break-even AGI loop finds the exact income level where marketplace becomes cheaper than COBRA. Export the recommendation to carry into tax planning.

Open COBRA vs. ACA Coverage Optimizer →
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Step 2 · AL-143 · Severance + UI Timing Sequencer
Sequence Severance to Maximize Unemployment Benefits
Key InputsSeverance total and form (lump sum vs. salary continuation), weekly salary, state UI benefit estimate, state UI bucket (no-delay / standard / generous).

Most people don't realize that the form of severance — lump sum vs. salary continuation — can shift your UI eligibility by weeks. In "standard" states (most of the US), continuation pay delays UI by the equivalent number of weeks; lump sum typically doesn't. This tool shows the optimal filing path, quantifies benefits at risk if you file suboptimally, and produces a week-by-week timeline. The output explicitly labels the path as "verify with your state UI agency before filing" because state rules vary even within the buckets.

Open Severance + UI Timing Sequencer →
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Step 3 · AL-142 · Option Exercise Window Analyzer
Model Option Exercise Before Your Window Closes
Key InputsVested shares, strike price, current FMV, option type (ISO/NSO), window days (typically 90), available cash, exit scenario probability sliders.

After separation, your options convert from an indefinite right to a ticking clock — usually 90 days. After that, ISOs convert to NSOs (losing favorable AMT treatment) and some plans require exercise or forfeiture. This tool calculates cost to exercise, expected value across three exit scenarios weighted by probability, maximum shares affordable given your cash, and the AMT flag for ISOs with spreads above $50K. If the EV is negative or cash is insufficient, it says so plainly and links to the ISO AMT modeler (AL-116) for deeper AMT modeling.

Open Option Exercise Window Analyzer →