Model the runway, coverage, equity deadlines, investments, and tax considerations around the break you want to take.
What does the planned time away require each month?
Which benefits and coverage need a replacement?
Which equity or account decisions have deadlines around the departure?
How could income changes and portfolio withdrawals affect the tax picture?
The modeling is built from assumptions, plan documents, and the choices available to you. It is a planning framework, not a promise about how long assets will last.
Build a working view of the break, including expenses, coverage, priorities, decision dates, and possible return to work.
Review eligible assets and liquidity needs in the context of the planned break, market risk, and longer term goals.
Consider how lower earned income, equity activity, portfolio transactions, and possible conversions may interact.
Review what changes on the departure date and which choices remain available afterward under the governing documents.
Scope note: Projections depend on assumptions and do not guarantee how long assets will last. Benefits remain subject to plan documents and separation terms. Jake does not prepare tax returns or draft legal documents.
Bring the timing, the reason, and whatever numbers you already have. The first conversation can start before every detail is settled.
Thirty minutes on Microsoft Teams. No obligation. Availability and services depend on registration, engagement scope, and firm approval.