Short, general answers drawn from the playbook. None of them is advice for your situation.
What should a military retiree review in a civilian compensation package?
More than base salary: bonus terms and payment dates, 401(k) eligibility and match, HSA eligibility, equity vesting, deferred-compensation deadlines, insurance elections, and withholding once salary joins retired pay.
Can I contribute to a civilian 401(k) after contributing to the TSP?
Generally yes, but the IRS employee deferral limit is shared across 401(k), 403(b), and TSP contributions in the same year, so TSP deferrals count toward it. Whether the plan accepts a TSP rollover is a separate question.
How do military retired pay and a civilian salary affect tax withholding?
Each payer generally withholds as if it were your only income, so a year mixing retired pay, salary, bonus, and equity income can end up under-withheld. Check withholding after the first paycheck and first pension payment.
What should I look for in an executive compensation package after military retirement?
Beyond salary and bonus: equity grant type and vesting, deferred-compensation deadlines and employer credit risk, non-compete and severance terms, and benefit eligibility dates. Several may need attorney or tax review.
How should I think about RSUs or employer stock after leaving the military?
RSUs, restricted stock, options, and ESPP shares differ in vesting, tax, liquidity, and concentration. Ask when shares vest, how taxes are withheld, when trading windows open, and how much net worth sits in one stock.
When should I review my civilian benefits after starting a new job?
In three windows: before accepting or starting, for deadline-driven elections; during onboarding, for cash flow, withholding, health plan, and beneficiaries; and in the first quarter, once real payroll data exists.
Educational information only. Not individualized investment, tax, legal, military-benefits, or insurance advice. Limits and rules change; verify with the IRS, your plan documents, and the appropriate federal agency.