Checklist #45 · Life Events
Job Change Financial
Evaluate the full financial picture of a job change — benefits, retirement accounts, compensation comparison, and transition costs — before you sign.
19 action items~20 min to complete4 sections
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Total Compensation Comparison
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Calculate total annual value of current comp: base + bonus + equity + benefits valueKey
Calculate total annual value of new offer using the same frameworkAction
Value unvested equity at current employer — what are you forfeiting?Watch out
Negotiate a sign-on bonus to compensate for unvested equity forfeitedAction
Confirm start date allows for proper equity vesting if a cliff is approachingKey
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Benefits Comparison',
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Compare health insurance plans — deductibles, network, and premium differencesKey
Confirm 401(k) match percentage and vesting schedule at new employerWatch out
Understand the PTO policy — days, accrual rate, and whether unused PTO is paid out at separation
Check dental, vision, life, and disability insurance coverage differences
Assess any loss of perks: parking, gym, meals, professional development budget
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Transition Planning',
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Roll over your old 401(k) to a rollover IRA or new employer's 401(k) within 60 daysKey
Understand COBRA coverage options and cost for the period between health plansWatch out
Determine whether there's a waiting period before new benefits begin at the new jobKey
Plan for any income gap if there's time between jobs
Understand any non-compete or non-solicitation clauses in your current employment contractWatch out
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Tax & Legal Considerations
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Check whether any current employer benefits have clawback provisionsWatch out
Adjust W-4 withholding for any anticipated income changes
If changing states, understand the multi-state tax filing implicationsAction
Update your professional credentials, licenses, or certifications for the new role if needed