Life Events Financial Planning Checklist

Practical next steps for 4 of life's most expensive decisions · decisionscalc.com

Remote Work — Before You Switch
  • Run the DecisionsCalc Remote Work Calculator with your actual numbers
  • Get your employer's written remote work policy (pay, equipment, stipends)
  • Calculate your home office tax deduction eligibility (IRS Form 8829)
  • Assess your dedicated workspace — does it meet the "regular and exclusive use" IRS test?
  • Price out upgraded internet plan (business-grade for reliability)
  • Budget for ergonomic chair, monitor, standing desk within year 1
  • Review state income tax rules if working remotely from a different state
  • Negotiate a remote stipend — $50–150/mo is increasingly standard
Key insight: The average remote worker saves $4,000–10,000/yr. The biggest variables are commute distance and lunch spending — not equipment costs.
Having a Baby — Financial Action Plan
  • Confirm your out-of-pocket maximum on your health plan — delivery bills will hit it
  • Call your insurer to pre-authorize delivery and confirm in-network providers
  • Understand your FMLA eligibility and employer paid leave policy in writing
  • Research your state's paid family leave benefit (12 states + DC have it)
  • Open a Health Savings Account (HSA) if on a HDHP — triple tax benefit
  • Start childcare search/waitlist now (top daycares have 6–12 month waitlists)
  • Get term life insurance quotes — cheapest when young and healthy, critical with a dependent
  • Create Amazon Baby Registry — 15% completion discount on remaining items
  • Claim Child Tax Credit ($2,000/child) and Child Care Tax Credit on your taxes
Key insight: Childcare is typically 40–60% of year-one costs. Research options before birth — the best spots fill up fast and costs vary 3× by type and state.
Chronic Illness — Cost Reduction Checklist
  • Check GoodRx for every prescription — savings of 20–80% are common
  • Ask your doctor about generic alternatives for all brand medications
  • Apply for manufacturer Patient Assistance Programs (PAP) — many drugs are free for qualifying incomes
  • Review your insurance plan at open enrollment — HDHP + HSA can save thousands if healthy
  • Check ACA marketplace subsidies — if income qualifies, switch to a lower-cost plan
  • Get disability insurance quote while still insurable
  • Request FMLA protections from employer for medical leave
  • Document all medical expenses — deductible above 7.5% of AGI on taxes
  • Join condition-specific non-profit for co-pay assistance programs
Key insight: Presenteeism (working while sick at reduced productivity) is often the largest hidden cost — averaging $4,000–8,000/yr. Discuss accommodations with HR.
Aging Parent Care — Planning Checklist
  • Have the money conversation early — know parent's assets, income, and insurance
  • Check if parent has long-term care insurance (many policies go unclaimed)
  • Understand Medicare coverage limits — it does NOT cover ongoing custodial care
  • Check Medicaid eligibility for nursing home coverage (asset/income limits apply)
  • Get POA (Power of Attorney) and healthcare proxy documents in place now
  • Research your state's PACE program (Program of All-Inclusive Care for the Elderly)
  • Get 3 quotes from assisted living/home care facilities in the area
  • Speak to employer about caregiving leave — 59% of employers offer some support
  • Look into respite care to allow you to maintain employment
  • Consult an elder law attorney before spending down assets for Medicaid
Key insight: A Place for Mom's advisor service is free to families and can identify options 20–30% cheaper than searching independently. Use it first.

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Not financial advice. Consult a qualified professional for your situation. See full disclaimer.

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