Direct Answer
Investment guides for special life scenarios: late starts, windfalls, divorce, disability, military service, self-employment, expat status, early retirement.
Special Investment Scenarios: Life Events and Non-Standard Situations
Not every investor follows the standard accumulation path. These guides cover investing decisions shaped by specific life circumstances, career types, financial events, and legal or tax situations that require different approaches than general advice assumes.
Getting Started Late
Financial Events and Windfalls
- Windfall: inheritance, lottery, settlement, and large bonus
- Inheriting an IRA: step-up basis, estate tax, and inherited account rules
- Concentrated position: RSUs, stock options, and single-stock risk reduction
Life Transitions
- Divorce: dividing investment accounts and rebuilding a portfolio
- Widowed: surviving spouse accounts, beneficiary IRA rules, and rebuilding
- Remarriage: blending finances, existing retirement accounts, and prenup considerations
- Career break: parental leave, illness, and caregiving investing gaps
- Caregiver: spousal IRA, career interruption, and sandwich generation finances
Employment and Income Type
- Self-employed: SEP-IRA, Solo 401(k), and irregular income investing
- Gig worker: side hustle income, estimated taxes, and Roth vs. traditional
- Entrepreneur: business owner retirement plans, exit planning, and liquidity events
- Teacher: 403(b), pension, TRS, TDA, and 457(b) stacking strategies
- Healthcare worker: high student debt, late career start, and HSA maximization
- Nonprofit worker: 403(b), 457(b), and PSLF interaction with investing
- Government employee: FERS, TSP, and pension plus investing coordination
- Military: TSP, SBP, VA benefits, and deployment savings strategies
Special Circumstances
- Disability: investing with disability income or ABLE accounts
- Immigrant: cross-border investing, foreign income, and dual citizenship considerations
- Expat: investing from abroad, FEIE, PFIC rules, and foreign account reporting
- Student debt: invest vs. pay down loans, income-driven repayment, and investing
Income Level Strategies
- Low income: Saver's Credit, ABLE, and investing on a tight budget
- High income: backdoor Roth, mega backdoor, NIIT, and deferred compensation
- Debt-heavy: high-interest debt vs. investing tradeoffs
Retirement Timing and Drawdown
- Early retirement: FIRE movement, Rule of 55, 72(t) distributions, and ACA bridge
- Semi-retirement: part-time work, drawdown, and earned income plus Social Security
Asset Concentration
References
The rules and figures stated on this page come from these primary sources. Tax and benefit rules change, so confirm current amounts with the source before acting.