Taxes Articles
Practical explainers and guidance for taxes decisions.
RSS feedInvesting
What Is an IPO Lockup Period and How Does It Affect Employees?
An IPO lockup period can prevent employees, founders, and other insiders from selling shares immediately after a company goes public. Learn how lockups, blackout windows, trading policies, taxes, and concentration risk can affect equity compensation.
Health Insurance
What Happens to Your HSA, FSA, and Benefits When You Leave a Job?
When you leave a job, some benefits follow you and others run on deadlines. Review what happens to your HSA, FSA, dependent-care FSA, commuter benefits, wellness incentives, reimbursements, final claims, and employer benefit accounts before access closes.
Retirement
Should You Roll Over Your 401(k) or Leave It Where It Is?
A 401(k) rollover is not automatic housekeeping. Before moving old workplace retirement money, compare the old plan, a new employer plan, an IRA, fees, investment choices, Roth treatment, creditor protection, early-access rules, and tax risks.
Retirement
How to Build a Tax-Smart Retirement Withdrawal Plan
A tax-smart retirement withdrawal plan coordinates taxable accounts, traditional retirement accounts, Roth money, Social Security, RMDs, Medicare premiums, and cash reserves so income is funded deliberately instead of one withdrawal at a time.
Retirement
How to Build a Retirement Income Plan
A retirement income plan turns Social Security, pensions, savings, cash reserves, portfolio withdrawals, taxes, and possible annuity income into a paycheck that can adapt as markets, healthcare costs, and household needs change.
Retirement
Which Accounts Should You Tap First If You Retire Early?
Early retirement changes the usual withdrawal-order question. Before age 59 1/2, the best account to tap first depends on cash reserves, taxable accounts, Roth contribution access, 401(k) rules, the Rule of 55, 72(t), health insurance, taxes, and how long the bridge years need to last.
Retirement
What Is a 72(t) Distribution?
A 72(t) distribution uses substantially equal periodic payments to access certain retirement accounts before age 59 1/2 without the 10% early distribution tax. It can help bridge early retirement income, but the rules are rigid and mistakes can create retroactive tax consequences.
Retirement
What Is an In-Service Withdrawal From a 401(k)?
An in-service withdrawal lets a still-employed worker take money from a 401(k) or other workplace retirement plan if the plan allows it. The key is knowing which source of money is available, whether the distribution is taxable or rollover-eligible, and how it differs from a hardship withdrawal, plan loan, or in-service rollover.
Small Business
What Payroll Taxes Should Small Business Owners Plan For?
Small business owners with employees need to plan for payroll withholding, Social Security and Medicare taxes, FUTA, deposits, payroll tax filings, Form W-2 reporting, state obligations, payroll-provider oversight, and cash set-asides.
Investing
Bond Funds vs. Individual Bonds: Which Should You Use?
Bond funds and individual bonds can both add fixed income to a portfolio, but they differ in maturity, diversification, liquidity, pricing, costs, taxes, and cash-flow control.
Investing
What Role Should Bonds Play in Your Portfolio?
Bonds can support income, diversification, stability, and rebalancing, but they still carry interest-rate, credit, inflation, liquidity, and call risk.
Retirement
How to Use an HSA for Retirement Healthcare Costs
An HSA can be a useful retirement healthcare account if it is funded before Medicare, used for qualified medical expenses, and coordinated with cash reserves, Medicare premiums, taxes, and long-term care risk.
Newsletter
Get clear financial guidance
Get one weekly email with practical money guidance, useful next steps, and none of the noise.
Zero spam. Just clear, honest financial guidance.