Many investors focus on diversifying assets (stocks, bonds) but overlook diversifying their accounts by tax treatment (pre-tax 401k, after-tax brokerage, tax-free Roth). This 'tax diversification' provides crucial flexibility in retirement, preventing a situation where every withdrawn dollar is taxable.
If a 401(k) plan allows it, high earners can make after-tax contributions beyond standard limits and then convert those funds to a Roth account within the plan. This strategy bypasses typical Roth income limitations, creating a large, tax-free growth vehicle for retirement.
Investors with highly appreciated, concentrated stock can use financial products similar to real estate's 1031 exchange. They can pool their stock into a newly created, diversified ETF, deferring the capital gains tax event. This solves the immediate diversification risk, though the original low cost basis carries over.
Employees often face surprise tax bills from equity compensation like RSUs because they don't perceive the value transfer as tangibly as a cash bonus. This psychological disconnect means they fail to proactively plan for the significant income tax event that occurs upon vesting, leading to unexpected financial strain.
Retirees can strategically convert their traditional retirement accounts to Roths, paying the income tax at their own, likely lower, rate. This allows their high-earning children to inherit the funds completely tax-free, avoiding a larger tax bill that would have been calculated at the children's peak-earnings tax rate.