Tax Planning Guide
A proactive tax strategy lowers what you owe across your lifetime, not just this April. Our guides cover Roth conversions, capital gains planning, bracket management, and tax-efficient investing, written for families and business owners in Forest Hill and the Baltimore metro area.
Tax planning is the ongoing process of arranging your income, deductions, account withdrawals, and financial decisions to legally minimize the taxes you owe across your lifetime, not just in the current year. It includes strategies like Roth conversions, tax-loss harvesting, bracket management, timing of capital gains, charitable giving structures, and coordinating withdrawals across taxable, tax-deferred, and tax-free accounts.
A year-round tax planning calendar spaces out the moves that save retirees the most, from funding IRAs and HSAs early in the year to pacing Roth conversions, harvesting losses, and meeting year-end RMD and QCD deadlines.
Read the complete guide →The major areas of tax strategy, each covered in depth with its own guide and related articles.
Should I Do Roth Conversions During the Gap Years Before RMDs? Last reviewed: July 2026 Yes, for most pre-retirees with large pre-tax balances, the gap years are the best window of your life to run a roth conversion strategy. The gap years are the stretch between when your paycheck stops and when required minimum distributions begin at age 73, and ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
What expired in the TCJA sunset and what did OBBBA make permanent? Last reviewed: July 2026 Most of the 2017 Tax Cuts and Jobs Act was written to expire at the end of 2025. That deadline was the TCJA sunset, and it would have raised taxes for nearly every household in 2026. Then the One Big Beautiful Bill Act, known ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
What is a mega backdoor Roth, and how do I use one? Last reviewed: July 2026 A mega backdoor Roth is a strategy that lets certain 401(k) savers move tens of thousands of dollars of after-tax contributions into a Roth account each year, far beyond the standard Roth IRA limit. For 2026, it can route as much as $72,000 in ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
What Is Net Unrealized Appreciation (NUA) on Company Stock in My 401(k)? Last reviewed: July 2026 Net unrealized appreciation (NUA) is an IRS rule that lets you pay long-term capital gains rates on the growth of company stock distributed from your 401(k), instead of ordinary income tax on the full value. You pay ordinary income tax only on the original ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
What is a mega backdoor Roth, and how do I do one? Last reviewed: July 2026 A mega backdoor Roth is a strategy that lets you contribute up to $47,500 into a Roth account through your 401(k), well above the standard $24,500 elective deferral limit. You make after-tax contributions to your 401(k) plan, then convert those dollars to Roth, either ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
What is a 1031 exchange, and how does it defer tax on investment property? Last reviewed: July 2026 A 1031 exchange lets you sell an investment property and reinvest the proceeds into another qualifying property without paying capital gains tax in the year of the sale. The tax is deferred, not erased. You carry your original cost basis and your ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
What is the difference between qualified and ordinary dividends? Last reviewed: July 2026 The difference is the tax rate: qualified dividends are taxed at the lower long-term capital gains rates (0%, 15%, or 20%), while ordinary dividends are taxed as regular income at your marginal rate (up to 37%). Both are payments from your investments, but for the same dollar ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
How should high earners pay off student loans? Last reviewed: July 2026 High earners should attack student loans based on interest rate: aggressively pay off anything above roughly 6%, split between payoff and investing in the 4 to 6% range, and prioritize investing below 4% once retirement accounts are maxed, while refinancing high-rate private loans and skipping forgiveness programs they ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
What is the difference between tax credits and tax deductions? Last reviewed: July 2026 A tax deduction lowers your taxable income, while a tax credit lowers your tax bill directly, dollar for dollar, which makes credits almost always more valuable. A $1,000 deduction saves you only your tax rate on that amount, somewhere between $100 and $370 depending on your ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
What is a year-round tax planning calendar for retirees and pre-retirees? Last reviewed: July 2026 A year-round tax planning calendar is a month-by-month schedule that spaces out the tax moves, like Roth conversions, tax-loss harvesting, required distributions, and charitable giving, that are far more effective when planned across the year than rushed in December. Most people treat taxes as an ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
What are all my options when rolling over or withdrawing from an old 401(k)? Last reviewed: July 2026 You have four 401(k) rollover options when you leave a job: leave the money in your old employer's plan, roll it into your new employer's plan, roll it into an IRA, or cash it out. For most people, rolling into an IRA ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
What Are the Biggest First-Year-of-Retirement Tax Mistakes? Last reviewed: July 2026 The biggest first-year-of-retirement tax mistakes are withdrawing too much too fast, mistiming required minimum distributions, skipping tax withholding once a paycheck disappears, and ignoring how those moves ripple into Social Security taxation, Medicare premiums, and Maryland state tax. One uncoordinated year can quietly cost a retiree several thousand dollars. ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
What Not to Put in a Roth IRA: 7 Assets to Keep Out Last reviewed: July 2026 The short answer to what not to put in a Roth IRA: municipal bonds, highly speculative single stocks, money you may need before 59½, holdings likely to post real losses, appreciated shares you plan to donate, already-tax-efficient index funds, and illiquid alternatives. A ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
What does the One Big Beautiful Bill Act change for your money? Last reviewed: July 2026 The One Big Beautiful Bill Act is the federal tax law signed on July 4, 2025, that locked in the 2017 tax cuts and added a batch of new breaks. For most people, it means the lower tax rates and bigger standard deduction did ... <div><a href="https://chesapeakefp.com/perspectives/tax-planning/" class="more-link">Read More</a></div>
Every article in the tax planning pillar, covering strategies from Roth conversions to capital gains management.
Tax planning is proactive and year-round, focused on legally reducing future taxes through decisions made in advance. Tax preparation is a backward-looking annual process of reporting what already happened.
A Roth conversion moves money from a pre-tax IRA or 401k to a Roth account, paying ordinary income tax now in exchange for tax-free growth and withdrawals later. It makes the most sense when your current tax rate is lower than your expected future rate.
Tax-loss harvesting means selling an investment at a loss to offset capital gains elsewhere in your portfolio. The loss can also offset up to $3,000 of ordinary income annually, with excess losses carried forward.
Capital gains on assets held longer than one year are taxed at 0%, 15%, or 20% depending on your total taxable income. In 2026, the 0% rate applies up to $48,350 for single filers and $96,700 for married couples filing jointly.
A 1099-R reports distributions from retirement accounts, pensions, and annuities. The taxable amount in box 2a is ordinary income. If you took a distribution before age 59 and a half, a 10% early withdrawal penalty may apply unless an exception applies.
The standard deduction for 2026 is $15,000 for single filers and $30,000 for married filing jointly. Itemizing makes sense only if your deductible expenses exceed your standard deduction. Bunching deductions into alternating years can make itemizing worthwhile.
Managing Partner of Chesapeake Financial Planners in Forest Hill, Maryland, serving families and business owners across Harford County and the Baltimore metro area.
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