Retirement Planning Guide
Build a retirement income strategy that covers healthcare costs, Social Security timing, tax efficiency, and portfolio withdrawals, guided by a CFP professional serving Forest Hill and the greater Baltimore metro area.
Retirement income planning is the process of converting savings into reliable, tax-efficient income for life. A complete plan covers Social Security claiming strategy, withdrawal sequencing across taxable and tax-deferred accounts, Required Minimum Distributions, healthcare cost projections, inflation adjustments, and a spending plan that accounts for early-retirement flexibility and later-stage longevity. It produces a specific, year-by-year income picture, not a generic savings target.
There is no magic retirement number that works for everyone. The amount you need depends on your spending, timeline, Social Security, pensions, and other income sources. This guide walks through how to calculate your personal retirement target.
Read the complete guide →The major decisions within retirement income planning, each with its own guide and supporting articles.
What is sequence of returns risk, and why do the first years of retirement matter most? Last reviewed: July 2026 Sequence of returns risk is the danger that poor investment returns in the first few years of retirement permanently shrink a portfolio that has to last another 25 to 35 years. Two retirees with the same average return over 30 ... <div><a href="https://chesapeakefp.com/perspectives/retirement-planning/" class="more-link">Read More</a></div>
What is the best order to withdraw from my 401k, Roth IRA, and taxable accounts in retirement? Last reviewed: July 2026 The conventional best order to withdraw in retirement is taxable accounts first, tax-deferred accounts like a 401(k) or traditional IRA second, and Roth accounts last, because this sequence lets your tax-advantaged money keep growing the longest. But the conventional ... <div><a href="https://chesapeakefp.com/perspectives/retirement-planning/" class="more-link">Read More</a></div>
What does the SECURE 2.0 Act mean for retirement savers? Last reviewed: July 2026 The SECURE 2.0 Act is a federal retirement law that rewrote dozens of rules for savers, from when you must start withdrawals to how much you can stash in the years right before retirement. Passed at the end of 2022, it phases in over several years, ... <div><a href="https://chesapeakefp.com/perspectives/retirement-planning/" class="more-link">Read More</a></div>
How to Use an HSA for Retirement: A Stealth IRA Strategy Last reviewed: July 2026 Using an HSA for retirement works because the Health Savings Account combines three tax advantages no other account can match: contributions reduce your taxable income, growth is tax-free, and qualified withdrawals are tax-free for life. The 2026 limits, set by IRS Revenue Procedure 2025-19, are ... <div><a href="https://chesapeakefp.com/perspectives/retirement-planning/" class="more-link">Read More</a></div>
The Backdoor Roth IRA: A Step-by-Step Guide Last reviewed: July 2026 A backdoor Roth IRA is a perfectly legal workaround for high earners who can't contribute directly to a Roth IRA. You make a nondeductible contribution to a traditional IRA, then convert it to a Roth IRA, paying tax only on any gains between the contribution and the conversion. If ... <div><a href="https://chesapeakefp.com/perspectives/retirement-planning/" class="more-link">Read More</a></div>
Should I Choose a Roth IRA or Traditional IRA? Last reviewed: July 2026 The choice between a Roth IRA vs Traditional IRA comes down to one question: do you want your tax break now or in retirement? A Roth IRA takes your after-tax dollars today and pays out completely tax-free later. A Traditional IRA gives you a deduction now and ... <div><a href="https://chesapeakefp.com/perspectives/retirement-planning/" class="more-link">Read More</a></div>
What Are the Rules and Strategies for Required Minimum Distributions? Last reviewed: July 2026 Required minimum distributions (RMDs) are mandatory annual withdrawals the IRS forces you to take from tax-deferred retirement accounts starting at age 73. You pay ordinary income tax on every dollar, whether you need the money or not. The amount is set by dividing your prior year-end ... <div><a href="https://chesapeakefp.com/perspectives/retirement-planning/" class="more-link">Read More</a></div>
How Do I Maximize My 401(k) Employer Match? Last reviewed: July 2026 Capturing your full employer match 401k contribution is the highest-return move available to most workers with retirement money. Most plans match between 3 and 6 percent of pay, and missing the match forfeits an instant 50 to 100 percent return that compounds for the next two or three ... <div><a href="https://chesapeakefp.com/perspectives/retirement-planning/" class="more-link">Read More</a></div>
How Much Money Do I Actually Need to Retire Comfortably? Last reviewed: July 2026 How much to retire is the question we hear more than any other at Chesapeake Financial Planners, and the honest answer is that your number is personal. There is no universal figure that works for every household in Forest Hill, Harford County, or anywhere else. Your ... <div><a href="https://chesapeakefp.com/perspectives/retirement-planning/" class="more-link">Read More</a></div>
Every article in the retirement planning pillar, organized for easy reference.
The right number depends on your expected spending, not a rule of thumb. Multiply your planned annual expenses by 25 as a starting estimate using the 4% guideline, then adjust for Social Security income, any pension, healthcare costs before Medicare, and how long your portfolio needs to last.
The break-even point for delaying from 62 to 70 is roughly age 80 to 82 for most people. If you expect to live past that and have other income to cover the gap, delaying increases your benefit by 6 to 8 percent per year and permanently raises your survivor benefit.
The 4% rule is a starting guideline derived from historical market data, not a guarantee. A flexible withdrawal strategy that adjusts spending in down markets extends portfolio longevity significantly. Your sustainable rate depends on your asset allocation, retirement length, and other income sources.
Taxes in retirement are highly variable and often higher than people expect. Traditional IRA and 401k withdrawals are taxed as ordinary income. Required Minimum Distributions at 73 can push you into higher brackets. Up to 85% of Social Security benefits can be taxable.
A Required Minimum Distribution is the amount the IRS requires you to withdraw from pre-tax retirement accounts each year starting at age 73. Failing to take the full RMD results in a 25% excise tax on the shortfall.
Options include COBRA, a spouse's employer plan, marketplace coverage under the ACA with potential premium subsidies, or a Health Savings Account balance. The ACA marketplace is often the most cost-effective choice if your income is below about 400% of the federal poverty level in early retirement.
Paying off a mortgage eliminates a fixed monthly obligation and reduces the income your portfolio needs to generate, which lowers sequence-of-returns risk. Whether it makes mathematical sense depends on your mortgage rate versus expected portfolio returns.
Managing Partner of Chesapeake Financial Planners in Forest Hill, Maryland, serving families and business owners across Harford County and the Baltimore metro area.
Schedule a no-obligation Fit Call to see whether we are the right fit for your retirement.
See If You’re A Fit