Straightforward answers to the questions Alan hears most often — about Medicare, Social Security, long-term care, retirement income, and working with a fiduciary advisor in the Greater Richmond area.
Alan Crawford is a fiduciary retirement planner and the founder and principal of Peak Confidence Retirement Planning, based in Midlothian, Virginia. He holds three specialized designations: NSSA® (National Social Security Advisor), RICP® (Retirement Income Certified Professional), and CLTC® (Certified in Long-Term Care). He is a licensed Series 65 Investment Adviser Representative of Sequent Planning, LLC, a registered investment adviser.
Alan works personally with every client — serving individuals and families throughout Midlothian, the Greater Richmond Metro area, and clients nationwide through virtual meetings.
Peak Confidence specializes in helping individuals and couples approaching or entering retirement navigate the key decisions that determine long-term financial security. Core focus areas include:
Medicare planning for those turning 65 · Social Security optimization · Retirement income planning · Long-term care planning · Investment management
The practice is built around a simple principle: Medicare is often the first major retirement decision — and getting it right opens the door to everything else.
NSSA® — National Social Security Advisor: Specialized training in Social Security claiming strategies, spousal coordination, and lifetime income optimization.
RICP® — Retirement Income Certified Professional: Graduate-level education from The American College of Financial Services in retirement income planning, sustainable withdrawal strategies, tax-efficient distribution, and longevity risk management.
CLTC® — Certified in Long-Term Care: Specialized knowledge in long-term care planning, coverage options, and care coordination strategies.
Series 65: Licensed Investment Adviser Representative (IAR) of Sequent Planning, LLC, a registered investment adviser — authorizing Alan to provide investment advisory services and charge fees for financial planning.
Yes. In his role as an Investment Adviser Representative, Alan operates as a fiduciary for investment advisory and financial planning services — legally and ethically obligated to act in your best interest at all times.
For Medicare and long-term care insurance planning, Alan operates as an independent insurance advisor and is committed to the same standard of putting client interests first, with full transparency about how he is compensated.
Alan's practice has two distinct sides, and compensation works differently for each — with full transparency in both cases.
Compensated exclusively through client fees — AUM fee, monthly subscription, or flat project fee. No commissions. No product sales.
Compensated by the insurance carrier when a policy is placed — the standard industry model. No direct cost to you. Always disclosed upfront.
Alan is committed to limiting conflicts of interest and provides full, proactive disclosure of any compensation arrangement that falls outside his flat-fee or AUM structure. You are never obligated to purchase a policy through Alan.
Several of Alan's most valuable services are provided at no cost to the client, with no obligation to engage further:
✦ Social Security optimization analysis — personalized review of your optimal claiming age, spousal coordination, and lifetime income impact
✦ Retirement cash flow analysis — a projection of your income, expenses, and asset sustainability throughout retirement
✦ Medicare planning — complete guidance on enrollment timing, plan comparison, and pathway selection
✦ Long-term care insurance planning — assessment of your risk and coverage options
These services are available on a standalone basis. You do not need to engage Alan for comprehensive financial planning to benefit from them.
Schedule a no-cost conversation →Social Security is one of the most valuable financial assets most Americans own — yet the decision of when and how to claim it is frequently made without careful analysis. A difference of just a few years in claiming age can mean tens of thousands of dollars in lifetime income. For a married couple, coordinating claiming strategies between spouses can mean even more.
Alan offers this analysis at no charge because it is genuinely useful on its own — and because understanding your Social Security income clarifies how much you need from your portfolio, when you can realistically retire, and how Medicare and long-term care fit into your overall plan.
"Fee-only" means an advisor receives zero commissions — all compensation comes exclusively from client fees. That term accurately describes Alan's retirement income planning, wealth management, and financial planning services, where no commissions are earned.
However, Alan also provides Medicare supplement and long-term care insurance planning, for which he is compensated by insurance carriers through standard industry commissions. These services carry no direct cost to the client, and any commission arrangement is fully disclosed.
The more precise description: Alan operates as an independent insurance advisor with carrier compensation for Medicare and LTC, alongside a fee-only investment and financial planning practice. This structure is common among comprehensive retirement planners and, when properly disclosed, serves clients well.
No. Medicare planning, long-term care planning, Social Security analysis, and retirement cash flow analysis are all available as standalone services at no cost. Many clients engage Alan solely for Medicare guidance as they approach 65, or for a Social Security analysis in their late 50s or early 60s, with no obligation to pursue broader financial planning.
For those who choose to engage Alan as their comprehensive retirement planner, all of these services are integrated into the overall plan — because they are essential components of a complete retirement strategy.
The process begins with an introductory conversation — at no cost and with no obligation — to understand your situation and determine whether there's a good fit. From there, Alan gathers information about your financial picture, goals, and concerns and develops a personalized plan addressing your specific priorities.
Clients meet regularly with Alan to review their plan and make adjustments as their life and the financial landscape evolve. Alan works personally with every client — you will always be working directly with him, not handed off to a junior associate or call center.
This is the most fundamental retirement planning question — and it depends on several interconnected factors: your expected expenses, your income sources (Social Security, pensions, investment withdrawals), your total assets, anticipated healthcare costs, and how long you may live.
A retirement readiness analysis looks at all of these together to model whether your resources are likely to support your lifestyle throughout retirement. Rather than relying on rules of thumb, Alan builds a personalized projection based on your specific numbers, goals, and circumstances — and provides it at no cost as a starting point.
This is fundamentally a question about longevity risk — the risk of outliving your assets. A comprehensive retirement income plan models your projected spending, income streams, investment portfolio, and realistic rates of return to estimate how long your money is likely to last under a range of scenarios.
Factors like Social Security claiming age, sequence of returns risk, inflation, healthcare costs, and long-term care all affect the answer significantly. The goal of retirement income planning is to give you a high degree of confidence that your assets will last as long as you do — even under unfavorable conditions.
Sequence of returns risk refers to the danger that poor investment returns early in retirement — when you are actively withdrawing from your portfolio — can permanently impair your financial security, even if long-term average returns eventually recover.
A significant market decline in the first few years of retirement is far more damaging than the same decline occurring later. Addressing this risk through income floor strategies, asset segmentation, and careful withdrawal planning is one of the core functions of a well-designed retirement income plan.
Tax planning is one of the most overlooked and highest-impact components of retirement planning. Decisions about Roth conversions, the sequence in which you draw from taxable, tax-deferred (IRA/401k), and tax-free (Roth) accounts, Social Security benefit taxation, IRMAA thresholds, and required minimum distributions can have significant effects on how long your money lasts and how much of it you keep.
Alan incorporates tax-efficient distribution strategies into every retirement income plan.
Most people become eligible for Medicare at age 65. Your Initial Enrollment Period (IEP) is a 7-month window that begins 3 months before the month you turn 65, includes your birthday month, and extends 3 months after.
Enrolling during the first 3 months of your IEP — before your birthday month — ensures your coverage starts on time with no gap. Missing this window without a qualifying exception can result in permanent late enrollment penalties that follow you for the rest of your life.
Not necessarily — but the answer depends critically on the size of your employer.
Your employer coverage is generally primary. You may delay Medicare without penalty and enroll during a Special Enrollment Period when coverage ends.
Medicare becomes your primary coverage at 65. You should enroll to avoid coverage gaps and permanent penalties.
Only if you are already receiving Social Security benefits before your 65th birthday. In that case, you will be automatically enrolled in Medicare Parts A and B and receive your card approximately three months before you turn 65.
If you are not yet receiving Social Security — which is increasingly common as people delay claiming to maximize their benefit — you must actively enroll through the Social Security Administration at ssa.gov, by phone, or in person at a local SSA office.
Creditable coverage refers to health or prescription drug insurance that meets Medicare's minimum standards. If you delay enrolling in Medicare Part D (prescription drugs) because you have other coverage, that coverage must be "creditable" to protect you from a late enrollment penalty when you eventually do enroll.
Your employer or plan administrator is required to notify you annually whether your coverage meets the creditable standard. Keep these notices — you may need them when you enroll.
Medicare Part A (hospital insurance) is premium-free for most people who have worked and paid Medicare taxes for at least 10 years (40 quarters). However, Medicare is not free overall.
Medicare Part B (outpatient medical) carries a standard monthly premium of $202.90 in 2026 for most beneficiaries. There are also deductibles, copayments, and coinsurance — and critically, there is no annual out-of-pocket maximum under Original Medicare alone. This exposure is the primary reason most people add either a Medigap supplement or a Medicare Advantage plan.
IRMAA stands for Income-Related Monthly Adjustment Amount — an additional premium surcharge applied to Medicare Parts B and D for higher-income beneficiaries. It is based on your modified adjusted gross income (MAGI) from your tax return two years prior.
In 2026, IRMAA surcharges begin for individuals with income above $106,000 and married couples filing jointly above $212,000.
Original Medicare (Parts A and B) has several significant coverage gaps that surprise many new enrollees:
✦ Routine dental, vision, and hearing — generally not covered
✦ Long-term custodial care — nursing home, assisted living, or home care for daily activities
✦ Prescription drugs — requires a separate Part D plan
✦ Care outside the United States — mostly not covered
✦ No out-of-pocket maximum — unlimited exposure under Original Medicare alone
These gaps are among the primary reasons to consider supplemental coverage and a separate long-term care plan.
Under Original Medicare (Parts A and B), you can see any doctor or use any hospital in the country that accepts Medicare — and the vast majority do. There are no networks and no referrals required.
Under Medicare Advantage, coverage is typically limited to the plan's provider network, which varies by plan and geographic area. Before enrolling in any Medicare Advantage plan, it is essential to verify that your specific doctors and preferred hospitals are included in that plan's network.
This is the central Medicare decision most people face at enrollment.
Higher monthly premiums. Any provider nationwide that accepts Medicare. No networks, no referrals. Predictable, capped out-of-pocket costs. No dental/vision/hearing unless added separately.
Lower or $0 premiums. Provider networks (HMO or PPO). Copays and cost-sharing. Prior authorization for some services. Often includes dental, vision, hearing, and Part D.
The right choice depends on your health, your current providers, your medications, your finances, your travel habits, and your tolerance for uncertainty. This decision is among the most valuable conversations you can have with an independent Medicare advisor.
This is one of the most critical points people discover too late. When you first enroll in Medicare at 65, you have guaranteed issue rights — Medigap insurers cannot deny you coverage or charge higher premiums based on pre-existing conditions.
However, if you choose Medicare Advantage at enrollment and later want to switch to Medigap, you will generally be subject to medical underwriting in Virginia and most other states. This means the insurer can review your health history, deny coverage entirely, or charge significantly higher premiums. For many people who have developed health conditions, switching back becomes very difficult or financially impractical.
The two most widely chosen Medigap plans for new enrollees today are Plan G and Plan N.
Plan G covers nearly all out-of-pocket costs under Original Medicare — the only expense you pay is the annual Part B deductible ($257 in 2026). Plan N has lower monthly premiums but requires copayments for some office and emergency room visits.
Because Medigap benefits are standardized by federal law, the same Plan G from any insurer provides identical benefits — which means comparing premiums across carriers is meaningful and worthwhile. Plan F, historically the most comprehensive option, is no longer available to those who became Medicare-eligible after January 1, 2020.
Coverage while traveling varies significantly by plan type. HMO-based Medicare Advantage plans typically cover only emergency and urgent care outside the plan's service area. PPO plans offer somewhat more flexibility but may still apply higher cost-sharing for out-of-network providers.
Original Medicare with a Medigap supplement, by contrast, covers you at any provider anywhere in the country that accepts Medicare — making it the preferred choice for frequent travelers, snowbirds, or anyone with a second home in another state.
Long-term care refers to ongoing assistance with activities of daily living — bathing, dressing, eating, mobility, and continence — typically required due to aging, chronic illness, injury, or cognitive decline such as dementia or Alzheimer's disease.
In Virginia, the average cost of a private room in a nursing home exceeds $100,000 per year. Home care costs have risen sharply as well. Medicare covers very limited long-term care and does not cover custodial care at all. Without a plan, the full cost falls on your savings or your family.
The best time is well before you need it — ideally in your mid-50s to early 60s. Long-term care insurance is significantly less expensive and far easier to qualify for at younger ages when you are in good health. Once health conditions develop, options narrow considerably.
Many people delay this conversation until it feels urgent — by which point they may be uninsurable or facing premiums that are no longer cost-effective.
✦ Traditional long-term care insurance — provides a daily or monthly benefit for qualifying care needs; most cost-effective when obtained in good health
✦ Hybrid life/LTC products — combines a life insurance death benefit with LTC coverage; addresses the "use it or lose it" concern and guarantees a return of premium if care is never needed
✦ Annuity/LTC combinations — uses existing assets to fund LTC coverage through an annuity with an LTC rider
✦ Self-insuring — intentionally setting aside assets to fund potential care costs; viable for those with substantial assets and a clear plan
✦ Medicaid — a safety net for those who qualify based on income and asset levels
Each option involves meaningful trade-offs that depend on your assets, health, family situation, and preferences.
Medicare covers skilled nursing facility care only following a qualifying hospital inpatient stay of at least three days, and only for a limited duration — up to 100 days per benefit period, with significant cost-sharing after day 20.
Medicare does not cover custodial care — the ongoing help with daily activities that most people associate with long-term care. This is one of the most important and most frequently misunderstood gaps in Medicare coverage.
Peak Confidence Retirement Planning is based in Midlothian, Virginia, and serves clients throughout the Greater Richmond Metro area — including the City of Richmond and the counties of Chesterfield, Henrico, Powhatan, Goochland, and Hanover. In-person meetings are available throughout the Richmond area.
Virtual meetings are available for clients throughout Virginia and across the country.
Medicare decisions have meaningful local dimensions that national call centers and online enrollment platforms cannot fully address. Medicare Advantage provider networks vary by county and zip code — a plan that includes your preferred physicians in one county may not cover the same physicians in another.
Alan works specifically in the Greater Richmond market and is familiar with the local healthcare landscape — including Bon Secours, VCU Health, and HCA Virginia — which directly informs the Medicare guidance he provides to clients in Midlothian, Chesterfield, Henrico, and surrounding areas.
The easiest way is to call or text 804-250-1034, or visit the contact page at pcretire.com. There is no cost for an initial conversation and no obligation to proceed.
Alan works personally with every client from the very first call.
Go to the contact page →Alan responds personally to every inquiry — typically within one business day. The first conversation is always free, always no pressure, and always focused on giving you a straight answer.
You can begin Social Security as early as age 62 at a permanently reduced benefit, or delay up to age 70, earning approximately 8% per year in increased benefit for each year you wait beyond your Full Retirement Age (FRA). For most people born in 1960 or later, FRA is 67.
The optimal claiming age depends on your health and family history, whether you are married, your other income sources, your tax situation, and whether you plan to continue working. There is no single right answer — but there is a right answer for your specific situation, which is why Social Security optimization deserves careful, personalized analysis.
If you claim Social Security before your Full Retirement Age and continue to earn income from work, your benefit may be temporarily reduced if your earnings exceed the annual earnings limit ($23,400 in 2026 for those below FRA). For every $2 you earn above this limit, $1 is withheld from your benefit.
These withheld amounts are not permanently lost — once you reach your Full Retirement Age, your benefit is recalculated upward to credit the months in which benefits were withheld. After FRA, there is no earnings limit and you can work and collect your full benefit simultaneously.
A spouse who has little or no Social Security earnings history may be eligible for a spousal benefit of up to 50% of the other spouse's full retirement age benefit. Spousal benefits can begin as early as age 62 but are permanently reduced if claimed before the recipient spouse's own FRA.
Coordinating claiming strategies between spouses — particularly the timing of the higher earner's benefit — can significantly affect the household's lifetime income and is one of the highest-impact areas of Social Security planning. The higher earner's benefit also becomes the survivor benefit, making that claiming decision especially consequential for the surviving spouse's long-term security.
If you are already receiving Social Security benefits when you turn 65, you will be automatically enrolled in Medicare Parts A and B, and your Part B premium will be deducted directly from your Social Security payment.
If you are delaying Social Security — a common strategy for maximizing lifetime benefits — you must enroll in Medicare separately and pay your Part B premium directly. Additionally, income received during the years you delay Social Security can affect IRMAA surcharges and your overall tax picture, making coordination between the two decisions especially important.