Retirement Planning Built Around Every Variable, Not Just the Market

A confident retirement comes from knowing your income will last, your taxes are managed, and your plan accounts for what you can't predict. Crane Capital Management delivers fiduciary retirement planning services that go well beyond projected portfolio growth — coordinating Social Security timing, Roth conversion strategy, withdrawal sequencing, and healthcare cost planning into one coherent income plan.

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Your Retirement Has Too Many Variables to Leave to a Spreadsheet

Most retirement projections show you a number. A real retirement income plan accounts for the sequence in which you draw from accounts, how Roth conversions affect your tax bracket in the years before you stop working, when to claim Social Security, and how healthcare costs escalate over a 20- to 30-year horizon. Taylor Harwood, CFA® and CFP®, holds one of the rarer credential combinations in independent financial planning — both the analytical depth to stress-test portfolio assumptions and the planning discipline to coordinate every piece of a retirement income strategy.

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What Retirement Planning Actually Covers

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Social Security Timing Strategy

The decision of when to claim Social Security is not a single calculation — it's a coordination question. We model claiming scenarios against your other income sources, projected tax bracket, and longevity to identify a strategy that serves the full plan, not just the highest monthly benefit in isolation.

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Tax-Efficient Withdrawal Sequencing

Drawing from the wrong accounts in the wrong order can cost more in taxes over a 20-year retirement than most people realize. We build withdrawal strategies that sequence distributions across taxable, tax-deferred, and tax-free accounts to manage bracket exposure and reduce lifetime tax burden. Roth conversion planning in the years before retirement is often a significant part of this work.

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Healthcare Cost Planning

Medicare premiums, supplemental coverage, and out-of-pocket cost inflation need to be built into a retirement income plan from the start, not patched in later. We incorporate realistic healthcare cost projections and guide clients through Medicare enrollment and plan selection so the budget reflects what retirement actually costs.

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Business Owner Retirement Planning

Business owners face retirement decisions that employees don't. The timing and structure of a business exit can significantly affect how much of the proceeds are available as retirement income, how they're taxed, and what self-employed plan options make sense in the years leading up to a transition. We coordinate exit planning and retirement income planning together so neither decision is made in isolation.

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Estate Coordination

Beneficiary designations and estate documents that made sense at 45 may not align with a retirement income strategy at 65. We coordinate retirement planning with estate planning so the decisions you make about income, account structure, and legacy don't contradict each other.

We start by defining your vision of retirement and what it looks like in daily life.

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We map out all financial resources, from accounts to business proceeds.

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We design a withdrawal and income strategy that balances cash flow, taxes, and flexibility.

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We revisit the plan regularly, adjusting for new goals, market shifts, or changes in tax law.

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How Retirement Planning Comes Together Over Time
FAQs

Retirement Planning Questions, Answered Directly

  • When should I start planning for retirement with a financial advisor?

    The most useful time to engage a retirement planner is earlier than most people expect — ideally 10 to 15 years before your target retirement date. That window allows for meaningful Roth conversion planning, Social Security strategy modeling, and tax bracket management that simply isn't available if you wait until the year before you stop working.

  • How do I create a retirement income plan that lasts?

    A durable retirement income plan accounts for more than projected portfolio growth. It models withdrawal sequencing across account types, manages sequence-of-returns risk in the early years of retirement, incorporates realistic healthcare cost escalation, and builds in flexibility for market conditions that change over a 20- to 30-year horizon. We build that kind of plan — not a projection that assumes everything goes right.

  • Should I do a Roth conversion before I retire?

    For many clients, the years between stopping work and beginning Social Security represent a window of lower taxable income that may be well-suited for Roth conversions. Whether a conversion makes sense depends on your current bracket, projected RMDs, estate goals, and state tax situation. We model the scenarios before recommending a direction.

  • What is the best order to withdraw from retirement accounts?

    The conventional guidance — taxable accounts first, then tax-deferred, then Roth — is a starting point, not a rule. The optimal sequence depends on your bracket, Social Security timing, RMD projections, and whether managing estate value is a priority. Withdrawal sequencing is one of the areas where a coordinated plan consistently outperforms a generic approach.

  • How do I plan for healthcare costs in retirement?

    We build Medicare premiums, supplemental coverage costs, and long-term care assumptions directly into the income plan. Healthcare is one of the largest and most inflation-sensitive expenses in retirement, and leaving it as an afterthought creates gaps that compound over time.

  • Can a financial advisor help me time Social Security benefits?

    Yes — and the difference in lifetime benefits between a well-timed claiming strategy and a default decision can be substantial. We model Social Security claiming scenarios against your full financial picture, including other income sources, tax implications, and spousal coordination where applicable.

  • Do you work with business owners on retirement planning?

    Yes. Business owners often have retirement planning decisions that are directly tied to their exit timeline and deal structure. We work with business owners to align exit planning with retirement income goals, evaluate self-employed plan options in the years before a transition, and coordinate with transaction advisors when a sale is on the horizon.

Know Your Number. Know Your Plan.

Retirement confidence isn't a feeling — it's the result of a plan that accounts for taxes, income sequencing, healthcare costs, and the variables that matter to your life. If you're within 15 years of retirement, or already there, this is the right time to stress-test your picture.

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