You're Close to Retirement. Let's Make Sure You're Ready.

Retirement is within reach, but the shift from building savings to living off them is unlike anything you've navigated before, and the questions that come with it are real.

The Questions Pre-Retirees Are Actually Asking

Most people in their 50s and early 60s aren't wondering about abstract financial theory. They're carrying specific, urgent questions: Do I actually have enough saved? When should I start Social Security to get the most out of it? What do I do about health insurance if I retire before Medicare kicks in at 65? These are the right questions.

 

At A5 Financial, retirement planning for pre-retirees in the Seattle area means working through each of these questions with numbers, not generalities. We model your income, expenses, investment growth, and Social Security timing across a 30-plus-year horizon so you can see exactly where you stand — and what it will take to cross the finish line on your terms.

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The Retirement Readiness Review

The Retirement Readiness Review is A5's structured assessment for pre-retirees who want a real answer to the question "Am I ready?" — not a sales pitch dressed up as a plan.

 

We look at your full financial picture: current assets, projected expenses, Social Security options, healthcare costs, tax exposure, and income strategy. Many clients who come to us worried they've fallen short discover, once everything is modeled out, that they can retire earlier than they expected — often because of inefficiencies in their current plan that we're able to recover. Others learn exactly what they need to do in the next two to three years to get there. Either way, you leave with clarity.

 

  • Full income and expense projection across a 30-plus-year retirement horizon
  • Social Security timing analysis comparing multiple claiming scenarios
  • Portfolio risk review and allocation recommendations
  • Tax-efficient withdrawal sequencing and Roth conversion planning
  • Pre-Medicare healthcare cost planning if retiring before 65
  • Equity compensation review for tech professionals with RSUs, ESPPs, or stock options

Social Security Timing

Claiming Social Security at the wrong time can cost you tens of thousands of dollars over a retirement lifetime. We run detailed scenarios comparing early, full, and delayed claiming strategies against your specific income picture, portfolio size, and health outlook — so the decision you make is the one that maximizes your lifetime benefit, not just your first check.

Pre-Medicare Healthcare Planning

Retiring before 65 means navigating a healthcare gap that catches many people off guard. We factor ACA marketplace coverage and COBRA continuation into your pre-retirement budget so that healthcare costs are planned for — not discovered after you've already made the leap.

Portfolio Risk as Retirement Approaches

The allocation that served you well during your accumulation years may carry more risk than you want heading into retirement. We review your 401(k) and investment mix, identify any dangerous concentrations — including employer stock — and make adjustments on a deliberate timeline so you're not overexposed when the market decides to test you.

How We Engineer the Transition from Paycheck to Portfolio

The hardest part of retiring isn't the financial calculations, but rather it's the psychological shift from receiving a paycheck to drawing down savings. A5's approach is to make that transition feel as structured and reliable as the paycheck it replaces.

 

We begin building your income ladder a few years before your target retirement date, not the week before. Using scheduled maturities from CDs, bonds, and annuities, we construct a layered income stream timed to deliver money when you need it. This all gets paired with a growth sleeve designed to keep pace with inflation over the long run. By the time you retire, the system is already operational. Retirement planning for pre-retirees works best when the runway is built while you still have time to build it well.

A Critical Window for Seattle-Area Tech Professionals

If you work at Amazon, Microsoft, Google, or a Seattle-area startup, the five years before retirement are often the most consequential tax planning window of your financial life. RSU vesting events, peak salary years, and final Roth conversion opportunities tend to converge right here — and the decisions made during this period can have a significant impact on your tax burden in retirement.

 

We help tech professionals sequence equity events, manage concentrated stock positions, and execute Roth conversions deliberately — before the window closes. This kind of equity compensation planning requires coordination across income, taxes, and investments, and it's work we do regularly for clients across the Eastside and greater Seattle region.

Questions Pre-Retirees Ask Us

  • How do I know if I have enough saved to retire in the next few years?

    The honest answer depends on your specific income needs, planned expenses, Social Security timing, and how long your money needs to last. A general savings benchmark won't tell you what you actually need to know. A detailed retirement readiness analysis — one that models your full picture across a 30-plus-year horizon — will. That's the starting point we use with every pre-retiree we work with.

  • When should I take Social Security?

    There's no single right answer, but the decision has lasting consequences. Claiming early reduces your monthly benefit permanently; delaying past full retirement age increases it. The optimal timing depends on your health, other income sources, and whether a spouse's benefit is in the picture. We run a full comparison of your scenarios before recommending a strategy.

  • What do I do about health insurance if I retire before 65?

    You have two primary options: COBRA continuation coverage from your employer plan, or an ACA marketplace plan. Each has tradeoffs in cost, coverage, and income-based subsidy eligibility. We factor healthcare costs into your pre-retirement budget so this isn't a surprise — it's a line item you've already planned for.

  • Should I be doing Roth conversions before I retire?

    For many pre-retirees, the years between now and retirement represent the last window to convert pre-tax savings to Roth at relatively favorable tax rates — before Social Security, RMDs, and other income sources push your bracket higher in retirement. Whether a conversion makes sense depends on your current income, projected future income, and timeline. We model the scenarios before recommending a path.

  • What's the difference between working with A5 and using a large financial institution?

    At A5, you work directly with John Carruthers CFP® and Neil Fenning CFP®. Our focus is on building a retirement plan that fits your life, not on moving assets to a platform that benefits us. For pre-retirees in the Bothell, Bellevue, and greater Seattle area, that distinction matters.