A clear answer on readiness
Whether you can retire when you want to, and exactly what it takes if you can't yet.
Retirement is close. Let's make sure you're ready.
For people 2 to 5 years from retirement who want certainty, not a best guess, about whether they can stop working.
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What is a pre-retiree?
A pre-retiree is someone within a few years of leaving work for good, usually 2 to 5 years out. It's the highest-leverage planning window there is: close enough to model your real numbers, and early enough to still change the outcome.
You've spent decades saving. Now the question changes. Not 'am I saving enough?' but 'can I actually stop?' The years right before retirement are when the biggest, least-reversible decisions get made, and when a real plan matters most.
All planning is covered by a single transparent flat fee — no percentage of assets, no commissions. Meet Ryan Langan, CFP®.
What’s on your mind.
- Can we actually afford to retire when we want to?
- Will we have to cut back on the life we pictured?
- How do we handle health insurance before Medicare?
- Are we leaving money on the table with taxes or Social Security?
Where we focus
What we work on together.
The income switch
A plan for turning decades of saving into a steady paycheck that lasts.
Tax positioning
Setting up the low-tax years before required withdrawals begin, so you keep more of what you built.
The pre-65 healthcare gap
A plan to bridge coverage if you retire before Medicare, without derailing your income.
The countdown
Your 2-to-5-year countdown
1. Model your retirement income
Can your savings and Social Security replace your paycheck? This is the first question to answer, and it shapes everything else.
2. Set your Social Security strategy
When to claim, and how to coordinate benefits if you're married. The timing affects your lifetime income from the program.
3. Plan your tax-bracket staging
The years before required withdrawals begin are your window for Roth conversions. Once RMDs start, your options narrow.
4. Bridge your healthcare gap
If you'll retire before Medicare at 65, you need a plan for coverage. This is one of the most overlooked costs in pre-retirement planning.
5. Review your investment drawdown plan
Which accounts do you pull from first, and in what order? The sequence affects how long your money lasts.
The services that matter most for you.
Frequently asked questions.
- How far out should I start planning?
- Most of the people I work with are 2 to 5 years from retirement. That window is when the highest-leverage decisions get made, so the earlier in it we start, the more options you have.
- What if I'm not sure I can actually afford to retire?
- That's exactly what the plan answers. We model your real numbers so you get a clear yes, or a clear path to yes, instead of a hunch.
- I'm still 10 years out. Can you help?
- My focus is people within about 5 years of retirement, where planning has the most leverage. If you're further out, reach out anyway and I'll point you in a useful direction.
- What should I do 5 years before retirement?
- Five years out is when the biggest decisions start coming into focus. Four things matter most: figure out whether your savings and Social Security can replace your paycheck, set a claiming strategy for benefits, look at Roth conversions in the years before required withdrawals begin, and plan how you'll cover health insurance if you retire before Medicare. You don't need to solve all of them at once, but you need a timeline for each.
- How do I prepare financially for retirement?
- Start with the question that matters most: can your savings and Social Security replace your paycheck for the years you expect to be retired? From there, work through taxes, healthcare, and your withdrawal strategy. The order matters, because each decision affects the next one. That's why a flat-fee plan walks through all of it in sequence, so nothing falls through the cracks.
Written by Ryan Langan, CFP®
Founder of Your Path Fi, a fee-only fiduciary firm. Last reviewed May 2026.
Also working with someone who is retirees? See how I approach planning for that stage too. And if you'd like to understand how I charge for this work, explore my flat-fee pricing before we talk.
Let’s see if we’re a fit.
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