Retirement Transition Field Guide
The 5–10 Years Before Retirement Are Where Most Mistakes Happen
Not because people aren’t saving—but because they haven’t structured how it turns into income.
Saving consistently.
Investing for growth.
Letting time and discipline do their work.
Now, as retirement gets closer, the questions begin to change.
Not just how much you’ve accumulated—
but how it actually turns into income.
How it’s taxed.
How it holds up over time.
This guide is designed to help you think through that transition in a more structured way. If you’d like a version you can keep, download it hear.
Your Portfolio Has a New Job
For most of your career, your financial strategy had one objective: accumulate assets.
You contributed to retirement accounts, invested for growth, and allowed compounding to work in your favor.
As retirement approaches, that role begins to shift.
Your portfolio is no longer just a growth engine.
It becomes the source of your income.
And that transition—more than anything else—is where planning becomes more nuanced.
Clarify Your Retirement Vision
Before getting into numbers or strategies, it’s worth stepping back and defining what retirement actually looks like for you.
Identify your intended retirement age
Estimate baseline spending needs
Estimate lifestyle spending
Consider where you plan to live in retirement
Discuss expectations with your spouse or partner
Guide Insight:
Retirement planning begins with clarity around the life your assets must support.
Understand Your Future Income Sources
Retirement income rarely comes from one place. It’s typically a combination of sources working together.
Review Social Security benefit estimates
Evaluate possible claiming strategies
Confirm pension benefits if applicable
Identify rental or passive income streams
Estimate the income gap your portfolio must fill
Guide Insight:
Retirement income planning focuses on constructing a dependable paycheck from multiple sources. Get the guide
Prepare Your Investment Portfolio
A portfolio built for accumulation often needs adjustment as retirement approaches.
Review asset allocation and risk exposure
Evaluate how the portfolio supports withdrawals
Identify concentration risk
Review diversification across asset classes
Confirm alignment with your retirement timeline
Guide Insight:
A portfolio designed for accumulation often requires adjustment as retirement approaches.
Evaluate Tax Planning Opportunities
Taxes don’t stop in retirement—in many ways, they become more important.
Review projected tax brackets
Consider Roth conversion strategies
Coordinate withdrawals between taxable, IRA, and Roth accounts
Evaluate capital gains exposure
Review charitable planning opportunities
Guide Insight:
Tax planning can significantly influence how long retirement assets last.
Plan for Healthcare and Medicare
Healthcare is often one of the largest and least predictable retirement expenses.
Estimate retirement healthcare costs
Understand Medicare enrollment timing
Evaluate supplemental insurance options
Consider long-term care planning strategies
Guide Insight:
Healthcare often becomes one of the largest retirement expenses.
Review Estate and Legacy Planning
As retirement approaches, it’s important to ensure everything is structured the way you intend.
Confirm beneficiary designations
Review wills and trusts
Confirm powers of attorney
Review healthcare directives
Discuss legacy intentions with family
Guide Insight:
Estate planning ensures assets transfer efficiently and according to your wishes.
Design Your Retirement Withdrawal Strategy
How you draw from your portfolio often matters as much as how it’s invested.
Estimate sustainable withdrawal rates
Determine withdrawal sequencing
Understand required minimum distribution rules
Stress-test the plan against market volatility
Guide Insight:
Retirement outcomes are often shaped by withdrawal strategy more than investment returns. Get the guide
Retirement Transition Scorecard
As you read through this guide, you can use it as a simple checklist.
Count the number of items you’ve addressed across each section.
Score Interpretation:
0–10 → Early planning stage. Several areas may need attention
11–20 → Good progress. Your retirement framework is forming
21–30 → Well positioned. Many key planning elements are aligned
31+ → Strong alignment across major retirement planning decisions
Understanding Your Results
This scorecard is intended as a reflection tool—not a prediction of retirement success.
For many professionals, the five to ten years leading up to retirement is when the most meaningful decisions take place—particularly around income, taxes, and portfolio structure.
If reviewing this guide raises questions about your own transition, that’s typically a sign you’re at the stage where more structured planning can be helpful.
A Simple Next Step
If you’re within a few years of retirement, this is typically the stage where the questions become more specific—how this applies to your situation, your accounts, your timing.
If you’d like a second set of eyes on that, I offer a short introductory conversation.
Schedule a 20-Minute Retirement Fit Call
A focused conversation to review where you are today—and whether working together may make sense.
About Sentient Financial
I work with professionals in the 5–10 years leading up to retirement, helping them transition from saving to generating reliable, tax-aware income.
Most of the people I work with have done well building assets.
The focus shifts to making sure those assets are structured to support the next phase of life.
Sentient Financial is a fee-only, fiduciary advisory firm.
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This material is provided for educational purposes only and should not be considered personalized investment advice.