Your Step-by-Step Timeline to a Confident Retirement (Even If You're Only 55)
👉 Want to learn how to retire without the worry of running out of money in retirement? Click here to watch this video
Why You Should Listen to This
If you’re like many of the investors I’ve worked with, you’ve likely asked yourself, “Can I retire at 55?” or “What should I be doing now to get ready for retirement?” Whether you’re 10 years out or already counting down the months, retirement isn’t just a financial decision—it’s a life transition.
In my experience, the most successful (and stress-free) retirements don’t happen by chance. They happen with a timeline, a strategy, and the right accountability along the way.
Let’s walk through a practical, month-by-month game plan for preparing to retire—with key checkpoints for those starting at 55 and aiming to retire in 5 to 10 years.
Can You Retire at 55?
Yes, many people can—and do—retire at 55. But it requires a thoughtful plan around:
Health insurance (since Medicare doesn’t start until 65)
Withdrawal strategies (to avoid penalties before 59½)
Tax planning (Roth conversions, capital gains, income smoothing)
Income replacement (Social Security won’t kick in yet)
The earlier you start planning, the more options you’ll have.
Your Retirement Readiness Calendar (Starting at Age 55)
This timeline assumes you want to retire around age 60–62. You can adjust it if your timeline is shorter or longer.
📅 Year 1 – Financial Foundation & Vision
January–March
Define what retirement looks like to you (travel, part-time work, grandkids, etc.)
Review all income sources: 401(k), IRAs, pensions, brokerage, rental, Social Security
Track your current spending and estimate retirement lifestyle expenses
April–June
Build a net worth statement
Identify your "retirement number" (how much you need saved to retire)
Meet with a financial advisor to model income and investment strategies
July–September
Check on early withdrawal options (Rule 72(t), SEPP, Roth contributions, etc.)
Evaluate long-term care coverage
Review wills, powers of attorney, and health directives
October–December
Max out retirement contributions (401(k), IRA, HSA)
Rebalance your investment portfolio for your risk tolerance
Begin thinking about where you might want to live in retirement
📅 Year 2 – Strategy + Simplification
January–March
Run a retirement tax projection (what tax bracket will you be in after retiring?)
Explore Roth conversions while you're still earning income
Review estate plan with a qualified attorney
April–June
Simplify financial accounts (consolidate old 401(k)s or IRAs)
Start building up 1–2 years of cash reserves for early retirement years
Evaluate healthcare options for ages 55–65 (ACA, COBRA, health sharing)
July–September
Review pension or annuity options if applicable
Calculate Social Security estimates and explore early vs. delayed strategies
October–December
Test-drive your retirement budget by "living on less" for 3 months
Adjust your investment mix to increase flexibility
📅 Year 3 – Income Engineering
January–March
Revisit your withdrawal plan (sequence matters!)
Map out how to fund the "gap years" (before age 59½ and before 65)
Review Roth-to-traditional ratios for future tax-efficiency
April–June
Confirm 72(t) or Rule of 55 eligibility if retiring this year
Evaluate rental income or part-time work opportunities
Estimate IRMAA impact if your income is higher
July–September
Make catch-up contributions if 50+
Recheck cash flow plan and tweak based on current expenses
October–December
Review Medicare and ACA income thresholds
Set retirement date if not already chosen
đź“… Final 12 Months Before Retirement
January–March
Select healthcare coverage if under 65 (Marketplace, COBRA, etc.)
Run a full tax simulation for the upcoming retirement year
Confirm travel plans, home downsizing, or location changes
April–June
Create an income “paycheck” plan (monthly withdrawals)
Choose a Social Security filing strategy
Notify HR about your retirement timeline and gather benefit statements
July–September
Complete final rollover, pension elections, or investment changes
Set up income automation (direct deposits, account transfers)
Meet with your advisor for final portfolio allocation strategy
October–December
Execute health insurance plan for the next year
Enjoy your last days of full-time work
Host a celebration—you earned it!
đź’ˇ Real-Life Example: How Mark and Lisa Retired at 60 (By Starting at 55)
Background:
Mark (55) and Lisa (53) came to us feeling stuck. They had about $1.3M in combined retirement savings, owned their home, and were both making good incomes. But they weren’t sure if early retirement was realistic—or how to get from “here” to “there.”
Their dream? Retire by 60, travel while healthy, and eventually downsize to a mountain home with access to skiing, hiking, and grandkids.
Step-by-Step Action Plan
Year 1: Vision + Strategy
We helped them define what retirement really looked like: travel 2–3 times per year, $7,000/month lifestyle, no mortgage.
We reviewed all their accounts and found overlapping investments, underused HSAs, and an old 401(k) they hadn’t touched in years.
We projected their retirement income needs, adjusted for inflation, and showed them they’d need about $2.2M total net worth to confidently retire at 60.
Year 2: Income Mapping + Roth Conversions
We started small Roth conversions to reduce future RMDs while they were still in a lower tax bracket.
They maxed out their 401(k) and added $8,000 in catch-up contributions each.
We consolidated and rebalanced their old accounts to simplify and align their investments with their target retirement date.
Year 3–4: Lifestyle Simulation
They “test drove” their retirement budget by living on $7,000/month for six months.
We adjusted their plan to include $15,000/year for travel and a potential second home.
They began exploring ACA health insurance estimates to prepare for the 60–65 Medicare gap.
Year 5: Countdown to Retirement
They sold a rental property and used part of the proceeds to fund a 2-year cash buffer.
We reviewed their Medicare options, income thresholds for IRMAA, and finalized a drawdown plan using their brokerage account, Roths, and IRAs in the right order.
The Result
At age 60, they both walked away from full-time work with complete confidence.
Their plan included $100,000/year of after-tax retirement income, health coverage, and zero financial anxiety.
They took their first month-long trip to Italy within six months of retiring.
👉 The Takeaway: The key wasn’t luck — it was a timeline, accountability, and clear financial modeling. By starting at 55, they gave themselves five full years to course-correct, optimize taxes, and align their money with their vision.
Final Thoughts: Retirement Is a Process, Not an Event
I tell clients all the time: retirement isn’t a cliff you jump off—it’s a journey you prepare for.
Starting at age 55 gives you flexibility, options, and time to build a plan that fits your lifestyle, not just your finances. With the right step-by-step game plan, you can retire confidently—whether that’s at 55, 62, or 70.
👉 Want to learn how to retire without the worry of running out of money in retirement? Click here to watch this video
FAQs
Can I retire at 55?
Yes, if you have the right mix of savings, withdrawal options, and health insurance. The earlier you start planning, the easier it becomes.
What accounts can I use before 59½?
Brokerage accounts, Roth contributions (basis), 72(t) withdrawals, and certain 401(k) plans if you leave a job at 55+.
What’s the biggest mistake people make?
Not planning for taxes or healthcare in the "gap years" before age 65. These can derail an otherwise solid retirement plan.
Disclaimer: Case studies and timelines are hypothetical and do not relate to an actual client of Lock Wealth Management. Clients or potential clients should not interpret any part of the content as a guarantee of achieving similar results or satisfaction if they engage Lock Wealth Management for investment advisory services.