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10 Steps to a Smarter Retirement in 2025: Your Complete Guide

10 Steps to a Smarter Retirement in 2025: Your Complete Guide

April 30, 2025

Retirement planning can feel like a puzzle, but it’s easier with a clear roadmap. In the final episode of the A Smarter Way to Retire 10-step series, Tony Leonardi, a CERTIFIED FINANCIAL PLANNER® professional, recaps his proven process to create a secure, adaptable retirement plan for 2025. Whether you’re just starting or refining your strategy, this guide connects the dots from organizing finances to making ongoing adjustments. Based on Tony’s book A Smarter Way to Retire and MoneyGuidePro tools, these steps empower you to retire confidently. Listen to the full episode on Apple Podcasts or Spotify, sign up for our free 2025 Retirement Reset Checklist by entering your email at 2025-retirement-reset-checklist, and watch our Taxes in Retirement Webinar - Strategies to Keep More of Your Money at Webinar or YouTube!

Why a 10-Step Retirement Plan Matters

“A retirement plan isn’t a one-time task—it’s a living process,” says Tony Leonardi, CFP® professional. This 10-step framework, detailed in A Smarter Way to Retire, builds a plan that evolves with your life, markets, and goals. Why is a structured retirement plan important? It organizes finances, aligns investments with goals, and adapts to changes, ensuring long-term security and confidence. Sign up for our free 2025 Retirement Reset Checklist by entering your email at 2025-retirement-reset-checklist to take control today.

Step 1: Get Organized

How do I start retirement planning? Gather investment statements, retirement accounts, pensions, Social Security estimates, and debts. “Break out those shoeboxes or pasta bowls!” Tony jokes. Understanding your complete financial landscape—assets and liabilities—sets the foundation for informed decisions.

Step 2: Build a Financial Model

What is a financial model for retirement? It’s a projection of future income, expenses, and investment growth to test if your plan is on track. “Finance is just math,” says Tony Leonardi, a CERTIFIED FINANCIAL PLANNER® practitioner. Use software like MoneyGuidePro to test scenarios, adjust for inflation, and track success probability. Find a tool you’re comfortable with or visit LeonardiFamilyWealthcare.com for personalized modeling.

Step 3: Address Expectations and Concerns

What should I consider for retirement lifestyle? Define your vision—travel, part-time work, or volunteering—and address fears like market crashes or healthcare costs. Tony encourages couples to align expectations. “Have that conversation with your partner,” he advises, to shape a plan that fits your dreams, balancing lifestyle and financial concerns.

Step 4: Define Your Retirement Timeframe

How does longevity affect retirement planning? Living to 90 or 100 requires more savings, influencing investments and Social Security decisions. “Your timeframe shapes your plan,” says Tony. Whether retiring early or working longer, set a realistic timeline with your partner to guide your strategy.

Step 5: Set Goals and Budget

How do I budget for retirement? Break expenses into three categories: 

Needs: Essentials like housing, healthcare, and groceries, adjusted for inflation. 
Wants: Lifestyle goals like travel or hobbies that add joy. 
Wishes: Aspirational goals like vacation homes or charitable gifts.
Prioritizing these ensures your plan covers necessities while supporting your dreams. Sign up for our free 2025 Retirement Reset Checklist by entering your email at 2025-retirement-reset-checklist to start budgeting.


Step 6: Understand Income Sources

What are common retirement income sources? Social Security, pensions, 401(k)s, IRAs, rentals, or part-time work. “Cover needs with steady income like Social Security,” Tony suggests, using volatile investments for wants and wishes. Tax planning is key—watch our Taxes in Retirement Webinar - Strategies to Keep More of Your Money at Tax Planning Webinar or YouTube to optimize withdrawals.

Step 7: Measure Risk Tolerance

How do I assess retirement risk tolerance? Evaluate your comfort with market volatility and affordability to align your portfolio with goals. “Risk tolerance isn’t just emotions,” says Tony Leonardi, CFP® professional. Score your risk individually, then agree on a household risk level with your partner for growth and stability.

Step 8: Analyze Current Investments

How do I know if my investments are retirement-ready? Check for diversification, risk exposure, and income potential. “Many portfolios need a major adjustment,” Tony notes. Use tools like the efficient frontier to ensure investments support income generation and long-term goals, adjusting to align with your retirement strategy.

Step 9: Measure Probability of Success

What is a good probability of success for retirement? A 70–90% probability, tested via Monte Carlo analysis, indicates a solid plan. “Stress-test your plan,” says Tony. Low scores signal adjustments—Tony’s seen plans from 0% to 99% improve with tweaks. No situation is hopeless with the right strategy.

Step 10: Make Adjustments and Improvements

How often should I adjust my retirement plan? Make immediate adjustments after analysis (e.g., portfolio rebalancing, budget tweaks) and ongoing check-ins yearly or after life changes. “Your plan is a living document,” says Tony Leonardi, a CERTIFIED FINANCIAL PLANNER® professional. Flexibility is key to long-term success.

Fun Fact: Even 0% Plans Can Improve

“No situation is doomed,” Tony shares. Over years of running financial plans, he’s boosted scores from 0% to near 99% with adjustments. Small tweaks, like optimizing taxes or rebalancing, can transform your retirement outlook.

Three Questions to Start Your 2025 Plan

Tony wraps the episode with these prompts: 

Have you organized your financial documents to see your full picture? 
Are your investments and budget aligned with your risk tolerance and goals? 
Do you have a model to test your plan’s success probability?
Answer these by signing up for our 2025 Retirement Reset Checklist with your email at 2025-Retirement-Reset-Checklist.
FAQ: Your 2025 Retirement Planning Questions Answered

Q: What’s the first step in retirement planning?
A: Organize all financial documents—investments, accounts, and debts—to understand your starting point. 

Q: How do I test my retirement plan’s success?
A: Use Monte Carlo analysis with tools like MoneyGuidePro to measure your plan’s 70–90% success probability. 

Q: Where can I learn more about retirement taxes?
A: Watch our Taxes in Retirement Webinar - Strategies to Keep More of Your Money at Taxes in Retirement Webinar or YouTube

Conclusion

Tony Leonardi, a CERTIFIED FINANCIAL PLANNER® professional, connects the 10 steps to a smarter 2025 retirement—organizing finances, modeling success, and staying adaptable. With A Smarter Way to Retire, you’re set for confidence and freedom. Listen to the full episode on Apple Podcasts or Spotify, sign up for our free 2025 Retirement Reset Checklist by entering your email at 2025-Retirement-Reset-Checklist, and explore our Taxes in Retirement Webinar - Strategies to Keep More of Your Money at Tax Webinar or YouTube. Please refer to our website for full disclosures and resources. What’s your first step? Comment below or share this post!