Pre-Retirement Checklist for Restaurant Industry Executives ages 55-65
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For restaurant industry executives, owners, multi-unit operators, general managers, or senior leaders, approaching retirement in your late 50s or early 60s is a pivotal moment.
Unlike many other professions, your wealth may be tied up in a mix of business equity, deferred compensation, retirement accounts, and cash flow from active operations. That makes thoughtful pre-retirement planning essential.
I often tell clients: “Retirement isn’t just a date—it’s a transition. And that transition is easier when you check your financial, business, and personal boxes ahead of time.” Here’s a pre-retirement checklist tailored for restaurant executives (but it applies to others as well!).
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1. Assess Retirement Income Sources
Restaurant executives often have multiple streams of income. Before retiring, identify all potential sources:
• 401(k), 403(b), or SEP/Solo 401(k) plans – Confirm balances, contribution limits, and vesting schedules
• Deferred compensation plans – Understand distribution rules, tax treatment, and employer solvency
• Business equity – Evaluate whether you plan to sell, transition, or retain partial ownership
• Other investments – Stocks, real estate, or other assets
Tip: Map each income source by timing, liquidity, and predictability to ensure you won’t run short in early retirement.
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2. Run a Tax Strategy Review
Taxes can make or break a retirement plan for high-earning executives:
• Roth vs. pre-tax conversions – Consider doing Backdoor Roths or strategic Roth conversions if it reduces long-term tax exposure
• Deferred compensation distributions – Review potential tax brackets in retirement and plan withdrawals carefully
• State taxes – Your current state of residence and planned retirement location can have a huge impact
Tip: A pre-retirement tax plan can save hundreds of thousands over the first 10–15 years of retirement.
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3. Plan Business Transition
For restaurant executives with ownership stakes:
• Decide whether you will sell, step back, or remain partially involved
• Assess the impact of your departure on cash flow, employees, and brand reputation
• Consider succession planning for key management roles
Tip: Even if you’re not an owner, clarify your role and retirement timeline with your employer or board—it affects deferred comp and retirement benefits.
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4. Review Healthcare and Insurance Coverage
Healthcare is often the largest unknown for executives retiring before Medicare eligibility:
• Estimate COBRA, private insurance, or employer retiree coverage costs
• Review long-term care policies and life insurance coverage
• Consider health savings accounts (HSAs) for tax-advantaged medical savings
Tip: Don’t leave insurance planning to chance—unexpected medical expenses are a common retirement derailment.
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5. Test Your Retirement Budget
Many executives overestimate retirement spending. Conduct a “reality check”:
• Create a monthly budget based on current spending, adjusted for lifestyle changes
• Include taxes, healthcare, travel, and contingency for unexpected expenses
• Stress-test for inflation and market volatility
Tip: Target at least 80% of current income as a baseline, but refine with real data and lifestyle goals.
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6. Social Security and Pension Decisions
If eligible for Social Security or other pensions:
• Evaluate optimal claiming ages for maximum benefits
• Understand how Social Security interacts with other income sources (e.g., deferred comp)
• Model benefits in multiple retirement scenarios
Tip: Waiting even a few years to claim Social Security can significantly increase lifetime benefits—especially if you have other income streams.
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7. Debt and Mortgage Review
High-income executives often carry mortgage, business-related, or personal debt:
• Pay down high-interest debt before retirement
• Evaluate whether carrying low-interest mortgage debt is worthwhile versus investing cash elsewhere. Don’t forget to factor in the return that “peace of mind” can give you!
• Consider timing large business loans or owner distributions
Tip: Debt reduction before retirement reduces stress and improves cash flow flexibility.
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8. Estate and Succession Planning
Pre-retirement is the perfect time to get your estate in order:
• Update wills, trusts, and powers of attorney
• Name beneficiaries on all accounts
• Plan business succession and family transitions
Tip: Estate planning isn’t just about death—it’s about control and continuity while you’re living.
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9. Lifestyle and Psychological Preparation
Retirement isn’t just financial—it’s lifestyle:
• Identify your post-retirement daily structure
• Decide how involved you want to remain in your industry
• Consider hobbies, travel, or volunteer work to replace the social and mental stimulation of work
Tip: A clear vision reduces the risk of retirement regret.
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10. Final Thoughts
For restaurant executives approaching 55–65, retirement is a complex mix of financial, business, and lifestyle decisions. A systematic pre-retirement checklist ensures nothing critical is overlooked and creates a roadmap for a smooth, confident transition.
Start early, involve your CPA, CFP®, and any business partners, and remember: retirement is a journey, not a single date. Please reach out if I can help!
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Contact Information Prosperity Financial Planning LLC, Celebration, Florida. elizabeth@prosperityfinancialplanning.com