🛠 Skilled Trades Retirement Checklist

You’ve spent years building, fixing, and creating things that last. Retirement should be no different. But for skilled trades professionals, retirement planning often looks different than for white-collar workers. It’s not just about a pension or a 401(k) — it’s about turning decades of work, union benefits, and sometimes even a business you’ve built, into a future you can count on.

This checklist is designed for you — the tradesperson ready to retire, sell a shop, or step back after a lifetime on the tools. It covers the essentials: cash flow, benefits, and insurance.

Use it as a guide, a self-check, and a conversation starter with your family, union, or trusted advisor. Because just like your projects, a well-built retirement plan starts with the right blueprint.

💵 CASH FLOW & INCOME CLARITY

✅ I know my monthly income and expenses today
✅ I know what my pension, annuity, or 401(k) benefit will provide at retirement
✅ I’ve factored in side income (overtime, side jobs, or rental property)
✅ I’ve created a budget for my first year of retirement
✅ I’ve identified any “bridge income” needed between leaving work and full benefits

💰 SAVINGS, INVESTMENTS & BUSINESS VALUE

✅ I have a retirement savings account (401(k), IRA, union annuity, etc.)
✅ I’ve contributed regularly and increased savings when possible
✅ I’ve had my small business, shop, or tools/equipment valued
✅ I have a plan for how to invest a lump sum if I sell my business or get a payout
✅ I know how much of my savings should be kept in cash vs. invested

📈 TAX & BENEFIT STRATEGY

✅ I’ve spoken with a CPA about taxes on pensions, annuities, or a business sale
✅ I understand how retirement income affects Social Security and Medicare costs
✅ I’ve considered tax-smart moves (Roth conversions, installment sales, etc.)
✅ I’ve reviewed union-specific benefits with someone who understands them
✅ I know my spouse/partner’s benefits and how they coordinate with mine

🔐 INSURANCE, PROTECTION & LEGACY

✅ I have health coverage lined up post-retirement (union, COBRA, Medicare, private)
✅ I’ve reviewed long-term care insurance options
✅ I’ve updated beneficiaries on retirement accounts and insurance
✅ I have a will, power of attorney, and health care directive in place
✅ I’ve considered how to pass on or sell my tools, equipment, and shop inventory

📂 ORGANIZATION & NEXT CHAPTER

✅ All key documents (union benefits, pension, insurance, legal) are in one place
✅ My family knows who to call for financial and legal guidance if something happens to me
✅ I’ve set reminders for benefit deadlines and tax filings
✅ I’ve created a “next chapter” plan: how I’ll spend time, stay social, and find purpose
✅ I’ve thought about fraud and scams that target retirees, and how to avoid them

🔧 TRADE-SPECIFIC PRIORITIES

✅ I’ve factored in the reality that physical health may push me to retire earlier than expected
✅ I’ve explored creative succession options (selling to employees, ESOP, installment sale)
✅ I’ve prepared emotionally to step back from the camaraderie of the trade community
✅ I’ve reviewed whether union benefits integrate smoothly with outside investments

🔎 Skilled Trades Retirement Readiness Score

Count your ✅s:

22–30: You’re well-prepared to retire confidently.

15–21: Solid foundation — focus on your weakest category before making big moves.

Under 15: Gaps exist that could cost you money or peace of mind — get a coordinated plan in place now.

Let’s Make It Happen

💼 Want help reviewing your checklist and creating a retirement income plan? Schedule a no-pressure strategy call — free, confidential, judgment-free today.

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Disclaimer: The information provided on this site and its blogs is for educational and informational purposes only. It does not constitute financial, legal, or tax advice. Always consult with a qualified professional for guidance tailored to your individual circumstances. The examples, illustrations, and sample checklists are intended for general reference and are not meant to reflect any individual or family's specific needs or outcomes. They are provided to demonstrate concepts and do not guarantee future results. All investing involves risk, including possible loss of principal. Past performance is not indicative of future results.