Your 5-Year Retirement Readiness Checklist

Smart Living, Real Freedom, and a Plan That Makes Sense Retirement isn’t just about quitting work. It’s about gaining time, freedom, and peace of mind. Whether you plan to stop working completely, shift into part-time, or start something new on your own terms — these next five years matter. This is when you tighten the plan, reduce overwhelm, and build security without stress. This is your clear, no-fluff checklist for getting retirement-ready — even if you’re not sure what “retirement” means to you yet.

5 Years Out: Lay the Foundation

• ☐ Review all income streams (Social Security, pensions, savings, side income)

• ☐ Get honest about expenses — current + future lifestyle goals

• ☐ Calculate gaps (do you need to earn more, spend less, or both?)

• ☐ Explore semi-retirement paths (freelance, consulting, passive income)

• ☐ Set a “freedom date” — it keeps you focused, even if flexible - we are aiming to retire at 60 - 62 still young but old enough

🎯 Tip: This is when clarity matters more than numbers. Know where you are. Know where you want to be.

3 Years Out: Trim, Tidy, Transition

• ☐ Pay off or down key debts (especially high-interest ones) - we love Amex, US Bank, Alley cards

• ☐ Declutter your finances — consolidate accounts, cancel unused things

• ☐ Re-evaluate housing (stay? downsize? rent for flexibility?) - we are building ADU and converting garage to junior ADU

• ☐ Automate saving + investing for max efficiency

• ☐ Simplify your digital and paper systems — less stress, less chaos - we do not use checks and taxes are digital

🧘 Smart living = less clutter + more control.

2 Years Out: Protect & Prepare

• ☐ Meet with a financial planner (or run your own projections with tools)

• ☐ Update legal docs — will, power of attorney, medical directives - make sure to also have living trust otherwise your local government will decide what happens to your assets

• ☐ Learn how Medicare works (and when you need to enroll) - also look into buying extra insurance

• ☐ Get real about health goals — food, movement, mindset - we fast 20 + hours and we walk at least 10K a day, weekends we hike to 20K

• ☐ Start testing your future routine — hobbies, time structure, rhythm - learn new trades, anything that is opposite of your natural years of career

🛡️ Peace of mind comes from preparation, not perfection.

1 Year Out: Test the Lifestyle

• ☐ Live on your “retirement budget” for a few months - buy what you need not what you want, say NO, dont buy anything that on sale just becuase

• ☐ See how it feels — do you need more flexibility or income?

• ☐ Look for volunteer or low-pressure ways to stay active + engaged

• ☐ Try part-time living in a dream location (travel, Airbnb, local test runs) - or buy cheap, used RV and travel around and see before settling

• ☐ Talk to others already retired — learn what surprised them most

🧭 Think of this year as your trial run — edit, refine, adjust.

Bonus: Smart Living Musts

• Set up digital banking with alerts and automation - we set all bills alert 10 days before due date

• Start or update a “freedom file” — your key info + goals in one place - we have google sheets that is being updated once a week

• Protect your identity + privacy (especially online) - do not open any email or text links, verify the information beforehand

• Maintain routines for movement, community, joy

• Make space for you-time — your next chapter deserves it - we have moring black coffee with fire pit on watching sun rise and birds sing every single day (no exceptions)

Final Word

You don’t need millions.
You don’t need to rush.
You just need a plan — and permission to define “retirement” your own way.

Whether you downsize, travel, work less, or launch something new — Retirement is just the next version of smart living.