Choose Your Own Retirement Adventure
Investing budgeting Dave Ramsey Will Roth IRA 401k 403b savings DebtA guide to designing a retirement you’ll love based on the decisions you make today.
For decades, retirement was often described as a destination a finish line. But the truth is, retirement is an adventure. It’s a chapter filled with choices, possibilities, and new beginnings. And just like any adventure, your outcomes depend on the decisions you make right now.
So today, you get to choose your own retirement path.
Imagine yourself at the crossroads. Three paths stretch ahead:
Path A: Comfortably Coasting
You’ve saved modestly. You want to live simply. You picture quiet mornings, part-time hobbies, and meaningful family time.
Path B: Boundless Lifestyle
You want flexibility, travel, new experiences, more freedom than ever before.
Path C: Purpose-Driven Retirement
You’re excited about your next chapter, but not because you plan to stop working, you plan to start something new.
You may see yourself clearly on one path, or a mix of all three.
Where you go next will depend on the decisions you make now.
Let's choose your adventure.
Adventure Chapter 1: Financial Foundations
Choice 1: Have you calculated your retirement income?
✔ Yes → You can map annual spending confidently
⬜ Not yet → Start with income sources such as Social Security, investments, pensions, and part-time income
Outcome: When you know your income, you know your boundaries, and your opportunities.
Choice 2: Will you use a structured withdrawal strategy?
✔ Use a plan → More tax-efficient income and longer portfolio life
⬜ Withdraw as needed → Higher risk of depletion
Outcome: Intentional withdrawal planning may increase how long retirement savings last, sometimes by years.
Choice 3: Have you chosen when to claim Social Security?
✔ Yes → Great
⬜ Not yet → This decision alone can mean six figures over a lifetime
Outcome: Waiting to claim often increases permanent income, but not always. Coordination matters.
Adventure Chapter 2: How You Spend Your Time
Retirement is not just about money, it’s about meaning.
Which best describes your vision?
A. Freedom & Relaxation
- Morning walks
- Weekly golf
- Grandkids visit often
- Low stress
B. Exploration & Adventure
- Travel the world
- Seasonal living
- Cruise itineraries
- Bucket list experiences
C. Purpose & Contribution
- Volunteering
- Mentoring
- Consulting
- Launching a passion project
None of these are “right.” What matters is alignment with who you are.
Because…
A meaningful retirement is rarely about what you stop doing. It’s about what you start doing.
Adventure Chapter 3: Future-Proofing Decisions
No adventure is risk-free but preparation makes it smoother.
Choice 1: Will your lifestyle remain stable if markets fluctuate?
✔ Yes → Planning was done
⬜ Not sure → Consider reducing sequence-of-returns risk
Choice 2: Have you prepared for future healthcare needs?
✔ Medicare strategy in place
⬜ Working on it
Choice 3: Do your estate documents match your wishes?
✔ Yes
⬜ I need updates
Outcome: When these pieces are planned, you gain freedom not restriction.
Choose Your Ending
Ending #1 — The Protected Lifestyle
- You retire with confidence.
- Your income supports your lifestyle.
- You travel when you want.
- You pursue what brings joy.
- And when life changes, your plan adapts.
Ending #2 — The Purpose-Driven Legacy
- You build something meaningful.
- Your time, experience, and resources impact others.
- Your estate plan creates generational direction.
- Your retirement becomes more than a moment, it becomes contribution.
Ending #3 — The Unplanned Chapter
- You improvise decisions year-to-year.
- Markets dictate your lifestyle.
- Unexpected costs disrupt your plans.
- Your vision shrinks.
Of these endings only one truly happens by accident.
The other two are designed.
You don’t have to choose blindly. And you don’t need to retire with uncertainty.
There’s no better time to plan than today— because your retirement adventure doesn’t happen someday.