Five Questions That Reveal Whether You’re Truly Ready to Retire

You probably already know how many dollars sit in your 401(k). But that number alone doesn’t tell you if you should hand in your notice.
These five questions do. Answer yes to each one and you may be ready to trade the grind for the life you’ve imagined.

1 | Are you still postponing the life you want?

Be honest: Are the phrases “someday,” “after this project,” “next year” on repeat?
Work-first living crowds out time with the people and passions that matter most. If travel, grand-kids’ soccer games, woodworking or simply slow mornings keep getting shoved to “later,” consider what those delays are costing you. Retirement isn’t just an exit from work; it’s an entry into the experiences you’ve deferred.

2 | Is work eroding your health?

Long hours, chronic stress and poor sleep can nudge blood pressure up and energy down. When appointments, exercise and genuine rest always take a back seat to deadlines, the bill eventually comes due. Retirement can hand you back the hours needed for workouts, healthier meals and long-ignored medical check-ups. You worked hard to earn your money—make sure you’re healthy enough to enjoy it.

3 | Can’t scale back?

Some employers gladly offer phased retirement, part-time roles or consulting gigs. Others expect you fully on or fully gone. If your current position leaves zero room to reduce hours, and you’re craving more freedom now (not five years from now), a clean break may be the only path to reclaiming your calendar.

4 | Do you see a clear picture of daily life after the office?

Picture the dog that finally catches the car—then stares at it, confused. Many new retirees feel the same if they haven’t built a vision for their time. Do you know what your mornings look like without a commute? Which hobbies, volunteer projects, trips or classes will give your days shape? If you’ve sketched out a purpose-filled routine that excites you, you’re ahead of the game.

5 | Have you run the numbers—really?

A confident “yes” here is non-negotiable.

• Cash-flow plan: You’ve mapped fixed costs, discretionary spending, healthcare, taxes and inflation.

• Income streams: You know exactly when Social Security, pensions, portfolio withdrawals or part-time earnings start—and how long they last.

• Stress tests: Your plan survives market drops, higher inflation and surprise expenses without forcing you back to work.

Whether you hire a planner or crunch it yourself, clarity on the math turns retirement from a leap of faith into a thoughtful step.

If You Answered “Yes” All Around

You’re likely ready to replace “someday” with “today.” Say goodbye to the grind and hello to the life you’ve earned.

If One or More Answers Were “Not Yet”

Good news—that means you’ve identified the gaps. Shore up the finances, craft the daily-life blueprint, negotiate reduced hours or prioritize your health. The moment you can answer yes across the board, you’ll retire with confidence instead of doubt.