When Can I Retire? vs. Should I Retire?
For most people, the idea of retirement is both exciting and intimidating. Over years of financial planning conversations, we’ve noticed one question comes up more than any other:
“When can I retire?”
It’s an important question — but not always the most important one. As you approach the transition, a deeper and more meaningful question emerges:
“Should I retire?”
While both questions are essential, when you ask them, and how you use the answers, can shape your entire retirement journey.
Why These Two Questions Matter
Retirement today is not the same as it was 30 years ago. People are living longer, careers are more flexible, and the traditional “work until 65, then stop” path doesn’t fit everyone.
“When can I retire?” is about readiness on paper.
“Should I retire?” is about readiness in life.
The right question at the right time can lead to a successful, meaningful, and fulfilling retirement.
When Can I Retire?
(Best for people 5+ years away — or even earlier!)
This is the most common question we hear, and for good reason. If you’re more than five years from your planned retirement, this is the perfect time to ask it.
In fact, if you’re ambitious, you can ask it in your 20s, 30s, or even as a teenager just entering the workforce. The earlier you ask, the more power you have to influence the answer.
Why Early Matters: The Power of Time
When it comes to retirement, time is leverage. Small decisions made early — saving a little more, spending a little less, investing wisely — can compound into major differences later. It can also provide the permission to spend more freely now, it isn’t always about saving more money.
Want to see what happens if you increase your savings by 2%? Run the numbers.
Thinking about working a few more years? Model the impact.
Wondering how a new house purchase might impact your retirement numbers? Explore the trade-offs.
The earlier you ask, the more flexibility you have to adjust your path and test assumptions.
Action Steps If You’re Asking “When Can I Retire?”
Define your vision. What does retirement look like to you — travel, hobbies, family time, part-time work?
Estimate expenses. Consider current spending and expected changes leading up to and through retirement.
Assess income sources. Work Income, Pensions, Social Security, retirement accounts, investments, and other streams — and how these evolve over time.
Run scenarios. Use calculators or work with a planner to test “what if” situations.
Adjust early. If there’s a gap, you still have time to make meaningful changes.
Should I Retire?
(Best for those within 5 years of retirement — or already financially able to retire)
Fast-forward to five years (or fewer) before your expected retirement date. By this point, for many people, the math already works. The question shifts.
Instead of asking “Can I retire?”, you start asking:
“Should I retire?”
This is where the financial numbers take a back seat to the qualitative side of retirement — purpose, fulfillment, and readiness for a major life transition.
Why This Question Is Deeper Than the Numbers
At this stage, you may already have a clear sense of your retirement income and expenses. The challenge becomes deciding whether it’s the right time to step away.
Will retiring now mean cutting back on travel or other goals?
Will delaying retirement give you more freedom — or take away precious healthy years?
Are you emotionally ready to leave the identity and structure work provides?
Questions to Ask Before You Retire
What will my daily life look like in retirement?
Who will I spend time with?
Do I have hobbies, interests, or activities to fill my days meaningfully?
Am I retiring from something (burnout) or to something (a fulfilling new chapter)?
The Emotional Side of Retirement
For decades, your life has been structured around work. Retirement removes that structure, replacing it with open time — which can be both liberating and unsettling.
Some thrive immediately, diving into travel, hobbies, and volunteering.
Others struggle, experiencing boredom, loss of identity, or social isolation.
A gradual transition — part-time work, consulting, or “test driving” retirement with extended vacations — can help bridge the gap.
Retirement Is Not Just a Math Problem
It’s easy to view retirement as a financial equation:
assets – expenses = security
But retirement is a life equation:
money + purpose + health = fulfillment
That’s why, when the numbers say “yes,” it’s important to pause and also ask:
“Should I?”
Navigating the Transition Period
Between the questions “When can I retire?” and “Should I retire?” lies a critical transition phase. Here’s how to approach it:
Test-drive retirement. Try extended time off to see how it feels.
Plan non-financially. Build a schedule of hobbies, social activities, and personal growth.
Explore phased options. Many employers allow phased retirement, consulting, or part-time work.
Prepare mentally. Read, talk to retirees, and visualize your new routine.
FAQs About Retirement Decisions
1. What if I retire and regret it?
Many people can return to work, even if not in the same role. Keeping skills sharp and networks active helps.
2. Can I retire early and still collect Social Security later?
Yes. Benefits can begin at 62, but delaying increases your payout. A planner can help model the best timing.
3. Is it okay to retire gradually?
Absolutely. Many people find a phased approach (consulting, part-time, or project work) is the smoothest path.
Final Thought
If you’re still several years out, “When can I retire?” is a powerful planning tool.
If you’re nearing the transition, “Should I retire?” becomes the better compass.
Retirement is not a date — it’s a decision. The key is knowing which question to ask and taking the time to answer honestly.
Ready to Explore Your Own Retirement Questions?
At Sanders Retirement Planning, we help people navigate both sides of retirement — the numbers and the life decisions. Whether you’re 20 years away or just 6 months from retirement, we can help you build clarity and confidence.
Have questions?
Let’s talk about what retirement could look like for you.
All content is for informational and educational purposes only and should not be construed as personalized investment, tax, or legal advice. Sanders Retirement Planning LLC does not provide legal or tax advice. Please consult your financial advisor, tax professional, or attorney regarding your specific situation. The information provided is believed to be from reliable sources, but its accuracy and completeness cannot be guaranteed. Links to third-party sites are for informational use only and do not constitute an endorsement. Past performance is not indicative of future results. All investments carry risk, including the potential loss of principal. Advisory services offered through Sanders Retirement Planning LLC, a Registered Investment Adviser. Services may not be available in all jurisdictions.