6. Retirement Might Not Mean You Stop Working
The traditional “work until 65, then never work again” retirement is becoming increasingly rare. Many retirees discover they need or want to continue earning money—or at least doing some form of paid work.
Why retirees return to work:
Financial necessity:
- Underestimated expenses (especially healthcare)
- Market downturns that devastated retirement savings
- Pension reductions or eliminations
- Longer lifespans requiring savings to last 30+ years
- Supporting adult children or grandchildren financially
Purpose and identity:
- Missing the sense of productivity work provided
- Needing structure and routine
- Wanting to feel valuable and needed
- Combating boredom and isolation
Social connection:
- Work provides automatic social interaction
- Combats loneliness
- Gives a reason to leave the house
Health insurance:
- If retiring before 65 (Medicare age), work can provide health insurance
- Employer coverage is often better than individual plans
The modern retirement: Many people now embrace “semi-retirement” or “phased retirement”:
- Part-time work (15-25 hours/week)
- Consulting or freelancing in their former field
- Starting a small business
- Taking a completely different job in a lower-stress field
- Seasonal work
- Gig economy jobs (driving, delivery, etc.)
Benefits of semi-retirement:
Financial:
- Supplemental income extends retirement savings
- May allow delaying Social Security (increasing benefits)
- Keeps you eligible for employer benefits
- Provides emergency fund cushion
Non-financial:
- Maintains purpose and structure
- Keeps mind sharp
- Provides social connection
- Offers flexibility (work when you want)
- Reduces the jarring transition from full-time work to nothing
Popular retirement jobs:
- Consulting: Using your professional expertise part-time
- Retail: Working in stores you enjoy (hobby shops, bookstores, garden centers)
- Hospitality: Hotels, tour companies, national parks (seasonal)
- Education: Substitute teaching, tutoring, adjunct teaching
- Customer service: Working from home for call centers
- Driving: Uber, Lyft, delivery services
- Skilled trades: Handyman work, repairs, consulting
- Creative pursuits: Turning hobbies into income (Etsy shops, photography, writing)
What successful semi-retirees do:
- Choose work they actually enjoy (not just for money)
- Set boundaries (only work X hours, certain days off, etc.)
- Negotiate flexible schedules
- Protect retirement time and activities
- View work as supplemental, not primary income
What retirees say: “I retired at 64 thinking I’d never work again. By 66, I was bored and our savings were being depleted faster than planned. Now I work part-time at a garden center three days a week. I love it, and the extra $1,200/month makes a huge difference.” – Tom, 68
7. You’ll Worry About Money More Than You Expected
Even retirees with substantial savings often experience financial anxiety in retirement. The shift from earning a paycheck to drawing down savings is psychologically difficult.
Why money anxiety increases:
No more paychecks: For decades, money came IN regularly. Now, money only goes OUT. Even if you’re financially secure, watching your savings decrease is stressful.
Unknown lifespan: Will your money last 20 years? 30? 40? Nobody knows how long they’ll live, making it impossible to know how much you actually need.
Market volatility: When you were working, market downturns were annoying but recoverable. In retirement, a bad market year can significantly impact your financial security. You don’t have time to recover from losses.
Inflation: What costs $1,000 today might cost $2,000 in 20 years. Your fixed income may not keep pace with rising costs.
Unexpected expenses: Home repairs, car replacements, medical emergencies—these major expenses can devastate a fixed retirement income.
The “one more year” syndrome: Some people keep working “just one more year” to build more savings, but the financial anxiety never quite disappears no matter how much they save.
The spending paradox:
Many retirees struggle to actually SPEND their savings. After decades of saving and being frugal, transitioning to drawing down accounts feels wrong. Some retirees live more frugally in retirement than necessary because they can’t bring themselves to spend what they’ve saved.
How to manage retirement financial anxiety:
Create a detailed budget:
- Know exactly how much you need monthly
- Track spending meticulously
- Build in cushion for unexpected expenses
- Update regularly as costs change
Diversify income sources:
- Social Security
- Pension (if available)
- Investment withdrawals (401k, IRA)
- Part-time work income
- Annuities (guaranteed income)
Use safe withdrawal strategies:
- The “4% rule”: Withdraw no more than 4% of savings annually
- Adjust withdrawals based on market performance
- Consider bucket strategies (short-term, mid-term, long-term funds)
Build emergency reserves:
- Keep 1-2 years of expenses in cash/short-term investments
- This provides peace of mind during market downturns
Work with a financial advisor:
- Professional guidance reduces anxiety
- Helps create sustainable withdrawal plans
- Provides accountability and expertise
Focus on what you can control:
- Spending habits
- Healthcare choices
- Part-time income opportunities
- Housing costs
What retirees say: “I have $800,000 saved, which sounds like a lot. But when I calculate that it needs to last potentially 30+ years, and I’m watching it go down every year, I lie awake at night worrying we’ll run out.” – Patricia, 66
8. Health Declines Will Happen Faster Than You Think
At retirement age, most people still feel relatively healthy and young. But the truth is that age-related health declines often accelerate in your 60s and 70s.
The timeline many retirees experience:
Ages 60-65: Still feel great! Energy is good. Mobility is fine. Maybe some minor aches and pains, but nothing major. This is when most people retire feeling invincible.
Ages 65-70: Things start changing. Knees hurt more. Back problems emerge. Energy levels decrease. Recovery from activity takes longer. Vision and hearing decline noticeably.
Ages 70-75: Health issues become more serious. Chronic conditions develop (arthritis, diabetes, heart disease, high blood pressure). Multiple medications become necessary. Travel becomes more difficult.
Ages 75-80: Significant health challenges for many. Mobility becomes limited. Balance issues and fall risks increase. Memory concerns emerge. Independence starts being questioned.
Ages 80+: For many, this is when significant help becomes necessary—whether from family, hired help, or assisted living facilities.
Obviously, this varies tremendously by individual. Some people are hiking mountains at 80. Others face serious health challenges at 60. Genetics, lifestyle, and luck all play roles.
Why this matters for retirement planning:
The “go-go, slow-go, no-go” years:
Go-go years (60s-early 70s): You’re healthy, active, and want to travel and pursue active hobbies. This is when you should do the physically demanding trips and activities.
Slow-go years (mid-70s-early 80s): Still active but with limitations. Travel becomes less ambitious. Activities are less strenuous. Health concerns increase.
No-go years (80s+): Significant health limitations. Travel is rare. Focus shifts to comfort and care.
The retirement planning mistake:
Many people save for retirement imagining they’ll travel extensively and be highly active throughout. But your most active retirement years are actually your earliest ones—often when you’re still adjusting and may not feel ready to spend money.
Then, when you’re finally ready to really enjoy retirement, your health may limit what you can do.
What successful retirees do:
Front-load experiences:
- Take the big trips early in retirement, not “someday”
- Pursue physically demanding hobbies while you can
- Don’t postpone travel or adventures waiting for the “perfect time”
Prioritize health:
- Exercise regularly (the single best predictor of healthy aging)
- Eat well
- Maintain social connections (social isolation accelerates decline)
- Stay mentally active
- Get regular medical checkups
Plan for decline:
- Make home modifications early (grab bars, better lighting, no-step entries)
- Have honest conversations about care wishes
- Research care options in your area
- Consider long-term care insurance
- Downsize before you have to
What retirees say: “We planned to take a big European trip ‘in a few years.’ Then my husband had a heart attack at 68. Now we wish we’d gone immediately when we retired. Don’t wait—go while you still can.” – Linda, 71
9. You’ll Question Whether You Retired Too Early (Or Too Late)
Retirement timing is agonizing, and second-guessing yourself is almost universal.
If you retire “early” (55-62):
You might worry:
- Did I leave too much money on the table?
- Could I have saved more if I’d worked longer?
- Will my savings actually last 35+ years?
- Am I too young to retire?
- What will I do with all this time?
- Will Social Security be reduced because I retired early?
Reality: Early retirement offers maximum health and energy for enjoying retirement. BUT financial stress can be significant if you haven’t saved adequately.
If you retire “on time” (63-65):
You might worry:
- Should I have retired sooner to enjoy better health?
- Did I waste my healthy years working?
- Could I have figured out the finances and left earlier?
Reality: This is the “traditional” retirement age, but health issues may already be emerging. You have Medicare coverage (at 65), which helps financially.
If you retire “late” (66+):
You might worry:
- Did I work too long?
- Did I sacrifice too many healthy years?
- Why didn’t I retire sooner?
- Will I even have time to enjoy retirement?
Reality: Your Social Security benefits are maximized, and you had extra years to save. BUT you’ve spent your most energetic years working.
The truth:
There’s no perfect retirement age. Every option involves trade-offs:
- Retire early = More time, less money, more financial anxiety
- Retire late = More money, less time, potentially reduced health
How to minimize regret:
Before retiring:
- Run the numbers thoroughly with a financial advisor
- Consider a trial retirement (take a leave of absence)
- Have a plan for how you’ll spend your time
- Discuss with spouse/family
- Check your gut feeling—if something feels off, listen to it
After retiring:
- Don’t look back and second-guess constantly
- Make peace with your decision
- Focus on making the most of retirement, whenever it started
- Adjust as needed (return to work, cut expenses, relocate, etc.)
What retirees say: “I retired at 58 and spent the first two years wondering if I left too early. Now at 65, I’m so grateful I retired when I did. My friends who are still working look exhausted, and I’ve had seven amazing years they didn’t get.” – Steven, 65
10. You Might Actually Miss Working (At Least Some Parts)
This is perhaps the biggest surprise: many retirees genuinely miss aspects of work, even if they hated their jobs.
What retirees miss:
The challenge: Work stretched your mind. You solved problems, made decisions, and used your expertise. Retirement can feel intellectually unstimulating by comparison.
The accomplishment: Completing projects and achieving goals felt satisfying. Retirement lacks built-in accomplishments and milestones.
The recognition: Being valued for your contributions felt good. In retirement, nobody recognizes your daily accomplishments (because there often aren’t any).
The expertise: You were good at your job. You were the expert people came to. That felt important. In retirement, your expertise becomes irrelevant—nobody needs it anymore.
The structure: As much as you hated the alarm clock, having a structured day created purpose and rhythm. Endless unstructured time can feel aimless.
The social interaction: Even difficult colleagues provided daily human connection. Retirement can be isolating.
Feeling needed: Work made you feel necessary. People depended on you. In retirement, you realize you’re actually quite dispensable, which stings.
How to recreate the positive aspects of work:
Challenge yourself:
- Learn new skills
- Take challenging classes
- Pursue complex hobbies
- Start a side business
Create accomplishments:
- Set goals (fitness, creative, educational)
- Track progress
- Celebrate achievements
Find recognition:
- Volunteer where you’re appreciated
- Join groups where you can contribute expertise
- Mentor others
Build structure:
- Create a daily routine
- Schedule regular activities
- Set weekly goals
- Use a planner
Stay social:
- Join clubs and organizations
- Take classes
- Volunteer
- Part-time work
What retirees say: “I thought I’d love having no responsibilities. Turns out, I miss being needed. I miss solving problems. I miss the feeling of doing something important. Now I volunteer, and it helps—but it’s not quite the same.” – David, 69