Things I Wish I Knew Before Retiring: Hard-Won Wisdom from Real Retirees

The most common surprise: The emotional/identity challenges are harder than the financial ones.

• **"I didn't expect to feel so lost."** Without a job title, who are you? This hits hard.
• **"I should have started hobbies earlier."** Building interests while still working is easier.
• **"I underestimated how much I'd miss work."** Even jobs you complained about provide purpose.
• **"Retirement isn't a permanent vacation."** The vacation feeling fades after a few months.
• **"I needed more than relaxation."** Humans need purpose, challenge, and achievement.
• **"It took longer than expected to adjust."** Give yourself 12-18 months, not 12-18 weeks.

Retirement changes relationships in ways people don't anticipate.

• **"24/7 with my spouse is harder than expected."** Even great marriages are tested.
• **"We needed separate activities."** Individual hobbies and friendships are essential.
• **"Work friends disappeared."** The daily relationships end when the daily contact does.
• **"Making new friends is hard."** It takes intentional effort, not passive waiting.
• **"My single friends still work."** Your schedule won't match friends who haven't retired.
• **"I didn't anticipate the role renegotiation."** Household responsibilities need to be discussed, not assumed.

Open-ended time sounds wonderful until it becomes aimless drifting.

• **"I needed more structure than I thought."** Total freedom becomes disorienting.
• **"Days blurred together."** Without markers, time loses shape.
• **"I should have planned activities in advance."** Don't assume you'll "figure it out."
• **"Boredom hit faster than expected."** After 2-3 months, doing nothing got old.
• **"I wasted my first year."** Some retirees regret not being more intentional earlier.
• **"Weekly anchors helped."** Regular Tuesday tennis, Thursday volunteering, etc.

Financial surprises - both positive and negative.

• **"Spending savings felt wrong."** Decades of saving made spending psychologically hard.
• **"Healthcare costs were higher than expected."** Especially the pre-Medicare gap (62-65).
• **"I didn't need as much as I thought."** Many retirees spend less than projected.
• **"Taxes surprised me."** Social Security taxation, RMDs, Roth conversions - get help.
• **"I should have done Roth conversions earlier."** The years right after retiring, before SS and RMDs.
• **"Market drops feel different when retired."** No paycheck to wait out the recovery.

Retirement affects health in unexpected ways.

• **"I gained weight without walking at work."** Those steps added up more than you realize.
• **"I needed scheduled exercise."** It doesn't happen automatically like commute-walking did.
• **"Mental health mattered more than physical."** Depression and anxiety were bigger issues than expected.
• **"Sleep schedule got weird."** Without morning commitments, sleep drifts.
• **"My best years are NOW."** Don't defer enjoyment - health declines gradually.
• **"Routine keeps me healthy."** Structure supports physical and mental health.