My Retirement Regrets
I never thought I’d say this, but I regret retiring early. If I had the choice to do it all over again, I’d keep working. While many other early retirees of my acquaintance seem fine with their decision, I’m just not. So here’s a list of all the reasons I wish I’d stayed in work – now I’m in this position, I want to help other people make an informed choice.
I Miss The Daily Routine
You don’t realize how important routine is until you no longer have it. Without work to anchor me, the days started to blur together. I thought I'd love sleeping in and lounging around, but it got old fast. What I should have done is ease into part-time work first instead of quitting cold turkey.
My Social Life Took A Hit
Most of my friends were still working, so suddenly I had all this time… and no one to spend it with. I didn’t realize how much I relied on office banter and lunch breaks for social interaction. If I had planned better, I’d have lined up some collaborative hobbies or social groups ahead of time.
Healthcare Costs Surprised Me
It’s an unfortunate fact of life that healthcare is expensive in America, so I wish I’d planned better. My private insurance ate into my savings faster than I expected. If I had a do-over, I’d work until at least 65 to make the transition into Medicare cheaper.
I Got Bored Fast
I imagined endless travel and leisure. But once I’d cleaned the garage and gone on a few trips, I started to feel... aimless. I didn’t have a plan beyond “don’t work.” I wish I’d made a bucket list of meaningful projects or goals before retiring instead of assuming fun would just happen.
I Missed The Paychecks
Even though I had savings, it was tough to watch my account balance go down every month with nothing coming in. I didn’t realize how reassuring that regular paycheck was. That’s another thing that made me wish I’d switched to part-time work first.
I Lost My Sense of Purpose
My job gave me a reason to get up and feel useful. Without it, I struggled to find that same fulfillment. Volunteer work helped, but it wasn’t the same. I should have worked harder during my work life to build an identity outside of it.
Travel Got Less Exciting
When you’re working, vacations are special. But when you’re retired, the thrill of travel wears off way quicker than you’d think. Airports and packing luggage became a chore. I didn’t expect to feel that way, but it happened.
Inflation Hit Harder Than I Expected
Prices climbed faster than I was expecting. Groceries, utilities, insurance – suddenly everything seemed to go up, but my income stayed where it was. I didn’t factor in how inflation could quietly chip away at my comfort - though it's the same for lots of people.
I Retired With a Mortgage
Big mistake. I thought I could manage the payments easily, but not having a salary made every bill feel so much worse. That monthly chunk of mortgage hurt. If I could redo it, I’d have waited until the mortgage was paid off to retire.
My Spouse Was Still Working
Turns out, retiring when your partner isn’t can be a lonely road. I was off having “freedom,” but they were still stuck in the daily grind of work. It led to tension, which is a horrible thing to experience in a marriage. I should have waited until both of us were ready to retire.
I Didn’t Know What to Do With Myself
Work had always been a huge part of my identity, and I never had time for major hobbies. When I quit, I didn’t know who I was anymore. I didn’t have any passions to fall back on, and I floundered. I really wish I’d explored new interests before retiring so I wouldn’t feel so lost afterward.
My Savings Weren’t Ready for the Long Haul
I thought I had enough saved, but retiring early stretched that timeline longer than expected. Suddenly, I was looking at 30 years of expenses instead of 20. That’s a lot of years for money to last. If I could go back, I’d work a few more years just to be safe.
I Felt Disconnected From the World
Work kept me engaged - news, fashion, celebrity gossip. After retiring, I felt like the world kept spinning and I just stepped off the ride entirely. Conversations felt harder to join. And like I said before, all my friends were still working, so they were harder to talk to.
I Didn’t Test-Drive Retirement First
I didn’t adhere to the old principle of “try before you buy”. I jumped in without trying it out. I should’ve taken a long vacation first just to see how I’d really handle all that free time. Turns out, I liked the idea of retirement more than the reality.
I Didn’t Factor in Adult Kids Needing Help
I assumed once the kids moved out, they’d be on their own. Wrong. Life threw curveballs their way - job losses, grandkids with health issues - and I ended up helping out financially. I was happy to do it, but if I had known that was coming, I’d have held off on retiring.
I Didn’t Know How to Say “No” Anymore
Once people found out I was retired, everyone suddenly needed something - rides, babysitting, errands. I ended up busier than when I was working, but with less control and crucially, less money. Sometimes I enjoyed it, but not always.
I Forgot About Longevity
I didn’t really think I’d live into my 90s - but I’m very healthy, so now I just might. Early retirement gave me more years of freedom but also more years of bills. I should’ve built a plan assuming I’ll live a long life, not just an average one.
I Thought Retirement Was a Destination
I treated retirement like the finish line of life, but it’s really just a new phase that needs a lot of planning, planning I just didn’t do. I thought the hard part was getting there, but I was wrong.
I Realized I Still Had More to Give
I left work thinking I was “done,” but soon realized I still had skills people needed. I missed mentoring and contributing. Early retirement felt like quitting while I still had gas in the tank, so to speak – and people I used to work with have even said that to me.
I Didn’t Plan for “Unretirement”
Eventually, I wanted to go back to work - just a little - but I was rusty and out of the loop. Employers weren’t exactly lining up to hire retirees. I didn’t stay up to date with my skills, and that’s arguably the biggest mistake I could have made.
