What Nobody Tells You About Retirement: The Hardest Part Might Be the Month Before
When you think about retirement, you probably imagine sleeping in, traveling, spending more time with family, or finally tackling that project that's been sitting on your to-do list for years.
What you probably don't imagine is the weirdness that can exist right up until your last day at work.
In the first episode of our new series, What Nobody Tells You, our guest shared
something that really resonated with us.
The biggest surprise wasn't retirement itself.
It was the emotional roller coaster leading up to it.
She jokingly described it as a bit of a "mind fuck"—and honestly, we think a lot of people approaching retirement will understand exactly what she means.
After decades of working, making the decision to walk away can feel exciting...and strangely unsettling...all at the same time.
Even when you know you're financially ready.
Even when you're looking forward to it.
Even when it's exactly what you want.
The Last 30 Days Can Feel Surprisingly Emotional
For months—or even years—you've been planning for retirement.
Then suddenly it's real.
You start counting down your final meetings, your last commute, your last performance review, your last "Have a good weekend!" from coworkers.
You may start wondering:
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Am I making the right decision?
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Will I miss this more than I think?
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What if I'm retiring too soon?
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Why does this feel so emotional when I'm so excited?
Here's the encouraging part of our conversation:
Once retirement actually arrived...
She loved it.
No packed calendar.
No alarm clock dictating the day.
Lunch with friends.
Time to reconnect with people outside of work.
The freedom to simply enjoy life without immediately replacing one schedule with another.
Sometimes, after decades of living by someone else's calendar, having no schedule at all is exactly what you need.
Why Are We So Weird About Retirement?
One of the most interesting parts of our conversation wasn't about retirement.
It was about other people's reactions.
As soon as she started telling people she was retiring, everyone seemed to have an opinion.
Some people were genuinely excited.
Others immediately asked questions like:
"What are you going to do all day?"
"Aren't you too young?"
"I am so jealous!"
"Did you win the lottery?"
Most people don't mean any harm and I am a big believer in assuming positive intent.
But comments like these often say more about the speaker than the retiree.
Retirement (and really any life transition) has a funny way of making us think about our own lives, our own careers, and whether we're ready for that chapter ourselves.
That's why one of the best gifts we can give someone who's retiring is simple encouragement. Check out our Grief & Joy Retirement Collection and let us help you say just the right things to someone you know who is retiring.
What Should You Say to Someone Who's Retiring?
At Grief & Joy, we spend a lot of time talking about what to say during life's biggest transitions. Retirement is no different.
Instead of saying...
❌ "Did you win the lottery?"
❌ "I could never retire."
❌ "Must be nice."
❌ "You're too young."
❌ "What are you going to do all day?"
Try saying...
❤️ "Congratulations! What are you most looking forward to?"
❤️ "You've worked hard for this."
❤️ "I'm excited to see what's next for you."
❤️ "I hope you enjoy every minute."
❤️ "What's the first thing you plan to do?"
The best conversations aren't built on assumptions.
They're built on curiosity.
One Decision That Made Retirement Easier
Another takeaway from our conversation was the value of working with a financial advisor long before retirement.
Our guest didn't have to spend her final weeks wondering whether she could retire.
She already knew.
Because she and her husband had been planning for years with the guidance of a trusted advisor.
That preparation didn't just provide financial confidence.
It provided peace of mind.
Instead of stressing over spreadsheets during her final month of work, she could focus on celebrating the milestone she'd worked so hard to reach.
That's a reminder we think is worth sharing: retirement planning isn't just about growing your savings—it's about giving yourself confidence when the day finally arrives.
What Nobody Tells You
One of the reasons we created What Nobody Tells You is because every major life transition comes with experiences people rarely talk about.
Caregiving.
Reinvention after 50.
And so many more chapters that have practical decisions to make—but also have emotions, awkward conversations, unexpected joys, and lessons you usually only learn by living them.
Our hope is that by sharing real stories from real people, you'll feel a little more prepared for whatever chapter comes next.
Watch the Full Conversation
If you're approaching retirement—or if someone you love is—you won't find investment advice or retirement calculators in this conversation.
What you'll find is something just as valuable:
An honest discussion about what retirement actually feels like before, during, and after that last day at work.
Because sometimes the things nobody tells you are exactly the things you need to hear.
Watch the full episode of What Nobody Tells You About Retirement and join the conversation. This isn't just a one and done discussionn on retirement. We will be checking back periodically with our guest to follow along her retirement journey.
And we'd love to hear from you in the comments:
What's the best thing someone said to you when you retired—or what do you wish they had said instead?
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