The story, Rolling into Retirement Like a Boss, follows a friend group of women in their late 50s as they revisit their roller-skating glory days to celebrate friendship and to prove that age is just a number.
Lynn tightened the laces on her old roller skates, the kind with bright orange wheels and neon rainbow laces. She couldn’t help but grin as she glanced at the other women beside her—her ride-or-die crew from back in the day. They’d spent every Friday night in the ‘70s and ‘80s skating around the rink, crushing on the DJ, and perfecting their backward crossovers. Now, they were preparing to roll into those traditional retirement years with the same energy, and of course, the same sass.
Jill, the wild one with a head full of silver curls, gave a mock-serious nod. “You know, if we can still do this without breaking a hip, we’re officially winning at this mid-life thing.”
“Mid-life?” questioned Lynn, “Do you expect to live to 116 Jill?”
“You’re right,” Jill said. “Damn, we’re a little older than I thought.”
“I’m more worried about getting off the rink than getting on,” chimed in Tina, winking. “I don’t remember how to stop.”
“I’m not even sure my legs are going to hold up,” quipped Cheryl.
The rink was just like they remembered it—disco ball shimmering above, classic hits blaring over the speakers. “Stayin’ Alive” was playing as they took to the floor, the irony of the song choice not lost on any of them.
The one main difference was this was 50-plus night at the rink. The other skaters looked a little older than they remembered.
The trio formed a line, hands linked, rolling slowly at first. It was like muscle memory kicked in, and suddenly, they were skating with the confidence of their 20-year-old selves. Sure, there were a few wobbles—especially when someone tried to attempt a spin—but the laughter was contagious.
“See gals, this is what rolling into retirement will look like?” Lynn yelled over the music, half skating, half dancing to a Donna Summer song.
Jill, always the daredevil, went for a full twirl. “We may have a few more wrinkles, but we’ve still got moves, baby! We’re just getting started…on our second act. And it’s gonna be disco-tastic!”
As they circled the rink, the young skate guards were seemingly enjoying watching all these 50-plus women and men, defying the stereotype of what “old age” was supposed to look like. No sitting on a porch knitting here—these ladies were rolling into the next phase of their lives like boss babes.
The DJ, sensing the vibe, switched the track to ABBA’s “Dancing Queen,” and the women erupted in cheers. They glided along, arms raised in celebration, feeling the decades melt away.
“Let’s keep doing this ladies, it’s so fun.” Tina blurted out as she tried a little backwards skating. “Who said we have to slow down when we decide to retire?”
Jill chimed in, “It’s about knowing when to hit the rink, when to crank the ABBA, and when to enjoy the ride. And we’re going to rock it…maybe.”
With that, they rolled off the floor, breathless and beaming, high-fiving each other like they’d just conquered the world. And maybe they had—because no matter how many years had passed, they knew one thing for sure: they were still skating through life like the queens they’d always been.
As the ladies kicked off their skates and settled into a booth, sipping on some well-deserved adult beverages, the conversation turned to more than just reminiscing about their glory days.
“Alright, queens,” Cheryl the ever practical (and cautious one) said, adjusting her reading glasses. “We’ve mastered the rink, now let’s talk about our slow roll into retirement. We’ve got Lynn the retirement expert here. Let’s pick her brain. What is y’alls plan? I’m worried about retirement?”
“I don’t even know if I can retire,” added Tina. “I have no idea how much money I’ll need and if my nest egg is enough.”
“Well, I’m definitely ready to give my boss the boot, snickered Jill, “And I’ll do it with these bad-ass skates on too!”
“Yeah and then you’ll fall on your ass,” retorted Lynn.
‘Nope, I’ll roll right over him and never look back. And then I’ll roll-over my 401k and live happily ever after. Ha.” Jill added as she laughed and choked on her sip of hard cider.
“That’s a good one.”
The women all giggled.
“I for one, don’t have plans to retire ladies. I love what I do, and I don’t have a boss to roll over,” added Lynn smirking. “But, I can answer any questions you all have and get you ‘rolling’ in the right direction.”
Cheryl, ever the practical one, nodded. “You know, the key to a smooth retirement is all about finding your balance—just like on the rink. How do we strike a balance between our health, our wealth and our happiness?”
“Oooo, someone has been listening to my podcast and YouTube videos,” quipped Lynn.
Cheryl gave Lynn a wink.
“let’s hear some suggestions, Lynn,” Jill piped in.
Tina added, “Yeah, I don’t even know where to start. It’s freaking overwhelming.”
Well, let’s refill our drinks and keep this conversation rolling. I got you my BFFs,” Lynn began.”
“Yeah and all the other over 50 women like us,” added Cheryl, with a high-five to Lynn.
“Okay, ladies, here goes. A few suggestions for ‘cruising’ safely and happily into retirement or whatever the hell you want to call it.”
First, Keep Moving, But Know Your Limits
- “We might not be doing double axels, but staying active is essential. Walking, swimming, roller skating, lifting weights, yoga and eating right. We need to focus on our physical health. And don’t forget about mental health. Meditation is awesome.
Second, Review Your Retirement Finances & Have a Plan
- “Before you give your boss the boot with those skates Jill, make sure you’ve checked your wheels—uh, I mean, your finances. It’s important to know where you stand with savings, investments, and stuff like your retirement income and Social Security. You also need to make sure you have a plan for health insurance, maybe long-term care protection and estate planning. Jill, you need to make sure you and Bill have a will and trust for the kids. Tina, your house is paid off, you can leverage your home equity in retirement. And Cheryl, you probably could really benefit from tax planning. You could be subject to IRMAA in retirement. A little planning now means you can glide smoothly later ladies. Planning is numero uno. Those who plan live a better, more intentional and financially secure retirement.
Third, Stay Social, But Skip the Drama
- “Remember those Friday nights when drama seemed to follow us everywhere…even here at the rink?” Lynn laughed. “In retirement, it’s all about surrounding yourself with positive vibes. Stay connected with friends (like us) and family, join clubs, or find a new hobby. Life is way more fun when you’ve got a crew to roll with, and you’ll live longer.
Fourth, Embrace New Adventures—Safely
- “We may not be jumping at the rock quarries anymore, but that doesn’t mean we can’t try new things,” Lynn added with a grin. “Just make sure to use some common sense. Whether it’s traveling, picking up a new hobby, or even just exploring your own neighborhood, keep safety in mind—especially if you’re going solo. And don’t fall for someone calling you and trying to scam you. Senior scams are BIG business and so many people fall prey to it.
Fifth, Health Check-Ups: Your Tune-Up
- “We always made sure our skates were in good shape, right?” Lynn pointed out. “Same goes for our health. Regular check-ups with your doctor, eye exams, breast exams, all those shots for senior, and staying on top of any medications will keep you rolling along without unexpected bumps.”
Sixth, Budget for Fun
- “Just because you may be retired doesn’t mean we’re done having fun,” Lynn added. “Make sure your budget includes room for little luxuries—whether that’s a trip, a spa day, or just a night out with the girls (wink, wink). We’ve earned it!”
Seventh, Focus on Your Purpose
- “Just because we’re closing in on those traditional retirement years doesn’t mean we have to “retire” in the traditional sense. We can define a new purpose for our lives. There’s lots of research on purpose and retirement. Research consistently shows that having a sense of purpose in retirement can significantly enhance both mental and physical well-being.”
“Wow, that’s an awesome list, Lynn. Thank you so much,” Tina said giving Lynn a big hug.
“You’re welcome,” added Lynn. “I know it feels like a lot, but we got this ladies and I’m always here for you. We can be HappiHER, HealthiHER and WealthiHER and I’m here to help you Get HER Done.
As the group of friends gathered their things, Jill stood up, wobbling slightly on her feet. “And if you do take a tumble—whether it’s skating or life—just remember, the trick is getting back up and laughing about it. We’ve got this, ladies. Retirement? Phhh. We’re rolling into it like boss babes!”
That’s the spirit! Rolling into retirement with confidence and a plan (and a little bit of humor) makes all the difference. Those tips feel just like strapping on your roller skates—if you keep your balance, plan ahead, and have fun along the way, you’re bound to enjoy the ride!
How Do I Get Started Planning for Retirement?
Getting started on rolling into retirement smoothly is a lot like prepping for a great night at the rink. Here’s your step-by-step guide:
- Assess Your Current Situation
- Finances First: Review your savings, pensions, and Social Security benefits. Knowing what you have to work with will give you peace of mind. Use retirement calculators like the Her Retirement Readiness software platform to help you.
- Health Check: Schedule a full health review with your doctor. Knowing where you stand health-wise will help you plan for activities that suit you now and down the road.
- Set Clear Retirement Goals
- What do you want retirement to look like? Travel, hobbies, time with family? Write it down. Knowing your goals will help you prioritize and budget accordingly. The Her Retirement Readiness software has an entire module to help you envision your retirement.
- Create a Retirement Budget
- Track your current expenses and see how they may change once you retire. Be sure to budget for both essentials (housing, healthcare) and fun stuff (travel, hobbies). Include a cushion for unexpected expenses. Knowing your cash flow (income minus expenses) is essential. The Her Retirement Readiness software has a Smarter Spending Tracking Tool to help you know and track your cash flow, now and in retirement.
- Stay Active and Engaged
- Find physical activities you enjoy, whether it’s walking, swimming, or even roller skating every now and then. Staying active helps keep your body and mind sharp.
- Look into local clubs or classes where you can meet new people or learn something new—like dancing, cooking, or gardening. It’s all about keeping life exciting!
- Start Organizing Your Paperwork
- Make sure your will, power of attorney, and any advance directives are in order. It’s a small step now that gives you huge peace of mind later. Check out the Her Retirement Personal Info & Emergency Planner at: www.HerEmergencyPlanner.com
- Organize any retirement accounts and insurance paperwork so it’s easy to access when you need it.
- Practice Letting Go of Work Stress
- If you’re still working, start easing into a mindset where work doesn’t dominate. Maybe reduce hours or take on more flexible roles. Begin mentally transitioning to what life will look like when work isn’t the center.
- Find Joy in the Little Things
- Treat yourself now and then. Whether it’s an afternoon spent with friends or picking up that old roller-skating hobby again, find ways to inject joy into your routine.
Starting on this retirement journey doesn’t have to be overwhelming. Just lace up, take it step by step, and before you know it, you’ll be gliding into your second half with confidence! If you need help rolling into retirement, reach out to Lynn at: lynnt@herretirement.com. I got you, and I’ll even go roller skating with you.