8 evening habits of boomers who consistently win at life

Farley Ledgerwood by Farley Ledgerwood | March 20, 2025, 9:54 pm

If a boomer is up late at night, you might assume they’re binge-watching their favorite TV show. If they’re early to bed, you might think it’s because they’re tired.

But that’s just scratching the surface.

In reality, the habits of successful boomers are more nuanced and thoughtfully planned. They’ve mastered the art of evening routines that set them up for a win, day after day.

I’ve identified 8 common evening habits that separate these winning boomers from the rest. And I’ll let you in on the secret – it’s not all about going to bed early or staying up late.

Let’s dive in and explore these 8 habits.

1) They prioritize winding down

Life is a whirlwind of chaos and responsibilities.

It’s no different for boomers who are consistently winning at life. However, they have a secret weapon: a dedicated winding down period each evening.

This isn’t just about turning off the TV or putting down their phone. It’s about creating a mental and emotional shift from the busyness of the day to the tranquility of the night.

They use various techniques to achieve this state of calm – reading, meditating, listening to soothing music, or simply sitting in silence and reflecting on their day.

The goal here isn’t to simply pass time before bed but to actively transition into a peaceful state of mind, preparing for a restful night’s sleep.

This habit not only promotes better sleep but also reduces stress and anxiety, setting them up for success the next day.

And that’s just one of the ways they consistently win at life. 

2) They plan for the next day

Now, I know what you’re thinking – planning sounds like work, and evenings are for relaxing, right?

Well, let me share a little secret from my own life.

I’ve always been a fan of to-do lists. But I used to make them in the morning, and it would often leave me feeling overwhelmed. Then, I started doing what successful boomers do – planning my next day the night before.

Each evening, I sit down for about ten minutes and list out the things I need to accomplish the next day. It’s not just about work tasks – it includes personal errands, workout time, and even moments for relaxation.

This little shift in routine has made such a difference. When I wake up, I already know what my day looks like. It reduces stress and makes my mornings much smoother.

So remember, a little bit of evening planning can go a long way in setting you up for success.

3) They nurture their relationships

Evenings are a prime time for boomers winning at life to invest in their relationships.

And this isn’t mere speculation. Research has shown that strong interpersonal relationships contribute to overall happiness, mental health, and even longevity.

These boomers might spend their evening hours catching up with a friend over the phone, enjoying quality time with their partner, or even playing with their grandkids.

And here’s the beauty of it – these interactions aren’t just fulfilling on an emotional level, they also provide a mental break from the stresses of daily life.

Next time you’re deciding how to spend your evening hours, remember that cultivating relationships is not just about socializing – it’s a key component of a fulfilling and successful life.

4) They engage in mindful activities

Mindfulness might sound like a buzzword, but it’s a big part of the evening routine for boomers who consistently win at life.

Mindful activities could be anything from painting to gardening, or even doing a puzzle. It’s not so much about what they do, but how they do it.

When engaging in these activities, they’re not just passing time. They’re fully present, focusing on the task at hand and letting go of any worries or thoughts about the past or future.

This mindfulness not only helps them relax and unwind after a long day, but it also boosts their creativity and problem-solving skills.

An evening habit as simple as spending time on a hobby can have profound benefits when done mindfully.

5) They disconnect from technology

Now, don’t get me wrong. I’m not against technology. In fact, I rely on it for a lot of things in my life, from work to staying connected with my loved ones.

But here’s something I learned from boomers who consistently win at life – there’s immense value in disconnecting from technology in the evening.

Ever since I started putting away my devices an hour or two before bed, I’ve noticed a significant improvement in both the quality of my sleep and my overall mood.

I’m more relaxed, less stressed, and I wake up feeling more refreshed.

If you’re looking to win at life like these boomers, try unplugging from your devices in the evening. Trust me, it’s a game-changer.

6) They keep learning

Evenings are often associated with relaxation and entertainment. But for the boomers who consistently win at life, it’s also a time for learning.

Yes, you read that right – learning. They might be retired from their jobs, but they never retire from learning.

They spend their evenings diving into a new book, taking an online course, or even tuning into a podcast on a topic that piques their interest.

And it’s not about being productive all the time. Instead, it’s about feeding their curiosity, expanding their knowledge, and keeping their mind active and engaged.

Just because the sun sets, it doesn’t mean your pursuit of knowledge should too.

7) They practice gratitude

It’s easy to get caught up in the hustle and bustle of life and forget to appreciate the good things we have.

But boomers who consistently win at life know the importance of gratitude. They make it a habit to reflect on the positive aspects of their day each evening.

Whether it’s jotting down a few things they’re grateful for in a journal, or simply taking a moment to acknowledge their blessings internally, this practice of gratitude helps them maintain a positive outlook on life.

It’s a simple habit, but it can make a huge difference in your overall happiness and satisfaction. So why not give it a try?

8) They prioritize rest

At the end of the day, literally and metaphorically, the most critical habit of boomers who consistently win at life is prioritizing rest.

They understand that adequate sleep is not a luxury, but a necessity for maintaining physical health, emotional well-being, and cognitive function.

They design their evening routines to promote restful sleep – whether it’s sticking to a consistent bedtime, creating a serene sleep environment, or avoiding caffeine and heavy meals close to bedtime.

Because no matter how productive or fulfilling their day has been, they know everything hinges on getting a good night’s sleep.

And that’s perhaps the ultimate secret to consistently winning at life.

Reflecting on the journey

If you’ve made it this far, hopefully, you have a newfound appreciation for the evening habits of boomers who consistently win at life.

These habits aren’t about rigid schedules or high productivity. Instead, they are about creating a space for self-reflection, growth, and peace.

They remind us that success isn’t merely about the accomplishments we amass but also about the habits we cultivate, the relationships we nurture, and the peace we find within ourselves.

As Lao Tzu once said, “Silence is a source of great strength.” And these boomers have harnessed that strength in their evening routines, turning their nights into a source of calm and renewal.

As you move forward, remember that evenings are not just the end of a day but the beginning of a restful night and a successful tomorrow. Reflect on this wisdom and consider how you can incorporate these habits into your own life.

Because, after all, who doesn’t want to consistently win at life?