What if retirement didn’t mean waiting until 65, downsizing to a condo, and taking a couple of vacations each year?

For Robert and Jill from Our Retirement Reinvented, it meant something very different.

When I first interviewed them, they were preparing to retire early, sell nearly everything they owned, and begin traveling the world full-time. It was an ambitious plan—and one that probably sounds like a dream to more than a few Gen Xers.

This time, there was one big difference:

They actually did it.

Robert and Jill joined me from Lithuania, one of dozens of countries they’ve visited since beginning this adventure. I wanted to find out what happens when the retirement dream stops being a plan and becomes your everyday life.

And that distinction—between vacationing and living—became one of my favorite parts of our conversation.

After months of fast travel, they’re beginning to slow things down. Five-day stays are becoming ten days, and perhaps eventually two or three weeks. Hotels are giving way to apartments. Instead of trying to see everything, some days include grocery shopping, cooking dinner, doing laundry, or simply sitting on the couch watching TV.

In other words, travel has stopped being one long vacation.

This is their life.

We also talk about the financial reality of making this lifestyle work. Robert and Jill aren’t approaching retirement with an unlimited travel budget. They track their spending, make tradeoffs, and sometimes change plans when the numbers tell them to. They recently shared a much deeper breakdown of their actual spending on their own channel for anyone interested in the details. Pasted text

But some of my favorite parts of this conversation have nothing to do with money.

We talk about the people they’ve met around the world, being away from their sons, spending almost 24 hours a day together as a married couple, and what they’ve learned about themselves along the way. We also discuss the surprising amount of work involved in documenting all of this on YouTube while trying not to let creating videos get in the way of actually experiencing the adventure.

Robert and Jill aren’t suggesting everyone should sell their house and travel the world.

Neither am I.

But their story is a great reminder that retirement doesn’t have to look the way we’ve always assumed it would.

Sometimes financial independence isn’t really about retiring from something.

It’s about finally having the freedom to ask:

How do I actually want to live?

Watch my full conversation with Robert and Jill below, and then visit Our Retirement Reinvented to follow their continuing journey and see much more of the places, costs, challenges, and experiences we discuss.

What if it were 10? Or 5?

Would you keep working? Would you retire sooner? Would you finally take that trip or do something you’ve been saving for “someday”?

Here’s the uncomfortable part: none of us gets to know that number.

My wife and I spent years working toward a goal. By 2024, I wanted work to be optional. We made it, and I retired at 56.

We hit the ground running. We traveled, visited national parks, and started living the retirement we’d imagined. Then, just six months later, I learned I had a serious health issue.

I’m incredibly thankful to be retired, and I love the life we have today. But it’s not exactly the retirement I imagined.

The Other Retirement Number

We spend a lot of time preparing financially for retirement. We save, invest, calculate withdrawal rates, estimate Social Security and ask the big question:

Will my money last?

But there’s another question worth considering:

How long will my health last?

While working on this video, I was inspired by Dan Haylett of Humans vs Retirement and his episode “Your 12 Good Years.” Dan introduced me to the concept of Healthy Life Expectancy (HALE)—an estimate of how many years we can expect, on average, to live in good health.

The research didn’t convince me to retire early. I’d already done that.

Instead, it put data behind something I’ve felt for a very long time:

I feared running out of life more than I feared running out of money.

The Cost of Waiting

This isn’t an argument that everyone should retire at 56.

Maybe your number is 60. Maybe it’s 65 or later. And plenty of people remain active, adventurous and healthy well into their 70s and beyond.

I hope that’s your story.

The problem is that none of us gets to know in advance.

So absolutely plan financially for a long life. Save. Invest. Build the future you want.

But perhaps we should also live with the “what if?” in mind.

Don’t put everything you want from life on the other side of your retirement date.

Build your financial future. Just make sure you’re building a life along the way.

And ask yourself:

What are you waiting to do?

You can watch the full video above, and I also encourage you to check out Dan Haylett’s work at Humans vs Retirement. His “Your 12 Good Years” episode helped inspire this conversation.

What happens when a career you expected to continue for years suddenly ends?

Bruce spent more than 35 years with the same organization. He loved his work, valued the relationships he had built, and expected to work another five to seven years. Then an unexpected layoff changed everything.

In my conversation with Bruce from Porch Therapy, we talk about much more than losing a job. We talk about the anger and the “Why me?” that followed, the loss of identity that can come when a long career ends, and what it feels like to suddenly find yourself retired while your spouse is still working.

But what I enjoyed most about our conversation was hearing where Bruce is now.

YouTube became an unexpected form of therapy and connection. He’s volunteering, spending time with his family, traveling, and even rediscovering an old dream of writing—something perfectionism had kept him from pursuing for years.

Bruce’s story is one I think many Gen Xers will recognize. Sometimes we don’t get to choose exactly how or when our working years end. The bigger question may be:

What are we going to do with what comes next?

It’s been almost three years since my wife and I retired early at 56 and 57. The more distance I get from that decision, the more I find myself reflecting on a simple question:

What actually made it possible?

Looking back, there wasn’t a secret investment, a magic formula, or some special financial knowledge that we had access to. Our path was actually pretty simple.

Simple, of course, doesn’t mean easy.

In this video, I share the eight principles that I believe made the biggest difference for us—from believing early retirement was possible in the first place, to living below our means, saving and investing consistently, and eventually having the courage to take the leap.

I also share one of my favorite stories from my cycling days. For years, I thought joining an elite cycling team required a secret code. As it turns out, the code wasn’t nearly as important as I thought.

Financial independence is a lot like that.

There is no secret code. But you still have to put in the miles.

Watch the video below to see the simple path that helped us retire early—and hopefully find a few ideas that can help you along your own path.

Today I can, so today I will.

Retired at 56: This Made It Possible

What would your life look like if you had no debt? No car payment, no credit card balance, and eventually no mortgage?

My wife and I paid off our final debt in 2014. Looking back, becoming debt free was one of the decisions that ultimately helped make it possible for us to retire early at 56 and 57. It wasn’t just about saving interest—it lowered the amount of money we needed each month and gave us more freedom to make choices about our future.

In this video, I share our experience, talk about finding your WHY, and compare the debt strategies taught by Dave Ramsey and The Money Guy. I don’t believe there’s one perfect formula for everyone. Personal finance is personal—but having a plan and taking action can change what’s possible.

That’s plenty.

There’s also a strategic benefit I particularly like for you: your website becomes a library of davidnprogress, rather than another platform you have to constantly feed. Someone discovers one video through Google or YouTube, lands on your site, and can easily explore related videos on financial independence, early retirement, and living well after work.

I’d even organize the site around your three channel pillars: Achieving Financial Independence • Retiring Early • Living Your Best Life Now. That creates a very clean connection between the YouTube channel, podcast, and website.

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Not your investment portfolio.

Not your spending.

Not your retirement account.

Your life.

Every year, most of us spend time checking our finances. We look at our net worth, investment performance, and budget. Those things are important—but over the past year I’ve come to believe they’re only part of the picture.

I call the other part Net Life.

Net Worth is the sum of the dollars you’ve accumulated. Net Life is the richness of your lived experiences.

Whether you’re retired, approaching retirement, or still working toward financial independence, it’s easy to become so focused on building wealth that we forget to ask an equally important question:

Am I building the life I really want to live?

That’s why my wife and I set aside time each year to complete a Net Life Review. We each fill out the worksheet separately and then come together to talk about our answers. Those conversations have been some of the most valuable parts of our retirement.

In my latest YouTube video, I walk through the entire review with you. Think of it as a workshop rather than just another video. I’ll explain each section, share some of my own reflections, and encourage you to complete the review alongside me.

I’ve also made the Net Life Review Worksheet available as a free download so you can use it yourself.

If you’re married or have a partner, I highly recommend completing the worksheet separately before discussing it together. You may be surprised by what you learn—not just about yourself, but about each other.

Retirement isn’t just about growing your net worth.

It’s also about growing your Net Life.

👉 Watch the video here: https://youtu.be/8uQIReTu58A

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I hope this encourages you to pause, reflect, and intentionally build a life that’s as rich in experiences as it is in financial security. As I like to say:

Keep growing your Net Worth… but don’t forget to grow your Net Life.

I keep intending to write here as a blog in addition to my regular YouTube videos, but I have been unable to get on track for whatever reason. Here we go with a new goal to consistently add to this site.

What better place to start than to reflect upon my recent quintuple heart bypass surgery?

The heart issue came as quite a surprise. Yes, I was on blood pressure and cholesterol medication. The surprise came during my regularly scheduled annual health exam in May 2024. Honestly, I had a bit of a bad feeling going into the appointment, and I expressed this to the doctor when he arrived in the room.

Why?

I last visited this doctor in May of 2023, and my May-to-May journey was challenging. That Dr appointment led to a test that, in turn, became a cancer scare that lasted for several months.

Later, in September, I learned that my HR job at T-Mobile had been eliminated, and my termination from the company became official on December 4th.

I was excited about the layoff. It had always been my desire to leave due to position elimination. That is the best way to go, as you do so with a nice severance package to help with the transition. I was set to receive a nice package due to my 27 years with the organization.

Furthermore, ending full-time work in 2024 fell right into my long-time dream of having that be my year when work would be optional. It seemed like everything was going to plan. 

“Everyone has a plan until they get punched in the face” –Mike Tyson

What a great quote! It was a punch in the face to learn about my heart condition and then have to go through quintuple heart surgery. 

Two months have passed since the procedure, and my health journey has only begun. I am thankful it was discovered and grateful for all the years of financial planning that relieved the stress of being without work and with a giant medical crisis. 

The lesson. One I knew already but got a big reminder. 

We never know where life is going to take us. Live every day, knowing your time on this earth is limited. How you spend this time is entirely your own choice. 

David

Being Financially Independent gives you travel freedom

Our Utah trip was amazing as we visited three National Parks, two National Monuments, and one state park.

I had heard of Goblin Valley State Park and watched several videos about it. Like most things, you only understand once you are there. It was like we were visiting another planet with the hoodoos, the red dirt, and all the surrounding views.

The weather was a little crazy, with high winds and cold temperatures, and this just seemed to add to the sense of adventure. We spent a lot of time there walking around and exploring. You could spend several hours here if you wanted to.

I hope you take time to watch the video and enjoy!

I love to write. This issue for all these years is that I am unfortunately not very good at it. Take my ADD, throw in a bit of dyslexia and the result is a post full of typos and grammar errors.

It seems that I could spend hours writing and reviewing a post, but as soon as I hit publish–bam! Where did all the errors come from?

I eventually became so frustrated with my writing skills that I just plain gave up and moved on to making videos instead. Goodness, here comes another way for me to feel bad: now, not only do I have to worry about my grammar, but I also get to see how I look and sound.

Ugh

Of course, I could use AI and robots to write posts based on my suggestions, but that does not feel right. The words are okay, but the context and the feeling are not true to me.

I have used the free Grammarly tool for many years but decided to switch to the premium paid version after being laid off in September 2023. The difference has been amazing, with the AI serving as a writing coach to me in real-time.

Now, as I write, the Grammarly coach is there with every paragraph, and I can feel my confidence growing. It has grown so much that I have decided to add regular blogging back to my life routine.

Thanks, Grammarly, for your excellent tool. The $ 12-a-month premium plan has been priceless in helping me regain confidence in my long-time passion for writing and storytelling.

If you would like to try Grammarly and help me earn a discount, here is a link to learn more! https://www.grammarly.com/referrals/redeem?key=k6f3gjvfm7lsnwzs

For years, 59 1/2 was my target retirement year. Why? Well, it is common knowledge that we get access to our 401Ks starting then. Before 59 1/2, there was a significant tax penalty for withdrawals.

Yes and come to find out, no.

The penalty is there and does apply. However, as with many things in life, there is a loophole for those who know how to apply it correctly.

I learned about this option in 2017 when I first stumbled upon the FIRE (Financially, Independent, Retire, Early) movement. This was thanks to the ChooseFI podcast.

Amazing! Starting the year you turn 55, if you get laid off, fired, or leave your company for any reason, you can access and withdraw from your company-sponsored 401K plan with no early withdrawal penalty.

Amazing!

Learning this completely changed my mindset about when we could retire comfortably. It also changed our savings strategy since it compacted the timeframe for reaching a savings level that could sustain us until we reach Social Security and Medicare.

It just as importantly made the work optional date even closer. We were already on a coastFI trajectory and now I knew that starting the magic year of 55, our live choices would expand greatly.