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Blog Post: Breaking Free – My Retirement Awakening

Hey everybody!
Thanks for stopping by my Blog/Vlog/YouTube hub. This is my very first post, and I’m glad you found it.

I’m a DIY retirement guy. I spent most of my career on Wall Street, working in software integration for investment firms—the same firms that manage our retirement money. I know… ironic, right?

After nearly 15 years grinding away, helping clients with complex integration projects, I reached a turning point. I realized I was no longer fulfilled. As much as I loved technology and software, the passion had faded. I felt stuck—burnt out, frustrated, and disconnected from my purpose.

So I started asking deeper questions:
What am I doing? What do I truly want? Why does this feel so wrong now?

That soul-searching led me to counseling and honest self-reflection. I discovered that my core desire wasn’t more success or a better job—it was freedom.

Freedom from the rat race.
Freedom from endless bills.
Freedom from the post-COVID price spikes and uncertainty.

If you live in the U.S., you already know—freedom is a privilege. We’re incredibly fortunate to have access to opportunity and wealth that far exceeds the global average. But that freedom often comes at a cost—to our health, mindset, and time. And if you’re not constantly keeping pace, you risk being left behind.

A Personal Loss That Sparked a Deeper Realization

Around this time, I also lost my favorite cat, Sammi. He was one of our four cats—and definitely the smartest. When he disappeared, I was devastated. If you’ve ever had a pet, you know the anxiety and heartbreak that comes with losing them.

Our family went all in to find him. We made flyers, knocked on doors, followed advice like spreading my scent in the area (yes, it’s a thing), and even accidentally caught a feral cat thinking it was him. After 27 long days, Sammi came back!

And here’s what I realized from Sammi’s adventure:
He just wanted to be free.
To roam. To explore. To be his natural self.

Aren’t we all a little like Sammi?
Humans weren’t designed to sit at desks under fluorescent lights, constantly worried about layoffs or inflation. If we had just the basics—water, shelter, food—I believe most of us would choose freedom and exploration over the grind.


Why Wait Until 65?

Why do we have to work until 65? Who made that rule?

Retiring early isn’t a flaw—it’s a choice. But society doesn’t always support that choice. The government wants us to work longer to keep Social Security and Medicare funded. The reality is, they’re running out of money—and the easiest way to refill those coffers is by taxing our untapped 401(k)s and retirement accounts.

Here are some eye-opening stats:

  • In 2020, 29 million Boomers retired—up from 26 million the year before.
  • Through 2027, 4.1 million Americans will turn 65 every year.
    (Sources: cogentinfo.com, Investopedia)

With so many retiring, and fewer workers paying into the system, where will the money come from? One guess: your pre-tax retirement savings.


A Quick Look at U.S. Tax Rates

There’s a common belief that we’ll be in a lower tax bracket in retirement—but is that guaranteed? What if rates rise? History suggests they might:

PeriodTop Marginal Tax Rate
1918~77% (WWI era)
1944–4594% (highest ever, WWII)
1952–63~92%
1982–8650% (Reagan cuts)
1993–200039.6% (Clinton era)
2018–202537% (Trump’s tax cuts)

We’ve seen massive swings before. It’s naïve to think rates will stay low forever. That’s why it’s crucial to build a smart drawdown strategy.


Smart Moves Before and During Retirement

Here’s a basic order of operations for your retirement withdrawals:

  1. Brokerage/Cash Accounts
  2. Convert pre-tax accounts to Roth gradually
  3. Use Roth funds last

Also consider:

  • Roth IRAs – Tax-free growth and withdrawals in retirement.
  • IUL (Indexed Universal Life) – Acts like a Roth + annuity with death and long-term care benefits.
  • HSAs (Health Savings Accounts) – Triple tax-advantaged and flexible after age 65.

My Vision of Retirement

My retirement vision isn’t about luxury. It’s about freedom, simplicity, and purpose. I’m planning to retire abroad in Southeast Asia—likely Thailand or Vietnam—where the cost of living is reasonable and the lifestyle is peaceful and inviting.

I don’t need fast cars or a big house. I want sunshine, a modest home, good food, and a life filled with meaningful experiences. I’m a warm-weather person. If I could go full tropical and live in shorts year-round, I’d be in heaven.


Your Turn: Envision Your Freedom

Start now. Picture your retirement—what does it look like?
What lights you up? What do you want to do more of?

If you don’t know yet, that’s okay. But don’t wait until someone else defines it for you. Take small steps. Try something new. For me, blogging and making YouTube videos has been an amazing creative outlet—and it might be for you too.

I’m writing this from my home office, words flowing like water. That tells me I’ve found my thing. My joy. My freedom.

Thanks for being here—stay tuned for the next post where I’ll dive into mindset and setting up your ideal retirement lifestyle.

Let’s make this journey together. You’re not alone.

Check out my YouTube Channel where I talk about this in more detail. http://Is it Time to take the plunge?

See you on the waves. 🌊
—Vincent

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