Have a Moment of Retirement Remix: Trailblazing as an Outlier

A self-indulgent guide to trailblazing retirement by embracing growth, strategic risks, and avoiding the life tax.

Hey, Braveheart! Ready to flex those courage muscles? Let Koffeemocha be your trusty partner, adding a shot of fun and flavor to your life's epic adventure!

After a year-long excursion to celebrate my early retirement in New York City, I'm back in Pleasanton for a Labor Day weekend break and to assess where I am on this journey, having seen many others in between. For some, it's a joyous plunge into the golden years of golf, gardening and grandchildren. For others, it's a dance of strategic tax planning and finding the nearest low-cost haven so that retirement dollars can be used for extravagant travel. And then there are the outliers; those of us who see retirement not as an endpoint but as a remix, a reinvention, a grand opportunity to forge new paths and build inner growth and capacity. That's where I come in.

Welcome to Retirement Remix: Outlier Edition

Let's start with a confession: I'm a retirement outlier (outlier, the statistical term I borrowed from my recent review and interest in data science with a talented graduate student).

Yes, I could have taken the road less traveled to a quiet, predictable life, relocated to some sunny tax haven where the cost of living is low and my golf game could finally flourish. 

Instead, I chose Pilates to flex my muscles instead of a golf swing in the vibrant, tax-heavy metropolis of New York City.

Because I believe that retirement can be a remix phase of life, where the focus shifts from playing it safe to strategic risk-taking, growth and, most importantly, avoiding what I called "life tax".

Now, you may be wondering, "What in the world is a life tax?"

Allow me to explain. 

The life tax, or tax on life, is the cost of living a life that sacrifices spontaneity, passion, and connection in exchange for financial gain or savings. It's what you pay when you move away from your family and grandchildren to save on taxes, only to find that you've traded those precious moments for extra dollars. Believe me, such a tax is a bill you don't want to pay, but you're subconsciously paying...

So how does one move from a traditional retirement mindset to becoming an outlier, a trailblazer in the art of retirement remix? 

Buckle up, Koffeemocha time.

Chapter 1: The Birth of the Outlier Mindset

Let's rewind to the beginning of my retirement journey.

Picture it: the suburban tranquility of Silicon Valley, the California sun setting behind the trees in my backyard, casting a warm, golden glow. It's the kind of setting that makes you want to kick back, relax, and watch the world go by. But as I sat in my chair and looked out over Pleasanton Ridge, feeling this warmth and serenity, I couldn't help but feel that something was missing.

Now, after more than a year of moving between the tranquility of the suburbs and the bustling energy of the city in my early retirement. This often back and forth has profoundly influenced my belief that the essence of life is the freedom to move between choices, to be here and there as you please. 

Why should retirement be any different?

That's when it hit me: retirement doesn't have to be about settling down. It can be a remix, a time to take the best parts of life and mix them together to create something new. And so the outlier mindset was born. I wasn't going to follow the typical retirement script. No, I wanted to write my own story, a story of growth, adventure, and, yes, a little risk.

Chapter 2: Strategic Risk-Taking

Now, let's talk about risk. I know, I know - retirement is supposed to be the time when you finally stop taking risks, right?

Wrong! 

If anything, IMHO, retirement is the perfect time to take strategic risks. The kind that can lead to tremendous growth, both personally and financially.

But here's the catch: not all risks are created equal. I'm not advocating betting your retirement savings on the next big cryptocurrency or trying to climb Mount Everest at 70... No, I'm talking about calculated risks; those that align with your goals and values.

For me, one of those risks is staying in New York City. Sure, the cost of living is high, and the taxes are, well, let's just say they're less than friendly. 

But the trade-off? 

An enriched life of culture, opportunity, and connection. I'm a city boy at heart, and the energy of the city feeds my soul in a way that no tax haven ever could.

So how do you identify the right risks for your retirement remix? Start by asking yourself these questions:

• What truly matters to you in this stage of life?

• What are you willing to sacrifice to achieve your goals?

• What risks align with your long-term vision for retirement?

Once you answer these questions, you'll be well on your way to taking the kinds of risks that lead to growth, not setbacks.

Chapter 3: Investing in the Cloud

Now, let's talk about investing. No, I'm not talking about your 401(k) or IRA, although those are important. I'm talking about investing in the cloud; both literally and figuratively.

Let's start with the literal cloud. As someone who has spent years in the technology industry, I've seen firsthand the power of cloud computing. It's not a buzzword; it's happening now. And retirement is the perfect time to change my role from back-end engineer to front-end consumer. Whether it's tracking new cloud-based technologies, or exploring data analytics, there's no limit to what you can accomplish. 

But beyond the digital cloud, there's the figurative cloud; the space and time where you invest in your inner growth and capacity. This is where the real magic of retirement remix happens. Take time to explore new interests, deepen your knowledge, and expand your horizons. Whether it's through writing, mentoring, or taking up new hobbies, this investment in yourself will pay dividends beyond what the financial market can offer.

For me, that investment takes the form of writing, connecting with young readers, and helping others with career planning. It's about building something meaningful beyond the financial. It's about leaving a legacy; not in the old, stuffy sense of the word, but in the sense of creating something that resonates with who you are and what you stand for.

Chapter 4: Avoiding the Life Tax

The Life Tax. We've touched on it before, but it's worth exploring a bit more. The life tax is what you pay when you choose convenience, security, or financial savings over what really matters. It's the price of not being able to spontaneously visit your family or grandchildren because you moved to a low-cost area. It's the cost of living a life that's comfortable but not fulfilling.

The key to avoiding the life tax is to stay true to your values, even if it means paying a little more financially. For me, that means staying in New York, where I can be close to my family, soak up the city's vibrancy, and stay connected to the people and places that matter most to me. 

It's a trade-off, yes, but one I'm more than willing to make.

So how do you avoid the life tax in your retirement remix? It starts with understanding what is really important to you. Is it family? Connection? Adventure? Whatever it is, make it a priority, even if it means paying a little more financially. Because in the end, the life tax is far more costly than any income tax ever could be.

Chapter 5: The Outlier’s Guide to a Fulfilling Retirement

Now that we’ve covered the basics, let’s wrap things up with some practical tips for embracing the outlier mentality I’ve developed and followed,

• Embrace Change: Retirement is a time of transition, and it’s okay to feel a bit uncertain. Embrace the change and see it as an opportunity to reinvent yourself.

• Take Calculated Risks: Whether it’s moving to a new city, or pursuing a new hobby, don’t be afraid to take risks. Just make sure they’re aligned with your long-term goals.

• Invest in Yourself: This is your time to grow, learn and expand your horizons. Whether it’s travel or personal projects, make sure you invest in your inner growth and capacity.

• Stay Connected: Don’t let retirement isolate you. Stay connected to your family, friends, and community. Make sure you’re nurturing your relationships.

• Avoid the Life Tax: Prioritize what truly matters to you, even if it means paying a bit more financially. The life tax is far more costly in the long run.

• Have Fun: Retirement is supposed to be fun! Don’t take yourself too seriously. Find joy in the little things.

Conclusion: Trailblazing Your Retirement Remix

Ultimately, being an outlier in retirement isn’t about bucking the norm for the sake of bucking the norm. It’s about creating a life that’s true to who you are; a life rich in meaning, growth, and connection.

By adopting the retirement remix approach, you can move into this new phase with a sense of purpose and excitement.

So here’s to the outliers, the trailblazers, the ones who refuse to play it safe.

May your retirement be as unique and fulfilling as you are. And remember, the real reward isn’t just avoiding the life tax; it’s living a life that's truly yours. Cheers to that!