Making Dreams a Reality – New 10 Year Vision Letter



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Written: September 4, 2033

Sent back in time to: September 30, 2023

Dear Dom,

As the great Jim Rohn would say: “If you don’t plan your future, somebody else will. And you know what they have planned for you? Not much!” Adopting your own Manifest Destiny philosophy has played an instrumental role in making your dreams a reality. Unlike the American Manifest Destiny, this has nothing to do with any superiority but instead is all about taking the helm to steer YOUR life in the direction YOU want to go. It’s about planning and executing a plan to live on your terms. Don’t just dream, do something!

Planning is your superpower! But just like knowledge, it’s wasted without action. The fortune is in the follow-through. Your ability to take massive action without getting stuck in analysis paralysis is your TRUE superpower. At the end of the day, planning is just dreaming; it’s action that turns dreams into reality. And boy, do you take MASSIVE ACTION!

We live in an uncertain world where nothing is ever guaranteed. No plan will ever go 100% as laid out. Yet, there is an undeniable force that is at work to break through obstacles when you pair a good plan with consistent action. However, it does take a few other ingredients to conquer uncertainty and forge your own path. You need discipline when motivation wanes. Optimism is the lynchpin to any serious achievement. But blind optimism can be fatal, which is why you need to prepare for the worst but take action as if everything will work according to plan.

You’ve made mistakes and will undoubtedly make many more during your life. But the cost of inaction far outweighs the mistakes that result from moving with imperfect information. In other words, action vs. inaction is always an asymmetrical bet. As our grandfather would remind us, there is a long line of folks who “shoulda, coulda, woulda but didn’t” and regret it because opportunity rarely knocks twice.

With that preamble out of the way to state what you already know intuitively and live according to as if doctrine, let’s move to update you on what the future looks like. In other words, this is where your future self (me) stops writing typing and gives you control of the keyboard. I can only tell you what’s happened after you’ve future-casted it.

It’s time to lay the stepping stones to your future and immediately return to forging your path!!!

[GYFG Here: Dear reader, please bear with me as I have an inner dialogue with my present and future selves. Please don’t get confused as I switch back and forth and realize this exercise is about articulating a future I desire for me and my family.]

Some Life Updates

Your Amazing Kids

It’s been four and a half years since the last letter, and that means that Declan is almost five, and Ramona has recently turned two as you read this. It’s hard to articulate how your kids grow into their own over the next decade, mostly because I don’t want to spoil the experience as it unfolds.

Here is what I will say: The focus on having fun and making memories with your kids has significantly influenced the incredible humans they have become. I do not doubt that you are raising eventual independent adults. You have helped them view life as one grand adventure with its ups and occasional downs, but mostly ups. They are grateful, humble, empathetic, generous, and naturally curious – with an unquenchable thirst for learning.

You and Jenny wanted to give them an advantage but avoid crossing a line in crippling them to find their own life purpose and ambition. They understand and appreciate their advantage and realize how lucky they are. They show no signs of entitlement, which was a fear we shared.

They are happy and healthy and still love hanging out with their parents.  They love the tradition you and Jenny started in late 2023 with the “adventure envelope series,” wherein each of 12 envelopes contains the recipe for a monthly adventure that evolves as they grow and their interests change. They get a good balance of bonding with just Mom or just Dad. And then there are the full family adventures that allow you all to bond even tighter. They look forward to stuffing the envelopes with adventures every December on the eve of Christmas Eve (or what we refer to as the Christmas Adam).

The Home Resort

The goal of transforming your home into a personal resort you never have to check out of is no small task. It is a worthy one though, with our vision for how we want to live and create memories with our friends and family. The five-acre property was already nice, but its potential is what made it the dream property and forever home.

Today, the property is part resort, part homestead, and part vineyard – you had to embrace the fact you lived out in wine country after all by adding a vineyard (and awesome wine cellar). And it’s multi-generational living with your father-in-law in the casita. I’m still so grateful that you and Jenny made plans to buy the property with the full intent of multi-generational living before your mother-in-law passed away unexpectedly. I know this made it easier on your father-in-law. What a treat for your kids to see their grandfather every day.

There have been lots of improvements over the years. The big ones include the kitchen remodel (prior to moving in); the pool and hot tub; the full outdoor kitchen (complete with pizza oven, griddle, BBQ, fridges, and double oven range); the 500 square foot gym; sauna; steam room shower; cold plunge; outdoor fireplace; pig pit (for those annual pig parties); the vineyard and wine cellar (2.5 acres producing about 5,000 bottles a year); and your private office up on the hill. And you guys did a great job staying true to the Hacienda style of the house.

Oh boy, at one point, you probably thought the permit, weather, and construction delays would never end and projects would never be completed. It was frustrating, but the memories you have created already have made it worth all the hassle and frustration it took to get these projects across the finish line. It’s always good to remember that nothing worthwhile is ever easy!

Don’t forget “Spa Fridays” at home (not every Friday, but plenty to lose count)…mostly with Jenny, but sometimes with occasional guests. It’s so awesome to have all the amenities of a spa and a masseuse that comes to the house. The routine never gets old…workout, shower, cold/hot therapy, massage, and hanging by the pool. Then, the welcomed chaos begins with pizza and movie night with the kids and their friends.

You built the house of your dreams that allows you to entertain to your heart’s desire, to be pampered often, and to produce food and wine to be consumed and shared with friends and family. The views of wine country are stunning, especially when paired with those sunsets. You are living a dream, but it’s real life!

The Grand Tour Begins

The time also came to kick off a decade filled with travel and exploration. We will never forget learning about The Grand Tour during our visit to Hurst Castle. Learning about how William Hurst went on a trip around the world for eighteen months planted a seed for us to create our travel plans with our eventual kids. But instead of 18 months of world travel, we would spread it out over 18+ years with our kids. It would have been pretty easy to defer all this travel until the kids were a little bit older, but then where do you draw the starting line? It’s a balance of them being old enough to make travel a little less difficult on us as parents but also old enough to remember it. You and Jenny decided that three and six would be the magic ages to begin. By then, they are potty trained, talking, and mostly feeding themselves…and any nearby dogs.

No doubt, they will forget some locations and details, but that happens even with adults, and yet we still choose to travel. In fact, some of our greatest “memories” are the ones conjured up from looking at old photos and sharing stories with others. Some may argue that the pictures and stories create memory dividends that may bring even more joy than the actual event itself.

You kick it off with an easy trip to Mexico for five short days in 2023… to warm up and prepare for the Italy trip you’ve been thinking about for years (one of many). Next is a 30-day trip to Italy to explore Sicily (your ancestor’s homeland), Florence, the Almafi Coast, and Lake Como. Then it’s Costa Rica, France, Spain….well, the list goes on, and one adventure leads to discovery of the next.

I hate to end the letter here but we have a plane to catch.

Enjoy the adventures that lie ahead!!!



Gen Y Finance Guy

Hey, I’m Dom - the man behind the cartoon. You’ll notice that I sign off as "Gen Y Finance Guy" on all my posts, due to the fact that I write this blog anonymously (at least for now). I like to think of myself as the Chief Freedom Officer here of my little corner of the internet. In the real world, I’m a former 30-something C-Suite executive turned entrepreneur turned capital allocator. I am trying to humanize finance by sharing my own journey to Financial Freedom. I believe in total honesty and transparency. That is why before I ever started blogging, I decided that I would share all of my own financial stats. I do this not to brag, but instead to inspire motivate, and also to hold myself accountable. My goal is to be a beacon of hope, motivation, and inspiration, for you, the reader, by living life by example and sharing it all here on the blog. My sincere hope is that you will be able to learn from me - both from my successes and my failures! Read More



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