Everything Always Works Out – New 10 Year Vision Letter

Gen Y Finance Guy Words To Live By 1 Comment

Written: March 1, 2029

Sent back in time to: March 8, 2019

Dear Dom,

I haven’t written to you in almost eight years – I can’t believe it is already February of 2029. I obviously know about the decision you were struggling with a year ago, because you are me and I was there eleven years ago contemplating that same decision with you. Let’s briefly review the options that were on the table:

(1) You continue your Corporate career and in 18 months you will be COO with an income of $600,000+, $250,000+ bonus potential, and additional stock/option-based incentives. I define this as the safe path (the one that most in your shoes would take without hesitation). It will require long hours, lots of travel and time away from your family.

(2) You have an incredible opportunity to start a new business with the financial backing of private equity and the CEO of the company you currently work for. It’s a rare opportunity in that if you decide to pursue this path, you are afforded the opportunity to test your entrepreneurial chops without much risk. It too comes with long hours, lots of travel and time away from your family. You will be compensated well if it succeeds but far less than if you went out on your own, or #3…

(3) You hang up your own shingle and try entrepreneurship on your own. Although it potentially comes with more risk it also has substantial upsides (in terms of both money and time). If done right, it could give you the autonomy to live life by YOUR design – the thing you have always desired. You get to make all the rules!

When I think back to when I was in your shoes eleven years ago, I can’t help but remember feeling grateful, excited, and scared shitless. I had some serious self-doubt. I felt like an imposter. What do I know about building a consultancy from scratch? Can I sell? What if I fail? If the venture fails, will I lose all credibility? What about the people I convince to join me – what happens if I let them down? These were all questions we both had bubbling around in that gray matter between the ears.

After eight months of reflection and due diligence, you couldn’t help but obsess about the possibilities of option #3. The stars were aligned and this was the fat pitch we had been waiting and preparing for all these years. If successful, this could be another x-factor propelling us to our goal of a $10M net worth (even faster than the prior projected path landing us there at age 48). We both know that we made the right choice going with option #3.

By the time you’re reading this letter, Declan is 16 going on 17-months old. Cherish this time as he is going to grow up so fast. Isn’t being a dad amazing? You finally have the opportunity you’ve always wanted to be the dad you never had. The best part is you have Jenny to share this experience with. As expected, she is a natural; the quintessential mom. Continue worshiping the ground she walks on. You and Declan are so lucky to have such an amazing woman in your lives.

I think you can guess where I’m going with this. You and Jenny decided to do the most important thing a couple could do and that was to have and raise a child. Waiting until 32 to have little D was so smart. It really allowed you both to accelerate your careers and financial aspirations. But I will remind you that the long hours were always intended to have an expiration date. It would be nearly impossible for you to be the dad you want to be if you remained in Corporate America. Although there was more perceived risk, you knew in your gut that entrepreneurship was the only option to take in order to live life on terms you set.

It’s been an amazing decade!

I’m so proud of the man you have become. I’m proud of the husband and the father you have grown into. You have embraced a life that is guided by the principle of constant and never-ending improvement. There was a time prior to the start of the last decade that I grew concerned that your one-dimensional focus would commandeer 100% of your time and attention indefinitely. But we both know that ultimately, you were and are committed to becoming the multi-dimensional man that you were destined to become.

Money and success can be all-consuming if you choose it to be. Not many can escape its gravitational pull as elegantly as you managed to do. It’s as if every decision and step had been premeditated, which doesn’t surprise me based on your supernatural ability in planning – seeing a path most can’t see, let alone imagine. You have gone against the grain by trusting your own self-awareness and intuition. You’ve traveled the path most avoid. You’ve lived life like most wouldn’t in order to live as most will never be able to.

Your transition from corporate America to entrepreneurship in the 2020s was prescient in timing. You did Corporate America on your terms and it paid off. You managed to extract your true value in a relatively short period of time. C-Suite by 30! Then the Quazi Golden Parachute deployed by 33 after just 11 years in Corporate America. Not many people understood why or how you sustained 70-80 hour workweeks for years on end. Yet, they were still surprised when “all of a sudden” you looked like an overnight success. It’s hard for them to comprehend that it took a better part of a decade of hard work, continued learning, and discipline to become that overnight success.

So many people told you it couldn’t be done: You can’t pay your mortgage off in your early 30s. No one makes the C-Suite by 30. It’s impossible to earn raises that compound your income by 20%+ for years on end. Your goal of achieving a $10M net worth by 48 is crazy, especially at your starting point.

Who’s crazy now?

As I write, I’m 43 with a net worth approaching $15M and I work when, where, and on what I choose (I know I interchangeably write in the first person; we both know YOU and I are one and the same). These days I see you spending much of your time with your kids and wife, leaving very little time for work. Just the way you designed it. Oops! I spilled the beans, didn’t I? The cat’s out of the bag now. Yes, you enthusiastically chose to have a second child (it happened during your Italy trip after the Coronavirus pandemic had passed). But that is all I can say about this for now.

It’s amazing how you and Jenny were able to manifest your ideal lifestyle into reality. Your travels around the world have provided your kids with an education that is unmatched. Your kids have been exposed to so many different cultures, cuisines, and geographies. You have equipped them with multiple lenses through which to view the world, making them much more open-minded and understanding of different viewpoints, beliefs, and traditions.

Earlier in your journey, you preached the work/life blend, which served you well during that foundational phase in your journey, but it’s refreshing to see you invert that to embrace the life/work blend. It has become increasingly more difficult to visibly see the time you allocate to traditional work. Yes, you spend time being productive by writing and managing your family’s wealth but you have removed the kind of work that competes for your limited time. Much of what you do would hardly be classified as work by the masses. There are rarely any real deadlines. You don’t answer to anybody…except for Jenny and the kids of course (LOL).

Your job these days is just being a great husband, father, friend, brother, mentor, and overall good human being.

Although it took longer than expected, Jenny was finally able to permit herself the option to exit the family business and create the space to explore what truly brings her fulfillment. It’s not surprising that this led to her becoming more involved in philanthropic work. And she finally got that yoga certification she has always had an interest in. You love attending the hot yoga classes she instructs.

She is an amazing mother and wife. I truly believe she helped guide and shepherd you and your family to the place it is today. Talk about someone who can love deeper than words can communicate or describe. A person so selfless that she would put the needs of others above her own. She is the light of our daily existence and I can’t imagine a world where she isn’t present – it wouldn’t be a life worth living.

I will spare spoiling any other surprises by resisting the urge to tell you all about what the kids have been up to the past decade. I only withhold this information so that you can experience everything firsthand and in the moment, not through the lens of my perspective after ten years have come and gone. 

These next couple of years will be transformational. All you have to do is stay focused on optimizing the business for the last piece of the Freedom trifecta, which is Time Freedom. At this point, momentum has you covered on the Financial Freedom front. And option #3 provided you with the Location Freedom you desired. As long as you stay focused on scaling the business vs. building a job, you will achieve the Time Freedom you’re after. 

I look forward to our next correspondence.

Onward and Upward,

Dominic (you, but from the future)



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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 30-something C-Suite executive. 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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