Everything Always Works Out – New 10 Year Vision Letter




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Wow! I can’t believe it has been three years since I went through this exercise for the second time in ten years to plant the seeds of what I desired my life to look like over the next ten. Here is the second of these letters, the one that I wrote in March of 2019.

I’ll likely take the opportunity to write another letter in the next one to two years to continue this exercise as I find it very helpful to not only set direction but to force reflection periodically throughout the decade, which allows for any sort of course correction needed. I like a decade because my imagination can’t go much beyond that amount of time. 

As you read the letter below, you will notice that I have peppered in some comments (in brackets) based on reflection from the current day.

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 March of 2029. I obviously know about the decision you’ve been struggling with because you are me and I was there ten 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 also 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, which is option #3…

(3) You hang out 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 all these 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, we knew 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.

[I certainly used this letter to gain confidence in making the decision to scratch the itch I’ve always had to try my hand at entrepreneurship. I also acknowledge that my “risk mitigation first” philosophy, developed much earlier than the onset of this big decision, also played a big role in giving me the confidence to take the leap of faith. One of the actions I took early on to mitigate risk was to pay off our mortgage early to afford the kind of optionality being debt-free offers when presented with once-in-a -lifetime opportunities like this. I recall the biggest fear I had was in risking the lifestyle my family had grown accustomed to. 

I’m very pleased with my decision to not go the private equity route from the start, although it was tempting to let them bear the risk burden. Something that also worked out in an unexpected way was my giving a six-month notice to my employer. I didn’t expect them to take me up on the entire notice period, but I wanted to leave on excellent terms and ensure that I didn’t burn any bridges. Not only did they take me up on it, but my notice actually ended up being eight months long, even though within 2-3 months I was running my business full time and working a fraction of the corporate hours I had once worked. I was very transparent with the CEO at the time and his response was “I know you are running your own business and you’re not able to give us full-time attention but I’m not going to cut your pay and all I ask is that you focus on transitioning the critical things off your plate – even if it takes longer than the six months.”

This decision – option #3 – was indeed an x-factor and accelerator in propelling us to our $10M net worth goal. Back in March of 2019 our net worth was just over $1.1M and three years later it’s almost $8M.] 

By the time you’re reading this letter, Declan is five 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. Waiting 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 the terms you set.

[I really was setting an intention in this letter to move away from the long hours I had logged over the prior years to achieve my ambitions. For a long time (before kids) I didn’t mind the long hours because they had a purpose to act as an accelerator to achieving my goals and desired lifestyle. I also had enough self-awareness to remind myself that this was a temporary modus operandi and was a means to an end. I’ve been very intentional over the last 18 months to transition away from 70 to 80 hour work weeks. For the last five months, since selling 60% of my business, I have reduced my workload to a very strict 40 hours a week. Come October 1, 2022 I will be going down to four days a week (32 work hours).] 

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.

Success as measured by money can be all-consuming if you allow it to be. Not many can escape its gravitational pull as elegantly as you have 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 won’t in order to live as most will never be able to.

[Whether it’s obvious or not, if you read between the lines you’d know that I had my own doubts about being able to successfully pull off this transition. I’m proud to say that so far I’ve been able to “stick the landing.”]

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 Quasi 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. But that is all I can say about this for now.

[I’ve set a handful of major goals in life:

  1. Make it to the C-Suite by climbing the corporate ladder (check)
  2. Start, Scale, and Sell a business (check)
  3. Become financially independent (check)
  4. Reach self-defined definition of financial freedom of $10M net worth (80% complete)
  5. Transition to become a full-time investor and family man to live life by design (actively executing now and for decades to come)

We did indeed welcome our second child (Ramona) into our lives in August of 2021.]

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.

[I can’t wait to start exploring the world with our kids. We plan to defer international travel until the kids are three and six years old but will be enjoying plenty of local/domestic adventures until then.]

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.

[We think we have an exit plan for Jenny…and we are both planning to go down to four day work weeks come October 1.]

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)

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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7 Responses

  1. What a beautiful and magnificent letter, Dom.

    So glad you bet on yourself vs. the private equity route.

    Your journey continues to inspire me and many and I continue to smile upon your continued success in all avenues of life.

    Your family is so lucky to have your presence now and into the future. I can’t wait to see what the next decades hold for you.


  2. I always was skeptical about these kinds of letters, thinking that as we grow our values, direction, and situation changes. However, I can see the power of reflection in these. That’s why weekly journal entries work well for me, it provides that near term reflection. As long as you’re spending your days living a life of fulfillment, or helping you get to that point, you’re on the right track. Like you say, we’re only here for a certain amount of time!

  3. I always love reading your blog posts. Really helps me to feel expansive in my own goals and to really think big. Keep it up, man!

  4. Fantastic, and uplifting! If you ever want to add a reader-addendum, please consider my prediction for 2029: a new city will be incorporated, “Rancho DiBernardo.” Am loving the goals, pride, Mrs. GYFG exit-plan and professional cert accomplishment, and time with progeny. As you say, ‘onward and upward!’

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