I remember it like it was yesterday. In April of 2024 I handed in my resignation notice at my job, and of course I was met with the usual question, “what job are you going to next?” But this time was different because I didn’t have an answer. All I could say was, “I don’t have plans really. I’m just focused on enjoying life, exploring, and seeing where life takes me.”
I honestly felt a bit uncomfortable giving this answer, as I knew many of my fellow co-workers, who were amazing by the way, also probably had some deep burning desire to walk away from the stress of the full-time 9-5 corporate grind but felt like there was no way out.
I really struggled to get past the idea that I would spend my best years in the sterile environment of a corporate office rather than being out exploring the world, using my body as it was intended, and challenging myself in fulfilling ways that align with my greater life purpose. So I made it a point to find a way to break free of the golden handcuffs and retire from the corporate American rat-race.
But firstly I should say that I truly hate the term “retirement.” I’ll elaborate a bit more on this word later in this article, but let’s just say that for me “retirement” could be used interchangeably with “indefinite sabbatical.” So when I speak of retiring, just think of it more so as an extended break from work with no pre-defined return date, if any at all.
I realize that many of you have similar aspirations. Maybe you don’t want to follow my specific path, but I’ve had countless conversations with many middle aged, mid-career, high-earning white collar workers who somehow feel disconnected despite checking off all of the societal markers for success (just like myself) and the sentiments expressed in those conversations typically revolve around wanting to break free of the corporate shackles, and explore other avenues in life.
The reasons for wanting this are plentiful and deserve an article by itself, so I won’t get into that, but today I will share with you the process that I followed to “retire” from the corporate life at the age of 37.
I should also say that this is a very generalized process. There’s no way I can give you a step by step guide for your unique situation, but my hope is that from this you can take away some useful information and apply it to your own situation.
Step 1 – Take time to understand your “why.”
In hindsight, my reason for wanting to retire pointed directly to how I would be spending my time after making the big life move.
This seems like an obvious step in the process, and it is, but it’s still an important step because it sets the tone for all subsequent actions. I’ve learned through my own experience that if you don’t actually get super clear on why you’d want to make this life-changing move, then you could end up feeling a bit aimless.
So to save yourself any confusion down the road, make sure you spend a lot of time getting clear on your reason for wanting to “retire.” What I mean is that, sure you may have a burning desire that exists within you, but you’ve got to really unpack that and make it make sense.
As you unpack your reasons for wanting to make a transition away from the traditional work life that you’re currently in, you will naturally uncover the key pain points that are driving you to seek out an alternative to your current situation.
Your pain is your purpose. My philosophy is that the easiest way to find your purpose, is to understand your pain points, and then identify the actions that you’ll need to take which will alleviate those pain points.
So if the corporate lifestyle is interfering with your ability to focus on your mental health, and this is becoming a serious issue for you, then one aspect of your purpose would probably be to overcome whatever internal battles you are fighting. Thus, you’d want to align your life in a way that makes serving this purpose a priority.
But it all starts with understanding your “why.”
Step 2 – Create your own definition and vision of “retirement.”
I have a saying, “play the game of life by your own rules.” What I mean is that there exists a certain set of rules that we were programmed to operate within from the moment we were born. Almost everything we think and believe is a result of being born in a certain era, geography, family, economic group, etc. All of these things create our environment.
Our specific environments funnel us into a standardized way of viewing the world and how one should live their lives, and the issue of retirement is no different. When I say retirement, you probably automatically attach a specific meaning to the word which is associated with leaving the workforce and living the rest of life on easy mode, waking up late, sipping cocktails on a beach, watching soap operas all day, etc.
However this is not my definition of retirement, and it does not HAVE to be YOUR definition of retirement either.
One thing I’ve learned over the years is that, aside from death, there really are no finish lines for life. So unless you are truly a degenerate, which you can’t possibly be if you are reading this, you’re going to end up finding something else to do if you leave the 9-5 grind while you’re still in your prime years.
As nice as it sounds at first, spending your days doing nothing or living the “good life” will get old very fast. At 30 or 40 yrs old you’re still relatively young, you have the whole second half of your life ahead of you, and so at some point you’re going to spend your newfound freedom gravitating towards things that you are interested in. Your interests will naturally lead you to finding purpose, or as Robert Greene, author of 48 Laws of Power, describes it, you will gravitate toward your “primal inclinations.”
I’m not saying that whatever you do with your time will be something that is as stressful or rigorous as your former corporate job, but human nature dictates that you will 1) want to feel like a contributing member of society in one form or another, and 2) you will want to do something that is mildly challenging and experience the joy of overcoming that challenge.
For some it could be volunteer work, for others it could be a simple part-time job as a barista or a tour guide, or making art and selling it at a flee market. I remember hearing about one guy who left his $250k job and ended up becoming a barista because he enjoyed the artistry of coffee, and he enjoyed meeting new people. For others who are a bit more ambitious, the activity may be something more challenging such as entrepreneurship.
So with a bit of context setting, you’ll want to try your best to envision what retirement actually looks like for YOU. I’m not talking about the boilerplate retirement. I’m talking about a realistic vision of how you think you’ll spend your newfound free time. There are infinite variations of “retirement” that you can explore, and your job (pun intended) is to figure out what your variation of retirement actually looks like.
This is exactly what I did. I redefined the concept of “retirement” for myself, and then I created a vision of a lifestyle that fits within my definition of the word. In doing so, here’s what I came up with:
To “retire” is to break away from the golden handcuffs and the obligation of working full-time to support my lifestyle, and to reorient my life in such a way that the majority of my time is spent exploring things that I am deeply interested in and passionate about.
Notice how my version of retirement doesn’t explicitly entail “never working again” or anything to that nature. I’m sure I will work again, however it will be on my own accord, because I want to, and not because I need to sell my soul for a paycheck.
The Vision:
A lifestyle where I spend the majority of my days focused on health, fitness, travel, exploration, self-discovery, relationships, and entrepreneurship.
A lifestyle that doesn’t involve rushing my morning, barely having time to focus on my health, dealing with workplace politics, stressing over performance reviews, etc.
So you probably get the idea here. What I’m not describing is a life of just chilling on the beach and never working again. Rather I’m describing a life where freedom, flexibility, autonomy, all things that are top priorities in my life, is the rule and not the exception.
Step 3 – Find your path of least resistance.
Once I found MY definition of what it means to be retired. I began searching for the optimal path to my desired lifestyle.
Once again, this requires no longer engaging in the trapped thinking that retirement is an all or nothing issue. I rejected the notion that retirement translates to spending the rest of my life doing nothing…. Or in other words, my version of retirement lies somewhere in the spectrum between the high stress full-time 9-5 corporate grind and living life on easy mode.
In the circles of early retirement fanatics, the status quo thinking says that one must reach several million dollars in the bank or retirement account so they have enough to live off of 4% of their investment on any given year. But there is one fundamental flaw in this logic because it assumes you will do nothing and adopt a lifestyle similar to someone in their 60s or 70s who’s coming off of a lifetime of working.
As discussed earlier, being in your 20s, 30s, or 40s, you most certainly will have a natural desire to be productive in some way through hobbies, part-time or contract work, volunteerism, entrepreneurship, and other interesting projects – all of which can be monetizable to one degree or another. Hold onto this thought for a moment.
But in short, the path of least resistance is a VERY personal thing. There is no correct way to do this as it is different for each person and their unique life situation. I could write a 10,000 word article on this topic alone and still not cover everything.
I’ll just say that my path of least resistance involved a combination of minimalism and passive wealth creation that significantly reduced my financial burden. It is super important to know, however, that what I did NOT do is attain millions of dollars that I could simply live off of for the rest of my life.
Regarding minimalism, I ruthlessly eliminated unnecessary expenses, and downsized aspects of my life. I got rid of almost everything I own to the point where all of my material possessions can fit in a single moving box. I leveraged what I call geographic arbitrage which entailed moving away from the U.S. to Portugal where my cost of living is significantly lower.
You may be thinking that this is too drastic of a sacrifice to make in the name of “early retirement” but if you recall, my vision of focusing on health as well as having freedom and autonomy does not align with having a nice home in Chicago full of a bunch of material possessions. So minimizing the deprioritized aspects of my life actually created more opportunity for me to get aligned with my retirement vision.
Regarding passive wealth creation. I used two primary vehicles to achieve this. Real estate investing being the more traditional of the two, and the second was through years of buying and holding crypto. I get it, a lot of people are skeptical about crypto and I’m not going to make an argument for it here, but the real point is that I identified a “wealth amplifier” and I went all in on it.
Wealth amplifiers are the opportunities that create outsized returns relatively quickly. There is ALWAYS an emerging technology or a revolutionary business model, or some company that has monopolized a market out there. And quite frankly they are often hiding in plain sight. The catch is that you must absolutely, and obsessively build your knowledge in that particular domain to the point where you can make sound investment decisions. I’m talking, every minute of free time dedicated to books, podcasts, interviews, articles, reddit forums, etc. to put yourself in a position of information asymmetry in which you have a comprehensive view of the topic that most other players in that market will never put in the effort to replicate.
There are people out there who did this for Amazon, or Apple, or Tesla, or Nvidia, or crypto, betting against the housing market in 2007, or (insert wildly successful asset). They obsessively acquired knowledge to make bets that have asymmetric upside potential based on their best understanding of the facts.
I need to add a disclaimer here that I am no financial advisor, so take everything I just said with a pinch of salt. None of this is a sure bet, but this has been my wealth amplification strategy, and it has served me well. I truly do believe that people who obsessively acquire knowledge, and then use that knowledge to generate a comprehensive view are in the best position to leverage wealth amplifiers to their advantage.
Lastly is monetization of my newfound free time. This one is a bit of an X-factor because it’s highly variable and can be done more or less aggressively depending on your circumstances at the time. But as mentioned before, at this age, doing nothing is not a viable option for me, and neither is it for you. So part of my retirement strategy has been to monetize my free time through entrepreneurship and low intensity part-time contract work.
At the moment I am full time with my entrepreneurship endeavors. So yes, I’m living out my definition of the retirement life, as I am no longer shackled by the golden handcuffs of the 9-5 corporate world, but I certainly do work. Only, when working for myself, work is not work in the same way that the corporate life is.
I haven’t even explored the part time work avenue yet, but I’ve been toying around with a few opportunities to pick up a 10-hr/week gig in the crypto space in the spirit of learning and monetizing a bit more of my time.
The beauty of this is that I can throttle up or throttle down my efforts to monetize my time on an as-needed basis, rather than being permanently and fully committed to the 40 or 50 hour work week for the next 25 years of my life.
There is one final important point regarding this whole thing which is that because I’m exploring different monetization pathways, in combination with wealth amplifiers, and also have the steadier income of real estate investment, I lowered my financial bar for retirement.
What I mean by this is that I essentially “retired” with about 10 years of runway saved up. I have "bought back my time," and because I’ve established steady real estate income, I’m invested in wealth amplifying assets, and because I’m spending my newfound free time exploring different things that interest me, learning new languages, trying out different businesses, etc, I feel more than comfortable with the idea that sometime between now and 10 years from now I’ll figure something out to extend my 10 years of buffer into potentially a lifetime of maintaining this lifestyle.
My path of least resistance to retirement was to buy myself 10 years of time to figure out the rest of my life. Maybe this isn’t how you’d do it… but I’m playing by my own rules.
Step 4 – Execute, execute, execute… take action.
This last piece is very simple, so I won’t spend much time talking about it. However, it is still quite difficult to do. Because executing on the plan to make such a drastic life change comes with no shortage of fear, uncertainty, and doubt.
This ties back to step 1, understanding your “why,” and if your reasons are sound enough, then they should give you the confidence in knowing that you’re making the right move for yourself.
Everything in life comes with risk, and nothing in life goes exactly as planned. However you will never escape the rat-race if you don’t escape the rat race. You have to actually do it.
You’ll need to actively take steps and make the lifestyle adjustments of minimizing wherever possible, investing as much as you can, and leveraging wealth amplifiers. Then when those things are in place, you’ll need to actively begin to turn your vision into reality. It doesn’t need to happen all at once, but piece by piece, your life should progressively align with your retirement vision.
In my case, I spent a chunk of time aggressively getting rid of stuff. I spent another chunk of time traveling to Portugal to research where in the country I wanted to live and to officially begin my immigration process. I eventually signed a lease in Lisbon, and put my home in Chicago up for sale. At another point I handed in my resignation letter and quit my job. I didn’t do this all at once. This was a piecemealed approach in which multiple actions added up to me eventually living a completely different life than I lived a year prior to writing this article.
I will admit that all of this involves a serious mindset shift in which you are thinking outside of the societal norms, and I realize that can be quite difficult. But that’s what I’m here for. As a coach and mentor, I guide people through the process of transitioning out of their traditional 9-5 and into a lifestyle where they’re living on their own terms, focusing on their health, spending more time with family, pursuing entrepreneurship, choosing employment opportunities because they want to be there and not because they need the paycheck, fulfilling personal life goals, etc.
So if you think you could use some guidance, or would like to talk through your potential pathway to “retirement” in detail, then do not hesitate to schedule a consultation with me, and lets finally get you in a position to reclaim your time and re-direct your life energy towards things that are more meaningful and more purposeful to you.