Break the endless loop of trading your time for money
Take back your time, your earning potential, and your voice
I Had Arrived
I can still remember the way I felt on April 24, 2017 when I walked into 888 Brannan Street as an Airbnb employee for the first time, not just an interviewee. Here I was again, in one of the most beautiful buildings I’d ever seen, in the headquarters of a household name San Francisco tech unicorn, and they’d picked me. Not only that, it felt like I had manifested it back in 2014, when for my final project at the coding bootcamp I was attending, I’d created an Airbnb clone I lovingly dubbed Laissez-Fairebnb. It hasn’t been updated in almost 7 years as of this writing, be gentle.
Landing six-figure jobs at household name tech companies was a massive step up for me at the time. My previous careers included but were not limited to:
Bagging groceries at a supermarket
Selling dime bags of weed in high school
Trimming trees
Working for a moving company for almost a whole week
Working for a catering company for a whole weekend
Being an unpaid student working for an expensive and mostly useless piece of paper
Driving a taxi
Selling dime bags of weed from my taxi
And now here I was, making a salary higher than I ever expected, not to mention stock units and bonuses, getting amazing food, travel, and other perks as part of my job, working with brilliant and amazing people in the most beautiful, airy, light, whimsical, fun office I had ever seen. Why wouldn’t I want to keep doing this for as long as possible?
The Golden Cage
As I settled into this amazing job, and the novelty of all the fun work parties and pulling my own shots of espresso wore off, I started to feel tired and burnt out very quickly. The limitations I ran into are in no way specific to Airbnb or any other employer that I’ve had. I value all of the experiences I’ve had and the people that I’ve met at those companies. But in the process, I discovered some limitations that are inherent to being a tech employee, and possibly inherent to being someone else’s employee, period.
Your time is not your own.
On the surface, my schedule as a software engineer was pretty flexible. A standup meeting in the morning, maybe a meeting here and there throughout the day, spending most of my time working at my own pace, going for a walk or a snack whenever I felt like, my output being judged in terms of weeks, not hours. As I grew more competent at my job and took on more responsibility, I found myself spending more and more time at the office. Sometimes it was because I was behind on a project and felt pressure to get it done. Sometimes it was because there was a fun work event and I didn’t want to miss out. Sometimes it was because someone else put a meeting on my calendar and I didn’t feel empowered to decline it. Regardless, I quickly reached a point where I was spending far more of my waking hours at the office than with my partner or non-work friends. I was grinding for a promotion and a raise, and unsure of when or if that would actually pan out. I was tired, stressed out, and started to show toxic behaviors in some of my relationships.
Your earning power is not your own.
I can already hear the first objections - “You were making a six figure salary, plus stock units, plus bonuses, plus free food and tons of perks, and you’re complaining about not having control over your income? Typical entitled tech bro.” And fair enough - I can easily see why discussing the downsides of a relatively lucrative and prestigious career could be seen as tone deaf by some people. But there are a few things I’d like to bring to your attention about your situation if you’re a high paid W-2 employee like me:
You’re probably making the CEO and other executives of your company much, much richer than you’ll ever become as their employee
The extra input and effort you need to put in to get a raise is incommensurate with the amount of the raise. For example, you might get a 10% raise if you successfully get promoted from “Software Engineer” to “Senior Software Engineer”, but it’s unlikely you’ll pull off that promotion with only 10% more time and effort than it would take to tread water.
Your value to the company may be very difficult to quantify, and whether it is or not, somebody else is capturing that leverage. I worked on a single project one time where I probably saved the company hundreds of thousands in customer support costs, and I personally captured exactly 0% of that value. Your situation may be a little bit different if you’re in sales or a position where much of your pay is commission, but you’re likely still trading your time for money and will need to put in more hours to make more money.
Your opinions and conscience are not your own.
This article isn’t the time or place for a long screed against the cultural phenomenon which encompasses “cancel culture” and political correctness - maybe a later article. But suffice it to say if you were fired from your job for posting any kind of non-mainstream (or possibly even quite mainstream) viewpoint or opinion on the internet, you wouldn’t be the first. You probably wouldn’t be in the first 10,000. When someone else is a gatekeeper for the entirety of your income, you’re not free to express your conscience without fear of retribution.
What’s Next?
Years ago, I found myself saying things like “one day, I’ll invest in multifamily real estate”. I’m not even 100% sure how the idea got into my head (my fiancée says she put it there, and I’m happy to take her word for it), but deep down somewhere, I already knew that trading my time for money was not the endgame, regardless of how much money my time was valued at, or how many perks I was handed in the process. One day in late 2019, a switch flipped somewhere in my brain, and “someday” turned into “as soon as possible”. Within a few months, I’d closed on my first piece of real estate, a small multifamily property that I house hacked (Bought with an FHA loan and lived in during initial construction. In retrospect, I wouldn’t recommend living in a property during construction unless you really have no other options).
More recently, I took a ProMaster van that I had previously lived in for a year in LA (more on that later), in addition to another RV, and started renting them out for additional income. Now, I’m also in the early stages of learning how to identify and purchase an existing profitable business.
I don’t have this all figured out yet, and my passive/horizontal income is not yet high enough to comfortably quit my W-2 job today, but at the rate I’m going, it won’t be too much longer before I’m earning more money than I ever did working for someone else, all while being in control of my own time, earning potential, and my own voice and conscience. Want to learn with me, watch me grow, and figure out how to make some of the same moves?
This newsletter probably isn’t for you if you:
Are committed to limiting beliefs about yourself, about money, about other people
Believe that wealth is evil and that it inherently corrupts people
Believe that landlords and business owners are leeches on the working class
Prefer being told what to do over thinking for yourself
Are comfortable with where you’re at and not committed to personal growth
Are risk-averse
Are resentful of people who are more successful than you
This newsletter probably is for you if you:
Are earning a high salary and wondering why you’re not getting wealthy
Have a strong desire to serve other people, and believe that you can become wealthy as a result of providing value for others
Are a weirdo who doesn’t want to hide large parts of yourself for the sake of fitting into a company culture
Want to spend more time with your family, traveling, pursuing your favorite sports and hobbies, and doing anything else you actually love doing
Are committed to personal growth for its own sake
Understand the importance of taking calculated risks
Are inspired by people who are more successful than you
What to expect from Break and Continue
In the future, I may do some writing on any number of topics that interest me, including martial arts, mountain biking, lifting, the van/RV lifestyle, watches, tattoos, evolutionary psychology, psychonautics, love, virtue, or my thoughts on how to live a good life in general. For the time being, I’m going to focus on what it’s like to be a W-2 employee making the transition to full time investor and entrepreneur. I’m coming from the tech industry, but most of what we’re going to discuss will be highly relevant no matter what industry you’re in, as long as you’re currently working for someone else and have a fire under your ass to achieve financial freedom.
This newsletter will likely contain some in-depth analyses of different deals or income strategies, interviews/case studies/guest essays from people who are in various stages of making the leap from employee to investor/entrepreneur, and various principles that most of the highly successful people I’ve ever met have used to get to the next level.
Stay tuned for the next article about 3 Simple Rules to Stop Trading Your Time For Money:
Stop trying to get a promotion
Invest in yourself
Level up your network
And in the meantime, please subscribe and share with anyone you know who might be interested!
What do you think of the title of this newsletter? What topics would you love to see discussed here? Who should I be talking to? Leave me a comment and let’s talk about it!