A reader named “Moo” recently posed an intriguing question: How do I decide what to work on as an entrepreneur, and what’s my process for choosing topics to write about? As a lifelong entrepreneur who’s enjoyed a measure of success, it might seem odd that I don’t often share insights on this subject. The truth is, my decision – making often involves trading potential financial gains for other precious commodities like freedom, autonomy, and a high quality of life. I suspect that many seeking entrepreneurial advice are primarily focused on the pursuit of money, whereas my priorities lie elsewhere.
I’m not even sure if I’d recommend my approach to others, as it’s highly personalized to my unique preferences. But I’m more than happy to open the doors to my thought process, in the hopes that it might inspire others to think differently about their own entrepreneurial journeys.
At the heart of my method lies a simple yet profound principle: life is a remarkable adventure, and my ultimate goal is to maximize my experiences within it. Of course, money is necessary to access certain aspects of life, and more of it can unlock even greater possibilities. However, these often come at a steep price— increased stress, less time with loved ones, or engaging in work that lacks personal meaning.
With this philosophy in mind, I’ve made a firm commitment to only work on projects that genuinely interest me. I’d rather live a life of relative poverty than amass a fortune doing something I loathe, and my 15 – plus years of blog posts serve as a testament to this unwavering stance. If I were offering advice, I might tell someone to choose the most profitable option among the things they love to do, but that’s not always a path I follow myself.
There’s a certain magic in doing what you love. You’ll master the skills required much faster than if you were slogging through tasks that don’t ignite your passion. And when you become proficient, opportunities for commercialization often present themselves. Take my blogging journey, for instance. I spent years writing without making a dime, driven solely by my enjoyment of the process. Later, when I decided to write books to share my ideas, my blog readers were eager to support me. What seemed like a non – profitable endeavor at first eventually became a source of income. Similarly, when I created CruiseSheet, the thought of it becoming a lucrative business never crossed my mind. I simply wanted a list of cruises sorted by the best price per day. As I chipped away at it week after week, it blossomed into a successful venture.
But not all my projects have been money – makers. I’ve poured countless hours into building a new blogging platform, designing realistic fake candles, and creating a social task platform— none of which yielded significant financial returns. Yet, I don’t regret a single moment spent on these endeavors because I was passionate about bringing them to life.
Most people prioritize money in their entrepreneurial pursuits, but I take the opposite approach. I start with the activity that excites me and then try to find a way to monetize it. If it works out, that’s wonderful; if not, it doesn’t dampen my spirits because I was fulfilled by the process itself.
One of the reasons I’ve been able to adopt this approach is that I’ve designed my life to be adaptable to both financial abundance and scarcity. For about seven years, I lived in an RV on the side of the road, splurging on the cheapest flight deals I could find— long before the “van life” trend took off. During that time, I was just as happy as I am now, because I was able to focus on the things that truly matter: spending time with loved ones and working on meaningful projects. I understand that this level of frugality isn’t appealing to most, which is why I don’t aggressively promote my entrepreneurial methods.
That being said, I have no qualms about charging for my work. It baffles me when people who are passionate about their projects shy away from asking for compensation. In my view, it’s a natural progression: work on something that matters to you, and when it creates value for others, it’s only fair that you receive a portion of that value in return.
Once I’ve established a business, my top priority is to make it the best possible option for the user, even if it means sacrificing some profit. At CruiseSheet, for example, we include taxes and fees in the price, unlike other cruise agencies. This decision might cost us some customers in head – to – head comparisons, but I believe it’s the right thing to do. Hiding fees until the end feels like a disservice to the customer. Similarly, when I was coaching, I turned away clients I didn’t think I could provide substantial value to and even encouraged some to quit if I felt it was in their best interest.
Within each business, I balance my personal interests with the practical needs of the venture. I might spend hours on small, niche features at CruiseSheet that may not have a significant impact on the bottom line but are fascinating to me. I like to think they contribute to the overall charm of the site, even if no one else notices. However, when urgent issues arise, I drop everything to address them.
Most of the time, I’m working on projects that I’m passionate about. But like anyone, I also enjoy the thrill of success and business growth, so tasks with profit – generating potential do hold a certain allure. I’m sure my more traditionally successful entrepreneur friends might disagree with my approach, but that’s okay.
I also make sure to carve out plenty of time for non – work activities. I’ve witnessed too many people burn out, wasting their days on unimportant tasks. I make it a point to engage in activities that bring me joy, like playing pinball, savoring a cup of tea for an hour or two, getting a full eight hours of sleep, spending quality time with my wife, and relaxing in the steam room and pool. These moments of leisure not only enhance my quality of life but also keep me fresh and motivated, ready to tackle any urgent work that comes my way.
My entrepreneurial methods are deeply rooted in my principles, perhaps even in some innate characteristics. They’ve remained relatively constant throughout my journey, regardless of my level of success. Other than a three – year period where I worked intensively to build good work habits and gain experience, I’ve always prioritized my fulfillment, satisfaction, and mental health over traditional markers of success. While I may not have achieved the same level of financial success as some of my peers, I have no envy. We’ve all made the trade – offs that align with our individual values, and I’m content with the path I’ve chosen.
