The Entrepreneur: The Head of the Chicken

A well-known phrase in East Asia goes something like this: “it’s better to be the head of a chicken than the tail of an ox.” In my brief and cursory research for this post, I noticed several variations, including my personal favorite: “it’s better to be the head of an ass than the tail of a horse.” Either way, the phrase celebrates the entrepreneur, recognizing those who go out on their own.

The idea is profound, especially in modern times, where greater power in the employment market is being centralized with fewer and fewer individuals. Sure, a corporate job might feel safe, but in this post, we examine the human toll on being “the tail.”

The irony is that I’ve spent the entirety of my working life in the tail of the proverbial ox. I’ve never been an entrepreneur, always the worker bee. And for the bulk of the last decade, I’ve worked for large organizations, some of them with thousands of employees.

It’s better to be the head of a chicken than the tail of an ox.

To be fair, some organizations that employed me were small, and there was a tiny element of family. Those jobs, primarily in the restaurant scene, were the most enjoyable times I’ve had in my working life. Sure, I might be looking back with rose-colored glasses to some degree, but despite the low pay and grueling hours, there were some key elements in place for job satisfaction: fast pace, autonomy, creativity, and engagement. Entrepreneurs experience many of those same elements.

But don’t you want to retire early?

Yes, our saving and investing strategy is built to provide enough passive income to never work again. By that definition, sure, we could actually retire in our 30s. Based on just about any modeling scenario ever done, when we reach our goal, we can theoretically expect a very low chance of running out of money before we are returned to dust. Of course, assuming we continue to keep our spending in check.

However, many in the FIRE movement (Financial Independence/Retire Early), and even traditional retirees, report a high level of boredom or even depression when faced with 40+ new hours of unstructured time off.

Financial independence is wonderful and all, but if you fill all of your downtime with TV in your working life, you won’t automatically flip a switch and have a a handful of productive hobbies. Just like getting a dog won’t turn you into an avid runner. The list goes on. Check out this and this for a couple discussions on the boredom dilemma of retirement, both early and traditional.

For me, there’s two reasons why I’d like to be at the helm of a new venture even after I’ve reached financial independence.

(1) Additional income lowers sequence of returns risk.

(2) having a meaningful entrepreneurial venture provides work and life satisfaction. I’ve rarely encountered that in 8+ years of time in the tail of the corporate ox.

The Corporate Model Vs Entrepreneur

The corporate world has been the butt of jokes (or the tail? Get it??) for decades. Often-quoted movies like Office Space or shows like The Office highlight some of the ridiculous cultural elements that exist in the corporate world. It’s no surprise then that a majority of Americans are not satisfied in their jobs.

I actually work for a good company that treats its employees well. I have a great salary, reasonable flexibility, and a good deal of vacation time. What’s the problem?

Well, for many people, there is no problem. You do you. But my personality is such that I clash in this environment. I find it increasingly difficult to be motivated to work non-stop for nine hours a day to meet a quarterly production goal. Even if I’m a key team member, I feel distant from the product and even more distant from the company’s greater ambitions. A common sentiment and cause for job dissatisfaction is that employees don’t have much say in how the company is run. Finally, there’s the inescapable fact that despite my best efforts in the tail, those at the head of the ox reap the most benefit.

What’s next as an entrepreneur?

Honestly, I don’t know. I will leave the corporate ox tail once we are satisfied with our financial situation. Mrs. CC, however, would like to stay on with her ox, for some time at least.

I want to embrace what I feel is the long-repressed spirit of an entrepreneur. The beauty of this is that the bar for “success” is quite low. We will likely not even need the money! Obviously, it doesn’t make sense to embrace a money-losing proposition, but I also don’t need to provide for our total cost of living. The compound interest from our investment strategy is handling most of our cost of living.

Maybe just running this website is enough. I don’t make any money, but after nearly eight months of writing here, I gain far more satisfaction out of this work than what I do in the tail of the ox. Perhaps putting more focus here in the future will be engaging and satisfy my needs.

The Fog Shall Clear

There’s also the “Fog of Work.“ This concept, first introduced to me by Doug Nordman of The Military Guide, explains that it’s no surprise that we don’t know what we want to do with more free time. We’ve been so busy working, preparing for work, commuting to work, or recuperating from working for so long that we haven’t had the chance to figure it out! So, when people tell me they don’t have a recreational passion or idea for a side business, it’s completely forgivable. You probably haven’t had much time to consider it!

I’m confident, with time for the fog to clear, that I’ll come up with something that’s engaging as an entrepreneur. Maybe if I’m lucky, this engaging work will make a little bit of money too. My unapologetic criteria for the head of the chicken goes something like this:

• I’m not going to an office for 40 hours a week, unless seasonal
• Would prefer location-independent, potentially web-based work
• Must be meaningful for me
• I want to learn new skills
• I must be the head of the chicken

Summary

Obviously pursuing a career as an entrepreneur is not for everyone. I don’t yet know if it’s even for me! And you certainly don’t need a lifetime’s worth of investment income to finally go out on your own.

Take some of our recent interviewees for example, Kris Hampton and Justin Brown. These guys love the climbing lifestyle, noted a business niche for which folks were willing to fork over their money, and the rest is history.

I really admire those willing to take a risk and build something. Only now, after I’ve reached a very stable financial foundation, am I willing to pursue my own venture. Hats off to the entrepreneurs out there!

If money was no issue, what would you do with your time and energy?

Thanks guys, see you next week.