To Be Bossless

My boss is a reasonable person. He’s respectful, relatively adept, and cares for my well-being as much as the corporate hierarchy allows. The issue isn’t who my boss is, but the fact that I have one at all.

In January 2023, after a few months of job-hunting, I was hired at a large corporate company to fill a mid-level manager position. It’s my first big boy job, complete with benefits and a salary almost three-times what I was making at my previous job. So what’s the problem?

The job itself is alright. Pretty easy actually. I manage a small, experienced team, do some basic data entry, and generally ensure the daily operation runs smoothly. The hours are a little odd but the benefits and the salary offset the early wake-up time; I’m even building an emergency fund for the first time ever.

But there is a problem, and it’s three-fold.

First, after about three months on the job, the learning curve flattened almost entirely and I became bored. (I’m starting to see a pattern of this in my work history, hmm.) Second, the more I learn about the corporate structure at this particular company the less I believe in its ability to foster healthy communication, compassionate treatment of employees, and realistic workloads. Third, and equally important, the job is incredibly unfulfilling. I want to work to live, not the other way around.

I want out.

Truthfully, I’d like to quit right now. No notice, no gathering of belongings, no goodbyes. Clap the dust from my hands and be done with it. But, alas. This salary is the only way I can afford such a robust portfolio of productivity app subscriptions. Without those, how else would I avoid difficult tasks? So, I can’t just quit. Like most people, I need to replace my existing income with something else before leaving the land of org-charts and absurdly long email chains.

With this roadblock in place, my work/life future has begun to look grim. I see a future where I hop from job to job, working one until I’m bored enough to find another. Always another boss, always more banal tasks to be completed day-in and day-out. Not good.

Fortunately, I recently picked up Tim Ferriss’ The 4-Hour Work Week and it helped me expand my perspective and consider a different way of working and living. A way that includes far fewer bosses (ideally none) and far more fulfilling life experiences. I tore through it in about a week. If you’re unfamiliar with the book, it’s best described as a sort of bible for those who find themselves overwhelmed by work and lacking the time for fulfilling life experiences. (i.e. me right now) Tim’s guidance for wannabe entrepreneurs is prescriptive and well-researched and has helped me gain the confidence to imagine a life (ideally) boss-free. Which brings me to the purpose of this blog and the journey on which I am about to embark. A journey I’ve dubbed: “My Journey to Bosslessness.”

What is bosslessness? If it were in the dictionary, I imagine it’s definition would read something like:

I’m tired of bosses. I don’t want another one. I want full autonomy over how my time, energy, and resources are spent. I want to travel, to spend significant time with my loved ones, and to experience things I can’t possibly imagine. It’s possible. But, like all things worth doing, it seems my journey from boss to bossless will take considerable focused effort. Is it doable? Yes. Quick and easy? Almost definitely not. So, here I am. Stuck between a boss and bosslessness. Trying to escape one and create the other. And it’s from this plebeian limbo that I begin my journey.

Put simply: my goal is to create and nurture some sort of entrepreneurial endeavor that will eventually replace my current income and enable me to leave my current job. Each week I’ll check in with updates and reflections. I’ll be documenting my experience and sharing it by way of this blog. It’s my hope that sharing my experience will provide a little comfort, or at least a little community, to those of you who might feel similarly. I encourage you, if you’re so inclined, to respond to these posts with feedback about the blog and anything that resonates with you via email. I’d love to hear about your experiences with bosses and whether you plan to extricate yourself from yours (or have already). Additionally, if you have a juicy story about a boss and feel comfortable sharing it, please email it to me at [email protected]. Make sure to include your explicit permission for your story to be shared on the Bossless Blog and whether or not you’d like to remain anonymous. I’m planning to add a Bossy Bosses section to each post where I’ll include these reader contributions each week.

And so, we begin. I’m excited and nervous to begin this journey, but mostly excited. Maybe following my journey will inspire you to embark on your own journey to bosslessness; or maybe my experience will serve as a reminder of all the wonderful ways having a boss actually makes your life easier and more fulfilling (but I doubt it).

With exasperation and hope,

Will

P.S. The name Will Barnes is an alias. As I mentioned above, I can’t leave my current job until I have another comparable stream of income and I’d like to prevent my boss from firing me first. Please don’t seek out my real identity. I will reveal myself when the time is right.

All Bossless Blog social media will be titled as such or connected to the name Will Barnes. You can reach me via email at [email protected] or reach me on Twitter @BosslessBlog.

To buy the Four Hour Work Week:

https://www.amazon.com/Hour-Workweek-Escape-Live-Anywhere/dp/B004C71SLM/ref=sr_1_4?crid=20LT8LK6MWWEK&keywords=four+hour+workweek&qid=1688348586&sprefix=fourhourworkweek%252Caps%252C149&sr=8-4&_encoding=UTF8&tag=bosslessblog-20&linkCode=ur2&linkId=f8483ca41458d7b48178d7bc390a461a&camp=1789&creative=9325">Four