What Does Bosslessness Look Like?

It’s week two and the dopamine rush I got from deciding start my journey to bosslessness has faded significantly. I’m still excited and determined, but everything feels a bit quieter, and I’m faced with the reality of my goal. It feels a bit like that scene in the fourth Harry Potter book when Harry, Cedric, Fleur, and that other SEAL-team-looking dude enter the maze. At the starting point, the crowd roars and cheers, the cameras flash, and smitten fans blow kisses. Then, a flare goes off, the four contestants enter the maze, and the big scary vines close quickly behind them, shutting them off from the crowd.

Now it’s quiet, and they are alone.

Fortunately, I’m not alone. I have a supportive family, a few close friends, and an incredible partner. But it would be dishonest to omit the worry and indecision I’ve been navigating this past week. Ideas and potential challenges have been swirling in my mind at all hours. I’ve been trying my best to right-size the worries and organize the ideas. Mid-week, after some deep breathing and a solid snack, I decided to turn my focus to the things I can control. (Ryan Holiday has squeezed his way into my feed recently if you couldn’t tell.)

So, I started thinking about what my goal is and how to clarify it. I’m not new to setting goals, but I wanted a refresher on the characteristics of a quality, achievable goal, so I did a quick search on the internet. The best strategy for goal setting I found was the SMART goal acronym:

Applying that to my aspirations, I came up with the following:

Some clarification: the e-commerce business, after a maximum of six months of start-up, needs to require no more than twenty hours of work per week. My current salary is $57,000 a year so the business will need to produce that or more in annual profit. Lastly, I will need to have completed my last day of work at my current job by May 31st, 2024. Additionally, I’m working with a stretch goal in mind. My stretch goal is to condense this timeline to eight months, and to be bossless by February 1st, 2024. The purpose of the stretch goal is to increase creative thinking and strive to find the most efficient, low-cost solutions to challenges.

Whew! It’s big, but I know I can do it.

Now that I’ve clarified my goal, what’s next?

Well, I’ve decided to focus on creating an e-commerce business, so I need to do some more learning about what an e-commerce business is, what kind of work is involved, and what relevant skills and knowledge I already possess. However, I’m going to start with some introspective exploration first. Pulling from a variety of resources, I came up with a list of questions to guide my thinking.

• What skills do I have?

• What are my interests?

• What circles or industries am I already a part of?

• How can I zero in on a niche market within those circles or industries?

• Where do I see a gap in the market I can bridge? Something that needs improving?

• Does the product I create need to feel fulfilling and meaningful to me? If so, how much?

To give you a sense of the full process, I’ll share my most relevant and effective discoveries.

• I have skills in writing, reading, communication, basic construction, and creative problem-solving.

• I have significant interest in entertainment (movies, television, and books); physical activities (hiking, biking, volleyball, and generally being outdoors); and writing (I have been studying screenwriting and working on a number of projects for about two years now.)

• Having clarified my interests, I can see that I’m the most active in the entertainment industry (with a focus on movies) and the outdoor activity industry.

• I like creative problem solving, so I think I’ll start my brainstorming in product creation. However, it seems like the startup costs for product creation can be prohibitively high, so I might explore the possibility of drop shipping as well.

• The option with the cheapest startup costs seem to be knowledge-based digital products but I don’t have any specialized digital skills or really any specialized knowledge about a particular topic so I don’t see this as a viable option at the moment.

Armed with this information, I’m able to better focus continued brainstorming efforts over the course of this next week. This clarity has also quieted many of the vague worries that appeared over the course of the last week. I’ll share whatever ideas and discoveries I uncover with this week in next week’s post, along with other things I’m doing to move towards bosslessness.

In the meantime, I hope you’re navigating your work week with compassion for yourself. I’ve started doing a short stretching routine (only fifteen minutes!) each morning right after rolling out of bed and it’s had a very positive impact on my body. I feel more flexible throughout the day, I get the blood flowing, and it’s a nice way to wake up. I’m still surprised at how such a brief addition to my day can have such a hugely positive impact on my physical wellbeing!

With care,

Will

P.S. The name Will Barnes is an alias. As mentioned in my first post, 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.

You can reach me via email at [email protected] or on Twitter @BosslessBlog.

Links to referenced materials and resources: