To Be Or Not To Be (Your Own Boss)

Yesterday, an interesting and unexpected topic came up in my high school money class. A few students mentioned wanting to someday start their own businesses. This is when another student made a few counter-cultural comments. She expressed her confusion about why so many people want to run their own businesses, citing their typical lack of enjoyment and lack of skillsets in the area of actually running the business. Many students were quick to defend the be-your-own-boss concept, citing freedom and control as primary reasons.

This is the moment the questioning student called foul, fairly pointing out that the whole “freedom” argument seems to be one of the few reasons people use to justify their decision to be their own boss. She smells what I oftentimes smell. Today’s culture says being your own boss is THE definition of success. There’s even a mantra that says “stop making other people rich” by quitting your job and becoming your own boss. I think this trend is far overblown….and quite toxic. It causes people to feel guilty about pursuing traditional employment. Today’s narrative is that working a traditional job is enslaving one’s self and limits your ability to have financial success. Both of these are brutal lies. Some of the happiest and most successful people I know have traditional jobs.

I believe this is one of the many reasons most small businesses fail. So many people start their own businesses out of a sense of need. They think that’s what they are supposed to do. Being your own boss is HARD….and we can be the worst bosses in the world. In my years coaching businesses, there’s a general truth that I can almost count on. Business owners are brilliant at their craft, but far from it on the business side of things. Many business owners wish they could offload the whole “run the business” piece of their life and focus on what they do best. That seems an awful lot like what people do in their traditional jobs.

I love small business. It’s rewarding, it’s hard, and it’s exciting. I can’t imagine doing anything else at this point in my life. However, at the same time, I recognize it’s not for everyone. I wish we, as a culture, would stop elevating it as the be-all-end-all for everyone. It’s not. For many, their traditional job will be their very best life…..and they shouldn’t feel one ounce of shame for that. Embrace it, enjoy it, and do your good work!

* We published a podcast episode about this topic almost two years ago. It’s titled 016 - The Toxic Notion Everyone Should Aspire to Be Their Own Boss. You can find it on APPLE, SPOTIFY, or wherever you get your podcasts.