be your own boss

i don’t want to be my own boss

world's best boss

Are you entrepreneurial? I’m not. I’m just not and I am completely ok with this fact. Some people have a deep desire to direct their own destiny and set their own hours and be their own boss. Certain aspects of being an entrepreneur appeal to me. Is there anyone that doesn’t find the idea of working from home and setting your own hours appealing? But as I approach 30 (I’ll be 29 this summer) I’ve become more accepting of myself and one of the things I’ve accepted as truth is that I operate really well inside boundaries, especially if someone else set those boundaries.

Work provides me with the structure and a set of expectations and I function really well inside those clear expectations. I also really appreciate someone else signing my paycheck. I don’t want the responsibility of making enough money to pay myself.  While I am grateful to know that I operate best with outsider expectations sometimes I am critical of myself for not being more entrepreneurial and taking fate in my own hands. The employment market trends all point to the fact that employers are more and more moving towards independent contract workers. Where does this leave someone like me who prefers to have a boss?

Honestly, it leaves me a little scared. I understand the move towards independent contractors’ from both an employee and employers’ perspective but understanding it doesn’t make me less scared to face the changing landscape of employment. My current employer is very traditional. Along with a 40 hour work week I receive health benefits paid in full, a pension fund with an optional 401K, flexible health spending account, paid vacation, paid Holiday and overtime paid at time and half – all benefits you would assume you would be getting if you worked at Sterling Cooper in 1963.

If I were to leave and strike out on my own all those traditional benefits would disappear too. The movement to entrepreneurial work is incredibly apparent on the internet today. Boutique shops and personally crafted goods can be found everywhere, not to mention all the blogs turned business and independent creative services offered. The shift is notable and powerful. This monumental shift in the way people present their wares and talents to the world is inspiring until I think of all the benefits I would leave behind if I left the traditional work paradigm I currently have.

I’m not thinking of leaving my job – we need the money to live on while we pay off our house. But I have been day dreaming of ways to make extra money during weekends and at night. Weekend and night entrepreneurial pursuits seem a good way to dip a toe in the scary water for me because I wouldn’t have to leave behind my traditional benefits. The gravitation towards entrepreneurship makes me feel old-fashioned for liking the structure of a 9-5 job.

What about you? Would you love to be your own boss or are you left wondering how you will fit in the brave new landscape of contract work? Are you your own boss now? How did you transition? Any suggestions?