This may very well wind up being the most ironic post I make to this site as a serial entrepreneur who has a goal of personal freedom. After nearly a decade of self employment, I have once again come to the conclusion that I need a job. You see, this isn’t the first time that I’ve realized this. Oh no. I have shared several times in the panic and anxiety that entrepreneurs collectively call ‘feast or famine’.


This kid gets it.

In the past, each time that I have come to this conclusion… I have always viewed getting a job as the worst thing ever, and only reluctantly and as a last resort would I pick up something full time for a short period and fly like the wind as soon as business picked up again for my own gig.


This is the stuff that dreams are made of.

As a self employed entrepreneur, I am responsible for … well… everything. Not only do I need to come up with the money every month for my own mortgage or rent, electricity, phone bill, food for my family and pets, car expenses, clothing, insurance, doctor bills… everything that it takes just to live, but I am also responsible for paying my contractors, my hosting bills, software licenses, business insurance, accounting, taxes, telephone bills, hardware / computer expenses, bookkeeping, everything that is needed for my business to survive. Not to mention all the time that it takes to deal with all that stuff if you are the only one doing any of it.

I can’t count the number of times that our personal savings has gotten wiped out in order to pay for business expenses during lean times. It gets pretty tiring.

The last time I struck out on my own, it was after getting laid off back in 2009. Nearly 5 years later, I am realizing that I did not have enough of a platform to launch from at that point. You see… because I started my business from a weak foundation, I have not been able to say no to any paying work. Don’t misunderstand me, I am not ungrateful. Quite the opposite! I am so very thankful that I have had the opportunity to serve my clients! However, there has been a lot of work over the years that I have taken on that did not always fit the vision for where I wanted my fledgling company to go, and as a result of this, I have not had the freedom to really be able to steer the ship and instead have allowed it to be carried along with the current of whatever brought cash in the door. The pressure to say ‘yes’ to everything is enormous, and it can hinder your ability to negotiate agreements or even request payment from your clients when they fall behind.

He has no problem saying no.

He has no problem saying no.

So… I’m going to try something different this time. I’m going to get a job and keep it, and I’m going to focus on building a business and systems that don’t require me to work full time unless I want to. This is, after all what my end goal for personal freedom will require anyhow, right? What do you think?