Why Being a Entrepreneur is Ego Deflating

Before I started my own company, I was extraordinarily confident in all of my abilities. I firmly believed in my superior skills in almost all areas. What was this belief based on? Not an awful lot – working for someone else in a narrowly defined job position, breezing through college as a finance major at UW, and not having really felt challenged previously.

Enterpreneur Overwhelmed

Three and a half years ago, I made the leap to start my own business. Running your own company is a great exercise in humility; experience has been a brutal teacher with a big club ready to smack me every time I make missteps.

When you work for someone else, you can focus in on what you excel at. If you are an accountant, you do accounting all day long and you get really good at accounting work. If you are a salesperson, you spend all day talking to people and sending out proposals and build up a lot of talent there too. If you are a programmer, you just pump out code until you can code in your sleep. As an entrepreneur though you must do EVERYTHING and do it at least decently well.

Here are some of the types of job roles I’ve been forced into as an entrepreneur:

  • Legal
  • Taxes
  • SEO
  • Janitorial work
  • Human Resources
  • Programming
  • Accounting
  • Website design
  • Marketing
  • Customer service
  • Finance
  • Sales
  • Company psychologist
  • Contract negotiations

Let me tell you – doing all of these different job roles quickly brought quite a bit of humility. In my first year, I was sued by an outside sales contractor who I had fired and because I didn’t have a clear contract I lost a LOT of money. I did my own accounting and taxes and invoicing and discovered that I wasn’t that great at keeping the books. I started out being a pretty poor salesperson and had to hustle hard to get a few piddly contracts. My client management skills were atrocious – I sent no reporting, had no follow up calls, and did not have good scopes of work. Pretty much everything that I had prided myself on I discovered I had a LOT of work to do to improve.

The following three and a half years have been a crash course in pretty much everything related to business. And I still have a very long ways to go. Just gotta take it one day at a time.


Published by

Joel Gross

Joel Gross is the CEO of Coalition Technologies.

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