Entrepreneurship: Real Talk About Becoming an Entrepreneur

Being an Entrepreneur Is Hard Work

Let me start by saying this is not a banner ad for becoming an entrepreneur. In fact, if you’re hesitant about joining the entrepreneurial community, you should probably stop reading right now.

This is about the hard part of being an entrepreneur. I always tell kids graduating from college that for any job, as long as they really like 10-20% of what they do at work, they should be really happy with their job. Entrepreneurship is no different.

That being said, starting your own company and being your own boss is fantastic. I would absolutely never go back. I should say that given a successful company and some way to pay myself by being self-employed, I would never go back. But does that mean that I love every single thing about being an entrepreneur? Of course not.

The Tough Parts of Being an Entrepreneur

As much as I love being an entrepreneur, there are many things that aren’t very fun about it. You could talk to any entrepreneur you know and I can almost guarantee they could easily list off the things that they don’t enjoy about entrepreneurship.

Let's dig into the not-so-positive side of entrepreneurship

First, there are the basics of starting a company:

  • Incorporating your business and all of the other fun legal things
  • The joy of filing taxes
  • Accounting
  • Insurance

Then you get to do something that might actually be exciting if you like this sort of thing and that’s hire additional people to help you build your business.

After that, you get to do some more not-so-fun things:

  • Manage other humans and keep them both motivated and engaged
  • Figure out payroll and workers comp insurance
  • Remove other humans from your company when they are no longer working out or aren’t a good fit for your business

And as you grow you get to:

  • Pay what feels like an endless pile of bills
  • Worry about cash flow
  • Register in various states for sales and personnel reasons (and discover how antiquated most states are)
  • Deal with miscommunication (and expectation gaps) with customers
  • Try to figure out the intricacies and work through the bugs of off-the-shelf software that you thought was going to solve all your problems

Is Becoming an Entrepreneur Right for You?

A truly exciting thing (especially for lifelong learners) is you get to learn new things all the time. A less exciting thing is that many of the things that you get to learn you really wish you had never even heard of.

Oh, and if you avoid dealing with any of the things listed above, you get to find out about tax audits and deal with the fines and penalties for not learning about them.

If you can overcome the hurdles of the boring, painful logistics of running a business and get the business to a sustainable size where it’s paying you and all of your key employees well enough to keep you excited, you can probably pay someone to handle much of the day to day in the back office —YAY!!!

Then you’re probably going to start dealing with some growing pains… like scaling and raising debt or equity capital and reporting to stakeholders.

There are days when I wonder why I started a company. And this is after 4 years and we have great traction, an incredible team and really happy customers. But sometimes, just sometimes, I just wish I could show up and get a paycheck without all the other things that go along with being an entrepreneur. Just one job rather than 45 different jobs where I constantly feel like I’m just a little out of my depth.

But at the end of the day, I know this is the right path for me. If this “real talk” doesn’t scare you away from becoming an entrepreneur, welcome to the club! It’s not the most glamorous one around, but at the end of the day it can be truly satisfying to know you’re doing something to better the world just a little.