Guest Blog: Kyle Thompson on the challenges of running a small business

The Challenges of being an Entrepreneur: The Things they don’t tell you about running your own business.

It’s hard to know where to start on the challenges of running a small business, as each industry is a little different. However, there are a few challenges that are universal- with no one to tell you what to do, it’s hard to know what to do! I’d like to say I am someone that thrives on chaos and uncertainty, and am comfortable and productive without structure, but that would be total BS. I keep pretty much the same schedule and structure every day; I get up at 5am, do housework before going to the gym, and then get started with work around 9. I do this because once I start working I can’t really stop. It feels like there is always something else to do, because there is! You are never really done for the day as a startup business owner, you simply just give up and pick back up where you left off the following day. It’s hard to take a day off, because all the work left undone looms over you, and having an anxiety disorder does not help this feeling.

The only way to deal with this is to impose structure on yourself… and I hate structure. I had this romantic notion of entrepreneurship where I could “float” through the day and handle things as they come. Instead, I have my entire day structured in 15 minute slots so that I can remain sane and on-track. The “freedom” you get as an entrepreneur is a double-edged sword, since even though there is no one telling you what to do, you will fail if you can’t impose structure on yourself.

Another universal challenge of entrepreneurship is self-doubt. I have moments where I fear I’m not good enough, that I’m not trying hard enough, that I’m not cut out for it and that my business will fail, and that I will be a failure myself. Fortunately, this is both normal and a good thing. If you don’t feel this way from time to time, you are either ignorant or arrogant (or both). The reality is that a lot of businesses do fail, and that those that do succeed are often rollercoaster rides that never really end. There will always be highs, and there will always be lows. You have to be humble enough to know that you will make mistakes, yet confident enough to get through them. This is not an easy thing to cope with, so if your tendency is to jump ship the moment things get hard, don’t start a business.

The final piece that tends to be universal to every startup or small business: chaos and complexity. Nothing will go according to plan, and everything will be more complicated than you expected. I never expected there to be so many moving parts to my business, nor did I expect to spend so much time refining systems and processes that control the day-to-day operations, such as client onboarding, communications, marketing, etc. Things are still far from perfect, but I have come a long way since launch. It has been through a process of trial and error (mostly error) that I have made these improvements, and I regret not hiring a coach, who could have kept me from making a lot of these mistakes in the first place. It seemed like such a large upfront expense, but it has ended up being one of the costliest mistakes I have made.

I hope this short article gave you a more realistic outlook on small businesses. Entrepreneurship is so romanticized in American culture that many of us think of it as the obvious path. If you look at it as the “easy way out”, you are doomed to fail. If you can’t handle short term setbacks, you will fail even faster. Bottom line: if you consider yourself a sane person with good experience and credentials, it might not be the best idea. But if you are as unemployable as I am, you may not have a choice.

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