Why Being an Entrepreneur is Hard

Lately, I am obsessed with all things Enneagram. For those of you who have not heard about this amazing personality typology - let me give you a super quick breakdown, but trust me, you are going to want to check out more for yourself later.


The Enneagram helps categorize different personality types with nine different indicators. Each type has a name or identifier. What I love the most about the Enneagram compared to other personality tests, it helps to reveal the good, the bad and the ugly about your personality. Other tests I have taken in the past highlight the majority of the good stuff, and that’s about it. This is different. I have discovered different stressors or “triggers” as I call them that are a part of my personality type. I mainly view this as an attempt at a proactive way to handle some of the things that can turn my attitude sour.

So what’s my type, you ask? It took me a bit to figure out, even though looking back it was pretty obvious. I am a Type One: The Perfectionist. Pretty telling, don’t you think? Should have known!

Anyways, here’s the point of today’s post. My personality type and the whole “entrepreneurship” thing can be a dangerous mix. Here’s why.

Being the perfectionist that I am, I obsess over things. Mainly over the wrong things. I read too much in between the lines and think of every worst possible scenario possible. I respond too quickly to “problems” when in reality there was no problem in the first place. I can take on too much and worry too much because I want everything to be perfect.

Sure, most perfectionists deal with these things on a daily basis. Here’s where it gets dangerous as an entrepreneur. Being that my business is literally me - I always feel the need that everything has to be top notch. Honestly, I understand that no one is ever perfect, but man, I sure try my hardest to come close. I always feel like I have something to prove. I always want to serve my clients to the best of my ability. I don’t want to let anyone down, even if it means letting my loved ones down by obsessing of a client email or worrying about a deadline that is forever away.

While I HATE being told to relax (this only makes it worse for me), I need to give it a try.

On my recent birthday trip to Charleston, Keith and I went to a couples massage. About 20 minutes into the bliss of relaxation, I started thinking about a copywriting project. I mean SERIOUSLY?! I can’t even get my brain to turn off during a couples massage.

I tell you all of this, not to get sympathy or anything like that, I share this with you to be REAL. While authenticity is such a flippin’ buzzword lately (thanks, Instagram), I want my readers and followers to understand the reality of business. I get a few emails a month from people wanting to start a virtual assistant business or begin freelancing. I think the desire to be an entrepreneur is excellent, but I want to warn you. Keep your priorities in check. Make sure you know your triggers. Learn more about how you handle conflict and stress because trust me; you are going to be facing a lot with your business. It can be totally worth it all, but you have to be careful.

Want to learn about your Enneagram type? Take this online quiz, then read this book for even more information! Plus, you HAVE to check out this fantastic podcast from Sleeping at Last about the Enneagram as well!