The Emotional Challenges and (Sometimes) Trauma of Being an Entrepreneur - That No One Tells You About

A personal narrative about the importance of self-mastery if you're a self-employed creator.

If you’re an entrepreneur, I think you’re going to enjoy not just this story, but my dissection and discussion of the issues that one has to face and surmount as a solo creative or entrepreneur.

If you’re in a career or job where you’re employed by someone else, this may still interest you.

Whether you’re considering entrepreneurship, you should be able to relate to the emotional challenges by reframing them to match your own work situation.

There’s a big, ugly list of all the challenges one must face as an entrepreneur.

It’s the sort of list people want to avoid sharing with an aspiring creator because otherwise, you wouldn’t dare take the leap. The excitement and the pros of having your own business, or working for yourself, sell so easily and to the point of deception.

Full transparency: I am still moving towards my dream, so I have no business or immoral reason to “sell you the dream of being your own boss.”

What I do want to share with you is the drama that goes on behind the curtain. My intention isn’t to scare you off, but to share my truth and the fact that I am still hopeful, intentional, and motivated to accomplish my dreams — even when things get unbearably challenging.

You need a fucking stupid amount of unwavering belief, faith, and blind hope in yourself.

I’m talking about a belief that is so stupid your friends will look at you with wonder and concern that something is wrong with you — that maybe you didn’t think this one through.

You will be faced with the need to take risks, to be vulnerable, to go without money for long periods of time, to possibly go bankrupt, to have to borrow from your parents, your lover, your friends, to let your credit card to go unpaid, to wake up in the middle of the night with anxiety attacks, and so on.

You will have to face the haters both publicly and privately who will tell you that you’re wrong, stupid, out of your league, or just a dreamer to think that you can make it.

The Catch-22: The Biggest Threat to Your Success Is Yourself.

You will hate on yourself.

You will break down in tears.

You will spend days half-asleep, wondering if you should take drugs or open another bottle to escape the reality you’ve created for yourself.

You will avoid reaching out to friends because you want to avoid feeling like you’re complaining — or constantly talking about yourself and your business — when (usually) all they really intend to do is just listen and be there for you.

The outcome of the misery and frustration is what the experience will make of you.

There are days when you will feel deflated to the point of being crushed flat by the weight of your fears and concerns.

Those days are best served in bed, covers pulled up over your head, or in a hot bath, without human interaction or any responsibilities. They are repeated rites of passage that, if you come through on the other side, strengthen your resolve.

Still want to be an entrepreneur?

The above is a journal entry from 2018, which I’ve edited slightly. I still face many of the challenges of being a creative entrepreneur. However, I have since greatly improved by taking appropriate actions to minimize emotional stresses and challenges.

I was reminded of an even earlier journal entry from 2015 that demonstrates my lack of self-mastery at the time.

I’m having a crisis of faith.

Last night, I was in the hot seat for my MasterMind group. I had sent a document requesting thoughts and brainstorming on my book topic, “5 Health Mistakes Executives Make and What to Do Instead.”

After the call, I was angry. My partner asked how it went, and I said, “Awful.” I couldn’t talk about it. Instead, I went to sleep rigid with anger and of course, slept like shit.

What happened?

I asked for feedback and brainstorming on my ebook draft. I provided talking points, so I could get clarity and reign in my thoughts. Furthermore, I hoped I’d get some great ideas from the four other busy guys on the call.

From two of them, I got useful support and questions about whether a book was the best method to reach busy executives. We discussed recording a video, which I see as an option, and given how busy people are, I would like to offer multiple formats, e.g., a book, audio, and video.

But from two of the other members, I was told, “An ebook won’t work here. You need to do what Pat Flynn is doing” — referencing a 2-year-old webinar that’s basically an affiliate up-sell to LeadPages.

What really hurt me emotionally is my attachment to writing. I love to write. I want to communicate in books and articles. To suggest no one reads free ebooks anymore is annoying. Just because he prefers to watch a video doesn’t mean my strategy is wrong. Nor does it mean I’m right either!

The lessons learned.

It was really hard for me to remain pleasant during the group call. I wanted to hang up at the halfway point, but I sucked it up and made notes about what, I thought, was valuable.

But I doubted myself afterwards. So much so that I went from physically rigid anger lying in bed to almost wanting to cry as my partner stoked my arm, knowing I was upset and reaching out to calm me.

Everyone has their own fucking opinion. Yes, I’m still pissed. Nonetheless, sometimes there is great value in the opinions of others, it just depends on whether you can use their feedback or not, and whether you have expressed permission that you want critical feedback.

My mistake was in not taking control of the conversation to tell the group I wanted to brainstorm, instead of letting them go into what they thought was wrong with my idea, or how I could do it better.

Suffice to say, I’m going to take a break from writing the ebook today. I can’t face it right now with the still-lingering self-doubt.

Lastly, I think I need to break from my MasterMind group. I have to consider what to say, but I’m thinking I will say I’ll break for the summer and consider if I wish to continue for the beginning of September.

And it’s not because they are mean or unhelpful. Rather, I joined the group for a reason and to follow a system to see if it would help me get what I want with my business.

Whatever You Choose to Call Self-Employment, You Can’t Do it on Your Own.

After the stories I’ve told you, this would seem like a paradox.

If you don’t partner with others, with a coach, a mastermind group, a community, or a meetup group, you will either suffer from ignorance or incompetence.

Ignorance is not knowing what you don’t know. Incompetence is lacking skill in a particular aspect of running your business. As long as you’re not being willfully ignorant or incompetent, you can improve your situation, increase your potential, and solve your challenges when you solicit the help or guidance of others.

In any relationship, whether personal or business, we need to come from a place of respect.

Going out on your own can be a risk that causes the kind of emotional stress that makes it difficult to work with others because you may always feel like you’re on the defensive (like my story). Self-awareness is key, as is taking the time for self-examination to understand why things went poorly and why things went well.

If you’re struggling with what you want to create or facing a major obstacle, let’s meet for a discovery coaching session. I’ll help you get enough clarity to determine your next action steps and get back on track.