It’s fun to parade around flying our entrepreneur flags. During my former life of depression and social anxiety driven by the self-awareness that I was squandering my life in a mind-numbing job, I witnessed a snippet of a conversation that was deeply etched into my brain. While standing in line waiting for my moment of interaction with the next available barista, I heard a female voice ask the eternally obvious, “what do you do” question. The guy the question was directed to responded, “Oh, I run my own company.” I don’t know if she disrobed and knocked over a table of lattes by throwing herself at him or not. I was too wrapped up in my own contemplation of his answer. I wanted that that answer for myself.
This wasn’t really a moment of revelation. I’d been obsessed about being an entrepreneur since people started asking me what I wanted to do and I never had an answer. The point is that I’ve always placed entrepreneurialism on a pedestal. I never really questioned that it was the ultimate “job”. So… I’m questioning it now.
Am I an entrepreneur because being an entrepreneur is super awesome and I’m super awesome so I should be an entrepreneur? Or… Or.. Am I an entrepreneur because I’m just a huge mass of insecurity? Let me explain my quandary.
There are some things I hate about jobs and the process that being an entrepreneur allows me to completely avoid. They aren’t really rooted in anything even close to positive or excellent. So, while I’m not relinquishing my adoration of entrepreneurialism, I wonder how much of my motivation falls on the positive side of the spectrum and how much falls on the dark, negative, insecure, avoidance side.
On the meta level, being an entrepreneur essentially allows me to talk myself out of doing absolutely everything I don’t want to do. EVERYTHING! It’s the ultimate mechanism for rationalized avoidance.
More specifically, being an entrepreneur allows me to avoid:
- Interviews. Interviews suck. Not only do interviews have a way of reducing my vocabulary to monosyllabic drivel, studies pretty much tell us that making hiring decisions based on them have no correlation to future job performance. So rather than be subjected to such nonsense, I get to ramble on about how stupid they are and con myself into thinking pitching ideas to clients or investors is much different.
- Control. Being at the mercy of the whims of another drives me nuts. I hate feeling like an automaton. I wouldn’t say I have a control-freak type problem where I have to control others. It’s more of the reluctance to be managed by incompetence. Guess what? I get to build a nice little cocoon of control around my entrepreneurial world. Score another one for avoidance.
- Authority. This sounds similar to control, but it’s an entirely different issue for me. I’ve always had a weird feeling around people of authority. This has included parents of friends, teachers at all levels of education, bosses, bosses of bosses, police, et cetera. I find myself hitting the brakes when passing cops at the posted speed limit. Watching lie detector tests on TV makes me feel guilty and nobody’s even asking me a question. There’s no rational explanation for this that I can discern. I’d consult a therapist, but for all I know, I’d weird out when I saw their degree on the wall.
- Public failure. Public may be an overstatement, but being an entrepreneur is a great place to exercise the “succeed in public, fail in private” axiom. While affecting the probability of failure comes and goes, mitigating the risk of people witnessing the magnitude of failures is often super easy. Minimizing the number of people even informed of failures is often possible as well. I rarely have to deal with failing in front of co-workers.
I’m sure there are tons more. These popped into my head without much introspection at all. I try to be in-touch with my weaknesses, so maybe that’s not remarkable.
So what’s your deal? Do you think you’re a pure entrepreneur doing it for all the right reasons, or are you extra motivated to succeed as an entrepreneur so you don’t have to face the nasty parts of your personality?










Brandon W.
4 months ago
Many of the things you write about yourself ring true for me, as well. I have no tolerance for tedious bullshit. In my last job, I was paid 40 hours a week to do 3 hours worth of crap that was assigned to me, which were things that the assignor should have just done for themselves in the first place. Many things took longer for them to assign to me than it would have taken for them to do themselves, in the first place. I figured out ways to do things more efficiently so that I really only needed 3 hours a week to do the job. But this is how I feel about most jobs; and I've re-designed every job I've ever had into 3-10 hr workweeks (for which I was paid 40). Sounds nice, but it's fucking torture. It's like being in a prison cell for the remaining 37 hours of the week. Not to mention being required to drag ass up at 6am to be at a desk by 8am.
And that's how I feel about jobs. Most people are unnecessary, and those that are necessary are disasterously inefficient about it.
This isn't to say I won't work hard when necessary. When working in television I'd sometimes put in 84 hour weeks and enjoy it. As a full-time professional photographer I'd put in 14 hour days with few breaks and still be energized at 10pm. It's just that so much “work” is unnecessary, tedious bullshit. And I don't want to do it anymore.
When I was young, I wanted to be an optometrist and have my own office. When I was in high school I wanted to be an independent day trader. I went to college and decided I'd much rather be a television producer and head up my own creations. I fell in love with the creative aspects of lighting, went to do that in television and extended it into photography. I've never had any aspiration to work for someone else, have the (theoretically) “secure” job. I went back to college and studied business and marketing; not because I wanted to work for anyone, but because I wanted to understand business processes, market identification, and promotion. I went on to do a Master's degree – mostly for myself, not anyone else – and what did I do my thesis on? Entrepreneurship.
It's just in my blood. I don't have it in me to be a robot in someone else's machine (and especially not a pointless robot). I want to build the machines.
Twitted by NomadRip
4 months ago
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Andrew MacPherson
4 months ago
I love hearing others' perspectives and experiences. The part about succeeding in whittling your job down to 3-10 hours, but still hating it is a great insight. I'm sure there are a lot of people out there who think replicating your process and working that much less would cure all of their problems. For some, it might, but when you add the counterpoint about having seemingly boundless energy working way more hours, another dimension arises. For you, it seems like creativity has a lot to do with it. That's probably true for a lot of other people too. Unfortunately, many never find out because capital 'C' Creativity is framed as a rare achievement only available to a select few.
This kind of feedback and sharing of similar experience is invaluable. Thank you so much for the contribution.
Andrew Caldwell
3 months ago
Definitely to avoid all of the corporate fluff and bullshit! So unecessary. Although it was a lot easier to waste company time checking out blogs than my own!
Went into the city the other day, shorts, t, thongs, was getting stared up and down by corporates like i'd stepped on poo! Admin girls, clerks, anyone. They should be having a red hot look at themselves!
About the 'avoiding public failure – being an entreprenuer', this sort of rings true if you're doing it in secret, just wish i hadn't made the fatal error of announcing it to the world on a website!
Keep the posts coming Andrew
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[...] “Entrepreneur: Insecure Avoidance“, I wrote about some potential psychological issues that may contribute to our tendency to, [...]