First, it was the mullet haircut.
(Yes, I rocked the mullet. The good ol’ days.)
I had no choice, I tell you.
Next, was the spiky hair.
That was my doing. And let me tell you, my hair was perfect.
Shower, blow dry hair, then put enough hair product to force my hair to keep shape so it could survive 60 mph winds. Oh, and not only withstand forceful winds, but also keep form perfectly.
Fast forward. During 5 months of travel, I shaved my head.
Fast forward. Then it grew out and I experimented with many stylists to see what they think “works best on me.”
Today, I woke up, took a shower, no blow drying or hair product, and it just works as it is.
You may be wondering, “How does this have anything to do with entrepreneur insecurities?”
Hold tight.
My hair style has deeper meaning.
My perfect spiky hair needed to be perfected because, unconsciously, I believe I was afraid of being identified with anything less than perfect.
Why?
Tying my external behavior (my perfect hair) with my identity (my sense of self-worth) feeds into shame.
The thinking: if my hair is perfect, then I am perfect, and if I am perfect, I am worthy of connection with others.
Going the depth, getting down to the roots
Shame is fear of disconnection from others. Some entrepreneurs are driven by it.
The journey of my hair reflects the evolution of my life.
When my hair was perfect, what was I doing?
I was overcompensating for something much deeper. I felt insecure in my skin so I controlled my hair so that I would appear perfect.
To feel insecure is to lack confidence or to have self-doubt. From Wikipedia, it’s "feeling of general unease or nervousness that may be triggered by perceiving of oneself to be vulnerable or inferior in some way, or a sense of vulnerability or instability which threatens one's self-image or ego." And so we’re clear on vulnerability, the context here is vulnerable as in not having the ability to withstand the effects of a hostile environment (Wikipedia).
Insecurity has roots in fear. Fear of being vulnerable. Fear of instability. This biological fear we create within the mind threatens our survival.
To overcompensate is to take excessive measures in attempting to correct or make amends for an error, weakness, or problem. Overcompensation can be toward the thing that is lacking, or something else to distract you from dealing with the deeper cause (which may be inferiority). Overcompensation is only positive when you see what you are doing and you follow your curiosity to uncover the root of the issue.
Let me say that again: my insecurities surfaced as overcontrolling. I overcompensated.
This isn’t black and white, and perfect hair does not always equal insecurity... but it’s one data point that spilled into my entrepreneurial life.
This truth revealed itself when I found myself asking, “What do I get out of doing this?” Or more specifically, what do I get out of trying to control people so strongly? This metacognitive act helped me see what was really happening.
I’ve done a decent job controlling my environment, too.
I’ve been self-employed all of my life and a majority of my work has always been remote. I value freedom. My businesses and work have ranged from managing IT systems, Linux server administration, web development, focus in mobile web development, all mostly launching and working with startups.
In 2004, I hired my first freelancer for a large project and worked with dozens of freelancers over the years. In 2011, I hired my first full-time employee.
What’s interesting is how my insecurities showed up in the way I lead.
I tried to control people like I controlled my environment.
Simple enough, right?
If I (we?) overcompensate for what we believe to be errors, weaknesses, or problems, then we often end up trying too hard.
Entrepreneurs and their insecurities
We each only have the authority to speak over our own lives so I want to be clear that I’m not making a generalization, only an observation based off my life experience.
If we overcompensate for insecurity, then we instinctively try to create security around us – regardless of whether or not it’s even possible.
And that’s the power of many entrepreneurs.
Entrepreneurs proactively create something from nothing. That’s a gift. It shows one is able to control their surroundings to bring about what they want. Most people do not instinctively have this skill.
The question I ask is: is this proactive skill and ability to control optimized?
In the past, I’ve written about optimizing the mind for legacy and to master your psychology. I share an example of driving my car at 160 miles per hour on the freeway. That would maximize my engine’s capabilities. But don't be fooled. It would be unwise and unhealthy for my car’s engine and for those driving the regular speed limit around me.
The same is true with controlling our environment (including the people in them).
The wisdom lies in being mindful of what we’re doing.
How about the uncertainty of a startup?
Uncertainty of a startup can also create an insecurity. Entrepreneurs may feel insecure because the reality is startups are very uncertain. This truth can be fought, or it can be accepted and embraced and it can strengthen the foundation of the founder so they can execute against their vision. It’s a mental muscle.
In “Finding Success in Failure: True Confessions From 10 Years of Startup Mistakes,” by Craftsman Founder Lucas Carlson, he says, “You can use your uncertainty as an advantage by making choices that allow your startup all the flexibility it needs to be re-invented.” I love it, play to your strengths. I want to see more founders do this objectively so that their impact is greater.
The short-term impact of entrepreneur insecurities
In the short-term, an entrepreneur may be able to find a team that they can exert a great deal of control over. Instilling fear (and weakening legacy) through dominance only breeds more fear. Fear enables survival.
As an entrepreneur, do you want to leave your team in survival mode? I don’t.
Sure, it’s easy to throw some weak people together, exert control, and get them to build something for you. Maybe you’ll get some traction in your startup. Maybe you’ll even score a big exit and make a lot of money.
An insecure person who overcompensates unknowingly by forcefully exerting control over others prevents those around them from feeling true inner security. Feeling secure is the basis of true living. This is about more than surviving.
What do you want for your team and those around you? Family? Friends?
I exist to inspire legacy. Legacy is your value to humanity. It’s your impact on those around you when you're not in the room.
In the short-term, forceful dominance over others can work. Get some traction. Make a quick buck.
But how does it inspire legacy?
Well, it doesn’t pave the way for growth. It weakens legacy. The only “strong” person in that picture is the person exerting dominance (with false strength).
This isn’t some fluffy concept or theory. This is about becoming more human.
Animals don’t have the capacity to transcend their animal nature.
Humans can transcend our fear survival instinct by strengthening our mental muscle. Insecurity is tied to anxiety which is also rooted in fear. Anxiety is the result of an overstimulated amygdala, or an overstimulated fight or flight response within the brain. Research from anxiety expert Paul Foxman states that this is common in people who are sensitive to their environment and have certain personality traits.
Where I’m going with this: Objectively speaking, this isn’t good or bad, it simply is. I am asking you: how do you want to take the next step?
The long-term impact of entrepreneur security
Notice the language: “entrepreneur security.”
I’m talking about the entrepreneur who feels confident in their skin. True confidence. True sense of deep inner security. This is the evolved state.
Great entrepreneurs who maintain a deep inner sense of security are able to more objectively experience the world around them.
This evolved leader has unpacked the past to strengthen the foundation for their future. This is the person who cares about those around them and the legacy they intend to live.
The secure leader has the courage to be vulnerable. But wait, let’s redefine vulnerability here to vulnerability researcher Brené Brown’s definition: uncertainty, risk, and emotional exposure. This is a strength for startups. Brené would also say that the foundation of creativity, change, and innovation, is vulnerability.
I value creativity, change, and innovation. I value it for myself and within my company. Do you?
When my conviction for why I exist is to inspire legacy, it helps me move through whatever discomfort I need to so that I can master my psychology.
To master your psychology is to have the level of self-awareness that allows you to optimize your effectiveness. This is about making sure your beliefs about life and yourself serve you so that you can experience growth in your startup, create jobs, and impact the world. It’s easy to say we want to better the world. It’s not so easy to better ourselves. Simple, not easy.
Do you care about how your insecurities affect your startup? Learn about our introspective experience.
