How a lifetime of proving yourself can plague a pursuit for freedom through entrepreneurship

The first time I read Carol Dweck’s book Mindset, I was finally able to make sense of the looming question of my life:

“I was a perfect student. The perfect employee. In every organization I was ever a part of I received glowing feedback and reviews. So why did I keep ending up here?”

Here being any number of situations where I was working a job that left me completely depleted, at the bottom of the pack, certain that I was capable of more but no idea how to see that through.

I went to business school for entrepreneurial management, graduated with a near perfect GPA, and proceeded to spend the next 6 years in retail management positions that left me completely overworked and underpaid every, single, time. And in almost every place I ever worked someone would look me dead in the eye and say something along the lines of “you don’t belong here”. It wasn’t that they didn’t like me or didn’t want me there — but it was like we both knew I was meant for something else.

I never felt like those jobs were below me (and I still don’t — retail is not easy) but there was never, ever a part of me that thought “yea, this is where I belong.”

I was desperate for something more, my ability seemed to have been proven, and yet, there I was. Stuck in a rip tide that I couldn’t break out of.

In Dweck’s book Mindset, she lays out the difference between a growth mindset and a fixed mindset.

Someone with a growth mindset believes that through effort and challenge they learn, grow, and can develop skills and ability over time.

Someone with a fixed mindset believes that their qualities, skills, and abilities simply are. They are fixed and can not be changed.

Dweck explains that someone with a fixed mindset will find themselves perpetually trying to prove themselves and routinely find themselves as the “big fish in a small pond”. Why? Because for someone with a fixed mindset, not being good at something seems to reveal something about their inherent nature. So life becomes a game of arranging successes and avoiding failures — thus avoiding any opportunity to “find out” just how unremarkable they are.

When you’re in a fixed mindset, it’s all about proving yourself. There is no room for mistakes or learning. There is only room for perfection. And one way to deliver perfection — set the bar low enough that you can guarantee you will clear it.

It all made sense. I was in a practice of setting the bar low and clearing it perfectly so I could protect my ego and avoid finding out that I wasn’t perfect. Sounds harsh, but that’s basically the gist.

It wasn’t that I couldn’t leave my job and start a business like I had always wanted — it was that I couldn’t leave my job, start a business, and guarantee that it would all unfold seamlessly and without struggle. And what would it mean about me as a person if I stumbled, made mistakes, couldn’t figure it out, or failed? How would I survive if I found out I was actually just a totally average, run-of-the-mill person who didn’t know shit about what I was attempting to do? What would I do if I didn’t feel special?!

If you’re reading this, feeling as defensive as I was when I first read Dweck’s work, it might help you to know that there aren’t fixed mindset people and growth mindset people. We all fluctuate between the two and we can learn to embrace challenge and shift into a growth mindset. I’ve been working on that for the past 2 years or so.

But there’s something else from those years of trying to prove myself that has been far more challenging to shift.

As someone who was on a constant quest to prove myself, I considered stress, exhaustion, and a constant eye on my to-do list to be reliable guide posts. If I was tired, hyperaware, worrying, and stressed out, it probably meant I was performing. Being relaxed, forgetting about work, or having energy left at the end of the day meant that I was probably missing something or was letting someone down by not pulling my full weight.

Hustling felt safe. It gave me a false sense of control over my performance. And since I was operating according to a belief that my performance was a reflection of who I was, this feeling of control seemed to be very high stakes. Being in control of my performance was the only way I knew who I was, and the only way I knew to belong.

The reverse side of that coin meant that relaxing actually felt unsafe. The feeling of being caught up, or not even thinking about work, or choosing not to care for any period of time would send me into a minor state of panic. I would find myself thinking “what am I missing?” or “what did I forget?” or “my co-workers are stressed. What will they think about me if they know I’m over just chilling?”

That pattern of checking myself when things feel too good is something that Gay Hendricks refers to as The Upper Limit Problem. It is the pattern of sabotaging ourselves when things are going well to bring ourselves back down into a comfortable range of emotion that gives us a false sense of control and protects us from vulnerability. The result is that we perpetually channel available energy into unnecessary worry, doubt, and conflict, and away from our creative pursuits — thus keeping ourselves out of our zone of genius.

Here’s where fixed mindset and the upper limit problem culminate into a pattern that plagues a certain type of lifestyle entrepreneur.

Entrepreneurship provides an opportunity for autonomy and freedom that is tough to match. But when feelings of freedom and ease actually feel unsafe, these desired feelings can trigger a response to hustle, do more, and work harder. While hustle is not the conscious desire, the conscious desire for ease is easily overrode by a mind and body that have been trained to recognize hustle as safe and relaxation as unsafe.

Slowing down to assess options, reevaluate the path forward, take the appropriate amount of time to make the best decision, or take the 3 day weekend that was supposed to be one of the main perks of owning your own business can trigger actual feelings of panic. It can cause us to take off into future-trip that leads to our inevitable demise, because our mind and body have spent a lifetime operating within a false reality where hard work is necessary for survival.

Building a business that offers freedom, ease, and autonomy is not possible when you are still operating according to the lie that working more, working harder, and being exhausted are necessary for success — never mind necessary to belong or survive. Recognizing the ways that your body has internalized this lie and allowing yourself to unlearn and reprogram this response is not as easy as reading a book or listening to a podcast. It is an ongoing practice.

If you desire freedom and ease from your business, you must know that with feelings of freedom and ease will come feelings of intense vulnerability. Working more, in this case, acts as a means for self protection. After spending a lifetime practicing hustling as a means for survival, we can only expect that it will take time for our minds and bodies to unlearn and relearn a new way of doing things. But we can only do it if we start practicing a new way of being — by tolerating the vulnerability and discomfort of ease.

Coach to entrepreneurs seeking freedom + authenticity. Host of the podcast Transcend Your Dichotomy. Newsletter + free training →