Being a highly sensitive entrepreneur, Part three: Removing obstacles rather than trying harder

When I was in the eighth grade, one of my teachers (who was also a self-proclaimed prophet) told me that the lesson I would need to learn in my life was “Do not strive.” This is a wild and confusing thing to say to a 12 year old, which is probably why I’ve never been able to forget it.

Adam and I joke that we are rocket ships, constantly learning and growing and changing at a rapid pace. Striving is part of our nature. But I’m also realizing that so much of that is born from a place of “not enough” ness. As I’ve gotten more grounded and accepting of who I am, the striving part of me is dying.

I know it’s ultimately a good thing, but it’s also scary. If I’m no longer striving and am increasingly content, will I slip into complacency? Will I ever accomplish the kinds of things I once accomplished because I was running away from the mediocre person I was afraid I was, trying so hard each day to be better?

I once consulted a coach who taught me the Tibetan philosophy of “basic goodness”. This is pretty much the opposite of the puritanical philosophy of “original sin” that most of western culture is rooted in. Instead of being born evil and in need of redemption, “basic goodness” says we are inherently good and are trying to get our needs met in ways that are both healthy and unhealthy for ourselves and others.

It’s interesting that so much of our work culture assumes we are naturally lazy and work-avoidant. We need more willpower! We need more accountability! We need more striving!

While it’s true that I naturally want to do what I want to do, rather than what I’m supposed to do, I’ve also learned that I naturally want to work hard and contribute in a meaningful way when my needs are met. And getting my needs met is more about removing obstacles to being the person I already am than trying harder and harder to become a better version of myself.

The interesting thing is, noticing “obstacles” requires paying attention to the negative, which is something highly sensitive people are naturally bent toward (and often criticized for).

At &yet, we use the phrase “trust your frust” (conceptualized by Adam and coined by my teammate Luke Karrys) to describe this exact thing: noticing what you’re frustrated about and letting that lead you to your next insight. My teammate Amy Lynn Taylor even designed a t-shirt with that phrase on it to give to everyone at our remote holiday party this year.

Obviously, this can be unhealthy if what we are frustrated at is ourselves. But if we embrace the philosophy that just like a plant, we will grow and flourish in the right conditions, we know that the things going on inside ourselves are all symptoms of bigger issues that we can address.

We are fundamentally good, and good for people. So when we’re not doing the things we aspire to do, we can respond compassionately with curiosity. “What is going on around and inside me that makes this hard?“ “What need of mine is not getting met here?” “How can I get my needs met in this situation?” “How can I remove the obstacles, one at a time?”

I’m so grateful for my sensitivity to things that are hard, because I can trace every bit of growth in my life back to this habit of obstacle-removal. And as I’ve learned to accept and value that part of myself, the cycle of noticing and removing those obstacles has become easier.

If “obstacle removal” sounds like a heavy and difficult task, understand that most of the time, the obstacles in our paths are subtle and nuanced. I don’t drink my water because my water bottle is empty and I’m focused on something else. I don’t get up early because it’s cold outside of my covers and I would do anything to stay warm at 6am in the winter.

Those are all small obstacles that can be removed pretty easily (fill up my water bottle when I go to the bathroom; put tomorrow’s clothes beside my bed the night before). But sometimes the obstacles are stacked on top of each other, and it’s like untangling a fine chain necklace to get through them all. But they’re still pretty small, when you look at them individually.

For example, for the past several weeks, I’ve experienced tremendous resistance while creating a spreadsheet that contains the strategic map for our organization. I realized that while the concept is good, there is a fundamental flaw in it that my brain is still trying to figure out. That flaw is a many-layered thing that includes the limitations of the tool I’m using, my lack of clarity on some of the roles involved, my aspiration that this be something everyone can use and understand and not be overwhelmed by (and how far it is from that goal at the moment).

To remove complex obstacles like this, I need to be aware of those layers and just start working out the tangles a little at a time, knowing that it will continue to be a tangled mess until suddenly, it isn’t.

Being able to visualize obstacles as something external to ourselves (versus something wrong with us) is absolutely critical to removing them. The most creative and ambitious people I know have met more obstacles than most because they are constantly putting themselves and their ideas out there. Unfortunately, the most sensitive of those people have usually internalized those obstacles as personal failures, which makes it tremendously hard to keep taking those risks without great personal cost.

When that is the case (and it’s certainly been the case with me), putting those obstacles back outside of you where they belong is a process. But it’s a worthwhile one if we want to keep doing our work year after year after year, regardless of our failure to reach our own aspirations for it, or for ourselves.