Being a highly sensitive entrepreneur, Part one: Healthy root systems

You know how you hear about a book so many times that you feel like you’ve read it, but you actually haven’t? That’s the case for me with The Highly Sensitive Person by Elaine Aron. I finally finished it, and while I’d somehow picked up most of what was in it already, it’s gotten me thinking about the different ways I handle being both an entrepreneur and highly sensitive.

Most people assume “highly sensitive” means you get your feelings hurt easily. And while that can be one way it shows up, it’s actually a collection of traits about 20% of the population people are born with:

  • Deep processor: Thinks about everything deeply; looks beyond the surface to what’s going on underneath

  • Susceptible to being overstimulated: Hits their capacity for emotional/physical/mental/social stimulation much earlier than others

  • Emotionally reactive/empathetic: Feels things very deeply, both personally and in perceiving the feelings and needs of others

  • Senses subtleties: Picks up on every nuanced thing going on around them and inside of them

I’m a big fan of personality frameworks like Myers Briggs (INFP!) and the Enneagram (Type 4 with a 5 wing maybe?), but those are often up to interpretation…I can see different sides of myself in multiple “types”.

Being highly sensitive is different. Reading this book was like seeing all the things that are going on inside me all the time laid out, piece by piece. While Aron does have a questionnaire in the beginning of the book to help determine if it applies to you, I’m pretty sure if you have this trait, you know it.

The only job I’m cut out for

I didn’t start working for myself because of my sensitivity; I started working for myself because after becoming pregnant with my first child, I needed more money and more time. I only realized later that there was a clear link between my ability to perform at a high level and my ability to create a working environment that was flexible and autonomous.

Even though entrepreneurship is high-stress in some ways, requiring risks and responsibilities far beyond the norm, those things were easy for me compared to trying to manage my mental, emotional, physical, and social energy working 8 to 5 in an office.

It’s still been challenging, though, especially as the Internet has grown from a place where I felt safe sharing ideas and projects with my fellow nerds and weirdos to a place where everybody and their literal mom is trying to get their needs met.

Pursuing calm entrepreneurship

One of my Internet heroes, Amber Case, introduced me to the concept of calm technology many years ago—technology that “rather than panicking us, would help us focus on the things that were really important to us” (as described by PARC researcher Mark Weiser back in 1995).

For the past several years, I’ve been pursuing that ideal, but on a personal level. Knowing that overstimulation is the biggest challenge to my being able to happily and consistently perform at my best, I now understand why that idea has appealed to me, and I can see several elements that have been (and will be) essential in aligning my work life in that direction.

1. Focusing on healthy root systems rather than on what’s above ground

Isn’t it interesting how when you give a plant good nourishment at the roots, the rest takes care of itself? I’m learning that work-related growth is the same way. It’s taken me a while to truly embrace this concept (and I’m still uncovering new layers of how to do this), but the more I do, the calmer, clearer, and more effective my work becomes.

At an individual level, this means optimizing my habits and rhythms rather than chasing bigger and better projects and outcomes. This has been tremendously hard for me (hello, INFP!) because I hate doing the same thing I did yesterday and the day before and the day before that. I love obsessing over new things and letting my passion for something drive me into the ground.

But you know what I love more? Being healthy. Being confident in my ability to keep working on something and making it better over time. Having a feeling of spaciousness in my life instead of the constant feeling that I should be doing more.

These are beneficial for anyone, but especially if you have HSP traits. It is incredibly overstimulating to live in a state of reactivity and pressure to perform, and that takes time to recover from. And ironically, most highly sensitive people perform the very worst when the pressure is the highest. (Which is why one of my deepest values is freedom!)

I’m also working on applying this principle on a team level. At &yet, as extremely anti-bureaucratic people, we’ve historically operated within loose guidelines rather than within systems of repeatable processes. As we’ve matured however, we’ve realized the value of those things.

Over the past 3-4 months, I’ve been facilitating the creation of an annual plan with our stewards team (what we call our partners). But instead of throwing goals at people, we’re taking the time to think through the habits and systems that will support us in executing our plan week by week, month by month, and quarter by quarter. We’re also building feedback loops to make those habits and systems better as we go.

I can’t speak for everyone, but this has lowered my anxiety significantly and made me much less reactive to the ebbs and flows of client/consulting work. I now feel free to continue focusing on where we want to go rather than getting stuck in the weeds of every problem that crops up. And whether highly sensitive or not, that’s where all of us need to be if we want to experience healthy, sustainable growth as business owners.

In his book Atomic Habits (which seems to be in the water lately…I’d definitely recommend it if you’re thinking in this direction), James Clear talks about how projects are moving goalposts that rarely bring the promised satisfaction at their completion. In contrast, habits and systems change who we are and what we’re capable of as people. Not that we shouldn’t have projects and goals, but that we have greater impact when we focus on the habits and systems that support them, rather than the outcomes themselves. I’ve read a lot about habits, but that one concept completely changed how I view them and prioritize them into my life.

Which leads me to my next point (which I’ll save for another day…this post is turning itself into a book!): maintaining a sharp purpose and priorities. I’ve already written a little about purpose, but I want to talk about it from the perspective of being highly sensitive.

(Also? Can I just say it feels so good to be writing again? Habits and systems ftw!)