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Being a Highly Sensitive Entrepreneur (Part two)

February 01, 2019

I’ve always valued the privilege to deeply focus on whatever I’m working on, but I’ve strived to do this while still having multiple big projects and priorities going at the same time. It isn’t that I enjoy that juggling act, but I’ve never seen another choice.

My life has always involved keeping a series of nets underneath me while I tightrope walk to the next phase of growth. This basically involves maintaining two lives, in one way or another: not letting go of my past self before I know my future self can support me.

I did this when I transitioned into entrepreneurship, moving from full time to 3/4 time to 1/2 time, working several independent contractor jobs on the side, then letting go of those jobs one by one as I added more and more freelance work.

When I decided to move from freelance to business owner and hired my first employees, I did it very gradually, taking on extra projects to make enough money to pay people while I figured out how to create systems to delegate pieces of my job, one by one.

Transitioning from small business owner to partner at a software company was much the same. I took on extra consulting jobs while putting all of my &yet salary toward helping pay for my share of the company.

And now, while I’m happy with where I am, I need to find a way to re-integrate writing and teaching in my work. Plus, Adam and I bought a local alt-monthly newspaper. Plus, between the two of us, we have 5 kids. My life is more full and wonderful and complex than it has ever been.

But I can’t work the same way I did a decade ago. I have burned out the part of me who is willing to work all hours building my business and leading employees and homeschooling three children without rest or recovery.

As I’m evolving toward a calmer version of entrepreneurship that works for me as an HSP while also allowing me to perform all the roles that are central to who I am, I am grappling with the idea of focus more than I ever have.

Prioritizing my most important project

In her book Growing Gills: How to find creative focus when you’re drowning in your daily life, prolific graphic novelist Jessica Abel talks about choosing One Project to Rule Them All; letting go of all of the “idea debt” you’re hanging on to from past obsessions and commitments, and focusing on the one thing that resonates the most right now and will take you farthest in the direction you want to go.

Man, this one is hard for me. I deeply admire and respect Jessica’s wisdom after getting to collaborate with her on a creative focus workshop 3 years ago, but it has seemed impossible to integrate this practice into my life, however valuable it may be. And Jessica acknowledges the very real pain of making these choices.

One thing that helped me even consider this as doable is realizing that I have projects in different domains, and I can choose one to focus on for each of them. A domain is a specific area of your life: your job, your creative work, and your personal life are the three Jessica uses. She acknowledges that our lives are complex, and very few people can drop every project but one. But we can focus on one project in each domain we’re responsible for.

In addition to that, her concept of “processes” as separate from “projects” is extremely helpful. Processes are things you build into your regular routine that you need to do to maintain the things you value in your life. Processes don’t count toward your One Project.

Finally, she limits project commitments to something that can be completed in 6-12 weeks or sooner. This gave me so much encouragement; I mean, how amazing would it be to complete the most important project in each domain of my life every 6-12 weeks? The impact that would make on my life would be absolutely worth the pain of saying “not right now” to everything else.

Purpose as the measuring stick for every decision

Recently, I wrote about how to collaboratively create a purpose for any project (and why this is useful). We did this for Tumbleweird at the end of last year, and it was so valuable. But it was also intense. While I want to have a clear, sharp purpose for every project I’m working on, I have been avoiding doing this as I look back on what an endeavor that was.

Now that I only have One Project I’m working on in each domain of my life, it’s much easier. I don’t have to figure out the purpose of all those other things I’m doing later. I just need to do it for the one I’m working on right now.

And really, the whole process boils down to asking a few questions and trying to make one sentence out of it; no need to make it more complicated than that. The questions that are relevant for me personally are:

  • Who am I making this for?
  • What do I want to be possible because this project exists, for both them and for me?
  • How do I want this project to make them feel? How do I want it to make me feel?

From there, I simply edit my answers down into one sentence that feels both aspirational and true.

I’ve written about the benefits of doing this previously, but in the context of being highly sensitive, having something that so clearly states what you’re trying to do is enormously calming. You now have a compass pointing to your true north, as well as a measuring stick for all of your decisions. You can use it to remind yourself and others why you’re making the decisions you’re making, so you can do that from a place of quiet strength and courage without having to be something you’re not.

These are things I’m still very much working on, but even the small changes I’ve made in this direction have made such a difference. I’m continually amazed at how nuanced our systems for working can become over time, and how they need to be that nuanced in order to work for our unique selves.