Why Solopreneurship Sucks, and What to Do About it

When I worked in Silicon Valley, I started my days around 6 AM, got to work around 8:30, and worked more or less eight hours a day. I got a shit-ton of work done, mainly because:
‣ Others were depending on me
‣ My paycheck depended on my performance
‣ I felt part of something larger than myself.

Even though the work itself didn’t matter very much to any of us, it contributed to the company itself, and to the team of people we worked with daily. It also ensured we got a paycheck to meet our and our families’ basic needs. It mattered — on many levels.

What truly matters, no one cares about

Jump-cut to the few of us who took the leap to solopreneurship. We started doing something that truly matters to us. We believe we’re adding value to others, and to the world.

And yet, we’re alone at our desks, for hours on end. What we do manage to get done in a day has no one to witness. Maybe we have an accountability buddy, or an expensive coach to cheer us on. But no one sees our daily accomplishments — the paragraph we struggled all day to write, the five potential clients we talked to, the long walk we took to get inspired.

No one knows, and no one cares.

This is why many solopreneurs feel lonely, even depressed. Isolation sucks!

So…what if we could have that same accountability structure and sense of belonging to something larger for our passion work that we get in a corporate setting? And what if it looked something like this?:

When I worked as a book coach in the early 2000s, guess what my clients loved most about working with me? It wasn’t my knowledge of the publishing industry. It wasn’t my inside scoop on how to get an agent who could sell your book for top dollar. It wasn’t even my wordsmithing and editorial prowess.

It was when they called to tell when when they were beginning and ending a work session.

This was their work mattering to someone — to me. In our little community of two.

Because its how I roll, I became invested in each of my clients. I said to them, Now I am invested in you and your book. I care that you get this out into the world! So when you make a commitment to do this work, you’re not only committing to yourself, you’re also committing to me.

Boom! Mattering.

A structure of mattering

Last year, I did a test-run of a model where a small group of us checked in with each other virtually (online) throughout the day. We had shared our life purpose, and the kind of feedback we like to get. We named our likely distractions, and what we would to vanquish them.

Here’s a snapshot of how we communicated with each other in a given day:

Now I’m expanding that model to include some of the counseling and personal growth tools I’ve been developing for the last 30 years.

I have seen that when we take an interest in each other, communicate that interest, and get help to work with what comes up along the way, we create a beautiful structure of mattering. We have something, and some others, to bolster us along our path of doing our passion work. It looks something like this:

As a solopreneur, I myself have been lonely and needed this. I see and feel the difference in how I work when I have this kind of support. This is why I am so passionate about bringing this structure to others! I have seen how much better it feels, and how much greater is our quality of work when we share it with others, get support and feedback along the way, and help with what comes up for us in pursuing our passion work.

Have you found structures like this that work for you to repair solopreneur isolation? What’s important to include or not include?

Over here in my corner of the world, I’ve put a collection of insights and useful practices together into a small group solopreneur coaching model called NextLeveling 2019. You can learn more about it here, and even start with the first lesson. I would love to know your thoughts.