About Free Soloing

(Or; Why I Started This In The First Place)

Being a solopreneur is hard. Really, really hard. I’ve known this since I started my first company in 2008, almost 15 years ago. But it didn’t fully register for me until 2018 when I got an email from one of my friends who was a coworker from many years before. He mentioned one our mutual friends, Dan.

Dan was a nice guy my age, a fellow small business owner, and a solopreneur. He was a great guy that I referred some my own clients to for IT work from time to time. I had wondered why I hadn’t heard from Dan in a while, and my friend solved the mystery for me.

“So you remember Dan? I found out that he committed suicide a couple of weeks ago. Sounds like he was so far in debt and super depressed. It’s pretty sad – he left behind a wife and 7 kids. Still can’t believe it.”

Dan was just like me: a self-employed husband and father, a small business owner, and, apparently, a guy struggling with financial difficulty and depression. Although, unlike me, he decided that he couldn’t take it anymore so he killed himself.

In Memory of Dan (1983 – 2018)

This rocked my world.

That could have been me… it may eventually be me, I thought. But then I realized how selfish I was being, just thinking of myself. Dan left behind a wife and seven kids, who now no longer have a husband and a father. How hard must his life have been? How awful that he felt that his only way out of his difficult situation was to end his life. And how sad that he felt he couldn’t reach out to people like me who would have done whatever we can to help him out, or give him support or steer him in the right direction.

I pondered this all throughout summer of 2018, and eventually decided that I would do whatever I could to try to make sure that this never happens again.

We who are self-employed lead a weird life: we go long periods of time without pay, we work on 100% commission, if our business takes a loss, it comes out of our pocket, we don’t have paid vacation or healthcare or other benefits, our spouses and friends have no idea what we do for a living, and taking vacation can be a miserable experience since we often take our work on the road with us everywhere we go.

Whenever we fill out legal paperwork, we look at the “employer” section and don’t know what to write. Every time we apply for a loan or financial account and the application says: “Please include your three most recent pay stubs,” we think “Oh, crap, now I have to explain my situation.”

Most people who have a “normal job” have no idea what this is like. They don’t know what we’re struggling with, or what we need, or how to be there to help us. They can’t relate to not having a steady income or paycheck, and they don’t understand things like how we need to wait to save up for big purchases but don’t know when that day will come since we don’t have a normal income stream. They don’t understand why things like “withholdings” are so complicated or why we do things like have to file extensions on our taxes.

Sometimes, we suffer silently, and have struggles that are so unique that most people we know can’t relate to — so WE MUST find a way to connect to each other and offer support and a listening ear. We HAVE to be there for each other, and say things like “I know how you feel,” and actually mean it.

If that resonates with you, please join me. I’m still making this up as I go, and I’m not sure exactly what Free Soloing can offer, but I know that at a minimum, it can be a place of sympathy and understanding, where we can join together with our hearts, our experience and our skills.

Please. As I’ve said many times about solopreneurs and freelancers: “We may work alone, but we are not alone.” Let’s make this a promise.

Ron Stauffer

08/01/22