Fear, Wondering, and Wandering

Running a business, especially as a solopreneur who is responsible for every aspect of the business, is really, really difficult. I won’t try to sugar-coat or deceive anyone about that. Sure, I take off more time than I ever used to working a J.O.B., but I’m the hardest boss I’ve ever had and there are times we don’t get to do what we want because a paycheck doesn’t just happen from sitting at your desk and going through the motions. I’ve never worked harder than I have in the past 5 years, nor had more fun.

I started losing my jobs back in 1998. By the time 2002 rolled around, I’d had 7 jobs in 6 different fields, ranging from cancer research technician to construction material testing. Ask me about those sometime – I used to be a jack of all trades. There was usually a celebration happening every time I hit the 90-day mark at any given position.

the event

The last time that happened, I was with a start-up and had already made the fearful leap to leave a “secure job” – lots of contracts and a lot of unique skills that made me (painfully) indisposable for more than a week of vacation. So, I’d already learned to work from home, work nights and weekends, and deal with customers for the first time in my life.

I was flat out scared to death and simultaneously excited out of my skin. There were many weeks without more than 3 or 4 hours of sleep, working on projects for 12 hours and building my own stuff for another 6.

my “own terms”

The day before waking up to do MY stuff full-time, I told myself that I’d never put myself in a position to have my mental health, self-worth, and my income be in the hands of one or two people. Never. I’ve almost broken my own promise during a few rough times, but I haven’t ever followed through with a call or e-mail to pursue something, and I’ve been asked a time or two about joining a team.

It is that drive that keeps me going when I feel like a failure. Yes, I feel like a failure more often than I publicly (or even privately) admit, but this is a new time of being authentic, right? No matter what invoices and projects are doing at any time, I need only remember that dozens or hundreds of people make up my revenues, not one person signing checks.

encouraging others

Ask anyone who really knows me and has seen my ups and downs over and over and you’ll hear that I’m an eternal optimist. When it’s bad, it’ll get better. When it’s good, even if it drops to bad, things will be better than now before too long. I get energized teaching others my lessons learned and encouraging people who need a push.

The #GenesisWP community had a tremendously encouraging Twitter event happen last week that made me do a lot of remembering, some reflecting, and now some communicating. Our good friend, Jonathan with SureFire Web Services was dreaming out loud about getting to work from home and do WordPress full-time.

By the time we were done encouraging him over 40 minutes later, 8 people had participated who continued to tag me and had some eavesdroppers along the way, too.


Are you considering a leap? A transition? What’s holding you back from transitioning or leaping? Let’s discuss – there are a lot of people in your shoes and a lot of people who have been there and are happy to help, coach, and encourage.

Come to think of it – if you’re wanting to leave your J.O.B. soon, what help, info, or encouragement from my last 6 years would you be searching for in your journey? I’m an open book.

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  1. SureFireWeb says

    Love the story, seems like more and more of us are tied to our desks but break out in some way or another! Thanks for the shout out too!

    I’m still figuring out my reigns but I think I’m so freakin’ close… this should be a great year.

    Your words are truly inspiring Jesse, thank you!

  2. Little Shiva says

    I became a solopreneur in Manhattan back in March of 1993 – on my 29th birthday, to be exact. I’d gone through 4 years of fancy-pants design school (Parsons) just before computers hit the scene, and had done a few apprenticeships with famous designers by the time I struck out on my own. For me, the adventure was about teaching myself how to use the new design tools (an ongoing process) and getting free of bosses and paychecks. I’m also the hardest boss I’ve ever had, but not having to physically go sit in someone else’s box for x hours a day has always been worth it, to me. I love working on my own terms.

    I’m in the process of making a leap and a transition by working with you, Jesse. For a long time, I was able to handle everything my clients needed myself, except printing. There was also a long stretch where I didn’t have that many print projects, but the DIY web wasn’t as omnipresent as it is today, so my niche was helping other solopreneurs and small biz owners have an online presence. That niche has gotten even smaller now that solopreneurs and really small businesses can be visible online through social media – the ground is constantly shifting.

    My golden rule is to always work with the best tools and the best people. So when I was recently hired to build the biggest website I’ve ever built and I ran into some technical issues that were over my head, I searched for an excellent helper – and found Jesse. The thing that stood out in his presentation was how he liked to cultivate good relationships, for the long haul. I couldn’t agree more: it’s those connections and the confidence they build that are the stepping-stones to success and prosperity, I think.