Going Solo and Dark Alleys


April 15th 2022


After twenty or so years as a software developer, mostly in consulting, I felt like I could handle myself in even the most tenuous situations.

Sure, there were the miscommunications around scope or requirements. Or differences of opinion on technical solutions or philosophy. Or even just general stress around tight deadlines. But in any of these scenarios, I always felt like "I got this". I could navigate through just about anything, at least without ruffling too many feathers or dropping the ball too egregiously. Things were comfortable, more or less.

Then I went out on my own. And immediately it felt different.

Of course I expected this to some extent, but I was surprised at the degree to which I felt exposed. It was as though I had found myself in some dark alley, danger lurking around the corner and no one to rely on but myself. I was Chuck Norris in some 80s action movie. Except without the martial arts skills or unflappable confidence.

This exposure came at me in two ways.

First, there were new responsibilities on my shoulders - things that were taken care of for me in my prior life. I now had to market myself, negotiate my own rates and contracts, accept and also turn down work, and so on. And this part was a feature not a bug. I expected that I'd need to do these new things, and in fact it was part of the whole appeal of me going out on my own. I'd need to be self-reliant, but in return I could control my terms - what I worked on, when, and for how much - and to not cede control of these things to some other person or entity who was also trying to optimize their best interests. It was new and stressful to do these things on my own, but I welcomed it.

But there was another dimension that I didn't anticipate, and that was the day-to-day exposure. Right from the start, the things that I was used to doing as a normal part of my job felt a bit different. I was accustomed to being a consultant, and so my whole approach was already infused with an extra ounce of tact and agreeableness. But it was different being solo. Before, I had always had at least a few people on "my side". Other consultants coding along with me. Client partners advocating for me. Project managers backing me up. Without that team, each and every interaction felt a bit weightier. Every assignment or task a bit more crucial. I was more conscious of how I held myself when facilitating a meeting, more aware of every code commit I made, and more vigilant about being productive always.

Working for a consulting company, there was always some inertia working in my direction. My small screw-ups or lapses, it always seemed, would just be rolled over by the greater machine, lost or forgotten. There were people to back me up, or share responsibility. As an independent though, what I did and what I produced was more directly linked to me and solely me. There was no cover. I stood alone. And this did ratchet up the stress.

So if the exposure, both in big and small ways, increases after going it alone, why do it? It seems like a net loss. Here's where there's a silver lining.

As many wise people have said in one way or another, without discomfort there is no growth. And for me, this has been true. These new experiences, though stressful, have been a great source of learning. Before, as a doer, I was never "in the room where it happened", and so never learned how to confidently negotiate, market myself, or navigate tricky account situations. Now I have some level of comfort with these things. I've added some business skills to my primarily technical toolbox.

There's another layer to this, beyond just the new experience. As a consultant for someone else, I always gave up a cut of what the client was paying for me in compensation for shielding me from these "exposed" situations. I'd kick up anywhere from 30-60% to pay for the client partner to negotiate for me, and the accountant to do my invoicing, and the project manager to generally grease the skids.

Often this seemed completely fair - these things were a big help, so I could focus on my work. But eventually, as I got more experience, this cut that I surrendered to someone else to do these "businessy" things seemed incommensurately large relative to how much effort they took. If someone helped me land a new contract, it made perfect sense to kick up a large chunk of my bill rate. But then when I got extended for a 2nd year, why was I still giving away 40% of my bill rate to that person who only helped in the beginning? Basically, there was a tangible cost to being shielded from these "exposed" business situations, and now that I'm on my own, I don't need to pay that cost, and it's nice.

So in the end, there absolutely was an initial bump in stress and discomfort with the new level of exposure. And, admittedly, I did drop a few balls and maybe even burned a bridge or two as I got my feet underneath me. But I've appreciated the confidence I've gained through these experiences, knowing that I can now handle myself in a few of those dark alleys.

This is part 2 of a series. Read part 1, The Loss of Bullshit.

I'm an "old" programmer who has been blogging for almost 20 years now. In 2017, I started Highline Solutions, a consulting company that helps with software architecture and full-stack development. I have two degrees from Carnegie Mellon University, one practical (Information and Decision Systems) and one not so much (Philosophy - thesis here). Pittsburgh, PA is my home where I live with my wife and 3 energetic boys.
We're hiring! Looking for a full-stack developer (React, NodeJS or Java, AWS) open to contract work. Fully remote. The model at Highline is a little different - we're more of a co-op than a traditional consultancy. Our goal is to reward the person doing the work, and keep everything else streamlined. If you're interested, hit me up at ben@highlinesolutions.io to find out more. Send along a resume, or better yet a TechRez!
I recently released a web app called TechRez, a "better resume for tech". The idea is that instead of sending out the same-old static PDF resume that's jam packed with buzz words and spans multiple pages, you can create a TechRez, which is modern, visual, and interactive. Try it out for free!
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