As a freelancer, what happens when the door won’t open any more?

I’ve been a tech freelancer nearly my entire career, for 30-ish years. I’ve had my own consultancy companies in four different countries, working with dozens of different clients, from startups to global companies. I’m extremely senior; I have hands-on experience with hundreds of technologies. Things I build stay working for years after I leave. In other words, I’m well worth hiring.

The life of a freelancer is hard. There are downtimes. The door closes. It can sometimes stay closed for 12 to 18 months. Other times, the door stays open and I can go from the end of one contract on a Friday to the start of a new one on the following Monday. Rarely, but wonderfully, I get to choose between clients, or I get a great daily rate for some high-powered work.

The challenge always lies in finding clients. That never changes. It is like starting all over again each time. I’ve mostly relied on tech headhunters and agencies for help. Back in the day when I lived in the States, I had a reputation amongst the local agencies in my city. That always helped me land gigs. But since then, in Europe, it hasn’t worked that way.

I’ve also had to learn to pivot - a lot. I started out as a DBA, went to C, then Java, then search, then Big Data, then enterprise development/architecture, then SRE/DevOps, then cloud architecture, then AI. I’ve ended up holding senior positions all across IT, from dev lead to CTO.

But pivoting doesn’t work when there are bigger forces at work. In 2021, I was working a well-paid job at a large company, doing architecture, senior development and team leadership on a global data-driven PaaS. It was challenging (which means it was fun) and my co-workers were great people to work with. Then Covid happened. My job was cut. The client all of a sudden decided to get rid of all contractors, globally. That was a shock. But hey, I’d done this before, or so I thought. Via agencies, I found two more well paying jobs. In both cases, there was no problem landing the job with the hiring team; I had all the expertise they needed. The problem came when they went to get budget approval. The accounting department said “no”. They too were no longer hiring contractors. So that was it.

I’ve never understood the relationship between Covid and the cutting of tech contractors. Apparently that was a global response by companies. To me these things seem linked, how I don’t know. I wish someone did.

After a rough period, the door opened again and I was working another senior position for a startup. Not a great job: pay sucked at first, but I managed to move it up gradually. The founders were always trying to get rid of me to cut costs, but they couldn’t because they relied on my expertise to keep things together. The staff called me the GOAT because I always had the answers to technical problems. Even their one customer would ask for me to be in calls with their own technical teams. But eventually the founders won and I was out.

By then AI had happened. I’m not sure if that has had anything to do with my story afterwards. I’d already pivoted into AI, using it for various projects and developing my own dark factory harness. It is a beast to master, but just the kind of challenge I love.

But the door stayed shut. This time, there was a twist. None of my recruiter and agency contacts had anything for me. Hundreds of CVs went out with no reply. So I decided to pivot, again. I figured I should be finally able to find a way to build traction, attract my own clients, create a base. After all, plenty of people do it.

The twist was that I did get responses, mostly from my Hacker News posts on the Freelancer thread, but no follow-throughs. They were all startups. Except for a single case, none of these people were serious. Negotiations were difficult. It was one thing or another: they were waiting on money, they wanted to change the scope of work again and again, they had delays, they didn’t know if they should continue, etc. They were scared to make serious decisions, scared to spend money on tech talent.

So the door remains shut. I don’t think that has anything to do with AI. What I think now is that something profound has changed in the business world. I’ve been tracking this since the 90s. Businesses used to have a goal, a purpose, and they were content to fulfil that goal, whether in building things or providing services. I think founders were also different. They were happy to have a successful company, good annual dividends, and contented employees who were paid decent wages. There used to be people who worked their entire careers in the same company; the company took care of them and they took care of the company.

What changed in the past 30 years was the goal. The goal became money. Money is fine, I want it as much as the next guy, but not when it requires the sacrifice of everything else. Just look at Boeing’s story when it stopped being an engineering company and became a finance company: people died. Apparently that was an acceptable outcome. It never used to be like that.

We now live in a world where equity firms asset-strip companies that could have continued to provide employment for people and useful products and services for their industries. We live in a world of hyperscalers, circular funding, and financial misdeeds on such a colossal scale that we can’t grasp it any more. It is the classic feeding paradigm where the small fish is eaten by the bigger fish and so on up the chain to the largest predator. (Of course no one thinks about what happens when only the largest predators are left.)

“Mom and Pop” businesses are a thing of the past. No investor will fund “one man bands”, as I was once derisively called by an investor when I pitched a great product idea that already had code behind it. They won’t fund family companies either (been there, tried that). Fortune 500 companies don’t employ independent freelancers like they used to, not because they don’t have the money or the need, but I suspect because they’re involved in some weird circular funding scam with the likes of Accenture and IBM.

I think that startups are actually the only hope for freelancers like me. They are the last chance of accessing the money that’s being kept from the rest of us trying to make our own, independent way. (Look up Professor Richard Werner for more on the real flow of money.) The financial machine is always hungry for more food, so it will still throw money at potentially viable startups. If the founders are serious enough, smart enough, they’ll use this money to hire the people with the right set of skills to make their ideas real. Highly experienced people like me are still around and we have the know-how and expertise to build solid products. We may use AI intelligently, but we aren’t vibe coders. We don’t do AI slop. We don’t do human slop either. We care about security, reliability, scalability, maintainability and performance. We care about business goals and customer needs. We know how to factor all of these concerns into our designs from the get-go, without sacrificing the velocity required by startups.

That’s why I’m still focusing on startups, despite my disappointments in them thus far. Maybe I’ve paid my karmic dues, have run through enough unserious founders and can now find some quality ones. I don’t know. I have no other answers.

So I’m sitting again in front of the closed door, racking my brains for the right combination to make it open. I hope I find it soon.