I made it for a little over 6 years as a full time freelancer before I went full time (about 6 …

I would agree to this. I think there is an idea that you become your own boss. In some ways thats true but mostly so you can say that to yourself or someone else. Your destiny is still controlled by clients. If you think about most things -- very few people are their own boss, there are always stakeholders who control your time spent. It's also a lot harder to disconnect for a period of time to go on a vacation. You kind of always have to be on. I'm sure there are some people who can do that and hack that split but when you have to constantly make sure theres a pipeline of work you have to manage client inbound.

Many decades ago my dad started his own small business in insurance claims adjustment. He spent an entire year trying to get it off the ground, but the only client he was able to secure was his own former employer, and fortunately after a year they offered to just take him back on as a full-time employee again. He told me the stress of constantly searching for new clients (and trying to do sales etc.) was absolutely miserable, and the psychological security of a regular paycheck beat the slightly larger amount he was making as a contractor.

Yep, this was my exact experience. A 40 hour work week was a vacation by comparison. https://www.brightball.com/articles/what-exactly-happened-to...

As a freelance contractor you have two full time jobs. One is finding new work and the other is doing the work. As someone who likes the variety and freedom of being able to contract and define what the customer owns while still building my own startups I thought it was a good trade off when I was young and wanted the experience. I have gained a metric ton of experience and been paid to travel globally. Now I’m older and glad I put the time in. I don’t expect I’ll ever need to do so again.

When I started out I freelanced full stack web dev. I found the best thing to do was build a network (through pub meets, coworking etc) of friends and other freelancers who would funnel work to me when they were overloaded, and so there was always a constant stream of stuff to do, then once your rep and cash flow were good, start increasing your rates and diversifying the types of work you were taking on - some of the former kind, some being referred directly to clients, sometimes joining teams where people need the gas turned up for projects etc. I’m full time now but if I could save up buffer and learn more personal stability and discipline I’d maybe give it a shot again. It really is about who you know. People will happily fill your time if you can be depended on to figure stuff out and take problems off their hands for them. Also mixing less well paid reliable and prompt income with …

I would absolutely recommend freelancing to people who need to study to move up, e.g. doing Stanford online masters or MBA and can put tuition into taxes. Rarely companies reimburse full cost and as a sole proprietor one has a chance to write education off via taxes, i.e. no student debt and top-end education/network.

I contracted with a single client for 3 years. It was as close as you could get to being full-time without being full-time. Everything just had annoying overhead. I needed a CPA to do taxes because I didn't want to spend the mental cycles on it. I needed to buy, update, and manage my own systems. I needed to do my own risk management, compliance, etc, etc, etc. I needed to find my own healthcare. All of this was possible. However, it just added another layer to work that was annoying and distracting.

On the other hand I have been freelancing for the past 10 years after 15 years of working as an employee. I no longer need to burn certain amount of hours in front of the computer. My compensation is based on my results. This is probably the biggest change that happened for me -- it allowed me to think about my overall performance as something I do and optimise for myself. Another thing is that when you work as an employee you are getting bunched up with other people. This is fine if you are an average, but if you work every day to excel and improve your performance you are doing yourself disservice because you are subsidising all those other people who barely pull their weight or don't do it at all. My results are now tied to me and my image and people notice, tell other people. It has landed me many jobs or improved my negotiation position a lot. Another one is I no longer fear of loos…