Yeah, I’m in IT, although half the time it feels like I’m not doing IT at all. More like management consulting for companies that have shortcomings in tech leadership? I want to be doing IT, but more often than not, they’re just blaming the tech to save face because it’s less confrontational than making people take responsibility (including themselves). So they hire a tech expert, who is doomed to fail because the problem is human in nature. I want to make money though, so I just do whatever I think will solve their problem, even if it means taking on a leadership role as a contractor. I often end up as a sort of discount, part-time, drop-in CTO with no stock options or title. There are worse things to do for a living, although frankly it makes no sense at all with the compensation and incentives that the actual CTOs typically receive. Sometimes I’ve made good money doing this though.

International contracts? Well, my experience is that they are basically unenforceable, because I can’t afford to sue someone in another country (e.g. the USA). The cost is just so much higher than the contract amount, and it would cripple my ability to do work for years by taking up all my mental effort. So I make sure to charge an aggressive enough deposit that if they default, I’m not in a mess. I’ve had billion dollar companies screw me out of 300$ (a lot of money for me at the time, haha) for no reason except that they could.

Before I learned that, foreign companies defaulted on their payments regularly. Actually, they still do, but I charge much bigger deposits to the point where it’s still worth it for me. The harsh truth is that Americans (not to pick on them specifically, they’re just the most common employer – it’s exactly the same with Chinese companies) don’t come to my country to do things well, they come here to do things cheaply – and not paying me is cheaper than paying me. I’ve tried all combinations of delivering before or after payment is received – the only thing that solved anything was hefty deposits. This guaranteed I could deliver work to my standards – anything less and I’m crippling my ability to win future work my delivering less than I’m able to.

A lot of my conversations end with “I can begin work once the deposit is received”. I grant people about an hour or two of my time in free consulting / meetings before that point (“qualifying the lead”). This was hard for me to learn because I fundamentally want to help people with whatever problem they are having – but I found that with anything more than this, nearly 100% of my time was spent in meetings or doing unpaid consulting for people that had no intention of ever hiring me – what they really wanted was for me to write a full proposal for their project so they can hand it off to someone else less experienced, or internal staff. It’s a shitty thing to do, but sadly very common.

Let’s see, what else… Learn accounting – GnuCash is glorious, screw Intuit. Convert monthly expenses to yearly if you can – time is money and juggling invoices every month costs a lot of time. Also you can negotiate better rates for e.g. office rent if you pay a year in advance. Shop around for an accountant / lawyer and so on at the start, because when you’re busy, you don’t need the hassle of switching providers. Usually other freelancers in your area can recommend someone. At the start, pay them for some templated contracts set up with he terms you like, then just change the scope/timeline/budget/invoicing sections as needed but leave the rest the same.

I usually expect to spend 1/3 of my time chasing new business, 1/3 of my time doing administrivia, and 1/3 of my time “actually working”. The hardest part is always chasing new business – coding is the easy part. I bill accordingly, because all those hours need to be paid for.

I keep a reliable outsourcing partner handy and also a network of other freelancers. For those times I don’t know how to do something, I subcontract them in, manage the client, and charge a fee. The fee is not small, because again, finding clients is the hard part. Incidentally, the way to get things done cheaply is to reach out to freelancers directly with a well-defined scope, timeline, and budget – you’re saving them that 1/3 of their time doing business development, this is what you pocket when subcontracting to them (and overall will thank you for it – they get to focus more on the fun work while you manage client expectations).

Also, try to line up some regular clients as a side hustle before switching to full freelancer mode. Even if this is at a lower rate than you want to make. Not needing to scramble against starvation, especially at the start when you’re probably going to suck at winning contracts, means you have some freedom to choose who you can work with, which is super important. Bad clients will wreck you, one way or another. I was wise enough to do this a little, but did not do this enough, and it nearly sunk me. The first 3 years were acutely distressing, I had to feed the business before feeding myself. Many horror stories from that era of my life.

Finally, my most limiting resource is something I refer to as “the space in my head”, the number of ideas I can hold concurrently – methods on how to do some specific thing without needing to look it up, the details of some client’s specific problem, how to use a piece of client internal software, etc. If someone is not paying me, I strictly allocate them none of this. I write it down and never think about it again unless I’m paid. It’s analogous to RAM. Another way to put is is that the most valuable thing you have is focus. So you need to be very strict about ordering priorities. This was hard for me, because I might be tempted to work on interesting new projects instead of things that people have already paid me to do.

Writing about these things online is an experiment for me. It helps me organize and synthesize what I’ve learned. Also at some point I realized I was dropping below some acceptable threshold of human contact outside of work. I’m some sort of mercenary science hermit :P

Hope this helps! Good luck!