I’ve let some very lucrative opportunities slip through my fingers over the years.  I won’t call them regrets as I’ll explain later, but I could have ended up with a lot more money than I have now.  Here I describe the top three potential paydays that got away from me. Bitcoin I spent my career as a cryptographer, so it’s not too surprising that I took an interest in the workings of bitcoin when it first appeared.  I learned how it worked and appreciated the clever way it was designed to mimic mining for gold without the need for a central authority.  For a while, that’s as far as my interest went. Later, some enthusiasts formed a group to work on mining bitcoins, and they wanted me to join.  I was tempted, but decided that I had other things to do with my time.  Given the way I tend to get obsessed with technical projects, if I had joined in those early days, I could have mined thousands of bitcoins. When bitcoin prices were manipulated upward to spark the...

Most people do their jobs well, but there are some who can’t or won’t do their jobs adequately. The most obvious consequence of keeping bad employees is that paying them is a waste. But there are follow on effects that are much more serious. In the private sector, these problems tend to take care of themselves, but not so in the public sector. There are many problems that come from allowing bad employees to stay in an organization: 1. They cost money but don’t produce their share of output. 2. They take up the time of other employees. 3. Some talented employees will become disgusted with having to work with incompetent employees and will leave. 4. Over time some bad employees will move up in management where they can cause more damage with poor leadership and bad hiring decisions. 5. An organization that goes too long without culling bad employees will eventually lose its ability to distinguish between weak and strong performers. Of all these problems, only the first o...

I’ve worked in high tech for a long time now and have lived through many rounds of layoffs. I’ve noticed that employees generally handle the possibility and reality of getting fired quite poorly. ( Disclaimer: No, I didn’t just get fired. In fact, my employer of several years seems quite happy with me. But that could change any time. ) Possibility of Getting Fired Employees are mostly complacent about the possibility of getting fired. That is, until a colleague gets fired or their employer announces upcoming layoffs. Then most employees are nervous wrecks until it seems like layoffs are over. Then they slowly transition back to complacency. There are people who don’t follow this pattern, but most do. Whether they are in a period of complacency or fear, few employees do much to prepare for possibly being fired. If you force yourself to confront the reality of what would happen if you lost your job, it becomes self-evident that you need emergency savings and should limit d...