In addition to the legal considerations, note that if your employer goes through layoffs, your investment is likely to tank right at the moment you need it most.<p>You&#x27;re already have natural long exposure to your employer&#x27;s performance.  Be aware that investing in your employer is a doubling-down on their performance.<p>You also likely have some emotional investment in your career, which likely biases your judgement.<p>On the other hand, you may have industry insight that the market simply doesn&#x27;t have.  While working for Google, shortly after Google announced Android, I wasn&#x27;t sure if HTC, Apple, or some third manufacturer was going to become dominant in the smartphone market, but I was sure Intel was going to be playing catch-up in the mobile space for at least 5 years and smartphones were going to eat the world.  I also knew the huge amounts of money per year that my employer was spending on datacenter electricity and saw that for many server workloads, watts&#x2F;SPECINT and watts&#x2F;flop aren&#x27;t terribly important.  The CPU largely (oversimplification) configures DMA between the disk controller and the network card, and there was a window of opportunity for ARM to get significant market share in the server space.  This was before HP or Dell announced any of their ARM server projects or I had heard of Calxeda.  The server thing didn&#x27;t work out for ARM, but my investment in ARM Holdings still went up over 8x over 5 years or so.  I no longer think I have any more insight than the market into ARM Holdings&#x27;s share price, but I was able to profit from insight I had at the time that the average trader did not.