Long-Term Thinking Is Uncomfortable

Nobody wants to admit they're short-term focused, but the vast majority of people I know are. They tell themselves a story about how their short-term thinking is actually strategic and long-term but it’s all baloney. There's a simple test that all of these excuses fail, which I'll share in this email.

I've been working with Bill*, a senior engineer, for a couple of months now. He's seeking a Staff/Principal engineer role in big tech, the roles that pay $500k-1MM or more a year. Bill is a serial job hopper, and it's been paying dividends. He got to senior engineer in what felt like record time by moving companies on average every 1-2 years, with each hop either giving him a level bump or a massive increase in compensation.

Bill is experienced, technically deep, and has a track record of leading teams of engineers on numerous projects. He's also sharp as a tack and has wonderful self-awareness and communication skills.

But he's having problems achieving the Staff+ level at his current gig,…