I never considered the idea of a career because I lived as a hippie. There was always some job that paid enough so I had food and a place to live. Modern life seemed to make a wife and kids improbable, so there was no pressure to have a complex job paying enough to support the unlikely prospect of having a family.

The long future would be fine, if you trust that the government won’t raid investment plans to fund its loyal dependents. My 401ks were maxed out when offered, and spare money went to low cost index funds. There wasn’t a lot I felt need to buy.

What would a career look like? You only get a sense by meeting someone who has cultivated excellence in some area for a few decades. Of course a company wants a highly skilled worker when doing something that matters, and has no time to waste on a failing fool making simple errors from inexperience. With trivial labor like collecting leaves or mowing a lawn, just about anyone who shows up is good enough.

Experts think things through many steps and for multiple scenarios, so when uncertainty resolves and one or several of the the possibilities appears, the expert expected it and is ready to act thoughtfully to adroitly solve complexities.

But I cared about music and ideas because life felt magical and full of potential, which was helped by being free of complex work concerns. Everyone else quickly lost their hair, got fat, and gained wrinkles, while I aged more gracefully from lack of manic stress.

As journeyman for hire, I could adequately fit into many roles, none particularly skillful and thus not highly valued. After work and on weekends I wanted to be free to live, not to study the theory and current concepts of my job, nor to put in extra hours of labor for a client or preparation in the fundamental theory of some aspects of the work I was performing when the practical seemed to be adequate and errors were well tolerated. The job would be there in the morning, so long as its technology remained relevant so that some company was willing to pay for its implementation.

However, the technology gradually changes and after a few years the old processes are replaced by newer processes, and the old approach is no longer deemed appropriate. Companies depends on common tools, and as efficiencies are realized, companies insist upon workers skilled in the new way of doing things, sometimes drastically improving outcome, sometimes just organized differently.

This puts pressure on IT workers to constantly upskill, as their toolset becomes quickly dated. You can learn some tools on the job and others must learn on your own time to stay relevant.

You don’t want to be looking for work only to realize your skillset is laughably out of date. No company has time to train people, especially when it will take a year or two to fully catch up.

You coast easy for a while; longer if you’re a hippie who has enough money and sees little obvious upside to having more. But the scary reckoning of needing to pass a job interview in a changing landscape is quietly lurking.

Every six months you should:

• Scan prospective jobs listings and see which top requirements you are lacking
• Prioritize skills you need to develop, ideally getting the employer to pay for them
• Consider where your career could go and target possible progressions and their prerequisites
• Seek job interviews for positions that would more quickly advance your career. You will probably be rejected, and you’ll see what you need to do to close the gap so you can succeed in the near future

Or enjoy the nights and weekends on your commune for as long as you can.