If you have a choice never have a job.

In his talk, Ten Things I Have Learned, Milton Glaser hands down a list of axioms he earned through an amazing, life-long career in design. I recently rediscovered this document after it sat in a folder marked “save” for a few years. Instead of leaving it there, I thought I’d share these “ten things” and add my own two cents, or this case seven dollars and forty-two cents.

Milton’s second thought is a dooo-hooo-hooo-hooozy. And every time I read it (and I’ve re-read it several times already this morning) I can feel an energy climb up my spine—standing the hairs on my neck straight up. Like the energy of one hundred Liam Neesons skits. Oh baby, I can feel the force! I’m in a coffee shop right now so I have to contain myself, but I could totally flip over every table in this place if I was okay spending quality time in front of a police bodycam or two. Alright, let’s get at it, Milton writes:

02/10 — If you have a choice never have a job

One night I was sitting in my car outside Columbia University where my wife Shirley was studying anthropology. While I was waiting I was listening to the radio and heard an interviewer ask, ‘Now that you have reached 75 have you any advice for our audience about how to prepare for your old age?’ an irritated voice said ‘Why is everyone asking me about old age these days?’ I recognized the voice as John Cage. I am sure that many of you know who he was—the composer and philosopher who influenced people like Jasper Johns and Merce Cunningham as well as the music world in general. I knew him slightly and admired his contribution to our times. ‘You know, I do know how to prepare for old age’ he said. ‘Never have a job, because if you have a job someday someone will take it away from you and then you will be unprepared for your old age. For me, it has always been the same every since the age of 12. I wake up in the morning and I try to figure out how am I going to put bread on the table today? It is the same at 75, I wake up every morning and I think how am I going to put bread on the table today? I am exceedingly well prepared for my old age’ he said.

Ok, now I know where my faux rage from earlier in this post came from—the decimation of tens and tens of thousands of jobs in the last sixteen months! The companies that threw people at pandemic-induced pivots unceremoniously kicked to the curb once the masks came off due to extremely poor leadership driven by a black hole of vision, strategy, and an imperial inch of foresight.

“Never have a job, because if you have a job someone will take it away from you” gets a ‘ding-ding-ding’ from this author. Spot on. Direct hit. If I may add to John Cage’s thought, not only will they take your job away, but your dignity too. Unfortunately, I speak from experience but after years of reflecting I’m grateful for those horrible moments in my career because they have prepared me for the future. I have gained more maturity to know what I don’t want if I can avoid it, and that’s a job. Yet, I might have to—no matter how you live, eventually, money is a requirement—but I’m hoping that I won’t ever be assigned another employee identification number or a security badge.

The last sixteen months have been spent ideating, validating problems, and starting small initiatives to put things out there and see what sticks. I don’t want another job, I want to stick out the rough times and start a small quiver of tiny companies. And I hope you, my friends, don’t have to either. This is exactly why I’ve started Jump Ship! with Ryan Rumsey. We want everyone to go into business for themselves, especially our peers in the tech industry who can be, and have been, tossed aside via video chat despite any loyalty and contributions you made.

I don’t want 100% of my revenue to come from a single source whether it's from full-time employment or a single client. I want to wake up and know that I have several ways to put bread on my table. And in doing so, I can provide many types of services (maybe one-day products!) that line up with my unique expertise, and interests, and, more importantly, allow me to collaborate with friends.

Though it’s not a priority or a life goal, if I am ever going to put a dent in the universe, it’s going to be in the job market. I hope one day you can do the same.