Great stuff Tim - I have taken the off-ramp in my career and left safe jobs to pursue dreams. I have experienced both the elation of building something successful from scratch, and the fear and emptiness of waking up with no income, no money, a failed company and a bleak future, feeling that people are laughing at me.

Things to remember: 1) it doesn't matter who is laughing at me, because who still believes in me is what matters; 2) success is an accumulation of failures, and the lessons they bring; 3) and you said it in your article: it's better to have tried than to live with the regret of not trying.

Why do we give oxygen to the defeated ex president while we have so much work to do with the new president and rebuilding a traumatized broken country? If we are successful in passing all of Biden's initiatives we will trigger a middle class revival and create millions of good jobs, for all colors and religions and across all states. This will win us millions of swing voters and will power a new economy that sustains itself far beyond stimulus spending, ushering in a new era of American middle class prosperity. Why wouldn't we want to focus 100% on this instead of looking in our rear view mirror to see if the corrupt 3rd world dictator is returning. Of course he is. We just won't let him in, because we'll be too busy rebuilding our country.

Some players swing the bat and hit home runs — they’re legends. But a team also needs fielders, pitchers — journeyman players to defend and prevent opponents scoring. And then there’s me: I swing, miss, strike out, no home run. OK, enough with the baseball analogies. I live in the exciting and confusing universe of San Francisco Bay Area and its galaxy of tech companies, VCs, founders, and all the dreamers who are currently just employees at companies, hoping to launch the next unicorn.

Me too. I’ve experienced driving a cubicle at a big dusty corporation. The mediocrity and lack…

May I have your drug dealer's phone number please.

You're right: most of us don't properly understand wokeness or the true meaning of "woke". I think in its original meaning it was for people of color to help each other stay alert, "stay woke to survive" and it was - and still is - necessary for survival in a country that still carries implicit racial bias. In its popularized form, wokeness has come to be used to describe all the people who point out racism in daily life. …

Congrats Tim! I appreciate your writing, your vulnerability and honesty, and your insights on concepts many people see as flat, 2-dimensional. I'm 59 and I've quit several jobs but also have been fired a couple of times too, so am hardened somewhat and feel less emotion around a job change. As a founder of a multimillion dollar CRM consulting company with a couple of dozen employees (when we were doing well, I felt wounded when a valued employee would hand in their resignation. I turned to the Four Agreements, and in particular #2 "it's not personal".

You're right about avoiding deathbed regrets: as Nike likes to say, "Just Do It".

Go Karen! I support you 100%. Call the manager if you're not getting the service you paid for and deserve. Call the police ANYTIME you feel threatened by anything or anyone. It doesn't matter what some snowflake wokey dokey calls you. You work hard, you pay bills, you have kids to raise and a home to protect and a job that needs your best you. I don't understand why you would give two shits what some social sciences academic wants to call you because they're annoyed by your tone. These people don't matter. They're responding from a traumatized place because of the insane stuff America has witnessed in recent years, but their coping skills are childish and precocious. You don't have time to apologize to them - keep doing what you were doing.

Silicon Valley is 90% to 95% left leaning, from the junior employees to the engineers to the executives to the founders and the venture capitalists, we have a culture of iconoclasts and rebels, we reject the status quo and we share an abhorrence of the old hierarchical order. We detest inherited power and unearned privilege, and we do not respect cronyism or political favors. With the exception of Peter thiel and one or two other right wingers, we are center-left Democrats. We have created the world's only ecosystem that shares wealth with non-founding employees, often raising them from the rat…