Your Job or Your Family

My parents retired and were spending a year abroad. My mother was having a brutal time of it since she uprooted her life of 20+ years living in a small town. She and my father had left close friends and family, so they were very lonely.


I was at a brand-name start-up for about a year (a company most of you have probably read much about). I was under the impression I was doing well: I had received good feedback, launched a large product that was more complex than the start-up's usual offerings, it received great press, and the early clients were quite happy.


I made a promise to my parents that I would visit them during their trip. I told everyone at the start-up about this, repeatedly. I would go for three weeks and work remotely. I mentioned this plan both in passing and on the company's message board at least six months ahead. Everyone seemed fine with this, with nobody raising any objections that I was aware of.


But the day I posted the flight dates, it seemed nobody listened. One of the co-founders brought me into a room and said things weren't working out and told me to shape-up or ship-out. Apparently, I needed to either quit or spend 30-days getting re-hired.


I suggested that, perhaps, the trip to see my parents would be right in the middle of that and asked him if could we take this up when I got back. I was even willing to make the trip unpaid.


"No. Not an option", was his abrupt response.


Your family or your job.


Well, fuck that.


The same co-founder proceeded to tell me, "I still consider you a friend." That was rich. Do you ask your other friends to sacrifice their family for your endeavor?

My Life is Great, and I Wanted to End it

It's the overeating: The ice cream, the cookies, and how the corner store owner knows my name from late-night binges. Ok, it's not the overeating, not really. It's what the overeating means: Career depression's dark tendrils have slithered into everything.

For example, parts of my identity that I've always held dear like my athleticism? Time for some shitty cookies, because I need a sugar high tonight.

I read tech news and had the pleasure of working with some of the biggest names you'll find in all the valley news rags. I've got partners at top-tier VC firms I count as close friends. I really don't have much to show for it, professionally, other than a few almost successes. 

You know what? When you have a strong peer group, you can't help but measure yourself against it. In a high variance, low median industry like the startup world, great people will inevitably fail. A lot. 

That probably means you. It definitely means me, at least the failing part. 

If you're reading this and wondering if you are a failure for not being in the top 100 wealthiest people in Silicon Valley, just remember that even (relatively) tiny San Francisco has 800k people, which means making the top 100 means being in the 0.0125%.


You are probably very smart, hard working, and a good person. I need to remind myself of it from time to time.