On Money: What’$ It Worth?


When I was growing up, my family had a tradition of challenging the kids generation to not smoke until they turned 21. If the kid won, she would receive $1,000, and if she lost, she’d receive nothing. When my older cousin turned 21 and collected, she described all of the things she bought to me: a new bed, a weekend trip, a ring, maybe something else too. I would have been eleven at the time, and I marveled at how much fit into a thousand dollars.

I remember describing the family bet to a high school classmate. She was a big pothead and I had assumed that she would tell me that it wasn’t worth it. Better to have fun now. She surprised me by saying, “$1,000?! I would totally not smoke in order to collect a thousand dollars. That’s a good deal.” Apparently this didn’t have much impact on me. At nineteen, I abandoned my cash payout for a joint in Amsterdam after diligently not smoking through all of high school. (read more…)

The Rent Is Too Damn High


The dream doesn’t always start the same way, but the fundamental story is constant: I unexpectedly discover that the tiny San Francisco apartment I share with my husband and our cat contains previously undiscovered rooms. It could be that I find them through a hidden door, a closet I’d never bothered to open, or a separate entrance I’d never used. Whatever the path, all of a sudden my living space doubles or triples in size, and I don’t have to move or pay more in rent. I’m so relieved, I think. This is great.

I’ve had this dream probably a dozen times. The fact that it is recurring and so literal makes me laugh, but warily. I really do want more space, but I can’t bring myself to make the sacrifices it would take to get it — either putting more of my income toward rent than I feel comfortable with, or leaving San Francisco. At least not yet. This is the huge, looming question facing many of my friends and people in my peer group who live in expensive cities: what are we going to do when we finally decide that the rent is too damn high? (read more…)

An Angel Investor, Part 2

Egyptian jugglersI wrote “An Angel Investor” as a standalone piece without intending to explore the story from other sides. It provoked a lot of interesting discussion in the comments, on Facebook, and in private conversations.

Many people I spoke to expressed an interest in hearing about the experience from the perspective of the parent – in this case, Tim’s dad, Philip. This interview shares Philip’s side of the story of their family’s relationship with Paul. If you haven’t already, please read Part One first.

Some additional background for the reader is that Philip has three other sons and one step-son; Paul contributed to all of their college fees.

This interview has been edited and condensed.


Tell me about your relationship with Paul. How did you meet?

Paul ran a big corporation that came to our small town. My wife had recently died, and a well-connected friend of mine – who knew Paul – was worried about me and my family, because I was a single dad to four kids. She arranged to throw Paul a birthday party where one of my sons performed a juggling act. Paul and my son met that night and made a connection – and that, eventually, is how I met him.

Were you aware of Paul’s “sponsorship” of kids prior to meeting him?

No, I wasn’t. But his interest in supporting and helping my sons happened very quickly. Within six months of Paul’s birthday party, he told me he wanted to give my son, the juggler, a car for his birthday. I said “thanks, but no thanks.” But he was not one to take no for an answer and pressed me, so I said, “it’s not fair to his older brother, my other son.” So Paul said, “well that’s not a problem. I’ll give him a car too.”

That’s how our complicated relationship began. (read more…)

An Angel Investor

A Pair of Shoes

A while back, I emailed my husband Tim an article about the Sony email hack. It was about the child of a Sony executive who – the email exchange suggested – was given favorable status as an applicant to Brown University due to her influential, wealthy family. I was outraged.

Tim’s response came in the form of a Gchat: re: the gawker article about rich ivy leaguers… that may be an interesting small answers…since that happened for me

What followed was an intense, occasionally contentious, and ultimately not-fully-resolved discussion between us about privilege, guilt, and personal responsibility. This interview has been edited and condensed, and “Paul” is a pseudonym.

(read more…)

No Longer the Smartest Kid in the Room


The most blissful moment of my life was near the end of my freshman year, when my high school gave out awards for academic excellence. I won honors in three subjects—I was most proud of the English honors—and then took the cake overall: I had the highest GPA in my grade. Walking down from the bleachers, being watched by everyone, wearing a pretty dress picked out for the occasion—it was a perfect experience. Before I accepted the medal and shook hands with the principal, I thought, “This is the best I’ve ever felt.”

I felt completely validated by the external measure of accomplishment. Being best in my class bolstered my sense of self-worth. That was the pinnacle; sophomore year I had the second highest GPA, junior year, the third highest. I left high school early to go to Reed College, but once there, found I had no coping mechanisms for not being the smartest kid in the room. My classes were interesting, but I was overwhelmed and unable to cope with the amount of reading assigned. I had a nervous breakdown. I left Reed. I dabbled in community college for a bit, but after a year I dropped out altogether. Of course, too much homework wasn’t the root of my problems; the real issue was clinical depression (for which I am thankfully now medicated and therapized). Without academic success I didn’t feel anchored. (read more…)