“You’re going to grow up to be a lonely old man”

Ernest Shackleton Endurance

“Growing up, my mom was worried about my antisocial tendencies. I mean she would literally say, frequently, ‘You’re going to grow up to be a lonely old man’ when she was upset with me for being bad. And that never had an impact on me! But then I saw what a lonely old man looked like. And that did have an impact. It seemed pretty horrible.”

Have you ever been friends with someone you didn’t even like? Tim was just 13 years old, and doing tech support to make spending money, when he met Allen, a 70 year old retiree with no family. Allen was alone in the world, and while he did want help with his computer, he mostly needed someone to talk to. Though more than 50 years Allen’s junior, Tim became a reluctant friend and listener in a one-way friendship that went on for more than 15 years. In many ways, Tim didn’t even like Allen – but if you spend enough time with someone, in a strange way you do come to care about them. (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…)

Ask Edna
11 years as an advice columnist

The Gossips

Wouldn’t it be nice if someone could just tell us what to do when we have important questions about our lives? Surely everyone has fantasized about this, and surely that desire is part of what drives a persistent love of advice columns. From Dear Abby to Dear Sugar, advice from strangers has been a social constant for a long time.

Today’s guest was an actual anonymous advice columnist. Andy wrote a column called “Ask Edna” for eleven years, from 1996 to 2007, where he fielded all kinds of questions (many of them about office romance, ahem). This interview has been edited for clarity.


Tell me about Ask Edna.

My advice column, “Ask Edna,” was written for Wunderman/Y&R for 11 years. The last two of those years, it went global across the agency intranet.

My identity was anonymous the entire time. I chose the pseudonym “Edna” because my name is Andy, and “Andy” spelled backwards is “Edna”….well, almost! LOL.

(read more…)

But Wait, I’m a Feminist!

Hieronymus Bosch-The Garden of Earthly Delights

Last year I got caught in an existential battle between my inner feminist and my ego.

I was giving someone I used to supervise her annual review. I had only good things to say about Victoria (not her real name): her work was excellent, on time, and thoughtful. She was young and early in her career, and I was really happy with her development and wanted her to be satisfied in her role. She’d been underpaid for some time, and I had worked hard to get a significant raise for her approved by my boss. Victoria and I had sometimes struggled to connect, and I was looking forward to giving her the good news.

After I told her that I was really happy with her work and wanted to show my appreciation with a salary increase of more than 20 percent, I waited to see Victoria smile and hear her expression of happiness. Only she didn’t seem especially glad. (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…)