Good Luck!



A home for sale in my zip code.

When I arrived at the airport a few weeks ago, the porter at the curbside check-in greeted me with a smile.  There was no line at the counter, and I smiled back.  He asked me for my name and destination, and proceeded to look up my flight.   

“Aisle seat, you’re lucky,” he said. 

“I know, especially since I wasn’t able to select a seat online when I bought the ticket.” 

“You must have checked-in early,” he said.  I told him I did. 

He then chimed in with, “You’re Pre-Check TSA too.” 

“Lucky again!” I laughed.

I’ve been thinking about luck a lot lately.  In the course of the U.S. 2016 presidential campaign, I’ve listened to all the candidates lament how the middle class has been squeezed, and how economic upper mobility in the U.S. is under pressure.  I’ve been wondering about how I would feel if I had gotten “lucky” in my career in technology.  Of course, there’s the old trope credited to various sources, “The harder I work, the luckier I get.”  That may have been true decades ago, but I don’t know anyone who doesn’t work hard any more.  Even the low-wage service worker who often has to hold down several low-paying jobs just to get by works a lot harder than most professionals I know.  And most professionals I know are exhausted more than they are energized, and nearly every one of them questions what price their work ethic is paying on their families.

As a young, single mother, I knew the only way I could become financially independent was if I had a college degree in a growing field.  When I graduated with an Associates degree, I had great job offers because of my high G.P.A.  Yes, hard work was a prerequisite to balance straight A’s with single parenting. Luck didn’t really play a role in my early career at all, yet I’ll acknowledge the head-start privilege I was granted as a pretty, white girl. Gradually though, as I accumulated skills, a network, experience, and a bit of a personal brand in my field, I started to believe I deserved the American Dream too. 

I was able to go from young welfare mom to an internationally recognized professional who owned two homes, two cars, one truck, and two businesses. I once furnished an entire house with cash.  I was also able to renovate a second home which included the addition of that surefire trophy of suburban success: a built-in heated swimming pool. I even paid for my wedding and honeymoon with cash.

Midway through my career, I left a six-figure executive position with a consulting firm to join a startup where my new partners lured me away with with a generous stock package.  It was the first time I thought I could actually “cross over” to a life of not having to worry about money at all.  If those stock options could be converted to a cash payout, I would be A-OK. 

Of course, like so many others who count their stock options ahead of time, that didn’t happen. The company went bankrupt and the options were worthless.  I think something even illegal was going on with the founding management as well, but I was long gone before that weirdness emerged. That company was the first in a string of unsuccessful moves I made to join startups where the payout would be awesome, if only… the company could exit via the public markets and I could cash out.

One of these startups involved one of the largest investment banks in the world, Morgan Stanley.  I convinced myself that if Morgan Stanley was investing in this company, it must be a sure thing.  Nope, the company folded, and I lost the investment I made in the founders’ shares I bought originally to join the executive team.  Another company was headed up by an entrepreneur known to have a large ego who had been fired from his last startup. That company was backed by one of the most prestigious local venture capitalist firms in town.  I thought to myself, “His ego won’t allow him to fail twice, so this must be a sure thing.”  Nope.  The company was dismantled and liquidated in a fire sale.

So, no luck for me.

What I’ve been wondering is how I might be a different person if I had gotten lucky?  If I had been able to cash out with a windfall of stock options that catapulted me into the 1%, would I have believed I was more deserving?  Would I have believed I was special, because I worked hard to rise above the economic circumstances into which I was born?  Would I look with disdain on people who had fewer material assets than I had?  Would I be living in the home showcased in the photo above?

Would I be (gulp) a… Republican?

So many of my career friends who had soul-sucking jobs that involved carrying bags for executive miscreants were able to cash out. Now, they live lives of comfort. I pitied them then, but are they pitying me now?

I watched a documentary again last night, “Park Avenue: Money, Power, and the American Dream.” I forgot I had already seen it, but got pulled into it again once I started watching it.  In the film they highlight research conducted by Berkeley Psychologists Paul Piff and Dacher Keltner. The team ran several studies that looked at how social class (measured primarily in terms of wealth, private education, and prestige) had an inverse relationship to caring about others – especially those who had less. The film demonstrates how even in an obviously rigged game of Monopoly, study participants adopted an air of entitlement.  Piff gave a TED talk on this topic:

The point of this long piece is, the older I get, the more grateful I am that I was not warped by the excesses of capitalism. Losing my affluence has made me more human, more empathetic, more interested in achieving sustainable gains for a greater swath of the general population.

My American Dream didn’t turn out the way I expected, or once had hoped. Yet, my dramatic personal economic rise and fall has forced me to see humanity more clearly. In the end, I’ve come to realize I am far luckier than I ever imagined I could be. Devoid of the trappings of wealth and materialism, I’m a better person, a more grounded person, and much more in tune with the human race and what being fortunate really means.

Eye on Poverty: Homelessness Revealed

With so many Americans still out of work, I’m particularly sensitive to the plight of the homeless these days. It’s alarming to recognize how quickly individuals could find themselves without proper shelter for themselves and their families. I heard a statistic on the radio that homelessness has risen to over 10,000 in the city of Austin. Austin is particularly humane about helping the homeless with various community and local programs, as well as not criminalizing panhandling (it doesn’t work: read why). There is much work to do, but as cities go, Austin is more progressive than most.


Last week, Austin was visited by Mark Horvath (@hardlynormal) who is touring the U.S. filming the homeless in various cities . Take a look at some of the video Horvath has shot on Unless you’re truly heartless, it will leave a permanent impression. Horvath is succeeding already in his mission to “put a face on the homeless.”Alan Graham (@mlfnow) was introduced to Horvath via Twitter. It’s a huge testament to how social media can be used for social good. A group of us in Austin (@mikechapman, @jonl, @heatherjstrout and @bryanperson) collaborated on a social media initiative during SXSW to raise Mobile Loaves and Fishes’ profile. In short, social media has been the gift that keeps on giving for Alan and his team.In other homelessness news, I had the privilege to watch a documentary last night by local director Layton Blaylock, “Art from the Streets.” The film was a part of a local initiative currently underway by Lights.Camera.Help. another non-profit that hosts a film festival dedicated to promoting non-profit and cause-driven organizations. The documentary covers the amazing Art from the Streets program that has been held every year in Austin for the last 17 years.There is a similar thread linking the Art from the Streets program and the work done for the homeless by Horvath, Graham and others. It’s the compassionate interest in delivering something of higher value than heightened awareness, food, clothing or temporary shelter: it’s delivering dignity to a pocket of our society that exists on the periphery of our lives. I encourage you to purchase Blaylock’s film from his web site. It would be terrific if this film were picked up by a national distributor. It exemplifies, along with Alan Graham’s good works, how Austin is a model city for its treatment and creative resourcefulness in educating us who the homeless are: they’re us without our creature comforts.

Cosmic Connections, Lessons, and Some Blessings from the Social Web

I’ve written many times about how the social web is teaching us and opening us up to a greater understanding of ourselves and the world we live in. This week, I witnessed first hand the power of relationships, the immediacy of the social web, and learned a great lesson in tolerance and understanding, and dare I say, faith? I’ve written a few times casually about how I’ve been personally affected by the downturn in the economy. As a result of my own economic crisis, I was turned down as a worthy co-signer for Amie’s student loans. Mostly I have felt awful about the prospect that I would be the one, in the end, who stood in the way of Amie’s dream of going to New York University. Of course University of Texas, Austin is an excellent school, but Amie’s heart already moved into the dorms at NYU. For good reason, she convinced me over the past few months NYU is where she belongs and where she aims to fulfill her lifelong ambition to contribute toward improving our imperfect world.


Last week, Amie graduated with honors from Westwood High School. Here she is pictured at the Erwin Center donning her IB bling. I forced her to stand with the Capitol Dome in the background to snap this photo. You can see how enthusiastic she is by her expression about the prospect of linking her graduation to Texas and UT. The reward of graduating from such a difficult school in such a competitive program was eclipsed by the heart-breaking disappointment that Amie would not be returning East to continue on her academic journey. To Amie’s credit, she accepted her fate and began to let her friends in the Northeast know she would be staying in Austin.

On Friday, last week, I was “facebooking.” A friend asked me a question on my wall regarding where Amie would be going in the fall. The difficulties we’d been having had been chronicled on my Facebook page for months, so a wide range of my friends were curious about Amie’s ultimate college decision. When I responded to my friend that we were unable to send Amie to NYU and she’d have to attend UT Austin in the fall, I received a pop-up IM from another friend who was on Facebook at that moment. That friend was Greg Grosh. He asked me why Amie couldn’t go to NYU, and I explained all the details over IM. Greg’s reply? “I’ll be happy to co-sign Amie’s student loans.” My knee-jerk response: “Are you fking kidding me???”

As it turns out Greg, who is in what he calls his “second retirement” is affiliated with The Point Foundation which “provides scholarships, mentorship, leadership training and hope for students of merit who have been marginalized due to sexual orientation, gender identity or gender expression.” Greg is helping a few kids get through school and is willing to help Amie too. This news floored me on a few levels. First of all, the cosmic connection here is Amie is more connected to gay friends and family than anyone I know. Her father is gay, in fact. I’ve always been mildly uncomfortable with the gay community that surrounds Amie.  Greg’s generous offer has forced me to take a hard look at my own repressed intolerance. Reading the literature on the Point Foundation’s web site has done me a world of good. I encountered something similar (via Facebook again) a few months ago relative to racism. Who knew I was a racist?

The SocialWeb that connects us is breaking down the ignorant walls that divide us. I’m living proof of the power of the SocialWeb to challenge our entrenched, stereotypical, ignorant biases by exposing us to new ideas and new freedoms. The second meaningful outcome relative to Amie’s new opportunity is related to generational poverty. Getting Amie to NYU is symbolic to me. Although I’m certain Amie would have done well at UT, the opportunity to attend a private university should break the cycle of generational poverty that has been shadowing my particular branch of the family tree. I was the first one to attend college in my immediate family, although I never completed my education. There have been many debates over the value of a good education. I could probably argue both sides persuasively. My most convicted arguments would fall on the side of pro formal education, however. It’s taken a lifetime of “breaking the rules” to understand this, but in this new era of social mobility and connection, I believe it now more than ever. Further, if this is the generation that is going to finally set things right, they’ll need all the ammunition they can stockpile. And the reinforcements they’ll need will come in the shape of empathy, knowledge, and compassion for those people and places that exist outside of our comfort zone.

So, congratulations Amie. You’re going to NYU. Thank you Greg for your generosity, and thank you Mark Zuckerberg for keeping us connected and integrating our public and private lives. Oh, the biggest news here is Amie finally signed up for Facebook. My rebellious day-dream believer is now a digizen.