2016: a Retrospective and a Different Perspective

Though there were things that happened to those that I loved that would test any person’s resolve and faith in humanity, 2016 was still filled with extraordinary experiences. While there was sadness and heartache, there was also happiness and joy. In other words, it was just like many of the years before it; and I suspect, will be like many of the years that are yet to come after it…


First and foremost, the last two years have really been about several very specific, very intentional things and experiences. More than anything else, and admittedly a work in progress, I wanted to make sure I committed to the relationships in my life, both my family and my friends, as many of them as I could. With all of us getting older, some married, some married with children, some married with children who had children, and less of my circle near and far single, I realized I would need to be the one who would need to be flexible. And so that’s what I did. I inserted myself into the lives of those I loved when they either needed me, wanted me, or simply was able to fit me in. With virtually no expectations other than when I was with each and every one of them, I would be present. And that to me, was the present I kept giving to myself. Out of all the relationships I had, the one leading into the first half of last year proved the most significant in so many ways. I loved her dearly, and while it didn’t last, I have nothing but love for her still.

Even more than the adults in my life, it’s their kids that brought so much joy into my life, as well as their own. I sometimes wonder why we forget so many childhood life lessons even while learning them on our way to adulthood. I learn more from children’s perspectives than from any other single group. The only other group on par are dogs. While their outlook is simple and straightforward, it’s their ability to let love in that shines most. They live with no filters. They let themselves be loved, and they love wholeheartedly. I love everything about my nephews and my nieces, including those of my brother and sister, as well as my cousins. I love everything about my friends’ kids. Hearing them say versions of my name and my last name and my nicknames brings light to my life.

Through it all, more than anything, spending the year with family and friends was what mattered the most. Those relationships that were the closest tended to sometimes be the most difficult but also simultaneously the most rewarding. We had another family wedding; and nephews and nieces were getting a year older. The rest of us were too, but I chose to ignore the daily passage of time with everyone older than ten.


Until August when I started working again (more on that later) and aside from my trip to India (again, more on that later), my constant companion and source of love and entertainment was my American Bulldog Taylor. Turning ten in September, thank goodness, he had still not slowed down. Whether it was with me or with his dog walker, Taylor went on weekly hikes, and some weeks, daily. Most of our hikes were along the trails in the Marin Headlands, anywhere from a couple miles to as much as six. He would hike with me, or if he was with his dog walker, with other dogs. He loved his vacations to the dog park playing (rough) with other dogs, while cozying up to every human. Every day when I woke up and every day before I went to sleep, I would thank God for his health. Shedding almost twenty pounds from his Chicago days certainly helped his joints, though he now noticeably suffers from arthritis, an inspiration to me, cos he doesn’t let it keep him from doing the things he wants to do. Knowing that his brother passed away two years ago, every day with him is simply a gift.


Many of my experiences borne by strengthening the bonds I have with those that I love predicated that I travel. And so I did — I traveled a ton, much to Taylor’s chagrin when I didn’t bring him along. My travels took me all over California, Vancouver, Denver and Steamboat Springs, Atlanta, Washington DC, Philadelphia, Tampa, and of course Chicago.

The single biggest travel experience of my life included the thirty days in March and April that I spent in India with two of my best friends — Derek and the most interesting man in the world, the one & only DaveRisner, who had never been. We visited more than eleven cities including Kolkata, Varanasi, Bombay, Udaipur, Jaisalmer, Jodhpur, Pushkar, Jaipur, Agra, Darjeeling, and Shillong. The first half starting in Kolkata and ending in Jaisalmer was spent flying between cities, experiencing things that we had never experienced before. Starting with a camel safari outside Jaisalmer, the second half was spent in the Rickshaw Run, an epic race where we rented a tuk tuk and drove it over 2500 miles from the western-most part of India to the eastern-most part ending in Shillong, before flying back to Kolkata for our return to the States.

On a trip that was both dangerous and exhilarating, we met a great many friends, some of whom we still keep in contact with. DaveRisner even gave a seminar on the leadership principles learned during the run in front of a group of several hundred executives. The three of us saw more of India on this trip (along with Derek and I in 2014) than almost anyone we knew or I imagine would know. I am still writing about this trip, cos this trip was worth writing about, and a prelude into Derek’s epic 2017 traveling the world.


I had taken a year off from work, taking a sabbatical to focus all the things that were important to me — me, Taylor, my family and my friends. I knew with every fiber of my being that my next job would have to be something that I would be passionate about. The gift I gave myself during my sabbatical (among the many) was that everything that I did during that time, I did because I wanted to. When you really sit down (or stand, if that’s your preference) to think about it, that’s powerful. Personally speaking, that’s what I wanted professionally, as unrealistic as it may have sounded.

Since 2003, every company and almost every job I held, I loved. That’s the biggest thing I’d learned professionally — to love what you’re doing; and if you didn’t love it, find a company, a place and a job that you did love. I worked for Careerbuilder for over nine years in Chicago before moving to the Bay Area to work for Glassdoor then Glint. Along the way, I met some incredible people. One of them became instrumental in helping me find my current company and my current role at Upwork, based in the Bay Area, with offices in Mountain View, San Francisco, and in Chicago.

What I found ironic was that during my travels, much of my discussions with friends and strangers involved work, and that work should look different than it did now. The truth was that by joining Upwork, I was addressing many of the things my friends, strangers and I had discussed the previous year. The future of work was indeed changing.

On a grander scale, Upwork is a platform that connects highly skilled freelancers with projects (i.e. work) that companies need to get done. The “gig economy” is a very really thing, affecting many different industries, exemplified by companies like Uber & Lyft with transportation, Airbnb with hospitality, and Upwork with employment. If you have work that needs to get done, especially knowledge-based work where location is not an issue, but are not able to budget for full-time employees or simply cannot find or hire FTE’s to complete the project, then Upwork has a solution that works.

On an even grander scale, Upwork provides people all over the world with the means to work, provide for themselves and their families. My parents came to the USA in search of the American dream. With Upwork, that dream is no longer just an American one.

On a smaller scale, Upwork provides me with the opportunity to work with really smart and really passionate people. I get to showcase my leadership philosophies with a whole new group of people, happy knowing that I have affected so many lives before me in a positive way, and excited that I am about to do the same for a whole new group.


An iconic team for the ages, after 108 years of futility, some coming thisclose, the Chicago Cubs finally won the World Series, their first time since 1945 even being in one. I happened to be in Chicago for the Game 7 win in Cleveland, and the subsequent parade downtown was right outside my offices, forming the sixth largest congregation of people in human history. Seeing Pearl Jam at Wrigley Field with Derek in August was a prelude to what I would feel in October.

I remember 1984 like it was yesterday, losing three games in a row after winning the first two. Needing only one win to get to the World Series for a rematch of the 1945 series against the Detroit Tigers, they couldn’t do it. Steve Garvey and the Padres had other ideas.

I remember 1989 like it was yesterday, pitting Mark Grace and the Cubs against Will Clark and the San Francisco Giants. An epic series by Amazin’ Grace wasn’t enough, only outdone by Will the Thrill. The Cubs lost again.

Much like 1984, 2003 broke everyone’s hearts. That was the year I fell in love with the Cubs, ten years after moving to Chicago. Five outs away from going to the World Series proved to be five outs the Cubs could not get in Game 6. Game 7 was a foregone conclusion even with Kerry Wood hitting a home run. It was an epic collapse.

Sandwiched around the heartbreak of 2003 was 1998, 2007 and 2008. The wild-card Cubs led by Sammy Sosa (who along with Mark McGwire “saved” baseball that year) was swept in the first round of 1998 playoffs. Winning the division in 2007 and 2008, with the latter having the best record in the National League, proved fruitless getting swept both years against the Arizona Diamondbacks and the Los Angeles Dodgers.

The young Cubbies from 2015 gave hope to the future, beating the two best teams in the National League (the Pittsburgh Pirates and St. Louis Cardinals) in the first two rounds of the playoffs, before getting crushed by the New York Mets.

And then came 2016.


Continuing my adventures from the previous year, I immersed myself in California. I took advantage of as many sunrises and sunsets as I could, whether it was from my balcony or anywhere else in or out of the city. I hiked all over the Bay Area as much as my aching body would allow me, which surprisingly was a lot. I even became members at two vineyards — Silverado in Napa and Ram’s Gate in Sonoma, the latter only a 35 minute drive from where I live. Something I never really took advantage of in Chicago, I decided the moment I arrived in California that I would be a tourist. And so roadtrips were the norm, cos I wanted to experience as much of California that I could. Much of that would include the drive between San Francisco and Los Angeles along the Pacific Coast Highway, the most beautiful stretch of road that I’d ever been on (with due respect to the Road to Hana in Hawaii, which I will someday drive). That stretch included extended visits to the Central Coast to San Luis Obispo and Morro Bay, the elephant seals at San Simeon, The Bixby Bridge, Big Sur, not to mention even north of San Francisco at Point Reyes. California’s beauty was something I decided that I would never take for granted. So I haven’t.


I’m not sure if it really was the case, but 2016 seemed to have an inordinate number of celebrity figures pass away, some of them too soon. We lost a boxer and a golfer, iconic musicians, a prince and a princess, her mother, and a hero for the ages from a beloved series of books & movies… from Muhammed Ali to Arnold Palmer to David Bowie to George Michael to Prince to Carrie Fisher to Debbie Reynolds to Alan Rickman, and many others.

Closer to home, family and friends of mine experienced loss, as did I. My best friend’s dog passed away to start the year. A few months later, we had Tucker painted onto our tuk tuk (along with Taylor and DaveRisner’s cat Bella, who sadly also passed away later in the year), keeping watch over us from above as we traversed the Indian countryside. The day after the last day of the race, I learned that a friend of mine who was on my team at Careerbuilder unexpectedly passed away on that day, leaving behind his wife, who was also a dear friend, and his son. In December, a friend of mine from high school unexpectedly dropped dead in the middle of his parents’ living room, leaving behind his children. During Christmas, we lost another friend from Careerbuilder, on the finance team that worked closely with the sales teams. And there were others. That’s not even counting all those I knew that were going through their personal struggles and tragedies.

I’m not sure if she said it, but I thought that I read she did, in any case, said best by General Organa aka Princess Leia aka Carrie Fisher:

“This is life. When you suffer loss, you can’t change the circumstances, but you can choose how you respond. You can quit, disengage, become bitter or you keep living, loving, and finding joy. It’s not easy. It takes courage. And hard work. But I believe it’s worth it.”

For some, along the same lines, the election brought out the worst in people. Those that lost forgot that those that won this term lost the last two. Those that won forgot that they lost the last two. Because neither side was really willing to step inside the other side’s shoes, and lost the memories of the election before last, the divide in the country that had been building the past twenty years came to a head, highlighted and exacerbated by social media. And that made me sad, especially because I knew so many of the people on both sides were really good people, among the best quite frankly, but let politicians and the media exploit them, social media giving them a platform for rhetoric.

Number EIGHT — ME.

While I made a commitment to myself to be with those that I loved, I spent more time by myself than at any other time in my life. More than anything, that’s what’s characterized my time in Northern California. I have a disparate network of close friends in the Bay Area, those that I had already known, as well as those that I’ve met while working in technology. Despite those relationships, I devoted so much time to self reflection, to meditation and to prayer. Much of it manifested itself physically by going on hikes, mostly with my dog Taylor, who is literally the gift that keeps on giving. Every. Single. Day. I devoted more time to writing. I devoted more time to painting.

I also continued something I’d been doing for quite some time. I spent a portion of my day, usually the very first thing in the morning, saying thanks for the things for which I was thankful. Focusing on what I had and what I had been given, instead of what I didn’t, always kept me from the rabbit hole of victimhood and negative thoughts.

Reflection. Meditation. Prayer. Gratitude. Hiking. Writing. Painting. The combination of all of them has led me to be me, as I continuously try to become the best version of me that I possibly can. On 22 December 2008, I celebrated the eight year anniversary of getting hit by a car. I celebrated life. No question, that singular moment has contributed a lot to my perspective on life.

2016 saw the best of times. 2016 saw the worst of times. The Doctor I thought summed it up best.

“Things end. That’s all. Everything ends, and it’s always sad. But everything begins again too, and that’s always happy. Be happy. I’ll look after everything else.” Doctor Who

2017 is just beginning.

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