October 2020: Bold Moves

Turbulence, 2010 Acrylic on Canvas 22_ x 30_ $1650

Pregame players don’t sit on the sidelines. You’re here because you’re all about big ideas. And the actualization of big ideas requires nothing less than bold moves. When my little brother was in his early-20’s heyday, he had a friend nicknamed Bold Dave. I thought this was hilarious and asked where he got the name. The explanation: “Because he’s always making bold moves.” While Dave’s bold moves may have been about [moves removed to protect Dave’s reputation], his moniker stuck with me. I tend to hesitate, trying to make the “perfect” decision, but when I look back on my life, the […]

September 2020: Burn It Down

Carlo Proietto

To understate a Covid silver lining, 2020 has been, if nothing else, a remarkable opportunity to rethink everything. My friends have been considering big changes – or taking the leap and going for it. Moving across the country. Buying the house. Doing IVF. Getting divorced. Getting back together. Confronting family members about long-hidden issues. Finally leaving New York. Nothing sparks change like a crisis. Limping along with systems that aren’t working just doesn’t cut it anymore when major events expose weaknesses that threaten core values, connection, and opportunity. Let’s hope our personal reinventions are foreshadowing of change in our country. […]

July 2020: Awakening

never waste a good crisis

And then suddenly, everyone woke up. Well, not everyone. And not fully awake. But no one can deny that the past month has seen a remarkable wave of increased awareness in America about the perpetual problem of racism, and how society cannot be healthy when we insist on viewing ourselves as individuals whose actions and worldview don’t affect anyone rather than part of a system where everything is connected. To me, waking up is the point. It’s the process. As in, THE process. The purpose of life. To be continually evolving, learning, growing, connecting. It’s difficult because there is no finish […]

An American Intervention

whitney plantation

Photo: The author inside a human cage at The Whitney Plantation, the only American plantation restored to honor the memory and plight of enslaved African people. Welcome to the week of waking up. I am watching the stream of Official Statements from various organizations from the back of the room, leaning against the wall with my arms crossed, side of my mouth turned up and brow furrowed. This week of black squares on social media has been what the rainbow logo is to Pride week: easy, convenient, trendy. Meaningless unless followed by tangible, measurable action. Businesses that declare support for […]

June 2020: Career Stories

map

Watching President Obama’s virtual commencement addresses in May, I was inspired to do something to support this year’s grads. If I could give them one gift, what would it be? The answer: self confidence. Not in the swagger sense (although I wish them some of that too). I’d wish them that centered, calm state that they’ve got this, that things will work out fine, that it’s all good, and that a sense of “it’s all just a game” can relieve the anxiety of feeling like you have to have it all perfectly planned out from the kickoff. The best way […]

April 2020: The Coronavirus Interlude

empty street

And then suddenly, everything changed. We interrupt our regularly scheduled magazine issue to start unpacking the only topic that matters right now. On April 1, 2020, we find ourselves in the middle of a global pandemic. Approximately two weeks from its peak in America. But this is only the beginning. We will be changed, permanently, by this uniquely global event. While it’s difficult to editorialize about the coronavirus as it happens, lacking any clarify of hindsight, we decided to use writing as a sort of therapy to explore what this means now, and what it could mean. We are in […]

March 2020: Arts & Culture

Stories Being Told To The Sky, 48in x 48in, oil on canvas

I have a confession to make. I only read nonfiction. Well, not entirely. I read a fiction book on vacation last month (thanks, Kevin Kwan!), and before that (cough), on vacation two years ago (thanks, Haruki Murakami!). As your resident goal-getter, nonfiction just seems so much more… important. Who has time for frivolity when there are things to learn, goals to accomplish! But since the smartest people I know spend time not just with nonfiction but also with novels, I finally stopped to wonder if I was missing half the story. Ironically, the arts – yes, fiction – can be […]

February 2020: Legacy

ripple effect

We all have an urge to create. To put our stamp on the world. To leave a legacy. I learned this from Nick, a friend with whom I’d recently reunited. He had become a priest, serving as a hospital chaplain. Sitting in Madison Square Park, we caught up over coffee from the Mud Truck one spring afternoon. I was fascinated by the sheer amount of time he had spent with dying people; more than anyone else I knew at our age. I asked, “What’s the one biggest takeaway you have from being around people at the end of life?” He […]

Goal Clarity: 10 Questions to Ask Yourself

Impression 2018 (Detail)
90in X 55in X7in
Pigmented Wax, Fabric, Wood, Thread

Need clarity on your goals, your direction, your next steps? We talk a lot about setting goals at Pregame and in my book Game Plan. The Game Plan workbook is a great way to get clarity for your New Year – create a little goal retreat on your own or with a friend. To pregame that work, start with our Clarifying Questions. I try to do them a couple of times each year and it gives me clarity on what my goals should be right now. It’s like being on a really long road trip and taking a rest stop; […]

January 2020: Clarity

Between 2017 (Detail)
Pigmented Wax, Fabric, Wire, Wood, Canvas
30in X 24in X 10.5in

Welcome to the new decade! (Well, yes, chronology purists, it doesn’t technically start until 2021, but play along.) As you know, we’re all about the New Year: fresh starts, renewed vision, and best of all, new goals. In the year 2020, it’s impossible for us to resist the obvious metaphor: perfect vision. When deciding on the next goal or even just the next step, how do we get clarity? Clarity on what we really want (versus what others want for us), whether now is the right time (or we’re hanging on to something from the past), and why we’re going for it […]