I first traveled to California in the early 90’s. I was accompanying a girlfriend on a business trip to San Francisco. We stayed at the Fairmont Hotel on the top of Nob Hill. The views were breathtaking. We ate amazing food. We spent a couple days in Napa Valley drinking fine wine.

I was smitten.

By 1995, I was working for Pure Software in Sunnyvale even as I lived in Boston. I spent 25 weeks that year in Silicon Valley, traipsing around the region developing partnerships with other tech companies. For example, I witnessed the birth of Siebel Systems. At the time they were a group of maybe 20 people working from folding tables, on their way to becoming a billion-dollar juggernaut.

I often landed at SFO at dusk. I would emerge from the terminal and feel the cool Pacific breeze carrying the scent of eucalyptus trees down from the ridge above San Bruno. The smell of eucalyptus trees at dusk is forever a reminder of those magical early days traveling here.

In 1995, I knew somehow that I would end up living here. Or at least I knew that I wanted to. When I decided to come here in 2012, I estimated I had visited the Bay Area over 80 times already. I was already deeply in love with California.

This year’s wildfires and pandemic have got me reflecting on why I love this place. Without the ability to travel elsewhere, I’ve been exploring the state, reminded anew what makes this a unique and special place in the world.

Natural beauty and conservation

It’s obvious to say, but we have a magical coastline. And towering mountains. And desolate deserts. And fertile valleys, remnants of ancient seas.

What’s truly special is the spirit of conservationism behind our natural wonders.

The Sierra Club was born here and wields great influence over how we now see and protect our natural gifts.

The laws behind the California Coastal Commission ensure the public’s access to our beaches. This is unlike where I grew up in New Hampshire and Massachusetts, where private landowners can severely restrict beach access.

The Peninsula Open Space Trust has dedicated huge portions of the Santa Cruz Mountains as perpetual wilderness trusts. Where else in the world can you access such a beautiful wilderness half an hour away from millions of people? What foresight and what a gift to us from a prior generation of settlers here.

Our mountain ranges are largely enshrined as National Forests, State Forests, trusts and other parks. Yes, you can still see the blight of aggressive logging but thankfully that era seems to have passed. The mountains are healing.

(I’m thinking about my beloved Santa Cruz Mountains a lot these days as they burn.)

Diversity

It’s a melting pot here. My son’s school found over 35 mother tongues in the student population.

Every race, country, religion and subculture is represented here. You can find a community of interest for anything. And you’ll be exposed to different people continually.

Are we free from bias and racism here? Not even close. But if you value diversity and strive to have it positively affect your mindset, this is a place for you.

Spirituality

There’s a lot of spirituality here. Maybe it’s inspired by the natural beauty of the place.

You’ll find spiritual practices like mysticism and quasi-religions. Which has informed negative stereotypes about the place.

But the majesty of our nature is real. And it moves many people, as it does me. There is a spirit to this place.

Industry

This one is almost too obvious to say. If you’re in the tech industry like me, it’s the world capital of what we do. Yes, other places have tech and successful companies. But not like here.

You can be an elitist here. Measuing yourself by how many millionaires (or billionaires) are in your social circle. And by your own financial worth.

You can do bad things here. Like Mark Zuckerberg, and his massive personal wealth derived from distributing and amplifying disinformation, propaganda and hateful speech. By the way: fuck you, Mark.

Or you can be humble and appreciate the amazing collection of smart people working as a community. Creating and building great things that benefit society. I know many, many people like this, who pay it forward.

All of these types of people are here at the same time: hubris, elitism, naked & craven capitalism. But magnanimity, humility and social purpose can easily be found here. I wake up in the morning proud of my work along with many others in protecting the world’s internet users from the bad guys.

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It’s easy to put California down. We’ve got lots and lots of problems. Racism. Financial inequity. High cost of living. Pollution. Congestion. Global warming and natural disasters.

Despite all of this, there is so much to love and appreciate here. Now more than ever.

I leave you with some pictures of my beloved California in recent months.

I was listening today to a session at work where my Black colleagues spoke about their experiences with discrimination. It was moving in so many ways. Their courage to share with their colleagues. The profound and troubling stories they told. The empathy they helped me better develop.

Yet I’m interested to work through a dilemma. How can racism and bias exist, when our American culture is so enriched by the contributions of Black artists?

Consider the extraordinary gifts we’ve been given:

Jazz

Jazz, the greatest American art form, wouldn’t exist without Black artists.

Ella Fitzgerald’s sweet and pure voice.

Billie Holiday courageously singing Strange Fruit in an era where addressing the topic of lynching might have gotten her killed.

John Coltrane’s saxophone; torrents of notes mixed with sustained wails that convey so much emotion and spirituality.

Art Blakey’s drumming. And his mentorship of young musicians, like Wynton Marsalis.

Charlie Parker. Sarah Vaughan. Louis Armstrong. Duke Ellington. Dizzy Gillespie. Miles Davis. Charles Mingus. Wayne Shorter. Herbie Hancock. Thelonius Monk. Joshua Redman. And so many more.

Rhythm & Blues, Soul, Funk

Otis Redding. Marvin Gaye. Every Motown artist. Stevie Wonder. Alicia Keys. Erykah Badu. Aretha Franklin. Diana Ross. John Lee Hooker. Howlin’ Wolf. Muddy Waters. Curtis Mayfield. James Brown. Tina Turner. George Clinton. Gary Clark Jr. Janelle Monae. Koko Taylor. Luther Vandross. Prince. Ray Charles. Sam & Dave. And so many more.

TV and movies

Jordan Peele. Sidney Poitier. Alfre Woodard. Viola Davis. Octavia Spencer. Denzel Washington. Morgan Freeman. Halle Berry. Angela Bassett. Forest Whitaker. Taraji P. Henson. Don Cheadle. Mahershala Ali. And so many more.

Journalism

Ed Bradley. Ta-Nehesi Coates. Charlayne Hunter-Gault. Gwen Ifill. Oprah Winfrey. Frederick Douglass. And so many more.

Humor

Richard Pryor. Dave Chappelle. Chris Rock. Eddie Murphy. Wanda Sykes. The Wayans brothers. Flip Wilson. Dick Gregory. And so many more.

This is just a sampling. These names are not Black artists. They are American artists. They have helped create the very fabric of our culture and society.

And so I keep asking myself; if these artists have contributed so much, why do we have racism in the face of their brilliance? I don’t have the answers. But I will keep asking the question.

Photo by Renee Fisher on Unsplash

Today, I finally deleted my Facebook account. I agonized over this decision for months if not years. I knew that if I left, I would lose touch to some degree with the many friends I’ve met around the world.

However, I couldn’t any longer look past Facebook’s failures of content governance.

It’s a well established fact that nation-states have used fake accounts and Facebook advertising to spread misleading political content or worse. It’s a well-established fact that hate groups have disseminated their hateful content over the platform.

These things happen regularly and at meaningful scale. It’s not some anomaly that can be easily explained away.

The recent advertiser boycott was met by apparent defiance by Mark Zuckerberg, wherein he told large advertisers that Facebook will not work to block hate speech to its best ability. This was the last straw for me.

As hard a problem as governance might be, I can’t be part of a community that accepts “some” hateful or misleading content. There is nothing to “tolerate” here.

Facebook is hiding behind free speech as the reason they can’t or won’t deal with the problem. I call bullshit. They don’t want to be inconvenienced by the effort it takes, or perhaps the revenue loss they will incur by making it harder to publish content and ads on the platform. Other social media platforms like Twitter have acted, even as they can do much more.

Every other mass medium enforces content restrictions. Newspapers don’t publish hate speech. TV broadcasters don’t. Why is Facebook somehow exempt? They’re not, or at least they shouldn’t be.

You might not agree with me. And I respect that.

But for me, Arthur Ashe’s quote has resonated as I’ve been thinking about racial biases and injustices:

“Start where you are, use what you have, do what you can”.

What I can do is disassociate myself with something I don’t agree with. So, buh-bye, Mark.

Listening to sublime jazz is like experiencing a great team at work. Each performer is individually brilliant yet it’s the collaboration and teamwork that makes it sublime. When I worked for Chris Young at McAfee, this was the key point of a speech he made. So I’m riffing on his talk (like jazz itself).

In order to draw the analogy to teamwork, a brief digression about jazz is order.

Many jazz performances follow a time-honored structure. Each song begins with a melody – or coda – and then the group moves on to the improvisation phase. One or more group members improvise a solo. Once that phase is over, the group returns to the coda and the song is brought to a close.

The improvisation is where the magic happens.

Good jazz is when each improviser expresses their individual mastery during a solo. Perhaps they are technically brilliant with their instrument and use the solo to demonstrate it. Perhaps they want to challenge the listener with the extremity of their improvisation, by departing far away from the mood and tone of the coda.

But in my opinion, great jazz – the sublime jazz – is when the soloists honor the coda and play off of each other during the solo. The soloist is in the lead, but their bandmates are improvising to some degree at the same time. You can literally hear the group respond to each other as they go.

What’s exceptional when this happens is the trust, vulnerability and courage required of each member. A soloist without others improvising is in full control of their performance. But when a soloist and their bandmates improvise at the same time, everyone is engaged in collective risk-taking.

Sublime jazz is how I think of great teams. Every person is playing to their strengths and contributing their brilliance as “soloists”. But they are doing so in the context of collaboration, mutual trust and risk-taking. Each team member is contributing to the collective whole, not for the sake of proving their own abilities but in order to improvise together towards great outcomes.

How might you play like jazz at work? First, focus on creating an environment where each team member is encouraged to be their brilliant selves. Yourself included.

Second, focus the team’s attention on collaborating around each person’s brilliance. There’s a secret to improvisational comedy, which is to use “yes, and…..” instead of “yes, but…..”. Any person can lead with an idea, and the rest of the team is encouraged to ideate, refine and riff on the idea until some conclusion is reached.

P.S. If you’re interested to hear examples of sublime jazz, Miles Davis’ Kind of Blue is my canonical example. Titans like Miles, John Coltrane, Bill Evans, Cannonball Adderley and Paul Chambers came together, and with very little advanced planning improvised their way to perhaps the most important jazz recording ever made. Recently, I also discovered Matthew Halsall, a current-generation example of sublime collaboration and improvisation. Check him out here.

I’ve had an on-again, off-again relationship with distance running for most of my life. I love the healthy benefits of stress reduction, aerobic fitness, ability to eat carbs without remorse, etc. And the mental test of going further and faster is rewarding too.

Unfortunately, my body isn’t built well enough for distance running. I’d been in an endless cycle of fitness > injury > recovery for most of my thirties and forties. Eventually, I had to give up running entirely about 9 years ago.

Since then, I mourned the loss of running because I couldn’t find an easy substitute. As much as I love hiking, it’s more time consuming to drive to a hilly trailhead, do a hike of multiple hours, and drive home to get the same impact as a 30-60 minute run. So there’s a natural limit to hiking’s frequency and benefit.

In April of 2018, the fitness club I belong to installed solar panels over the parking lot. With that, the outdoor pool went from open & heated seasonally to open & heated year-round. I decided I would try doing some laps in April 2018 in case swimming could become a new running substitute.

5 minutes into my first session, I had to stop. My heart was racing. My body temperature was elevated. I wanted to puke, like the feeling of sprinting for 400 meters around a track. “This is intense!” I thought to myself.

Since then, I’ve slowly developed a lap swimming habit to the point of 3-4 sessions per week for 30-35 minutes each. The results have been transformative.

My aerobic fitness is such that the most challenging hill hikes I take are now pretty straightforward. I’m not at 10k road race fitness, but still.

There’s been a commensurate impact on my muscular fitness. Core fitness in particular is an amazing by-product of swimming. Even as I traveled to India 4 times a year in 2017-2019, I never experienced back pain thanks to a strong core. And other muscles have emerged throughout my upper and lower body.

What’s most amazing about swimming is the lack of recovery time needed. I’ve done laps for multiple days in a row and not felt any soreness or recovery time needed until maybe 4-5 days in a row. That’s a big contrast to the recovery discipline most runners need.

Last, swimming has been a springboard to other fitness habits. From this foundation I’ve introduced things like kettle bell exercises, a little bit of yoga and daily walking.

And of course a healthy body leads to healthy eating habits and positive mental health. Put all of this together and yes, my life is much different today than in recent years past.

If you’re in search of a fitness activity with aerobic and muscular benefits with limited time commitments, I can’t recommend swimming enough. Happy laps!

It was a lot of fun to be interviewed by Career Tiger and talk about career-building, SaaS trends, mentorship etc. Check it out!

What motivates our New Year’s Resolutions is to seek some form of self-improvement.

But here’s the challenge. Positive change and growth require courage. Courage to confront our fears, our guilt, our shame. So much of what holds us back from growth are the fears that hold us in place. Or the shame and guilt that comes with acknowledging that we need to be someone different in order to be better or happier.

I took some big decisions in 2019 about my professional and personal life. Perhaps you did, too. Scary, one might say. But necessary for the sake of one’s long-term happiness.

But I survived those changes. So did you. We all do in retrospect. The fear and shame manifested but subsided. A new normal began to emerge. With growth as a by-product.

For example, I started being more vulnerable with close friends and family. I told them things I never shared before. What I got in return was their own stories and a closer connection. So beautiful.

I also fucked some things up majorly as I tried to change. Fail-learn-grow, fail-learn-grow seems like a cycle without end. And not always in a comfortable way.

We’re all like onions. There are many layers to be peeled to develop a true sense of self. What do we want? What do we need? What is the idealized version of ourselves? Where are the gaps between our ideal selves and actual selves that we need to work to fill?

So 2020 will be a continuation of 2019, asking myself more of these anxiety-provoking questions in search of growth and positive change.

If you’re like me, some answers will be ugly. They will require confronting my flaws and failures and past traumas.

That’s where courage is required. If we can find the courage, then growth can follow.

I met up with an old friend over a beer recently. We hadn’t seen each other in years. An aside: do you have friends where you can go years without contact, and just pick up the conversation as if those years hadn’t passed? That’s the case with this friend.

His story is remarkable. The love of his life passed away years ago. What followed were some dark months if not years. Any one of us would have felt the same.

Except he picked himself up, dusted himself off and took on the challenge of living a fulsome life again. Eventually, he met someone else. And they fell in love with each other. And with each other’s families, including children and grandchildren.

In parallel, my friend had the good fortune to join a really great software company. The company provided him with amazing success and growth opportunities over the years. Including a recent promotion and expat adventure.

Finding love again and prospering in his career while in his 50’s isn’t an accident in my opinion. It’s because he was open to the possibilities. It’s because he seized the possibilities. He made himself vulnerable, especially in falling in love with another person having lost his soulmate. He showed courage.

I think of his story and remind myself how our lives are made up of chapters. Adulthood isn’t one chapter. It can be many. And each chapter, if we choose to start it, can be a path to something new and valuable.

And if we follow the inspiration of people like my friend, those new chapters might never stop opening. All the way to the end of a life well lived.

I was in Ann Arbor recently, visiting my local team there.

Lately, I’ve gotten in the habit of getting up early and starting the day with a long walk. So, off I went with a coffee in hand and Tegan and Sara’s new album in my ears (very good, btw) to explore the vast campus of University of Michigan. Go Blue!

I was reminded how college is where many of us go to find ourselves. Far from our parents’ watchful eyes, we’re free to become whomever we want. For me, this took the form of experimentation and trying on various personas.

College was the first time I was presented with diversity and I was intrigued to know these different people. Coming from the lily-white suburb I was raised in, this was a fun experience.

I got to meet the Ethiopians. One from Addis Ababa, who was very worldly. And the other from the rural mountains, who was a refugee of political violence and had the scars to prove it. I met the Singaporean who loved alternative music as much as me. The Bahamians, whose love of life was just infectious. The Bermudians, who were similar but maybe more reserved.

I met the anarchist. The hippies. The Quebecois. The rural Nova Scotians. The Hongkongers. The mainland Chinese. The Indians. The Ontarians.

People wax nostalgic about college. And for good reason. It can be a very fun time indeed. But it can also be a confusing time. Free to experiment, and confronted with people who are very different from one’s self, who are we really?

We emerge from college with a clearer sense of self, which guides our early adult life. But I don’t think that’s the end of the story. At least it shouldn’t be.

To me, life is comprised of chapters. And with each chapter we have a chance to reexamine ourselves. Do we still believe what we did? Value what we did? If not, what does that mean to the life we will lead going forward?

Perhaps we should maintain the college mindset. We can be constantly exploring who we are and who we want to be. That feels like growth to me.

It was the winter of 1983. I was a senior in high school. I had told my parents that I didn’t plan to go to college that fall. So I didn’t apply to any schools.

As a parent today, the thought of this terrifies me. A college degree is a ticket to lifelong opportunities. So I can only imagine what my parents were thinking at the time. I was in a private, all-boys high school known for graduating 98% of its students to college. And I had enough ability to do the same.

But the reality was a bit different than that first principle of “thou must go to college if you can”. I was suffering from years of depression, my grades had deteriorated in my junior and senior years, I was soul-searching for who I was. I didn’t feel ready to continue the shitty academic experience I’d been having by continuing on to college.

So my dad did something surreptitiously. Knowing he and my mom were about to move back to Nova Scotia from New Hampshire to be closer to my ailing sister, he called the dean of admissions at Acadia University in Nova Scotia.

Somehow my dad got me in over the phone. He must have been a pretty good salesperson, because Acadia has been ranking in the top 3 schools in Canada for decades, often ranking #1. And it was weeks past the application deadline.

My dad came to me afterwards and basically said, “write your application and essay and you’re in”. For reasons I can’t recall or are buried in my psyche, I went along with it.

The first years at Acadia were a continuation of my struggle. But somehow I stuck with it and gradually became engaged as a student. I graduated with mediocre grades but at least I had that piece of paper. The thing that opened the door to future opportunity.

Parlaying that degree into career opportunity back in the United States wasn’t easy, but we’ll save it for another story.

There’s multiple lessons to be taken from this story in my opinion.

First, even in the times of struggle and failure, an opportunity exists if you choose to take it.

Second, we can fight ourselves over seizing opportunity. Perhaps because of limits to our own self-esteem.

Third, there are always people in your life who are willing to help you and give you that opportunity. Bob Stead was the Dean of Admissions at Acadia. He had no reason to admit me. But for some reason he did. I am forever thankful.

Have you ever met the type of person who was a class valedictorian? The one who was both gifted and driven? Who got into Stanford, or Harvard, or Princeton? Who got hired at Bain or Goldman Sachs? I know some of these people, and I’m not one of them. Never been.

So if you’re not that “achiever” persona how do you succeed?

Fail forward.

“Failing forward” for me is a metaphor for seizing opportunities when they are there, risk-taking, and learning from failure. In my case, I don’t have that valedictorian pedigree. So to the extent I have built a successful career, it’s been from a series of fail-forward events, originating all the way back to high school.

Only as I get older and wiser do I see the outright merits to embracing this idea and accepting it as a blueprint for success.