Photo by Jasmin Sessler on Unsplash

I’ve been spending a fair amount of time and effort on self-improvement in the last couple of years, in the name of being happier with myself and being a better person to be around.

Much of the behavior I’m trying to modify seems to originate from a primal sense of fear. I’ve started to unpack this pattern using the famous “Five Whys” method of root cause analysis originated by the Toyota Production System. The Five Whys says that it takes, on average, five questions in a row to get to the actual root cause. (You may now roll your eyes at the nerdy reference).

Let me share an example.

I’m driving a major initiative at work that is foundational to our business growth strategy. It’s not going as fast as I want, or as my boss wants or probably as anyone wants. While the reason for the rate of progress is a typical one – limited resources – I still feel anxiety about the situation all the time.

First question: What am I fearing as a result of going too slow?

My company is owned by a private equity investor. At some point there will be a liquidity event; an IPO or sale of the company. I fear that my initiative will impede our ability to achieve this expected outcome.

Next question: why is that outcome important to me personally?

Well, I’m a shareholder and have a goal of saving more for my retirement with the proceeds of my stock options.

Next question: why is saving more for retirement important?

I want the security and the optionality of retiring “comfortably”.

Next question: what is a “comfortable” retirement?

We’re only four questions in and I’ve already exposed the fear and flaws in my thinking.

The reality is that I have already funded my retirement, at least to the point of being assured of having a roof over my head, food to eat and access to healthcare.

Yet I fear it’s not enough. “Not enough” simply means that constraints will exist on how I retire. Maybe I have to curtail the size and quality of the dwelling I live in. Maybe I can’t live in certain communities or even states. Maybe I have to live in another country to satisfy a criterion like being near the ocean.

Wanting something more than basic needs is fine to desire and strive for. But why is that connected to any present-day feeling of fear?

What makes this type of fearful thinking even more absurd is that we all know happiness is a function of the quality of our relationships. Will I have friends when I’m retired? Of course I will. All of us will.

This isn’t an essay about the evils of materialism. Money has a place in making us happy, at least as it relates to meeting our basic needs.

Rather, I’m trying to better understand where my own sense of fear comes from. I’m trying to name fearful thinking for the useless role it plays. I’m trying to reduce or eliminate fear in order to behave differently and better.

My belief is that fear informs many of our behaviors. We each have an opportunity to confront it, manage it and be more like the person we aspire to be.

Photo by Ellen Auer on Unsplash

The pandemic has made all of us wait. And wait some more. And there’s more waiting to come.

My office is open again. For those who chose to return, they must wear a mask at all times. So now we have Zoom meetings that include people joining from the office in masks. What was already a medium that impaired communications just got more challenging with masked participants. So we wait for the time when we can have unmasked Zoom meetings, or better still face-to-face conversations in the office. Probably months from now. Waiting.

We’ve waited to get vaccinated, in order to resume normal things in life like dining indoors, meeting up with friends & family, or getting on an airplane. Except the vaccination isn’t (yet) a golden ticket. We wait to learn the risk of transmitting the disease while vaccinated, so that we can join the company of the unvaccinated. Or we wait until herd immunity arrives, if ever. Waiting.

Different people have coped differently with the waiting. Some have bent or broken the rules and engaged in pre-pandemic behaviors. The waiting was too much to bear.

Some have done what was asked, and curtailed their lives while waiting. Which means some good days and some bad days of waiting.

Some have used this as an opportunity to redefine their lives or take up new hobbies. I’m not sure how many have turned the pandemic into a fully positive experience, but I doubt it’s many of us. We’re too social as a species to retreat to a monastic lifestyle.

I’ve avoided the temptation to bend the rules and take risks, keeping society and the safety of my very small pod of friends and family at the forefront of my mind. Therefore, there have been some good days and bad days trying to be patient. Mostly it’s exhausting to be waiting over a year with many months to go until one can lead an unfettered life.

Yes, I’ve focused on self care as a coping mechanism. Daily exercise, healthy eating, moderated drinking, reading & writing, even meditation. All of these techniques may have made things easier, but not easy.

What I hope is that with each progressive step towards normalcy, each of us gains an appreciation for what we gain back. The camaraderie of being on an airplane with 300 strangers to an exciting destination . The coziness of sipping a coffee in a cafe, surrounded by the hum of other conversations. The collective energy of attending a sports event or concert.

In this pandemic, we’ve learned how to be alone. Can we learn how to be better together?

I’m glad Joe Biden was elected President. But it wasn’t a massive repudiation of Donald Trump. Not given the 70 million votes that Trump received.

In trying to make sense of this election and what is means going forward, it’s important to distinguish between Donald Trump and his supporters. It’s one thing to dismiss Trump the person but you can’t dismiss his large base of supporters so easily.

I haven’t hidden my disdain for Trump the person. I think history will judge him in 50 years from now as the worst President ever. I predict he will be seen as:

1. a criminal, both in his business affairs and while President
2. immoral, or perhaps amoral
3. a victim of psychological disorders, likely sociopathy and/or narcissism
4. grossly incompetent

What’s more important is to understand his base of supporters. They represent a huge portion of Americans. And they will be here tomorrow.

In a two-party system, Trump’s base is by definition a coalition of multiple groups and reasons to support him.

For example, one faction is anti-abortionists who’ve been on a decades-long quest to overturn Roe v. Wade by altering the composition of the Supreme Court via control of the Presidency and Congress. They’ve been transparent about this for a long time.

Trying to make sense of all of Trump’s coalition is where I get confused. Even in my own family – comprised of smart, kind and accomplished people – it’s a mixed bag of pro- and anti-Trump support. I don’t understand it.

I watched Fox News this week. Not something I generally do. It was awfully different than the many centrist media outlets that I consume daily. I don’t think Fox taught me much. I saw a ton of evidence of how different my opinions are to their broadcasters and presumably their viewership. But I learned very little as to why those differences exist.

Yet understanding both parties’ coalitions is what’s going to keep this great country together and making progress. We must understand each other. We must have empathy for each other.

This doesn’t mean compromising one’s own values. Or unconditionally accepting the behavior of others. But understanding and empathy are required in order to find any common ground. And common ground is what we need most right now imho.

So my quest is to keep trying to understand what I don’t. Perhaps that quest would serve each of us well.

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.