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.

I’m neither a musician nor a composer, but I do love music. And one song has me trying to deconstruct why I like it so much.

Here goes my attempt to explain the perfection of Billie Eilish’s “I Love You“.

First, the song is slow and spare. Very few notes and words. This negative space gives every note and word the ability to have maximal emotional impact.

Second, she chooses words with very common ending sounds like “oo” and “eye” so that she has many words to choose from. Those well-chosen words can be short and simple but still convey intense meaning.

This is a kind of Hemingway-like genius. As the master himself said:

If a writer of prose knows enough about what he is writing about he may omit things that he knows and the reader….will have a feeling of those things as strongly as though the writer had stated them. – Ernest Hemingway

Third, she sings the verses very quietly. You’re drawn in to listening the way you listen harder to someone who’s whispering.

Fourth, the refrain builds from that quiet baseline to a crescendo of a held word, along with a single held note on a bass guitar or string instrument. “I love yooooooooooooou”. This prolongs the climax of emotion and the point of the whole song..

So that’s it. Slow and spare. Simple, emotionally laden words. A quiet that draws you into listening. And a refrain that brings home the emotional point of the song.

Have a listen for yourself.

• 

I’m playing around with a book concept. Something I probably won’t get to writing for a while, given all that’s going on in my life.

But the central premise is that all forms of personal and professional growth are borne of risk-taking and failure.

This isn’t a new idea.

So why don’t we take those risks? Why don’t we maximize our learnings from failure? Perhaps these questions do merit writing more about.

I’ve written only a little bit about the failure of my startup Bluenose Analytics, here and here. But in the years since, I’ve reflected extensively on the experience and what I could take away from it.

First lesson: adversity builds courage and much more. For example, the utter magnitude of Bluenose’s failure, and my accountability for it, mean that I won’t experience anything so monumental (unless & until I start another company!).

The effect is that I don’t freak out over risk-taking. New challenges that I might never have faced before become less scary. Scary, but less scary. So I’m now inoculated from the paralyzing fear of failure.

So remind yourself: at some point in your past you’ve taken risks and survived them. Even overcome them or outright prospered. Which can increase your appetite for risk-taking from here forward. If you’ve been so risk-averse in the past that you can’t draw lessons from risk & failure, then ask yourself what you are waiting for?

Second lesson: failure can create resiliency. But failure can also create negative feelings of defeat. So how to become resilient?

I think the key to failure is to own it. I *never* characterize Bluenose as anything but failure. Failure of the business and failure of me. Despite the fact that we achieved many things to be proud of. But “owning” failure means to not qualify it as somehow being less than it is. In my case, I lost $13m of famous investors’ money, denied my employees the ability to experience success from their hard work, and disappointed our customers. I own that no matter what else happened.

And to own it is to be able to move past it. I speak openly now about this failure, without sugar-coating or avoiding it. Because I can use this experience in many positive ways. This is resilience.

Third lesson: you can build stronger connections from failure.

In my case, I think one benefit of failure is that I am more vulnerable and engaging to the extent that I talk about it. As a leader, it’s tempting to try to project perfection. But what people really want from their leaders is a sense of connection. I’m good at projecting confidence, so using failure as part of my narrative is important to remind me and others of my utter humanity and fallibility.

Building connection from vulnerability can also position us to better empathize with others who are working through their own challenges. That empathy creates the pathways to be helpful by listening, questioning and advising.

So risk and failure can build courage, resiliency and connections. When you frame it like that, what’s the downside?