How does it connect to the bigger thing?

It is amazing to me how much this question repeatedly shows up in many areas of my life.

When I’m leading product discovery sessions with clients and trying to figure out what to build and when, I am constantly asking how it will tie back to the bigger picture business goals.

When I’m coaching founders about how to navigate a difficult decision, I invite them to consider how this decision impacts the bigger vision of what they want to accomplish.

When I’m planning the next 1 - 3 years from a personal perspective, I am evaluating how it aligns with my understanding of why I’m here on this planet.

When I look at my own life and get discouraged that things feels too disconnected, I remind myself to ponder how it is connected to something bigger than my interpretation of myself.

Zoom out. Like all the way out.

And if you can’t connect the threads to the bigger thing, it’s either not aligned or you are still missing some of the pieces of the puzzle to make the connections. The discernment between those requires practice and intuition and building that skill will provide you with the ultimate navigation system.

If something is truly not connected, we can ruthlessly and confidently move on to the next thing.

How does leadership become contagious?

I went to dinner last night with a few dear friends. It’s the type of dinner I hope to still be having 30 years from now: inspiring, though-provoking, good food, great conversation and even better people.

Something happened that I wasn’t expecting though.

One guy had a career year and got a massive promotion. That wasn’t surprising and is well deserved.

What caught me off guard was how much him being on fire and aligned with his vision impacted me. I don’t work with him, his promotion doesn’t directly impact me, and yet I felt lit up and more connected to my own vision.

It’s no wonder that every manager who reports to him was recognized by the company for their performance this year. That shit is contagious. I caught that from eating delicious meat at the same table as him, so I can imagine how his team feels on the daily.

When leadership is done right, it becomes a self-perpetuating cycle where each individual is inspired to step up in their own leadership. This doesn’t happen overnight, and yet it can very quickly ripple through an entire organization. When you see these leaders in action, you realize that they are worth their weight in gold.

What is a game that's rigged in my favor?

Many lifetimes ago, I became immersed in the game of blackjack. I read all the books, online forums, studied the greats and practiced daily.

It was a wild ride that ultimately ended up with me being able to buy an apartment when I graduated college.

It was a game where I was able to eek out a tiny advantage. Math, statistics, probability, memory, socializing and the ability to handle my alcohol allowed me to grind out some wins and a whole lot of free comps which were a very welcomed upgrade over my normal college life.

The biggest takeaway from that time, aside from the emotional resiliency of being able to handle swings of 1000s of dollars in seconds, is to play a game that is rigged in my favor.

The easiest way to identify the games where I have the most advantage is to look at the unique combination of my gifts.

What is the intersection of things that I'm good at that many people are not?

• Entrepreneurship & problem solving
• Influence & business development
• Technology & product development
• Leadership

These 4 areas have been the focus of most of my adult life and have produced outsized results for me. The places where I can naturally excel are the roles that allow for some combination of these skills to shine. The more the merrier.

It's all too common to spend time playing a game we can't win, don't want to win or where we don't have any tangible advantage. If the goal is to out-produce our potential, then the starting point is to triple down on our unique combination of genius.

The games I'm playing these days are much different than the games I played as a know-it-all, "can't tell me nothing" college kid. But. They are still very much architected in a way that I'm more likely to win than lose.

How do I come up with my theme for the year?

At the beginning of 2018, I gave up any form of resolutions and made the decision that picking a theme for the year felt more appropriate for me.

At that point, I decided that 2018 was going to be the Year of Ultimate Alignment.

This came from a belief that there was a lot of internal work for me to do that year. My intention was to re-calibrate my internal compass and strengthen my trust in my own discernment and decision making. I deepened my yoga and meditation practices. I participated in some other-worldly "team building" activities. I spent a lot of time in nature. And I did my best throughout the year to checkin with my own internal guidance system before taking action.

Then there was 2019. Last year was the Year of Surrender.

Whether I truly wanted Surrender to be my theme for the year or not is hard to say. But it was very clear that's what was happening, and I went with it. I surrendered to Surrender being my theme for the year. I left my leadership position in a company I previously believed was an organization and the people I would work with for the rest of my life. I went through a hellacious experience with the people renting my home which became very costly financially, mentally, spiritually and emotional. And ultimately, I spent a lot more time listening, saying no and letting go than I did of actually accomplishing anything. Weirdest year of my life. But it also left room for me to fall in love with an incredible woman in a situation that most people could never understand. In a sense, we both were fully surrendered to what was possible against the odds, and it's been a beautiful adventure ever since.

That brings us to 2020. The start of a new decade.

There's so much pressure to pick the perfect theme for this new year after how on point the last two were. Actually, I'm just messing around. There's no pressure at all.

I'm sitting here with no theme at the moment, and I'm perfectly okay with that.

The beauty of these themes and the reason why they are a year long journey is that they take time to learn, develop and fully integrate. Allowing these themes the proper time that they need breathe and grow feels like putting on a new piece of armor. They become part of my identity and who I am.

And so, even though I don't have a theme for this year on January 4th (gasp!), I fully trust that the theme will reveal itself soon.

Thanks to my Alignment armor I am certain that I will be able to find the exact right theme and say no to everything else. And thanks to my Surrender armor, I don't feel the need or pressure to force something to hit some arbitrary deadline or outcome.

I know that this year's theme will come from me listening deeply, being observant to what life is showing me and rejecting any good themes to leave space for the perfect one to walk into my life.

Why is Alignment so important?

If you asked me 5 years ago to define alignment, I probably would have said something about the wizardry of a chiropractor. And then a series of unaligned events took place and one actual wizard appeared in my life.

Since then, I've been obsessed with Alignment.

Here's a wonderful quote I saw today:

“Take up one idea. Make that one idea your life. Think of it, dream of it, live on that idea. Let the brain, muscles, nerves, every part of your body, be full of that idea, and just leave every other idea alone. This is the way to success.” – Swami Vivekananda

The way that I think about Alignment these days is a strange and involves some engineering.

Whether its the Alignment of a team or just our internal Alignment within our own mind and body, I like this metaphor. Picture a bunch of row boats towing a much larger boat. Now imagine only 10% of those boats are rowing in the direction you want to go and the rest are either not rowing at all, rowing in their own direction or worst of all rowing in the opposite direction. In this case, you are not moving that large boat very fast if at all, and the 10% rowing won't stick around for very long.

I think about the metaphor probably every day. I've been on teams like that where everyone is rowing in their own direction. I've had times where internally I've been rowing in different directions. And I've also seen what's possible when true Alignment happens.

This is the difference exceptional leadership can bring to the table.

When you've been in an environment of competing rowers and suddenly all the rowers are working together in synchronization and harmony, the improvement is exponential. This is the way to success.