2020: Year In Review

Leadership, Legacy, Life

At the end of last year’s Review, I wrote: “2020 is promising to be a year of great transformation.”

As we all know at this point, 2020 was a lot of things. It seems fair to say it ended up being quite a year of transformation — in ways many of us will be unpacking for years to come.

Here, I’ll review its impact on me… read on if you’re ready for some pretty big stuff I haven’t talked about publicly before.


Goals For 2020 + Reflection

1) Physical/mental/emotional wellness

Let’s jump right in, shall we? Who could’ve guessed the extreme importance of this goal in 2020

Coming into 2020, I knew this was going to be important for me (thus the goal), but I had no idea so much of my year would be so intently focused on it.

Toward the end of last year and throughout much of this one, I experienced more anxiety than I ever have, including the occasional and never-enjoyable random panic attack. P.S. The more people I talk to about this, the more I realize just how many of us have had this terrifying experience. If you’ve ever been in this spot and you felt alone or shame or anything related, please know you are very much the opposite of alone.

Overall, through a regimen of almost-zero-news, better work boundaries, regular therapy, more exercise, a bit of medicine, assistance from the amazing Dr. Carly, and a huge number of epsom salt baths, I’m happy to say I feel like I’m in a profoundly more healthy spot now than I was at the end of 2019.

2) Build more great friendships in Denver

This will obviously be my go-to reference when I need to make a comical point about setting goals anytime in the future! Geez, this one was… hard. I guess I technically succeeded, but only because I put no numerical goal on it…!

3) Publicly release the new app

Hell yes we did this, and with one of the biggest companies on earth no less (a bit more on this below)! That said, we didn’t really do a proper public launch — 2021 will be the year for that.

4) Write and publish three new articles every month

I think I only published three actual new articles this year:

  1. Avoiding The Catastrophic Technical Debt Of Sub-Par Culture
  2. What We Want You To Buy
  3. Should We Abolish The Electoral College?

But despite the lack of “articles,” I’m going to call this goal a relative success because in May, I also started a podcast about an idea that’s meant a lot to me for a long time: The Work Revolution. Under this banner, I wrote and performed 23 monologue-based episodes in less than six months. Obviously, creating this was a huge amount of writing.

Here are my personal Top 5 favorite episodes (listening time in parenthesis):

  1. Episode 4: The Future Isn’t What We Think It Is — May 18, 2020 (2:27)
  2. Episode 7: Even If We Could Go Back, We Shouldn’t Want To — May 26, 2020 (2:39)
  3. Episode 10: The Tunnel Of Death & The Rebirth On The Other Side — June 9, 2020 (10:28)
  4. Episode 14: Why The Work From Home Transition Is So Damn Difficult — July 7, 2020 (6:35)
  5. Episode 21: Billionaires, Oxygen, & The Purpose Of Work — August 25, 2020 (5:18)

Side note: You may notice the tone of some of the topics I speak and write about have drifted towards the “political.” This happened because this year I stopped seeing “politics” as being “separate” from the rest of life, especially when it comes to how the world works. I explain this insight in detail in this podcast episode, if you want to learn more. I suspect it’s safe to say this epiphany will transform my work forever.

5) Zero biz travel that isn’t my highest & best contribution

Well, this one did happen… a pandemic is a terribly unfortunate WAY to reach this goal, of course, but I suppose I accomplished it nonetheless.

6) Reboot Work Revolution

This didn’t look at all like what I envisioned back when I wrote this goal (I was picturing lots of live events!), but the reboot definitely happened and I’m very proud of the content produced this year.


Important Events From 2020

In years past, this section was primarily about social events, travel, speaking gigs, etc. — all things that were off-limits most of 2020. But that doesn’t mean important things didn’t happen… in fact, my statement above about 2020 being a year of “great transformation” was poignantly true for me. Here are some of the most important things that happened in my life this year.

  • YEC Escape — I’d been wanting to attend this event for years and finally got to go. It was tremendous fun, and fortunately it happened in January before travel lockdowns began (I remember reading about “the mysterious new virus in Wuhan” while I was traveling to/from Park City).
  • Conscious Uncoupling — Allison, my long-term partner (and mom of my two kids), and I decided to consciously uncouple our marriage this year. This transition, which has been in process for the past couple years, was both brutally hard and very much based in love. We remain good friends and great co-parents. My deep and sincere gratitude to the fabulous Jen Joyce for her beautiful counsel throughout this journey.
  • A New Bike — Seems like a small thing, perhaps, but this brought me a lot of joy. I haven’t owned a bike in probably twenty+ years, and somehow early in the summer I was able to track down one of the last remaining bicycles in Denver. Both kiddos also learned how to ride in early summer, so this was a delightful new family activity!
  • Enneagram — I’ve been curious about this instrument/lens for a long time, and finally got an opportunity to learn more about it thanks to the great folks at CultureSync. If you’re curious, I am an 8 — but, apparently, a “social” 8, which means that, at my best, I use my “challenger” nature to make the world better for all of us.
  • Became A Schoolteacher — Of course this isn’t actually true. Learning how to split my focus between my work duties and helping with homeschool was a huge and difficult stretch, of course, but even in a world of virtual learning, the real teachers still do all the heaviest lifting (and ALL of them deserve to make more money than I do).
  • #lovework — I haven’t talked about this too much yet, but expect that to change in 2021! Last year at this time, we had a good idea for what #lovework might be and a first-version app built on a third-party platform. This year, we have a tested and scalable program that was put to work inside Amazon, of all places, along with a new app we built from the ground up that will launch in January. I fully believe the pandemic accelerated and condensed about 3 years of our development roadmap into 6 months, and while I definitely don’t want to do that timeline again, wow, we accomplished a lot and I can’t wait for you to check it out! (Click here if you’d like to chat about it.)
  • Trademark — We officially received the trademark registration for #lovework® in August, which was (and is) very exciting! I’d never been through that process before… if you’re curious, it took almost a whole year to complete it.

Priorities/Intentions/Goals For 2021

  1. A little less fight, a little more flow — This is a fairly subjective “interior experience” goal. As I learn more about my Enneagram 8-ness, I realize I want to continually work on showing up in more loving and open ways, while also practicing a healthy integration of my “Challenger” nature, as that is an important part of who I am, too. In other words, while it seems to be part of my wiring to challenge the status quo, this coming year I also want to practice balancing the “fight” with a healthy amount of “going with the flow.”
  2. Start learning jazz piano — Some of you may know that I am a classically-trained pianist. But I have been wanting to learn how to play jazz piano for many years, and I think 2021 is the year to start! (I’m anticipating this will be a many-year process, which is why this year’s goal is simply to get started.) I’m curious if this goal might also help me with #1… there’s something about jazz improvisation that feels very related to what I’m talking about with that goal.
  3. Take a long vacation — Sometime this coming year, I need an extended period of time to relax on a beach. Full stop.
  4. Continue good workout habits — I’m arguably healthier than I’ve been in many years, due to finally finding a home workout routine I actually do. And though I will be very excited to get back to in-person yoga classes as soon as I can, I want to continue many of my good home workout habits as well.
  5. Build more relationships — Continuing the goal I had in 2020. However I can, I’ll be creating the space and time needed to build and deepen relationships with new and old friends, especially here in the Denver area.
  6. Orbit the entire Helios biz around #lovework — In my view, #lovework is the real-world materialization of something I set out to do about a decade ago: create an energizing way to scale organizational culture change that actually impacts a person’s day-to-day work. If you’ve ever attended a corporate workshop, training, retreat, or anything similar, you likely know they don’t do this. They often provide great ideas, but an event-based learning model doesn’t typically help ideas become new habits. We’ve built something entirely new — #lovework — and it will be the central tentpole of Helios moving forward. (Have I mentioned I’m excited to share this with you?)

Wow, you made it all the way to the end! As always, thanks for reading. I truly wish you all the best in 2021. ❤️

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Should We Abolish The Electoral College?


In some ways this article is different from what I usually write about.

But in many ways, it’s about the exact same stuff I always talk about.

If you’ve followed my work for any length of time, you know I’m obsessed with organizational systems. Typically, we’d probably use this phrase to talk about systems that are related to “organizations,” by which we mean “businesses.”

But I’d request we expand our thinking around that phrase.

You see, organizational systems are really just systems that help us organize. And at the “DNA” level, these kinds of systems are remarkably similar in functionality, no matter what their purpose is — organizational systems essentially make choices for us, many times without us being aware they are doing that.

So today, let’s talk about a remarkably peculiar organizational system…

It’s a system called the Electoral College.


Why I Wrote This

After the 2016 election, I decided to do some research on this uniquely-American thing called the Electoral College.

For everyone alive today, the Electoral College (“EC” in many places moving forward) has really only been truly relevant twice: in 2000 and again in 2016. So in most of the elections I’ve seen, I have — quite successfully I might add — simply pretended it didn’t exist.

This time though, in 2016, something felt different.

I knew I now needed to:

  1. Figure out what the Electoral College actually IS,
  2. Figure out why it was designed the way it was, and
  3. Figure out what I thought about it.

With another impending election on our doorstep, I thought perhaps my research could help others understand the EC better, too, so here you go…


What The Electoral College Is, And Why It Was Designed The Way It Was

Let’s start with a quick, and slightly simplified, version of how the EC came to be.

You’re probably aware that the Electoral College is the system the United States uses to choose a new President.

But you may not know that, as so many things do in American history, the story of why the EC was created starts with slavery.

Yes, really.

At the Constitutional Convention in 1787, our famed framers met in Philadelphia to do a number of things, including to determine how to elect an American President.

Some delegates, including James Madison, preferred a popular election of the President, but it was quickly determined that the southern states wouldn’t go for this as a huge part of their population were slaves that weren’t allowed to vote.

Something called the Three-Fifths Compromise plays into this, as well. This was basically a way to count slaves for the purposes of both state taxes and representation, and in which the framers settled on counting 3 out of every 5 slaves as people (again, yes, really). In practice, this gave states with slaves increased representation in the House Of Representatives and therefore increased representation in the Electoral College, as well. More on this big, and not-talked-about-enough, topic here.

So Madison and Alexander Hamilton (primarily) designed a different solution — one that utilized “electors” instead of a majority popular vote.

In The Federalist Papers #68, Hamilton described his take on the electors that would be chosen: “A small number of persons, selected by their fellow-citizens from the general mass, will be most likely to possess the information and discernment requisite to such complicated [tasks].”

These electors, once chosen, were intended to then independently deliberate, analyze, and choose the best candidate for the country.

While the design was clearly for electors to make autonomous decisions, states quickly figured out that if they pooled their electors to all pledge toward ONE candidate, it would put their chosen person in a much stronger running position.

Of course, the other states had to rapidly follow suit with this tactic to keep their candidates competitive.

Hamilton and Madison were violently opposed to this approach, saying that a pre-pledged winner-takes-all “general ticket” approach violates the very spirit of the Constitution. Hamilton specifically viewed this problem as a gross error, and even drafted an amendment to the Constitution in 1802, but it was never passed (obviously).

So, fast-forward 200+ years and we’re still utilizing an presidential electoral process that was:

  1. In many ways put in place because of slavery, and is also
  2. A system which the very people who designed it wanted desperately to reform when they saw how it was being abused in practice.


Other Initial Thoughts

The notion that the framers didn’t really trust the common voter is a bit contested — I’ve read arguments on both sides, though it feels to me like it’s slightly more true than not; there’s really no denying the “elitist” quality in Hamilton’s description of electors.

But even if we assume only the highest in positive intent in their design of elector selection, the concern of being able to properly disseminate information to the common voter, while a valid point then, isn’t relevant at all today. Getting information to every corner of the country is no longer a remotely difficult problem.

It’s also worth noting that today, all states but two (Nebraska and Maine) have adopted a winner-takes-all electoral system that has replaced analytical, deliberative, free-thinking electors with “potted plants” who simply vote the party line. And the Supreme Court just reinforced that they basically have to (as of July 2020).

(Side note: I can only imagine the rap battle that would ensue today were Hamilton still alive to see that this “violation of the spirit of the Constitution” is still in place over two centuries later.)


Are There Any Good Reasons For Keeping It?

The most interesting and viable arguments I’ve seen for keeping the EC intact revolve around statements like “we are a nation made up of states” and “the EC ensures that no one becomes President without the support of many states.”

I find this angle to be compelling at some level, but I think it’s more compelling to argue that we are a country made of individual citizens, and that every single person’s voice deserves to be heard.

The “state” logic, while somewhat interesting, elevates some kind of vague, conceptual “state identity” over the actual voices of the people who live in all parts of our country, and to me that seems fundamentally inappropriate.

Perhaps most importantly, there’s something inherently democratic and equitable about one person = one vote.

It also seems reasonable to say that state boundaries might not be as relevant today as perhaps they once were. Our similarities and differences don’t break cleanly along state lines — it’s more accurate to say that our most prominent divides happen between cities and rural, coasts and center, North and South, etc.

Most importantly, in a national election, shouldn’t it be such that ALL the voices in the nation, no matter their geographical location, have an equal say in who leads them?


What I Think About It

In short, the Electoral College needs to go away.

A primary reason it exists at all is because of slavery, which is just an embarrassment (to literally say the very least), and from the very beginning it wasn’t used as intended. And it’s never been fixed.

From what I can tell, the primary reason it still exists is inertia — and because in the vast majority of elections we’ve had, it has simply reinforced the results of the popular vote, thereby allowing it to remain mostly invisible. There have only been five (5!) instances since George Washington was elected in 1789 where the EC winner did not also win the popular vote: the two times mentioned at the beginning of this article (2000 and 2016) and three others that all happened in the 1800s: 1824, 1876, and 1888. (And 1824 was a fascinating election in a number of ways.)

Also, the only word I can use to describe the math of the EC is “horrendous.” With the EC, a candidate could theoretically win the U.S. Presidential office, arguably the most powerful single position in the world, with only ~22% of the popular vote.

Frankly, anything with this kind of stupidity baked into its arithmetic should not be involved in any kind of democracy — much less be a foundational rule in one of the most influential countries in the world.

Let’s stick with math for one more moment, because the EC itself is also pathetically unbalanced in the way it “represents” our people.

Let me give you an example: Wyoming is a state of approximately 586,000 people and it gets 3 electoral votes. California is a state of 39 million and it gets 55 electoral votes. If California were to get equal representation to what Wyoming voters get in the EC, California would have 199 electoral votes.

One doesn’t have to be a mathematician to see the problems here.

Next, let’s explore a few questions that always seem to come up with this topic…

Q: What about the people who don’t live in high-population states?

A: Yes, what about them? In a world without the EC, their vote would still count — unlike the votes of hundreds of thousands of people from heavily- populated areas whose votes are essentially worthless under the current model.

On a personal note, I grew up in town of 1300 people in seriously-rural South Dakota, and approximately 100% of my immediate and extended family lives in lower-population states.

Am I saying I don’t want the votes of all these people I love to count?

In case my rhetorical question isn’t clear, let me be: I am not saying that at all.

To all the wonderful people who live in lower-population parts of the country (my family and everyone else): I am simply saying that I want your vote to count as much as mine would if I still lived in Los Angeles.

No more, no less.

Q: Doesn’t the EC protect small states from big ones?

A: As mentioned above, our divide isn’t really about “states” as much as other things (like cities and rural), so this argument starts out as misleading, and it’s one that gets passed around a lot.

That said, even if we adjust the argument to talk about protecting “rural areas” from “big cities” (or one of the other more accurate labels), it still doesn’t hold up because in a democracy, one person’s voice should not be “worth more” than another’s, and this is what the EC does: it rewards or penalizes people simply because of where they were born or where they’ve chosen to live in the country.

States don’t vote. Land doesn’t vote. People do.

Q: But we’re a Republic, not a Democracy!

A: First, that’s not a question.

Second, this point is irrelevant to this topic, even though you’ll see it get associated. In a Republic, we elect people to represent us. But how are those people elected…? You got it: with one notable exception, via a popular vote.

Side note: we use a popular vote to elect Governors of our states… why should it not be the same for the President?

Q: The EC ensures the person we elect is “everyone’s President,” right?

A: This is another angle on the above questions: because less-populated states have a weighted-larger voice in the EC (reference the math above), presumably the EC helps to ensure that those states are “represented” in the election, and that those parts of the country feel “counted” in a Presidential choice.

But the problem is that the EC makes those areas unfairly OVER-represented while at the same time UNDER-representing areas with large populations.

So we can end up with literally hundreds of thousands of people — or in the case of 2016, 2.9 million people — whose votes didn’t actually count simply because they live where they live.

That’s the opposite of a candidate being “everyone’s President.”

Q: Without the EC, wouldn’t candidates spend all their time campaigning in major population centers?

A: Maybe…? But first of all, focusing campaign efforts on specific areas isn’t any different from what candidates do now in so-called “swing states.”

And while we’re on this topic, how is it somehow more democratic to spend extra time in areas with less people?

Secondly — and I mean this in all sincerity — is it that much of a big deal if a candidate is campaigning physically nearby? Are we worried that people won’t get enough information to make an informed choice? Seems to me we’re all drowning in more information than we can handle.

And, as we now know more than ever thanks to the pandemic, there are a LOT of things we can do virtually that we didn’t think were even possible a few months ago. I suspect virtual gatherings will be a much bigger player in all things political moving forward.

Q: Doesn’t the Electoral College produce more certainty of results?

A: Even if it could, at what cost? What we know it does is produce results that are potentially wildly out-of-step with the majority vote of our population.

It’s worth noting that an abolition of the EC would require us to thoroughly overhaul our voting systems and processes, but in my view this seems like a far more appropriate course of action (and is frankly necessary even with the EC as-is).

Furthermore, making the Presidential election based on the popular vote would likely ignite all sorts of creative innovation at the state level to encouraging all its citizens to participate and vote, which would be a tremendously good thing.


So What Do We Do?

Let’s say you buy my arguments and agree that the EC needs to go.

To change the rules themselves would require a Constitutional amendment, which is supremely difficult. As much as I’d love to see this happen, it doesn’t seem incredibly likely.

However, there is another option that seems slightly more reasonable — something called the National Popular Vote Interstate Compact. This proposal shifts the process to align each state’s electoral votes to whomever wins the popular vote, and it’s already almost 73% of the way to becoming successful. (If you’re interested, there’s a super easy way to send a note to your local legislators right on the front page of their site.) I would highly recommend learning more about this effort.

Most importantly, I hope you’ll help spread the word about what the Electoral College is, why it works the way it does, and why it needs to go away.

All organizational systems should be evaluated on their justice, equity, and ability to expand toward more inclusivity. The Electoral College fails the test, and it’s time for us to do something new.

“Never doubt that a small group of thoughtful, committed citizens can change the world. Indeed, it is the only thing that ever has.” — Margaret Mead


P.S. While We’re On It, A Related Topic…

Forgoodnesssake, why do we still vote on a Tuesday that’s not a federal holiday? I mean, I know technically WHY (ahem, voter suppression, ahem), but it’s really just absurd. If you want more on the why, here’s a non-kid-friendly video that explains it. Can we fix this, too, please?

P.P.S. A Couple References

As you’d suspect, there are a LOT of articles and videos online about this topic, but this video might be my favorite so far, plus a pull quote: “You know what they call the ‘popular vote’ in the rest of the world? The vote. Alexander Hamilton would be horrified to see the perversion that his Electoral College has become.” This interview is also excellent (and is referenced several times above).

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WorkRev Episode 4: The Future Isn’t What We Think It Is.

Leadership, Legacy, Life

Today I want to talk about something that’s on many people’s minds right now…

The future.

We’re kind of obsessed with “what comes next” — right now the conversation is mostly in relation to the COVID pandemic — but this is always a question we humans have, isn’t it?

What comes next?

Well today I want to talk a little about this question, because the future actually isn’t what we think it is.

I think is important to note that questions like “what comes next?” actually betray a fundamental misunderstanding about the future itself.

When we say things like “what comes next” — or phrases like “the new normal,” which I’m hearing a lot right now — in a subtle way we are taking ourselves OUT of the equation.

We’re making ourselves observers instead of participants.

These questions talk about the future as if it were something that happens TO us, but this isn’t how it works.

It’s easy to think about “the future” as some kind of destination point on a map — fixed and certain, and we all just kind of hurtle towards it.

But the future isn’t a formed, defined ANYTHING — it’s pure unbridled possibility, and what it will actually look and feel like is something that’s being actively co-authored by all of US, right now.

The choices each of us make in this moment — and every moment — create a different future than the one that existed a second before.

When I make the choice to exercise.

When you make the choice to go out of your way to help someone, you can visit following online pharmacy (wemailmed.com)

When we all choose to stay home to protect the most vulnerable.

We change the future.

So let’s be thoughtful when we use phrases like the “what comes next” or  “new normal” — because we are actively shaping what those things will be with our words and our choices.

The “new normal” isn’t a place we’re going to “arrive at.” It’s something we get to BUILD.

Instead, let’s think about it as what what one of my friends called a “next normal” — something we all get to create together, right now.

What does happen is that humans naturally move towards our picture of the future — so let’s get clear on the next normal we WANT, and build that.

See you next time.


View the Show Notes HERE

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