The Multi-Path Career


* From executives to individual contributors, we all make one career bet at a time.

* This is poor “portfolio theory” (to use a phrase from investing), meaning that this is not a balanced “portfolio” of diverse bets. It’s a career “portfolio” of extremely concentrated bets.

* You can win big this way, but admittedly, most will not.

* With current technology, remote work-styles, and the catalyst of Covid-19, the future will allow for (and incentivize) multiple career bets at the same time; albeit perhaps at different stages of each path — like an architect with three parallel projects (one in concepting, one in planning, and one in construction).

* With the possibility, the incentives, and the social norms in place, it will become the ideal work-style for executives over the next decade… From “freelancing” as a performance marketer to “C-lancing” as a CMO of three companies at the same time.

* This isn’t for everybody, but for the adventurous minority, a new wave of working style will emerge in the coming years.

I’m sitting on an inflatable mattress, working from an iPad, listening to the world’s largest music library with Apple music (and my in-ear headphones).

I’m going over my “to-do” list for today with my three main projects — angel investing (I’m about seven years into this “project” of investing), Magic Mind (magicmind.co, a drink I created after writing a book on natural ingredients for productivity enhancement last year), and podcasting (I host a new-ish podcast called “Below The Line”).

And I’ll manage all of these projects today from my iPad, on an inflatable mattress, listening to the world’s music with my handy headphones in.

On a monthly basis, my time is spent coordinating with dozens of founders, executives, consultants, contractors, and freelancers, spanning topics from podcast newsletters, helping founders wind their company down in a healthy way, and coordinating the sale of a matcha/nootropic tea in London. And it’s all from my iPad on an air mattress.

A lot has changed in the last few years (for example, my iPad is significantly faster than my Apple laptop — Can you tell I really dig the iPad?).

As I reflect on the (surprising) fluidity in which I’m able to balance these three very different projects, I continue to find myself thinking about how the year 2020 is vastly different than the year 2000. It is the combination of technology and work-style that seems to make these possible and somewhat seamless.

My next thought then turns to “why aren’t we all talking about how different our working lives can be in the 2020?” The answer seems to be that most of us still think we’re basically living in the same world as 20 years ago. In other words, technologically, we live in 2020 — but our psychology is very much stuck in the 20th century. We might remark on what different technology we have (a super computer in 3Bn pockets), but it hasn’t infiltrated what it can truly allow us to do in terms of our careers.

Side-bar: I remember reading in Jonathan Safron Foer’s book “Eating Animals” that despite today’s access to global supply chains and ingredients, the average Americans still eats roughly the same diet as we did 100 years ago, and the average American consumes only .25% of the world’s available ingredients in their dishes.

It seems that “possibilities” + “potential” can shift rather quickly, but our collective psychology and norms take much longer to catch up (read more about my views on “Community vs Truth” here). But add the fear of death into the equation… And it tends to be a powerful catalyst; examples being face-masks, social distancing, and just about every company going remote in a four-week span.

You could maybe make the case that our collective psychology is still stuck in the 15th century (zero-sum world, Earth is at the center of the universe, the world is made of “solid” things, etc), but let’s be generous and say that most of our cultural psychology is only stuck in the 20th century.

And let’s focus that on the 20th century invention of a “career”. The 20th century invention of a “career” was more or less defined as one path per life, one job per life (laborer on the manufacturing line at Coca-Cola, farmer in Idaho, advertising person on Madison Ave.).

Like a road trip with one destination in mind, with time spent finding the one highway to get you there.

That was the goal; to get to that destination where you could rest and relax. Maybe it was a goal to earn a pension after your 30 years on the General Motors manufacturing floor or to get tenure as a professor. One destination per person. One path that you should settle on by your early 30’s.

In the last few years, the norm has changed drastically, but it’s still a legacy of last century. Now it is one path “at a time” and one job “at a time.” Changing it up as fleets of fancy (or destabilizing forces like a layoff) take you in a new direction every few years. But it’s still one path and one job at a time, and hopefully settling into a groove by your 40’s. It’s still a road trip, but maybe it’s to Tahoe for a little while and then to Los Angeles after that and then settling in down in Sedona.

Over the last few years, you could contrast this single-path-at-a-time career track with your freelancer friend, your friend that is contracting for two large companies, the gig worker, the person that owns the agency, or the venture investor that is simultaneously on 10 boards of 10 different companies. The term multi-tasking doesn’t quite fit here. Everyone multi-tasks throughout the day. These people were multi-pathing.

But what if a CEO could multi-path? 

Or a CFO? 

Or a head of marketing? 

No, no, no. It’s got to be one company at a time, one job at a time. Right? Only investors can do that.

People need to be judged by the time they’re in the office, and there’s no such thing as remote work. Right?

People need to learn and get to know their team-mates over dinners and happy hours and serendipitous conversations at the office to learn that they have things in common. Deeper connection achieved after 6 months!

People need to show their grit and resourcefulness in-person; there’s no such thing as dashboards showing key metrics in real time from your pocket’s supercomputer.

Or git-tracking to see which engineer is writing what code. 

Or the ability for an executive to present remotely and asynchronously (Loom presentations are my new favorite media) from their own, personal office — like their attic, kitchen or back-house. Right?

To get input on this presentation you’re working on, you need to be able to walk over to Jeff or Divya and ask them in person about it. There’s no such thing as email or google docs. And you can only be on one team and at one place at a time.


Maybe not.

I once heard an investor say that “the best board members can’t help a company achieve greatness. The best that the best can do is help them avoid the various fatal mistakes startups make.” They are essentially experienced editors, qualifying what *not* to do.

Side-bar: This has evolutionary similarities — primates, for example, have more inhibitory neurons than any other animal. And humans have vastly more inhibitory neurons than any other primate. It seems evolution hasn’t just been a process driven by what a species can adaptably ‘do’ but also shaped by what a species is capable of choosing ‘not’ to do.

My estimation is that the fundamental role of an executive is similar — editing priorities and removing what the company should not be doing is their fundamental function over anything else. It’s perceived as choosing what to do, but like a skilled surgeon, it’s actually much more about their expertise on what not to do that helps them focus on the few important things that they should do. Focus, like simplicity, after all is the ultimate exercise of remotion.

One layer deeper than that, you have individual contributors — where most of us were in the first ten years of our careers, learning by doing, committing lessons to emotional, neurological pathways we will go on to remember for our entire careers. Learning the why’s behind the what’s and the how’s. Learning the why’s behind doing this and the why’s behind not doing that. It’s here in our careers that we are doing most of the physical labor.

This isn’t too dissimilar to constructing a building. You have an owner (board member), an architect (C-Suite executive), a general contractor (a sub-layer of executive), and the construction worker (individual contributor). Like owners of buildings, in knowledge work and company-building, it’s normal for board members to contribute to multiple companies.

But in 2020, the executives, if they are the “architects” in this analogy, do not have the social convention to work on multiple projects at a time. Why is this the case?

My hunch is that this “norm” is more geographical than it is structural or beneficial. In other words, the architect does most of his or her work at a desk in an office, away from the project itself. Checking in often, of course, but much of the work happens “off-site” out of necessity. And this has been the case for decades. This “off-site” physical detachment opened up the freedom for first-principles, fundamental, thoughtful answers to the question: “Could I, as an architect, work on multiple projects at once? Perhaps at different stages? That require different amounts of my attention?”

The answer, it turns out, was not only “yes” but that it was actually professionally prudent to do so. To have multiple clients and bets. The geographic, spatial distance created this question… and smart architects created the precedent that became the convention that has now become the obvious answer (yes).

With the world being thrown into a distributed work-style with Covid-19 two months ago, where every company and executive in the world became more remote than ever before in a 4 week span (!)… My hunch is that the age of remote work will be a catalyst in introducing this freedom of asking this question and the smart executives creating the precedent that will then become the norm. In other words, the catalyst to asking this question and having thoughtful, fundamental answers in the separation of your physical work from other’s physical work.

I use the term catalyst because it’s already happening in pockets. And I think it’s about to go mainstream in the next decade.

What are some of the pockets where fractional leadership has worked well? Warren Buffett and Charlie Munger’s Berkshire Hathaway has been running multiple businesses for five decades (with a combined 60 businesses and over 400,000 employees), all with a 25-person team in Omaha, Nebraska. Warren Buffett has commented on the compounding benefits of wearing multiple hats when stating “I’m a better investor because I’m a businessman and a better businessman because I’m an investor.” 

But what about operational executives? Steve Jobs famously ran Pixar and Apple at the same time. Exhausting as it might have been, both were undoubtedly massively successful with him at the helm, and you have real proof-points of the previous “single-path” executives at each that didn’t have nearly the same impact before he arrived. 

Elon Musk famously runs multiple companies as well (Tesla, SpaceX, and six others), and it would be hard to make a strong case that someone else could’ve done a better job — no matter how much “single-company” focus that person would bring. Same goes for Jack Dorsey or Jeff Bezos’ multiple executive roles.

Side-bar: Even Isaac Newton famously worked (in parallel) on his universal laws of motion at the same time that he concentrated equal hours in a much less fruitful career, alchemy. Even his towering genius did not know which field would reap the most rewards, and we should all be thankful he made two bets.

But is this just for billionaires? Tiny Capital out of Victoria, Canada, is a 10-person team with 25 companies under their ownership and guidance. Multi-path pioneers? Yes. Billionaires? No.

Besides track record and notoriety, what do all of these have in common? They certainly each had the insight that this can be done. And secondly, billionaire-status aside, they each admittedly had the immense resources to be the canaries in the coal-mine.

50 years ago or even 20 years ago, this was very expensive to do. To connect, acquire context, communicate & meet, own the tools/machines/software to operate as an executive, and have the deep executive experience and social capital *all* added up to only a very select few being able to choose this individual (or organizational) operating model. 

In other words, it was so expensive and contrary to typical conventions, that it required immense financial and social capital to take this route.

It was kind of like starting a technology business back then. 

Risky, not because of the potential to fail, but because failure was so expensive. In other words, it was risky; kind of like jumping over a 10-foot-wide rushing stream is risky. But make it a 10 inch puddle, and it’s not so risky anymore. Starting a software company in 1990 was at a minimum a $30M endeavor, entrusted to only to the executives you had personal experience of working alongside.

Today, you can start, test, fail, and fall flat on your face in your pajamas with a Shopify store for pet furniture with just a few thousand bucks (funny thing about this example here; from the co-founder of Tiny Capital himself). Today, you can start, test, fail, and fall flat on your face… and your boss never needs to know!

What has happened to the operational costs of running an organization as an executive in the last two decades?

* Connecting with talented people (LinkedIn, email list-serves, online social networks) is a fraction of the cost of what it was before. 

* Communicating with team-members (Zoom, email, Loom, G-Suite, Slack, text message) is a fraction of the cost.

* Building context (Google docs and spreadsheets, immediacy of global video calls, Loom screen-share), especially for good communicators, is a fraction of the cost. Physical interactions are rarely needed. 

* The software to create anything from a podcast (your own “radio show”) to an industry newsletter communicating your expertise (your own “newspaper”) to building instant, globally distributed applications to professional video editing.. you name it, and it’s a few hundred bucks.

Add all of these up, and you have a fraction (of a fraction) of what it used to cost to operate a business. Add in remote-work, and you have the chance to do it in multiple ways at the same time.

If you follow the trend-line, and if you give it 10 years, the 10-foot-wide stream is becoming a 10-inch puddle.

Slowly but surely, the fractions of fractions of the cost + the separation of your physical labor from your co-workers will lead to the question: “Could I do this for multiple businesses at the same time?”… and that question will lead to some more pioneering leaders answering it for themselves, providing the social precedent of “my friend does this” instead of “Elon Musk does this.” Personally-connected-precedents grow into social norms. 10-inch puddles represent little-to-no-risk… and before you know it, people are trying it out for themselves, diversifying career bets, and showing us the way.

This has been fun to think through — but speaking of fractional career-paths, I really should hit command-tab on the old iPad and get back to my day job(s).


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