Launching Octopus Project 1: Brand Strategy Consultancy

My Octopus journey to a portfolio career officially begins.

Over the past couple months I’ve been interacting with people around the growing interest in generalism/polymathy. It has helped me shape my views on the subject and informed the creation of my “Octopus Life” construct.

While I still have more to explore, I am ready to turn thoughts into action and want to share some of my plans to build an Octopus style “portfolio career”.

In a nutshell, I am planning to make a living working up to 8 different “jobs”. I want to be clear these are not 8 full time, 40 hour a week jobs, so I’m not talking about overemployment. I’m not talking about 8 jobs that each take up exactly 1/8th of my time. I’m also not deploying a single skill across 8 different industries, like a freelance graphic designer might do, or holding 8 different rental properties as a real estate investor. I’m literally talking about up to 8 completely different ways to earn a living.

Why this oddly restrictive and difficult criteria? I’m trying to prove a theory, which is that people with polymathic abilities are actually good at multiple disparate things, and I want to demonstrate that these skills can be put to marketable use in service of a portfolio career.

Why apply this theory to jobs? Why not just have fun learning 8 musical instruments, or playing 8 different sports?

Work is the primary pre-occupation of our lifetimes. Work is also a source of frustration, constriction, and dissatisfaction for polymaths and generalists, so I want to prove that an “Octopus” type person can craft a new way of working outside a traditionally restrictive specialist box, that is more fully aligned to the fullness of who they are.

I aim to inform and inspire 4 groups of people with this project:

1. Myself: I want this chapter of my career to be marked by curiosity, creativity, and fun, and I want to prove to myself that I can accomplish something unreasonably difficult.

2. Polymaths, generalists, portfolio careerists, etc. Amongst this community we often speak about how our various interests and skills make us better at certain tasks. But in my cursory exploration, much of this talk seems to dwell in the realm of theory more than practice. I want to show others that a career that makes full use of all “octopus tentacles” is possible, and perhaps inspire others to explore how they might do the same.

3. Employers/Employees: In the “Future of Work”, the polymath/generalist community posits that we will become an increasingly valuable asset in an uncertain AI world full of wicked problems, due to our innate curiosity, knowledge across disparate fields, problem solving ability, and innovation. But stating that in a cover letter can ring hollow if a hiring manager cannot see examples of people actually demonstrating these skills in real-world endeavor. With this project I hope to be a “case study” of what a polymathic employee is capable of if allowed to fully deploy their faculties, and perhaps help increase confidence in hiring such a person. I will share learnings, pitfalls, and ways of communicating the benefits of these skills so that my fellow Octopus job seekers might be able to better position themselves and convincingly articulate their own unique abilities to prospective employers. If corporations are ever to create roles for us, they need to understand the value in what we have to offer.

4. Academia: To my academic friends who enjoy taking a long term view imagining the future of work, while simultaneously teaching current students how to build polymathic skills for the near term, I hope to provide a “test case” for your theories and ideas on what such a future worker might look like. While an N=1 does not prove any academic hypotheses, I hope to show an example to young people that such a way of thinking and working is possible, and might even be necessary in the future. In no way do I think of this project as any kind of “gold standard” to follow, but if I find myself referred to in a class someday as an interesting person to look at, I will be more than happy.

We need more everyday examples of a polymathic way of being

Polymaths/generalists like to point to exceptional individuals, such as Leonardo da Vinci, as prime demonstrations of what can happen when such a person deploys the full breadth of their abilities. But in the same way that we ask professional athletes or ultra-wealthy individuals what their secrets to success are, I find the use of exceptional examples limited in true transformative power, in the sense that the accomplishments of these individuals are extremely difficult to replicate, even if the advice they give is followed.

So where are the “everyday” polymaths? The modern examples of normal people living and thriving occupationally in this way? What can a non-genius accomplish in this realm? I am not an exceptional individual. I will likely not be written about in any history books. I failed calculus in college. I have accomplished what I consider a moderately successful career thus far. I realize this is all relative, but if someone like me, with an only slightly above average occupational profile, can do something interesting in this realm, it might help other everyday people believe they can do it too, and see a practical path to doing so.

I intend to smart small. These projects will not solve climate change or prevent pandemics. I’m a big fan of small bets, quick wins, and rapid iterative learning. I do have longer term conceptual aspirations to join forces with other polymaths to tackle bigger problems, for example in some kind of Octopus think tank, but if I cannot solve even small problems, how can I solve problems at global scale? I envision step-by-step increases in complexity as I proceed.

So today I am officially starting “Octopus Project 1”. I’ve already soft-launched this project, but I want to begin this narrative from the very beginning, so people can follow along, and also to avoid the “You were already successful before you started!” criticisms.

What is Octopus Project 1?

During my sabbatical last year I opened a brand strategy consultancy. Speaking frankly, I opened it too early, mostly out of fear of the gap in my resume, coupled with the fear of not having any income. I’ve done a handful of interesting projects over the past year or so, for example to reposition a environmentally friendly candle line, help a former Ritz-Carlton project manager market her book, and right now I’m rebranding a guitar effects pedal company. In true Octopus fashion, I’ve thoroughly enjoyed the variety of work, none of which is related to my previous career in diagnostic medical device marketing.

So I am officially re-launching this endeavor as Octopus Project 1. It is an obvious choice, as I have built up considerable specialist skill in branding and marketing over a 20 year career. If anyone reading this wants to create an Octopus-style portfolio career, I would strongly encourage you to start with whatever deployable skill you already have as the foundation for your portfolio. Seasoned workers should have multiple options to draw from.

I do appreciate the irony that what I’m doing now is only made possible by decades of specialist work, so I recognize that this endeavor does not start from scratch. If you are a younger person finding what I’m proposing appealing but struggling to think about what marketable skill you might have, I admit this might be harder for you. But on the flip side I like to think that everyone, even young people, have some skill in something, and many young people start companies or side gigs with very little experience, a deficit that can often be overcome with enthusiasm and ability to quickly learn on the job. Young people may also wish to think of the Octopus concept as an exploratory exercise to discover one’s areas of interest and future potential. Imagine an adolescent octopus in the ocean, exploring its surroundings, using its tentacles to touch coral, find food, and understand its world. Mistakes might be made, but this is a necessary process of learning and maturation.

The bottom line lesson with Octopus Project 1 is to consider what arrow(s) you already have in your quiver that you can put to immediate use as the first job of your portfolio career. It should be the easiest quick win, and from there, you can add additional tentacles to the mix.

Future Roadmap

I already have Octopus Project 2 in the works, it is an unusual kind of calendar poster that I have designed, which I will probably sell via Kickstarter in October. That project is more of a “fun” project, and something that I’ve been sitting on for a while, and just not had the inclination or courage to release to the world.

Octopus Project 3 is to become a first time author, writing about my Octopus journey in a book, followed possibly by more publications on branding and marketing.

Octopus Project 4 is still fuzzy, but revolves around forming some kind of Octopus innovation agency/think tank comprised of other generalists/polymaths, who wish to deploy more of their abilities upon real world, paying projects.

So here’s Octopus Plan version 1 as it stands today:

I hope you find this experiment interesting, and would love to hear your feedback, critiques, advice, and questions.

Thanks for spending some time out of your busy day to read this.

Until next time,

Dave