My Work as an Octopus: Generalist Income From Multiple Interests

Funding a multi-hyphenate, polymathic, generalist life of freedom that aligns with who you are.

In my last post, I discussed how generalists, polymaths, Jacks/Jills of all trades, renaissance people, and multi-passionate hyphenates can embrace an interesting and fulfilling Octopus Life. If you haven’t read that post, please do so now, as it will help this post make more sense.

In this edition we’ll discuss a challenge for Octopus People: In this age of specialist employment, how can we make Octopus Money that funds an Octopus Life?

First let’s talk about some pitfalls of putting your trust in “specialist” work.

In traditional specialist employment, you are hired to do a certain thing, or perhaps a narrow set of things, related to a specific need at a company. Accountants do the books. Factory assemblers attach the steering wheel on the car. There may be some variety in your work, but for the most part your tasks are confined to a limited set of responsibilities.

For Octopus People, there are multiple problems with this type of work:

1. It gets boring doing the same thing over and over.

2. It does not allow us to meander and be curious.

3. We are discouraged from trying, or even inquiring about other kinds of work, even within the same company.

4. We must follow the “Standard Operating Procedure”. Creative deviations or alternative methods are discouraged.

5. The longer you do specialist work, the harder it becomes to switch to another career.

6. Specialization is a potential driver for a mid-life crisis, in which you have become pigeon-holed into something that you are either no longer interested in, or never were interested in, and now you feel trapped.

7. All your income is derived from one job. What happens if the company struggles and lays you off? All of a sudden your single source of income evaporates. You must now scramble to find another single source income job, and the dependency cycle continues.

In a nutshell, highly specialized careers can be soul killing for Octopus People.

Many books and coaches will tell you it’s because you have not found your “one thing” and if you could just figure that out, you would enjoy life. Just fill out this Ikigai diagram or do the Strengths Finder survey, then find an occupation to match! It’s easy!

There is an entire industry dedicated to this approach, and it does not appear to have a great track record of success for anyone, but especially for Octopus People. It’s too restrictive, forcing you into a small box, and paralyzes you because you cannot figure out your one thing. You are made to feel bad and wrong, as if having multiple “things” is some kind of curse.

Is there another way to think about this?

If a specialized career is a slow death to Octopus People, how might Octopus Work look? Here’s a diagram that illustrates the central concept:

Octopus Work vs Specialist Work

Let’s examine these one at a time:

1. Specialist: Does only 1 narrow job.

2. Side Gig: Does 1 narrow job but tacks on a more fulfilling side gig.

3. Freelance: Does many jobs all related to a specialist competency.

4. Octopus: Does up to 8 things that may or not be related.

Looking at this diagram you may feel a bit of skepticism. We understand the first 3, but is Octopus Work really feasible? Decades of reinforced learning tell us that only the first 3 are actual occupations, and they are listed here in increasing order of risk. The safest choice is a specialist job, followed by a specialist job with a side gig, followed by freelancing, and there are no actual jobs for #4.

Is that true? Is anyone actually doing this?

There are both people and companies doing this right now, we just don’t call it Octopus Work. For example, 3M, GE, and Danaher are examples of Octopus corporations. They have multiple products in a wide variety of unrelated sectors.

Angel Investors put money into a wide variety of startups, in diverse arenas, and may act as an advisor to those startups.

Individual Octopuses within a certain creative realm, like Virgil Abloh or Pharrell, do work in design, fashion, music, and entertainment.

I have to admit there aren’t many true Octopus People in wider public view. My theory is that’s because specialism currently dominates the world of work. But in private, I believe there are way more Octopus People than we realize. Similar to the “hidden” introverts in an extroverted world, I think there is a huge population of Octopus People hidden in a specialist world.

But times are changing!

There are trends happening right now that make Octopus Work more feasible than ever…

1. The rise of contract, freelance, and fractional work: allows you to work on more than one “job” at a time.

2. Technology advancements: computers, high speed internet, apps, and creator tools provide options to generate income in a wide variety of ways.

3. Geographic flexibility: you have more freedom than ever to live and work in another city or country, giving access to multiple economies.

4. Global marketplace: you can sell digital or even physical goods in many countries besides your own.

What can an Octopus person do to capitalize on these trends?

The “tentacles” of Octopus People vary widely, so I cannot prescribe what you as an individual should do. But I will layout my tentacle framework and how I might activate tentacles to make a living.

Let’s say you have 8 tentacles. Meaning 8 different things you like to do. 8 may feel like a lot, but I think it’s actually better than saying 3 or some other achievable number. 8 makes you stretch your imagination, it encourages you to lean in to your true Octopus nature rather than artificially restrict yourself.

So here’s the exercise to try…

Write down 8 things you want your work to be about. Do not order them by priority, as the order is unimportant. Unlike forcing yourself to pick 1 thing, which is nearly impossible for Octopus People, listing at least a few should come quickly and easily. You know what your main interests are. It could be business, music, sport, art, children, health, fitness, etc., or any variation of those themes.

To do this exercise, copy/paste the following into any text based software:

1. Tentacle [ $ & :) ] Monetization

2. Tentacle [ $ & :) ] Monetization

3. Tentacle [ $ & :) ] Monetization

4. Tentacle [ $ & :) ] Monetization

5. Tentacle [ $ & :) ] Monetization

6. Tentacle [ $ & :) ] Monetization

7. Tentacle [ $ & :) ] Monetization

8. Tentacle [ $ & :) ] Monetization

Or here’s a downloadable printable PDF if you like writing with a pen:

Octopus Tentacle Monetization List

Here is my Tentacle list as an example:

1. Creativity

2. Design

3. Tennis

4. Branding

5. Film

6. Motivation

7. Sarcasm/satirical humor

8. Sane social media

Take a moment to write your Tentacles down. As you can see from my list, these are not particularly specific. They are not jobs. Do not put jobs down. They are more like interest areas, passion topics, or thematic zones of affinity. You may have done something related to these themes in the past, either as work or hobbies, or they can be things you have not done but want integrated into your future.

Making money vs having fun

Do you have your 8 tentacles? Good. Next we’ll tag these items based on whether they are monetizable or not.

Your 8 things don’t have to make equal amounts of money. Just for discussion sake and easy math, let’s say you would like to earn $80,000 a year (or whatever multiple of 8 makes a sensible wage in your country). You don’t have to make each tentacle earn exactly $10,000. It could be that 2 of your tentacles earns all $80,000 and the others earn nothing. Or if you’re an entrepreneurial Octopus, maybe you want all 8 to make money.

The only thing you can’t say is, “none of my 8 things will make money”. Then you will be broke and have a very stressful life (unless you are independently wealthy and don’t need money). The key point is to decide which tentacles will be money earning and which are “meandering fun” tentacles that let you just enjoy life.

Separating tentacles this way gives you the freedom to say to yourself, “Tentacle #7 is just for fun, it’s not intended to make money”. It can relieve some pressure to monetize everything you do, and remind yourself to enjoy your life. Remember Octopus People have diverse interests, and some may be inherently non-commercial.

In the template, I have put 3 “Tags” next to each tentacle:

$ = this tentacle can make money

& = this tentacle can make money AND would be particularly fun

:) = this tentacle doesn’t have to make money and is solely for fun

Use this key to score your tentacles. Here’s how I score mine:

1. Creativity [ & ]

2. Design [ & ]

3. Tennis [ :) ]

4. Branding [ $ ]

5. Film [ :) ]

6. Motivation [ & ]

7. Sarcasm/satirical humor [ :) ]

8. Sane social media [ & ]

Show me the money!

Next we will brainstorm ways to turn your money making tentacles into some type of commercial activity. Even for the items that are just for fun, it’s worth trying to come up with an income producing angle. You may be surprised that you actually have an idea for turning fun into money.

If you are not a business minded person you may struggle with this, but I would encourage you to dream a bit, and utilize whatever you’ve seen people do out in the world as inspiration. Nowadays money can be made from almost any endeavor.

It’s ok if you haven’t figured a monetization path for every item out, just put “I don’t know” next to those.

Here is my complete list with income generating ideas:

1. Creativity [ & ] I don’t know, maybe start a creative agency

2. Design [ & ] design a series of T-shirts to sell

3. Tennis [ :) ] I don’t know

4. Branding [ $ ] do brand strategy consulting, sell downloadable templates teaching people how to do branding, or make a community for people who like branding

5. Film [ :) ] I don’t know

6. Motivation [ & ] create a motivational poster to sell, or start a meditation podcast

7. Sarcasm/satirical humor [ :) ] create a satirical newsletter like Andy Borowitz’s New Yorker articles

8. Sane social media [ & ] I don’t know, maybe start a social media app

As a reminder:

• You don’t need 8 things, it can be less than 8.

• Each item doesn’t have to make money, some can be for fun.

• It’s ok not to know how to monetize some tentacles.

You don’t have to “finish” your list right now.

Part of being an Octopus is to meander, giving your tentacles freedom to explore, and feel out their surroundings. Unlike “find your one thing” exercises, this is intended to be a fluid list. Specialist exercises force you to complete the process because if you have not figured out your “one thing”, you have nothing.

Don’t put pressure on yourself to complete it to perfection. You’re being exposed to this concept for the first time, so cut yourself some slack. You may not have ever given yourself permission to think in such ways, so it may take some time to uncover what you truly want to do. Octopus Work is flexible, fluid, and gives your life freedom to meander. But I would encourage you to also write down the first things that come to mind. Often our dream endeavors are just under the surface, waiting to be brought into the light.

Well that’s it for today, I hope this exercise was thought provoking. In a future post I’ll talk about how I’m activating my tentacles, hopefully to provide some ideas and inspiration for how you might do the same.

If you think of yourself as an Octopus Person, I hope you feel seen, slightly less alone, and maybe excited that instead of fighting your Octopus nature, you might be able to activate it, and make it a superpower.

If you want to discuss this with other like-minded Octopus People, copy/paste your tentacle list into the comments, I would love to see what you came up with! Remember it doesn’t have to be “finished”, you can post a draft and get feedback and ideas from others.

Until next time,

Dave