My Octopus Portfolio Career Diversification Strategy

How I'll select up to 8 jobs for my Octopus career

If you’re new here I’m running an occupational experiment to make a living as an Octopus aka a generalist, by doing up to 8 different jobs, aka a portfolio career. In this post I will explain my guardrails for selecting what type of work to do, how I’ll allocate my time, and expected income percentages for the 8 “tentacles”. This post is inspired by a question from Rick Foerster, who asked how I’m deciding what should be in the portfolio.

Sequential or Simultaneous Tentacles?

The first strategy decision I needed to make is whether to pursue each tentacle sequentially or simultaneously.

• Sequential means working on one tentacle, finishing it, then moving to tentacle 2, finishing it, then moving to tentacle 3, etc.

• Simultaneous means jumping around between all 8 tentacles at the same time.

Depending on what kind of Octopus person you are, you may favor one approach over the other. Both are valid if you’re trying to do a portfolio career, but I’m going with Simultaneous, as that’s just how my mind thinks and how I like to work.

But isn’t the simultaneous approach the much maligned “multi-tasking”? Isn’t context switching inefficient?

If you actually delve into the research on the inefficiencies of multi-tasking, you will find that nearly all of the studies are done on simple tasks like adding/subtracting numbers, naming colors, typing out emails, and classifying geometric objects. Think about it for a second. If you wanted to devise a study on multi-tasking, how would you do it? You’d get participants in a room and ask 2 groups of people to do some rote task. You’d interrupt group 1 and let group 2 do the task uninterrupted. By design these tasks have to be simple, as it is quite complicated and ironically, inefficient, to study humans doing higher order, strategic knowledge work, creative activity, or in our case, multiple entrepreneurial endeavors. For polymaths, all these activities actually benefit from context switching.

Tentacle Selection/Allocation Strategy

Here are my 8 rules to decide what to work on, how much time I spend on them, and how much money I expect to make from each tentacle:

1. A tentacle has to be something I’m capable of doing, or learning how to do in short order. In other words, I will not have a tentacle called “solve climate change” or “build a rocket”, as I have little expertise in these areas.

2. Tentacles will have a mix of active and passive income. Since it is physically impossible to work eight full time jobs, some tentacles must be passive. Active income is trading time for money, for example consulting. Passive income is money while I sleep, for example selling goods online.

3. No two tentacles will be in the same industry or market sector. The point of this experiment is to show that I can utilize my generalist abilities to extract revenue from disparate markets.

4. No two tentacles will be the same kind of job. For example, I cannot do graphic design work for a car company, then do graphic design work for a healthcare company. Those are the same occupation, so would only count as a single tentacle.

5. No tentacle shall generate 100% of the income. This is too risky, if I lose this tentacle, I lose all my income. This is essentially a traditional full time job, defeating the purpose of the Octopus experiment.

6. At least one tentacle should generate 0% of the income. This is the “fun” tentacle, which has no intention of making money. Why include it if it won’t generate any revenue? Because it reminds me that this experiment should also be fun, and fun activities don’t always need to make money.

7. The 8 tentacles do not need to generate equal income. It will be extremely difficult to have each tentacle create exactly the same amount of money.

8. I can drop a tentacle at any time for any reason. Octopuses can lose a tentacle and regenerate a new one. I will do the same.

Spreading My Bets

Another benefit of trying 8 different things is that it gives me many “shots on goal”, and also makes me shrink down the expectations on any given project. If I put all my eggs in one basket, it puts immense pressure on that project to succeed and make a lot of money. Doing 8 projects forces me to think smaller, nimbler, and it doesn’t hurt as much if something fails, I’ll just go on to the next one.

Today’s Scorecard

As of today, Tentacle Project 1, which I’ve already launched, is my brand strategy/marketing consultancy, and right now it’s making up 100% of my income. So my portfolio is not diversified at all, it looks like this:

But I will cut myself some slack as I only started this experiment a couple months ago.

I’m about to launch Tentacle Project 2, which is a crowdfunded physical poster that I will sell on Kickstarter. This is completely unrelated to my consulting work, and would ideally give me something close to an 80%/20% mix.

By the end of 2025, I hope to launch at least 4 more tentacles, one per quarter, bringing me to 6 tentacles, perhaps with an allocation of something like 40%/20%/20%/15%/5%/0%. This is an imaginary allocation, as stated above I am not trying to have each tentacle contribute an equal amount, but I like the idea of making the allocation as diverse as possible, to reduce risk, and also prove that I’m able to generate income from multiple sources.

I’d love to hear from you

If you are trying to do a portfolio career, I’d love to hear how you’re approaching it, and how you are selecting the different “jobs” in your portfolio. Add a comment or DM me, I’d love to meet other people doing something similar.

Until next time,

Dave