I really resonate with your "portfolio of work" paradigm Dave. The wisdom is providing multiple income streams (so nobody "owns" you) and a variety of work projects so boredom is less of a threat.
Aristotle says "Where your talents and the needs of the world meet, there lies your vocation". As more people want or need to work for themselves, developing a brand that draws attention and money will be key. That requires strong strategic thinking, which you are ready and able to support. Sounds very promising. Onward! 👏
Thanks Baird, I didn't elaborate on this in the post, but "future proofing" my career via multiple income streams is definitely a factor here, so no one "owns" me and thus cannot fire me or lay me off. Also a bit of portfolio diversification helps too in case one industry sector tanks, I will not go down with it.
Hi Melissa, don’t give in to the prevailing “wisdom” of picking one thing. It’s bad advice for people with wide ranging interests, who have the capacity to handle more than one thing. So much of life is actually “multiple things” all the time eg family, friends, hobbies, exercise, entertainment, etc. Why is it ok for the rest of your life to be about many things, but work has to be only 1? I say pursue them all.
Question: what are your requirements for parts of the portfolio? Does it have to include the potential to earn an income?
For example, why would this newsletter NOT also be included as a project? Or you could expand book under the topic "Writing." Or call it "Media," which could be deployed in a multitude of ways over time. Just some thought.
P.S. Love the idea of adding "passion projects" to the portfolio. I think that's missing for a lot of people.
Thanks for your comments, on the subject of portfolio requirements, I have not put this to paper, and it will be the subject of a future post, but it is some mix of:
1) Something I have personal capability to actuate and deploy. So it can't be too big eg, "solve climate change" or something I have zero experience in eg "start a hedge fund".
2) At least one tentacle MUST earn income. I do not have enough money to retire so still need to make living somehow. Ideally more than one tentacle makes some money, for diversification.
3) At least one tentacle MUST be just for fun/passion project. This alleviates pressure to make this all about money making, which distorts the filter towards commercial-only projects. I'm trying to have more fun in life, and commercial work generally makes me more serious and less fun. Also the point is to be an Octopus. Sometimes Octopuses just explore/meander around for fun, not on a mission to find food, build a den, etc.
4) As much as possible the 8 tentacles are in completely different arenas. This is not a "theme and variations" experiment, so I don't want 8 things related to one topic or expertise. In other words, this should NOT result in a book about tennis, Youtube channel about tennis, build a community about tennis, start an online tennis instruction school, etc. That defeats the polymathic element of the experiment.
5) Think in "small bets". This answers your newsletter question: "Writing" at the moment is too big a bucket, as that could mean a book, this Substack, a downloadable PDF, copywriting agency, etc. It helps me to think of the tentacles as individual deliverable projects. This Substack doesn't feel like a project to me (yet) as I've only written 3-4 posts on this subject, and it's more like a journal of my thoughts right now, but I could see it evolving into "my octopus journey and how to build a portfolio career" with a paid subscription, accompanying course, etc. If I get that far, I think this Substack rightfully becomes a tentacle. In my head it's starting to move in that direction.
6) Be ok with "failure". Octopuses can lose a tentacle and regenerate it. I want this attitude towards the projects. If a project doesn't work or I end up not having any fun, I can freely cut it off and grow a new one in its place.
That's about as far as I've gotten. I would like to come up with 2 more to make it 8 guiding principles, you know cuz octopuses have 8 arms, but can't think of anything at the moment. Would love to hear your thoughts!
All of this makes sense and sounds like the topic for a great post! I think helping people understand how you define projects, decide what to include/exclude, balance them, etc. is all great stuff to share. Your thought process may help other people set their own requirements.
Last thought... having 8 projects is ambitious, so more power to you! But 8 SIMULTANEOUSLY, seems daunting, at least to me.
One way I've thought about this is I've decided to do my work/writing in SERIES (one at a time). Or at least there's always a primary focus that shifts. I like to focus on something, dig in, but not be stuck there forever. Putting it into a series, with a packaged start-and-end, is a nice way to do that without over-committing to one forever. Just another way to do it.
Yeah sometimes I wonder if 8 is too much but some of these might be very low time commitment tentacles, for example once I write and publish my book, the time commitment on that should go down significantly to just maintenance marketing.
I also thought about “sequential” vs “simultaneous” tentacles and decided on simultaneous because I like jumping around between projects as I feel inspired to work on them. I sort of naturally work on multiple things at a time, I know that drives some people batty but I just prefer working that way. There is also no natural order to my projects as they are largely unrelated, so aside from my personal preference I don’t see any way to arrange them chronologically.
I would take the sequential approach if I was trying to do venture scale startups due to the time commitment eg become a “serial entrepreneur” but I only have one idea that might even qualify for that. Most of the tentacles aren’t even “seed” worthy so I think of this more like Y combinator for personal interests: invest small quantities of time and money into a multitude of what will start as tiny personal projects. Some might grow big, some make money, some will not, some will fail, some will do well then naturally end.
I like how you’ve arranged your writing into a natural series of groupings that also roughly mirror stages of your journey, so “serialization” makes total sense there. Feels like you’re building enough content for a book or documentary!
Bravo. I heartily applaud your intentional "Everyman" approach. I'm following a similar-ish journey...and certainly some common interests. The more inspiration, the better that doesn't fall back on: a) billionaires and enterprise brands, b) unicorn valuations and scale as the goal, c) climate change, d) finding one's authentic life by throwing everything out and moving to Costa Rica (although more power to the folks who can pull that off, too). [My own Project 2, if/when I launch, is to amplify everyday innovators who -- although they may not ID that way -- are, in their own, real-life ways, chipping away at Meaningful Problems.]
Echoing your counsel to branch from existing/past work, I on-and-off freelance consult for niche consultancies in a hard-to-describe blend of brand strategy / customer research / executive communities of practice / expert content.
I’m on a pretty similar path. Three years ago, dissatisfied with my work, I closed my advertising company and spent three years camping with my family, searching for what to do next. In the end, I wrote a book about some of the lessons I learned, and one of them is that I want to dedicate myself to several projects instead of adopting a new single profession.
So far, my seven tentacles are:
- Taking care of and being present for my wife and five children
I’ve also been doing some marketing consulting for a few companies, but I hope to phase that out as soon as the other areas begin to generate more income.
It's nice to know that more people are involved in a similar project, especially you, with so many similarities on them.
There are so many parallels in our life journeys! I used to work as an agency graphic designer and will put that skill to use in many of my tentacles, including selling posters and art prints. I also long for more balanced, more creative, more meaningful living, and ability to use more of my talents across multiple "professions". I followed you pretty early in my time on Substack, congrats on the book launch and other projects, would definitely love to stay in touch!
Glad to help in any way I can. I am writing my book right now and hope to launch in a few months on Amazon. I will probably share some of the process on here so other people can see exactly how I’m doing it, but let me know if you have anything in particular that you’d like to learn.
Coming soon! I will write a post dedicated to this to explain the concept fully, but in a nutshell it's a combination of a calendar, habit tracker, life regret minimizer, important milestone log, and motivational tool to not waste your life. All on 1 piece of paper.
I really resonate with your "portfolio of work" paradigm Dave. The wisdom is providing multiple income streams (so nobody "owns" you) and a variety of work projects so boredom is less of a threat.
Aristotle says "Where your talents and the needs of the world meet, there lies your vocation". As more people want or need to work for themselves, developing a brand that draws attention and money will be key. That requires strong strategic thinking, which you are ready and able to support. Sounds very promising. Onward! 👏
Thanks Baird, I didn't elaborate on this in the post, but "future proofing" my career via multiple income streams is definitely a factor here, so no one "owns" me and thus cannot fire me or lay me off. Also a bit of portfolio diversification helps too in case one industry sector tanks, I will not go down with it.
This is comforting to me - I have like 4-5 career ideas and have kept feeling the tension between focusing on 1-2 or viewing them each as experiments
Melissa check this post out, where I discuss working on more than one thing https://open.substack.com/pub/davekang/p/my-work-as-an-octopus-generalist-income-from-multiple-interests?r=tvag3&utm_medium=ios
Hi Melissa, don’t give in to the prevailing “wisdom” of picking one thing. It’s bad advice for people with wide ranging interests, who have the capacity to handle more than one thing. So much of life is actually “multiple things” all the time eg family, friends, hobbies, exercise, entertainment, etc. Why is it ok for the rest of your life to be about many things, but work has to be only 1? I say pursue them all.
Dave - love everything you are doing here!
Question: what are your requirements for parts of the portfolio? Does it have to include the potential to earn an income?
For example, why would this newsletter NOT also be included as a project? Or you could expand book under the topic "Writing." Or call it "Media," which could be deployed in a multitude of ways over time. Just some thought.
P.S. Love the idea of adding "passion projects" to the portfolio. I think that's missing for a lot of people.
Hey Rick,
Thanks for your comments, on the subject of portfolio requirements, I have not put this to paper, and it will be the subject of a future post, but it is some mix of:
1) Something I have personal capability to actuate and deploy. So it can't be too big eg, "solve climate change" or something I have zero experience in eg "start a hedge fund".
2) At least one tentacle MUST earn income. I do not have enough money to retire so still need to make living somehow. Ideally more than one tentacle makes some money, for diversification.
3) At least one tentacle MUST be just for fun/passion project. This alleviates pressure to make this all about money making, which distorts the filter towards commercial-only projects. I'm trying to have more fun in life, and commercial work generally makes me more serious and less fun. Also the point is to be an Octopus. Sometimes Octopuses just explore/meander around for fun, not on a mission to find food, build a den, etc.
4) As much as possible the 8 tentacles are in completely different arenas. This is not a "theme and variations" experiment, so I don't want 8 things related to one topic or expertise. In other words, this should NOT result in a book about tennis, Youtube channel about tennis, build a community about tennis, start an online tennis instruction school, etc. That defeats the polymathic element of the experiment.
5) Think in "small bets". This answers your newsletter question: "Writing" at the moment is too big a bucket, as that could mean a book, this Substack, a downloadable PDF, copywriting agency, etc. It helps me to think of the tentacles as individual deliverable projects. This Substack doesn't feel like a project to me (yet) as I've only written 3-4 posts on this subject, and it's more like a journal of my thoughts right now, but I could see it evolving into "my octopus journey and how to build a portfolio career" with a paid subscription, accompanying course, etc. If I get that far, I think this Substack rightfully becomes a tentacle. In my head it's starting to move in that direction.
6) Be ok with "failure". Octopuses can lose a tentacle and regenerate it. I want this attitude towards the projects. If a project doesn't work or I end up not having any fun, I can freely cut it off and grow a new one in its place.
That's about as far as I've gotten. I would like to come up with 2 more to make it 8 guiding principles, you know cuz octopuses have 8 arms, but can't think of anything at the moment. Would love to hear your thoughts!
All of this makes sense and sounds like the topic for a great post! I think helping people understand how you define projects, decide what to include/exclude, balance them, etc. is all great stuff to share. Your thought process may help other people set their own requirements.
Last thought... having 8 projects is ambitious, so more power to you! But 8 SIMULTANEOUSLY, seems daunting, at least to me.
One way I've thought about this is I've decided to do my work/writing in SERIES (one at a time). Or at least there's always a primary focus that shifts. I like to focus on something, dig in, but not be stuck there forever. Putting it into a series, with a packaged start-and-end, is a nice way to do that without over-committing to one forever. Just another way to do it.
Example: https://newsletter.thewayofwork.com/p/series
Series right now is article-series. But a future series could be a book, a business launch, a documentary, whatever!
Yeah sometimes I wonder if 8 is too much but some of these might be very low time commitment tentacles, for example once I write and publish my book, the time commitment on that should go down significantly to just maintenance marketing.
I also thought about “sequential” vs “simultaneous” tentacles and decided on simultaneous because I like jumping around between projects as I feel inspired to work on them. I sort of naturally work on multiple things at a time, I know that drives some people batty but I just prefer working that way. There is also no natural order to my projects as they are largely unrelated, so aside from my personal preference I don’t see any way to arrange them chronologically.
I would take the sequential approach if I was trying to do venture scale startups due to the time commitment eg become a “serial entrepreneur” but I only have one idea that might even qualify for that. Most of the tentacles aren’t even “seed” worthy so I think of this more like Y combinator for personal interests: invest small quantities of time and money into a multitude of what will start as tiny personal projects. Some might grow big, some make money, some will not, some will fail, some will do well then naturally end.
I like how you’ve arranged your writing into a natural series of groupings that also roughly mirror stages of your journey, so “serialization” makes total sense there. Feels like you’re building enough content for a book or documentary!
Interesting stuff as always - keep it coming
Thanks John!
Bravo. I heartily applaud your intentional "Everyman" approach. I'm following a similar-ish journey...and certainly some common interests. The more inspiration, the better that doesn't fall back on: a) billionaires and enterprise brands, b) unicorn valuations and scale as the goal, c) climate change, d) finding one's authentic life by throwing everything out and moving to Costa Rica (although more power to the folks who can pull that off, too). [My own Project 2, if/when I launch, is to amplify everyday innovators who -- although they may not ID that way -- are, in their own, real-life ways, chipping away at Meaningful Problems.]
Thanks Erin, Project 2 sounds great, what was your Project 1?
Echoing your counsel to branch from existing/past work, I on-and-off freelance consult for niche consultancies in a hard-to-describe blend of brand strategy / customer research / executive communities of practice / expert content.
Congrats, Dave! I’m so excited for your journey. A book seems wonderful. A memoir but in a truly different fashion.
I’m currently octopussing with 3 different gigs - full time job, branding/marketing/growth strategy consulting, and performance coaching!
Would be up for your 4th project. Keep us posted.
It’d have been cool if you used an octopus’s picture for your creative in the post. 😄
cool! you are already executing an octopus plan!
I tried to make an octopus photo using AI but I didn’t like any of the results, I might just have to design something myself.
I made some Octopus art some time back, coz I am a diver & love Octopuses. If you'd like to get something made for yourself, hit me up.
I am really excited to see where this project leads, I am following along closely, and also inspired!
Thanks Marco, I see you're doing a lot of writing and reading etc, are you also trying to build an Octopus-style portfolio career?
Yes, I currently have a full time job as an Infection Preventionist too, that’s what currently pays the bills
Cool, I used to market diagnostic tests for S. aureus, c.diff etc, you have a very important job!
Oh wow! Very cool! You know all about those pesky pathogens!
& thank you!
Awesome, Dave! Can’t wait to see how this project unfolds!
Thanks Jenn, it looks to be a wild ride! I'm looking forward to rolling out the other pieces, thanks for following along!
Hi, Dave.
Thanks for the text and the project.
I’m on a pretty similar path. Three years ago, dissatisfied with my work, I closed my advertising company and spent three years camping with my family, searching for what to do next. In the end, I wrote a book about some of the lessons I learned, and one of them is that I want to dedicate myself to several projects instead of adopting a new single profession.
So far, my seven tentacles are:
- Taking care of and being present for my wife and five children
- Promoting the book (https://a.co/d/6baa0CB)
- Doing more talks, especially on Zoom
- Sparking a world revolution, one silly drawing at a time (https://www.instagram.com/p/C_RateQOfxI)
- Designing logos (https://www.instagram.com/bejinha_design/)
- Selling prints online (https://www.instagram.com/p/C_bE8JKuX2s)
- Posting on Substack every day
I’ve also been doing some marketing consulting for a few companies, but I hope to phase that out as soon as the other areas begin to generate more income.
It's nice to know that more people are involved in a similar project, especially you, with so many similarities on them.
Please keep in touch.
Hi Bejinha,
There are so many parallels in our life journeys! I used to work as an agency graphic designer and will put that skill to use in many of my tentacles, including selling posters and art prints. I also long for more balanced, more creative, more meaningful living, and ability to use more of my talents across multiple "professions". I followed you pretty early in my time on Substack, congrats on the book launch and other projects, would definitely love to stay in touch!
Hi Dave, I would love to learn from you about Substack, book launches, and more.
Glad to help in any way I can. I am writing my book right now and hope to launch in a few months on Amazon. I will probably share some of the process on here so other people can see exactly how I’m doing it, but let me know if you have anything in particular that you’d like to learn.
Very cool! Excited to follow along with this and live vicariously through you.
Thanks Joyce, glad to be the guinea pig so others can vicariously go on what is shaping up to be a crazy journey!
Tell us more about Life Change Poster please.
Coming soon! I will write a post dedicated to this to explain the concept fully, but in a nutshell it's a combination of a calendar, habit tracker, life regret minimizer, important milestone log, and motivational tool to not waste your life. All on 1 piece of paper.