Consider me a fellow Octopus who refuses to "live with seven tentacles tied behind my back" — what a line, this entire piece resonates so strongly! In fact, I’ve been meaning to reach out since I saw your draft pop up in WoP/Circle, because I adore this concept.
Although, the “tentacle allocation strategy” you mentioned in your previous essay is what I find myself struggling with at the moment: It’s a combination of the classic “not enough hours in the day” + lack of daily/weekly consistency killing my SEO and social media growth efforts of many of my projects. Any advice on that front? Maybe I’d be better off pairing back to a five-pronged starfish?
Hi Emily, awesome you are in WoP too! So many Substackers in there, it's been fun to connect with people.
Glad to meet a fellow Octopus! The tentacle allocation strategy can definitely be challenging. One thing to keep in mind is that there is no possible way to do 8 full time jobs, maybe not even 2 or 3! So you have to envision the tentacles in a different way. Some of them can require a lot of care and nature, eg. social media posting, etc, but some of them will have to be passive income, aka make money while you sleep. For these projects you can put in a lot of effort up front, but once it's launched it should run on autopilot as much as possible.
Another way to tackle the "not enough hours in the day" is to see if there's any way to automate those tentacles, again so they run on autopilot if possible.
I don't know what all of your tentacles are, but if they all require a lot of time commitment you may wish to just focus on 2 or 3, and just nurture those. No need to put pressure on yourself to get to 8.
I'm happy to answer any other questions you may have, if you want to DM me on here I'm glad to discuss anything you don't want to put in public comments! Would love to hear more about your tentacle projects and how you're trying to grow them!
Like Emily, I was also wondering about time commitment 8 jobs would take! It intimidated me at first. But then, it really helped when you pointed out, Dave, that some of those could be passive or ebb and flow. And suddenly I could see how the tetris could work.
The other concept I have in the model is that all 8 tentacles don't have to earn money. One of my portfolio rules is that at least one of the eight should make no money. It should just be for fun.
The other thing I've been thinking about is how Octopuses can lose a tentacle, and regenerate a new one. It may very well be that a tentacle only lasts for a month, a week, or even a day, then gets dropped. So every tentacle is not necessarily a full or even part time money making endeavor.
Being entrepreneur already implies becoming octopus 🐙 as we need to integrate new roles we’ve never played before. If you add different niches you can easily make a small calculation 8*8…. :-)) lovely and amazing octopus we are getting here.
Hi Aleksandra, entrepreneurship absolutely requires an octopus way of being and working. You must learn new things and learn them quickly, explore many options, be fluid in thinking, and adapt to fluctuating markets and customer needs. That’s why I like the octopus metaphor, particularly for people who want to start their own business or a portfolio career, the octopus mindset can be immensely helpful.
This: "You are not a one dimensional person, so why does your life’s work have to be? Why can’t we continue our child-like curiosity as working adults?" is exactly what my friend, aged 40, keeps saying.
I needed this. I thought something was wrong with me—why can't I pick!!! I am an octopus person. I like a lot of things but not one thing is so beloved I would dedicate my life to it. Thank you for these words. Extremely relatable and freeing.
Hi Maddy, thanks I'm glad this helped free your thinking around this topic, and it's nice to meet another Octopus Person! I've decided to go against the prevailing wisdom and just be who I am - someone who is interested in a wide variety of things, all at the same time.
Very interesting! I'm actually working on a piece about this very topic. While I agree with a lot of what you say, I think it can be misleading advice, especially when starting a business. It's easy to look at established creators like Dan Koe and making people think that simply being themselves is enough. But that's neglecting the crucial element of organic growth. Looking at his own journey, it seems like niching down is exactly how he got to where he is. He started focused on web design and digital marketing on Twitter... Then broadened to online business in general, incorporating health and mental frameworks into the conversation. Now he's talking about mindset, solopreneurship, and growth from a more philosophical perspective. It's a clear progression from a niche.
Maybe some creators can jump right into broad topics, but from what I’ve seen, most successful ones niche down first to build an audience before experimenting with diverse content.
Think of Apple. They started in the very specific niche of personal computers. Even Steve Jobs, when he returned, drastically reduced their product lines to regain focus. Apple's later success came from expanding from that strong foundation, not starting broad. Now they're a lifestyle brand, almost beyond definition. The same applies to creators.
It's easier to get noticed in a smaller pond. By focusing on a specific problem or audience, you can cut through the noise and attract your ideal customers.
So, while your unique perspective is your ultimate differentiator, "you as the niche" shouldn't be mistaken for a starting strategy. It's a destination, not a departure point. A more effective approach is to strategically "niche down" initially—focus on a specific area where your skills and passions intersect, build an audience, and then expand organically as you grow and evolve.
Hi Philipp thanks for your comments. If you are trying to start a business, niche down is good advice, as I stated in the essay. But many people nowadays are not trying to start a business. They are trying to figure out how they want to live, what hobbies to explore, or how to express themselves creatively, and maybe make some money, but maybe not. For those people, niching down can be paralyzing, because they're being forced to pick just one thing, at the very time when they should be exploring and experimenting with a wide variety of things. So another way to look at it is that niching down is the misleading advice, because it's been applied to nearly everything, including people who should be niching wide.
I don't know all of Dan Koe's history, but I'm pretty sure he was looking for ways to make money online early on. If I remember one of his videos right, he actually tried a wide variety of ways to make money. So at the beginning he was not niching down, he was actually niching wide. He found that he could make some money doing web design, but he tried other things too. Looking back you can say he picked a niche - web design. But that's only partially true. He was trying multiple niches to find something that worked. So he was also niching wide. He then discovered other ways to make money by niching wide, and put effort into the ones that were most profitable. So another way to look at his journey is that he was constantly niching wide, to find things to niche down on.
But let's talk about business specifically since that's your interest area. You gave an example like Apple. Looking back it's easy to say Steve Jobs niched down by starting in personal computers. But is that really true? If you read his biography, he didn't start his career building personal computers. Jobs and Wozniak tried a wide variety of things before building a true personal computer. They made a "blue box" for some kind of telephony. Then boards for Atari. At the very beginning they were niching wide, trying to find something interesting to make. Through those explorations they realized that they were on the cusp of a new revolution in computing - the personal computer, and went all in on creating Apple.
I think it's easy to simplify the histories of companies and think it was such genius that the founders hit upon their amazing invention from day one. But that's not really true. Bill Gates had a similar meandering, niching wide period before niching down on Microsoft OS.
You might find some stories of companies or founders who niched down on day one. But you've also heard of pivots right? There are probably just as many stories if not more, of companies who tried one or more other things before finding their big success. So niching down often looks successful only after niching wide.
Wow, thanks for your thoughtful reply. I appreciate you clarifying your perspective on "niching down" and its potential downsides for those exploring hobbies or creative expression. I agree that exploration and experimentation are crucial, especially when you're trying to discover your passions and find your place in the world. In fact, I think we're actually on the same page about the importance of this initial phase of exploration. Perhaps I was too quick to jump to the business application of "niching" and didn't fully acknowledge the value of "niching wide" in the context of self-discovery. My apologies if my initial comment came across as dismissive of that aspect.
However, when the goal is specifically building a sustainable, profitable business, I believe a more strategic approach to niching is essential. While experimenting with different options, as you described with Dan Koe's early stages, is valuable for finding your footing, his current success isn't solely a result of that initial "niching wide" phase. His current broad reach is built on the foundation he established through his initial focus on web design and digital marketing. That focus allowed him to develop expertise, build an audience, and establish a platform for later expansion. He strategically niched up from a niche.
The Apple example illustrates this point even more clearly. While Jobs had his period of exploration, Apple's breakthrough came from niching down to personal computers and mastering that market before expanding into other areas. Their later "nicheless" status (which is a misnomer – they're more accurately a "category of one") is a result of strategic expansion from a strong, focused foundation, not simply being "everything to everyone" from day one.
The core of my argument is that "you as the niche," while a powerful concept for personal branding, shouldn't be mistaken for a complete business strategy, especially when starting out. It's a destination, not a departure point. It’s the result of the niching up process, not the starting point. A more effective approach, in my view, is to strategically "niche down" initially—focus on a specific area where your skills and passions intersect, build a solid foundation, then expand organically as you grow and evolve. This allows you to leverage the power of pattern recognition (essential for developing true expertise) and ultimately position yourself as a "category of one," owning a space of your own creation.
I believe this "niche down, then niche up" strategy provides a more robust framework for building a successful and impactful business, while still allowing for the exploration and experimentation that are crucial for finding your true calling.
Thanks Phillip, I like it! The niching strategy for business varies depending on your stage and product strategy, and that strategy changes over time. So maybe it’s first Niche Wide (exploration), then Niche Down (focus), then Niche Out (expansion)?
That is a neat concept! I hadn't consciously thought about the exploration phase ("Niche Wide") as a distinct step, but it makes perfect sense. Looking back, I realize I've instinctively followed this in all my businesses. I think this phase of exploration is a very important step. I would even say there is an iterative process between niching wide and niching down. Kind of like the Lean Startup approach.
On a personal level, this exploration allows you to discover your passions, identify your strengths, and clarify what you truly want to pursue. It's about trying different things, getting feedback, and refining your direction based on that experience.
On the business side, it's the same principle, but instead of self-discovery, you're focused on market discovery. You're testing different niches, understanding your ideal customers, and validating your business ideas before committing to a specific focus.
Hear hear! Reminds me of how the famous quote, that is often cut short, actually goes, "Jack of all trades, master of none, though oftentimes better than a master of one."
I think Dave, that you've just diagnosed me as an octopus. I have so many interests it's hard to concentrate on just one but also I can be incredibly focussed on one thing to the detriment of the others. Then there's the procrastination, I can't do everything so I end up doing nothing. It can be hard being an octopus sometimes!
Hi Mark, I can relate to everything you said. I've always had lots of interests. This can be a strength, in that you know a lot about many things, but it can also be a source of constant distraction and procrastination too.
That's why I like the Octopus model, instead of one extreme where you're forced to pick one thing, and the other extreme, where you're paralyzed because can't do everything, 8 feels just about right. It's enough tentacles to keep you fully engaged, but not so many that you become overwhelmed. If I may make a suggestion: see if you can come up with a list of 8 things you want to investigate/do/have fun with in the final quarter of the year. And forget everything else. You should be able to make progress on at least a couple tentacles, and avoid the procrastination of feeling like you can't do everything.
Don't give in to the pressure to Niche Down, that's only useful for a few narrow applications.
I saw you're wrestling with 2 separate newsletters, I pondered doing this too, but another way to think about it: people want to follow YOU the person, not necessarily a topic. YOU are the niche. Just be yourself. Write about your life. Share what you're up to. Topics come and go, but people follow people.
Also, if you're wrestling with what to do, how to move forward with life, something that's helped me is to be like an Octopus and just meander around your life's "ocean floor". There's plenty to be explored. If you find some coral or fellow animal that piques your interest, investigate it. Explore it. Manipulate with a tentacle. Be curious. Ironically, sometimes clear direction emerges through random meandering. It seems counterintuitive, doesn't it? But I've found that just thinking about what to do usually results in paralyzation/frustration/procrastination, as all potential action just stays in my head. Just keep extending tentacles into the world until you find something fun and inspiring to play with.
Thank you, Dave for taking the time to reply! I'm very likely an Octopus. I've given up on narrowing anything and just go about exploring everything that peaks an interest. Your approach really helped.
"You are not a one dimensional person, so why does your life’s work have to be?" - YES DAVE!! I'm going to be writing soon about discovering that I'm not a one-dimensional person. Love this too - "Why can’t we continue our child-like curiosity as working adults?"
You are using a language that needs to reach the more conventional "in a box" entrepreneurs. Being an octopus myself I struggle at selling the unsellable. If it's tangible, great. If not, it leaves a gap between potential investors that only have eyes and interest for stuff that is sellable.
Hi Eric, If you're looking for investors, they are unlikely to invest in your entire portfolio of tentacles, unless they can see how every single one of them can give them a return on their investment, either independently, or as a portfolio. I would suggest trying to get investment for one tentacle first, prove that it can work, then seek investment for tentacle #2. Investors like to have confidence that the entrepreneur can deliver. If you can prove you can deliver ROI on tentacle #1, they are more likely to be interested in tentacle #2, then #3, and so on.
Consider me a fellow Octopus who refuses to "live with seven tentacles tied behind my back" — what a line, this entire piece resonates so strongly! In fact, I’ve been meaning to reach out since I saw your draft pop up in WoP/Circle, because I adore this concept.
Although, the “tentacle allocation strategy” you mentioned in your previous essay is what I find myself struggling with at the moment: It’s a combination of the classic “not enough hours in the day” + lack of daily/weekly consistency killing my SEO and social media growth efforts of many of my projects. Any advice on that front? Maybe I’d be better off pairing back to a five-pronged starfish?
Hi Emily, awesome you are in WoP too! So many Substackers in there, it's been fun to connect with people.
Glad to meet a fellow Octopus! The tentacle allocation strategy can definitely be challenging. One thing to keep in mind is that there is no possible way to do 8 full time jobs, maybe not even 2 or 3! So you have to envision the tentacles in a different way. Some of them can require a lot of care and nature, eg. social media posting, etc, but some of them will have to be passive income, aka make money while you sleep. For these projects you can put in a lot of effort up front, but once it's launched it should run on autopilot as much as possible.
Another way to tackle the "not enough hours in the day" is to see if there's any way to automate those tentacles, again so they run on autopilot if possible.
I don't know what all of your tentacles are, but if they all require a lot of time commitment you may wish to just focus on 2 or 3, and just nurture those. No need to put pressure on yourself to get to 8.
I'm happy to answer any other questions you may have, if you want to DM me on here I'm glad to discuss anything you don't want to put in public comments! Would love to hear more about your tentacle projects and how you're trying to grow them!
Like Emily, I was also wondering about time commitment 8 jobs would take! It intimidated me at first. But then, it really helped when you pointed out, Dave, that some of those could be passive or ebb and flow. And suddenly I could see how the tetris could work.
The other concept I have in the model is that all 8 tentacles don't have to earn money. One of my portfolio rules is that at least one of the eight should make no money. It should just be for fun.
The other thing I've been thinking about is how Octopuses can lose a tentacle, and regenerate a new one. It may very well be that a tentacle only lasts for a month, a week, or even a day, then gets dropped. So every tentacle is not necessarily a full or even part time money making endeavor.
Being entrepreneur already implies becoming octopus 🐙 as we need to integrate new roles we’ve never played before. If you add different niches you can easily make a small calculation 8*8…. :-)) lovely and amazing octopus we are getting here.
Hi Aleksandra, entrepreneurship absolutely requires an octopus way of being and working. You must learn new things and learn them quickly, explore many options, be fluid in thinking, and adapt to fluctuating markets and customer needs. That’s why I like the octopus metaphor, particularly for people who want to start their own business or a portfolio career, the octopus mindset can be immensely helpful.
This: "You are not a one dimensional person, so why does your life’s work have to be? Why can’t we continue our child-like curiosity as working adults?" is exactly what my friend, aged 40, keeps saying.
I fully agree.
I needed this. I thought something was wrong with me—why can't I pick!!! I am an octopus person. I like a lot of things but not one thing is so beloved I would dedicate my life to it. Thank you for these words. Extremely relatable and freeing.
Hi Maddy, thanks I'm glad this helped free your thinking around this topic, and it's nice to meet another Octopus Person! I've decided to go against the prevailing wisdom and just be who I am - someone who is interested in a wide variety of things, all at the same time.
Very interesting! I'm actually working on a piece about this very topic. While I agree with a lot of what you say, I think it can be misleading advice, especially when starting a business. It's easy to look at established creators like Dan Koe and making people think that simply being themselves is enough. But that's neglecting the crucial element of organic growth. Looking at his own journey, it seems like niching down is exactly how he got to where he is. He started focused on web design and digital marketing on Twitter... Then broadened to online business in general, incorporating health and mental frameworks into the conversation. Now he's talking about mindset, solopreneurship, and growth from a more philosophical perspective. It's a clear progression from a niche.
Maybe some creators can jump right into broad topics, but from what I’ve seen, most successful ones niche down first to build an audience before experimenting with diverse content.
Think of Apple. They started in the very specific niche of personal computers. Even Steve Jobs, when he returned, drastically reduced their product lines to regain focus. Apple's later success came from expanding from that strong foundation, not starting broad. Now they're a lifestyle brand, almost beyond definition. The same applies to creators.
It's easier to get noticed in a smaller pond. By focusing on a specific problem or audience, you can cut through the noise and attract your ideal customers.
So, while your unique perspective is your ultimate differentiator, "you as the niche" shouldn't be mistaken for a starting strategy. It's a destination, not a departure point. A more effective approach is to strategically "niche down" initially—focus on a specific area where your skills and passions intersect, build an audience, and then expand organically as you grow and evolve.
Hi Philipp thanks for your comments. If you are trying to start a business, niche down is good advice, as I stated in the essay. But many people nowadays are not trying to start a business. They are trying to figure out how they want to live, what hobbies to explore, or how to express themselves creatively, and maybe make some money, but maybe not. For those people, niching down can be paralyzing, because they're being forced to pick just one thing, at the very time when they should be exploring and experimenting with a wide variety of things. So another way to look at it is that niching down is the misleading advice, because it's been applied to nearly everything, including people who should be niching wide.
I don't know all of Dan Koe's history, but I'm pretty sure he was looking for ways to make money online early on. If I remember one of his videos right, he actually tried a wide variety of ways to make money. So at the beginning he was not niching down, he was actually niching wide. He found that he could make some money doing web design, but he tried other things too. Looking back you can say he picked a niche - web design. But that's only partially true. He was trying multiple niches to find something that worked. So he was also niching wide. He then discovered other ways to make money by niching wide, and put effort into the ones that were most profitable. So another way to look at his journey is that he was constantly niching wide, to find things to niche down on.
But let's talk about business specifically since that's your interest area. You gave an example like Apple. Looking back it's easy to say Steve Jobs niched down by starting in personal computers. But is that really true? If you read his biography, he didn't start his career building personal computers. Jobs and Wozniak tried a wide variety of things before building a true personal computer. They made a "blue box" for some kind of telephony. Then boards for Atari. At the very beginning they were niching wide, trying to find something interesting to make. Through those explorations they realized that they were on the cusp of a new revolution in computing - the personal computer, and went all in on creating Apple.
I think it's easy to simplify the histories of companies and think it was such genius that the founders hit upon their amazing invention from day one. But that's not really true. Bill Gates had a similar meandering, niching wide period before niching down on Microsoft OS.
You might find some stories of companies or founders who niched down on day one. But you've also heard of pivots right? There are probably just as many stories if not more, of companies who tried one or more other things before finding their big success. So niching down often looks successful only after niching wide.
Wow, thanks for your thoughtful reply. I appreciate you clarifying your perspective on "niching down" and its potential downsides for those exploring hobbies or creative expression. I agree that exploration and experimentation are crucial, especially when you're trying to discover your passions and find your place in the world. In fact, I think we're actually on the same page about the importance of this initial phase of exploration. Perhaps I was too quick to jump to the business application of "niching" and didn't fully acknowledge the value of "niching wide" in the context of self-discovery. My apologies if my initial comment came across as dismissive of that aspect.
However, when the goal is specifically building a sustainable, profitable business, I believe a more strategic approach to niching is essential. While experimenting with different options, as you described with Dan Koe's early stages, is valuable for finding your footing, his current success isn't solely a result of that initial "niching wide" phase. His current broad reach is built on the foundation he established through his initial focus on web design and digital marketing. That focus allowed him to develop expertise, build an audience, and establish a platform for later expansion. He strategically niched up from a niche.
The Apple example illustrates this point even more clearly. While Jobs had his period of exploration, Apple's breakthrough came from niching down to personal computers and mastering that market before expanding into other areas. Their later "nicheless" status (which is a misnomer – they're more accurately a "category of one") is a result of strategic expansion from a strong, focused foundation, not simply being "everything to everyone" from day one.
The core of my argument is that "you as the niche," while a powerful concept for personal branding, shouldn't be mistaken for a complete business strategy, especially when starting out. It's a destination, not a departure point. It’s the result of the niching up process, not the starting point. A more effective approach, in my view, is to strategically "niche down" initially—focus on a specific area where your skills and passions intersect, build a solid foundation, then expand organically as you grow and evolve. This allows you to leverage the power of pattern recognition (essential for developing true expertise) and ultimately position yourself as a "category of one," owning a space of your own creation.
I believe this "niche down, then niche up" strategy provides a more robust framework for building a successful and impactful business, while still allowing for the exploration and experimentation that are crucial for finding your true calling.
Thanks Phillip, I like it! The niching strategy for business varies depending on your stage and product strategy, and that strategy changes over time. So maybe it’s first Niche Wide (exploration), then Niche Down (focus), then Niche Out (expansion)?
That is a neat concept! I hadn't consciously thought about the exploration phase ("Niche Wide") as a distinct step, but it makes perfect sense. Looking back, I realize I've instinctively followed this in all my businesses. I think this phase of exploration is a very important step. I would even say there is an iterative process between niching wide and niching down. Kind of like the Lean Startup approach.
On a personal level, this exploration allows you to discover your passions, identify your strengths, and clarify what you truly want to pursue. It's about trying different things, getting feedback, and refining your direction based on that experience.
On the business side, it's the same principle, but instead of self-discovery, you're focused on market discovery. You're testing different niches, understanding your ideal customers, and validating your business ideas before committing to a specific focus.
Hear hear! Reminds me of how the famous quote, that is often cut short, actually goes, "Jack of all trades, master of none, though oftentimes better than a master of one."
Yeah the part that gets cutoff is the most important bit!
I think Dave, that you've just diagnosed me as an octopus. I have so many interests it's hard to concentrate on just one but also I can be incredibly focussed on one thing to the detriment of the others. Then there's the procrastination, I can't do everything so I end up doing nothing. It can be hard being an octopus sometimes!
Hi Mark, I can relate to everything you said. I've always had lots of interests. This can be a strength, in that you know a lot about many things, but it can also be a source of constant distraction and procrastination too.
That's why I like the Octopus model, instead of one extreme where you're forced to pick one thing, and the other extreme, where you're paralyzed because can't do everything, 8 feels just about right. It's enough tentacles to keep you fully engaged, but not so many that you become overwhelmed. If I may make a suggestion: see if you can come up with a list of 8 things you want to investigate/do/have fun with in the final quarter of the year. And forget everything else. You should be able to make progress on at least a couple tentacles, and avoid the procrastination of feeling like you can't do everything.
I am totally an octopus person
Awesome welcome to the Octopus tribe!
I feel so seen. Niching down never sat right with me. Now I’m just living it all, because everything else is too hard.
Hi Yvonne, you must be an Octopus :)
Don't give in to the pressure to Niche Down, that's only useful for a few narrow applications.
I saw you're wrestling with 2 separate newsletters, I pondered doing this too, but another way to think about it: people want to follow YOU the person, not necessarily a topic. YOU are the niche. Just be yourself. Write about your life. Share what you're up to. Topics come and go, but people follow people.
Also, if you're wrestling with what to do, how to move forward with life, something that's helped me is to be like an Octopus and just meander around your life's "ocean floor". There's plenty to be explored. If you find some coral or fellow animal that piques your interest, investigate it. Explore it. Manipulate with a tentacle. Be curious. Ironically, sometimes clear direction emerges through random meandering. It seems counterintuitive, doesn't it? But I've found that just thinking about what to do usually results in paralyzation/frustration/procrastination, as all potential action just stays in my head. Just keep extending tentacles into the world until you find something fun and inspiring to play with.
Thank you, Dave for taking the time to reply! I'm very likely an Octopus. I've given up on narrowing anything and just go about exploring everything that peaks an interest. Your approach really helped.
"You are not a one dimensional person, so why does your life’s work have to be?" - YES DAVE!! I'm going to be writing soon about discovering that I'm not a one-dimensional person. Love this too - "Why can’t we continue our child-like curiosity as working adults?"
Hi Jessica that's great! I will subscribe, I look forward to reading your piece about it!
Why thank you! Should be up by the end of the year - in the meantime feel free to have a look around at what else I've written :)
You are using a language that needs to reach the more conventional "in a box" entrepreneurs. Being an octopus myself I struggle at selling the unsellable. If it's tangible, great. If not, it leaves a gap between potential investors that only have eyes and interest for stuff that is sellable.
I'd love to have your point of view on that.
Hi Eric, If you're looking for investors, they are unlikely to invest in your entire portfolio of tentacles, unless they can see how every single one of them can give them a return on their investment, either independently, or as a portfolio. I would suggest trying to get investment for one tentacle first, prove that it can work, then seek investment for tentacle #2. Investors like to have confidence that the entrepreneur can deliver. If you can prove you can deliver ROI on tentacle #1, they are more likely to be interested in tentacle #2, then #3, and so on.