Dave Kang spent years trying to figure out his “one thing”. That perfect intersection of passion, skill, and purpose promised by frameworks like Ikigai. It was frustrating, and it didn’t work. So he stopped trying.

Instead, he embraced life as a CEO. No, not that kind. A “Chief Exploratory Octopus”. Living as a generalist with multiple interests (tentacles) reaching in different directions, without forcing them all to converge into one neat identity.

In this conversation, we explore why the popular Ikigai diagram isn’t actually Japanese, how to balance multiple passions without burning out, why quitting is underrated, the tyranny of calendars and optimization, and why you don’t need to win Wimbledon to live a meaningful life.

Whether you’re struggling to pick just one thing or feeling guilty about your many interests, this conversation offers a different way forward.

Connect with Dave:

• Substack: Dave Kang – Octopus Life

Recommended Books:

• The Pathless Path by Paul Millerd
• The Great Work of Your Life by Stephen Cope
• Range by David Epstein
• 4,000 Weeks by Oliver Burkeman

Full Transcript

Mike: Before we started recording, I was just talking about how I found your work, and it was actually through Substack. I think the article that I saw originally was the one where you talk about Ikigai and how it basically ruined your life.

I guess most people have heard of Ikigai—this idea that you have the thing that you’re really good at, the thing that the world needs from you, the thing that you can get paid for. And ultimately it’s a Venn diagram and it all merges onto this ideal one thing that you can do that will fulfill you and get you paid and basically do your life’s purpose.

How did that ruin your life?

Dave: Well, first of all, it didn’t totally ruin my life—that’s a bit of hyperbole. But I was upset about it for many years. I encountered this diagram years ago on the internet, and I tried to fill it out. And it was always in the back of my head because the culture of work sort of drills this concept into you—not specifically Ikigai, but this idea that you need to find your one calling, your one passion.

You need to figure out what’s your role in the world and what’s your contribution gonna be? How are you gonna make an impact in the world? And we have this pressure that we put on ourselves to find one thing, and there’s entire books written about this—just finding your one thing in life.

I just found it frustrating as an octopus kind of person, or as a multi-talented or multi-interested person who likes doing a lot of different things. I found it frustrating because I felt I didn’t have a one thing. I couldn’t figure out what that was, and I did this exercise to try to tie all my different interests together.

Is there a common thread here? And I just still couldn’t find one. And so I gave up on it, and I just felt it didn’t work for me—it just didn’t align with my personality type. So I wrote this article about its history, which is kind of fascinating. The diagram itself was never part of the original Japanese concept of Ikigai, which is by a lady named Mieko Kamiya or something like that.

And she wrote a book about this concept and it doesn’t have anything to do really with the diagram or finding your one thing. And the diagram was added later by two different people, kind of jelled into becoming what it became in popular culture. But none of these things were really—the aspiration to find one thing was not part of the original Japanese concept.

That blog post, or newsletter post, kind of took off. I mean, for me, it went viral. I’ve never had anything get more than a hundred of anything. And so to have hundreds of people commenting, and I think it’s over a thousand likes or whatever, was just kind of surprising.

I was like, wow, this really kind of hits a nerve with people. So it didn’t really ruin my life, but it did sort of redirect me and make me embrace more of who I am and just say, okay, why do I have to use someone else’s framework? Why can’t I come up with my own? And that’s my hope for people that read it—that you don’t have to fit yourself into boxes that other people create, that you can kind of invent your own.

Mike: Yeah, I definitely felt that when reading your article—it was almost a relief in a way. I think there’s a pressure, or it has been in my life. And I think it’s a running theme on this podcast, talking about identity and how it impacts us and shapes what we do and how we think about what we do.

But there’s an element of pressure I feel, and I don’t know where this came from in the last I don’t know how many years—that you should find your purpose and find that one thing that is gonna fulfill you and then also make that into your career. Make that thing the thing that also sustains you, not just creatively and not just with meaning and passion, but also financially.

What was the moment for you where you realized, oh wait, I can be a generalist, I can be an octopus? Where did this idea come from for you?

Dave: Well, I’ve always been a jack of all trades kind of person. Even as a kid, I was doing all kinds of things. I played tennis, I played the trumpet. I built things out of Legos. I was just very interested in all kinds of activities. But when I lived in Los Angeles, I was hanging out with some people who were jokingly talking about spirit animals. What’s your spirit animal? And I kind of thought, I don’t really know, but I kind of thought maybe I’m an octopus ’cause I like doing a lot of different things.

And this was many years ago. This was long before I started writing on Substack about generalism. But after I was laid off in 2023 and I did a sabbatical and was trying to kind of figure out what I wanna do when I grow up, this analogy sort of came back to me and I encountered other people who were talking about generalism on the internet.

And I thought, yeah, this is kind of me—I’m sort of broadly speaking, a generalist. But I like the octopus analogy. I didn’t really like any of the terms that are floating around there for this kind of person. There’s polymath, there’s Renaissance person, there’s multi this, multi that.

And I’m not opposed to any of those terms if other people like them. I don’t try to dissuade people from using them. But I like the octopus because it’s an organic creature. It’s more akin to us than some kind of dictionary definition of a personality type. And it also has a lot of metaphoric qualities that I think are interesting to ponder for people who consider themselves this kind of personality type.

And so that’s kind of where it came from. And then I decided to make my Substack kind of just all about that and started writing about it. And I’ve embraced it for myself as a way of living and working.

Mike: How do you actually embrace that? What does it look day to day now? Or maybe even going back, from the sabbatical to now. I would also love to understand how has it changed over time, but also just generally the practicalities. ‘Cause I think for me, I do have multiple passions. I love doing multiple things, but I think the biggest challenge is making the time for everything. And again, not feeling the pressure to go more in on one thing to make more progress on that.

And then bouncing between ideas and sort of context switching can also be tiring and a bit overwhelming, I find. How do you deal with all of that?

Dave: Yeah, it’s interesting. One of my early posts, there was someone who commented on it and just felt this is just overwhelming. I can’t do this. And then in my head I was kind of thinking, well, maybe you’re not an octopus—and not to be mean about it, but just there are certain personality types that I think can handle this. If you have ADHD, for example, which historically, unfortunately has been viewed as a deficiency of some kind, you’re doing this all the time—context switching, multitasking comes naturally to you.

And I haven’t been diagnosed with it. I don’t have—I think there’s three or four criteria. I only have two of them. So I don’t consider myself someone with ADHD, but I have some of those tendencies. And so over time I feel you can figure out the balance that works for you.

It may be that you’re a three tentacle octopus, and that’s your max capacity and you don’t have eight. And I never tell people to try to find eight exactly. Maybe you just decide that you’re gonna have three tentacles and that’s good enough for you.

And so it can be overwhelming, but I do think there’s a certain personality type who actually enjoys the complexity of eight or more things in their life. We function perfectly fine jumping around from topic to topic. When I was in corporate, I worked in marketing and design and stuff. I was in a role that serviced a lot of different people in a lot of different departments. So on any given day I’d get emails or calls from different people in my department. And I would often have to just drop whatever I was doing to pay attention to whatever hot item was on the task list for that day.

And I was fine with that. I actually enjoyed that. There were times when I didn’t wanna be interrupted if I was doing deep work, but for the most part, I was okay with interruptions and I would talk to anyone who came by my cube or called or whatever. So I think there’s a certain type that kind of enjoys the chaos of it to some degree.

And I feel that’s something to embrace. I feel that is a skill. It’s historically been seen as a problem, but I actually think it’s a skill. If you can do two things at once, you can be more productive or you can intersect things that other people can’t intersect if they’re only just focusing on one thing.

To your question about the evolution, after I was laid off and went on the sabbatical, I sort of was still in that one track mindset. I was thinking, okay, well I’m gonna be a marketing consultant and do brand work ’cause that’s my forte area. And I opened a brand consultancy practice and I needed to find brand clients.

But I quickly found that I actually wanna do other things too. I imagined, okay, let’s say I had 40 hours a week of full-on clients doing brand work. Would I really be happy and enjoy that? And deep down inside, I felt I was doing it more for job security than for personal fulfillment.

And I think I started at that point to realize I can’t do this. I can’t just do brand identity work or brand stuff for 40 hours a week for the next 20 years of my career until I retire or something. So it was a gradual evolution. I didn’t have one day where I said, I’m giving up on single track mind thinking, and I’m gonna be an octopus.

It was a gradual evolution of thinking over time, over probably the course of 12 to 16 months or so.

Mike: Listening to your answer there as well, what resonates with me—I have similar questions to you about what do I wanna do for the next 30, 40 years, whatever it is, until I retire. What is the infinite game, as I’ve heard it called as well. And I have a similar feeling that, okay, well I don’t wanna do just my day job forever until I retire—40 hours a week—and only have these slim hours of time outside of work where I do other stuff. But at the same time, I find it a really hard thing to answer.

What would I really do with all that time? And how, again, how would I balance all of the interests that I have? I mean, how do you know if you’ve found the right balance? Do you feel you have found the right balance now between all of the different activities and interests you have?

Dave: Yeah. So two things. I mean, you’re kind of pointing at one question people have—what are my interests to begin with? A lot of our interests have been suppressed over time because of career requirements. So we’ve set aside a lot of our interests. And one interesting thing about octopuses is that they’re constantly exploring things with their tentacles, right?

And if you look at videos of octopuses, the tentacles at the very ends of them get extremely thin. They’re very millimeters thick. And so they can explore all kinds of things with high sensitivity and independently. And so one thing I encourage people to do is just start exploring things.

Anything, any small thing that piques your interest, just add some more suction cups to it and grab onto it a little bit more and tinker with it, sense it, smell it, play with it—see if there’s anything there that interests you. And if not, just discard it. Octopuses pick up stuff and then they realize, oh, it’s just a rock. And then they just drop it.

And so for the exploration part, I encourage people to do really small explorations. You don’t have to invest a whole week or even a day to do this. So that’s one thing. But then in terms of balancing the portfolio, so to speak—this is a challenge and other people have brought this up to me too.

So the first thing I wanna say is that it doesn’t have to be eight equal things. Sometimes, and the diagram, some of the diagrams I have on my Substack are eight equal circles, but I’m trying to figure out if there’s some way to not have it be equal. So that’s the first thing. I think we should set aside the need to have it be equivalent things. It could be that you have one particularly strong tentacle. Again, back to the octopus behavior. If you see them doing something, sometimes two or three of their tentacles will be engaged in some activity and the others are just kind of dangling, doing nothing.

They’re resting or they’re just sitting there. And so you don’t have to deploy all eight at the same time. You can just deploy one or two and really kind of invest in those and then leave the others be for a while. So I just wanna relieve people of the pressure to deploy everything all at once.

And then in terms of just balancing out your life—everyone has limited time in the day. We each have varying amounts of free time or exploratory time. If you have a full-time job, you’ve gotta dedicate eight hours or so of that to your job. And so you are relinquished to the nights and weekends to do your explorations.

But that’s fine. That’s a good place to start, right? We do have a lot of discretionary time. If you really probe into how am I spending my days? I can almost guarantee that everyone watching this wastes more time on social media than they would like. Right? You scroll an hour and then you say, I don’t have time to do something.

Well, you kind of do. And I struggle with this too. I’m not saying it to be preachy. I wrestle with social media a lot, and I feel if you really wanna devote yourself to something, just spend some time off social media, win back that time to do the things that you want.

And then kind of lastly, to round it out for myself, I don’t really try to balance things, I guess. I don’t think of it as, okay, I’m gonna dedicate 20% of my week to this activity, or I’m gonna time block. I don’t do Pomodoro or time blocking or any of those kind of calendar things. ‘Cause again, back to the octopus, I feel those are artifacts of this generalized feeling in our society that we have to maximize efficiency over everything. We’ve gotta have a time slot for everything. We’ve gotta have a definite start and end to everything. If you think about smart goals, they have to be measurable, they have to be controlled.

Everything we do just feels artificially constrained in some way, in the name mostly of efficiency or moneymaking. And I just feel, do octopuses live this way? Do octopuses have a calendar? Do they leave their den every day thinking, okay, for 45 minutes I’m gonna go find food and then I gotta get back here and I gotta clean the den, and then I have to look after my children and then I have to do the—they kind of just are more organic and fluid and go about their day and see what they discover as they’re out and about.

And so I try to do that too. I have in the past had pretty strict schedules, especially when I was working. My calendar was filled with meetings and things I had to do. And that’s fine, but it can be exhausting too, right? On one hand, it can be tiring trying to figure out what you should do and do personal development work and find a balance in your hobbies. But on the other hand, having an extreme schedule can also be exhausting and stressful in a different way.

So I think each person kind of has to find out where on that spectrum are you in terms of how much structure do you like to have versus how much fluidity do you like to have? And then occupy that space on that continuum and then figure out, well, what’s the best way for me to live? I’m this kind of person—here I am on this continuum of extremely rigid thinking and extremely fluid thinking. Maybe I’m here. So if I’m here, then what do I wanna do to actuate that in my life?

And how do I wanna live to match up with how I like to work? So the answer is different for everyone. So I don’t have a formula to answer your balance question. I feel everybody has to kind of figure that out for themselves. But it helps to start from a place of, well, what kind of person, what kind of worker am I? How do I like to use my time naturally? As opposed to trying to find a system and squeeze yourself into that.

Mike: Ultimately, it sounds like what you’re saying as an answer is also that you need to listen to that internal compass and how you’re actually feeling and what is actually drawing you towards it. I mean, I know I’m very guilty of falling into that optimization trap—I want to make the most of my time. And I know I have a lot of different things I wanna do, so I’m thinking, okay, I need to make sure I schedule everything perfectly. I need to make sure that I spend this much time on this thing and this much time on this thing.

And in the end, I realize what I’m doing is also essentially I’m guaranteeing that I don’t have any time for play and exploration and trying new things because I’ve managed my time so well that there is no time left to do anything new. Right? I’ve pre-optimized the whole week.

It’s not fun anymore. It’s almost ironic if the thing I’m looking for is fulfillment and joy. I’m guaranteeing that I can’t have that because I’ve pre-selected, I’ve made all the options a week in advance, and I’ve tried to go through that list and do all the things, and I get to the end of the week and I’m exhausted and I’m thinking, did I actually enjoy that? Did I leave any time for serendipity and play and what you said with the octopus?

Yeah. That feels a good mental model. Borrowing your metaphor, I also thought about the fact that octopuses have three hearts. And that almost feels how it is for me sometimes as a creative generalist. I have different interests I want to follow. And sometimes they’re competing in a way as well. Something is drawing my attention that isn’t logical, but I feel a pull in one direction and I, at the same time, feel a pull in another direction.

So I have two things that I really wanna spend my time on and they feel they’re competing a little bit.

Dave: Right. Yeah. And that’s where the metaphor kind of gets interesting. And I try not to take this whole thing too far—it can get kind of ridiculous. But I do think this creature has been around for, estimates say, three to 500 million years. It’s somehow managed to survive with all these unique characteristics—the three hearts, brain cells in its arms kind of thing. It is a different kind of thinking, right?

It just has a different kind of consciousness and a different kind of balance, even with this unusual appendage, heart, brain, tentacle situation—physical body situation. And so the hearts thing—the octopus has somehow figured out how to manage this. And I don’t know if it uses its heart as an emotional center or a place of passion or whatever, but for us as humans, I kind of like what you’re saying.

‘Cause in a way, if you think about it, we all have multiple passions. If you’re a parent, you love your kids. If you have a pet, you love your dog. If you have a job, you may or may not like your job, but people have things at work that they really like doing. You may have a girlfriend or a boyfriend that you really love, right?

In life in general, we all have multiple things that we really care about. And so, to think about it—okay, well I’m a complex creature. I’m a human being with multiple interests. I also can be passionate about more than one thing at a time. I may deploy that passion in sequential order, right?

You can’t walk your dog and be doing deep work, working on a mobile app or something at the same time. Physically, we can’t do certain things at the same time. But it doesn’t mean you can’t care about both things, right? You can care about things that are happening in the world. You can care about things that are happening in your personal life all at the same time. But we have to just think about how to deploy our energy.

And I wanna just tie this back to the calendar thing just a little bit. If you think about, where did the calendar come from or where did clocks for that matter come from? Right? And how did they become so prevalent? Earlier in the interview you kind of asked about where did this need come from to be this certain way? If you think about it, a lot of time and calendar things evolved the way they are because of work. A factory needed to—you had to punch in and punch out at a specific time so the employer would know how much to pay you.

You had to have a schedule because schools operated on a schedule. But a couple things come to mind. One is not all cultures are obsessive about time as we are, say in the US or in Germany. There are a lot of cultures where, in Latin America or Africa or even in Asia, where time is just much more fluid.

If you say we’re gonna have some kind of meeting at 10 o’clock, in some countries, everyone will be there at 10. In other countries, people will trickle in at 10:15, 10:20, 10:30, even 11, 11:30. They’ll just show up late and that’s okay. Culturally, that’s just understood that that’s how we think about time.

And so this obsession with it—sometimes we have to think about, is this always the way humans have lived and is this the way all humans across the globe live? And for the people that don’t live this way, what are they doing and are they okay? It seems to me that a lot of people are surviving just fine with no Pomodoro system or no time blocking or no obsessive calendar checking. I don’t wear a watch anymore.

I think you can live other ways. These are choices that we’re consciously making. We think we need a calendar because it’s on every computer and phone and everything for work. There’s calendars all over the place, but do you really have to use it? Do you have to use it in that way? Do you have to use it with those particular techniques? I would say a lot of it are artificially self-imposed things that we think we must do, but we really don’t have to. You can live a different way.

So I hope—I guess the theme’s kind of emerging in this conversation, which is I really hope people just kind of examine things that they’re doing in their life and ask hard questions about it. Where did this come from? Why am I doing it? Do other people live this way? Do I have to live this way? And is there another alternative? I hope this is kind of one thing that people start to take away from this thematically.

Mike: As you’ve started doing that work for yourself, did you feel pressured or questioned by the people around you, or did you have people being saying, man, what are you doing? This is crazy. You’re gonna do eight different things, you’re not gonna have a full-time job. Did you feel this pressure?

Dave: A little bit, but I also—I wasn’t telling a lot of people that that’s actually what I was trying to do until—so there was a period after the layoff in sabbatical where I was just kind of thinking, okay, I think I’m gonna kind of live this way, but I didn’t write about it or anything.

So I felt no pressure during that time. It was more just me finding myself—who am I gonna be in this season of life? And so there was this kind of incubation period, if you will, where I felt no pressure because I didn’t want outside inputs, honestly. I didn’t really ask people for advice. I didn’t seek out a coach. I think it was internal work that I was doing at the time.

But when I did start writing about it, I had some people asking or questioning the path—is this really feasible? But I had more people, I think more people were fascinated and interested and curious and wanting to understand, ’cause it was breaking something open for them as well, right? It was breaking a box that they had been living in and freeing people to think a different way about careers.

And so on balance, I had way more opening, positive interactions with people then closing—shutting down pressure, push me back to what I was doing before kind of conversation. So yeah, a little bit of both, but I don’t know, I’m getting to the age where I just don’t care what other people think. I’m thinking, okay, if you think it’s more secure to have a full-time corporate job, I just found out it’s not actually very secure. I just got laid off.

And in what was arguably a secure, good occupation. And a lot of people have been through that this past two or three years, right? Since the pandemic, there’s been thousands and tens of thousands, maybe hundreds of thousands of people have lost what was a formerly secure blanket and now it’s gone.

There’s different ways to think about security too. So, to answer your question, I mean, not that much. I actually didn’t get too much pressure from people to go back to what I was doing.

Mike: To be honest, I’ve had the same experience where when I first started actually doing the creative projects I wanted to, for a while there was a stage where I was thinking, I don’t have—I shouldn’t make time for those. I just focused on my career and climbing the ladder. And then when I got to a certain position, I thought, oh, okay, this obviously didn’t make me creatively fulfilled. I’m gonna now start doing those things. And I had some reservations about telling people, because I thought the reaction I would get was, I guess, my own internal voice.

I thought they would be saying, are you sure you can really handle doing multiple projects? Are you sure you wanna spend time doing that? Or the big judgment—why is he doing that thing? Why is he making a podcast? And the reaction I got actually, also talking to people in my day job, was almost always positive.

People were always saying, oh, that’s so cool. I want—I’ve been wanting to write a book for ages, or I have this art project I’ve been wanting to do. How do you find time? If anything, as you said, it seems people are opening up more about this kind of thing. There’s more and more discourse going on about how do you make that happen?

Which I think is really cool. The one thing I don’t know how to combat, and I wonder how you’ve done this, is resisting the urge to monetize everything.

Dave: Yeah. Well, so the need to make money obviously is there for everyone unless you’re independently wealthy or won the lottery or something. I don’t have enough money to retire, so I have to make money somehow. And so it’s always a pressure, but I also have lived eras of my life where money was just—it felt it was everything. I just need money. I need more money. I need more security for retirement. I just need to accumulate more wealth.

And when I look back on those seasons, they weren’t particularly happy seasons. I was making money and it was good, but I wasn’t feeling necessarily fulfilled. The things that made me happy during those eras were things outside of money. We could spend hours just talking about the topic of money itself. People have all kinds of views on it.

But I do think for people who are struggling with money, I do think it’s important to get a foundation of money somehow or another, whether that’s a full-time job or some tentacle that is a moneymaking path that seems more feasible than trying to make—sell art, for example, can be challenging to make a living. But selling social media posting services is arguably easier than selling paintings, for example.

I’m not saying it can’t be done, but if you’re in a situation where income is really tight, I would encourage people to start with just getting some security financially because there’s nothing more stressful and misery inducing than being broke—than having financial struggles.

I’ve had a couple periods in my life where I just was not totally broke, but had hundreds of dollars left in my bank account or something, and it was extremely stressful. It was hard to have hobbies or go play tennis with friends or do anything else when the electricity bill is coming due. I gotta find a way to pay this.

And so to have financial struggles I think impedes your ability to do other creative things. So that’s my first point—if you’re struggling financially, a lot of what we’re talking about with the octopus life is more—are higher up on Maslow’s hierarchy, I would argue. Self-fulfillment, finding things that are to help you self-actualize or that you enjoy.

So get those base levels of your pyramid in place first. But then if you have some amount of security and you’re interested in trying to turn passions into jobs, then I go back to the experimentation approach, where you could try little things to see if they make money. And be intentional about that, right? And don’t be ashamed of that. Say to yourself, I want to try to turn this into a revenue generating tentacle. And then you may have other tentacles that are just for fun.

I’ve picked up pickleball a little bit recently. I’m not making any money from pickleball. It’s just something that seems kind of interesting and fun and it’s social and stuff, but it’s not gonna make me any money. But I think of it kind of as a tentacle—it’s an interest area.

So I think the need to have money will drive a lot of your decisions. I mean, you have a job, for example, so you have a foundation which empowers your ability to explore some other non-money making things. And I think that’s kind of a nice balance, right? If you have a source of income and then you have some stuff that makes no money at all, but it brings you immense pleasure and joy to do. So if you can have those two things, that makes for a pretty decent life, right? You can cover your expenses, feel secure, but then have fun.

So yeah, it’s stuff to formalize it. I can’t give someone a formula or a system for it because the tentacle portfolio of our listeners is different for everybody. So what I’m trying to do—and this is one thing that I kind of get bugged about in the whole self-help coaching course industry—is that someone figured out how to do something and it worked for them with their personality and their resources, and then they try to turn around and sell it to other people who don’t have the same personality, don’t have the same resources, don’t have the same access to information or technology or whatever.

And then those people struggle to replicate whatever this person’s trying to promote. And so I think especially for octopus people, my encouragement is find your mix of things and decide which ones are gonna make money or not based on what abilities you have to make money. So don’t try to—you can’t just do brand consulting ’cause maybe you have no experience in brand. That’s one of my strong tentacles. But I can’t tell people, yeah, be a brand consultant. I made a good foundation for my octopus life. You can’t, unless you have that experience, you can’t do it, right?

So it’s not replicable. So you gotta figure out what works for you, and yeah, the commerce part’s always tough. Money’s always this challenge in the background.

Mike: I mean, to be honest, the reason I asked is because even thinking all the way back to the first question about Ikigai, I think for me I had some kind of default script running that said if you have a passion that feels like a creative passion—for example, the photography, I think when I first got really into it, there was this question of, oh, maybe this is the thing you should now try to monetize. And I’ve had that with almost every creative endeavor I picked up. I’m sure that says something about me and the scripts I’ve grown up with.

But I always had this voice in my head that as soon as I picked up a new thing, very quickly it became a question of, okay, you’re having fun with this. How can I find time to do more of this? Well, if I monetized it, maybe then I could justify spending more time doing it. And I think that can very quickly turn into a trap, right? You basically just build yourself a new job and then kill the passion for that thing, which yeah, I’m sure I’ve done and it sucks.

Dave: Yeah. I used to work in graphic design and I encountered a decent number of people who loved graphic design, but the job of graphic design ruined their interest in graphic design. And I do think this, especially with creative pursuits in particular, artistic pursuits—music, painting, dance, et cetera—people have natural interest in these things and passion and it brings a lot of joy, but the moment it becomes an occupation, it can get ruined in some way.

And so I think you have to be protective of the ones that you want to enjoy as a hobby. And just say to yourself, this is not a moneymaking tentacle. This one’s just for fun, and I’m just gonna let it be that and not try to make money off of it. And then you might actually enjoy it even more or do it even more because you’re free from the constraint of having to figure out how to sell it somehow.

I’ve seen this over and over in many people’s creative careers that the commerce part just ends up ruining the interest in it and even makes them leave the occupation or leave the activity altogether, which is unfortunate.

Mike: How conscious are you of the tentacle configuration you have at a given time? Do you intentionally think about the kind of energy that goes into each project and where you wanna put that energy? Because I could imagine that you could end up with two or three things going on at the same time which demand the same kind of energy—two or three things which are very artistic at the same time. I could imagine that might be hard to balance. Is that the case? Do you think about the configuration or you just go with your gut?

Dave: When I first started this journey, I thought about the configuration a lot more, but as it’s gone on, it’s become more organic and fluid. And I feel more free to kind of spend time on whatever I feel spending time on that day. I mean, I have constraints. I have a contract, for example, to do consulting. I can’t just push them off or ignore them. I have to deliver on certain things. So in that sense, I do have some structure or some areas where I can’t just let it go or let it slack.

But aside from that and the creative stuff, I allow it to be more fluid. I do think one of the things I’m kind of learning about this is just making myself less rigid in thinking and behavior, to de-rigidify my life, I guess is a good way to put it. And I found a lot of joy in that. Just the freedom and flexibility to kind of do what I want on a given hour or in a given afternoon has just been good.

I feel—I guess maybe some background is helpful here because maybe you relate, or some of your listeners relate that for most of my life I lived a pretty rigid life in the sense that things were very structured. I went through school, I went to university, I got a job. My life felt very structured and templatized in a way. And that became the default setting. So it is hard to escape that, but I found that I’m just as productive or just as interested, just as energized and just as engaged without having to think even too much about the octopus framework even.

It’s a springboard and it’s an organic thought framework that helps me kind of get free. It’s given me ideas on how to live, but I don’t adhere to it so strongly. I don’t have a map out on my wall of, here’s tentacle number one and number two and number three—which one am I gonna spend time on today? It’s not that rigid, right?

It’s in the back of my head, I guess. And it becomes—it comes to the fore when I talk to people about it, as I am now. But day to day I actually don’t think about it too much. It’s more about what you mentioned, kind of internal listening or looking within a little bit. It’s more that. It’s kind of this intuitive knowing that, okay, today I think there’s energy flowing towards this particular activity. So I’m gonna go with that flow and see where that leads for this afternoon.

Mike: Yeah, I mean, as you said, you have contracts and obligations, but ultimately it’s following your—I’m not feeling bad for that. If you wake up and you’re drawn in a particular direction, go in that direction and see what happens. Maybe tomorrow you wake up and you wanna go and do something else, but ultimately giving yourself time to be a little bit more free and experiment with stuff when you feel the urge to experiment with stuff.

Dave: Yeah, because people say inspiration is fungible—it can disappear or evaporate. If you feel inspired to do something, if you wait even an hour, that inspiration could disappear. If you have an idea, you should write it down. If you feel doing something, if you have time and capability at the moment, you should try to just look into whatever your heart is calling you to, because that feeling can disappear pretty quickly.

So yeah, I’ve been trying to do that more. I feel I’ve not been great at that. I often get distracted. I mean, this is a downside of being this kind of personality. You get distracted, right? So you just find shiny new object over here, and then you drop whatever you’re working on.

But I’ve been trying to be a little bit more conscious about that dynamic and put a little bit more energy and effort into things that feel inspiring in the moment. And reduce distractions, but also just pay attention more to what’s inspiring from the inside.

Mike: Yeah, that’s one of the things when I read about this kind of lifestyle, one of the things that kind of scared me a little bit was, well, doesn’t that mean I’m basically just never gonna achieve anything? I’m never gonna get anything done. And this is maybe my struggle again with photography, for example. I feel if I don’t have a long running project where I’m not sharing my work, what’s the point, right? It has to lead somewhere. I need to release or ship something. I don’t know. Maybe that’s, again, just a personal script to break out of a little bit.

I mean, also then the counter to that is that I recognize that that also can stop you from actually just having fun and playing with stuff. Maybe just pick up the rock and then drop it and go do something else. That’s fine. That depends what success is, right?

Dave: Right. Yeah. It depends what your definition of success is and what you’re trying to accomplish in life. But I’ve also found that if you think too rigidly about it and try to map out, for example, what you see happening, that may or may not materialize. But there are some benefits to just being more fluid.

People have done sort of experiments on—if you give this group of kids no—there’s kind of an end goal, but you give them no instruction for how to do it, and then you give this other group of kids the same end goal, but you give them instructions—the kids in this group come up with more creative solutions than the kids in this group. Things where serendipity, unforeseen happenstance and discovery in the process can open up new things for you that you can’t preconceive.

And so I do think that that component of overplanning can be dangerous sometimes, or overthinking things before you do them can be dangerous. But to your point about not accomplishing anything, so this is a definite risk of the octopus life. Let’s just take extremes, for example. There are, say, professional athletes. So I play tennis—Roger Federer is one of my favorite athletes. He retired recently, but he dedicated his entire—the first 40 years of his life to just playing tennis.

I mean, he did other things. But the vast majority of his time and efforts were dedicated to playing tennis. And because of that, he became the best in the world. And while people will argue with me if he’s the best with Novak—I don’t know if you watched tennis, but at one point, he was arguably the best tennis player in the world and he became that because he did only one thing, right?

So if you wanna have an extreme sense of accomplishment, then it does absolutely make sense to dedicate yourself to something—to some one thing or narrow set of things. But if you also, at the other extreme, look at someone like Leonardo da Vinci, who is also extremely accomplished, famous, the best in the world at whatever he was doing maybe at the moment, but he had a dozen interests.

Now, many of those tentacles didn’t make him famous. They were just things he may have done for a day or a month or even a year that went nowhere, didn’t turn into anything notable. But because he’d tried so many things, he actually did end up accomplishing a lot of interesting things too.

Maybe he wasn’t the best architect in the world, or maybe he wasn’t the best artist in the world, but he was pretty darn good at a lot of things, and that made him a really interesting individual historically. So I guess I can’t prescribe that you’ll be able to accomplish anything noteworthy in an octopus life. You may very well toil in obscurity, make a living for yourself and never be famous, never be known for anything. Twenty years after I die, no one will even remember who I was. And that’s okay. I just feel I’m doing the best I can. I’m living the best life that I know how to live and enjoying it as best I can.

Trying to find as much meaning as I can out of this era of life. And if it turns into something that I can call a significant accomplishment, well then great. But if it just turns into a lot of minor accomplishments, then that’s okay too. I think I’ll be okay with that because I at least was true to myself.

I was true to who I am, true to how I’m wired, true to how God or the universe made me. I’m just being my true, pure person and activating the gifts that I have, deploying the mix of interest that I have. And I think that will prove valuable to someone somewhere in the world. I don’t exactly know how, but it doesn’t have to—I don’t have to win Wimbledon at this point.

I’m pretty sure I’m not gonna be the best in the world at anything. There will not be a Wikipedia article about me after I die. I’m pretty sure that’s gonna be the case. And I’m okay with that. Not everyone can be the best at something. Not everyone can be notable. You don’t have to have that as a goal to have a good life, I guess, is what I’m trying to say.

Mike: I think, again, it can be freeing to realize you don’t have to be the best at everything and dedicate your life to everything. I mean, I think that’s also the cool thing about being a generalist and being into many hobbies. I used to feel this guilt in a way where I almost felt apologetic. I didn’t wanna tell people that I tried so many different hobbies because I think that there would be judgment about, what, you did that for two months and then never again? That’s weird.

Yeah, but I mean, it’s cool. I’m only gonna be here once. Why wouldn’t I wanna try out playing the drums for two weeks and then the guitar for a month and then I wanna go and learn how to ride a unicycle for six months. Because for some reason I got really obsessed with that thing. I mean, why not play around and just try a bunch of stuff out? It doesn’t really matter. The accomplishment there is that you got to try a bunch of stuff out.

Dave: Yeah. ‘Cause for our personality type, I think the joy is in the discovery, in the learning, the attempt to master something, even if you don’t achieve world class proficiency. The fun is in attempting world class proficiency, even if you know you’re not gonna get there. You mentioned a unicycle—just trying it is fun for us, right? The attempt is the joy.

And so if you attach an outcome to that, it can ruin the joy of the process. And so I think people are—have drilled into them this idea that every endeavor you do must lead to some place, some noteworthy accomplishment place or make money, for example, as we were talking about before. But that kind of thinking ruins the process. There’s joy in the journey.

You can have fun and richness and life in doing something even for a month and then quit. I have a draft in Substack about it being okay to quit. And I tell this story—when I was in high school, I tried out for the football team because most of my friends were on the football team. I’m not a big guy. I am 130 pounds. I’m skinny. I don’t have a football body at all, but I thought, it’ll be fun. I know how to play football just from playing in the park with friends. Let me try out for this.

So I tried out for football and I enjoyed it for a week, and then I started to not enjoy it. And so the way it worked in my high school, the football season began at the beginning of the school year, but to join the team, I think it was a month before school started, you started practicing. You had to go during the summer and start practicing on the football team, start lifting weights, start getting in shape.

And so I joined the football team—it’s maybe a week and a half into the season. School hasn’t even started. The season hasn’t even started. And then I decided I want to quit. And so I go into the locker room and I was nervous about this too. I felt, oh, I’m a quitter. We haven’t even played a single game and I’m quitting. And my friend, we were in the locker room, people were putting stuff into their lockers. I was taking my stuff out of my locker. And one of my friends was asking, what are you doing? Are you quitting? And I said, yeah, I’m quitting.

So I go to the coach who has this separate office in a cage. And I say, can I talk to you for a couple minutes? I don’t know this guy at all. He’s a teacher at this school, but I was never in a class with him. So I don’t know him at all. He doesn’t know me. And I say, coach, can I talk to you for a minute? And he says, sure, sit down. And I don’t even know if he knew my name, but I was thinking, I don’t think I wanna play football anymore.

And he was kind of disappointed. He was, oh, why? And I said, it’s just not fun. It was kind of fun at the beginning, but I don’t really—I don’t really like all the stuff we have to do. And I think I’m more of a tennis guy. Even back then I knew I liked tennis.

And I could tell he wasn’t mad at all and he didn’t give me any lecture about being a quitter. ‘Cause he could see that football did not match who I was. And he was, okay, that’s fine Dave. You have other things you can do. Just put all your stuff over there and enjoy your summer before school starts. And that was the end of it.

And in one sense, I felt bad ’cause I did feel that natural pressure from society—you’re a quitter. But on the other hand, I felt I had some fun. I had put on the pads, we had some scrimmages. I played with my friends. I could say I was on the team for two weeks and then it ended and I was upset about it maybe for a day. And then I was—I went on with my life and I just started doing other things. And that’s okay.

I feel life is full of quitting if you think about it. We quit all kinds of things all the time, whether it’s hobbies or—and eventually we’re all gonna quit life. We’re just all gonna die and you’ll have quit your entire life. So it’s okay to quit things. I think we need to destigmatize quitting. I mean, if you think about it with kids, I think good parents let their kids quit all the time because they want them to explore a wide variety of things.

If you send your kid to band and they hate it after two weeks, you’re not gonna force them—oh, you gotta stay in band for the whole year and then you can quit. I mean, some parents do that, but if a kid expressed interest in something else, good parents, I feel, say, oh yeah, go try that. Try this, try that. And they want kids to have a sense of self discovery and have a sense of agency and ownership and what they do.

The worst kind of mental space you can get into, which I think continues often into college, is you feel pressure from somewhere or someone to do a certain thing that does not align with who you are. It just doesn’t match your personality or interests. And that’s the worst kind of trap. And that can extend into careers too, where people just feel, I have to be a lawyer. My dad’s a lawyer. Everyone in my family’s a lawyer. I have to be a lawyer. And then they get a lawyer job and they just hate it.

And then you feel trapped because you never had a chance to quit. I wish after freshman year, I knew I wasn’t gonna be a lawyer. I should have quit. It’s much harder to quit something when you’ve invested 20 years in it than it is after you invested two months. So I kind of feel quitting is a good filter for discovery.

It helps you get to know yourself better. It helps—it also helps you know what you don’t want. There’s a lot of these things that try to help you figure out what you should do or your passion or whatever, but a lot of it involves sitting around thinking about it. And I would say, well, another way to discover your passion is to discover what you don’t like. And the only way to discover what you don’t like is by quitting a lot of things.

So go ahead and quit. It’ll give you a data point. Okay, look, I don’t like that. Why don’t I like that? There’s something about it I didn’t like. I didn’t like the rigidity of it, or I didn’t like what was required of me. Or I just don’t think that way. Those things help you get to know yourself better as well. So I encourage people to try and quit all kinds of things. Do it as much as you want. It’s good for you.

Mike: It feels often the unsaid expectation is if you quit, you fail. And so you have to keep going because if you quit then you look a failure. Oh, you’re just backing out. You don’t have the strength to continue and all that kind of hustle territory, right? It’s feel the pain and do it. Delay happiness, delay joy. Keep going.

I love this statistic and I don’t know how true it is—they say the second week of January is where most people quit their New Year’s resolution. And I read about that and I Googled it and I was a bit sad because every single article I could find about it, it was all quite negative. It was, don’t be someone who quits on Quitters Day.

And in the end, I basically wrote an article that was, I hope you quit something today. Happy Quitters Day. Let’s turn this into a thing. I’m trying to make this a thing. So if anyone is listening and wants to make this into a thing, I think we should turn it into a day of joy—International Quitters Day. Write down all the things that are not making you happy in your life, that you feel there’s a sunken cost or you’re obligated to do it and it’s not bringing you joy. And if you can just cross out one of those things, just quit it and just be so happy that you quit it because it’s sad to keep doing things just because of some—just because you feel you have to or because there’s some should somewhere in your head that says you have to continue doing this thing.

You also wrote an interesting article about how often people start with why, and maybe it would be a better thing instead to say why not?

Dave: Yeah. So Simon Sinek has this book that says, start with why, where I think I kind of got the first concept from. But I was also thinking, this sort of relates to the quitting thing—why not? Why not try something? Why not let it be you?

And I think trying to find your why—the reason there’s so many books about this is because it’s hard to do. It’s hard to envision your life’s calling. It’s hard to envision your why. It’s hard to find your purpose in life by just sitting around and thinking about it. And a better way to discover those things is by a random variety of attempts at different things.

And then you can discover—you might discover your why by figuring out a lot of why nots. You do a lot of things. You experiment a lot, you explore with your tentacles, and then you may discover a why that you wouldn’t have discovered if you sat around trying to discover your why.

So I to try to have people just think about, well, why not? Why couldn’t I do something? Why can’t I have a weird career experiment? What’s stopping me from doing X, Y, and Z? And often, there’s nothing really stopping you. It’s just your imagination or your societal pressure that you’re inventing for yourself that’s stopping people from trying things.

And I get the whole worry or shame or that you’re gonna try some why not thing, and then it doesn’t work out and then it looks a failure, or it looks—I’ll just share a personal example. So when I started consulting, when I was working in corporate, I would interview people for jobs who were trying to find a job with the company I was working at. And I’d look at some of their resumes and some people would have on their—some employment at jobs. And then there’d be a year of consulting and then they’re applying for this job.

And in my head, unfairly, I think I would kind of judge them. Oh, did your consulting fail? Is that why you’re applying for a job? But then I found myself in that boat and I was, oh crap. ‘Cause I was applying for—when I first got laid off, I was applying for jobs. I was still in that corporate mindset—I need to find a new job. And then I started consulting and I was still interviewing for jobs. And it was in the top of my head—people must think I’m a failure because I have on my LinkedIn I’m doing InSprint Consulting.

And it hasn’t been a smashing success, but I wouldn’t say it’s been a failure either. It’s been okay. I’ve made a sustainable—not as much money as I did in corporate, but—I don’t know. I get the embarrassment thing. There’s all kinds of things, particularly around career where people worry about how they’re perceived.

And there’s some validity to this, especially if you’re gonna stay in a traditional employment path, right? You do have to think about your resume or think about how things look professionally as you apply for jobs. But I also feel if you’re gonna break off this path, you could ask yourself, why not do something different or at least attempt something different, or even while I have a job, do something weird on the side?

Why not? There’s no harm in trying. And the worst thing is getting to the end of your life with a long list of things that you had ideas to do or interest in doing, and then never having done any of them. I feel that’s gonna be a huge regret for a lot of people. And it’s a regret—I actually do already, I have some regrets. I had opportunities to do certain things at a certain age and I didn’t take them and I regret them.

But I do just feel, yeah, why not at least try some of them? You don’t have to do everything on your list, but just do at least one or two and see what happens. There’s no harm in it. And if you do feel embarrassed, if it’s a professional thing and you feel embarrassed, then just don’t post it on social media. You don’t have to tell anyone you failed.

You can keep it to yourself. Then you won’t get any grief from anybody if no one knows what happened. There’s a lot of things you can do kind of experimentally in private nowadays. It doesn’t all have to be on the internet. So yeah, I just think why not try?

Mike: There’s a really good Stephen Butler quote, which I love, and it’s something most good things are on the other side of embarrassment. Most interesting things that you can do, you have to feel the cringe feeling and then go and do the thing anyway. ‘Cause it’s so easy to talk yourself outta stuff because of the fear about what other people are gonna think or what is it gonna look if I quit. Or as you said, well, what if I post about this or I tell people about it and then I change my mind?

Or what’s it gonna look on my CV if I take a career break for six months? So many things at the root of it, the reason of why should I not do this thing is because you have a fear of embarrassment or cringe or judgment, and it’s just such a crappy reason not to do it. Just go do it.

Yeah. And I had that with this podcast. I was so worried about what people were gonna think of me genuinely. I don’t know why. The real answer to that is actually no one really cares that much, by the way. You care a hundred million times more than anyone else cares about what you’re doing. It’s so freeing once you realize that you can just go do anything.

Dave: Yeah. And especially bad in the era of social media where people are sitting on their keyboard behind the privacy of their screen and they can criticize you all day. Many years ago, I tried to learn skateboarding and I made a video about it and I put it on YouTube. I was a total beginner. Well, I think when I was a kid I may have tried to ride one, but this is as an adult. I bought this longboard and I made a video about it.

And of course, some skater kid from who knows where has to comment on my video, basically—you suck at skateboarding. I’m, yeah, ’cause I’m a beginner. I just started so of course I stink at it. But it just kind of—it—I could see why people don’t wanna do things anymore is ’cause you just receive so much hate mail over the internet and trolling and it’s just a sad dynamic that I see in our social media landscape that is just so easy to criticize things.

And I mean, I’m guilty of it too. Sometimes I’ve criticized somebody on the internet for something they did or I thought was wrong, but I try to avoid that. I try not to do that. I hardly ever do it, but I have long ago gotten in fight arguments with people on the internet and just realized, they’re—it’s not fruitful. It doesn’t help anyone. It doesn’t help you because someday you’re gonna be the one that has to put something out there.

And is that the kind of hate that you wanna receive? Is that the kind of response you wanna get is to have people—you attempt some dream and people just step all over it, total strangers from across the world step on it and crush your dreams. Is that what you want? So I just—I wish people would be more civil on the internet.

And I think it would help people be more free to experiment with things. But the good thing is you don’t have to tell anyone. As I said, you don’t have to post about it. So I do things—I have personal projects or whatever. I haven’t said anything about them on the internet just yet ’cause they’re so nascent. I wanna protect them from critique or being stepped on. So yeah, it is a sad dynamic though.

Mike: Do you feel more courageous or less worries now than you did before about putting stuff out there and even publicly announcing projects and just doing stuff?

Dave: More courageous than before. But when I first started, even when I first started writing my Substack, I was really afraid. I’m not a very public person on the internet. I don’t use social media that much. And so Substack was, I think some of the most personal things I’ve shared on the internet.

And I have a couple posts during my sabbatical that I put up that I actually took down. Not because I was embarrassed of them, but I just felt I shared maybe a little bit more than I wanted to. People don’t need to know everything about your thought process in life. So it was a gradual process of feeling more comfortable about sharing things. It took a while to kind of get comfortable with it.

But now I still am cautious. I still am somewhat guarded just in general. Not necessarily because of trolls or whatever, but more because I just don’t feel the need to put every last detail on the internet somewhere. It’s not fun for me. I don’t find it that fulfilling.

And I also just, yeah, part of me doesn’t want the critique either or the questions. ‘Cause some of the things I’m doing are kind of odd in the work world in particular. I do think I’ll probably—we talked about before—I’ll probably get more support than hate, but I’m still cautious about it.

I’m just not that public a person. Even doing these podcasts, I did my first podcast to talk about octopus life last year, and then I did a second one. And even that I was really nervous at first. I was thinking to myself, okay, I have to be careful what I say. It wasn’t live, but I was kind of self-censoring myself a lot during that very first interview. I was thinking, okay, what do I wanna share about this? Or what do I not wanna share about what I’m doing?

But over time I’ve become more comfortable with it. I do think if you wanna promote anything—so that’s the balance, right? I have projects that need promotion in order to succeed. So I do have to be public about that and I’m getting more comfortable with that kind of thing. Yeah. But it’s a balance and I definitely kind of protect some information about myself. Yeah. Not to be secretive, but it’s just—you don’t have to know. Why do you have to know? Why does the internet have to know about all this?

Mike: Yeah. I had this conversation with a friend where I said, oh, I’m still kind of getting nervous before I do episodes. And I’m nervous to put some stuff online sometimes—it feels vulnerable. I’m trying to work through that. And the question they asked me was so good because they were, would you want to be the kind of person that didn’t feel nervous at all?

Would that be a good sign that you are so confident in everything you say that you have no worries about what people think of you and how you act? It’s freeing to realize that, no, I don’t think I would want to be that person as well. It’s probably good to have some sense of balance and to think about your impact of your actions and your words and what you’re sharing. Probably makes sense that you think about it a little bit.

Dave: Yeah, it shows a sense of conscientiousness, right? That you are aware of your role in the world and what putting stuff out there could do for people. And you just want that to be a good experience, right? You don’t wanna put crap or nonsense or negative things into the world.

So I think it’s a good trait. I mean, it can be debilitating if it goes too far so much that you don’t even do the podcast when maybe you should, but I think there’s a healthy amount of self regard and self-editing, of just care and tact about what you put on the internet.

So I think it’s a good thing. And even just talking to you, I just feel you’re a thoughtful person. You obviously care about what you’re doing, you wanna be conscientious about it. And I think those come across as good traits as far as I’m concerned.

Mike: I hope so. And I think the nice feeling on the internet as well is—I’ve heard of it described as the serendipity machine because, I mean we were talking about this right before we started recording, right? Without Substack and stumbling into each other’s work and then reaching out by email, those conversations wouldn’t happen. I wouldn’t have had the pleasure of meeting you and chatting with you.

And there are so many other connections. And another thing we mentioned beforehand was if you’re in a traditional career and no one’s really talking about all of the other creative things you could be doing in your time, and you’re thinking, okay, well I’m only exposed to this traditional lifestyle where I have a job and then I focus on climbing the ladder and that’s all I do.

If you’re not exposed to more ideas and to more ways of living and to people doing different stuff, it’s hard to even realize that that’s an option, right? And I still think it’s something that I’m trying to figure out—how do you find mentors and peers outside of the traditional structure?

But I do think the internet does play—there are lots of negative aspects of it, especially with modern social media. There’s lot of stuff I don’t like about it, but I’m really trying to consciously use it in ways to make new connections and find people who are doing interesting stuff. Yeah. I dunno how you do that personally. I think it’s a hard challenge sometimes.

Dave: Yeah, I mean, it’s been interesting since writing about this. I’ve had multiple people reach out and ask just to have a call—if I would chat with them and stuff. And I’ve taken most people up on that, and it’s been great.

When I had a corporate job, no one was asking me to have a call. I didn’t get—the only thing I got on LinkedIn was people trying to sell me something. But after writing about this on Substack and LinkedIn, I started getting inquiries—oh, this is kind of interesting what—I resonate with something you wrote. Can we have a chat?

And it’s been great. I’ve talked to people from all over the world about the—I mean, not a lot, less than a dozen people, but still, it’s just some interesting connections that I never would’ve met or interacted with before, who seemed genuinely great people to know. And I’m always happy for those conversations. They always leave me feeling kind of enriched myself.

And so yeah, I haven’t necessarily gone out seeking mentors per se because I haven’t found—met that many people doing what we’re trying to do. So it feels a lot of carving my own path. But thematically back to what we were talking about before, I also feel the people that have tried to formalize this too much, it just doesn’t fit.

I’ve kind of investigated what are other people saying about portfolio careers, for example, but I just haven’t—I found good inputs, other people that are doing it. But it’s hard to find someone who’s successfully—it’s hard to find someone who’s successfully done it. There are a lot of people talking about it, but I don’t know how many people are actually doing it.

Back to my gripe—coaches and people putting out courses for things that they—it’s kind of, well, I didn’t accomplish this, but I learned a lot along the way, so I’m gonna make a course for other people to not fail at it too. But anyway, I feel there’s very few—there’s a handful of people that are actually doing it and they have varying degrees of publicness about what they’re doing.

But I just haven’t found a really strong mentor for the exact way that I wanna do it. And so it has been a challenge. I do feel I’m kind of carving my own path. I mean, not that portfolio career is—I didn’t invent that idea. Charles Handy invented the idea in the eighties. So it’s not this is something I’ve created and must trailblaze. I must be the first person to succeed at this kind of thing. I don’t see it that way.

I’m walking on a trail that a lot of people have attempted before, but it’s just in the modern iteration of it, it does seem there’s very few people actually doing it. And I can’t even say—I’ll just speak frankly—I’m writing a book about this and some people have asked, where’s your book? You were talking about a book a year and a half ago. And I’m, I haven’t finished the book because I haven’t succeeded at this to my satisfaction such that I feel I have any authority to write a book to tell you how to do it.

I feel I have a half—two thirds of the book can be written, but the remaining third is just—I’m living the remaining third as we speak. So I cannot in good conscience make a course about how to have an octopus portfolio career when I have not succeeded at it myself.

And other people would argue—I’ll go back to tennis. There are some tennis coaches who are coaching tennis players, and those coaches have never won a Grand Slam tournament in their life, but they’re coaching guys, or women who are trying to win a grand slam. So you could say, well, you don’t have to succeed at everything to be a great coach. And arguably there’s a lot of great coaches who are better at coaching than they are at playing. And there’s one guy in particular who’s kind of famous for this.

But anyway, I feel there’s a dearth of mentors in this space. Eventually, if I feel comfortable that I have achieved the octopus life, whatever that means for me, and write the book, I may coach people on it if that’s what people come to me for. But in the meantime, I’m actually more interested in people who are in the trenches right now, just you, who have this concept in their head of how they’d like to live and work, but have not quite materialized it, but are wrestling through the issues to get there.

I feel those are the people I really wanna find—that’s my tribe right now. Or other people who have a vision for this kind of life and are trying to make that happen. So I’ve been thinking about making a community for that. Not a community where, hey, I have eight videos for you to watch and then you can comment on them.

Mike: That’s $5,000.

Dave: Yeah. And for a limited time it’s only $2,000 ’cause normal price is $7,000. I’m thinking about making a community of octopus life strugglers. You are in the same boat as me and let’s share what we’re doing to figure out how to do this. ‘Cause I think that’s—I actually think that’s more fun than I’m the guru. I have a formula. Try to adapt your life to my formula. And I hope you’ll succeed. You’ll likely fail. But that’s the promise, the false promise that I feel is often held out.

And so what’s more interesting to me are dynamic individuals who are saying, I wanna try this too. I figured a few things out that you may not know about that might be helpful, but let’s share what those are and then we can do this together, and then hopefully some of us achieve this, and then more people can see that it’s doable, right?

That’s kind of my—if I do anything along the coaching community course line, that’s what I would probably do. Not record videos of myself talking about how I think this is gonna go before it’s actually gone that way. I just have a credibility issue with that—personal credibility issue with that for myself. So—

Mike: I hope you do it. And when you do, you can send me a link and I’ll put it in the show notes for people to sign up to the community. I’m curious, how would you know that you were accomplished enough living the octopus life to then finally say, now I have the authority to write the book?

Dave: Hmm, that’s a good question. I haven’t really thought about what success looks like, ’cause I’ve been on this meandering, organic path of exploration. But I guess one thing would be financial security, obviously, as we talked about, right? If I can only make $8,000 trying this, then that’s not gonna work. I need this to be my career. I need this to work as a functioning occupation. So one would be a monetary amount.

And I won’t say what that is, but I don’t know. It has to be above a living wage. It can’t be poverty level either. To me, ramen FIRE level would not be considered a success. It has to be enough to cover all my expenses and then some, and feel I’m saving for retirement and it’s a viable, feasible way to work.

So that’s one criteria. I guess the second one would be, it can’t be all one thing. Obviously, if I do something, put out a product or whatever, and it’s one tentacle and it makes me $500,000 or something, but it’s only one thing, then that’s not a success either, because then that’s not an octopus life. That’s just going back to single-minded. What’s your one thing kind of career?

So that wouldn’t be a success either. So it has to be at least two, but ideally three or more things that are all sort of operational and functional and they’re working in the world some way. They don’t all have to make money as we talked about, but it has to be somehow actuated to some degree in the world.

So I think that mix of things—it has to make me enough money to call this a true career. It has to be more than one thing and it has to actuate somehow in the real world to my satisfaction. I feel I could say, okay, I feel I’ve accomplished this or done it to a meaningful way where I could credibly say this is what my octopus career looks like.

Mike: I’m talking about resources that you’re considering to make or not make yet. And the classic question I have at the end of the show is also what books or recommendations do you have for other people to check out?

Dave: Yeah. Well before we start talking, Paul Millerd’s Pathless Path, I read that during my sabbatical and it was terrific. What I liked about his book was it was exactly kind of what we were just talking about. He shared a lot of his journey. It was an incomplete journey, but he had figured out some things along the way and it was inspirational to me to think, oh, well here’s a person who was on the traditional path and he broke off of it and went and moved to a different country and started a new life and is making it work.

And so if he can do it, someone like me, I think I could do it too. So that was really inspirational. The other book is called The Great Work of Your Life by Stephen Cope. It’s not autobiographical. And it’s a little bit on the spiritual side. He uses the Bhagavad Gita as a source text to help people figure out kind of what’s your role in the world? Or your calling or mission in the world?

And so it’s not an overly spiritual book, so I don’t wanna scare people away with that. He just uses that kind of as a springboard to talk about calling. ‘Cause one of the characters in the story is kinda wrestling with what they should do. And I found that to be really good. I wouldn’t recommend that for young people or new college grads. It’s a little bit deeper, more for mid-career people. I think it would be a really interesting read.

So those two books were pretty influential on me in this journey. And then for generalists obviously Range by David Epstein is a good book. And I’m reading 4,000 Weeks by Oliver Burkeman right now, which is—

Mike: I love that book.

Dave: Yeah, terrific meditation on time in general. So yeah, that’s kind of what I’ve been recommending to people lately.

Mike: Nice. As always, I have more reading to do. And I agree in terms of Pathless Path, I think many people, that was quite a mind blowing book, at least for me. To see someone who’s actually on that path and figuring out and writing about it and thinking about it so openly, and to see that there are possibilities for me at least, even if I haven’t quite achieved the perfect layout, whatever that looks. I think it was very instrumental in changing my thinking as well.

Dave: Yeah. Totally. If I write—when I finish my book, I hope it has the same kind of effect that Paul’s book had. It tangentially feels kind of akin to what he’s written. I mean, obviously mine would be through the octopus sort of construct, but I would love for people to read my book and feel it just broke open something for them. Just got them out of a box they were stuck in and helped them see that other ways of living are possible and other ways of working are possible, and you can embrace more your true self.

So yeah, it was a great book and I was glad to meet him too. It’s always fun when you can meet an author and experience them in person, ask them questions and stuff. So yeah, it was really—I’m really glad I got a chance to meet him.

Mike: My secret goal now I’m gonna write it down, is get Dave back on the podcast once he’s released his book.

Dave: Yeah, sure. I would love to come back. It’s been a fun conversation. I’d love to do a part two.

Mike: And for the people who make it all the way to the end, I always to ask if you have one key takeaway that you’d people to go away and think about once the show finishes.

Dave: Yeah, I mean, I guess it’s related to what I just said—mostly to think that there’s other ways to live, that we have so many default settings that have been implanted in us by education system, by government, by our parents that are modifiable and do not need to be there.

You can carve a different path. You don’t have to stay on that set trajectory. There are other ways to live. And sometimes it just takes some intentional doing and self work and pondering to figure out what things are keeping you down, and then have the courage and bravery to attempt something new.

I hope that’s the main thing that people take away from my story.

Mike: Amazing. Dave, thanks so much for coming on the show.

Dave: Yeah, thanks for having me. It’s been great.