Learning, Self-Employment & Making Business More Human (Mike Tannenbaum)

[01:39] Paul: Today I'm talking with Mike Tannenbaum. He helps people rethink, reimagine, and redesign how we live, work, and connect as modern humans. Definitely a mission close to what I'm pretty passionate about as well. Welcome to the podcast, Mike.

[02:00] Mike Tannenbaum: Oh, thanks so much for having me.

[02:02] Paul: So I want to dive in here. I, you have this on your LinkedIn profile, so I'm assuming it's fair game, but I want to start with the TI-83 and how you started as an entrepreneur in 7th grade.

[02:16] Mike Tannenbaum: I have that on my LinkedIn. Wow, I haven't seen that part in a while. I always created things. I was always head in the clouds making things. TI-83 is kind of how I learned to code and how I learned— I didn't even know it was coding. It wasn't like a thing.

It was just I had this tool I understood what technology was capable of and I wanted to find a way to keep track of my grades that wasn't on pen and paper and Excel.

[02:54] Paul: In 7th grade, you were tracking your grades already?

[02:57] Mike Tannenbaum: Yeah, they weren't really good grades, but I was tracking them anyway. So yeah, it was— I mean, honestly, I made a program called Grade Keeper and it was a thing that Everybody else was passing around the Snake game and the Jumper game, but I ended up passing around a Gradekeeper program.

[03:17] Paul: You charged people for this?

[03:19] Mike Tannenbaum: No, I did not charge people. In hindsight, I probably should have, but I was a little— That was the early days of my making money off of things that I did. That's kind of when it started.

[03:33] Paul: Awesome.

[03:33] Mike Tannenbaum: I would also sell bootleg CDs, but that's a— Conversation for another time.

[03:37] Paul: No, we can dive into that. I mean, what are some of the other things when you were younger you did either to make money or entrepreneurial or creating things?

[03:48] Mike Tannenbaum: I got a job in— I guess going all the way back, it was mowing lawns. It was tech support. It was a lot of tech support. I would sell custom computers. Most people didn't need a custom computer, so I would sell them just cheap computers that were custom to neighbors and friends and family. A friend of mine and I adopted eBay early on, so we would sell stuff that our parents had around the house or that we had around the house on eBay.

We sold Pokémon cards in little packs and we sold hundreds of them as a way to bring in money so that we could build our own fancier custom computers because you can sense the theme of nerdy childhood here.

[04:30] Paul: Yeah. You described yourself as an impressionable nerd. Yeah. What does that phrase mean to you?

[04:39] Mike Tannenbaum: I'm 32, for some context for aging there. So I grew up on the internet for the most part. I think I was an early adopter of people our age. Right. But I was way beyond AIM. Most people were— chatrooming and so was I, but I was also building—

[05:00] Paul: Proggies perhaps?

[05:01] Mike Tannenbaum: Yeah, and proggies and I was crashing people's AIM and I was building websites. For me, it was exploring interest. There wasn't a class that taught that in school. I never really learned how to learn until I kind of finished my college and at that point, I'm like, "Wow." There's so much knowledge I want to soak up. 10 years after that, I've just been doing that relentlessly. Back in the day, I was a nerd because it was video games, it was building computers, it was building things on the internet, so it was a lot of technology.

The impressionable part was whatever's out there, it's everything that I experienced through life imprints me in some way, shape, or form, whether I choose to let it or I don't. Some things just happen. So seeing all of those communities online, being a part of those communities, learning how to build relationships across the internet, which I ended up doing in part of my career in business development. But it was very— for me, it was the early days of the internet and it was a way to meet people and talk about other nerdy things.

[06:14] Paul: Yeah, that definitely resonates with me as well. I never really reflected back until I was a little older that I would go home from work, or not work, but school, and just spend like hours on the computer. And I think one, I'm just grateful to my parents that they like had that technology, and two, just let me do it for hours on end, not knowing what I was doing.

[06:36] Mike Tannenbaum: They had no idea what was going on.

[06:39] Paul: But yeah, I was trying to create programs, write websites, and when I reflect back, it really resonates with the path I'm on now, which is just constant and continuous learning and needing to solve problems within things I go after. So, I mean, you said you didn't learn how to learn after college, but I mean, to build a computer at that age, you did have skills and talent and knowledge.

[07:06] Mike Tannenbaum: Yeah, I think it's very— maybe it's meta-learning or maybe it's just mindfulness and awareness. I wasn't aware of my desire to learn and my ability to learn. And I was put into the gifted and the challenge and the advanced programs and skipping math here and there. And I never understood why because I was insecure and I didn't think it was right for me to be like— I didn't understand why my grades did not reflect But, that's because I was being tested. I'm going to launch into a diatribe here, but we were being tested based on a system that isn't accurate. Everyone learns differently and every bio-individuality, everybody's body is different.

So, the system of schooling that I presume you and I grew up in, you in Connecticut, me in Philly in the suburbs close to the city. It's everyone's the same and you're measured to the scores and you have to achieve the same things or you don't get the same opportunities. So for me about learning, I was doing it, I was doing a ton of it and I wish that, I mean I'm happy with the way that my life has gone. It's been great, but like I occasionally have wondered what would have happened if someone actually, helped me and cultivated my desire to learn about technology and computers and systems at that point, as instead of telling me I have to learn about like, in 1492, Columbus sailed the ocean blue. Like, what would have— what would have— what opportunities would that have opened up for me, I guess?

[08:48] Paul: Yeah, I, I find it fascinating too. I think I reflect back, and for me, I was actually good at the standard system. So in some ways, I, I also was blinded to the fact that I kind of thought I was learning. Um, but now I kind of reflect back and a lot of that learning was happening in outside of the school or outside of the standard curriculum. And I think like me, I had to figure out that learning was a different way of engaging with ideas, practicing, putting things out into the world. What have you found now, like if you compare it now, how you learn and how you proactively go about that, even compared to early in your career, how are you thinking about it different?

[09:36] Mike Tannenbaum: Sure. It's a great question. I'm aware of my relentless pursuit for knowledge. I'm aware of the number of books that I read.

[09:53] Paul: How many books do you read?

[09:55] Mike Tannenbaum: I actually— so it's funny, I say I'm aware of it. I'm aware that I read a lot of books, that I'm constantly reading multiple books through and through, but I actually have no idea the number of books I read because I'm just always reading books. Everybody at the end of the year is like, "Well, I read 60 books this year. Next year I'm going to try for 75." I have no idea. I'm a slow reader, but I'm always reading. And now I'd like to implement a system where I read the book, I make my notes.

I read a lot of nonfiction, and I read fiction at night to fall asleep, but most of the time I'm reading about the problems of the system, whatever. Pick a system, any system, I'm reading about the problems of it, or the future potential problems of it. And I make a lot of margin notes, and I make a lot of underlinings, and I love physical books because of that ability. And what I don't do is revisit those books and those notes. I also don't really revisit my journals and my notebooks even though I have a number of those. I've read and skimmed the headlines and stuff out there about how revisiting those things is almost more important than keeping those things.

But that's one of my intentions for active learning is to revisit the thoughts that I have throughout time on a semi-regular basis, every 6 months, every year, whatever it is, go back and look at what I learned from that book, what I took away from that book. Also, the other thing about your question about learning is I just try to read things that I don't typically read. I'm drawn to the income inequality and technology systems and third industrial revolution and all of these things, but lately I've been reading a lot of black authors, a lot of women authors, and I've tried to move myself away from just the white dudes that have had successful careers that talk about the things that I'm genuinely interested in, but they don't have the— they see the world in a way that's so similar to mine that I would like to see the world from someone else's perspective.

Books are a really great way to do that and for better or for worse, so is Twitter.

[12:14] Paul: But that's me. Yeah. No, I agree. I think Twitter increasingly I'm finding also just dissenting voices through Twitter in a way that you're able to quickly share information and be like, "Actually, here's a more nuanced point of view." Of course, it takes a bit of curation and blocking some of the outrage.

[12:32] Mike Tannenbaum: Very much. But at the same time, it's— Yeah. It's a really great way to even just observe. Listening is more important anyway. So even just observing other conversations or other people sharing their thoughts, someone that is different from you, just watching them in the timeline and seeing what they're sharing and what they're talking about helps me. And then it becomes a click hole.

And then it's like, oh, this is— I hear what you're saying. I want to learn more. Click. Okay, oh my God, I read that. Where can I get another? Click, click, click, click, click.

Then next thing you know, 3 books from Amazon are ordered and then I have 3 months' worth of reading cut out for me. But that's— it's like information discovery is another— I think we all deal with that with the constant onslaught of information, but learning how to curate that information and be intentional. A lot of what I do is rooted in mindfulness and is focused on intention. Whether it's ways of working or ways of living, being intentional about the choices that we make. In this situation, the information that we consume to me is a very— that's how I want to live my life. I would like to be— it's the only thing that we can be in control of are the choices that we make.

That starts with the intentions that we set.

[13:51] Paul: That's awesome. Getting back to your career, you went to— I think— did you go to Temple for undergrad?

[14:01] Mike Tannenbaum: I split my time. I went to Temple my freshman year and I transferred up to Ithaca College in upstate New York for my degree and studied business and communications. The theme has been I never knew what I wanted to do. That's still the theme.

[14:17] Paul: It's a very common theme with self-employed people.

[14:19] Mike Tannenbaum: Yeah. So, I studied business. I love business. I loved finance. I hated the people in finance. So I quickly moved away from that and ended up in communications, uh, focused on audio production.

But that introduced me to the world of— I'm a movie buff and a movie nerd, so that introduced me to like the production of movies. Um, so I explored that for a while. I watched too much Entourage and moved to Los Angeles with a desire to become a talent agent. Um, one of the other themes that I'm embarrassed by, but I'll share it, is that for a long time, and even still probably, I've always just sought the money because it brings "security." The things that I did in my early career were I think I'm interested in this thing and I can probably make a good amount of money from it, so I'm going to go try that.

[15:10] Paul: So they were kind of high upside type?

[15:13] Mike Tannenbaum: Yeah. Finance and mutual funds and hedge funds and those things.

[15:19] Paul: Hollywood.

[15:19] Mike Tannenbaum: But the people were just terrible in my opinion. Hollywood. On the production side, it's a little different, but that led to my discovery of digital agencies because I was in Los Angeles and there's a ton of digital work and there was a growing tech scene back in the late 2000s. Is that what we call them? Like 2009, 2010?

[15:37] Paul: Yeah, I was trying to make sense of how these pieces fit together. It's kind of like a coding tech angle and then the Hollywood angle. What did you learn on the more— I mean, I'm sure we can understand some of the downsides of that, but on the positive side, in terms of thinking about talent and people, what are some of the positive lessons you took from your experience in the Hollywood space?

[16:05] Mike Tannenbaum: Sure. I'm going to actually credit my father with this, so shout out to you, Pops. But he always said to me— I mean, this is maybe like a prototypical, just straight white man thing to say, but it's not what you know, it's who you know. At the time, I was always like, "Stop, Dad. I'm supposed to get good grades." In hindsight, all of my opportunities to this day come from who I know. When I was in Hollywood, I was working for a guy, used to work at a big talent agency and now is on his own.

He produces Ringo Starr. He's got big names. He would just sit in his basement in Bel Air and roll phone calls all day long and be on the phone for 30 minutes with— who you thought was an old friend, and 20 minutes into it, he would make an ask, he would close a deal, another 10 minutes of like chit-chat conversation, and then he'd hang up the phone. And then he'd look at me and he'd smile and say something cocky to me, and then he'd pick up the phone and make another phone call. So studying the way that he did that kind of paved, combined with what my father had told me, kind of paved the way for my career, which kind of grew into like a business development path, and that wasn't by choice. That was— I needed a job, I found a place that was hiring, and I applied to one role and they thought I was better suited for a BD-type role.

But my time in Hollywood, it was so built on relationships. Yeah, all of my friends who were production assistants or producers or talent managers or whatever, they were— all of their work came through network and came through people. And that was a large value of of the Ithaca College network is that there's a ton of people making entertainment in Los Angeles. So people, I mean, that's my focus now. I didn't know it back then, but that was my focus back then. People are kind of the common thread through my career.

[17:53] Paul: Is it some of the frustrations you experience personally that you're trying to solve, at least for yourself, but also try to extrapolate to the system-wide and try to understand some of those things?

[18:04] Mike Tannenbaum: It's 100% the frustrations. I have had a bunch of jobs in my career. MikeTannenbaum.com, I guess, will lead you to my LinkedIn for those that are interested in exploring. But the thread has, for me, it's been focused on people, and I've only worked in what I would call toxic environments. So I'll just call it out right now. I've never worked for a per— I never felt like I had a mentor.

I never felt like I was coached and supported. Uh, I always work in roles where I had to figure it out on my own and build my own stuff and find my own way. And I was fine with that. Like, I like it. I'm an entrepreneur now. I, that's, that's what I do with my time based on the experiences, the most recent experience I had at a, uh, now bankrupt startup.

Um, but based on my most recent experience there, I set out to with this tagline of making business more human. I wanted to fix culture and fix leadership and help people build organizations. And I never thought about like org design and teaming and that those weren't words of mine, but based on the fact that I never had mentors and I always had to do my own, you know, carve my own path forward and create my own stuff. And, you know, people around me were complaining about work. People at different companies were complaining about work. The books I'm reading happened to be Onward by Howard Schultz about how he built Starbucks and Start Something That Matters by the guy that created TOMS Shoes.

I've always read books about how you build good business, but I had been in environments that were almost like the polar opposite of that. Those two threads converged and I was like, "All right, I'm going to do what I can to make this stuff better." That just opened up a world of— new opportunities.

[19:55] Paul: And when did you finally tell yourself, "Okay, now I am taking the leap," or was it just because of the circumstances of that startup that kind of made it happen for you?

[20:05] Mike Tannenbaum: So, that's been forever in the making. My dad was self-employed, so he kind of set a model for me. I unconsciously chose to see the good sides of it, like the freedom, the flexibility, the "my dad's always there for me" part of it. And not the like, holy crap, where's my money coming from part of it. But that was certainly there. But I've— my whole life I've always wanted to do my own thing and have my freedom.

Like, it's about freedom. And I had made attempts in the past to do my own thing, but like, I never knew what that thing was. So I went out to try it, but I didn't have an it, and then I had to get a job. So At this recent experience, I had been fed up. I had been frustrated. We had gone through management changes.

We had gone through a lot of shenanigans. I'll just summarize it as. And I hit my wit's end. And I talked with my now wife and some other advisors and friends. And I was like, "All right. I need a plan.

I need to get out of here." So I formulated a plan. I wrote my letter, and we had a vacation for, it was actually my wife's first retreat. She works for Buffer, so we were going to meet the Buffer team. So I was gonna take vacation. The company I was with was gonna launch a new product that I had worked on and rebrand while I was there. My goal was to come back from that trip, put in my letter, resign, you know, finish my 2 weeks, and then go on my own.

They let me go the day before I went on that trip. I said, "Thank you," and shook their hand and walked out the door. Because literally, the letter was written anyway, but I was just able to get a— They're like, "Here." They did it for me, which was even— It would have been nice to say the words on my own terms, but severance and unemployment gave a little bit of cushion after that. So it was kind of a push out the door, but it was a total plan before it. Yeah, I agree. Not bad.

[22:09] Paul: So what did you experience in those first 6 months of being self-employed and what's different more recently?

[22:18] Mike Tannenbaum: For me, the biggest challenge— and this is a very personal thing, but I'm a very open book— my biggest fear is not having money and not being able to pay my bills. And my therapist recently helped me realize there's probably no scenarios where, like, that actually happens. But nonetheless, it's a fear of mine. So when I set out, I was very like, I wanted to create all of these things and make all of this stuff. But it takes time to do that. And I was very much of the mindset I need to go figure out how I'm gonna make money.

Even though I had this whole plan that I had been working on for 6 months to leave the company and go on my own, and I got a tiny version of a golden parachute, let's say, but a very tiny version. But I was still driven by the fear of not having income. So I started scrambling for how can I, make some money. At the time, I thought I wanted to be a writer, and I am a writer, but I thought I wanted to like make most of my income as writing. So I found some freelance writing gigs for like $60 here and there, and I was able to write. And then I found a freelance writing gig for an agency, and that was $600, and I was like, okay, that's cool.

But I was very much like hustling for the money, and before I was doing the creative stuff that I had set the intention to do anyway. It was just like, it was that fight or flight, like, fear moment. And now, 3 years later, I still have that fear and that concern, but I've learned that if I need to go produce income, like, I can go do that. I can go find work and I can go do the, you know, I can go make that happen. My whole goal is to create things and to work with people and to bring joy into other people and lift up other people, and that's how I want to spend my time. So I do work for other companies sometimes that I don't really want to do, but it's still exciting work that pays well in order for me to have time to create something.

And that's how I created this book, Clear Path Forward. Um, my guess is that we'll talk about, but like I'm finally able to now, 3 years later, carve out the time that I wanted to carve out 3 years ago to create the things that I wanted to create. That is a huge difference for me.

[24:56] Paul: Yeah, that resonates so deeply with my journey and what I've heard from other people. I think when people take the leap to freelancing, they figure out a couple of things. Oh crap, I need to make money. And it's a necessary evil almost to figure out a few ways to try and make money just to prove to yourself, yes, I can keep doing this. And then two is to realize that you can't actually just keep showing up for stuff you're average level excited about, right? That actually works in a full-time context because you're going to keep going and you're just going to get some work done.

So you can do something you're like a 5 or 6 or even a 7 excited by. But to sustain it on your own, like you really need that stuff that lights you up. Otherwise, like it's just going to be such a pain or a slog just to like go to a desk and work on this stuff. I don't know if that's, uh, it sounds like it resonates with you, but, um, that's what I found, especially in the first couple of years. And then what's driving that, um, for a lot of people who are working on their own is this deeper drive underneath. To put something out there creatively, right?

And it sounds like you're finally doing that, which is awesome. So maybe we can dive into the book. When did that first come up for you and how did you think about publishing it?

[26:18] Mike Tannenbaum: Sure. So I agree with everything you said. Let the record show that that journey resonates entirely. So Clear Path Forward is a workbook and almost like a training program that is about 65 pages of written theory and exercises and then another 10 pages of 10 worksheets basically. So exercises that you can go through to, like I said about intention earlier, it's really helping you increase your awareness of the way that you work best. And the system within which you work, and then bring intention to all of that so that you can be more effective and have better interactions with your work, with your colleagues, with your technology, whatever it may be.

So increasing awareness, identifying behaviors, habits, and all that stuff, and then figuring out how to be intentional about communications and interactions. It came to be over, oh man, it morphed so many times. I had, I actually just took them down as the year kind of rolled over. But one day I thought I was gonna write, I was actually designing a workshop for myself that I was gonna work, you know, sell to clients. And I used the wall in my office and I had ended up with 5 columns which now became the 5 sections of this book, and under each of those columns, it was covered in Post-it notes and 3x5 cards, and tape and string between all of them, and it was, you know, A Beautiful Mind kind of thing.

And it was just me thinking about all the experiences I've had, the workshops I've facilitated, the coaching that I've done, the conversations I've explored, and all of that stuff, and the books that I've read, and thinking, okay, Where's their real, where's the need? The creative process for this started probably a year ago and never, you know, I just launched the book a month ago. So it took 11 months of mostly not working on it with a little bit of very, very, very focused time dedicated to working on it to bring this out. And it was, there's a whole world of, you know, quote-unquote like future of work and org design and better work and all of these things. I've been trying to find/create, I don't know which one it is yet, but I've been trying to find where I am most apt at fitting and what makes the most sense for me based on my experiences and my skills and my desires.

There's some companies that do work with large companies like GE and there's smaller companies that do work with little agencies around the globe. There's independents and all sorts of different varietals. It's the internet. You can find anybody that does anything really. For me, it was again with this rooting and grounding in mindfulness with an understanding of systems and almost like complex systems and increasingly within organizational systems. How can I help people enjoy work more?

Like that, it was a really kind of simple question. Um, and that led to the development of this thing. Um, there's obviously much more to it. It was really hard. Like I said, it sat there for a long time, but based on so many conversations about where the opportunity is and so many failed sales cycles, so many, a handful of successful sales cycles. Various projects that I had taken on and client work that I had done throughout the period, all of that obviously becomes fodder and input for something that you create.

And then I'm like, you know what, like, I just need to make something. I need to make something and I need to see if people are gonna buy it. So creating this for me, it was testing two things. It was one, can I create something, like truly make, like package it, label it, market it, sell it, like through and through. Can I make it start to finish? Then if I put it up for sale, will people buy it?

That's it. That's all I was testing. It's not my greatest achievement ever. I'm not even looking— obviously I want to put something good out there, but honestly that wasn't the goal. That was like a tertiary goal. In terms of can I create something, it's yes.

Just like if you focus on it, you can do whatever you focus on. Will people buy it? My answer for me was yes. So I'll pause there.

[30:59] Paul: That's awesome. And congrats on launching this. You launched it on a site I've played around with. It's called Gumroad. And basically you can go direct to people and just say, here's the price and offer them stuff. So I love to highlight stuff like that that just enables creators to go direct to people and say, here, look at what I created.

But yeah, I also just, I mean, going through your book, You can tell it's a platform for how you're thinking, and it was a way for you to kind of put down a paper and say, here's how I'm thinking about everything. And then that gives you also something to go to people to have a discussion with and have frame that discussion around that. And I think this is so important for people that are creative because you can't just put your ideas out there verbally. Those are a dime a dozen, right? You need to actually create something people can engage with you on, which is what you've done here. And it's, uh, it's pretty cool.

You can do it from a team perspective, individuals, but, um, I found a lot of useful exercises in there about how to think about time, the elements of work, enjoyable projects, dysfunctional projects, and all that. So maybe you want to talk about like one or two of the sections and maybe some of the specific actions, um, through the exercises that might be interesting for people.

[32:23] Mike Tannenbaum: Sure. So the book is, so basically there's a personal and a collaborative edition, and the collaborative is the all-inclusive. It's the personal plus another section which is focused on the interactions that you have with other people. So the theory behind the book is, part of me wants to take credit for it 'cause I created it, but part of me, you build on other people's ideas, so it's a lot of input from a lot of different places. The opening kind of theory is that there's 4 different types of work that we do. I don't mean industry, but like actual activity.

There's planning, coordinating, creating, and distracting. So technically there's 3, but like we all know what distractions are like, so you got to include that in a category. Correct. So ultimately, especially as like knowledge workers, as creative workers, in the majority of roles today, at least that I interact with, and maybe this will show you my bubble, but most people are creators. And I believe that project managers and team leaders are creators as well. If you're in that path, you are creating outcomes.

And like, when I say that, it kind of sounds cheesy, but like, I truly believe it. Like, if you're a project manager, your job is to be on budget, on scope, and on time, and you have to make that happen. If you don't create that outcome, you're not doing what you're supposed to be doing. So like, everyone has their version of creating. It's not just for photographers and designers and coders and all of those things. So the first section of the book, and this is a free worksheet that we can link in the notes, I guess, and I'm happy to offer a discount on the book for other people, but the first worksheet you can get for free without the theory, but nonetheless, it's an exercise to help you Just like sit back and be cool and reflect and get a little introspective, grab a pen and paper, make a cup of tea, and assess the work that you do and the way that you do that work.

And it's hard to be honest with yourself. It's hard for me to be honest with myself. Tools like RescueTime, I don't use them because I don't want to know how much time I'm spending on Twitter. Like I'll tell you right now, way too much time. But when you look at your work and you just remove judgment, again, that's a piece of mindfulness. Just like let go of the judgment.

Just let things be as they are. They are as they are. It's not worth judging them. Your work is broken down into planning, coordinating, creating, and distracting. So planning is the work before the work. It's setting everything up.

Coordinating is wrangling information, setting meetings, gathering people together. And creating is the actual work. And again, depending on your role, it may be different. It will be, you know, if you're a designer, obviously you're making mood boards and artboards and UIs and all of these things. If you're a team lead, your creation is a successful, cohesive, high-performing team. Like that's what you're creating.

That's your output. It's less tangible, but it's what you're responsible for. So, you know, the book starts with that theory of the 4 different types of work and helping you identify those things with a worksheet called "Where Does Your Time Go?" Then it moves into a little bit of the different functions that— not functions, but the different areas that contribute to your work. So things like space, like where do you do your best work? Time, are you an early bird or a night owl? Do you work best with people?

Do you work best alone? Do you like asynchronous communication or do you like instant, like real-time threads back and forth? And is your information readily available? Do you have to spend hours chasing information, hunting for information, finding it, and so on and so forth? So it's looking at these components of work that most people, if not all people, myself included, don't make time for. And it's actually carving out the time so that we can look at what do we need, what do I need, you as a reader, what do you need to do your best work?

What are you getting and what are you not getting? And why are you not getting what you're not getting and how can you get it? So it's very much empowering you to understand the way that you perform at a high level. Then the team edition just extends it out to— so instead of just looking at interactions for you as an individual with your work, it looks at the interactions that you have with the system within which you work. When I say that, I mean it's easy. My wife works for Buffer, and she talks a lot about her team.

She's one of the only people I know that refers to a team. Other people call them colleagues, and she calls them teammates, which I think is a beautiful thing. But a lot of times, you, within an organization, within a company, you have interactions with people that aren't necessarily on your team, but they're still interactions, they're still equally as worthy, whether it's a client, a customer, someone in engineering when you're on the marketing team, or maybe it's your advisor who was like a boss from a former job. All of these people make up the network that surrounds you and the system that surrounds you, and they help you in some way, shape, or form. You need things from these people and these people need things from you.

So if we take time to identify those various components of the interactions and the needs that different people have, it's— you set yourself up for— you set everyone up for more success because you have an understanding of the interactions within that system and the way that all of the different components are playing together to create harmony.

[38:12] Paul: So maybe we can bring this alive for people. Was there anything you did as you were writing it to rearrange your day or your time to question some of these things? I mean, you're writing it and you probably had to come face to face with, "Oh crap, I should probably do this myself." Yeah, I've hit that moment a few times.

[38:32] Mike Tannenbaum: So I've gone through the exercises in depth very thoroughly. But for me, it's creating it was actually less about putting myself through it and more just about what is it that, what are the questions that I want answered. I mean, it's selfish, I guess, if I can be perfectly honest. It's exactly like, what do I think I need in order to do better work? And what do the other people that I work with need so that I can help them do their best work? So for me, it was very much sitting down and looking at What kind of— when do I want to send emails?

When am I most creative? When do I want to write? Even last night, I've been trying to build up—

[39:14] Paul: Yeah, give us some answers to those questions.

[39:18] Mike Tannenbaum: So, I'm a night owl and an early bird, which is like a terrible combination. I like to get up early and exercise and enjoy my intake of news and reading, but I really get creative from like 6:00 PM to 9:00 PM to midnight and beyond. Balancing that is something that I'm working on right now. I'm trying to build a new writing habit on a daily basis just so that I write every day. I put that in the morning because for me, if I don't do it in the morning and it's a habit, then I'm probably not gonna do it later in the day. After 2.5 weeks of doing that, I just hate it.

I hate waking up and writing first thing. I just don't enjoy it. Now I'm shifting that to at night where it's more reflective writing, and the pressure's off. There's no emails, there's no meetings, there's nothing. The world is silent. Even if it's like 11 PM, like for me, you know, it's a little bit of a later night, but I can just like let go and not have to worry about the expectations that I put on myself that I think other people have for me, and I can write what I feel like writing.

And ultimately, that's going to lead to me coming up with new stuff. So, kind of rearranging the way that I have my day and learning that I need to give myself permission to not work and I need to give myself permission to do something that isn't typical of a workday. I still hold myself to that 9 to 5 even though I'm 3 years into working for myself. I don't mean that I work 9 to 5 hours, like my hours change all the time, but I still have this mental model. Like I haven't been able to break this mental model of like my work needs to happen between 9 and 5. And that for me is very, very restrictive.

Like I can't imagine what happens on the other side of it when I smash that model and I realize that I can do work at all hours of the day and I can enjoy myself at all hours of the day too. Work doesn't have to happen between, you know, my 9 and 5 is different than your 9 and 5 when you're over in Asia. Like they're different hours.

[41:21] Paul: Yeah. Are you experimenting with that at all this year?

[41:25] Mike Tannenbaum: With time shifting, kind of?

[41:27] Paul: Or maybe even just working less?

[41:32] Mike Tannenbaum: I sent a tweet that was kind of sarcastic and probably privileged, but I think it's totally true. I want to work as— and I have a hard work ethic. I've been working forever. But I want to work as little as I possibly can. But create as much as I possibly can. And even though I write about this stuff, about, you know, I used to write about distraction and about boredom and creativity and all the things that you see people writing about now.

And it's hard to live that. Like, it's hard to let go and trust the process. I'm a Phillies fan, we got the Sixers, like trust the process. And it's hard to be like, okay, I'm gonna go take a hike with my dog in the middle of the day, and I'm not gonna think about work, even though it's like 2 o'clock on a Tuesday, everyone else is working, but I'm gonna go hiking because you know what, I can. And I learned that by letting myself do that, you know, I'll go to fall asleep that night, and I'll have an idea hit me, and then I'll get up and I'll write for an hour and a half, and then wake up the next morning and pump out a blog post or a newsletter or, you know, a part of a book. I'm constantly iterating with the way that I do work and the way that I communicate and the expectations I set and how I tell other people about that.

[42:54] Paul: You're a big reader as well. What are maybe 1 or 2 big influences on you or you just wish more people would read either in the corporate world or just generally when thinking about their careers?

[43:09] Mike Tannenbaum: I think that's a great question. Read something that's not a business book.

[43:14] Paul: Give us a couple.

[43:15] Mike Tannenbaum: Oh man, The Alchemist is my favorite book ever. I don't know if you're familiar with that, but it's a beautiful story of a boy wandering through the world. It's one of those books that I have by the side of my bed permanently just because sometimes you want to open it and pick it up and just feel good. So, The Alchemist is great. Living with Uncertainty is another one. Both of them are books that are kind of about the journey and just learning to embrace things as they come to you and being comfortable with the uncertainty and with the fear and with something unexpected coming up.

So, for me, I love— I love reading that. Philosophy, I think, is hugely important to read for whether you're in business or whatever work that you do. Read things about the world. I'm trying to come up with— I mean, those were two specific examples. Right now I'm reading a book, Winners Take All, which is basically economic inequality. The Third Industrial Revolution was a great book.

Reinventing Organizations, if you're interested in work, is kind of the first— like a lot of people's first entry point into exploring what it takes to create a more effective organization. I can share a few more in some show notes and put on Goodreads, but I think diversity is important. I enjoy Seth Godin's writing and I enjoy Simon Sinek's writing, but like for every Seth Godin book that you read, read like 3 books written by black women, or read 3 books written by someone from a different part of the world than you. Read Ta-Nehisi Coates' Between the World and Me. Like that book just, it just changed my worldview entirely. And I grew up in a super diverse high school with a lot of friends from all different races.

But that stuff informs my work. Like, that is the future. The future is global. We are fully connected.

[45:24] Paul: Yeah. And I think the lens I've actually been trying to use is less about people's identity or anything, but just different languages. And that obviously has a lot of overlap with people's identities. But languages like just poetry, fiction, nonfiction. I think a big problem with business writing is not as much one type of person, but it's one type of language and one type of way of seeing the world. I mean, there's not much difference between business leaders writing about business these days, no matter where they come from.

It's all based on a similar foundation. Then you discover something like poetry or literature, and it's like, holy crap, this is a new language, and the corporate world doesn't have this.

[46:13] Mike Tannenbaum: I completely agree with you, and For a long time, I wasn't reading fiction. I realized that I was just reading the business books and the nonfiction books. I love them, but I'm a writer, first of all. I feel like I should be reading everything. I wasn't reading any fiction. I wasn't exercising the creative— I wasn't writing any fiction either.

I was just journaling all the time. By doing the things that are different from what we typically do, we create new opportunities for ourselves. We see new things. We learn new things and we grow whether we know it or not. All the things that we take in ultimately become a little part of us. I love it.

Poetry is something that I have a couple books. I'm not really big into poetry, but I keep trying to get myself into it because I'm an artist. I'm a musician mostly. I'm not really an artist, but I believe that exploring all sorts of creative outlets and listening to things that other people create and not just the top movies on Netflix and the top books on Amazon and the top books or blogs on Medium, but finding the lesser-known things. If you want a place to start, go look at Austin Kleon's website. He'll send you 10 things, 15 things a week that you never knew existed that will broaden your horizons creatively 100-fold.