- All right, Jesse, well, I'm liking the live interaction we've put into the show. Last week, we had our friend David Sachs in the studio helping us answer some questions. Today, let's take a live call from one of our listeners. - Yep, we got Phillip here, so let's take a listen.

- All right, Phillip, thanks for calling into the podcast. What is on your mind today? - Hey, Cal. So I've been recently going through a bit of a life shift. I spent a few years as an entrepreneur running two venture capital-backed startups. Then after selling my last company, I worked in product management roles at a couple of later stage technology startups for a few years.

And that was a lot of hyperactive hive mind, you know, over 100 Slack channels or 30 meetings per week. A lot of structured what I was working on also, though. And so now I've split out to start a new company. And my goal is to build it solo without external funding, kind of Basecamp style.

And I'm spending about half of my time doing consulting work to cover costs. And I'm spending the other half of my time developing my own in-house products. The goal is to grow these in-house products and revenue so I can eventually focus on them more full-time. And I split out solo because I did some value-based, lifestyle-centric career planning and decided that starting a solo product development studio aligns more with the values and lifestyle that I wanted to pursue.

So my high-level question is, how do I apply the principles of slow productivity and deep life to set myself up for success? I've gone from a lot of structure to no structure, and I could use some help making sure that my habits are sustainable. - Well, I mean, first of all, I'm upset that you're not using our acronym for that.

- VBLCCP. - VBLCCP, yeah. I mean, this is, we gotta be pithy. I think we all agree that that rolls off the tongue. Okay, this is a great question. Tell me a little bit more, though, about this studio situation you have set up. What's that like? So what's the work gonna be like?

- Yeah, so I'm doing some product development. So I'm working with a client, kind of building an entire application, end to end, including definition and design and things like that. And I'm working on a couple of personal projects, like one of which is the main focus, already has revenue, already has some customers.

It's not quite revenue to live off of. This is a path I used to start my previous company, Moonlight. So we did some freelancing as we grew the company, and eventually it grew in size and raised venture capital and kind of took a traditional kind of path. And I think a lot of what I'm trying to do with this product studio is also not necessarily trying to pursue that traditional path.

There's a lot of kind of extrinsic markers of success. Like you could go raise money and hire employees and things like that. I'm trying to be a little bit more controlled about that. So my day-to-day is really unstructured. I have full control of my time now. I have one client meeting per week, which is a lot less than what I had at later stage startups.

So I'm tending to break my day into three, two-hour deep work blocks with kind of two hours in between each for a mix of admin work and breaks. So I guess kind of like a general high-level question I have is, is this too much or too little deep work in a given day?

And with more control of my time, is it better to break up my day more or to try to keep deep work and more work, admin work, focused on more of a traditional kind of nine-to-five slot? - Yep. All right. That's a good question. And we'll get in this nitty gritty.

I wanna underscore first, I like your decision you made of, well, let's keep this small. Have you read Paul Jarvis, "The Company of One"? - Yeah, I've read part of it. I don't think I finished it, but it's a good book. - I mean, you're right in line, I think, with Paul's thinking here.

If people haven't read that, they should. It has a blurb for me, so you know that it's quality. Paul also, he was a designer, I guess. He was in web design. And the whole book is about, instead of expanding your company, so companies that begin with you and your skill, instead of expanding it to hit those intrinsic markers of success, so size, revenue, then funding, his whole point is keep it small.

If you get more in demand, you can just charge more and therefore even work less. Like actually, it can be a great engine for a lifestyle that you have a huge amount of autonomy over. And I think it's a great model. So in terms of your specific day, there's no right answer to the exact right way to move deep work around how many blocks to have.

I have a couple of things I'm gonna throw out there, a couple of heuristics, and you can see which of these might stick. I'm a big believer in these situations of doing meeting-free Monday and Friday, if you can. So you just have the scheduling heuristic that client calls, client meetings, you know, whatever, I gotta call my accountant, we gotta, the IT person's upgrading some sort of software, whatever it is, nothing gets scheduled for Monday and Fridays.

That alone just changes the character of the week because it's like you have a four-day weekend, you're just deep working on Friday, you're deep working on Monday, you can really get lost in things. So I think that can make a big difference. And then the other thing I might suggest would be consolidating the deep work.

All right, deep work to lunch, meetings, clients, administrative stuff in the afternoon. Trying to keep that together, keep that mindset going, and not have anything interspersed into that that's unrelated. So those are two heuristics I've seen. Would that graft well onto your current setup? - Some, yeah. I really wanted to live more asynchronously when I started this company, so I only have one meeting per week normally.

- All right, that's easy. - Yeah, so that makes it easier, but that also is a lot more uncertainty in terms of should every day kind of be the same or kind of create more texture throughout the week. But yeah, so you think that kind of training to do longer periods of deep work is better?

- Yeah, I would do it first thing in the day, until lunch, maybe just make that be a standard. And then the other thing I would do, I mean, you have a very enviable situation here. You have a huge amount of autonomy in terms of demands on your time because of the way you set this up, so congratulations.

This is something I do during the summer. Like when I'm a professor in the summer, I'm like you all the time. So I have many fewer obligations. My time is very, very open. And so I have the same concern about how to structure it. It's deep work in the morning and then variable but clearly defined shutdowns.

That's another thing I lean into is I'm gonna time block out my afternoon. I'll be clear about when my shutdown's gonna happen this afternoon. And when I'm shutdown complete, I'm not working on work anymore. That can be really early some days, right? So what this allows you to do is it's Tuesday.

I deep work till lunch and that went really well. I don't have any particularly pressing administrative thing. I'm gonna do a formal schedule shutdown ritual at one o'clock and because I recognize, hey, this day is done and I feel good about it, I can really lean into those other hours to do other things, completely unrelated to work or whatever.

And then on another day, you said, look, I got my call with my client and now I really gotta figure out whatever, this new software package. And so this is gonna take me till five and I'll do the clear shutdown then. But having the clearly defined shutdown each day, I mean, allows you to really work with this variable workflow and take a lot more advantage of what it gives you.

I mean, maybe you wanna become a cinephile. It's like, great, two days a week, I'm going to the movies, the two o'clock show or whatever. That's the type of thing you can do when you feel like I shut down, I feel comfortable shutting down, I'm looking at my schedule, this is good, I'm on track for things.

And so now I really have to figure out what to do with my time. That's what I might also be concerned about if I was you, is making sure it's not this hazy mix of work and non-work guilt in the afternoon. Like, I don't know, maybe I should go back on email, what's going on.

Be clear about it, but then be very comfortable taking advantage of all the advantages you have. - Okay, great. Another kind of question along the lines of slow productivity is, should I work on weekends? So I'm trying to do some client work and some personal work. So I am not sure if I should continue working on weekends.

Right now I'm taking one day off per week, but I think there could be value in getting more done. So how do you think about working on weekends? - Would it be the personal project that you're mainly doing on the weekends? - Yeah. - I think it's fine. I mean, if you have the time and you find it interesting, I think you're smart to take, whether it be Saturday or Sunday, a full day completely off is fine.

But if you're working on a personal project, I think that's fine. I typically will write on Sundays, for example. I don't do any other work on the weekend. So I'm not gonna do, I'm not gonna do CS work. Producer Jesse knows I'm probably not gonna answer emails about issues with the podcast, whatever, but I do write.

Because it's a very personal activity for me. It's meaningful to me. It doesn't change me into a mindset of hyperactive hive mind. So I think if your personal project is not throwing you back into a world of scheduling meetings and sending emails, but it's coding or is trying to master a new system, I think that's completely fine.

I mean, if you enjoy it, go for it. Keep you one day off. I mean, I think you got this pretty well dialed in here, Philip, from what I'm hearing. - So one of the life buckets is community. I've moved around a lot. I was a nomad for two years and I'm temporarily in a new city with my significant others in grad school.

How do you think community should factor in for somebody in my situation? I think there's not a lot of local people that are in the same situation as me, but a lot of online communities tend to be more real time, like Discord or Telegram. And I don't wanna have those kind of synchronous demands on my attention.

What do you think is a good way to kind of continue to have some community? 'Cause I don't really have that from coworkers or from kind of other companies in the same situation through an investor or something like that. - What city are you in? - I'm in Chicago.

- Oh, okay. I mean, I think you should have community involvements. I think they should have scheduled synchronous demands on your time, and I think they should be in person. I think that's an important part of the human condition. And as I talk about in digital minimalism, it's actually the non-trivial sacrifice of time and attention on behalf of other people that makes that connection something that's valued by your brain.

And so I would put in that work now. Now, are you saying your significant other is in grad school somewhere else, or you came to Chicago because- - I'm here. - Okay, that's good. - Yeah, we're here in Chicago, she's in school. I think I agree with what you're saying.

I think what I'm having trouble with is finding peers. - Oh, that's hard. - There's a lot of people that are more advanced or learning from me. But I think where I find I have issues is a lot of my kind of peers that I know are in other cities, not necessarily locally.

- Yeah, well, I mean, I'm saying get entangled in some community involvement here unrelated to your work. - Okay, that makes sense. - Yeah, I mean, it could be through fitness, it could be through faith, it could be through activity, whatever, trail running or whatever. I mean, there's such a wide variety, but I would anchor myself right away with, or if you're into, I mentioned movie, you're into movies, like let me find a club that meets and does these things.

And that becomes the offshoot of making friends and people you end up spending time with one-on-one. I think that's really critical. I would recognize it's hard, right? Because we don't have like an app solution for that. We can't just like swipe a thing and then like a friend comes over.

But I would put a lot of effort into that, especially if I'm new to a city. And you have the time and flexibility to do this. And I think that's a great investment of the time you have. - Yeah, I've done a good job of meeting friends and communities locally, but I think the thing that I'm finding hardest kind of being solo is like professional peers and people that are working on similar problems and things like that.

So I've considered kind of like setting up like a mastermind call or something weekly with some people that are working on similar things here. I think that's really kind of the main thing that I'm concerned about is meeting other people that also think this isn't as crazy and that are going through kind of similar professional challenges or things like that.

Yeah. - Yeah, I see what you're saying. I mean, I think that could be helpful. Writers have the same issue. It's a very lonely job. You don't go to an office and it's weird. Like most people aren't writers, so it's hard to find. And I've done something similar. I've been involved in various writers groups.

I mean, in my sense, the value falls out of those is not the fact that we're getting together on Zoom every other week, it's the six months in, this particular member of the group you kind of connect with and now there's someone you text with. Now there's someone that like you see when they're in town.

So I see your question better now. I would say it's worth it having the, you talked about the synchronous commitment, make the commitment. I think that's fine. - Yeah. - Get together some groups. Yeah, they're usually mixed. These groups are okay, but it's like who you meet in the group could be pretty valuable.

So I see what you're saying there. But on the other hand, hey, as a writer, I can say it is pretty lonely. I mean, I know other writers, but it's a pretty, it could be a pretty lonely job and that's just part of it. So you find connection outside.

I mean, look, I built this studio so I can come hang out with people because otherwise I'm just writing by myself, but also having my Georgetown position. I noticed a really big difference when the campus opened again, for example, post COVID. Like, oh, just being able to come here, be around people.

So I think that is really valuable. It's also just really hard. I just know a lot of writers who, some of them meet other writer friends, but it's a weird job. Your situation might be similar. So I think it's worth it to try those groups. It might help. You might meet some people, but I think you need to be okay with the fact that you may not ever have the same experience as the other person you know, who's in the 30 person venture-backed startup and they're in the office 12 hours a day.

And it's, you know, here's the ping pong table and we're just getting after it. You know, it is a little bit more lonely. I think Paul Jarvis is great about that in that book because he moved to the middle of nowhere. I mean, he lives, I don't know, in the woods.

He lives in the woods in British Columbia somewhere, but they love it, but it's like completely different. I mean, they're on their own if they're doing their own thing. And so you can be happy with that too. So I basically am validating your pain here, Philip. It is hard and you can probably, you might be able to do better, but I don't want to sugar coat it.

Like when you do a solo-preneur type situation like this, I think a lot of your community connection comes outside of work. - Yeah. How do you think about coaches? I think coaching is kind of having a moment right now and I've had some friends recommend hiring like a professional coach.

I think that also kind of factors into accountability that on some of the client projects, I feel like I can be working harder for someone else than I work for myself. Do you think, like, how do you think about coaching? - I think you should try it. Yeah, do a six month engagement that like, this is what we're trying.

So it's more like you re-up, not that you would have to actually cancel it yourself to see if it's a good fit or not. I have a coach. It is someone, she specializes in dealing with creatives who also are struggling with the issues of the business side of being a creative.

So, I mean, it is a very narrow expertise that I need a lot of help on. So she works with writers and filmmakers and screenwriters and directors and where businesses build up around their creative endeavors. And I found that to be really useful. So I would say I'm on board with coaching.

Not every coach is gonna be a fit. So try it out, but absolutely invest in that because you can get a huge return on that investment if it really changes the way you think about your business, the way you think about your life. So yeah, you got my stamp of approval on that.

I think there should be more coaching in general. And I think you're right, it's having a moment where people are realizing I do a high-end job. There's a lot at stake. It's complicated. There's huge dividends to get in my life if I could make big changes. I don't quite know how to do that.

If there's someone who can help me through that, it could massively change the trajectory of my life. I'll hire a trainer, I'll hire a doctor, I'll hire all these other things. Why am I not hiring someone that's gonna work on probably the most important thing I do, which is sort of figuring out exactly how my career unfolds.

So yeah, you got my approval on that one too. - Awesome, thanks a lot. - Great, well, Philip, thanks for calling in. I think it was a good case study and a good constellation of related questions. So definitely keep us posted on how things are going for you there in Chicago.

- Will do, thanks, Kyle. - All right, thanks. (upbeat music) (upbeat music)