Focused - 54: I Have to Try It, with Casey Liss

Episode Date: August 21, 2018

Podcaster and programmer Casey Liss joins David and Mike to talk about his Free Agent journey, what caused him to take the leap, the tendency to do too much, and his desire to pull the thread which has led to him becoming an Accidental YouTuber.

Welcome back to Free Agents, a podcast about being an independent worker in a digital age. I'm Mike Schmitz, and I'm joined by my fellow co-host, Mr. David Sparks. How's it going, David? Great. How are you doing today, Mike? Doing good. Not having to battle the fires that you've had out there in California, which makes me a little happy to be in the Midwest. We've got to put up with some cold in the winter, but some of the pictures that you sent over, man, I'll gladly take that trade.

Yeah, it was a little scary, but it was about a mile away. And in the past, it's got a lot closer. The good news is I live in attractive homes. I don't live out in the boonies, so it's pretty easily defensible. So I just have this kind of faith in the system. I'll be okay every time this starts up. But yeah, it is scary when you see it kind of creeping over the mountains heading towards your house. Yeah, that picture looks like it's on a fire watch or some apocalypse movie. Yeah, yeah. A friend of mine was flying

over California at the time and said that it was crazy because the clouds are all orange, you know, looking down. But anyway, that's not why we're here. We're here because a good friend of ours and a newly minted free agent is with us. Welcome, Casey Liss. Hello, gentlemen. How are you? I should have held back my laugh earlier to keep the suspense alive. My mistake. That's in the title. That's true. That's true. There we go. Well, hello. It is a pleasure to be here. I've been listening since episode one, if I'm not mistaken. And it is one of those things where I was like, do I even really need to listen to the show? I'm never going to be a free agent. That's just not my path. And then fast forward, you know, a year or two, however long it's been. And hey, guess what? I'm on the show. I'm never going to go out on my own, but I am a free agent in my little department, or I have established my own little domain, and they find some of the stuff we talk about on the show useful, and I think that's great. So, yeah, I get it.

For those who don't know Casey, he is a programmer, lately focusing on Swift, and he is also a podcaster. He does the ATP podcast, the Analog Podcast. Is that it, Casey? Did I miss any? No, that's basically it. I mean, I occasionally write for my blog. And I've been dabbling, as I'm sure we'll talk about, with some YouTube stuff. Yeah, well, that's next on my list.

You're a YouTuber, too. And Casey is making an attempt at being a serious YouTuber. And we're going to talk about that. Because, you know, it's like that is a very aspirational goal there pal yeah um tell me about it but but casey also um is like i said earlier he has recently quit his job and in fact casey had left his job he announced it right after jason had left the show and Mike had already, you know, signed on and, you know, I was really happy with Mike on, but everybody was thinking, Oh, it's gotta be Casey. Well, he's not the co-host, but we are getting them on the show.

So hopefully that makes everybody happy. And, and I want to talk about you Casey and we specifically picked this time because it's now been a few months since you've gone out on your own. And I felt like, you know, I didn't want to get you immediately. I wanted to get you after you had, you know, let it sink in a little bit, what you, what you had done, the reality of it all. And just, uh, talk to you about your journey. Yeah. So I, uh, quit my job. My last day was, uh, July 2nd of, of this year. So this was just a little over a month and a half ago. And I did that because healthcare,

because United States, yay. But anyway, I announced I was leaving about a month beforehand, right before WWDC. And I spent June trying to get my team to get all the information that I might've had in my head. July 2nd, I stopped working. So I would have healthcare for the remainder of the month. Then July 4th, we flew to England and met you there, David, as it turns out. And so since then, I've had probably a little over a month of just

adjusting to my new normal. And so the primary source of my income and my family's income is through sponsorships for the Accidental Tech podcast, for Analog on this very RelayFM network, and some of the other extracurriculars I do from time to time. independent. And the primary one was we have a three and a half year old son and a seven month old daughter. And it occurred to me, I think my wife was way ahead of me on this as with all things, but it occurred to me, you know, it's not that far from now that he's going to be going to kindergarten. And once he does that, he's kind of gone all day, every day. And if I wanted to be around for any part of his childhood, sitting here now, not having like a 15 year old or anything, it seems logical that I would want to be around when he and she, of course, are here all the time. And, you know, once Declan, my son, goes to kindergarten, it's going to be less of a big deal that I don't have a nine to five. And so, you know,

my wife and I started talking probably six months, maybe have a nine to five. And so, you know, my wife and I started talking probably six months, maybe even a year ago now about, Hey, could we make this work? And, and is this the right time, et cetera. And the reality of the situation is with so many things, especially like parenting, it's never really the right time. It's just maybe the least wrong time. So, so, you know, we went out on a wing and a prayer and we crunched a lot of numbers and figured out, you know, if we make smart financial decisions and perhaps don't live like we used to exactly. But, you know, we don't necessarily have to have to eat nothing but matzah every day. You know, if we just make smart financial decisions, then then we should be able to make this work. And and so far it seemed so good And it's been working out real well. The only

problem I have with it is that I have been far busier than I ever expected. And as Jason had warned me, and David had warned me, and I'm sure Mike, you've said the same thing. I have not been saying no as much as I probably should have. And so that's totally exacerbating the problem. But it's all good problems to have. And I am very pleased that I am as busy as I am because the alternative is obviously very, very, very uncomfortable. Yes. I met up with Casey in San Jose at WWDC right after he announced it. And I remember a conversation with you, me, and CGP Gray. And I said to you, Casey, the biggest risk you have is you're going to take

on way more than you can handle, right? And you and Gray both said, oh, you said, no, that's not going to be a problem. That's not going to be a problem. I'm doing this to spend time with my kids. I'm just not going to do that. But it happens. You just can't help yourself, right? I know for me, the big fear was if I don't do this, we're going to lose our house. You know, if I don't say yes to everything. Exactly. Because it's like, it's all on me, you know. And in your case, your wife has a good job.

And you thought, well, hey, I don't have to take on a bunch of work. But there's something inside you that just drives you to say yes. I get it. And I know the reason I can talk about that mistake is because I still make it every day. I think part of that maybe has to do with the parenting aspect. It's kind of funny. I mean, I work with a company called Asian Efficiency in the productivity space. And my gateway into productivity and free agency is the same as a lot of other people's exact same thing you described, Casey, it's like, I want to

be home with my family. It's one of those things where if you don't have kids, you can always put it off. You can, oh, I'll get to that tomorrow. I'll get to that next week, next year, whatever. But when your kids are growing up in front of your face, you realize that your time is limited and you have to make this decision now. And then when you do make that leap, then you are battling the noble intention of wanting to spend time with the family with, oh my gosh, I still need to provide for my family, which makes you try to jump at every opportunity that presents itself because it's like, oh, this is my responsibility. That's a very hard balancing act. Yeah. And it's also, you know, I am extraordinarily, extraordinarily lucky. And for whatever I say for the remainder of this episode, I hope that it is clear that I, as best I can, recognize how lucky I am.

And we knew, based on the income that podcasting had brought us, that, again, if we made smart decisions, it would be enough. So it's not – if you look at the numbers, we're not going to lose the roof over our heads. But then I created a new problem in myself in myself, which was less. Oh, my God, how will I be able to pay for the mortgage next month? And instead of that, it's oh, my God, if podcasting goes away, then what will we do? You know what I mean? So like even though the near term is actually pretty solid, knock on wood, it's the long term that I'm now worried about. And so now I'm trying to diversify as best I can. Hence the YouTube stuff, which surely will never make money, but it's at least fun. And again, we'll talk about that in a minute. But the YouTube stuff, it's I've taken on just a tiny bit of 1099 of contracting work, which really of that administrivia taken care of and preparing myself so that if something drastically changes with the podcasting world, then at least I'll be ready to rock in the consulting world if I choose to, I want to try to work less than 40 hours a week if I can get away with it. And I've done an okay job of that, but I envisioned like, oh, I will work exactly, you know, half time.

And that will be enough to do the stuff in addition to podcasting. And in reality, I can't help but say yes to things and bleed into the time that I was hoping to leave for the family, which, you know, it's, it's, again, I'm extremely lucky. I'm extremely, extremely lucky. And it is a good problem to have, but it is, it is a bit of a problem nonetheless. I think one of the things that I did not expect was cause you know, the idea of leaving and working yourself up to do that, to take that leap, um, is a stressor. And it is a thing where in the back of your mind, you're like, can I do this? Can I make it work? Can I get work can i get you know you've got this thing going on and you think that once you make the leap then you're going to remove at least that element of the stress from your life because okay i did it so now i don't have to sit around and panic and worry about whether i should do it or not because i did

it but what you don't realize as soon as you make the leap, a new panic arises. And it's like, especially if you like it, and that was my case, okay, I really like this. How do I keep it? How do I keep it? What do I do to keep it? Don't screw this up. Exactly. And so the long-term goals and the diversification of work and multiple income streams and a lot of the themes we've talked about on the show immediately rise to the top. Yep. Yep. It's very, very true. Another thing you talked about, you know, just kind of unpacking that a little bit is the importance of health insurance and the decision. And that's

something I don't know that we've ever really talked about on the show, but I know that that is something that affects a lot of people in making their decision. Could you talk a little bit about that? Yeah. Yeah. So, you know, back, what is it? Five, six years ago, um, you know, I was working as a professional developer and, and my wife was a high school biology teacher. And then when we had Declan, um, in October of 2014, you know, she, for that school year, she, she did not go back to teaching and our hope and our continued hope is that she won't ever have to go back to, you know, traditional work unless, you know, for some reason she chooses to. And so that means I was the only one who could provide health care. And since I had a regular, as I would call it, jobby job, then that's not a problem because, you know, health care comes with your job. At least that's the way it works in the United States. Then fast forward to, you know, six months to a year ago, and I'm starting to really consider being a free agent. And I actually, when my

daughter was born in January of 2018, in January of this year, I took an extended paternity leave. I got three weeks from my employer, which was tremendous. And then I took another, I don't know, like six or eight weeks as well. So I basically took off the first two or three months of the year. And that was unpaid for the most part, you know, after those three weeks. And in fact, I had to fund my own insurance to some degree, like it was still through my work, but I had to give them money, which was a little bit different. But I bring all that up to say, I was weighing, well, should I even go back to work? And the conclusion I came to was, I need insurance. There's no two ways around it. And so I believe it was March or April,

I went back to work and I thought this is the way it's going to have to be. And I didn't dislike my job. I mean, it was a job. It was frustrating, but I liked it by and large. And then what happened was we ended up having to fight with our insurance company a lot with regard to various and sundry bills for my daughter's birth. And I started really digging into what is this insurance cost us? Like, what is our portion of the insurance? And I knew that our insurance policy with my work was not great. And I knew it was not cheap. And I should have done this a long time before.

I should have done this in the beginning of the year when I was at home. But you guys both know that newborns make everything stop. So I didn't exactly have an overabundance of time to figure this stuff out. But I started crunching the numbers and realizing that, and I'm making up the numbers. I honestly don't remember what it was offhand, but it was something like our take home bill for my works insurance was something to the order of between $500 and $1,000 a month or something like that. I forget what it was. And I started looking on healthcare.gov, which is colloquially known as the Obamacare website, and it's basically where you can find self-provided insurance. And if work was like $500 or $1,000 of my contribution each month, Obamacare was like 1500 or 2000 or something like that so yes it was considerably more without doubt but it wasn't like it was 3x or 4x or 5x it was i think less than 2x whatever the cost whatever the actual numbers may be and suddenly when health care it's still an issue but it's not an issue, if that makes sense. Like suddenly when I can say to Aaron, you know, look, if we're willing to dump a few extra hundred dollars into this every month, if we're willing to pay a little bit more

for healthcare or kind of a lot more for healthcare each month, suddenly the one major thing that was keeping me at my job goes away. And then that changes the math pretty dramatically. And that's basically what ended up happening. I think if I had a better and or cheaper health care plan at work, I may not have gone independent. But because of the bananas way that America works with regard to health care, it ended up that I am certainly losing money on this deal in that I am paying more for health care than I was before. But the health healthcare doesn't seem to be particularly worse through Obamacare. And it's not heinously more expensive. I mean, it is hilariously expensive to go. I mean,

don't get me wrong. I believe it is a little bit more than our mortgage every month, but, but nevertheless, it is not astronomically more expensive. And so that was really the thing that pushed me over the edge and made me say, you know what? We probably can do this. And whether or not we can, it certainly seems like now's the time to try. And it took me a long time to realize this. Now I'm diverging away from healthcare a little bit and I apologize. But everyone around me knew that, you know what? If this doesn't work, you can just get a job.

Like that's how this works. you can just get a job. Like that's how this works. Like, and, and, and I knew that in my brain, but it took months, literally months for my heart to believe that, if that makes any sense, like it took a lot of convincing from Aaron, from you, David, from, from Mike Hurley, from Marco Armand, from all of these people to really believe, you know, if this doesn't work, it's not like you're not employable. Maybe I won't be in a few years, but right now, at least, you know, I'm still, I still know how to write code. I haven't completely fallen into the trap of being an unemployable independent worker. Like I could always go back. And once I really believed that and looked at the healthcare numbers, it occurred to me, I've got to try it. I have no, I have no choice. I have to try it. Yeah, that is that feeling of if you don't try it now, you'll never forgive yourself. I think

that is something that really plays an element for a lot of people. Yeah. And I wanted to be able to look back at Declan at 20 or 30 years old, and Michaela as well, but she's so young. she's barely a person at this point. Uh, but, uh, I wanted to look back at the two of them and be able to say, you know what? I did my best to be there for you guys when you were super little. And when we could spend a ton of time together and it may be that once he or she are in school that I may choose to go back to work, or maybe Aaron will choose to go back to work. And maybe I'll stay at home and do the independent thing slash be dad.

But during this critical time when both of them are home all day, almost every day, or almost all day, almost every day, you know, Declan does go to preschool. But you get my point. When they're not in a traditional, like, you know, kindergarten or above school, this is the best time to be home with them. And I will never get this opportunity again. So I've just got to try it. And I'm going to regret not with them. And I will never get this opportunity again. So I've just got to try it. And I'm going to regret not trying it so much more than I will regret failing to succeed at it.

I got a couple observations on that. The first is you had said, and I remember listening to you earlier in the show say, in just a very short time, he's going to be going to kindergarten. And what I wanted to say for you was in a very short time, he's going to be going to kindergarten. And what I wanted to say for you was in a very short time, he's going to be going off to college. And in fact, I thought that's what you were going to say, but, but you haven't been there yet. I have. And I'll tell you, I,

my oldest was in my arms coming out of the surgery, um, uh, just yesterday. And now she lives in LA and she's got a life of her own. And, you know, I go out with her and she asks me, you know, what drink I want, you know, so you'll be surprised how fast that happens, you know? And the second thing is getting back to your problem of saying, yeah, I've taken on too much. And, uh, the, the one advantage of this is even though you do find yourself taking on more than you think, and I think we can talk more about that if you'd like, but the advantage of all this is you still are in control of your time. So even if you take on a few more projects than you wanted,

that time that Declan really wants to play trucks with you, you can probably make that happen. Yeah, yeah, absolutely. And the other thing I've wrestled with a lot, and I think is probably worth unpacking at some point is, am I spending my time wisely? Because as it turns out, I've spent a lot more time on this YouTube stuff in the last month than I had initially intended. And I should probably set the stage a little bit more clearly. So a few months ago, it was late last year, by a series of funny and interesting circumstances, I found myself with a press car. So I got a car for a week, it was delivered to work, actually, and then picked

up from my home. And it was a Alfa Romeo Giulia Quadrifoglio. And if you're not a car person, suffice to say, it's like an $80,000 Alfa Romeo. And not knowing really what to do about this, I thought, well, let me write a blog post and make a video out of it. And I made an extraordinarily crummy video that I've put on YouTube. And then fast forward a couple of months, I think it was January, I had a different Alfa Romeo, their new SUV, the Stelvio. And then fast forward a couple more months. And last month in July, actually immediately after coming back from London, I got a Volkswagen Golf R. And actually, as I sit here today in my garage temporarily is a Volkswagen GTI. And so what's ended up happening is by kind of circumstance, I've had access to a bunch of cars that I wasn't necessarily planning on having access to.

And of course, I'm not complaining, But I'll get these cars for a week. And I'll film a whole bunch of footage. And then because I'm terrible at YouTube. It'll take me like a week to put the video together. And so I've been spending an extraordinary amount of time doing this. And what I'd be curious to hear you guys weigh in on. Is I am having a tremendous amount of fun. And one of the goals that I hadn't stated about going independent was being able to kind of like

pull on these threads of things I've wanted to do, but hadn't had time. And these videos are one of them. The problem I have though, is that even though these videos are tremendous, tremendous fun, I have earned precisely $0 from them and have probably bought between $200 and $500 worth of equipment specifically to enable these videos. And so it is, by every definition of the word, a passion project. And I see a future maybe two or three or four or five or six years down the line where maybe it is making serious money, like real money. But that's a long shot. That's arguably, you know, like winning the lottery. And so what I'm starting to feel guilty about only a month and a half into being independent is,

am I spending too much time on this thing, which genuinely makes me very happy and might pay off in the long run, but is also pretty likely not to pay off as well? And am I prioritizing poorly? Yeah, there's a lot there. I guess I can speak from my perspective, which is going to be a little bit different because I am a very spiritual person. So my faith kind of directs a lot of the things that I do. So I've got a spiritual why behind all my productivity things. I wrote a book a while back, and it has not been super successful. It is exactly the scenario you described where in a couple of years, you haven't made any money from this thing. But I don't even go back and think about should I have done that because

it was something that I felt compelled like I had to do this. And one of the things that I got from researching that book was the definition of the word passion. It comes from a Latin word called pati. It literally means to suffer. So what passion projects are, in my opinion, are things that hurt you to keep them inside. And I think that's the attitude I take towards my quote-unquote passion project, because there's a lot of stuff that I do that doesn't bring in a ton of money. And really what it comes down to is if I never made a dime from this thing, would I still do it? And obviously, you got to weigh that against the limited time that you've got available. And we talked about that already, you want to be there

with your family and everything that you're going to commit to is going to take time away from from that goal. But I think that's the acid test for me. It's not, do I like to do something? But do I have to do something? Am I going to suffer if I keep this thing inside? Yeah, and I feel like I've heard you talk about exactly that in the past. And I think it's spot on. And I don't know if I would suffer or not, but I take your point in that it is an itch that I definitely want to scratch and suffers a big word, which is why I'm kind of hemming and hawing.

But your point is fair that it is an itch that I really, really, really want to scratch. And when I do release a video, even though I can watch it back and see all the places where I screwed it up, I am still proud of the thing that I've created. the places where I screwed it up. I am still proud of the thing that I've created. Even that first one, which is terrible by any normal definition, I'm still deeply proud of it because I feel at least so far, and I've done three of these thus far, I feel like there is a progression and a path and a line. There's a vector here that shows that I'm on the right path. And it may not be that I, you know, I'll never be as good as, as top gear. And certainly I won't have the budget no matter what, but I feel like I'm getting somewhere with it.

And as long as I feel like I'm learning and progressing, I feel like it's a useful expenditure of time. It's not lucrative necessarily. It may be, but it's not today. Probably won't be for a long time if be, but it's not today. Probably won't be for a long time if ever, but it's useful. And, and I feel like nothing bad comes of expanding my professional repertoire, which I think is another thing you've said in the past, Mike, that, that even though I

don't expect to ever make a dime from knowing how to do a little bit in final cut pro who knows what will happen in a year or in five years or in 10 years? Just because it doesn't seem lucrative today doesn't mean it won't be. Now, maybe I'm just doing mental gymnastics to justify all this time I'm spending. And I guess that is kind of what I'm doing. But nobody has a crystal ball. There's no way to know what the future will bring. And certainly I didn't know. And I feel like I might've told the story recently on some podcast, or maybe I was just talking about it in life, but I remember arguing, not arguing, that's too strong a word, but, but having a tense conversation with Aaron, my wife about whether or not we should spend,

I think it was $150 on a road podcaster, like microphone and boom arm and all that stuff for me was 350, whatever it was, it was a couple of hundred bucks to get to get a podcasting microphone so so me and my two buddies could record a podcast about cars this was back in january of 2013 and we spent that 150 250 dollars whatever it was and i got a little bit of grief about it injustifiably like if i'm in aaron's shoes i would have given her you know if the roles were reversed i would have given her a bunch of grief about it too why would you spend all this money on a microphone for something that will probably go nowhere and fast forward five years and now i'm doing it professionally you know so you never really know where this thing is going to end up and that's how i'm justifying it to myself i think it's just i

need to be be aware and i i guess saying this out loud is in part convincing myself i need to be aware of the balance of doing this car stuff against doing the other things that are bringing in money today. And I just need to make sure I don't go off the deep end on the car stuff and ignore everything else. Yeah, if you're looking for justification, then I guess we're the enablers. Because in my opinion, progress, not perfection. You never can judge your stage of the journey against somebody who's been doing this for a long time. But it is important to recognize, and you talked a little bit about this, the skills that you've developed. And you have no idea what doors are going to open from doing this thing.

I wrote my book. It was not a success by any worldly definition of success. But that got me connected with Asian efficiency. Once I got there, I got into screencasting that got me connected with Don McAllister. And like one thing leads to another. Now I'm doing a podcast with David Sparks. Like I never would have pictured myself in this position. But it's because I, you know, I pulled the thread and I kept following it to see how deep the rabbit hole went and just looking for the next thing in the journey because you have no idea when you start what it's actually going to end up looking like.

Exactly. And just to follow up on one of the things Mike said on his very first episode as a co-host was, you know, bet on yourself. And I think that that's what you're doing in effect here. And that doesn't mean that betting on yourself on this doesn't mean that you're going to just stop everything and, you know, stop making your podcast and stop looking at, you know, maybe doing some 1099 work. You know, you're diversifying and this is the piece of it that doesn't have an immediate payday, but it's something that you feel you need to do. It's, you know, it's funny, I'm doing, I haven't really said much publicly about it, but I've talked on this show

how I'm transitioning from books to video products, and I'm going to start doing some YouTubes for it. And I'm doing them not to make money on them, but just to kind of have a channel so people can get used to seeing my mug on a camera and understanding that I make video products. And I've got a different use for it, but it's a piece of what I'm going to be doing where I have no anticipation of ever making

money on it. That's the other thing Gray told me. He says, you know, you're never going to make money on YouTube at this point, you know, and, uh, and I, I feel like there may be some truth to it, but then, you know, I look at Casey, I've watched your videos. I'm not a car guy, you know, um, you know, it's funny because in the tech community, we always get excited about the new computers and we can't understand anybody that, you know, drives the same six-year-old Mac and doesn't see why they need a new one. But I'm the exact same way like that with cars, you know, I drive a car until the wheels fall off. But I get excited watching your videos because they're kind of infectious and, you know, you're a great guy.

I could see this absolutely taking off for you or turning into something that you don't expect it to so does alfa romeo have an affiliate program yeah right if only i mean tesla does so you know if if i if i only had a tesla then maybe i could i could get some referrals there but uh but no i mean i i agree and and one of the unbelievable luxuries and i I guess a theme of this episode is me reiterating a thousand times how lucky I am and how appreciative I am of the people who listen to me do exactly this sort of thing. But one of the luxuries I have is that now that I'm not slaving away for the man, if you will, I am definitely I have I have more than I had before, and I have the ability to try. And I think as long as, and this is what I took from what you just said, David, as long as I keep it in check and don't go completely off the deep end, there's probably no bad that will come from this. If I'm refusing to record podcasts on account of video stuff, you know, podcasts like,

you know, ATP or analog or something where, where I am getting some amount of a paycheck from it. Um, if I'm refusing to do the things that are demonstrably lucrative, that may be a problem. But if I'm just trading off between things that I hope will become lucrative, that isn't necessarily a bad thing. And the other thing, the other motivation for continuing to do this car stuff is that I have accidentally ended up with a fair bit of momentum on this since quitting my job. And I kind of don't want to let that stop. You know, I don't want to pull back or pull up, if you will, and slow down from the sprint I'm in the midst of. I've been trying to go running in the mornings for the last several months.

And I can tell you that once you start to slow down, or at least for me anyway, once I start to slow down and go from a run to a jog or a jog to a brisk walk or a brisk walk to a casual walk, it's hard to get going again. And so to some degree, I feel like I've got a little bit of fire under my bottom and a little bit of momentum going on this YouTube stuff. So I just want to see it through and maybe in a month or two, maybe that'll all dry up and maybe, maybe I'll be out of cars to review and there'll be nothing left for me to do for a while, but I don't want to lose the momentum while I've got it. And that's part of the reason why I'm trying to push so hard. Yeah. Momentum is, is a interesting topic, uh, on the topic of

running specifically, I ran a half marathon in May. Oh, good for you. Thank you. Yeah, overtrained though, hurt my knee and I couldn't run for six weeks after that. And by the time I started running again, I went from 13.1 at almost an eight minute pace to three and a half miles at a 10 minute pace. Basically had to start over. I trained a year for this thing. And now I gotta, I gotta go from, from square one again. Yep. I totally hear you. And, and, you know, running is a whole nother topic I could go on for hours about, even though I'm a terrible runner and I'm extraordinarily amateurish, but, but it is in many ways a

metaphor for most of the hard things that I've done in my life. And, and I'm, again, I'm a terrible runner. I don't run very fast. I don't run very far. I'll usually do about a 5k. Well, when I'm, when I'm being good about it, I'll do a 5k three times a week, which is to say about, um, 10 miles a week. It's not that bad. I mean, your half marathon was what? 13. Is that right? Yeah. 13.1. Yeah. 13 straight. I'm talking about doing less than 13 over the, over the span of a week, but it's enough to get my blood pumping and keep me moving and make me feel like I'm not just a sedentary lump, you know? And so, so I have been, I have been very proud of myself and pleased with it, but nevertheless, um, it's hard. Like even if I skip just a couple of days or if I skip a whole week,

it's hard to get back into it, leaving aside my performance at it. It's just hard to get the motivation to get back into it. Even though once I get myself running, I do quite enjoy it. But I think part of the problem is I do it early in the morning before everyone else in the house is up because I feel like that's the best time to do it. That's least intrusive to everyone else. And, you know, rolling out of bed at six when I could, when I, when I could alternatively roll out of bed at seven, sometimes it's appealing to just stay in bed for a while. Yep. Got to do hard things. Yep. Hey, speaking of the hard things, we got to pay the bills. So I'd like to take a quick minute to talk about our first sponsor.

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A while back, you recorded an episode of Analog, which I re-listened to before we recorded this one. I think it was episode 134. And my impression from that episode, as you had recorded it, and you even mentioned this in the episode, that that was recorded before you officially left your job. And you were pretty high on the prospect of being a free agent. And so I'm curious now, you've been a free agent for a little while, is the honeymoon over? Oh, definitely not. Again, it's only been a little over a month. The honeymoon is not over, but reality is starting to creep in. And I mean that in a mostly good way. My fantasy vision

of free agency was, you know, Aaron and I had agreed that I would spend during daytime hours, I would spend, you know, roughly half of the day doing whatever I deemed as work and the other half of the day with family. and that fantasy has not been accurate which i think is by and large probably a good thing i've tended to work between four to six hours almost every day um and including some at night and including a little on the weekends which is another thing that like you know you guys and steven hackett has talked a lot about you know i'll never work on the weekends why would i i have all this new time during the week that I can do what I need. Why would I bother any other time? But as you guys have said, and as I internalized, but apparently did not truly understand, is that it's just different when you're a part of it, when you realize that everything is hanging on your shoulders, you're compelled to do things anytime you have a moment to breathe. And I don't think I'm as bad as some people are about it.

Like, I deeply respect you guys and Stephen, I'll bring up again, and Mike, actually, Hurley, all as people who tend to work a lot. all as people who tend to work a lot. And I respect that ethic, but I also don't want to, and you guys don't either, fall into the trap of anytime I'm breathing and not with the family, I'm doing work. And I'm not there. I'm not there yet.

But certainly it's been more work than I expected. And again, I think that that's mostly healthy. One of the best parts about it though, is the flexibility, which is the thing that I think almost everyone has said. And especially because I'm not doing very much consulting. And unlike you, Dave, I'm not doing client meetings and things like that. And I know you try to clump those onto a couple of days a week. But still, though, you know, my parents live about 45 minutes away from us. And usually once a week in the mornings, they'll come in and, you know, kind of hang with the kids and hang with Aaron to some degree.

And in the past, you know, Aaron would use that time to go grocery shopping or whatever the case may be. But now over the last few times they've done it, it's been nice for me to just say, you know, I'm going to stop work early or perhaps even not work at all this particular day. And I'm going to hang out with my family. And I mean that both Aaron and the kids and Aaron and the kids and my parents, depending on the context and just having that flexibility to just kind of blow off work for a while and know that the world isn't going to end and you're not going to get a stern talking to when you return to the office. That is amazing.

And so in that sense, the honeymoon is very much still here. That is amazing. And so in that sense, the honeymoon is very much still here. But again, it's been more stressful than I expected. And I knew to expect it to be stressful, 11 years now? And she is as easy a spouse as I can imagine. But I will only speak for myself. Our marriages still work from time to time. And it's one of those things where, you know, you propose and everyone thinks, oh, it's going to be magical. You'll never fight for the rest of your lives. And, you know, we fight from time to time and oh well you're having a baby you're finally having a baby in our case after many years of trying oh we're finally having a baby i will appreciate this baby i will have the patience of a saint i will never get angry at this baby and oh my gosh duckling can be so annoying you guys you have no idea he can be so tough and so it's one of those things i think where i heard you guys talk about i heard the two of you i heard jason i've heard steven and mike talk about marco i've heard all of you talk about it. And my brain understood, as I said earlier, my brain understood these things. But until you experience it, your heart doesn't really get it. Yeah. So what was the other than like the tendency to to want to work all the time and say yes to projects or say yes to too many projects? What's been the like the hardest thing to adjust to that

maybe causes that stress is it just the fact that like everybody is right there and it's hard for you you know you don't have that place where you can shut the door and you know i'll see you in a couple of hours to some degree certainly for the first couple of weeks that was real rough particularly for declan because he's only three and a half and it's hard for him to understand he's he's gotten to terms with what we call talking work and so when i'm doing a podcast he knows like don't knock on the door don't come to the to the office like leave dad alone for that time but when i'm not doing quote-unquote talking work it's harder for him

to understand and it's been it's been really tough when i'll pop downstairs for a second to get a drink or something like that. Oh, daddy, do you want to play with me? Well, yes, I do, but I can't. And I think that that's a balancing act for everyone involved. And I think there probably are times, I think it was David that said this earlier in the episode, there are probably times that I should just play trucks with Declan for a few minutes and then be like, okay, buddy, I got to go back upstairs and not say I've been, you know, a complete hard person about it. I don't want to swear, but you know, not that, not that I've been completely on, on, on flinching about it, but I've certainly erred closer to the side of nobody. I got to go back up.

I'm sorry. And I think finding that balance has been tough. It's also been tough when like aaron will want will want to run an errand that i know will be easier with me there say she'll want to go grocery shopping or something like that i i really want to be there to make it easier on her and she knows i mean she's a grown woman she knows exactly what i'm wrestling with but you know it's hard to say no to her and say yes to work especially especially because, again, with a couple of small exceptions, this isn't like 1099 work where there's anyone else waiting on me. You know what I mean? It's just whether or not my video gets out when I want it to or this podcast that it gets done as early as I want it to be or whatever the case may be.

So that's been really hard. I think there's the latent the latent stress of it has been hard uh without you know getting into the details we we definitely knew that this was a possibility so we saved up a fair bit of money and so you know if if podcasting goes away tomorrow it's a problem it's a big problem but it's not an immediate problem so that has that has kept some of that stress at bay but it's certainly more stressful. And, you know, the argument that Marco has made to me many times is that even if you have a traditional job, that could go away tomorrow. And as it turns out, you know, my particular employer that I just

left did do a series of layoffs over the last few months. And so it is even more true than in many cases that for me, my job could have been at risk, but it doesn't feel that way, or at least it never did to me. And so because of that, when you lay off yourself, exactly. Yeah, exactly. Right. And so that I think has been tough, but truth be told, it has been way better. The good has outweighed the bad by so much. And if the most of my problems is,

hey, you guys, you don't get it like this passion project that I'm having a tremendous amount of fun doing, and that I have been spending my working days working on where I get cars that I can use for free from from nowhere, you know, they just appear literally in my driveway from nowhere, and then disappear and I get to use them and I get to play with them and I get to make videos out of them. And I'm having so much fun with it. And I'm a little stressed about, you know, whether or not that'll make money. Like, come on, dude, this is you're living the dream right now. And so I'm trying to to to weigh there being there really and truly being a lot more stress in places I didn't have stress before, but also in places I didn't have stress

before, but also recognize the fact that I'm here with my family doing things I want to do and life could be so much worse. And I need to make sure that I, and in the family as well, but I am appreciative of that too. Yeah. You've got to stop and enjoy the ride a little bit. Exactly. It's hard. And like, I know you're just starting to take on client work, 1099 work. And the next challenge you're going to face, I'm guessing, is going to be choosing between client work where there is somebody on the other side of the phone saying, hey, have you finished that thing yet? than your own passion projects and the things that you want to develop on your own, which do have inherent value, but they don't have another person in the world bugging you about. And then suddenly you've got to balance those things on top of, I have that problem too. And it's not easy. Yeah. And I've actually run into just a smidgen of this so far. So I've only taken

on one client and it's only like something to the order of 20 hours worth of work. So it's really, really not that much. But it was a nice way for me to dip my toe into this water. And it's been funny because I have been trying to do my best to juggle doing that work to some degree, even in advance before everything is 100% locked down, because I knew that I was getting this car, as it turns out, as we record yesterday, and I will only have this car for a week. And so I know that I will not be able to, or I will, it will be hard for me to choose to do client work, which I could hypothetically push off if necessary over recording footage with the car,

which is going back a week from when I got it, no matter what. Does that make sense? You know, so I have this like hard deadline with the car. The client deadline is important and it's not soft, but it's something I think I could massage if necessary. And so I've already run into that kind of scheduling tension, for lack of a better word,

where I'm trying to make sure I'm doing the best for my videos, I guess. So, you know, to some degree, me as a client of myself as a video producer, I'm trying to do the best for my client that's asking for and paying for my time for them and just juggling all of that. And it's, again, it's a stress. It's not a big stress. It could be so much worse, but it's a stress. And it's a stress that I haven't had to deal with in a long, long, long time. That stress, that's the reason I don't work with clients anymore because I couldn't handle it. I kept thinking like, as long as I have this client project, that's the thing that I should be working on every minute of every day until it ships. I just couldn't get over that mental hurdle. couldn't get over that mental hurdle. Yeah. And I'm very lucky because the client is an acquaintance of mine. I wouldn't even go so far as to say a friend of mine. It's somebody I know through the internet. And so in that sense, it's been better because we have a rapport.

He understands because he listens to the stuff that I do. He understands kind of the things I'm juggling. So I'm getting a lot more leeway with him and his company than I probably would get otherwise. But it's still a balancing act. And I still want to do good work. I'm getting a lot more leeway with him and his company than I probably would get otherwise. But it's still a balancing act. And I still want to do good work. I'm still proud of the work that I do in all aspects of life. And so just because it's a friend that I'm doing work for, his company is still paying me real money. And I'm still being asked to do real work. I still want to do that work well and on time and on budget.

has to do real work. I still want to do that work well and on time and on budget. And so it's, it's, it's great because I'm easing my way into it, but it is not pretend it is the real deal. Welcome to free agency. Exactly. Exactly. But I mean, it's, it's been wild and it's, and it's fun and it's a learning experience too. I'm learning. And Jason especially talked a lot about this, you know, a while ago where he would take on, you know, writing projects for all of these different people, many of whom he wasn't sure he wanted to work with or, you know, the projects he wasn't sure were that compelling, but he just, he wanted to spread himself wide to see what sticks. And I think that's exactly what I'm doing right now. Not only is it nice to diversify a bit, but just, it's nice to know do i enjoy doing consulting because i was prior to my

last job i was a consultant but i was part of a firm so i wasn't chasing work i wasn't dealing with billing there were so many of those administrivious sorts of things that i was that i was uh secluded from or i was not dealing with and now it's all me. And so now contracts are something I have to worry about, which I've never had to worry about before. And it's not a problem, but it's something that I'm getting exposure to. So now at least like, again, I keep calling, calling up this doomsday scenario, you know, the podcasts just go away tomorrow. Now I have at least somewhat better of an understanding. Do I want to be an independent consultant or would I rather just go back to having a jobby job? And I don't know the answer to that today, but I'm getting a clearer view of it now than I, than I had a few weeks ago.

Yeah. Well, one, one advantage of doing it on your own is you get to pick who you work with more. Yeah. Yeah. Yeah. Working for somebody else. Yep. That's exactly right. And, and I haven't had too many offers of, Hey, would you do this for me? But I've had a couple and this one, it was exactly that. It was the right fit in terms of both client and work. You know, the, the particular work I'm doing is, is reasonably low stress and it's not that it's not important, but it's, it's, it's reasonably low stress. And so it's a nice way to ease my way into it. Yeah, you mentioned the lessons that you've learned. And I want to come back to that

topic in just a minute. But But first, I want to tell you about our other sponsor for this episode, which is Squarespace. This episode of free agents is brought to you by Squarespace, make your next move with Squarespace. Squarespace lets you easily create a website for your next big idea with a unique domain, award-winning templates, and more. It's super easy to get started. Maybe you want to create an online store. Maybe you want to create a portfolio. Maybe you just want to create a blog. Maybe you want to start a podcast. You can do all of that with Squarespace and you don't have to install anything. It's an all-in-one platform that lets you get your idea out into the world. So there's nothing to install. There's no patches

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squarespace.com slash freeagents and the code freeagents, all one word, to get 10% off your first purchase. We thank Squarespace for their support of free agents and RelayFM. Squarespace, make your next move, make your next website. One of the things that you mentioned earlier was that David, Jason, some of the other people that you know have given you great advice. And I'm wondering what's one bit of advice maybe that you wish you had had when you started?

And what's one bit of advice that you would give to somebody else who is considering becoming a free agent? Oh, that's a really great question. I wish I had thought about that in advance. You know, I almost wonder if the advice that I would give is that even if you really and truly believe what you've heard, like I believed what you guys have said about you're going to take on too much work and i believed what you said about you know you will still have stress it will be different stress but you will still have stress um i believed it but i didn't own it and i i almost wonder if the best advice i could give was even if you're sitting here listening to us and you're saying, oh,

yeah, yeah, yeah, I totally get that. I understand. You're not really, well, I wasn't anyway, able to understand until I lived it. And that's not a problem. But no matter how confident you are about how much you understand what your friends in your ears are telling you. Um, it doesn't necessarily mean that it, that it won't take you by surprise when it actually happens. And I don't know any way to, to really hammer at home other than that, other than to say, no matter how much

you think you get it, you probably don't. And that's okay, but you probably don't. And that's the advice I would give. In terms of advice I wanted to hear, other than that, I don't know. I think perhaps the best thing that happened to me, which again was mostly happenstance, was I left my job, I went on this trip, and then I got a car just a couple of days later. And obviously that's a particular set of circumstances for my particular work. But what I think that did was it forced me to get on the horse immediately. So let's say, for example, I left my job, went on this vacation, then came home. And I didn't have any particular urgent need to do anything it could be that sitting here now a month and a half later whatever it is i would still be just easing my way into

doing work oh you know yesterday guys i did three whole hours of work aren't you proud of me you know and and and so i think i think it was very helpful to have some sort of, and in my case, especially external deadline that was set for me. I mean, obviously I've, I had a lot of control over this and so I did set it for myself, but once I committed to getting that car, you know, a few days after we came back from the UK, I suddenly had a deadline and I had to go straight into, I had to go from 0% to a hundred percent pretty much immediately. And that was stressful, but ultimately I'm very thankful for it because it compelled me to really get a grip and get a

grip fast. And maybe, maybe you, the Royal you are not like that. Maybe, maybe you are, have very good self-control and maybe you would not just sit there and just screw around on Twitter or what have you, but left my own devices. Had I not had that immediate deadline, I think I would have done a very poor job of really getting myself cranking on the work stuff and doing so almost immediately. So to distill that into a soundbite, if you are going to leave your job, first of all, a trip, a trip immediately thereafter to kind of, to put a marker between your job and your new world that, that I definitely recommend, but, uh, more, more, uh, pertinently set, set up a project or a thing

or a deadline, do something that you are as much as possible compelled to deliver reasonably shortly after you start your free agency. So maybe that's a consulting gig. Maybe that's a book. Maybe it's a video. Maybe it's a blog post. Maybe you just say, I need to have five blog posts done in the first week. Whatever that particular thing is, make sure you have some sort of thing very shortly after you go independent, because that will really

force you to come to grips and come to terms with your new world, maybe even uncomfortably quickly, but you will ultimately be thankful for it. I think that's really good advice. You know, when I left, I had the opposite idea. I think it was kind of an advanced form of procrastination. But I wanted to take a week or two to like set up my procedures and have everything just perfect. So once I started really, you know, being a lawyer, for an independent lawyer, I'd have everything in place. But what happened was a bunch of clients left, you know, came with me from the old firm. And then a bunch of my friends in the community that heard I'd gone on my own started sending me clients. So just like you, I immediately went straight into the deep end and I had to backfill that other stuff. I had to slowly kind of put the procedures together

while I was still busy working. And, and, you know, in fact, Jason had said the same thing. I think when he first started six colors Colors, it was like an iPhone review or some big deal was going down. And I do think that actually, in hindsight, was a really good thing for me. Yeah. And obviously, everyone's different. And there's no one true answer for everyone. But I think I, if I were in your shoes, would have done the same thing, especially because my perception anyway of lawyering, if you will, is that so much of it is, you know, getting the administrivia. Like so much of it is just getting the perhaps fresh books set up and, you know, your contracts and this and the other thing. And to some degree, I had that, too. But I would have, if I were in your shoes, your shoes said to myself okay i've got two weeks and

i'm going to set up all of this stuff and it's going to be locked in it's going to be perfect but that two weeks would end up inevitably in my case be spent you know looking at youtube videos as in watching not creating or browsing twitter and so again not there's no one one answer for everyone but i am really glad that this is the way that the cookie ended up crumbling because it compelled me to really be an adult immediately rather than just cruise because initially i'd said to aaron you know i'm just going to take july just kind of ease into it you know reward myself for having worked so hard for for a very long time and been able to make this step and i a part of me regrets not having done so outside of the Europe trip, but, um, but I'm glad that I didn't. have just stepped away and relied on self-discipline and habits maybe that you had at your previous work. But for a lot of free agents, I think maybe they don't have those habits and you're just going

to use willpower to sit down and do valuable work every day. I think that's kind of a recipe for disaster for a lot of people. So I actually like the strategy that you accidentally used where you had that motivation. Because that's one of the things that I've mean, you accidentally used where you had that motivation. That's one of the things that I've been thinking about a lot lately is this whole willpower versus motivation thing. Willpower seems to me like something that you can assign after the fact, oh, I didn't do this because I didn't have enough willpower, self-discipline or whatever. But in the moment, like you can manufacture the motivation to do something. If there's an emergency, if your family's in danger, like all of a sudden, it doesn't matter if you are motivated or not, the motivation is there. You're going to do something to intervene and put out that fire. And I think that that's a really powerful tool,

not that you want to live in that constant state of emergency. I need to get this done or someone's going to be mad at me. But I think that's a really smart idea to create some momentum like we talked about earlier as you're making that transition. Yeah. And I think it worked out really well also, and I've kind of alluded to this moments ago, but it's worth stating that having a specific barrier between or dividing line maybe is a better way to describe it between old work and new work was also really great so as it ended up as i said you know i i stopped on july 2nd we flew to england on july

4th came back on i think the 9th or something like that and it was a very short trip but and it was absolutely vacation no no ifs ands or buts it was vacation but it was also a really great way to say, okay, self, that stuff that you just left behind is behind. And when you come back from this, this is the new world. the worst financial decision we've ever made. But I think it was in terms of our spirit, if you'll permit me to say so, I think both of us really needed that. Both Aaron and I really needed that to set this, to set, draw this line in the sand and say, okay, this is what was. And when we come home, there will be something new. And that doesn't have to be a trip overseas. Of course, it can be a staycation in the town in which you live. It can be a trip to go see your family or your in-laws or whatever the case may be. And it doesn't even necessarily have to be travel.

But for me anyway, it was super nice to have some sort of event, some sort of thing, which was not work related, where I could unwind, decompress and just say, okay, that's behind me now. Let's get amped up for what's coming. You know, and I would add a corollary to that. I hear from a lot of people that are, you know, quitting their jobs or thinking about it as a result of the show. And a lot of times the emails start out with talking about how miserable they are and how terrible the people they are that they work with. And I think when you turn the page like Casey's talking about, that's also a great time to say, you know what, all that stuff, let's say maybe I was mistreated before, but you know, it's time to forget about that now and time to focus on what I'm going to do. You know,

whatever has happened in the past, that's the past. Now let's just focus on the present and the future. Yeah, that's a really good point. I mean, as I said earlier, I left my job in a happy, in a happy way, whatever I should say, I wasn't leaving my job, you know, middle fingers high in the air saying the heck with you guys. I left my job saying, you know what, if for some reason this stuff doesn't work out, I'm going to call you guys back in six months or a year or whatever the case may be and say, Hey, you know, remember me? Can I come back? So I was not leaving my job feeling, you know, mistreated or, or, you know, being grumbly about it. I left my job because I thought that there was something better on the other side of the fence. And, and I think that even still, even despite that, having the dividing line between the

two was very, very helpful for me. So do you have any sort of, I mean, obviously the description that you just gave where you left your job and you left the door open to go back there. Did you have in your head, like, I'm going to try this for this amount of time. And if it doesn't work, then I'm going to go back. Or when you run out of savings or what was the thought there? Yeah, sort of so my my goal was okay short term i want to make it six months basically through the end of the year and unless something dramatic happens there's there should be no reason that that shouldn't work out again we

crunched a lot of numbers i lived in the numbers app on my computer for like two weeks straight trying to figure out, OK, you know, what what things do we enjoy that we really want to budget for and what things do we enjoy that we really shouldn't do? You know, do we really need a cable subscription, for example? And so far we've kept it. But you know what I'm saying? Like, you know, should we cut the cord? Should we do this? Should we do that? We probably shouldn't go out to eat all the time on the weekends, which we do because we enjoy it. And even though we aren't going to like fancy restaurants, I'm talking like Panera Bread or something like that, or McDonald's even. But nevertheless, it adds up if you do it a lot. And so, you know, as I'm crunching these numbers, I'm figuring out, okay, well, there's no reason it shouldn't last six months, but I'd like to see six months at the least.

six months at the least. And then my, my, that wasn't even like a reach. That was just a, okay, if, if, if I can't make it six months, something really went wrong. But my goal is I would love to be able to make it until Declan is in kindergarten. And again, he's three and a half now. So I, what is that two or three years? His, his birthday is right on the cutoff so i think he'll enter kindergarten when he is almost six so basically and he's almost four now so basically two years we'll just call it two years for the sake of conversation at a minimum i would love to be able to make it two years and at that point if i can't make it anymore it's gonna kill me that i couldn't last until Michaela is my daughter is in kindergarten. But at least I will have made it for for the transition from her from, you know, infant lump into person. And I mean that in the best way possible. I mean, infants are just kind of there, they don't really do much. And

she's becoming ever more and ever more a person every single day. And so by the time that Declan is in kindergarten, she will be be basically Declan's age. And thus, if I can last that long, that's my goal. I consider that to be my goal. If I can last until she is in kindergarten, which is basically five or six years from now, that is my stretch goal. And if I can get until both the kids are in kindergarten, I'm going to be really, really pleased. both the kids are in kindergarten, I'm going to be really, really pleased. And even if the day she enters kindergarten, I go back to working a traditional job or perhaps Aaron does or whatever

the case may be. Even if that's, even if that very first day of school is my very first day of work, I am okay with that. I will consider that a resounding success because I was able to be there for the kids when they were there with me. And, and if I can make it that long, that will be tremendous. Does the idea of going back to a job, I mean, does it give you a reaction at all? I mean, are you really against it or you're, you don't really care if you have to? I mean, it sounds to me like you're willing to go back, which is, I think at this point for me would be really hard. I am, I am willing to do what it takes to feed my family. And I don't mean to imply that you're not by any stretch of the imagination. I have no doubt that you would go, you know, you would,

you would go back in a heartbeat if that's what it took. But I think that right now I have not been independent enough to become unemployable. However, you asked me that same question in between six months and a year, assuming everything works out like I hope. And I'm pretty sure I'm going to be pretty well unemployable at that point. Like I can already, I can already feel it building within me. What do you mean I can't just blow off work for four hours to hang out with my family? What? Why?

You know, what do you mean I have to worry about time off? Like, what do you mean I have a limited amount of pto days and granted i mean to be fair anytime that i take like a morning off i try to offset that with working you know through an afternoon the day before or after or something like that so i don't want to paint this picture that i'm just working you know an hour here and an hour there just for the fun of it but but nevertheless there's nobody to yell at me if i do take a day off. And, and so, you know, the whole idea of like managing PTO like that already paid time off in case you weren't familiar managing like time off that and having there having been a

limit or having to deal with a limit of time off like that repulses me already. And I'm only a month in and haven't done anything. Like we've never taken a vacation in the last month. You know, we didn't do anything since, since Europe. And so despite the fact that I don't really have to worry about PTO because I haven't taken any, just the thought of having to worry about it is already deeply repulsive to me. Yeah. I mean, it's interesting. I have a friend who has worked for many, many years for an aerospace company and he now is at the point where he gets like a month off every year.

And he is always, you know, it's like they're pushing him out where he gets like a month off every year and he is always you know it's like they're pushing him out the door to take a week off once in a while and i i have accepted as a free agent i am never going to have that luxury you know it's just you are always doing stuff and i i guess this comes back to that spreadsheet conversation that you know you need to make money and if you're not doing the work then nobody's doing the work. But at the same time, there is an inherent freedom to it in the way you can schedule your time. Like if you want to go down and say, okay, Declan, we will play trucks today. And you take a half hour to do that. And then you go back to work. There's nothing wrong with that, where when you go and report to the man, it's a lot more difficult. And going back to that

spreadsheet, I do think it's remarkable how often freedom starts with a spreadsheet, you know, so many people, so many people. But I do also think that that process of creating that spreadsheet is one of the reasons why you say yes so often once you get out on your own, because you're very aware of what the numbers are. And there's a part of you, we just had a guest last month, you know, um, and Shin, who was talking about in her mind, she, it was a point of principle to her that she got as much as she made as much money from her jobby job, uh, going independent in the first year. And it wasn't that she needed the money. Well, I'm sure everybody needs money, but she didn't need that exact amount of money.

But I think she wanted to prove a point. She wanted to be able to talk to her family and say, yeah, I'm on my own, but I'm doing just as well as I was before, or I'm doing better. And I think that is definitely a reason why you feel a pressure to say yes, at least in my case. Oh, absolutely. I couldn't agree more. And I'd actually like to double down on the spreadsheet talk.

Everyone's financial world is different. And I'm not interested in any one particular person's financial world. And your financial outlook is different as well. But I found for me that looking at it unemotionally and looking at the numbers, both in terms of what is my expected income versus my expected expenditures? And additionally, you know, looking at whatever Aaron and I had chosen to save in advance of this, like how long can we last if literally I do not make a dime starting today? And for everyone, that threshold is different. Maybe for you, Dave, you only needed a month in the bank before you felt comfortable enough to

go independent. Maybe Mike, you needed a year. Maybe I only need six months. But whatever that number is that makes you comfortable, and this is actually, to be honest, this is even applicable if you're not a free agent. Being able to look at your bank account and say, you know what, I can survive a month. You know, if I get laid off today, I don't need to worry for a month. Obviously, I will worry today. But you know what I mean? Like, i don't need to worry for a month obviously i will worry today but you know what i mean like i don't need to worry for a month and for aaron and me it wasn't

until we had a reasonable amount of time in terms of money so a reasonable amount of money that can be translated into time in the bank that we felt comfortable doing this. And I don't think in a million years I would have gone independent had I not known that, okay, if everything dries up and I need to find a job, I don't need to find it yesterday. I need to find it in a month, six months, a year, 10 years,

whatever the particular numbers may be. And I cannot stress enough that having, and this is not news. I mean, I've heard you guys say this before, but having some amount of money in the bank and knowing, and this is where the spreadsheet comes in, knowing how much time that money will literally buy you is extremely important because it will either tell you it's too soon, it's time, or you know what? It could be time, but just wait another couple months and then

you'll be you know two times better off or three times whatever the case may be and so for me anyway having that having that oh crap money in the bank made made me way more willing to do this than I would have been otherwise yeah and we did an episode 29 is all it's called the spreadsheet and I'd recommend listening to that if this is news to you. But the, but I do think that, you know, that, that runway calculation is important. I was lucky, I guess, partly as a result of the fact that I'd waited 22 years to do it. You know, I, but I, so I had a client base. I had people that I knew would, would come with me.

So I, I didn't need a lot of runway. That's true. That's true. I wasn't come with me. So I didn't need a lot of runway. That's true. That's true. I wasn't going to have months where I didn't make any money. And I had an existing side businesses that were earning money. So it really wasn't that hard. I feel sorry or I have empathy towards people who are thinking about making a move and they don't have, like if they have a client-based business they want to start, but they don't have clients yet. I mean, that changes the calculation in a lot of ways. And you know, it's just stuff you have to think about. And like for you, I think you were okay too, because you also, your primary source of income was already existence. It was the podcasting

revenue. That's what you were looking at. And you do need some runway for some of this other stuff you're working on, but you have enough solid income coming in from the other stuff that you've got that runway. Absolutely. And it's one of those things where I'm enough of a worry wart that I want to be prepared for my financial world to dramatically change tomorrow. And maybe you, Dave, you, Mike, or you, listener, aren't as much of a worry wart as I am. you, Dave, you, Mike, or you, listener, aren't as much of a worrywart as I am. But I wanted to know that if everything stopped, I wouldn't be up a creek immediately.

I will obviously be up a creek without question, but it's not instant. And so having the knowledge of, and I can't stress it enough, I mean, that money effectively is buying you time. And so having a knowledge of whatever my particular amount of time was, be that one week or one month or one year or one decade or whatever, knowing at least being aware of how much time I would have helped balance that equation for lack of a better way of describing it. So you're still up, still up a Creek, but at least you've got a paddle. Yeah, actually, you know what? That's, that's a tremendous way of describing it. So you're still up a creek, but at least you've got a paddle. Yeah, actually, you know what? That's a tremendous way of putting it. You're exactly, exactly right. But I do think legitimately, when it comes to this free agent stuff, paranoia plays a role.

Yep. The difference is Mike and I publicly share our paranoia every two weeks, but we all have it to a certain extent. I mean, that's how you stay a free agent. Yep. And, and I think it is healthy. It's, you know, again, one of the things that I'd heard everyone say is that you are still stressed. It's just different stress. And I think that that is extremely true. I will take the stress sitting here now over the stress of, Oh God, I've got that meeting with that boss that I don't like or, oh, God, I really don't want to work on this thing that I have to work on. And one of the luxuries of being a free agent, as you guys said, is that you don't necessarily need to pick up. Oftentimes, you don't need to pick up work that you don't want to, or at least if everything's going well.

Right. And so I will take the stress over the stress that I had at my jobby job. But it is it is not a stress. It's not stress free will take the stress over the stress that I had at my jobby job, but it is, it is not a stress for, it's not stress-free living by any stretch of the imagination. Yeah. But you know, just remember all those lottery winners are super miserable. Yeah, that's true. I I've actually said for years because I am terrible with money. The, the only reason we've saved a dime in, in, in our entire relationship is because Aaron is very good with money and I'm terrible with it. And so i have said to her for years that if we ever win the lottery i i will i will give her all of the money and don't ever give me a dime which of course will ruin everything but i i i

god i would be ruined if we won the lottery come on aaron i i need at least two aston martins i mean why that's not unreasonable is it and plus we mean, there's no reason we can't buy a building that has 34 garage spots. I mean, I only have three cars now, but we already have three on order. That's reasonable, right? You need it for your YouTube channel, after all. Exactly. Come on. Be reasonable, Aaron.

I need it for my work. It's for my work. Oh, my goodness. So you've been in it a little over a month now. What is the hardest part about being independent for you? Diversifying, which is maybe, I hope that doesn't come across as smug. I don't mean it to. But as you said a moment ago, I do already have a lucrative thing that is making me money

and that if I'm smart, will continue to make me money. But it, it's scary to me that I don't have a, I don't have a very reliable plan to diversify. I have plans. I have this YouTube stuff that we spoke about quite a bit. Um, I have a little bit of 1099 that I'm doing. And I also, and I've talked to you, Dave, about this a lot. I've, I've also contemplated writing a book about this particular flavor of development that, um, that I, that I like to do. And so all of these things could be lucrative and could help me diversify, but it's, it's stressing me out and kind of freaking me out that I don't have anything that is already

starting to indicate that I'm diversifying. I guess the consulting kind of, but you know, say for example, like if the YouTube channel was making a hundred bucks a month, let's just throw a number out there, which we'll probably never will from what I gather of what you earn on YouTube. But for the sake of discussion, the YouTube channel is making a hundred bucks a month. Well, that isn't much today, but 150 starts to add up to 200 starts to add up, you know, all this, I could see the snowball growing, you know, or the snowball rolling down the hill, and I can see it growing. But as of today, as I said earlier, YouTube's made me precisely zero. And so I think it's really stressing me out that I haven't diversified. And I would love to diversify more. And

maybe that means doing a lot more consulting than I had planned to do. Maybe that means that I need to work even harder on the YouTube stuff. But diversifying would be nice. And that's not necessarily what everyone would want to do. And there's also different kinds of diversifying. You could be a lawyer that has one big client or a consultant that has one big client. But what happens if your big client goes away? You know, say I'm doing, let's say, for example, I'm doing consulting work for my old job, which isn't the case. Let's just say, for example, that they contracted me to do,

you know, 30 hours a week of consulting at my old job. Well, that's all well and good. But what happens if they say, well, okay, we're done with you, Casey, let's, let's move on. If I don't have anything waiting in the wings, then I'm not diversified. So, yeah, even if I'm, you know, you could be diversified even within one line of work. You can be a diverse consultant. What I'm talking about is being a diverse professional, but you could be a diverse consultant and that helps as well. And so just being diversified is stressing me out pretty bad. being diversified is stressing me out pretty bad. Well, if you'd like a little affirmation,

I have to say for someone who is as early on the journey as you are, uh, you're asking a lot yourself, a lot of the questions that it took me a lot longer. That does make me feel slightly better. It is hard though. I, I, you know, getting back to the top of the show, I think, um, uh, the, one of the, just the easiest trap to fall into, and maybe the trap you're supposed to fall into, honestly, when you go out on your own, is saying yes too much and taking on too much work. It does, however, have some side benefits. It gives you the ability to find the stuff that you actually enjoy doing. And it kind of goes back to the adage. I remember somebody told me when you're hiring people, be quick to, you know, be slow to hire and be quick to fire. But, you know, it's the same thing where, you know, you bring these projects on.

And if you realize it's not the right thing, be willing to jettison. You know, even if you said yes to too much, at least take some time to be willing to get rid of the stuff. I, for me, a big move for me was when I stopped becoming, stopped taking on litigation work, which is, you know, kind of, you know, my objection, your honor kind of stuff where you fancy, which was very lucrative. It was the most lucrative thing I did, but I realized if I wanted to make the Max Parkey thing work, I could not, I could not like go all in on litigation, which, which consumes all your time. So, but yeah, I think just being open to the idea of jettisoning some of that stuff as you go forward is something you should, you should remember. Yeah. And I think, you know, coming back to what do I wish I heard

when I was just becoming a free agent, no matter how much I had a plan for how I was going to spend my time and what I was going to work on. My mental model of my plan for my new working life was that it was a straight line from A to B. And I think that the reality of it has been that it's been a kind of meandering, curvy line that's going from A, hopefully in the direction of B, but it's been less of a straight line than I expected. And in and of itself, that can be a little bit worrisome, but by and large, I actually think that's healthy because I can see that when I veer left over here, that's not for me. When I veer right over there, ooh, that looks great.

And I can refine my path through the wilderness to beat this analogy to death as I'm going. And I think that that's okay. And in fact, perhaps even healthy. And, you know, just as you had to realize, Oh, maybe litigation isn't the way forward for me after all. And I need to do a little bit of consulting and do a little bit of this car video stuff. It may end up that tomorrow I decide the car videos aren't for me after all. And I think I need to just try it. And again, as I said, I think early in the episode, just pull on these threads to see, is this for me or is it not? And taking that kind of meandering path from A to B is probably healthy in the grand scheme of things. I think a meandering curvy line is actually a

lot straighter than a lot of free agents. I think you're like one of those big squiggly balls where you try something that doesn't work, you change course, you try something else. I think that's a really important point. Not necessarily, I guess, as advice to you, but generally speaking to the topic of being willing to jettison things. I think it was last episode, David, we talked about the personal retreat thing and the three questions that I asked myself, what should I keep doing? What should I start doing? What should I stop doing? And I make myself answer that question.

What should I stop doing? Like pick something to stop doing every 90 days, roughly, just so I have the margin to say yes to some of these things and pull some of the threads and figure out, you know, where, where they're going to lead. Yep. I completely agree. You know what? I can't wait to have Casey back in a year or two after you've gone further down this road and you're a famous YouTuber. Maybe you won't have time for us. But I really can't wait to hear how it goes because it feels to me like you are really asking yourself the right questions. And I feel like it's going to be a great trip for you. And you and your kids are going to have a lot of fun over the next few years.

Well, and I appreciate it. And, you know, I mean this in the best, most friendly way possible. If I don't have time for the two of you, then that is a great sign because then things are going really, really well. But before we end, I should make plain that I have had a lot of conversations with a lot of friends and a lot of people. And a lot of them with a lot of friends and a lot of people, and a lot of them have been private conversations, but I've had the luxury of hearing conversations with you and Jason and you and Mike, Dave, that, that have helped me to make this journey and helped me immensely. And I don't think it is possible to overstate how helpful this podcast has been and and especially you know you guys individually um

both you know you mike jason all of you guys have been individually in helping me on this journey and i would not be sitting here talking to you were it not for this very podcast and for all the conversations that we've had uh independent of show. And so my deepest and most tremendous thanks, you know, it is, it is a no small part because of this podcast that I am able to go out to lunch with my family, you know, more often than I ever would have before. In fact, that's what I'm going to be doing as soon as I hang up with you guys. And, you know, just think about how wild that is, that it's because of this podcast that my son will remember this time when daddy was home all the time rather than remember the time when daddy came home from work and i had

10 minutes with him before bed you know what i mean and that's because that's because of the two of you guys it's because of jason and it's because of a lot of other people too but it's it i wanted to publicly say thank you to the two of you guys and and effusively say so because were it not for you guys i would not be here now and my my family is much better off because of it oh man you just slayed me i had like a witty remark jeez no i really appreciate it well we we it's a labor of love for us and you know it's a it's also a public bloodletting as always but you know, it's a, it's also a public bloodletting as always. But you know, we do what we have to. And I do wish you the best of luck. I'm sure you're going to be successful with this. And I, like I said, it's fun, because I feel like we've got you in a little time capsule here

one month in, and we're going to have you back in the future at some point to see how everything goes. Yeah, I want to put the stake in the ground right now. So in two years, when you're famous, instead of micro famousfamous, Casey, we like Casey before he was cool. I would love to be. I mean, it's so weird, the world in which all three of us live, that I am even micro-famous,

you know, and that you guys are micro-famous. But yeah, if I'm somehow like legitimately famous, you know, and I talked, I think it was with Mike, I talked about, you know, this YouTube stuff

is probably not going to go anywhere. But what if it ends up with me on like top gear in 510 years, like it could happen, not likely, but it could, you never know. And so yeah, if, if that ends up happening that I'm on the world's most well known, you know, automotive program, then you can say you knew me when and I'll still come back, darn it, I'm still going to come back. If you don't, we are going to publicly shame you. No, please do. Just so that is fair trade no but thank you guys for having me on it is a pleasure and genuinely and truly it is an honor so thank you so much all right so where can people find you right so you can find all of my stuff at my website which is caseyliss.com you can find me

on twitter sometimes when i'm not begrudgingly on Twitter, you can find me at Casey Liss. That's C-A-S-E-Y-L-I-S-S. I am dabbling with micro.blog. That's, I'm just Liss there. Instagram, YouTube, just look up Casey Liss. You'll find me and it's all linked from my website. And yeah, and so the YouTube, you can go from the website. So everybody go sign up for his website.

You can, whether or not you like cars, Casey is an entertaining guy. I don't really care that much about cars, but I watch all your videos. Well, thank you. I appreciate it. Yeah. Yeah. What do I have to say? I'm not a good enough YouTuber to know that lingo. What do you have to like, uh, like, and subscribe and pound that bell or something like that. I don't even know what the kids say these days. You know what I'm talking about? I'm shooting some YouTube video and I don't have the guts to say that. I haven't yet either, but I guarantee it's only a matter of time before I do. So we'll see. I've resisted so far.

All right. We'll see you next time, Casey. Thank you, guys. Okay, so we are the free agents. You can find us over at relay.fm slash free agents. Thanks to our sponsors in this show. That's our friends over at FreshBooks and Squarespace. And we'll see you all in two weeks.