Helping a Dev Double Down on Creativity • Coaching Session

Ever feel like working in tech today is just being a robot? Nobody wants you to truly think for yourself and be creative? They just like you to work within the box that they've set up for you, keep your mouth shut, and get the job done that they asked you to do. Well, nobody knows this better than Charlie. He's a client of mine, and I'm going to share a real coaching session with you today that I did with him. Charlie and I have worked together over the last year and during that time he shared his story which you might relate to too. Charlie's an artist and early in his career he got the opportunity to start a business where he employed other creatives and helped them do work in tech and get paid a fair amount. Over time that company got bought and since then he's kind of struggled to find his footing of where to go next. So, when you listen to this story today and you hear the coaching session I'm about to share, I'd encourage you to try to put yourself in Charlie's shoes. Try to see if there's any parallels to your own situation in your career. And I think you might find you're inspired by getting some ideas from what we talked about today and how some of the suggestions I give Charlie could directly apply to your career, too. Hey man, how's it going? Hey, pretty good. Um, yeah, thank you for mean today. This is I was looking forward to this for like a week or actually it's been about a month, I think, since you reached out. Okay. So, I don't know if it would maybe be helpful for you to give me a little bit of an update first on what's changed since we talked last time, but that ultimately, you know, I'm going to try within this hour to help you however I can with let's say one hopefully at least one issue. So yeah, what happened was uh I you know had gotten laid off from a job that I was sort of doing for about 10 year plus years and was kind of in a weird self-discovery mode of like what do I do next? what am I what who am I like what am I you know and uh and so a lot of self-discovery a lot of figuring out like oh you know I have a lot of need to do creative work and that like that comes in the form of making art so another thing is like I used to own a business doing 3D animation and right uh that was a part of a couple of uh things that I was doing but so kind of like realizing oh I really like doing that. I want to do that kind of work. And that, you know, that business ultimately was about creative consulting and sort of kind of realizing, oh, you know, I love doing consulting work. That's just my bread and butter. I know that to be true. I know that that's what I want to do. Um, and so then kind of wrestling with this kind of realization, well, life has changed a lot since I was a, you know, uh, 20some and now I have a family and I'm trying to support my family and, you know, having a stable job actually is nice. And so kind of like waffling between well am I doing uh am I going to go like do you know back to being a consultant and doing this sort of freelance style life or am I going to like try and build my image up and like try and like get another job like a career like a career job. Yep. And ultimately uh what I found is it's actually really hard to just get into uh the career path job for me u mainly because I have this very broad skill set and it's not like specialized in any way and a lot of job uh either like through networking or through you know just general job hunting, they're looking for very specialized individuals to fill in Sure. in a lot of cases. Um, and so yeah, I think what I ultimately found was just networking, talking to people, I found that there were, hey, there are people who are interested in working with me and just doing contract work. So, I did kind of go back to doing freelance work. Um, okay. And it's actually interesting because uh right now I actually have these two kind of things that I'm balancing. One of the contracts that I'm kind of working with is very menial work. It's very like repetitive like do the same thing over and over again. Um and then the other one is a lot more like free form and creative. And so it's sort of like it's more like hey like design this feature for this application or like hey like figure out how to build this pipeline so we can do this

repeatedly um and like bring in more people and it you know I'm kind of balancing both right now and I'm trying to kind of make sense about do I need both can I do one or the other and then I guess like ultimately where we left off and I think it's kind of the realizing it's more like a lifetime question to kind of address is like how to uh get creative uh work in my life and do I do it through a career or like personal kind of projects or personal kind of like just for me kind of stuff and so that's I'm still answering that question. I think the biggest re revelation I had was uh just how challenging like promoting myself is as an individual. Like I would much rather just be working than like spending time promoting myself. Um so I'm trying to flex that muscle like uh I'm working on like building a personal site and having a personal project that's tied in with that site. So those are some things that I'm going through right now. But yeah, it's just a big puzzle to solve. Like, do I focus my creative energy into my career or into my personal life? And I don't have a good answer. Well, thanks, man. Thanks for sharing the update. Yeah, I'm hearing a lot of the same themes that we talked about last time. So, I remember when we spoke previously, I was asking you what amount of creative work you were doing currently in your life that was separate from your career. How are things going there today? Do you find, you know, and I know you're I believe you're a father. Is that right? Do you have children? Yeah. Yeah. Are are you having are you getting any opportunities to do any kind of artwork or creative projects either with your children or you know just on your own today or is that kind of had to take a little bit of a pause because of the job search urgency? You know, I have been able to incorporate that. But it's interesting because now that I'm I've got these two kind of contracts going on, I can see how easily that slips away. When I have like say 2 3 hours at night to myself, um there's like well I could spend that 2 to 3 hours like working on building a website or like you know figuring out this 3D printing project that I'm trying to do. Um or I could try and solve this hard problem. and this in this work rellated contract. Um that's kind of like that's causing this sort of itch on me that I'm like I really want to figure this out. What I notice is like okay like the thing that I actually need to be focusing on the most right now is just time management and like really kind of buckling down and being like these are the hours. These are the hours this there doesn't go you don't go over. And so I know that that's also been just a lifelong problem for me. I I'm very passionate person that wants to just solve problems. And so if someone hands me a piece of code and they're like this doesn't work, why? Um like that's kind of dangerous cuz like oh like if I have any interest in it at all like and so that's kind of the other thing. It's like, how do I remain passionate but sort of detached where it's like, okay, I care about these problems, but I'm done at like 5:00 p. m. Like, it's over. So, that's the that's kind of like another element that I know is going to just be a constant battle. I hear you making some statements that I don't want to say they're not true, but they might be worth exploring that like this is always going to be a lifelong thing. It's battle. I'll probably never figure it out. Um, you know, that's not to say that I know better than you, but it does sound a little bit like absolutist language, which sometimes when I do the same thing in areas of my life. Uh, my wife is very adept at calling me out on that and noticing it. That's good. Um, that's good. So, a question I have is it sounds like there's two potentially different things we could maybe dig a little deeper into today and you can help me figure out which one might be most helpful. On one hand, I'm hearing, you know, you described time management that this is an area that you are improving, you want to improve in. And I think what I'm hearing there is you desiring to say, I want to work my job and have my job's time be my job, and when it ends, I can compartmentalize it. I can put it on the shelf, so to speak. and I can use, you know, the time that's available to me once I've already, you know, done my duties with my wife and my children when I have creative time for

myself and truly use that creative time and use my time effectively. Uh, we So, we could explore any challenges you've had with that, any areas I could possibly help with that. That that's one thing I'm hearing. M the other thing is how secure are you feeling in your career in general with the freelance approach you're taking? Do you feel that you are moving towards a either a brand or a value proposition that is something that you can grow and you feel clear about or are you still kind of testing the waters? And the reason I asked these two things is I find for myself when I'm not feeling confident about the direction I'm headed in my career. Mhm. It's really hard for me to be fully present when I'm trying to do like music write guitar parts or sing. Um I do the best I can, but sometimes there'll be, you know, these background threads, no pun intended, kind of running. Yeah. you know, gosh, I you know, I don't know what my next contract's going to look like. I don't really know where I'm headed. So, I guess sort of the question is, how much do you feel of your mental space today is being occupied by frustrations with time management versus questions about just sort of the long-term direction of your career, if that question makes sense to you? That totally makes sense. And I guess, you know, I know myself. Um, and I know what I'm going to be doing uh work-wise. Like I think it's like that's very clear to me. It doesn't really like it. Yeah. My career is weird. Uh, I'll say that. But as long as I have something to work on, I know where the path is. If for some reason I Yeah, go ahead. Can I just cuz I I'm hearing something that doesn't totally match what you said earlier and I think this could be helpful. So you're saying I know where I'm headed in my career as long as I have something to work on. But then but then you described earlier I have two things I'm balancing with work. One project which is very I don't remember the exact wording you used but kind of repetitive. Yeah. And then another one that does give you some more ability to have a creative input to the design. When you say, and I I'm not trying to challenge you, I just trying to get clarity. When when you say I know where I'm headed in my career, is there maybe like a larger umbrella of how you're looking at it that those two different things still fit under? I think so. Yeah. And I mean I think like the it's actually having these two separate contracts is actually perfect for me because it's experimentation. It's like can I just do menial work? Can I, you know, have a creative presence at the workplace and still have creative energy for myself? And so I think like obviously like it would make more sense to experiment like one of these things at a time rather than both at the same time. Um yeah, I don't think that I totally thought that all the way through. But I do think it's like I think having them both is showing me what would this look like if I did if I had just like a just do the work, you know, like don't get in involved into anything higher than just what I'm putting on your plate. Let me ask you this. Back when we worked together previously, earlier in your career, you were in a situation where you were able to work in a way where you were somewhat of an advocate for other creatives and they worked somewhat under you. And you were able to do work that you felt like allowed you to be more creative at first and then as time went on, you were kind of more involved in the administrative or just running the business because you were helping all these other people. You know, you were trying to make your business be successful. And then over time that company, I believe you guys got bought out or you sold the business and and then your work kind of transitioned more into that feeling less meaningful sort of version of work where you kind of had to compartmentalize your creativity within work and just put your head down and and you know do what you had to do. Um, so from my perspective, which I'm not you, this is just my perspective. Uh, it sounds like you've run this experiment before in your career already. You've already had a job where you had more creative control and you had felt more meaning in the work and you've already had a job where it didn't feel as meaningful to you. So, I'm just curious what's when you say you're this is good for you because it's an experiment. What are you hoping to learn about this

sort of version of running the experiment that you maybe didn't learn last time? That's a good question. Um, I guess this time it's more about what do I actually want out of my career? Um, and I think like what I'm finding as I try to like build my myself uh up as I'm like looking cuz you know doing freelance that's also I'm also kind of exploring sort of the job market and like trying to look for work here and there. Um but like I have having run a business for you know most of my career plus employment never spent any time like doing self uh promotion like I've done promotion for my business but like doing it for myself is a whole different thing that I that it's almost like the business actually protected me in a way where I could pro promote things I could promote stuff without this real complicated nature of like you know what do I believe and how does that mix in with like my work the people I interact with and so it's like to have this shield of a business like gives you sort of this like no this is what I'm building like this is what you see this is what I want you to see versus when I when it's just me it's a little more vulnerable it's like oh I have to like say I'm really good at this but maybe I'm not you know and that's the experiment I guess it's like this is this time it's not there's no business it's just me and so there's sort of this nature of like well in order to do that like I have to know myself really well and also be vulnerable in a way that I haven't been vulnerable before when you had initially started that business or let's say just leading up to it were you doing that more creative type of work as just you before you know hired other people yeah I was doing that here's where the disconnect is for me a little bit. You know, I I totally agree with you that life is a you know, sequence of self-discovery. I'm learning new things about myself every week. Sometimes good, sometimes bad. Yeah. At the same time, I feel like, you know, and this might be oversimplifying things and maybe you disagree, and that's okay. You can disagree with me. I feel like I know you pretty well and that what you want is you want to have work where you're able to express yourself creatively and you actually also have a heart for other people who are able to express themselves creative. Oh yeah. So, a question I have for you is I think you did a really great job of articulating how conceptually you looked at your business before that, hey, it's a business. Um, it's not a personal brand, so to speak, which is similar to what I do, I guess. Like, you don't have to be publicly the face. I'm Charlie. I'm the face of this, you know, movement, this effort, this capability. It's a company. And I can kind of hide myself a little bit behind. here's what we offer, but you don't have to know like me that I, you know, publicly it's me, Charlie, who I am. Would you have any interest in or how do you feel about the prospect of trying to establish more of a name for yourself publicly as someone who helps creative engineers find ways to be more creative and express their creativity through their work? Meaning, and I'm just throwing an idea out there. I'm not saying this is what you have to do. Uh meaning like the thing people pay you for is not to come in and apply your creativity to a software engineering problem. And that could still be the most exciting thing to you. So like we're going to come back to this. I'm again I'm being very careful here not to project that this is what you should do. I'm just throwing an idea out. Sure. Um, but the idea being that there's other people out there, some younger than you, some older than you, some your age, who are in a spot where they're very frustrated because they're very creative just like you, and they're struggling with an ability to express themselves creatively through work. And it sounds to me like you figured out how to do that. Now, you haven't that in a constant reproducible way. And that no, you know, to pay your bills, you're having to sometimes take work that just pays the bills and doesn't fill you up fully creatively. And I feel like for many of us, at least for myself, there's a journey of that. It's like you get a job, you just pay bills. Hopefully, it's work that doesn't suck. Then over time, you get better at that work and you

start to step back and go, is this what I really want? And then you kind of thrash and freak out and try to decide is there a way that I can kind of do something that's more meaningful to me. But you're but there's no evidence that that's possible yet. The only evidence you have so far is the only way I can make this money is I have to not get to be as creative as I want. What do you think about the prospect of like if people actually paid you either to coach them or if you had some sort of process or tips or you know I don't know what that would look like yet. But rather than you having you know companies evaluate hey does Charlie have enough tech skills that he you know matches our requirements of the tech stack and and you know he can convince us that he's an employee. It's more you're building trust with individuals out there who are engineers or they could even be I don't know if it's limited to software engineering. could be anybody almost in office work that is trying to find ways how do I embrace my creativity within projects cuz again it sounds like you found ways to do that and still protect your free time which I'll say being fully vulnerable uh I try not to speak to the audience too much you know I struggle with that making time for myself creatively with work so I'll pause there well I don't even have any interest how do you feel about Yeah. I mean, I think it I think it's interesting. Uh what the thought that ran through my mind is like are you is this a hiring offer? No. Uh but uh I mean like it's an interesting prospect and I think like uh there are definitely a need. You know, I think you know I hear from people that they struggle with like how to be like creative in their work um a lot. And so I I've never really even thought of that. Like that's like an interesting uh avenue to look at because that's so different from Yeah. like hey let me help you do the creative work for you versus hey like you're a creative person like but it seems like you're struggling with that kind of energy or like how to think that way like you know here's some ideas. So yeah I mean that's an interesting business prospect. I have never considered. Yeah. Most of what I've ever thought about when I'm helping other creatives is just like it's mostly automation. It's mostly like how can I get you to just stay creative and stay out of all of this mess of like buttons and gizmos and software switching and like settings that you have to set up because the project is structured this way. That's one thing. But then the whole other element of like how do you um people who are also struggling with like how do I be creative in the work space? Yes. Like you know how to help them. And so that's very fascinating to me. I actually uh it's got kind of got some gears wearing cuz it's like I that's an interesting problem. I don't even quite know how to solve but I could imagine it. Just to kind of flip back what you were saying about like is this a hiring offer? Um I mean I I talk with and I think the more of these I put out, I plan to continue doing one-on-one coaching. I'm just looking at doing some different stuff, too. Uh you know, I often tell people cuz I often meet people and they're like I they like what I do and they could maybe even see themselves doing maybe not exactly what I do, but some part of it. And sometimes I feel like they get this impression like I don't want to infringe on what you're doing. Like I there's you know what how many millions of software how many tens of millions of software engineers worldwide like I can't help everybody and nor am I qualified to. So, so like I've talked about creativity on my YouTube channel, it means a lot to me, but it's but you know, for there to be somebody who their whole charter in the world in a way is to help people with that problem, you know, they're going to be a specialist. You know, I might open the door that that's something people should be concerned with and you know, maybe through coaching with me, I help them with that. But, you know, I'm always also looking for people who I can point people to if they get at a point in their coaching with me or they just need help. You know, like with marketing and sales, I can do a lot of things to help people get started and really, you know, break through certain things to kind of get themselves going. But at some point, you know, there's when people really want to invest and they want to go to that next level with their business, let's say, they're going to want to hire someone other than me, you know, to help them really go to that next level. So, I just say that to say when I began working for myself, uh, I realized I'm not the guru or the expert at the thing I'm helping people with. I'm really just a step maybe or two ahead of the person I'm helping. And that's really all you need to be. And I've found the more that I've helped

people, the more it's helped me help people. So, and I'm not trying to project on you, but you might be feeling a little bit, at least I'm picking this up a little bit, that like, you know, well, I could help people, but, you know, I'm still kind of dealing with this issue myself. I'm still trying to find a level of balance. get better at improving, you know, my ability to be creative with work. That's actually a totally legit okay place to be in. In fact, it's I think personally that's a more authentic place to be in. And I think that's very attractive to this has been my experience. It's very attractive when you find someone online. This is what my clients tell me at least who is not trying to say they have everything figured out because we all kind of inherently know. Nobody does, right? Like there's so much crap I have no clue about, man. I mean, and I probably never will, but it's mostly just takes somebody deciding this is, you know, it's a decision. I talked with Ben Thorp about this, uh, another person I I've coached. At some point, if we make a decision, and I'm not saying this is the decision you have to make. We're just talking about this the first time today. But um you know I made a decision 7 years ago that I was going to help struggling software engineers learn to stick up for themselves better, consider working for themselves, just find ways to basically increase their value proposition, have more leverage over employers, be healthier. It was it was kind of a mess cuz again I didn't I didn't know at the start of this exactly what I wanted to do, but I did know that was more interesting and appealing to me and it felt more meaningful than continuing to make companies that are very successful even richer, which you know, I'm not anti- capitalism. I should be upfront about that. I'm not anti- capitalism. But, you know, we all choose how much do we want to kind of just have of our job be making the richer versus finding something that truly enriches people's lives. And I'll pause there. I've said a lot of stuff. Um, I just I guess to nutshell, you don't have to have it all figured out. Uh, if you did want to help people with this, my experience has been you're going to get even better at what you're improving now by helping people. What are your kind of thoughts about some of those concepts? Um, yeah. Yeah, I mean I think what I what I know is to the point of like honesty like that's been my bread and butter like since I started my own business because what I found is yes you can say you know everything but at it come it comes to a certain point where you're like okay well I actually just need to be honest with you because I don't know the trust is such a hard thing to gain back and when like you're caught in a lie, like you're not going to you're not you're just going to be in a bad place in terms of getting like being able to get trust back. And so, uh I think it's totally true. I think there's just like you said, so much noise out there that really kind of makes it seem like, oh, like we know exactly what you need to learn to be the best software engineer. like we've we know exactly what language you don't know and now you need to know like you know it's like and it's marketed with so much fear of like oh you don't know this you're nothing like you know and it's like what if I actually instead of looking out looked in and just like really tried to know myself and know what it is that I'm good at and yeah just like I think it's wild how much of what you're doing I see as just like almost like having a therapist where it's like sometimes what the help that people need is like hey like you're valuable like you are you just as you are you know and it's not necessarily oh like you have this degree and you have the these many skills like no it's it's literally like you as a person are valuable and so you know whatever you're getting into as a software engineer I feel like I see a lot of talented people who just are so down on themselves and it's like why? Like you're great. You're like you're brilliant. You're doing amazing stuff. Kind of riffing off what you're already saying. I think it's totally feasible to for me to start like something like this like a helping other creatives. Um and I think there's a lot of ways I can imagine doing that um now that we're talking about it um that I didn't quite think of. So that's really cool. Um, I think the other thing that I that I think about a lot is how I've kind of struggled with that creative element of just like how do I be passionate

with the work that I'm doing and be creative at work? Um, but don't get so tied up with the work itself that like I have this sort of ownership of it. That's just taken like a decade of time to like figure out how to do creative work but not be attached to the work itself. when you're young, when you're doing creative work in any realm, um you know, you feel really passionate about what you're doing. And to so to be in community with other people saying like, "Hey, this doesn't work or I don't like any of this or we need to change all of it or half of this is good. We're going to get rid of this other half. " Um this just like that's like heartc crushing. And so what I see is like a lot of software engineers that I worked with, they're either been they've had their heart broken or they're like, "Yeah, they're just like, I I've got the poker face. I don't care. Like I'm not going to reveal anything. " And so it's sort of like for me as a person like I just I need to have that part of my being with me like whether I'm doing personal work or like doing that like for my career. So well let me ask you about this. So I hear two motivations over your career that I you know we talked about even in the coaching prior that we've done where you have both a motivator to be creative yourself and that's in work and personally. And then you also have a motivator to be of service to other people. I definitely hear that in your story. You ran a business for a while where you partially kept the business from what I remember running as long as you could because you felt like people in digital art and animation and you know some of the people that you employed aren't paid well enough and so you tried to run this business to make it more financially viable for people to be creative. I mean that that's not a sacrifice that a person makes if they're just out to be as profitable and you know have their own needs met to basically uh run a company where that's sort of your charter and all the issues that you ran with administratively and the stress that you took on to try to keep that going. You know, I think it's probably healthy that was a phase of your life and your career and maybe you're not stuck in it anymore because it sounded very stressful. when I began taking steps towards this career coaching thing and doing a YouTube channel even though it was a mess and I was figuring it all out and I was burned out and you know my whole story. Yeah. uh having something that I was at least start that you know something that I was starting to build towards that was mine that was h you know nobody could say ah that that's just a little too creative Jamie I don't want you to do that you know like if I wanted to be try something really offthe-wall I could now I don't consider myself some like super creative person that isn't what it's about but it's just about you know I've talked about how I was in a band in high school in early college years and you As long as the band members, we all agreed we liked how a song was going, there's nobody to be like, "No, you know, that song's a little too much this, right? It was kind of a very free area to be creative. " Yeah. Uh if you started to take steps towards something like this, what I found is when I have something like that, I'm moving towards, it makes it easier for me to do my day job for as long as I have to do it. cuz I think you know I had to do consulting contracts still part-time while building this coaching business for about four years. Uh it made it easier for me to not get so hung up if the day job, you know, things that I was hoping would go one way didn't or like areas where I found an opportunity to be creative within work, I didn't get to get that opportunity. I was able to let go of that a lot easier when I had something else. I was building towards. So if this was something that you wanted to explore, I guess a couple questions would be one, what are some of your sort of fears or objections that kind of come up in your mind that make this something that you wouldn't want to take action on if there is anything? And then kind of coupled with that, what would be some actions that you could maybe start to take to experiment with this and see if this is something worth pursuing? I mean, I think it would mean for one thing, I would have to sort of abandon the project uh create a project that I've got going on the side to like be more about less about me and then more about like helping other people. Um, which makes me feel like there's ways I could envision that happening, but like maybe it makes sense for the personal project to finish that a little bit to then, you know, branch off of that and use that as sort of the basis for like, oh, this is how I could

help other people um who want help with creativity. And I think then the other element to it is just sort of like what format would that look like? you know, would that just be like consulting like this um where it's just like sessions or would that be more like uh some structured thing or would that be like some throwaway like Instagram post, you know? So, it's like thinking through that I would probably then kind of want to start thinking about well what is the goal? What is the intent? And I think that's how I'd start forming that. And then you know that's and then I would kind of move from there to how do I make this visible? How do I have this structured in a way so that people can see it and um you know interact with it and respond to it. That's kind of like how I would think about it. I mean, I think like when it comes to like new ventures or new businesses or new projects, the fear part is for me, especially with like starting a new business per se, is, and I think you could actually speak to this a little bit, is the fear of like what if my initial idea is wrong? What if it changes? Um, and sort of this sort of like kind of like the starting problem of like, well, I don't want to start until it's perfect. like I totally know what I want to do and the market needs and what value I want to give to be like, you know, it's going to change and to just kind of like to start somewhere. Um versus like, oh, I have to keep planning it. thinking about like perfecting it and make sure it's perfect before anyone sees it. Um, I think that's the stuff I have to shut off and be like, "No, like I have this idea. I have this concept of like what I want it to be. Let's start and just, you know, know that it's like, yeah, it's not perfect, but it's what I want to be doing. " And kind of adapting as you go is kind of what I see you doing. And yeah, what I would do um if I to were to start like a you know help creatives like uh kind of business. So well hey man I mean the good news is it sounds like you know one of the biggest mindset challenges that you face and you actually know that it's a mindset challenge. It's not truth. It's not reality. Meaning you do not have to have it all right up front. In fact, I would say if you expect that of yourself, you'll never do anything. Right. Yeah. If somebody were to go back and find original Reddit posts from like seven years ago and you know I had different YouTube banner artwork and I had a different icon and I had different thumbnails in my first 80 videos like some of that stuff was so horrible and so cringe and I don't claim to be some great graphic artist. I'm not. I didn't go to school for it but I've improved. I can do some basic thumbnails. People do click my videos. Um, now I'm not going for these super shocking, you know, cuz I'm not an entertainment channel, meaning like I'm just out for views. I'm trying to help people. Uh, so it's a little bit different approach to how I market myself. But my early videos are horrible. Uh, I didn't know how to talk to the camera. I would ramble. I still do, and some people like that. If I look back at what it's taken to build where I'm at today, it's been a series of just experiments and failures and learning and pivoting and trying and hopefully assuming I stick with the direction I'm headed now, you know, 3 to 5 years from now, I'm going to look back at this moment with you right now and go, man, you were, you know, you had a lot to, you know, me, to learn on coaching and wow, I can't believe how much you've come since then. So, you know, I guess I just encourage you to say I think what's challenging for us, at least this is what was for me as an engineer is like, you know, I had a 20 year or 19 at that point career when I started what I'm doing now. And it's like the more success in a way that you've had in your career up to a point, I think it's a little bit harder to become a noob again and permit yourself to go. What was it like when I got my first professional job? And I took that job and I remember I loved my first job out of college where everybody I work with was like, "Jamie's an idiot. " I mean, just meaning like they didn't expect much of me. They're like, "He's right out of college. He's, you know, he's 20 years old at the time. " They were like, "We're not going to trust him with a whole lot. " The fact that I didn't have that high pressure was so freeing. You know, there were things I didn't even know. I didn't know. And I just encourage you and you know anybody who's thinking about doing this like you can re experience that freedom of being new and

having less expectations on yourself if you go in the direction of trying to, you know, maybe pursue something that you would truly own. Because here's the good news. Nobody online is going to expect you who's brand new to doing whatever you're going to do to just come out the gates, you know, perfect delivery, perfect framework, have all the answers cuz guess what? I don't have that today and I've been doing this for seven years. So, I just want to encourage you, man. Um, you have a real heart for creatives. Sure, you're still figuring stuff out, but like, you know, and I know we didn't get into a lot of details on on, you know, the artistic work that you've done and stuff. I think that's maybe for another time, but this would be something that would be a real benefit to people, even potentially people outside software engineering, again, people that just kind of have corporate tech jobs. Let me just take the pulse again really quick. I'm pretty good at and I tend to get excited about talking to people about doing this type of stuff, but you know, that's kind of my MO. I'm trying to free people, encourage them to take a step. How much am I projecting this on you versus that this is something that maybe is even that interesting? Like, is it mostly just my enthusiasm rubbing off on you, or is this something that you might actually be truly interested in? Yeah. I mean, that's a good thing to gauge. And uh I don't know. I would say there's maybe a little majority of you projecting, but you did spark something. Good. Yeah. Um, like you did spark something cuz it's like oh wait a minute like what if you know it. So like anytime someone throws me a what if it's a very exciting moment for me because I'm like wait I've never thought of that like what would that look like? And so I mean you're do you are kind of handing me this nugget to like examine and to really kind of like look at. So I don't know. It might happen, might not, but it is something. And it does kind of touch on this other thing that I've been thinking about a lot as just like a business prospect, which is like how to help elderly with technology. And sort of my big kind of bias against that is like so much of that sphere is elders getting taken advantage of. And then just sort of like the security implications of doing that kind of work because it's like people are willing to just share their password with you. It's like you can't do that like don't do that. But that's how you get this sort of like bond. And so it's like well like I want to do I would want to do that professionally but like this is weird like you know so there's you know I have been exploring some other ideas um and it's kind of tangentially related um a little bit to what you're suggesting which I think is a little more there's less strings attached to it in my mind like it's very approachable but yeah I think like also kind of going back you know starting a business when I originally started a business I'm remembering Now that I was very lucky that was actually to solve a very immediate problem which was that we are doing this work as employees and there is no one to manage us or supervise us. We need to just do this ourselves and own this. Y and so to make a business now it feels like that magic that uh lightning in a bottle you know situation doesn't exist. And what I actually need to think about more of is like what is the problem you want to solve and to really just kind of use that energy to launch something. Um because that because my mind realizes that you know that business existed because you're trying to solve a problem and that's an immediate like well let's do this kind of energy versus like oh hum and ha like what do I want to do you know like maybe I'll do a business maybe I'll do that you know it's like so I it's almost this is kind of like advice for myself actually in this moment of just like well what if instead you just thought about the problem you wanted to solve, you know, form the business and then and use that as the launching energy. And yeah, maybe it's it shifts rather than like I'm going to spend all of this time like really kind of trying to figure it out before making the jump. Um cuz I think like that's something I notice with myself right now is it's just like well I have to really think about it. And kind of research the market and understand what the problems of doing that work will be look like and what like you know some of that due diligence. Yeah, it's it is but I think I found too that like that's I just get stuck in that space. Um especially when I'm trying to think about, you know, a new project or a new business kind of idea or something like

that. So, well, one suggestion I have is uh I don't know if you've already seen this or maybe even read it, but one of the books that I recommend to people and I'll explain in a moment uh the part of it that I think could be useful. Have you seen me mention the book called Start from Zero by Dane Maxwell before? No. Okay. So yeah, that would be something that I can definitely recommend to you and I recommend uh I made a video, I think it was last year sometime about kind of validating your business ideas or just good ways to come up with business ideas. And most people I think who are trying to sort of start their business I think um do by accident and you kind of did in that you stumbled into a business where there was a problem already. Uh is I think we tend to think that we know There's a problem that exists and it probably does exist, but we maybe are overconfident a little bit in our ability to articulate to our customers. Sure. That we understand the problem the way they see it, the way they conceptualize it in their mind to the level that we can instill confidence that we can solve it for them. And so that book uh you know, and it's got a lot of stuff in it. It's for entrepreneurship. Um, and some of what we're talking about is a little bit different than what he talks about. But one of the things that's really valuable in that book is he provides a I think it's a five question framework for a conversation that you can have with potential customers or clients as a way to try to understand you have this theory like let's just get real tangible about it. Let let's use the example of uh you helping the elderly with like protecting their security and using technology. You know, if you were to follow Dne's kind of framework, you would reach out to some people who are, you know, older and in this situation and you would ask them these five questions and through asking them these five questions, you would learn how do they see the problem? What do they think it costs them? what would they be willing to pay like financially to have the problem solved and like what workarounds are they doing you know you it basically helps you really understand like how urgent is this pain you know and there's also a book called spinelling it's an older book I've mentioned this to people it's a it's a sales book but one of the key things is spin is an acronym and the I in it is implications and what's interesting about the spin selling book is, you know, you if you've ever seen like The Wolf of Wall Street or like any of these really popular uh kind of like sales movies or you know, things out there, it's always talking about like overcoming objections and all this stuff that works for lowpriced products. But when you're offering like what I do, multiple thousand coaching packages, tricking people by overcoming real objections that are legitimate that they have does not work when you're doing things like I do. It just it falls on its face. Nobody's going to buy anything from you. So that spin selling book is really awesome because it helps you help someone else understand what are the implications of you not having this problem solved. And I think we as engineers are really good I believe we're really good at helping other engineers understand the implications of technical problems. Like if I'm on a project and I want to put forth a suggestion on some dependency injection pattern or cloud service we're going to use or you know third-party graphics library. I can help other engineers understand hey without this here's what we're losing with this here's what it's going to buy us and they can conceptualize that and they can do the trade-offs and it can help understand the cost of not supporting my idea. But when we get to business people, a lot of times we don't translate the implications to business value problems. Yeah. And so really what I've been teaching a lot of people through one-on-one coaching and I talk about some on the channel is like as engineers, we're already really good at making strong arguments for things. The problem is we always keep it at the audience of engineers. And if we can just start to practice translating that passion we have for convincing people to other audiences, that's really what it takes to really understand a market and sell things. So I just say that to say whether it was helping people with protecting their time and and being able to invest in creativity outside work, which is a awesome cause, or you know, helping people who are older that are, you know, at risk of being taken advantage, again, awesome cause. Uh, at the end of the day, if you want to make a business out of it, and it's not just

like what you kind of ran into where it's like one company has one expensive problem, they hire you, it's a clearly defined business problem for that company. If you want this to be a repeatable problem where there's a whole market of people that you can kind of continually help, I believe it is really important to do some market research and some due diligence to understand the problem space. It doesn't mean that is it isn't a legitimate problem. It's just when you go through kind of Dne's approach, what's great about it is it helps you understand how your customers look at it. Cuz I' I've talked about this on YouTube when I began helping people 7 years ago. I have a language that I use to describe workplace dysfunction and burnout and you know all those different things. When I met people, I learned a lot of engineers have different words that they use and they have different ways of describing their experience than I do. And if I try to talk about how I can help them in my language, it doesn't land for them because it's not close enough to their real experience. So, I know I'm getting into sales and marketing a little bit here, but none and none of this is like, you know, rocket science. This is totally stuff. I mean, if I can do it, anybody can do it because I'm not a like saleserson by nature. Yes, I was a consultant for 10 years and that did help me a lot with talking persuasion, but so yeah, I guess I'd just say kind of to try to nutshell a little bit of what you're asking, what I'm saying is um I think a potential good next step for you would be maybe get a copy of that book. You can find it real cheap, like a paperback on Amazon. Um, I'll give you a heads up, which I tell most people, the first half of the book is very like mindsetty, and some people can be a little, you know, like, man, come on, get to the meat and potatoes. And if you want to skip that, that's okay. Um, but, you know, if you get to that part where he talks about really validating the idea and exploring the market opportunity, and there's a lot, it's a whole book, right? There's a lot of stuff I won't get into today about it. Then maybe pick one of those two audiences. or if you get time, you can do both and find ways to identify people who could be your potential customer. Try having this conversation with them. It'll be a great way for you to practice just talking about the problem space that you're even theorizing you might help people with and finding out. You might find, hey, there's even problems there that I didn't even know. I thought the problem was this. It's actually this other thing. And maybe that's even just as exciting. Or you're like, nah, I don't want to do that. Right? You'll never know until you talk, right? No, totally. So, we're kind of at the end of the call. Uh, I think this is probably a good place to stop. If there was one more thing you wanted to talk about or ask me before we kind of wrap up, uh, is there anything else I could help you? Hopefully, this was helpful. Um, yeah, I think I think, uh, you know, obviously like the time management stuff would be nice to talk about, too, but that's another that's like that's a whole another session as I see it. Um and uh and but in terms of this, no just like I what I really appreciate is the sort of like hey like you know yourself you know that you know just finding a job like is not kind of like what you are really super jazzed about or interested in like you know this about yourself then you know explore other things. What else could you explore? um is sort of kind of what I've been given today, I think. And I think that that's actually that's super valuable because on the side of doing these contracts and things, I I have been continuing to just like, well, let's apply for another job or let's network and see if this goes anywhere, but not to be that jazzed about it or interested in it personally. And so just kind of giving just a little spark of like well what if what other you know things have you thought of like that you could do as a business or as like some sort of freelance consulting kind of thing cuz you like doing consulting like how do how could you make that work? So I really appreciate that. Oh happy to man. No it's been really great connecting with you again. It been way too long and again thanks for doing this. Yeah. If I can leave you just with one more word of encouragement, it would just be I know you're taking care of your family. Uh I know you have responsibilities. You know, when I coach people and just in general, even on YouTube, you know, I I don't want you to feel that I'm trying to, you know, pressure you into doing something rash. I think you should be measured about it. you know, if you feel that you need to continue to invest in certain activities you're doing to keep you employable, I'm definitely not telling you to stop that. Uh I guess I will encourage you to say maybe part of the reason that you're challenged with time management is first of all, you're working two jobs. Let's just be straight up about that. And second of all, the encouragement out of that though is if you know you can work two

jobs and somehow still find some time to be creative. There's a lot of people me who I get challenged with doing that with one job. Okay. Um so like if if you want to pursue one of these new ideas, I think an advantage that you have is you've already proven to yourself that if you need to work two jobs and keep the wheels on with your family, maybe it's a little rough, right? You can do it. Now, is it optimal? Is there improvement? Certainly. So it, you know, if you did get to a point where you had, let's say, at one at some point one job and your other job was building whatever it is for you, this new path that you want to be on, you know, you can summon that energy, you can keep it together. Is again, is there going to be improvement that's needed? Sure. But like, yeah, just want to flip that back at you, man. There's a lot of people that have not cracked that nut, so to speak, in their life of how to make that work yet, and you have. Ah, maybe I think I'm still working on it. So, right. And that goes back to what I said at the beginning of this though, like of course you're a work in progress and of course it's not perfect. You're a human being. I am too. But what I'm seeing in you is you do have an ability in that pe other people I coach some of them do not have that yet. that ability even with the limitations that you feel that you have and even the imperfections that you're saying that you have with your ability to manage your time. I'm saying there are people that are worse off than you with that. Well, I will say getting laid off really helped uh to at least re realign and rebalance and be like, "Okay, this is me. This is what I need. This is what I'm willing to give. " So, and so, you know, like checking doing, you know, the weekly check-in of like did that align with like what I'm saying, what I'm telling myself, and what I've said is is going to be truth for me, which is this is me, this is what I'm willing to give. So, awesome. Yeah, just doing that constantly. So yeah.