Soft Skills Engineering - Episode 438: Software job after prison and working 60 hours per week at age 20 and feeling unfulfilled

Episode Date: December 9, 2024

In this episode, Dave and Jamison answer these questions: I am a first time caller and full time listener of your show. I was released from prison a year ago and I coded for 18 years straight on all sorts of stacks as part of my job requirements in the pen. Imagine the irony when I discovered what codepen was. A dev told me about an opening for full remote/full stack web dev at their company. I’ve used the tech stack before but I have a non-traditional background to say the least. I’m not worried about being qualified but I have never worked in a team and I have always been responsible for production. I work for a large retailer in a non-coding role. I’m also doing some freelancing on upwork/fiverr, but the pay is low and the jobs are not fulfilling. I was self-employed before I was incarcerated and I know how to beat the pavement and get small time work, but this is an opportunity to work at a real software house. I don’t even care if it’s a feature factory, I just have loved coding since I was 14. What do I do? I am confident in my skills and ability to deliver under pressure (in a place that has pressures you can’t imagine). I have a cover letter, but a bad resume and no open source projects from this millennium. I do have a reference - a Captain I worked for said he was willing. However, the opportunity was unexpected and I have not prepared anything. The dev who brought me the offer was a casual friend in IRC and he told me that my resume was mentioned in some meeting. I know you have suggested in previous shows that having someone get your foot in the door is the best way but I really think that feels gross to me. Anyways, longtime listener of your show and first time caller. In fact, when I was in prison, a few years before I was released we finally got tablets with an incredibly limited amount of content. Your show was one of a few on coding but I really enjoy your take on the soft skills because even though I worked in a non-traditional environment, teamwork was always the focus and I listened to everything from square one (took me a long time to get there). So thank you for your podcast you don’t know how many times I could sit in my cell listening to your show and disappear from my cage. Sincerely, Names have been change to protect the guilty Second time caller from NYC! I previously wrote in as an 18-year-old CS graduate (Episode 332). I’ve focused intensely on work for the past 4 years, consistently working 60+ hours per week. I always assumed that this approach to life would eventually bear fruit, but a couple months into turning 20, I’m realizing that I haven’t really done anything memorable besides work (which is a scary realization at 20). While I like working hard and want to ensure the success of the company I work for, I also want to feel like I am living. How have you struck the balance between work and non-work in your lives, and how has that related to the culture of the company you were working for at the time? I should also mention the company I work for (early stage, well funded) does have a culture where it’s expected to work everyday, and 60 hours is approximately the minimum expected.

it takes more than blaming any prod outages on the computers being tired from eating too much turkey this is episode 438 of the soft skills engineering podcast where i am your host jamison dance i'm your host dave smith soft skills engineering is a weekly advice show about all the non-technical things that go into the technical field of software development like anthropomorphizing computers as a way to blame your mistakes on their weird personality i guess on things that actually you did yeah yeah i mean this will release after thanksgiving but we're recording it pretty close to thanksgiving so i wonder how long the window is like how long do the computers get tired from eating too much turkey right

hopefully long enough for this episode to be relevant yeah yeah probably yeah do you want to thank our sponsor dave oh yes this episode is sponsored by work os who has launched a ton of very useful stuff that you should know about as a software developer. We'll tell you about it during this episode. Would you like to thank our patrons? Yes. Yes, I do.

Yes, I would. I would do. Thank you so much to... This question comes from an anonymous listener. They say, Hi, Dave and Jameson. What are the best planning tools you use? Well played.

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formerly known as object object the owner of williamangel.net uh we can't actually say this name out loud nice travis braden canes john grant joe grosberg if you would like to join this illustrious crew. Dave, don't gloss over this bit. Maybe it's different. Go to softskills.audio and Cody Sale. Oh man, it just gets better every time. Just have to say, I want everyone to know we read every word and even tried to pronounce the emojis. So none of that was ad-libbed or modified. This is beautiful. If you're confused, it is a clever trick that our patrons have played on you. Yes. If you want to play a clever trick like them, you can go to softskills.audio, go click support us on patreon put in a name or a fun thing to make us say and you'll get a shout

out every week you also get an invite to our it's a small price to pay i i would challenge you to find anywhere else that you can go put in your credit card and type something and have someone say it on a podcast i'm trying to not say all the ways you can do that on other don't look into it there are no other ways to do this yes just do this one you'll also get an invite to our slack team and which you cannot get from any other way um and and come hang with the cool folks in there they're a delightful crew one might even call them illustrious yes uh our our listeners and our they call themselves illustrious now i guess technically because the shout out says illustrious yep yeah what are the

best planning tools i'm gonna answer this question because i worked for a company that made a planning tool for a while shortcut is great i worked for them so my bias is is i don't know i used to work for them i think linear is another one that gets a lot of buzz i actually use that right now they're the new hotness um they're the new hotness very very slick i think shortcut might have a bit more kind of like structure and opinion and maybe scales a bit bigger to bigger teams and linear is like the fancy you just it's just beautiful and smooth and everything seems fast and i think the best justification for linear is that if you want your product to be slick and world-class and amazing you should probably use slick world-class amazing products internally and it will inspire

you i think i mean i think that's a big part of the pitch right like look how awesome this is you'll get awesome from using this yeah also i think just now we're coming out of the era where every technical tools website was the linear site i feel like that's just they kind of took over for a few years there what do you mean was like people were copycatting in them yeah it just felt like everyone was copycatting their design because why not that's a big flattery yep dave do you want to read our first question yes i do okay this comes from an anonymous listener is that correct yes that is correct all right this is a little bit of a long one but we love this story so we're gonna just read the whole thing so everyone buckle up i'm gonna do my best

long form reading voice i am a first-time caller and full-time listener of your show i was released from prison a year ago and i coded for 18 years straight on all sorts of stacks as part of my job requirements in the pen imagine the irony when i discovered what code pen was that is very well said a dev told me about an opening for a full remote full stack web dev at their company i've used the tech stack before but i have a non-traditional background to say the least i'm not worried about being qualified but i have never worked in a team and i've always been responsible for production i work for a large retailer in a non-coding role i'm also doing some freelancing on upwork fiverr but the pay is low and the jobs are not fulfilling i was self-employed before i

was incarcerated and i know how to beat the pavement and get small-time work but this is an opportunity to work at a real software house i don't even care if it's a feature factory i just have loved coding since I was 14. What do I do? I am confident in my skills and ability to deliver under pressure in a place that has pressures you can't imagine. That's amazing. I really can't. I have a cover letter, but a bad resume and no open source projects from this millennium. I do have a reference. A captain I worked for said he was willing. However, the opportunity was unexpected and I have not prepared anything. The dev who brought me the offer was a casual friend in IRC, and he told me that my resume was mentioned in some meeting. I know you have

suggested in previous shows that having someone get your foot in the door is the best way, but I really think that feels gross to me. Anyways, long-time listener of your show and first-time caller. In fact, when I was in prison, a few years before I was released, we finally got tablets with an incredibly limited amount of content. Your show was one of a few on coding, but I really enjoy your take on the soft skills because even though I worked in a non-traditional environment, teamwork was always the focus, and I listened to everything from square one it took me a long time to get there so thank you for your podcast you don't know how many times i could sit in my cell listening to your show and disappear from my cage sincerely

names have been changed to protect the guilty oh man honestly i'm kind of having an emotional reaction to this one right now it really puts all of the oh my boss forgot that i asked him to do a thing like first world problems in a different perspective it totally does wow someone someone is too slow to review my pull requests very different from like i'm dealing with pressures you can't even imagine i'm sure that's so true wow i just i just have so much respect and i don't even know i don't know just a lot of positive feelings toward this person for the time they served and now trying to find their way in the world really challenging and i just i don't know why that that last sentence really got it kind of got me in the feels sitting in your cell listening

to your show yeah it kind of reminds you that not everyone's in the same position you are you know not yeah and not a not a thing we ever imagined i mean our last podcast was only for inmates and it it didn't succeed so we we pivoted to soft skills for software developers i think we accidentally made a podcast that got a bunch of people into prison yes i know probably that bad of advice that's what i was always worried about yeah doing doing crimes is bad but i don't know if you if you yeah if you serve your punishment you should be able to get a job you should also be able to not be miserable and tortured while you are doing i mean i'm a huge believer in redemption you know huge believer now i here's here's like the big challenge though this is going to be hard and

i've talked to people recently and actually oh geez it's really hard now it's always been hard to get your first job as a software developer and it's way harder today than it was like three years ago. And that's just because of the economy at the moment, right? A lot of companies are tightening the belt, cutting costs, and first-time developers are having a hard time. It's also hard because of AI. I say that because there's actually kind of a groundswell movement right now. Some very high-profile people are saying things like, we don't need junior developers anymore because AI can make senior developers fast enough and junior developers can't use AI effectively because they can't tell the good from the bad suggestions. I think that's kind of interesting thing to say.

So anyway, there's some darn big headwinds. And then there's always been the incarceration headwind where if you were formerly in prison or convicted of a serious crime, especially one where you served a lot of years like this one. Actually, I shouldn't even say that. Any crime, I think, on your record is a headwind. So I just wanted to say with all that long-winded blathering i just did that i'm sorry it's going to be a challenging road for you right now like and it's awesome that you have a few opportunities or like this one where you've actually got someone you know yeah and i mean i i would say relative to the average person who's who's served a long prison sentence you're probably in a much better position to get a fairly lucrative job imagine if

you didn't have a technical skill set that is still in relatively high demand. So I agree it's going to be hard. I think you have a shot, certainly. Can we talk about the comment that the question asker said about it feels gross to have someone on the inside? Yeah, like it feels gross. Yeah. Yeah. Not gross. What do you think? It's so good, actually, because you can learn so much about what the company is like. So there's a lot of benefit that way. And they actually can do a lot more vetting of you. And this is setting aside any backstory. So just putting everyone on equal footing on the same playing field, whether incarcerated in your past or not, whether you have experience or not. Having someone who knows you in the company gives the company better

visibility into who you are. So think of it as like an extreme interview. This person can vouch for you. They can describe how you work. They can talk about your values. They can talk about what they know about you. And it just gives the company a big leg up about you. Now, yeah, it is a bit of a competitive advantage over other applicants. I'll grant you that. But companies love reducing the risk of hires. And one way they do that is by having a reference who knows you well. Yeah, it's not like gaming the system at all, because the company is pumped if they have some kind of connection to the applicant, like you said, to reduce the risk. a random resume coming across versus a resume with the name of an employee that works there

already attached to it, you can get so much more information about how they might fit and what they're like to work with. So yeah, it's not like you have unfairly gamed the system. It's more like you're lucky to have this referral and the company is glad to have someone that can refer you. downer for the people who don't have any connections to any company because now that they're going to be at the you know they're not going to be a surface to the top like that yeah that's fair but i don't know yeah it's true there's nothing you can do about that you can't you can't like if if you withdraw yourself i recuse myself from this case your honor interest i cannot do this ethically yeah i know someone that works there already so it's not it's not

Yeah, exactly. And just to kind of put a fine point on the numbers that are literally that you're up against right now, and why I think you should take advantage of any opportunity you can get to have your name surface to the top of the list. I actually posted a job opening for my company last Friday. By the following Wednesday, Wednesday morning, I looked at the job posting, which I'd been checking on every day. By Wednesday morning, so we're talking, i posted it friday afternoon so you had you had just like an hour or two of so-called working hours on friday you had all day monday all day tuesday and then wednesday morning so like a little over maybe two and a half business days i had 400 applicants apply for that job

yes wild i've always heard stories like that about resumes and applications and never specifically about software engineering always just kind of to illustrate how hard it is to get a job and i would always shake my head at them and say oh boy am i lucky and yeah it comes for us all i guess so what what do you do i think in a way my mind goes to advice we've given about being fired before and kind of having a having a story to tell not a not a lie but like you need to be able to They're going to ask if you got fired from a previous job, hey, why did you get fired? What happened?

This is like a more extreme version of that. They're probably going to ask what happened. And I don't know that you need to go into exhaustive detail, but I assume it's a matter of public record. I'm sure they can Google your name somehow. Or even pay for a background check, which they probably will. Most companies do. Yeah, so there's some stuff I omitted that said they were open about their background

to get the job they have right now. So I edited that out of the question, but I don't think they're implying like I would hide it, but you should be ready to talk about it in the interview because it will come up. I was trying to think of how I would expect a candidate to respond to me in that kind of a situation. And I think one thing that I would really appreciate

is for people to be really open and forward about it. Like stating out loud, yeah, there's an elephant in the room here. I have served time for a crime. I want you to know that that is totally in my past. And if you have any questions about it, I'm willing to answer them. Like that's an answer that I would hear and it would help a lot, I think, to put me at ease. Yeah.

Yeah, because there's going to be this little thought in the back of their heads of what if they do something? Like they have shown they've done something in the past. What if they do something now? and in addition to all the other just i don't know it's a competitive market out there stuff so i think you can you mentioned it in the question right you've worked under pressures that that we cannot imagine which is definitely true i think you can in a non-cheesy way bring that up as as something you have learned from your experience not like uh i mean there's there's deadline pressure there's interpersonal conflicts at work there's there's unrealistic demands like

there's there's pressure it's definitely not high stakes at all but if if you can um demonstrate how you have learned how to handle that pressure and can be responsible and and kind of cool and and effective despite normal business pressures i think that i kind of have a different opinion on that one. I don't think that I would appreciate at the level that I should if someone said I've dealt with extreme pressure. Because I start to think like, yeah, you're probably talking life or death, bodily injury kind of pressure. And when I say pressure, I just mean like a customer's pissed and we have a deadline we have to get to. And it's almost like make-believe pressure in the corporate world. Yeah, exactly. It's like, this is nothing like what you dealt with.

and yeah it's actually honestly it's like corporate pressure is like baby land compared to this like i think probably there's something similar to be said for people who served active duty in the military it's like i've been shot at i'm like okay that's a lot of pressure you know like that's a lot of pressure yeah can you i get it that you can handle that can you handle this baby pressure that we have here you know it's like a totally different thing you're saying it's it's like more annoying it's not like yeah you're like fight or flight response is not, or I don't know, whatever tools you learn to deal with that pressure might not be useful if like someone is bothering you in a meeting. Exactly. And I think 90% of the population

has basically zero exposure to what life is like serving in a truly high pressure situation where lives are on the line or bodily harm is on the line. And so I think I would probably just not bring that up. Like I would not try to twist this. Well, twist is not the right word. I would probably as an interviewer i would probably not appreciate someone saying like trying to use their experience in prison as a way to position them as a good candidate for the job and that's not to say that the things they learn aren't valuable there it's just that i think it's something that me and in my ignorance just could not really i couldn't really turn that into like okay great you've checked the box for me it wouldn't exactly it wouldn't relate and i'm sure that i'm sure that

this question feels that way. And I'm sure a lot of people who have served in active duty, like in combat zones would feel, would kind of feel that way too. Like, look, I could tell you I've served under pressure, but you, you have no idea what it's like. And I'd be like, yeah, I don't like you're, you've probably done some amazing things. Okay. Well, you get to choose who to believe. Exactly. Flip a coin. Yeah. I do think it would be much better to demonstrate the amazing amount of skill. I mean, you have had an 18-year computer science university program where I'm guessing that you were given a lot of time to study and practice. And let's focus on that. I mean, I've hired people who had no professional experience whatsoever, but who

had spent their entire childhood with a significant time allocation in programming. In fact, I hired someone who at age 17 had been homeschooled and had never set foot in a public school building, but who had been to the library a lot and had checked out like every book they had on different programming languages had read them all and had an impressive portfolio of all these cool personal projects that they had created and i hired that person enthusiastically because they had i don't know how many thousands of hours of study under their belt and sure enough they were great they totally knew their stuff and delivered a lot of value on our team we're just as much of a contributing member as anyone else but it wasn't because of any of the kind of like i'll call them

out-of-band experiences that person had. It was the straight-down-the-center-of-the-fairway programming experience that they collected through self-study and development. I would focus on that. Huh. Yeah. I think that makes sense. And I mean, for many reasons, you're in an interesting spot. I guess it's dumb to say that out loud. But... I didn't think it was dumb. Someone with almost two decades of programming experience is going to be typically in line for very senior roles if you're applying somewhere or being being interviewed somewhere but you also have this this the prison thing kind of weighing on the other side so it i mean you you have a different balance of technical to soft skills uh experience than than the typical candidate

you might be i mean maybe that means you'll be in more junior roles maybe this is more junior role than someone with 18 years of experience. I think I agree that you should demonstrate your skills. I think you should also spend some time. They're going to try and figure out how will this person work with the team on projects, especially if you mention, as I think you should, that's not a thing you did very much in prison.

You were mostly by yourself. And you could be like somebody with one really buff arm and one really weak arm. You know, you're like, like you've got this heavily exercised muscle of just cranking stuff out and then this weaker muscle of working with the team on stuff. I think you need to be able to demonstrate you will be effective and learn well how to do that. I don't know that they need to, that they would expect you to just be an expert on working with the team already, but you need to at least show like you don't have, I don't know, bad habits or going to be, have an ego or be hard to work with. And who knows what preconceived notions they're going to bring to that interview table. Yeah, I do. I just choose not to tell you. Good luck with that one. Yeah.

Oh, man. Yeah, this is a tricky situation. It's complicated, and it's unfortunate that it's complicated, but it is because human beings carry a lot of biases about this kind of situation. I would suggest a few concrete things, and then I'll be done answering this one for me. But I would say get your resume in order. And your resume, of course, is not going to have a lot of lists of company names on it. Instead, it's going to have a list of personal projects or other side projects that you've worked on. I get the impression from the question that you've got a lot of cool projects, maybe not open source because, you know, internet connectivity is limited when you're in prison.

But I get the impression you've done a lot of coding. And so I would find a way to show that on your resume. And I've seen some great resumes that look just like this from people with very little experience, especially if you have links to things that they can click on and go experience themselves. And that's how I'd flesh out your resume. So, the resume is number one. Number two is you got to prepare answers to questions about what you've been doing and why you're in prison and what, you know, how can you expect me to behave now that I'm out of prison? And it would probably be very good to pair with someone in a practice session so you can get some experience answering that question succinctly and convincingly. But the last thing you want to do is

stumble through that one and not have a prepared answer for it. And then the third thing is do not be afraid to take advantage of personal connections you have with companies. That is your absolute best path. And frankly, maybe your only path for getting into a company as a software developer right now. It might take a personal connection of someone to vouch for you in order to overcome the friction that comes with having some crime on your record. And so with that little bit of help, I think you can definitely overcome these headwinds. And I am super excited to see where you end up. And I would love to hear later how this all worked out.

Yeah. Thank you for writing in. I'm glad that we could help somehow, although it bothers my mind how. Yeah. But I'm glad we could at least distract you. Yeah, it's great. And I hope it goes well.

Honestly, it's really cool. It was a great honor. Jameson, we've been talking about WorkOS a lot, and they have added some very useful stuff to their product. Now, WorkOS is not just for adding SSO to your app. It's so much more. They've launched some cool stuff, and we will tell you about it. WorkOS lets you not reinvent permissioning with their new fine-grained authorization

system, which is based on a Google system white paper thing called Zanzibar. Very fun word to say. I've actually built some fine-grained auth systems myself, and they had a way more boring name. And also, I had to maintain all the code myself. Yes. Also, check out WorkOS's radar feature, which can block bad signups from your app. So things like bots, fraud, and impossible travel, like someone using a VPN or proxy

to trick your signup system, they can detect all of that for you and help you avoid fraudulent signups. They launched an entitlements feature that integrates with Stripe so your app can automatically give access to accounts that have paid for new features. I've also built one of these myself, and it can be a huge pain in the butt. So nice to put that on someone else. Yes, totally. To me, the coolest feature they launched is a B2B app starter kit for Next.js.

WorkOS will actually help get your Next.js app essentially from zero to one super fast. They provide authentication, billing, user management, audit logs, and a ton more. And I got to say, if there's an easier way to start a B2B SaaS app than WorkOS, I can't think of it. Do not forget the Passkey support. It's effortless for you to add Passkey support

and your users will love it. Check out WorkOS.com and try out all these amazing new features. Okay, should I read our next question? I was hoping you would. this is from an anonymous listener second time caller from nyc i previously wrote in as an 18 year old cs graduate in episode 332 as a lot of episodes ago man we've done this a lot i've focused intensely on work for the past four years consistently working 60 plus hours per week

i always assumed that this approach in life would eventually bear fruit but a couple months into turning 20 i'm realizing that i haven't really done anything memorable besides work which is a scary realization at 20. I like working hard and want to ensure the success of the company I work for. I also want to feel like I am living. How have you struck the balance between work and non-work in your lives? And how has that related to the culture of the company you were working for at the time? I should also mention the company I work for, early stage well-funded, does have a culture where it's expected to work every day and 60 hours is approximately the minimum expected. Okay. Every day. I'm thinking that must mean, do you think that means seven

days a week? Oh man, I don't know. I mean, 60, if you worked seven days a week, about eight to nine hours a day, that would easily get you to 60. Yeah. And it'd be a lot of hours in a day if you were working five hours a day. Yeah, at least 12, you know, plus breaks and lunchtime. So you're looking at like 13 if it was just five. Huh? Well, either way that sucks. Yeah, exactly. It's not like one is better than the other. Why am I splitting that here? Yeah. Yeah. What an interesting question i feel like for anyone who works a lot of hours and either likes or gets sucked into work this is this is this comes at some point so it's a scary realization at 20 it would be a much scarier realization at like 35 so i think it's good better now than later you know yes definitely

now in fact that was one thing that struck me from this question is oh you're only 20 they're kind of speed running life right 18 year old cs graduate 20 years old and grinding at their job for four years like you're yeah i mean i at age 20 i was not even professionally working yet i didn't even graduate till 20 yeah four i think yeah i never did that's right jameson's still there's still time jameson what's the opposite of speed running call it tortoising just taking my time consistent and faithful well although i'm not either i'm doing none neither of those consistent or faithfully working on graduating so i seem to recall it's probably been a few years now but i seem to recall during this show it came out that you hadn't finished your cs degree

yep you i think at that point you re-enrolled in some classes whatever came yeah i've done that a couple times i mean the same thing that happened all the times i did it i just then did not i've had one i'd say one solid attempt where i think i got about a third of the way through the the math class that's the big okay okay that's good and then i just didn't do it anymore i don't know and then do you have to start over from scratch if too much time goes by on that math class i mean i would have to because i have forgotten all of it oh yeah yeah so i don't know what the requirements would be but it would probably be better for me to do that instead of try to jump into like a midterm right right okay well sorry to sorry to bring up that old wound

Oh, no, it's fine. It has no power over me. It's not. Okay. Clearly. It's fine. Yeah. So, I mean, I looked at this and I thought age 20. Age 20 is very early to be having some kind of like midlife crisis where you think, oh, no, I'm working too much and I don't have anything memorable. I probably didn't lift my head up out of the water and start thinking about those questions until I was like 40. Yeah. You do have a lot of freedom to do something quite different about it where yeah if it happens later sometimes you have a family maybe you have

kids you have probably a mortgage or i don't know it's hard to like drop everything and go to thailand or whatever yeah journey you go on if you have more more things demanding your your time and attention i honestly i gotta say i think those kind of things where you say i'm i'm like i'm just gonna put myself in this question asker shoes i'm 20 years old i'm working 60 hours a week i just woke up it's been four years and i haven't done anything memorable i think the idea of like jumping on a plane and traveling to some exotic location is super overrated why well i just think what are you going to do you're going to go you're going to have some some pleasurable moments you're going to eat some interesting foods you're going to drink some exotic drinks you're going to

experience a new culture briefly for a period of time i'm going to assume you go alone okay yeah and and then you come back and it's like you have this develop a sustainable romance you live across the world right and and then you come back and it's like you've got this photo album full of selfies of you eating foods in a different place and it's like hmm that's just not where for me that's not where the meaning of life comes from like to me meaningfulness which i believe is right at the heart of this question comes from experiencing life with someone else who i put as a priority the bond and kinship that forms when you do things together for me and i think for many people is like this actually brings the meaning to your life instead of just the raw

experiences themselves huh i mean part of the problem is you it's hard to find that person if you're working five days a week 13 hours or seven days a week eight to ten hours yeah for sure i don't see a way if if 60 hours is the minimum expected and you're expected to come into work every day i don't see a way to do this without quitting your job but i assume this is like a prestigious i don't know it's a well-funded early stage company maybe it's in ai or some other whatever field is hot whenever you're listening to this yeah like there's a reason that you're grinding so hard at work and then why that's the norm at the company and you're clearly quite bright if you graduated from college at 18 years of age my point in saying all this is

you seem to be kind of attracted to achieving a lot i assume this approach would bear fruit so you're kind of like investing in if i work really hard at this hard thing i will get something out of it maybe that's i don't know maybe you want to be rich maybe you want to be a founder maybe you want to be famous like or just be able to say look at all this stuff i did but that is somewhat at odds with um doing a lot of things that aren't working and yeah so if i say quit your job and then you go get another job at a different highly demanding now you pivot to fintech and i don't know yeah make a ton of money and hang out with all the finance people and still don't find meaning that feels like a failure mode here definitely definitely and and not only a failure mode but

a likely outcome yeah but i i do think one thing to be said for the fly across the country approach is it is a reset and that's not the only way to reset but you have to carve out some space somehow and and being physically on the other side of the world and is a hard constraint that you cannot undo and accidentally like get sucked back into i'm assuming you can't work 60 hours a week at this job if you are like uh on a on a backpacking trip across europe or whatever kind of cliche like yeah find yourself thing yes that you choose to do but but you could do something else too i i do think you gotta take a break yeah but i mean i'm not really i think take a break yeah like if you were feeling like you're gonna get burned out and not able to continue working

hard i think taking a break would be great but it's like if you're looking for real life meaning like there's no number of breaks I think that will give you that as long as your day-to-day is still this I guess that's part of why I'm saying quitting your job feels like a requirement for this yes the break doesn't feel like a go on vacation break it feels like a reset things to evaluate what you actually want type of break which is very hard to do when you're so heads down all in on this job well I have a good friend who I may have mentioned in the past but he worked at a company that after some number of years did like a six-week sabbatical kind of thing where you could take paid time, six weeks off, and do whatever you wanted during that time.

And he did this, I think, twice in his time there because he had been there long enough to do it twice. And each time when he did it, it completely changed his priorities so that when he came back, he felt like a totally different person and reorganized his life to now accommodate these new priorities that occurred to him. But like you said, Jameson, when you're in the day-to-day grind, these things just don't pop into your head. You know, it's like you need some time to clear your mind. Yeah. I'm reading the notes you wrote and they're good. I want you to say them. I don't know how to smoothly pass it off to you though. Yes. Jameson's seeing my notes. Yeah. So I did want to ask, how did this person get this idea that if they would just go really fast and focus

a lot on work that they would get this amazing outcome. And I guess I don't totally know exactly what fruit this person expected to get, but it feels like the world is full of books written as cautionary tales to avoid exactly this mentality, like Charles Dickens' Christmas Carol. I mean, it's like Ebenezer Scrooge is this person's story in the limit. Yeah. It's a Wonderful Life. Doesn't it have something kind of like this? No, I think that's kind of the opposite of this. It's like somebody who thinks he doesn't do much, but actually he's formed all these wonderful connections and just didn't appreciate it.

All right, that's the one that I need to watch then. Yes, exactly. You probably are like that, I'm guessing. You've probably done so much good for so many people and you just don't really have a good inventory of it all. All right, I'll go check it out. All you have to do is pretend to jump off a bridge and an angel will guide you the rest of the way.

In the snow, in winter. Yes, eaten by an alligator on your way to school. That's not a genre that exists because that's not a thing that happens. Right. Right. I think it's probably commonly talked about because it's easy to fall into. I think so. And I think that's exactly what's happening here. It just has all the trappings of it. And I mean, look, I'm someone who works hard and I'm super invested in my work and I get a lot

of fulfillment from my work and I spend a lot of hours on my work, but it is by far not the only priority in my life. At this point, if I was sitting down across the table from someone individually, I would give very tailored specific advice. But since we're speaking to an audience of roughly seven or eight people, I can't possibly know all the different viewpoints here. But I've chosen belonging as a priority. And I belong in several different vectors, family being one of them. I have children. And this just completely rewires everything in your life, the way you think, your priorities. And it has caused me to have a default state where other people are actually more important than me in most of the choices that I make. And some people might think,

oh, wow, that must be terrible. You must always be last place. And actually, no, it's wonderful. It's actually the most amazing thing ever. Because when you sacrifice like that for people who are not psychopaths, just to caveat there, they give back as well. And you both end up benefiting. It's not a zero-sum game. It's actually the pie grows when you engage in deeply committed relationships like that. So for me, that's been the thing. And I think when I look at this, I think, well, you're only 20 years old. So I'm not expecting you to have a bunch of children right now. This is probably not the right time in your life. But I also think, who cares? Keep focusing on work. It's not that big of a deal. But you better set yourself up

for a trajectory to where in 10 years, you're not doing the same exact thing and just working 60 hours a week and expecting that to bear some kind of life meaningful fruit because it's not going to happen. I think there's another way you could look at this is opportunity cost. So if you earn a bunch of money very young, that compounds into a bunch more money when you're still pretty young. but also there's a bunch of other stuff you can't do if you're purely focused on earning a bunch of quite young and working really hard your your health right i am i am at the age where i get to use the words at the age and tell physical differences in my body got hair and even weirder places stuff like that you know but like i i don't know there's there's stuff i physically

could not enjoy as much as i could if i were 20 if i got really into ping pong i would be I would never be as good at it as if I got into it when I was 20. That's a good point. There's a type of social gathering that happens when you're in your 20s that does not happen if you're in your 30s. Like when you say type of gathering, like the impromptu, super fun. Yeah. 30-somethings and 40-somethings are just a bunch of boring losers.

Is that what I'm hearing? Because that's what I feel like. I don't think we're boring losers. Actually, I think I'm a boring loser. I don't think you are a boring loser. but just inherent in being older is more more commitments and more responsibility and harder to be spontaneous and and more attached to lots of things in lots of different ways which changes how it feels to get together so if you just grind really hard in your 20s and then say all right i'm

in my 30s i've made it now it's time to really like get out and and develop interests and hobbies and meet people. You can still do that, certainly, but it will be different than if you had done that in your 20s. There will be ways of interacting that will not happen in your 30s and 40s. That's fair. And the pool of people who are available for interaction will have shrunk. Yeah. Yeah. I don't know. I guess so. Because of the responsibility thing you were just describing. I mean, they just aren't there. They're not just hanging out on the couch in the common area anymore. They're off dealing with their responsibilities. Yeah. You know, a higher percentage of them are,

is my point. Okay. Yeah, that makes sense. I think I get what you're saying. So I could see this backfiring and just making you incredibly stressed out about like, well, I have to choose this thing or that thing. And that's not necessarily my intention, but my intention is more to point out that you can get things right now that you, it's a unique opportunity, I guess, right now to to go develop hobbies or meet people or do interesting non-work things and for better for worse you can always find a job to throw yourself into there's always something work related no matter the age that you can get really into and dedicated to and grind on yes i don't know the corporate world will always welcome you yeah well and even the startup world

uh yeah you just get to be the grizzled veteran with lots of life wisdom that's kind of fun gotta go develop the wisdom i think another way to say what you're saying jameson is that there's a window that is open to a bunch of things that you can only do at a young age and that window is gradually closing every year it moves a little closer a little bit more closed and eventually it will close or be so close that it's hard to fit through and i think you should take advantage of that time when the window is wide open, which at age 20, it is. And you should go do all those crazy things that you just can't do when you're 35, 45, 55 years old. And just have a great freaking time. Make a ton of friends. Like the friends that I made in my early 20s are probably

some of my most treasured friendships. And those kinds of friendships, they just, the rate at which those friendships materialize anew in my world, like to where I meet new people and they become deep lifelong friends. It was the highest in my early 20s. And it has gradually decreased down to much closer to zero per year than it was when I was 20, 21, 22. So take advantage of that time because that window will not be open again. This gets into just platitudes and generic stuff, but I feel like... How old am I? Am I 37? I think I'm 37. There's probably a 57-year-old Jameson who could give 37-year-old Jameson the same exact advice, right? Like, oh, there's all this stuff I can't do now that I'm 57 that you should have been doing. Maybe I'll go off and

have a think about this. But this is, I mean, this is a great question and it's kind of evergreen. I feel like you can always, no matter your state in life or how heads down or up you are, you can always be introspective about what kind of experiences you want. And it's probably pretty rare that someone would take some time to say, am I getting what I want out of life and come away with, yep, completely. Nothing should change. Yeah, that is pretty rare. Well, have we answered this question? It turned out it was a much bigger question than I thought. Yeah. I mean, I don't know. I answered it enough. I think quit your job is pretty good advice, honestly. Like step one of this question. I think so too. Quit your job and be a 20 year old. Yeah. Hard to be deeply

introspective working seven days a week. Yeah. Well, what can people do if they want their own questions answered, Dave? Go to softskills.audio and click the ask a question button where you can fill out our form. Thank you so much to everyone who does that. We love your questions. We do. We love them. We love you. We'll catch you next week.