Ep 85: The Three-Week Funnel That Keeps a Job Search Moving
Watch the YouTube video version above or listen to the podcast below!
Episode Summary
Alex and Dave spend this episode on two questions that turn out to be the same question: how do you decide what is worth building, and how do you decide what is worth doing next. Alex opens with a side project he started after wondering, while driving around his city, which small business a given town could actually support. He built a statistical model on free data: the U.S. Census API, which he says takes about three minutes to start pulling from, Overture business data that traces back to Foursquare, and a federal dataset identifying underserved healthcare areas, which he added to sort out how many dentists and oral surgeons a region can carry. The work runs in Python inside a free Google Colab notebook. He warns off one shortcut directly: scraping Google Maps produces wonky data and is not a good plan.
The finding underneath the project is the transferable part. Many businesses are population-dependent and hit statistical significance quickly, and there is a rough ratio of people to gas stations, people to daycare facilities, and people to hair salons. Those ratios do not adjust in real time. When a town grows, the businesses have not opened yet. When a town declines, they have not closed yet. That lag is where an opportunity sits. Dave connects it to lived experience, describing friends in an aspirational Minnesota town who complain their kids have nobody to play with, when the demographic data would have told them in advance that only people who have already made it can afford to live there. Alex extends the same point to free satellite data, which can be downloaded straight from geostationary satellites, and to a catalog of transcribed hieroglyphics nobody has ever made searchable. The data exists. Collecting it, organizing it, and making it useful is the step almost nobody takes.
The middle of the episode turns to the mess that follows all this capability. Both hosts describe the same problem: piles of Claude documents, NotebookLM files, and outputs from past projects, with no good answer for whether to de-duplicate them or burn everything and restart from the three that matter. Alex, drawing on Anthropic's training course, recommends setting global instructions so the AI always knows your role and adjusts its output accordingly, and revisiting them whenever that role changes. He is blunter about prioritization. Asked for the last two weeks of to-do items, the tool returns a laundry list of which maybe 10% will realistically get done, and the useful counter-question is what actually breaks if you skip the task. Three weekends of driveway repair to buy one extra year is not worth it in his head. Dave runs the opposite approach, a free Asana project built for 2026 with quarterly milestones, the every-other-Tuesday podcast cadence, basketball coaching season, and family obligations loaded in as constraints, so the system asks how many hours a week he can honestly commit before anything gets added. He checks progress mid-year against both task completion and channel analytics, which still means downloading spreadsheets by hand because none of the tools talk to each other. Both hosts note their own seasonality: Dave is creative in fall and winter and execution-focused in spring and summer, and he does not fight it.
The second half addresses layoffs, prompted by Dave's observation about companies that fire people right before Christmas. Alex shares the framework he built after his own layoff and later ran with roughly 14 or 15 people over a year, while flagging honestly that it is three to four years old and predates AI entirely. His first point is emotional rather than tactical: a layoff is a breakup, it feels personal even when it is impersonal, and every work relationship ends at once without your consent. From there the system kicks in. Define your requirements before you need them, starting with a salary floor, so negotiation is not a surprise. Apply only to your ideal tier for the first three weeks, then add the next tier down, which gets you the best realistic outcome without drowning in irrelevant applications. Treat the pipeline as a four-week funnel where a cohort of applications is dead by week four, which means you have to keep filling it rather than waiting on the one great job. Take two days a week off from searching entirely, what he calls HR catch-up days, because endless LinkedIn scrolling is painful and ineffective, while staying ready to answer any interview request immediately.
Dave adds the layer the framework predates. Know your first five phone calls before you need them, specifically people who own businesses and might hand you freelance or ghostwriting work. Use AI to run mock interviews for the role you are targeting. Or skip typing entirely: use voice capture and a transcript tool to talk for 20 minutes to an hour about your career, then turn that raw material into case studies for interviews and your website, and into a clear read on how you should position yourself. Alex adds that the same approach surfaces job titles you did not know to search for, and rules out ones you would hate within six months. Both push back on resume avoidance, since a tool that interviews you rather than guessing from your job title produces something accurate instead of AI slop. Dave closes with the least technical advice in the episode: get a tub of ice cream, call your friends, take the day, feel the feels, and hit it hard tomorrow.
Ep 85: The Three-Week Funnel That Keeps a Job Search Moving Podcast and Video Transcript
Dave Dougherty: [00:00:00] Hello, and welcome to the latest episode of Enterprising Minds. Alex and Dave present for the session. Um, Alex, for you, I'm gonna kick it immediately over to you because you have the best idea for what we should talk about.
Alex Pokorny: the second topic I think, if anybody's doing job searching, they're concerned about AI, what's the next steps, layoffs are happening, we'll get to that as our next topic.
So a little teaser. Yes, sir. That one is coming from Dave. Super. Um, yeah, please do.
AI Side Project for Local Business Ideas
Alex Pokorny: Uh, the first topic that we're gonna hit is just a random ... Yet again, I got another random side project because I just, I love them. That's
Dave Dougherty: how your brain works. It's good. Yeah.
Alex Pokorny: Yeah. It, is. And AI just enables it. It's such an enabler to start these weird random things.
Which was [00:01:00] an idea that I had just driving through the city that I live in a while ago, and then this last week, I ... it came up again, and I was like, "Oh yeah, I should totally do this." And this is the idea, is if you're looking for a small business, local small business to start, which one should you do, and where should it go?
Uh, what city should it be in? is your city oversaturated with gas stations? I don't know. Is ... You know, maybe there's one town, three towns over that is, underserved and you know you could probably make profit on day one just by existing there. Or, you know, what ... How many dentists are needed in a particular city, or plumbers and, plumbing supply to those plumbers?
Like, all of these things have some kind of demographic aspect to them, and I love demographic data. I mean, that's that's my jam, right? Tons of data nerd, right? [00:02:00] And all that kind of stuff. But also, being able to provide a tool- If this thing works out, being able to provide a tool to individuals who are trying to be entrepreneurial like I have in the past, I mean, absolutely, community that I care about too.
So it's been a really fun project, and it is very easy to be AI heavy with something like this because it's a statistical model, tons of Python, APIs to data. I mean, all that kind of crazy stuff that's going on, and just constant testing, trying to make something that actually seems statistically significant versus just, it seems like this region doesn't seem to have any based on Google Maps, which, I mean, unless you pull apparently also Google Maps data, it's pretty wonky data actually that you get from the Google Maps website, so scraping that is not a great plan, by the way.
Um, one-- Just a couple of cool things about it that I thought would be more widely useful to people, is one, there's a ton of data sources out there, and asking [00:03:00] AI about what other data sources may exist that would be helpful is a great idea if you work on a project like that. for instance, there's one that I found that was u-they're the underserved healthcare areas, which helped because I was trying to figure out how many dentists are in a particular area, and orthodontists and orthosurgeons and all these other kind of specialties as well.
And that added data set on top of these other ones was helpful. Uh, US has census data, which is free. An API, literally within three minutes, you can start pulling data from the US Census, which is awesome. So there's tons of data that's out there that's free. but there's also-- there was one like called Overture, which pul-pulls even from like Foursquare, which became a, a data warehouse kind of company But it pulls from them, so that was really helpful to get down to, like, minutiae data too of, like, literally how many individual businesses, hair salons exist in this one town, versus census, which is a little bit more generic.
Um, you do run into a lot of problems with this kind [00:04:00] of stuff with, like, how you define regions and areas and radius and all the rest of this kind of stuff. But in short, there are a lot of company or a lot of business, businesses that are really population-dependent, and that are statistically significant, like significance that hit that very, very quickly.
and depending on the size and whether or not your particular town is growing, stable or declining, the businesses that exist there will lag by quite a bit. So even though there might be a lot of growth, they're probably ... They haven't opened yet.
Dave Dougherty: Right.
Alex Pokorny: Or even if it's declining, they haven't declined yet in the same, like, correct ratio basically, which there is kind of basically a ratio of how many people to gas stations you need and how many people to daycare facilities and childcare facilities you need, and hair salons and everything else.
so if you're interested in that kind of crazy stuff or if you've had ever been wondering, [00:05:00] "You know, I'd love to open a," whatever, a restaurant or you go to the gas station, you wonder, like, what's it take to run one of those or a franchise, some random franchise, or you heard of somebody who's doing one and you've been wondering that.
I absolutely just, just endorse it. Play around with AI for a little while. It will help you run, Google Colab, which is free. It'll come up with the code, which is ... I mean, you're saving 20 bucks a month anyways. And you might be able to nail down that idea a little bit further down the line of saying, like, "Oh, is this realistic?"
Well, maybe it is.
Dave Dougherty: Hm.
Alex Pokorny: So sorry, long tirade on that, but it, it, it's been fascinating the last couple of days. I've been spending way too much time on it, so it's been a lot of fun.
Dave Dougherty: No, but it is interesting 'cause it does hit on something that I would say is one of your core strengths, which is pulling data from all of these other places.
Yeah. and it is interesting to, you know, lived experiences, right? talking to some [00:06:00] friends that we met, they live in one of the towns that, you know, in Minnesota where it's an aspirational town, right? Sure. Um, but then they're sitting there and they're complaining that their kids don't have anybody to play with.
It's like, yeah, 'cause the only people that can afford your town are people who've already made it.
that's- I kind of hear that ... that's why you go tour neighborhoods, you know? Yeah ... y- the neighborhood we're in is great because there are a bunch of kids who are in the same age range, and they're like close enough to be willing to hang out with one another.
Mm-hmm. Which is a great, you know, that was the thing that I really wanted for my kid, and so the fact that that actually happened, is great. It makes it hard, harder to move, at least while he's still young. But, those sorts of anecdotal [00:07:00] ones, like, man, I wish there were more, people our age or whatever.
yeah, here's the data. You know- Good ... you could have pulled it. And this actually- Yeah ... brings up another, another thing I was thinking of Um, there's always that thing of, "Well, I coulda done that." Right? Like, how many people say that about the arts or- Sure ... you know, basketball players- Sure ... or whatever else.
It's like, "Yeah, I could do that." Well, you didn't, right?
Alex Pokorny: You stuck with it for the last 12 years. Yeah, maybe, but you
Dave Dougherty: clearly
Alex Pokorny: didn't. Yeah.
Dave Dougherty: But it's also, I mean, it's a similar kind of thing with marketing, with whatever else. Like, you can add those specific layers on top of what you already know or the things that you already know to gather-
Alex Pokorny: Yep
Dave Dougherty: by seeking out the free, amazing data sets that, are available to us. So-
Alex Pokorny: Yep ...
Dave Dougherty: yeah, shout-out [00:08:00] on free resources. Yeah.
Free Data Sources and DIY Apps
Alex Pokorny: Also found out this week that there's a number of satellites out there that you can download their data for free, literally directly from the satellite. Didn't know that was a thing.
Totally is a thing. You have to- It
Dave Dougherty: seems like a spy novel thing.
Alex Pokorny: Yeah, I know, doesn't it? Yeah. Yeah. There's geostationary satellites, so they stay in a consistent location, so you can literally download, if you want weather data, like literally the visuals of storms that are going on, straight from a satellite straight to your computer without any kind of Wi-Fi connection or anything else, 'cause the data's literally just being beamed out constantly.
there's just... It's funny how much stuff is out there and is available, but it's also, like, collecting it, organizing it- Yeah ... making it useful, and whether or not it is useful to you is really the step that I think it seems like so much information is... Especially, I think, as, you know, we've gone through time.
Information was locked in books [00:09:00] at a library- Right ... or locked in a reference center or only at one place, one college, one time, one person's head, one whatever, and it's hard to access that. That really has changed.
And it's hard to sometimes, with a mental model, keep up with that idea that, oh yeah, you could totally do that now.
you're interested in opening a second location or your, you know, your spouse or friend is looking for a new job or something, you could. Like myself, make an agent that every week pulls new CMOs and, you know, job openings for my particular career set, and automatically updates a spreadsheet always, which I always have on hand at any time so I can know what companies are growing and which ones aren't in my field.
I don't ... I did that once. I s- I set it up, and I mean, I see it come up every week when it runs, but that's it. Like-
Dave Dougherty: Right ...
Alex Pokorny: [00:10:00] if you know, like, what companies out there are growing, how, well, how are you gonna do that? How are you gonna approach that? and these days you can approach it really differently than you could five years ago, and way differently than you could 20 or 15 years ago.
No more newspaper, no more locked away data, no more really expensive data set you can't ever get access to, or you have to pay for some, some, some subscription to a local newspaper. I don't have any of that kind of stuff, but I still have all that data at my fingertips with the same- Right ... 20 bucks a month.
Dave Dougherty: Well, and I think there's an interesting point, too, of the people who are good at collecting the data aren't necessarily the people who are good at communicating the fact that it exists, right? So that's- Oh, yeah ... really that opportunity, you know? It's like, okay, cool. Yeah. Like, you guys have done the hard work of getting all of this stuff, to your point, packaging it, shipping it out in a useful form, and you know, going through some of the pain to make it a useful thing.
Like-
Alex Pokorny: [00:11:00] That's a- Yeah. Yeah, that's the thing is it's raw, data and raw numbers and all the rest aren't really useful. Actually, there was a side project I haven't hit on yet, but I should ... I'm really tempted to kick it off, is I was looking at hieroglyphics and like, you know, can you use optical character recognition from, Claude?
Can I take a screenshot of something- Of course ... and can Claude figure it out, right? As one does.
Dave Dougherty: Of course. Yeah. Yeah. You know- Just to see if I could get bored ... just a passing thought while I was brushing my teeth. Yeah. Just You
Alex Pokorny: know, it'd be cool. It'd be cool if it worked. The short answer is not really.
what it could do is basically is there's a lot of databases out there that are either paid and are expensive- Mm-hmm ... hard to use, outdated, limited, and access is, you know, limited to only certain individuals from certain, you know, colleges or something out there. there's a lot of data that's out there basically that already is a lot of hieroglyph- glyphics that have been transcribed, but [00:12:00] nobody made a searchable database of them.
There's catalogs of them. You have to open up, uh, each individual file, and you can figure out somebody's transcription of that. But no one's ever pulled it all together and made it searchable or did character recognition across all of it, trying to say like, "Here's similarities that human eye hasn't picked up on yet."
There's all these systems and, you know, sets out there that are just a pain to use, and they're outdated as all heck. And the thing is, that doesn't have to be anymore. Like another random example, I got really frustrated with this like, uh, rain sounds app on my phone. It was just ads kept popping up, and it would stop working and all this other kind of junk, and I was like so tired of it.
I was like, "Claude, can you make me a rain sounds app that is offline and just plays and has like a timer on it or something?" Like pretty simple. give me like, I don't know, made up a bunch of random ones. [00:13:00] White noise, thunderstorm, whatever.
It's like sure, so built the app, and then I could download it to my phone, and now I've got a rain sounds thing that has no ads on it, which thank God.
The other one was so frustrating as heck to use.
And it was finicky, and it was ... This one is free, and it's on my phone, and it works great, and all I had to do was ask. Like that, that's such a different world than a few years ago where it'd be like, "Well, this one sucks. I'm gonna delete it and have to find another one and then hope, and maybe, ... maybe this doesn't exist."
Do I care enough
Dave Dougherty: to try to find another one?
Alex Pokorny: Yeah, which the answer was no, definitely for a long time until I finally realized. I was like, you know, the answer also could just be I just get my own.
Dave Dougherty: Yeah.
AI Productivity Systems and Prioritization
Dave Dougherty: Although- It's weird ... you do run into an, a thing that we've talked about in a previous episode of remembering all of the outputs that you have done.
Alex Pokorny: Yeah.
Dave Dougherty: And I know I'm coming up with that on a project right now where [00:14:00] there was very, uh, there was a clear delineation of a pre-event and post-event, and all the pre stuff is good, but I need to just like chunk it down into a single sort of, you know, analysis or like here's what we learned in the first half and then, you know, move on to these other ones.
But you have all of these, Claude documents or NotebookLMs or whatever else that's just there, and you're just like, "Ah, do I take the time to have Cowork run through all of this stuff to just like, you know-
Alex Pokorny: Yeah ...
Dave Dougherty: de-dupe it and start me off with like here's your three documents to start from, or do I pick the ones that jump out to me, burn everything else and then, restart from the three that I find, the most useful?
have you seen this? Because you do so mu- so many random things. I've [00:15:00] been debating recently on whether or not I should, save the useful stuff and just clear the memory of the AIs, you know, and, and kinda start fresh, with- Yeah ... the docs that I find useful and the prompts that I find useful.
Alex Pokorny: I, I recently was going through Anthropic's, uh, Skilljar training.
Dave Dougherty: Yeah.
Alex Pokorny: Um, which picked up a couple interesting things, and one of them gets to the point, and doesn't matter which one you use, ChatGPT or whatever. Uh, global instructions.
And a set of global instructions exist for any of them, which basically is you saying that I am X, I work here.
I've... You know, or at this type of company. You don't have to use your real name or real company's name, but you can if you want to. Uh, I'm in this kind of a role, which is helpful because then it has some context to basically always refer off of. And let's say you're a business analyst. Well, it'll always try to give you [00:16:00] like, situation kind of discovery questions.
Or if you're a developer- Mm ... it's, you're gonna be asking for requirement documentation or, you know, more technical specification than a person like me would be using because I'm, I'm hoping that the, the code that it gives me is good because I, I don't know it, right? Mm. You know, there's g- there's gonna be a line there.
So that, that, I think whenever that changes for an individual, you should definitely revisit your instructions and kinda update it at that point. but the other one that I've been struggling with personally has been prioritization.
Dave Dougherty: Mm.
Alex Pokorny: It's also really easy to do a crazy amount of research, come up with to-do lists that are miles long- Mm
and super involved And then think about, oh yeah, well, the rest of my life also has a million other to-do lists that are a mile long. Like- am I really gonna do any of these things that I was just talking about? And I've started getting a lot stronger with pushing back on, "Oh, y- you should do this, this, and this."
And it's like, [00:17:00] okay, but what's the like ... What if I don't? If I don't do this particular repair to my house, like, what, what really is gonna be the, the, the, like, the failure point? And eventually it gets down to the point of like, yeah, it didn't really get you a whole lot. I mean, you're gonna spend three weekends doing it, and you're gonna maybe, your driveway will last one extra year or two extra years.
I'm like, uh, no. No, that is not worth it in my head. and that, that's a piece I still struggle with, and honestly that I think in general is just trying to figure out how do I prioritize and kind of mentally kinda clear out- Yes ... some of that excess stuff that's out there, or the pending things. 'Cause if I ever ask it, like, what was like the last to-do list things from the last two weeks, it'll give me a laundry list of stuff that, I don't know, 10% is realistically I'll do.
The rest of it, no. Yeah. Like, it, it thought this was like a thing I should do, and it's like, no. No. I'm glad I'm not gonna do that.
Dave Dougherty: Well, and so that's where I have it connected to Asana, [00:18:00] and I have different- Yeah ... projects for different projects.
Alex Pokorny: Oh, man. More pings. I don't know.
Dave Dougherty: Um-
Alex Pokorny: Does it work for you? Like, is that helpful to kinda like distill it that way?
Like, do you find yourself tackling it, or do you find yourself like feeling guilty by ignoring it? Like-
Dave Dougherty: Oh, no, I don't feel guilty. This is actually- Okay ... I've discovered this is a superpower. I very rarely feel guilty about anything. which, no, it's not a psychological problem. I'm fine. I'm normal.
Like
Alex Pokorny: I'm glad that you immediately referred to that. Okay, continue.
Dave Dougherty: But I, 'cause I, to your point, when I first started building out the to-do list and like, all right, good, you can help me with all the projects that I wanna do, and like I'm such a sucker for a big, hairy, audacious goal, right? Yeah. that I'd quickly get overwhelmed. [00:19:00] And so that's where, all right, every year for the last five years, I have fallen into this routine, and I've been doing this, I mean, for longer than five years, so I mean, I know, I kind of know the pattern.
But like, you know, December I reflect on how the year went. January I prep for the next year and what I want to accomplish for the year. And then by March, I would forget about it, and I would just work on the stuff that, I knew was kind of a priority. Yeah, yeah, yeah. But-
Alex Pokorny: Yeah ...
Dave Dougherty: how much I was actually, you know, tackling that.
So this time around, I linked... I have, again, it's a free Asana account, so it's not like, you know- Yeah ... it's not some crazy setup. they're linked together, and I said, "Go in, create a project for 2026. Here's what I wanna do. By the [00:20:00] end of the year, I wanna be able to say this. If I can't be able to say this, that would be considered a fail."
Alex Pokorny: Okay.
Dave Dougherty: Right? Chunk it out into quarterly blocks so that we know whether or not I'm hitting the milestones. And then, for the podcast, we launch every Tues- you know, every other Tuesday, and then we do this, da, da, da, da, da, da, and here's kind of the content frequency of things, the kind of the rhythm- Sure
of things. So then you have these repeatable events. oh, by the way, I coach basketball during these months, and, I have to be a dad. I have to, work a full-time job. I have, this, that, and the other. Sure. So whenever I say I'd like to do something, ask me, "Okay, how many hours a week are you gonna be able to devote to this, honestly?"
Alex Pokorny: Yeah.
Yeah.
Dave Dougherty: so it pushes back [00:21:00] on me with that. Like, "Okay, is this a two-hour thing a week?" Or "What are you gonna do?" And then a lot of times it'll just be like, hey, man, I, I found out that the last two weeks I just needed to watch movies instead of work at 9:00 PM, 'cause I, my brain needed to break, right?
Alex Pokorny: Yep. Yeah.
Dave Dougherty: so yeah. I feel that. I didn't do any of those. The other week, I realized I hadn't updated the project tracker for a really long time, so I just went to it and I said, "Hey, I've launched all of the tasks associated with, the Enterprising Minds podcast show through episode 80 whatever." mark all those as done.
And then it goes, and it marks all of them as done, and then, that way it's, it's updated and, you know, I have Asana also tied to Gemini so that Gemini, with its daily updates, I get these [00:22:00] reminders of, you know, here are the tasks that are, in your u- upcoming week. Great. Thanks. so you get these little reminders, and then you're like, "Okay, cool, yeah, I have to do that." you know, you- Yeah ... you get your normal kind of rhythm to it. but then also, like in June, I sat down and said, "Okay, I've been working hard on these things. This is what we said we were gonna do. Tell me how close I am to actually, like, staying on track."
All right? And then it goes and it analyzes the- Sure ... Asana stuff to then tell me, "Okay, you've gone through X number of tasks towards this thing. If you have any analytics from, you know, these channels, I'll analyze those in addition to the amount of work that you've accomplished to make sure that it's the work that's actually doing stuff."
Alex Pokorny: Yeah.
Dave Dougherty: So that was cool. But then it was ... Then it became the, okay, I gotta go download all this, all these [00:23:00] spreadsheets from all these different, tools, because none of them talk to each other. Yeah. That's the thing ... so then I just download all these spreadsheets, upload them, and then it does this big analysis of it and, and then tells me.
But, you know, that's why I'm, I'm trying to build in these kind of checkpoints along the way to then, test that and make adjustments or, you know, whatever else. 'Cause I also know there's some seasonality to the way that I work. I tend to be really creative, in the fall and winter, where spring and summer tend to be more just, like, get stuff done.
Alex Pokorny: Yeah.
Dave Dougherty: I don't know why.
Alex Pokorny: Yeah.
Dave Dougherty: I just have noticed it, and I don't fight it.
Alex Pokorny: Yeah. I've, I've noticed more of that myself. It's funny, I've ... I'm a fan of journaling, and I've definitely realized that I don't ever read prior entries or anything like that. It's just a- Yeah ... kind of current state kind of thing.
Dave Dougherty: Yeah.[00:24:00]
Alex Pokorny: But yeah, I definitely have patterns to myself as well. Like, I mentioned before that I'm a fan of woodworking, but I'll do that usually for a couple weeks to a month or two, and then after that it is, yeah, straight video games for, like, a couple of weeks or a month. And then-
then the next project or something like that happens.
And if I'm in kind of like one of these creative spaces, I'm not really doing either one of those.
Dave Dougherty: Right.
Alex Pokorny: I'm doing something else or some other form of a, like, relaxation sort of a thing to deal with. I mean, I was up till, what, 11:00 last night working on this random small business thing. But it was a fun thing for this week, and I don't know, maybe I'll stick with it next week or, you know, I'll set it aside because I'm kind of satisfied with the way the project kind of concluded too, of like-
Dave Dougherty: Right
Alex Pokorny: you know, there's that point too of like, yeah, I can throw a couple hours at this because I'm curious, but is it worth a long-term [00:25:00] project?
Dave Dougherty: Right.
Alex Pokorny: And that's a much bigger question for me, and that- that's a consistent kind of question that I always have with- Mm-hmm ... any of these things. Like, they're fun, but- Right
it's ... It was also a random question that I just was having on my mind when I was bored driving around, like, you know, doing errands and stuff. Like-
Dave Dougherty: Right ...
Alex Pokorny: that was it.
Ages Stages and Time
Dave Dougherty: Well, and I think part of it too is ages and stages, right? Because, like-
Alex Pokorny: Yeah ...
Dave Dougherty: you would,-
Alex Pokorny: you
Dave Dougherty: and Ruthie have very- much younger kids than I do.
so- True ... your ability to pursue other things is- Both true ... much more limited.
Alex Pokorny: You know? Yeah, it's a couple random hours here and there, and they're kind of stolen hours from- Right ... sleep or from something else.
Dave Dougherty: Yeah, so d- like watch out world, when we hit mid-40s-
Alex Pokorny: Yeah ...
Dave Dougherty: in a while We
Alex Pokorny: finally start doing stuff.
Dave Dougherty: Despite what y'all think, in a while.
Alex Pokorny: Yeah. Then things might change. [00:26:00]
Hopefully I'll just- Yeah ... get outside more.
Dave Dougherty: So yeah, it's been interesting. But, speaking of, of ages and stages, just kind of quickly, I've been thinking about this recently as well with, the kind of annual turnover of, of corporations, Yeah ... and the kind of stages of the year, right? I mean, we're... I know we're coming into the latter half of the year because I started seeing the latest Call of Duty promo, and that for me is when I know I should go get my flu shot because without fail, whenever the new Call of Duty comes out, I get sick and I spend a week playing that while feeling horrible.
Like
Alex Pokorny: That is both... That is the perfect definition of like bittersweet. It's when you're sick, but you get the new Call of Duty and you're playing it.
Dave Dougherty: Yep. So yeah, this is great. I finally have time to, you [00:27:00] know- Yeah, you really do ... lay down and do it, but I can't share it with anybody- With your schedule
'cause nobody wants to be around me. That's really funny. Um. Yeah, I got this Call of Duty cold. Yeah. Sure. Sure.
Yeah.
Alex Pokorny: No, seriously.
Dave Dougherty: but anyway, the, the thing- Yeah ... that's always driven me nuts with corporations are the ones that will fire people right before Christmas. Yes. I have some strong language for those corporations.
Yeah. you know, at least let them have some family time without having to worry about stuff, Like, that's- Yeah ... just some basic human stuff. but so that's coming. And so I was thinking of that, and we had talked about it recently, or at least what feels recently, on, if you're laid off, how do you, like, start something?
How can you use AI to help start something? And I thought it'd be interesting to revisit that. Sure. And, you know, [00:28:00] Alex, you were kind enough to throw something in the chat. And like I said, it wasn't that long ago, Yeah ...
that we looked at this, and already a lot of stuff seems to be- Yeah ... outdated. And I was really surprised by that.
So do you want to quick run through, um-
Alex Pokorny: Sure ...
Dave Dougherty: what you said we could do?
Layoffs and Job Search Mindset
Dave Dougherty: Now, the scenario for this is you've been laid off. You have to quickly find, you know, something. Yep ... how do you either find something right away or put yourself in the best situation to find something right away, when the market's still not all that good?
Um.
Alex Pokorny: Yeah, and that's was the thing when I got laid off. I- I... For me, it's always the systems behind the symptoms kind of a thing. I- I- Right ... don't like not understanding basically, like, the reason why, which I think with layoffs is mentally can be pretty taxing. Um-
Dave Dougherty: Yeah.
Alex Pokorny: That's an
Dave Dougherty: awful spot to be, 'cause-
Alex Pokorny: Yeah
there's
Dave Dougherty: not really [00:29:00] a reason sometimes.
Alex Pokorny: There, there really isn't, and it's, it's a very frustrating thing. but then I kind of created kind of investigation kind of approach that I usually- Mm-hmm ... take towards things like that, of trying to understand then, you know, with the job application process, like how do I investigate that to basically understand that better?
Like, there was a meetup I went to once, and there was some people who were switching from very, very different careers, like a professor and wanted to become a marketing director, and it was like, "Well, I've been working for 10 years as a professor, so I should be able to be a marketing director right away.
And I've been searching now for five years, and I haven't found anything." It's like- Yeah. That, that kinda makes sense, um, 'cause you don't have any experience. It's clearly adaptable. Yeah. I was like, there's so many things here to say, but, yeah, you don't have any experience, and your resume literally says something completely different than what you're applying for.
So I'm, [00:30:00] I'm not surprised that you haven't got many interviews. but yeah. So I started, putting together a bit of a kind of meeting schedule and topics and stuff like that, and then people started asking me to kind of run through that with other people. Uh, ended up being like 14, 15 people over the course of a year that I did this whole thing with.
but this is three, four years old now So it's a little dated, and there's definitely ... AI doesn't really come into it because of that. This is pre.
so yeah, I can run through some of it, but let me kind of hit the, highlights of it because I think there's a little too many, you know, points here.
one of the main things is basically is there is a very emotional aspect of being laid off. It is a breakup because it's not only you and the company, and it can feel very personal even when it is impersonal.
but [00:31:00] there's a lot of individuals that you talk to in a frequent basis, and it could be just work-related.
You don't know them beyond, the job, but you will lose communication to all of them very suddenly, and it's not by your choice. It's kind of like being broken up with versus being the one breaking up the relationship.
Dave Dougherty: Kicked out of a friend group kind of thing.
Alex Pokorny: Y- yeah, and it, and that's really painful.
As much as, you know, you might really enjoy and look forward to that Friday meeting that you always meet with, you know, a certain colleague or something like that, and yes, you'll keep in touch, which means a couple times a year at most really. Let's be realistic. It's not the same. you're gonna ... All of those connections suddenly get broken upon you, right?
So-
Dave Dougherty: Mm-hmm ...
Alex Pokorny: that's painful. It's funny, the second thing was talking about remote versus in-person application, talking about the difference of handing in paper applications. So yeah, that's dated.
Job Hunt Systems and Boundaries
Alex Pokorny: headspace, that's a big piece. [00:32:00] Um, and I think that's still worthy of anyone in any part of it whenever you're slightly, even slightly concerned about your job.
Put down kind of your bare basic requirements and question each one of them. So salary band, does it have to be the same or higher? If it was X amount, 10% lower, 15% lower, 20% lower, what's the point where you say, "Absolutely no, I can't take on, you know, minimum wage jobs or retail jobs. I have to at least be making X"?
That's good because now you have, you know, a price floor for your job applications as well as, you know, during when negotiation happens, you already know what your number is. That's not a surprise of like, "Oh, I don't know what I want." No, You have a very good idea of this is it. And what I took with that too of like, you know, remote versus in person, corporate versus small business, you know, what, what's your ideal, and work that down.
Let's say it's company size. You want to work at a global multinational. Great. That's one. For [00:33:00] the first three weeks, that's all you should apply to.
And then after that point, and you can put a calendar invite on yourself, after three weeks, you apply to those jobs plus the next tier down. So you're still doing this ideal thing, which means at the end of the day, you will still get the best job you could have possibly gotten, but you're not being overwhelmed with all these other ones that, quite frankly, are extraneous and not necessary for you to apply to right now.
So you're going through this process a little bit more intentionally, trying to make sure that you're happy. It's not necessarily just a, what's now called a kind of a bridge job where you just find something.
Instead, it's something where you feel like, yeah, you know, I could, I could stick around doing this, and I'm satisfied with it.
It's not just every day I'm like, "Man, I should be job searching again while working," which to be honest, you don't have time to do that. Nobody really does. it's a nice thought, but-
Dave Dougherty: Or if you do- Very difficult ... you're exhausted, and you're not actually- Exactly ... relaxing. Yeah.
Alex Pokorny: Yeah, and that's the thing is there's a piece of this too I [00:34:00] found was, two days a work week I would take off, and I would call them, HR catch-up days or mental health pause because quite frankly, there is only so many applicable jobs out there, and that's it.
So once you start applying to just endlessly scrolling on LinkedIn for jobs or whatever, that's painful to you and not effective. so I purposely always schedule, there's like Tuesday, Thursdays I would go. I had a lot of house projects and random stuff that I would do. Whatever it was- Right ... chores, errands, anything to get my mind off of it.
And if HR from any of these job applications sent out like, "Hey, let's set up a interview," I absolutely would respond back to them immediately. Like, you know, I'm always ready with that. Right. but I would stop. I would, I would not try to just all day, every day. That, that you just burn yourself out. I think, I think that another piece that would still be true is the [00:35:00] three-week cycle.
Basically think of it as a funnel. Week number one, you're filling it with applications. Week number two, the people who are quick about scheduling interviews will do it. Week number three, those who are late about scheduling interviews would do it. And week number four, do not assume anything from week number one is valid anymore.
It's, the funnel is empty.
So the only way to kind of keep interviews coming to you is to keep the funnel full, and you can't just apply to the one job that you think is the great one and then just wait. That's not realistic, which can be very painful to see.
Dave Dougherty: Right. And like the annoying thing, and we've covered this a little bit too, is, you know, the amount of companies that are, posting jobs and then reposting jobs- Yeah
and then reposting jobs. And so, you know-
Alex Pokorny: And Facebook's terrible with that. Yeah.
Dave Dougherty: Yeah. And so, at, at this point it's part of the game, unfortunately. Yeah ...
but also the thing that I've been thinking about too with this is not just know your number for [00:36:00] salary, but who are gonna be your first five phone calls?
Who are the ones that either own their own businesses that might need help that you could do some quick freelance projects for? You know, maybe they could do you a solid. Uh-huh. Yeah. Yeah.
Do you know anybody in the agency world, if you're a marketer, who, you know, where you could just say, "Hey, let me contract, or ghost a project for you."
Yeah. if you need any help," right? "I'm available." and then, so setting up a consultancy or doing the freelance stuff is fairly quick. You know, we talked about this in the last one of our previous episodes. Yep ...
but yeah, I've been thinking about that too, where it's, okay, do you have ... Then you get into the whole, how, what's your positioning and da, da, da, da, da.
But that's too- Yeah ... involved for, "I've been laid off. What the hell do I do?"
Alex Pokorny: Yeah.
Dave Dougherty: I would [00:37:00] say first go get a tub of ice cream. Yep ... call your friends.
Alex Pokorny: Agree. Yep.
Dave Dougherty: And, uh, take the day. Yep. Feel the feels, and then hit it hard the next day.
Alex Pokorny: Yeah.
Dave Dougherty: You
Alex Pokorny: know? You have to. I mean, mental. Yeah. there's- There's a headspace change that is extremely different that happens between, you know, the last day that you had a job and the first day that you don't.
Right. Like the schedule used to exist, now it's gone.
The pressures and initiators of those pressures used to be largely external, and now they are gonna be 100% you motivating you. Not somebody saying, "We have a deadline that's coming up, and now you have to work." Right? I mean, there's, there's so many changes, and yeah, if it's a day, great.
If it's a week, do it. I mean, whatever it takes to kind of get you going again. And if it's bum around the house, start doing some errands, and chores, and laundry, and whatever else it takes- Mm-hmm ... to get you to start feeling productive again, [00:38:00] do it. Take some time to figure that out.
Dave Dougherty: Right.
Alex Pokorny: there's a lot here as I'm kind of running through this list-
Dave Dougherty: Mm-hmm
Alex Pokorny: that'll basically kind of help you from a standpoint of job searching circa a few years ago.
AI Tools and Next Steps
Alex Pokorny: But I swear a lot of it is gonna change because of AI. Like, I've seen- Well,
Dave Dougherty: I think there's, there are some basic things that we know to be true even in the era of AI, right? Which is your friends are gonna help you.
Alex Pokorny: True.
Dave Dougherty: You will find out- No excuse ... who you thought were friends who are not. That happens every time there's a life change.
Alex Pokorny: Yep.
Dave Dougherty: you know, knowing that those are true, fine, great. The, flip side of it is, you know, with your analytics and Cloud Cowork and, and everything else, it is so much easier now to [00:39:00] spin up stuff.
True ... you know, like getting that resume and that cover letter that's actually aligned with your experience to then also be aligned with, the jobs that you are applying for, and make su- Yeah ... making sure that they're sort of ATS aligned and, and everything else. Yeah. That has become much more easy.
which is wonderful 'cause that, for me at least, that's a huge headspace thing where it's just like, "Ugh, so tedious. I don't know if I wanna do it." Yeah. Well, now there's really no excuse because, you know- Yeah, a
Alex Pokorny: lot of people pause on that resume update, and there's no real reason not to. Like, you can also have it ask you questions.
You know, set it up that way of saying, "Ask me a bunch of questions about my job. Here's some jobs that I think look cool."
Dave Dougherty: Right. "
Alex Pokorny: And then help me write a resume, because then it, it's not hallucinating random stuff based upon your job title than, you know, the zero context you gave it. Instead, it's asking you questions of, "Have you ever had a project like this?"[00:40:00]
"No." "Have you had a project like this?" "Yes." You know? Right. Like, it can ask you those questions, and you can set it up to feel confident with what you're creating and not AI slop it. You know, instead you're- Right ... doing something that you can feel proud of.
Dave Dougherty: Well, and I think there are a couple ways of going at it, that way.
One would be to have it interview you for the types of jobs that you are interviewing for.
Alex Pokorny: Yeah.
Dave Dougherty: Right? Check me out to see if, I answer the kinds of questions that a senior product marketer would get, right? Sure. That's step one. Step two, or, door number two, would be to just, like, sit down with WhisperFlow, Voice Memo, whatever, so that you can just talk and not have to type all of this out, 'cause you'll, lose stuff if you have to type it.
Just [00:41:00] start telling stories of your career. I went to the university for this, I did that. These are the cool projects that I did at the university. That experience led me into going into this, and then from there I did that, da, da, da, da, da, da, da, da, da, da, da. You talk for 20 minutes, half hour, hour, whatever your staying power is, using, you know, using a tool like Descript even to get the transcript to then put it into, Claude or ChatGPT or whatever else.
You can then go leverage all of that and create case studies that you can bring up in interviews or put on your website. You can then figure out, this is how I position myself into the market, because here are the stories that I naturally bring up and the projects that I'm naturally proud of, which puts me towards these particular things.
you know, there's a lot of different ways that you could go about doing it. And again, you're kind of outside your [00:42:00] head, right? You're not totally alone, uh, where you have to motivate yourself to go and push through the hard thing. Because, I mean, you have somebody dictating it and helping you draft all of the things and, you know, based on what I told you, what are the skills that I should be featuring on my LinkedIn profile?
Alex Pokorny: Yeah. That's a really good point. And also, if you don't know what kind of job titles fit this kind of a person.
Dave Dougherty: Right.
Alex Pokorny: You know, like what kind of job titles should I be looking for considering my interests are here and not here? I had to do that once because I was kind of curious of like, you know, what other kind of jobs are out there sort of thing.
And it said... I asked it of like, ask me some questions of the job duties, of the day-to-day tasks of people who have, you know, similar experiences to my own based upon my resume, and just tossed it my resume or my LinkedIn copy paste.
Dave Dougherty: Right.
Alex Pokorny: Kind of threw it in there. and then I had to kind of- quiz me and ask me a bunch of questions about other, [00:43:00] related fields or associated kind of job titles and stuff like that to my own, and found that, yeah, there's some that are kind of interesting and some that honestly once you get in the day-to-day of it, no, I couldn't handle d- doing that for six months.
Like, there's no way.
but that was helpful at least because it kind of gave me some, again, some boundaries- Right ... to kind of search within versus, I don't know, that looks cool. I guess I could do that. You know? It kind of gets rid of that part and instead says, you know, these are realistic and things that I would actually want to do.
But yeah, I mean, even your Asana idea, I mean, you could apply that to this too, considering you have a free version of Asana of-
Dave Dougherty: Mm-hmm ...
Alex Pokorny: you know, here's what I should do to update my resume and get my LinkedIn started and stuff like that, and break that into, you know, you can- Digest it in little chunks
atomic habits or whatever.
Dave Dougherty: Yeah.
Alex Pokorny: Yeah, small enough chunks where it seems reasonable versus a laundry list from some random person on LinkedIn who's spouting something like, "Here's 15 things you need to do immediately." Ah, geez. Right. I think dealing with my mental health is number 1 through [00:44:00] 14.
Dave Dougherty: Right. If you're wearing chinos, you're old.
Since when? What? what-
Alex Pokorny: What is this random junk?
Dave Dougherty: What does that have to do with anything, LinkedIn? Stop trying to be TikTok. Um-
Alex Pokorny: Yeah.
Dave Dougherty: Yeah. No, so anyway, for everybody, I hope you don't find yourself in this situation. but should you, know that you're not alone. Even though it feels it, you're not alone.
And you know, there are, there are some ways to, get through it. the next episode will be in two weeks. Please like and subscribe. Enjoy the beginning of fall and all of the joys of football season and kids being back in school and yeah, all the good stuff. So like, share, subscribe, go check out [00:45:00] Pathways, go check out enterprising-minds.com, and enjoy the two weeks to come.
