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173: Stop Selling Yourself Short: Quantify Your Impact and Land Your Next Role with Josh Czupryk

In this episode of Ed Up L&D, host Holly Owens interviews Josh Czupryk, the creator of the K-12 job board blast. They discuss Josh's journey from teaching to entrepreneurship, the challenges educators face when transitioning careers, and the importance of quantifying experiences in resumes. Josh shares insights on the current education landscape, opportunities for teachers in L&D and EdTech, and practical advice for job seekers and aspiring entrepreneurs.

In this episode of Ed Up L&D, host Holly Owens interviews Josh Czupryk, the creator of the K-12 job board blast. They discuss Josh's journey from teaching to entrepreneurship, the challenges educators face when transitioning careers, and the importance of quantifying experiences in resumes. Josh shares insights on the current education landscape, opportunities for teachers in L&D and EdTech, and practical advice for job seekers and aspiring entrepreneurs.

 

 

Resources mentioned in this episode:

 

Guest Contact Information:

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Holly Owens (00:00.814)
Hello everyone and welcome to another fantastic episode of Ed Up L &D. I'm Holly Owens and I'm your host and I am super pumped. So excited for the guest that I have here today. I have Josh Czupryk did I say that right? Yay! And he has entered the chat. Welcome Josh.

Josh Czupryk (00:17.757)
You did

Josh Czupryk (00:22.523)
I appreciate the invite.

Holly Owens (00:24.718)
I'm really excited to get into all things. I've been watching you. I don't want to say stalking you, but watching you on LinkedIn World, doing all the amazing things you're doing with your K to 12 jobless, having your business, all your education experience. But before we dive into all that, tell us your story. Who are you? How did you start your career? All the different things. We want to know more about you.

Josh Czupryk (00:48.307)
So I can typically do this in one minute or less, so I'm gonna time myself. But I was born and raised in the Florida Panhandle. Both of my parents were teachers for over 40 years. My dad is actually in his 70s and entering his 47th year this fall. So I got some lifelong educators. I went to the University of Florida. I did not do anything with education.

Holly Owens (01:10.51)
Absolutely.

Josh Czupryk (01:16.691)
I went to the College of Journalism and I wanted to do public relations. Before my senior year, I did an internship on Capitol Hill in a Senate office doing press stuff and I hated every moment of it. And that really just like knocked me off my horse. And so when I got back for my senior year,

I joke that I went on a date with a girl, but beforehand she wanted to stop by and grab pizza from an organization called Teach for America. She didn't end up applying and I like watched the video. Transparently my sister was in Teach for America and I had no idea what my sister was doing. And then like watching the marketing video, I like started crying.

Holly Owens (02:00.828)
it's not like the Sarah McLachlan animal one, is it?

Josh Czupryk (02:10.215)
I mean, it was close. And I just was like, well, maybe, you know, maybe this will give me two years, right? And then I can kind of figure out grad school or law school, you know, like I'll figure something out. So you get in, you do your two years doing Teach for America for people who aren't familiar. They recruit you to do two years in an underserved community teaching. I got my license and then I was like, why would I ever not do education?

Holly Owens (02:38.456)
Right.

Josh Czupryk (02:39.547)
So quick evolution, I coach teachers for a years. I worked for some charter school networks doing data. I actually missed being close to the classroom. So I went back to being an assistant principal, quickly rose up, skipped the principal seat and became a principal manager. And then wrapped up the last nine years being some iteration of an assistant superintendent, both at charter school networks and then most recently a school district.

So for the 18 years, seeing the classroom level, seeing the assistant principal level, seeing the district office level, seeing the senior leader level, and bring all of that to what I do right now. Very brief origin of the jobs blast was three years ago, about three and a half years ago, I wanted to leave charter school. I had gotten to the point, loved charter schools, so many charter schools on my board.

Holly Owens (03:31.661)
Yeah.

Josh Czupryk (03:36.967)
big fan, work with a number of them, but I had burned out. And so from the moment I knew I wanted to leave to the moment that I had my offer to be an assistant superintendent at Tennessee's number two school district in the country or in the state was four weeks. Okay. And I was not alone. I feel like people sometimes move through job searches with like cohorts of friends that are also job searching.

Holly Owens (03:40.491)
Yeah.

Holly Owens (03:54.902)
Wow.

Josh Czupryk (04:06.835)
And my friends were taking a lot longer. And when I took a step back and realized I am a straight passing white man, and my friends were really talented black women, and I realized there were these invisible doors opening up for me and these invisible kind of privilege, right? Like that is the word we use for it. But that was totally working in my advantage. And what I realized was my friends didn't have the same

perspective to see what all was out there. So the first job last was not a Google sheet. It was a Google doc where I had just copied and pasted roles from Teach for America and TNTP and the Achievement Network, like all of these nonprofits, and was like, hey, just start applying here, right? And two weeks later, I copied and pasted again. Two weeks later, I copied. And then they would say, can I share this with somebody? September, it became a spreadsheet.

Holly Owens (05:02.94)
All right.

Josh Czupryk (05:07.013)
March of that year, it became a website and a spreadsheet. So it really did, to your point, just organically take off. And now I...

Holly Owens (05:14.946)
You went viral if from my, you went viral. That's what happened. That's what happened.

Josh Czupryk (05:19.825)
I went viral. So there 12,500 subscribers. It's free to subscribe. And there are 53,000 followers on LinkedIn. So to your point, like, word caught on.

Holly Owens (05:28.928)
Yes. I love, and I love that that happened for you because it's so, it's so much valuable information. And like, you really bring the different, not a different perspective, but you understand K to 12 and you understand it in a way that, you know, I've been out of the K to 12 game for, I don't even want to say it cause it's going to date me since 2011.

And, you know, but still the same things kind of exist in that industry, like you're talking about burnout and people just looking to do different things. I think one of the things I'll mention and, you know, ask you about is there's often this sense of guilt shifting to something else for transitioning teachers, you know, maybe in combination with that imposter syndrome. And then on top of that, you have to kind of deal with the trauma of leaving the classroom.

Josh Czupryk (06:00.827)
Thank you.

Josh Czupryk (06:06.34)
Thanks

Josh Czupryk (06:17.591)
Thank

Holly Owens (06:17.642)
I remember my first time out of the classroom and I also coached field hockey is I was crying in the fall. I was crying for field hockey season. I missed the girls, I missed the girls, I missed the students. I was like, my God, what did I do? Did I make a mistake? But one of the things I want to ask you is like, how do you think it's best to deal with all that or even talk about your own experiences coming out of K to 12?

Josh Czupryk (06:42.375)
Yeah. So first, just directly, I think it comes from a sense of patriarchal sexism. I think that we associate guilt with leading professions specifically around teaching and nursing. Those are the two that immediately come to mind. And there's a great book called Teacher Wars. And I would encourage everybody to read it. I can't remember. It's in it's I read it about once every.

Holly Owens (06:57.774)
Yep.

Holly Owens (07:05.838)
It's gonna be in the show notes now.

Josh Czupryk (07:10.739)
year to two years. And I read it when I was getting my masters in 2016. And it blew my mind. But it's essentially about the history of teaching and the fact that we expected women to be teachers and men to be superintendents from like the 1600s. And that is the origin of America. We do not give superintendents and assistant superintendents guilt for leaving their roles and they have higher turnover than we do as teachers. I'm saying we.

Holly Owens (07:26.753)
Yeah.

Holly Owens (07:38.999)
Right.

Josh Czupryk (07:40.485)
I started my career. recognize this is just super difficult.

Holly Owens (07:43.234)
I mean, it is a we. We are part of that community for life, honestly.

Josh Czupryk (07:47.527)
But we don't give superintendents and assistant superintendents guilt. We don't give them guilt when they leave to go be consultants. No one's giving me guilt. Not a single person's giving me guilt for going out on my own. But we do get teachers' guilt. you should do it for the kids. And I'm not saying that we aren't right to this profession because of the mission-driven foundation. But that is not an excuse for gas lighting or poor conditions or poor pay.

And so I think until systems respond with the working conditions that will attract and retain people, no one should feel guilt about doing what is right for them.

Holly Owens (08:22.5)
my gosh, that well said. And I think you're right. I totally agree with you. I felt so bad. I felt so bad. Like I had let people down and I had let myself down because I committed to saying that that was what I was going to do for life. And then I, there was a shift or a change and I fell in love with ed tech and training. So it's what happened and it's okay. you just saved me a bunch of money on therapy, but why am I just pointing that out?

Josh Czupryk (08:34.547)
Thanks.

Josh Czupryk (08:41.031)
So.

Josh Czupryk (08:50.635)
But I think it's so important for people to remember at the end of the day. And again, I'm going to date myself. just turned 40. But my parents, you know, but our parents' generation, you know, my parents have taught for over 40 years and they were with the same district that entire time. They also had pensions. They also had tenure.

Holly Owens (09:00.172)
I'm 41.

Josh Czupryk (09:15.015)
They had the policies and the practices in place to reward people to stay for long, extensive periods. Districts and charters now have at-will employment. There is no tenure. You have 401Ks typically or much smaller pension benefits. So the financial structures and policies that people approach the teaching profession with, it's different now. And so I just...

Holly Owens (09:22.52)
Right.

Josh Czupryk (09:42.513)
Whenever anybody messages me feeling shame or guilt, I'm like, your employer will feel zero shame or guilt about conducting a riff or a reduction in force. so feel free to be as loyal as you feel you ethically and morally should be. And my encouragement is to always have irons in the fire, have an updated resume and know where you might go next.

Holly Owens (09:52.642)
Yep.

Holly Owens (10:05.75)
Yeah, that's great advice. Absolutely. You know, we're seeing a lot of transitioning teachers coming into the L &D industry. That's like, there's a place for them in instructional design, instructional technology, ed tech, customer success, all those different things. What's your take on that? You see a lot of different jobs. You see a lot of different postings. all, you know, I do job postings too, but what's your take on like how teachers can, you know, transition into these roles and feel

Josh Czupryk (10:14.643)
Mm-mm.

Holly Owens (10:35.674)
comfortable doing so.

Josh Czupryk (10:38.675)
100%. So I think you're 100 % right about instructional design. I will say just being really timely that because the title funding has been suspended or I guess they just released it today is the 22nd rate. We don't know the status of federal funding, but because we don't know it, neither do chief financial officers and charter school networks and school districts.

Holly Owens (10:47.17)
Yeah.

Holly Owens (11:00.322)
Right.

Josh Czupryk (11:06.501)
And they are spending significantly less money expecting title three reimbursement, which is what you give for professional development than we had before. So exactly what you said, Holly, about customer success in sales. I'm seeing more customer success in sales positions that I am instructional design positions. I'm not seeing a full drop off in instructional design, but revenue generating.

And from her people funds, right? Like, you're going to need to have. Some type of a reading or math program in an elementary school classroom for reading rotations. You got to have it and if that means you spend per pupil money on it, it means you spend per people money. The professional development you have at the beginning of the year where you pay somebody to come in or bring in a nonprofit to do an instructional design review. Important.

Holly Owens (11:45.728)
Absolutely. Yep.

Josh Czupryk (12:01.703)
We're not saying it's not important and we're not saying it's not a priority, but if you only have so many dollars and the federal funds have stopped, it may not be as priority. This is similar to last summer. I remember pulling the data and I'll say like one thing that I think makes me and my hero, Chelsea, who runs EdSkip, she, like I tell everybody.

Holly Owens (12:10.252)
Yep. Wow.

Holly Owens (12:23.342)
I tell everybody to hi I've started from the beginning I've been an error with Chelsea. I love her

Josh Czupryk (12:33.074)
So I tell everybody like follow. So I think what we bring is she has her PhD. I'm almost wrapped up with my EDD and we bring this data analysis piece of like, when we're looking at the jobs, it's we're not just sharing them, but we're like, here are the trends. Here's what we're seeing with salaries. Here's what we're seeing with postings. Last June, I saw this spike in fundraising and development roles at nonprofits and at charter school networks. I mean, we're talking like 30 to 90 roles in a month.

Holly Owens (12:59.692)
Wow.

Josh Czupryk (13:03.527)
And I was like, why would that happen? Well, the stimulus was ending with all of the money that was going to schools. And so people were immediately replacing them with fundraising teams to replace the stimulus money. Right. And I think teachers, number one, again, imposter syndrome doubt themselves, but you know,

You manage 30 client relationships a year if you're in elementary school with families and upwards to 120 to 150 in middle or high school period. You call them customer relationships. If you have them for multiple years, you have enduring customer relationships, multi-year, two-way customer relationships. We have attendance data. If attendance data has gotten better, you built a strong culture and climate that has increased this metric.

Holly Owens (13:35.797)
Yeah.

Josh Czupryk (13:55.739)
If you have, you know, growth data on NWA map or IREDi or any type of a norm reference assessment, you can show, Hey, when I focus and build instructional design or implement high quality instructional materials, we see the X percent of students grow X percent of way, know, but I think teachers are so shy at times because we are, we drove them in this country to be shy about quantifying that the way I feel like you pivot and translate is you quantify.

Holly Owens (14:21.908)
Yeah.

I think that's a great point. And also too, I think the one thing we've also from that perspective in terms like testing numbers, I taught a status as course. So everything that my whole performance was based off of like what my students did. So at the time I really didn't understand the data and how important it was to kind of understand it. So I think it's an important point to make that it's okay to quantify that and you know.

use that in your professional materials so that if you are transitioning out of the classroom into a corporate environment per se, let's say that you have, you understand that data and analytics are important, ROI, OKRs, all the different things. So that's a good point.

Josh Czupryk (14:55.347)
100%.

Josh Czupryk (15:10.867)
The biggest thing I always push people on is some people send me and I'll periodically say, send me your resumes. You've probably seen it on LinkedIn, right? I'll look at your resume. Art of that is a qualitative analysis for me. So it works for me. Like I'm going to give you 15 to 32nd review and very quick high points. But what's really helpful is I start to see trends of, okay, people are leaving out data or okay. People are like, the bullet points are way too long. Right. And so, so instructional design iterative.

Holly Owens (15:17.866)
Yep, yep, yep.

Josh Czupryk (15:40.179)
processing, right? Like, me help people, let me take all this information, boil it down and give people a cognitive framework that they can leverage in order to produce a good resume coming out of the classroom. I've run searches. I've run 20 searches so far this year where I am hiring people for organizations. When I look at resumes, I have to see evidence that I can move you to a phone screen.

Holly Owens (15:51.33)
Right.

Josh Czupryk (16:07.443)
And if you are not going to provide any evidence, I don't have the evidence to say you are able to do this instructional design or customer success role. So I need the.

Holly Owens (16:15.69)
Right. You're not Bon Jovi. We're not halfway there living on a prayer.

Josh Czupryk (16:19.947)
That's it. so, and I think like just letting people know you're going to get 15 to 30 seconds. think more, I think more companies do human screening of resumes than people realize. I think people think it's all AI. I think AI plays a part and I'm sure there are bad actors, but most places have committed to, you will get seen by a human, but they have to see something within 15 to 30 seconds that says, I can move you to the next round.

Holly Owens (16:45.4)
That's a good point. 15 to 30 seconds. I think I told people like they only read like the first third of it. Like the resume. Yeah. Okay.

Josh Czupryk (16:52.339)
If I can find what I need within the first third, I advance. I will spend and go through the whole thing if I can't find it because I just am like, what if it was in another role? know, like, let me.

Holly Owens (17:03.779)
Right, because everybody structures it so differently. Well, that leads me to the question then like,

If that's your person, people take 15 to 30 seconds to kind of look at the resume. How do people set that up appropriately to people always ask me, and I'm sure you get this too, because you do the resume reviews. How do I stand out? There's thousands and thousands of applicants. How do I stand out with this 15 to 30 second thing, which is not quick if you're doing like a sit ups or some sort of gym routine. But if you're you're looking to, you know, impress somebody, what is how do they do that in that?

Josh Czupryk (17:20.817)
you

Josh Czupryk (17:39.805)
First off, the field hockey coach. appreciate the exercise reference. two, I think there's a few things. I think it's very rare that I see like the secret job market, right? Where like there's a secret role created or posted for Holly because we want, you know, now I think that people's networking connections can help them stand out.

Holly Owens (17:39.822)
short amount of time.

Yeah, I love sports, so it's all sports here.

Josh Czupryk (18:07.739)
I do think like messaging, every single hiring manager on LinkedIn is probably more annoying than it is helpful. And I just want to be transparent with people, right? I think replying, I'm interested on somebody's posts that they're hiring doesn't help. think writing a strong, succinct, clear and concise resume helps. so we'll put it in the show notes, but I have a free template that you've probably seen me share.

Holly Owens (18:17.934)
Agreed.

Yes.

Holly Owens (18:36.546)
Yeah, it's definitely going to...yep! I've seen all these things.

Josh Czupryk (18:39.847)
Take the free template, take your resume, put them both into ChatGPT, Grok, or Claude, whatever your choice AI is. Say, take this template, take what I have, translate it, tell me where there are gaps. And it will. And then think that, and then what I would do is I'd take whatever you have produced at the end and say, now, cut the words down to exactly what is minimum needed. Because if somebody's eyes...

Holly Owens (19:07.756)
I need to go do this.

Josh Czupryk (19:11.043)
But if somebody's eyes can't glide over your resume and pull out what they need and, and, my gosh, y'all, the formatting in Europe is expected that you use a profile picture. It just is. In America, I would almost say it's not inappropriate to use a profile picture, but it's going to cause more recruiters to say, Hmm, why did they, you know, like, why did they put a picture or a headshot on their resume? So my advice is don't.

Holly Owens (19:13.88)
Right.

Holly Owens (19:34.926)
Right.

Josh Czupryk (19:38.999)
make it overly fancy, make the content good. This is just like instructional design. I don't need a big publisher's pretty textbook. See, I didn't want to name a big publisher there. I was like, let me catch myself. But I don't need a big publisher's pretty textbook. If I can go on, and I'm going to give Eureka Math or Exodustory Learnings open source, high quality instruction, I don't need to buy the pretty textbook. I can go get really high quality stuff for free.

Holly Owens (19:42.189)
Yeah.

Holly Owens (19:49.614)
Yeah.

Holly Owens (20:05.901)
Right.

Josh Czupryk (20:06.511)
Same with the recruiter. I don't need that really pretty PDF with all the colors. Like I just need something that tells me you can do the job.

Holly Owens (20:15.406)
100 percent. It's like it's like having a conversation when you're having a story being told. And my grandfather does this. He tells you every single solitary detail of the story. So when I call him every day, it's 10 to 15 minutes of him telling me exactly what he did throughout his day and all the points of it. I love him. He's going to be 85 this week. Yeah. But for us, it's like this is like get to the point. And I also say, too, and I don't know if you agree with this, Josh, is that the resume is a very static document.

Josh Czupryk (20:34.045)
With that, congrats.

Holly Owens (20:45.714)
It has no personality in it whatsoever. It's just like boring. It's cumbersome. So like what you're saying the content has to be like what we're looking for. But also too I would tell people, you know, working with clients in the past, like record a video about yourself. Like put a link to a video in there so they can just like get a little, hello, I'm Holly. You know, I do a podcast and all this stuff I'm looking for, you know, just something quick that doesn't necessarily, can. Yeah, yes.

Josh Czupryk (21:08.903)
That's 20 to 30 seconds. Right. Like, and so I did, I gave a job seeker that it's the reason the LinkedIn thing came up. If somebody messaged me a couple of days ago and said, am I helping or hurting myself by messaging every hiring manager? said, you're hurting yourself. Period. I said, now what you could do is say, Hey, thank you for posting this. I applied so excited to go through the process. Like that is so important because.

Holly Owens (21:25.166)
hurting naturally.

Josh Czupryk (21:38.991)
And I very rarely do I find an organization that hasn't built some type of a hiring process. And if you're saying I want to skip the line, the same way people would boo you at Disney World if you tried to skip the line, people are going to boo you and adjust. I know, I know my audience. know my audience. And so I think for me,

Holly Owens (21:50.094)
You said Disney World. I want a fast pass right now. Lightning, lightning lane.

Josh Czupryk (22:01.235)
The lightning lightning thing in it is so presumptuous

Holly Owens (22:05.952)
It's complex in itself anyways. That's another conversation. Go ahead. Yeah.

Josh Czupryk (22:09.212)
But it's so presumptuous, right? And I think it is a turnoff for hiring managers and recruiters, right? But here's what you can say. can say, thank you for posting this. I'm so excited I applied. I'm excited to go through the process. I'm just messaging so you have access to my LinkedIn where my portfolio is in case you have any further questions.

Holly Owens (22:32.238)
Yeah, I love that. I never don't know. No, no, no, no, no, no, no, no. You know what? And that's the thing, too, is like there's something to be said about like the what's in it for me conversation. that gives them like.

Josh Czupryk (22:35.377)
Now go do it to everybody.

Holly Owens (22:50.03)
you're messaging them, you're creating visibility, you're making yourself quote unquote stand out a little bit. You're also giving them access to your professional materials. But the other thing too is I think that people all too often, they don't read people's experiences in their profiles and they automatically, I'm sure you've gotten this, they send you something and they're like, review this for me. They don't even say hi anymore. There's no pleasantries whatsoever. It's just like, do this for me and I'm like.

Hi, I'm Holly. I've been in this game for how many years? I've, you know, yeah. And like, okay, I don't, I'm happy to do like a free coffee chat, but you have to pay me for my services if I'm offering you some of my time. I can't stress to people enough that just simply just saying what you need is not gonna get you anywhere. It's gonna get you a block and no more we're not a connection.

Josh Czupryk (23:22.813)
Yeah.

Josh Czupryk (23:47.091)
That's 100. Yeah, I think it is. People, think society has become so transactional and we are all so used to having our own personal algorithmic feed and everything is catered to us that we then forget how to interact with other humans, especially in a job search. So I love your advice. And I really do think it is, how can I offer value in this exact message?

Holly Owens (23:54.07)
Mm-hmm.

Josh Czupryk (24:12.883)
And in my resume, how can I offer the value long term to this organization? I will also say for people who are freaking out about only being at jobs three to four years, right? That's kind of the norm now. Right. So that was my other piece of advice was I get this all the time of like, should I stay for 10 years? I'm like, I don't know. Do you like your job? Like.

Holly Owens (24:25.934)
you

Holly Owens (24:30.444)
Yeah.

Holly Owens (24:38.638)
Right. Yeah, it's like a relationship. Why are you staying in it just to stay in it? I feel like I feel like there's a lot of correlation between online dating and getting jobs today. Yeah.

Josh Czupryk (24:39.195)
If you like your job and you feel like you're doing great work, stay. And if you don't.

Josh Czupryk (24:52.027)
I was going to use a Tinder reference where I'm like, all of my friends who share and I'm like, God, that sounds like LinkedIn, know, no, like, block, block, swipe whichever way you're supposed to swipe to get them to go away. But I do.

Holly Owens (24:59.502)
Yeah

Holly Owens (25:05.907)
left. That's where my fiance and I met. I swiped right and I was like right is good left is bad.

Josh Czupryk (25:11.621)
Okay, so it's right, okay. Okay.

Don't do left, right? Like people, people don't do things that are gonna make a recruiter or a hiring manager go left, right? And if you say like, review my resume, I'm your next person, I like see this. And again, people are meaning to be well-intentioned and people don't think about this like you, me or Chelsea do where we're thinking about it every day. And so when you jump into the hiring market, like please just take our advice, right? Humility and value will take you further.

Holly Owens (25:21.646)
Yes.

Holly Owens (25:36.577)
Yep.

Josh Czupryk (25:43.655)
than trying to jump the line or, you know, like, and I promise I'll leave with this. You've mentioned thousands of applicants. There are 100%. I work with clients that truly get thousands of applicants. It happens, right? I'm also working with clients on how do you...

post your role in a way that it gets in front of your niche audience, right? Like maybe you're on Chelsea, maybe you're on me.

Holly Owens (26:10.536)
Yes, there's another side of this.

Josh Czupryk (26:13.875)
Because I've run a few searches where as an experiment, I just put up an ad on LinkedIn and I got flooded with applicants, but they were five to 10 % were actually certified for the role that we were posting. So was a principal role, right? And probably 50 % Holly didn't have experience at all in K-12, right? And they were looking for a job. And because there was the quick apply, we don't need quick apply.

Holly Owens (26:29.038)
Yeah.

Holly Owens (26:39.32)
Yeah.

They didn't.

Josh Czupryk (26:42.971)
So I've been advising people, especially who are hiring for remote roles, don't do quick apply, ask three to four written questions, make the transaction cost higher so that way you have a higher likelihood of getting people who can demonstrate they have the skills as opposed to people who are just jumping in.

Holly Owens (27:00.11)
Yeah, oh god, that's great advice for the people who are posting the jobs too. So you've given the advice for people who are applying to the jobs and now people who are posting the jobs. I think once it, you know, the reason I jumped into this stuff is because it feels like a game to me. And since we grew up in the 80s and the 90s with Mario and all that different stuff, it feels like I'm trying to figure out the right formula here. And I think people all too often, if they run into a block, they just stop.

Josh Czupryk (27:13.255)
Mmm.

Holly Owens (27:25.024)
or there's some kind of excuse there as to why they're not gonna push forward. So I think finding the right formula is something I like to help people do and I think that's what you like to do as well. So that's refreshing to tell, and especially like the job postings, I love it when they list what is the interview process like. Tell me the steps. So I feel like I'm not gonna be in six rounds of interviews this happened to me.

Josh Czupryk (27:44.369)
Yeah.

Holly Owens (27:50.7)
They had me on the hook as a second person and they're stringing me along and they make me do a project and then they tell me I'm not the person.

Josh Czupryk (27:57.383)
Well, and so I actually have shared that in, know, spoiler alert, if you follow me on LinkedIn, you know, I'm very openly autistic, right? Like, and I'm very open about it. But when I do a search and when I do a phone screen, I say, hey, welcome to the second round of the interview process, right? You're in the phone screen. The first five minutes, we're going to talk about the logistics of the search. I'm going to give you all of the dates of each of the rounds. I'm going to tell you when you're going to hear by.

Holly Owens (28:05.174)
Right.

Holly Owens (28:22.85)
I love that.

Josh Czupryk (28:25.907)
Now I will say I don't give feedback because quite frankly, my insurance company said don't give feedback. Right. I was like, what I have started doing is if people are finalists, I'll do a coffee chat exactly to what you said where I'm like, the client, what was somebody else on this one? But if you want to chat about what else is out there, et cetera, right. I'll chat with you. I'm totally optional, right. Not forced, but to your point people, I feel like shine so much better.

Holly Owens (28:32.472)
Yeah.

Holly Owens (28:48.354)
Yeah.

Josh Czupryk (28:55.729)
when you take the cognitive load, and again, going back to instructional design and theory, but if I can take the cognitive load off at the beginning of an interview to tell you exactly when you're gonna hear and how many rounds there are gonna be, you can then shine and tell me why you're the right fit and you can go through the scenarios.

Holly Owens (29:08.461)
Yep.

Holly Owens (29:14.03)
feel like this whole episode was just advice. I don't know if we need to do the, well actually, you're an entrepreneur. So there's people, like we talk a lot about the norm of transitioning teachers going into L &D, going into instructional design, all that stuff, but what if somebody wants to start their own business? What if somebody wants to do what you're doing? As our three pieces of advice, give people who are like, I wanna do my own thing. What should they do?

Josh Czupryk (29:16.371)
you

you

Josh Czupryk (29:37.553)
Yeah. Number one, I will say that I am really lucky that I have a partner who has a salary because it is really steady. And so if you're going to jump into entrepreneurial life, you got to understand the ebbs and flows of cash flow because you'll run into a lot of cash and then you'll run into no cash. It's not salary. You're not getting the same amount predictably every two weeks or twice a month. OK, so that's number one is if you can wrap your brain around cash flow, you're already winning.

Number two, understanding the logistics of becoming an entrepreneur. So that means understanding, getting a 501c3, not a 501c3, getting a 1099, know, sole proprietorship LLC set up. So you're able to get paid, getting a business banking account. Don't take checks in your personal, so that way if you ever get audited or sued, it goes to the bank account.

You don't have to get it, but errors and omissions, insurance. use the Hartford for that, like very easy. Now they're going to give you rules, like what I mentioned earlier of like what you, you may like at the bottom of my, like where you can add rules, I had to put a disclaimer, like this does not guarantee you will hire somebody. And I was like, really? And the insurance company was like, yes. Really? You need to get an invoicing system.

Holly Owens (30:39.56)
Yeah. Yeah, yeah, yeah. Yeah, I've seen those.

Holly Owens (30:52.61)
Yes, yes, yes.

Josh Czupryk (30:58.129)
But they're all out there. I'm super open about it. And I'll try to do a post on LinkedIn when the episode comes out.

Holly Owens (31:03.532)
I think you should, I think that'd be very helpful. I was checking off the list in my head that I've done all these things, but I may have been missing something, who knows? It's so convoluted being a small business owner and trying to find the resources of where to do stuff and what's... Anyways, that's a conversation obviously for another day, but I appreciate that advice. Just keep it simple, make sure you're following the rules, setting up the stuff that you need in order to be successful.

Josh Czupryk (31:10.033)
Yeah.

Holly Owens (31:27.958)
I'm in your business and you know what teachers you can totally do it. You can totally do it. There's no like I think sometimes teachers are like I just I can only be a teacher. That's all I know how to do. Not true. There's other episodes that talk about that.

Josh Czupryk (31:40.251)
I will tell you, the last advice I'll give a teacher is when I think about a senior leadership role, they would be a wonderful chief academic officer in a charter network or district. I'm not saying they wouldn't. They would also be such a good chief of staff because so many chief of staff roles are GSD roles, which is what we say, get stuff done. And there's another S word you can use, but like teachers just get stuff done.

Holly Owens (31:51.854)
Yes. Yes.

Holly Owens (32:03.576)
Mm-hmm. Yeah.

Josh Czupryk (32:08.423)
They think about what is the most efficient, lowest transaction cost, highest value way that I can just get to this goal because that's what they do in the classroom. And if you want to leave being able to be again, exactly as you mentioned, a customer success person and instructional design person and operations person. When you can speak K-12, you have opened up for that nonprofit or that ed tech company to have an in the market with the customers because you speak the language. So have confidence.

Holly Owens (32:35.586)
Yeah, I love it. We're gonna end there. There's gonna be everything in the show notes because this has honestly been a very enlightening, engaging episode and talking with you is just reaffirming some of the things that we consistently share out on LinkedIn World. And we're not just, we're not BSing here. We're really sharing real advice. So Josh, thank you so much for coming on the show and sharing that and everything to find Josh, K to 12 job blast.

Josh Czupryk (32:39.635)
Thanks for watching.

Thanks.

Josh Czupryk (33:02.643)
Thank you.

Holly Owens (33:02.766)
All the different things are all going to be in the show notes. So please go there. Please connect with Josh on LinkedIn. Can't thank you enough, friend, for coming on the show and chatting with me.

Josh Czupryk (33:10.823)
Absolutely Holly, thanks for the invite.

 

Josh Czupryk Profile Photo

Josh Czupryk

Founder, Josh's K12 Jobs Blast

Josh Czupryk is the Founder of Josh’s K12 Jobs Blast where he helps transitioning teachers and transitioning leaders find meaningful work each and every day.

In 2022, seeing a need to better connect talented K12 individuals with opportunities that would keep them in the field, Josh launched Josh’s K12 Jobs Blast. The jobs blast now serves over 12,000+ subscribers and indexes 145+ job sites weekly.

The mission of the job’s blast is to provide high-quality educational leadership opportunities for talented professionals to find their next, right job.

He has served in public schools, public charter schools, and training and laboratory schools as a Chief Academic & Operations Officer, a Chief Strategy & Operations Officer, a Chief of Staff, a Managing Director of Academics, a Teacher Development Coach, a Program Director, and as a teacher. He brings expertise in talent acquisition, talent retention, academic strategy, data systems development and analysis, operations, and talent management to the table as a thought partner and strategist. Josh led the academics and operations team for the state of Tennessee’s highest performing school system in terms of proficiency and growth (49 percent diverse student body, no academic requirement for entry, and students from all 36 zip codes in Shelby County) for three years.

The son of two proud public school teachers, each with 40+ years of service in the classroom, Josh earned a Master’s in Educational Leadership in 2018 from the Broad Center (now the Broad Center at Yale School of Management)… Read More