Episode 63: Jason Yingling

Hallway Chats

Introducing Jason Yingling

Jason Yingling builds WordPress sites focused on results, he’s digging deeply into Gutenberg and shares what he learns on his blog at Jasonyingling.me. When not working with WordPress, Jason likes reading Elmo books to his one-year-old, he says, not to himself.

Show Notes

Website | Jason Yingling
Website | Red 8 Interactive
Twitter | @jason_yingling

Episode Transcript

Tara: This is Hallway Chats, where we meet people who use WordPress.

Liam: We ask questions, and our guests share their stories, ideas and perspectives. And now the conversation begins. This is Episode 63. Welcome to Hallway Chats. I’m Liam Dempsey.

Tara: And I’m Tara Claeys. Today, we’re joined by Jason Yingling. Jason builds WordPress sites focused on results, he’s digging deeply into Gutenberg and shares what he learns on his blog at Jasonyingling.me. When not working with WordPress, Jason likes reading Elmo books to his one-year-old, he says, not to himself. Although, who knows. Maybe sometimes. Right, Jason? Hi, welcome, Jason.

Jason: Hi, thanks for having me.

Liam: Hey, Jason. Thanks for joining us out here. Delightful to get to spend some time with you. Can you tell us a little bit more about yourself, please?

Jason: Sure. As you know in my intro, I have a one-year-old, I’m a new dad. So I’ve got her running around. That’s a big part of my time these days. But when I’m not attempting to race her, I do WordPress development for a company called Red8 Interactive. I’m based out of St. Louis, Missouri but we actually work remotely now. We build custom WordPress sites, a lot of advanced custom field kind of focused stuff. And that’s kind of been our big thing. I think about when I started there about six years ago, we did a big shift to WordPress-only development. Because we were kind of mixing all around then, just to kind of niche down. It has been really good for us over that. It kind of helped me grow through WordPress, I’m able to go to WordCamp and get involved with the community a lot more. Now I’ve kind of expanded that into helping plan the WordCamp here in St. Louis, which will be going into WordCamp US next year. So that will be a big thing. Then doing some local meetups and then kind of doing some of my own theme and plugin development on the side just to keep moving.

Liam: That’s wonderful. I have two points I want to talk to you about. As a WordCamp Philly organizer and one of the organizers on one of the first US teams when WordCamp US was in Philly, be careful what you wish for. [laughter] A city WordCamp is one thing. No, I’m kidding. I’m being a little bit silly about that. The second thing I wanted to ask you about is when we–

Tara: No, you’re not.

Liam: No, I’m really not. [laughter] When the agency that you’re with was looking to limit the number of content management systems that it uses for building sites, what’s your involvement in that? Were you on the research team, were you on the development team, were you pro-WordPress or was that a decision that just came out? Maybe you can just talk about this because that’s really interesting. I’d be interested to hear how that decision kind of came about?

Jason: It’s been a while now but I’ve only been there probably six months or so, I think, when we kind of decided we were making that change. At that point, I was a junior developer there. There was a couple of senior developers that kind of led the charge. One was actually one of the original organizers. He organized some of the early WordCamps St. Louis so I’m sure that was a big driving force as far as his experience with it. And then just being– I think at that point, we were five developers and a couple of project managers. I was kind of with a small team trying to narrow our focus because we would have a build that’s like a Javascript Geolocation thing going on at one point. One thing that we did was a bunch of these kind of Amazon apps inside, like Amazon web stores. That was its whole own set of testing and all that kind of stuff. So just kind of narrowing our focus so we can just get really good and kind of consolidate our process so we can automate things, repeat things. That was the overall goal to focus down.

Tara: Jason, what’s your background? How did you get involved in WordPress and coding to begin with? You’ve been with this agency for a good bit, it sounds like? What’s your background?

Jason: Yeah, it’s actually not development really at all. I’ve always kind of been interested in web development, playing around with HTML and Flash back in the day, in high school. Just kind of teaching myself on the side, taking little classes here and there. What I actually went to college for was marketing, and then I also did a little bit of programming. My college had electronic arts that did a little bit of video production and audio, and a tiny bit of multimedia web stuff. I’ve just kind of always done that. Then I hung around and got my MBA, then when I finally started looking for a job, the first stuff I was finding was development stuff. I was like, “Alright, we’ll give it a shot.” I got hired pretty quick there and I’ve been at the same company now for a while. With the shift to WordPress I got– having the first senior dev kind of lead me in into WordPress and getting involved with WordCamps and stuff kind of got me more involved with that community. I always really liked how easy it is to create things. Just anybody can kind of go in and get something started. It’s one of the big things I like about the kind of open-source WordPress community.

Tara: Yeah. It’s interesting to me that you have an MBA, and a marketing background as well. I find it really helpful in what we do because websites are basically a marketing device, that’s really what they are at their core. So I find it very helpful to have that background. And MBA is a whole another level. I don’t know if I’ve met any MBAs who are doing WordPress development. Has that served you well?

Jason: Yeah, moreso now. Over the last three or so years, I’m now the director of development at our company so I’m kind of more in management leadership role. I still do a bit of hands-on development a lot of the time because we are so small. I think at this point, now, we’re actually three developers and one BM, we’ve kind of paired down even a little bit. Yeah, it’s kind of kicked in a little bit more now. And then as far as the marketing kind of stuff that I’ve done has been helpful just on some of my side-project stuff I like to work on. Any of that kind of stuff.

Tara: Are you one of the owners of the company that you work for?

Jason: No, I’m not.

Tara: Okay. Have you ever owned your own business or is that something–?

Jason: Kind of, I guess. I mean, I have a ton of different side-projects, nothing official really. I’ve got a site I put some themes up on just because I’ve kind of built up a few practice ones and stuff like that. But I don’t have anything really officially of my own business. It is something I’d be interested in doing down the road, I think, for sure, because I do kind of have that business background.

Tara: Right. It sounds like you’re applying that in a good capacity where you are right now, though, and not having the stress of having it be your own business and making payroll and all of those things that come along with them.

Jason: Right, those ones don’t sound as fun as creating the stuff. That’s what I’m more into, really.

Tara: And working remotely, how’s that? You have a daughter, as you said, who’s one, and you work from your house with her around, or is she out of the house?

Jason: Yeah. Let’s see. I think in October, shortly after she was born, so I guess last October, we went fully remote. Before that, we were working out of– it’s a building called Opio Startups here in St. Louis. It’s kind of like a tech incubator where people can rent office space essentially for small companies. We actually had kind of a larger office there and we were only using half of it, which is why we kind of ended up going fully remote. Actually, all of our developers are in St. Louis, but our CEO is based in San Francisco area. Yes, it’s been nice working remote. My daughter was about five or six months old when we went fully remotes so it’s been nice to be around whenever she’s there. My five was a teacher but she needed to go back right away so she’s been home, too. She’s able to kind of watch her if I ever have to do calls or anything like that. But it is nice to just be able to kind of run out and be able to play with her for 15 minutes to take a break. No commute is nice as well. That saves some time.

Tara: Yeah, for sure. I think if you can do this, especially when they’re little, it’s a great treat to have that opportunity. That’s great that you can do that. And your wife’s a teacher so she’s home during the summer and you said she’s taking some time off so the two of you cohabitating all day long with the little one. You can trade-off queue I imagine, yeah?

Jason: Yeah, for sure. My daughter’s a little more active now, she’s been getting better at walking in the last couple of months so she’ll kind of just come stumbling into the office a little bit. She’s apparently figured outdoor closing today so I heard her coming and then turned around, and she was closing my wife out of the room. [laughter] But she can’t open them yet, so that’s good.

Liam: That’s too funny.

Jason: Working remotely, it has its own– as far as doing the work and working with the other developers as a team, it does have its own issues to try to figure out. One thing that was nice when we had our kind of office space because we could just kind of lean over each other’s shoulders and be like, “Hey, what’s up with this issue?” Or kind of see if someone was deep into something and not just ping him to take him out of it. Yeah, those are some of the things that we’ve kind of been working out the kinks of still, as we’ve been little under a year fully remote now.

Tara: Yeah. I work for myself so I don’t collaborate that often but I always think about maybe just turning Zoom on with somebody else working simultaneously so you can sort of simulate that office environment and have some chit-chat. But once you start doing it for a long time, I think you lose the habit of even interacting with people. I mean, many years ago I did that but you sort of lose the habit of it.

Jason: One of the nice things– since I helped host a WordPress meetup here and I actually do it in the old Opio building where we had space before so they actually gave me a membership for doing that and let me come in and kind of hang out if I ever need to kind of get out around and actually work with other people, kind of deal.

Tara: Yeah, that’s a good opportunity. That’s great. I’m going to ask you a question we love to ask everyone, and we think about it often ourselves a lot, too. I want to ask you about your definition of success. It sounds like you are in a good place and you’ve got your family growing, and your job has transitioned a bit to allow you to have more flexibility. How would you define success and where on that journey, if it is a journey for you, where di you find yourself in that journey with that path of success?

Jason: I’m not the best at putting it into words, I guess, but I kind of define success as just kind of constant motion forward almost. Even if a project may not be like a financial success or something like that, there’s plenty along the way that can kind of be mined from as small successes and kind of applied to future learnings. I’ve always considered, as long as things are kind of moving forward and kind of learning from the experiences that that’s successful. As far as where I’m on my journey, I have trouble defining what successful endpoint would be really, so it’s hard to put a play on it but things have been moving along pretty well. Obviously, I still want to keep growing both career and family-wise and everything, so it is somewhere in the middle, I’d say, in the journey. But it’s definitely going in the right direction.

Tara: Yeah. Maybe there’s not an endpoint but it’s sort of like following it along or riding alongside it. Cool.

Liam: Yeah, I like that. It is a journey. And maybe success almost is being mindful of the improvement and the challenges overcome. Jason, as you noted, sometimes those improvements and those challenges overcome happen really quickly. Career goes on leaps and bounds. The arrival of your daughter, okay, it took nine months to get there, but once she’s there, that’s a huge change. And other times, it’s more gradual. But just being mindful of the effort and the change. I like that definition, thanks for sharing that. If that is your definition– and I’m not questioning, that’s just a transition comment, I guess. Given your definition, what’s the single most important thing that you do every day to keep moving forward?

Jason: I really just kind of keep plugging away at it, just kind of keep learning, trying to find the little successes in the different things. Some days, obviously, I get a lot more done than others towards any one goal. It’s just kind of, keep plugging away, just as long as we’re making improvements. As far as a company, as long as we’re making improvements. If we’re not hitting the deadline, what caused it, where can we fix that up later? Stuff like that, just to kind of keep improving.

Tara: What’s your favorite thing to do every day?

Jason: You know. I always have trouble deciding on things like these. As far as the work standpoint, I like the more creative aspects. If I’m doing coding, kind of solving complex problems and trying to create a simple user-friendly solution to complex problems and just kind of organizing stuff from that aspect. As far as personal life, things have definitely changed quite a bit now as spending time with my daughter and being able to kind of go around and play with her, whereas a couple of years ago, it might have been something a little different.

Liam: Let me ask you about the work one first, if I can. Your favorite things at work, solving creative problems. Now that you’re the director of development and coding less and working ‘more’, managing more using your business degree. When you get to be creative, are you writing the code that solves the problem or are you setting up the workflow, and the conditionals, and making sure that the fields collective will flow together and can go into this API or that? Where do you get to be creative and how does that play out in terms of sitting down and getting work done?

Jason: It is a little of both. It’s probably kind of a split, since we are a small development team. I still do a good chunk of kind of development. But obviously, I try to offload some of the stuff, even some of the more complex stuff, if I can, which isn’t easy always. Kind of the new challenge that that’s open for is how do I get better at kind of setting the requirements and expectations for a project at the startup rather than being the one that’s actually doing it, where all those can kind of be in my head and I kind of know since I deal with our clients a lot more than our developers, then I have more information and getting that information over to the developer that’s working on it in an effective way and making sure that they’re set up to go through everything. That’s definitely one thing I’ve been working on a lot lately, too, is kind of managing all of our different developers’ workload. Since now, I think we host about 60 of the sites that we built, so we do some hosting of sites we build through WordPress engine. So we do a lot of maintenance work from those as well. Kind of managing new project custom-built and fitting in time with our limited hands-on-deck to be able to kind of squeeze all that in and hit deadlines and stuff like that has been a big kind of challenge to work on.

Tara: Yeah. And then if you’re also now responsible for business development, I would think that also is a challenge, trying to spread yourself in very different directions. Do you have a preference? Do you enjoy having that diversity of tasks or if you could choose one thing to focus on, what would it be?

Jason: You know, I like the ability to kind of mix around a little bit, but it definitely is hard. And really, my position is more focused on kind of leading development on projects, I don’t do a lot of business development or sales-type aspects. I do more kind of producer-based setup where I’m working with clients to get the requirements, convert them into estimates and things like that. It’s a little bit trying to get– I do work with our CEO that does most of our sales a lot and try to make sure that he’s getting proper requirements from the client, and then those are getting mapped back to our estimate and then to our developers in a way that they can be handled as if they won. I do find it now that I’ve got a lot more going on, it is kind of hard to get focused on some of the more complex development things and be able to just kind of block out that time when it’s going to take four or five hours to build something. It’s a little harder to come across those things. I think I probably enjoy that time a little bit more just because I can kind of get locked in and focused on something. I know the other aspects are very important as well.

Tara: Yeah. Sorry, I think you said business development earlier and I think we have the term development is– I guess I’m just realizing how it has multiple meanings.

Jason: My title is director of development but I’ve noticed that that is kind of more of a business development thing usually. Web development is the term behind it.

Liam: I heard it as web development. [laughs]

Tara: See. That’s because I have a marketing background, that’s where it comes in. Sorry about that.

Jason: No problem.

Tara: It sounds like you’re pretty involved in the WordPress community and we also like to hear a little bit about that. We mentioned at the beginning that you’re diving into Gutenberg a little bit and maybe giving back to the community with some things that you’re learning there and being involved in WordCamps. What’s your favorite thing to do community-wise in WordPress?

Jason: I really enjoy a lot of different aspects. I’ve done a lot of WordCamp planning here in St. Louis. That’s always been interesting. I’ve been pretty involved with the website portion of it, going from the development background. And then we’ll be doing the big kickup for the WordCamp US coming next year. I’ve been somewhat involved with this year’s US. They kind of brought us in, a few people, after St. Louis was announced to kind of just see how it’s done as far as the big one. And I’ve definitely seen that it’s a lot more than just the city camp.

Tara: Have you attended WordCamp US before?

Jason: No, not an official WordCamp US one. I went to, I think it was, WordCamp San Francisco still, which was kind of the defacto US for a while. I think that was 2013 or ’14 maybe, that I went to one. That was probably the biggest one I’ve been to. Aside from that, I’ve just been to the ones at St. Louis and Kansas City, around this area for the most part. But yeah, that’s definitely one of my goals to get to a few more and apply to speak at some. I enjoyed giving talks at WordCamps. Public speaking isn’t really my forte, but kind of just going out there has forced me to do it. That was actually a big one behind the Gutenberg stuff. Because we were doing WordCamp US and I noticed no one had really submitted Gutenberg talk so I was like, “Alright, well, I’ll send one.” And then that one obviously got chosen so I was like, “Okay, now I have to learn this.” It was kind of a big focus on– how I kind of approached that was to just really go in topic by topic and just kind of learn it and then do a post about it on my blog, and then just kind of share to kind of basically put it into my words so it, one, helps me remember and be able to explain it so I actually can tell that I know it. That’s been definitely helpful, getting started with it.

Tara: That’s a brave undertaking certainly signing up to do a talk, I think, is one of the best ways to learn something. But Gutenberg seems like kind of a moving target a little bit. It’s changing so much. By the time you actually give the talk, it might be quite different than what you’re learning about it right now.

Jason: Yeah, and that’s true because I didn’t notice I was finishing up my slides the night before as I’m usual to do. And I happen to see that something had– there was a new update that came out two days before, and they deprecated a portion of it. I was like, “Oh, no.” So I had to stay up and–

Liam: What’s that line?

Jason: Yeah, exactly. I was like, “Oh, now I’ve got to figure this out and see exactly how it works so it makes sense.” I was like, “Wing it!” Yeah. I left it in as a strike-through and like, “Yeah, this was supposed to be in here yesterday but today, it’s over here. That’s just where the Gutenberg development is at this point.” That was a few months ago. It’s come a long way since then even, too.

Liam: Yeah, it continues to– Jason, I’m going to ask you another one of our signature questions, if I can. What is the single most valuable piece of advice that you have ever received and implemented in your life? It can be personal advice, professional advice, maybe a mix of both, received and implemented.

Jason: I’d say it’s to never stop learning really. Even getting done with college and everything was kind of like, “Oh, hey. I’m done with books and all that and I can stop.” Since I left college, I probably read more, learned more things, especially being in– getting involved into WordPress with just a ton of different stuff to learn that wasn’t really what my background was, as far as development, learning development techniques and all that kind of stuff. But yeah, really just to not stop learning. Kind of what I try to do now is I’ve been shooting to finish 52 books this year and that’s a lot through Audible, audio books and stuff is a big thing I’ve kind of hooked onto.

Liam: Does that include the Elmo books because I feel like– [laughter]

Jason: No. I haven’t counted those ones but that’s a good idea to up my numbers, I forgot about that. I’m kind of behind where I was last year.

Liam: I think you should. A book’s a book.

Tara: Good one, Liam.

Jason: Exactly. That’s a good point. I’ve got to be way over then.

Tara: Maybe Elmo can write a book about WordPress.

Jason: Yeah, that’d be good.

Liam: There’s a top for you. Elmo Me WordPress, right?

Tara: I think Rebecca Gill does a lot of talks with Sesame Street characters and stuff like that. That’s her backdrop for her slides maybe, you can do it with Elmo, Gutenberg with Elmo.

Jason: I have to work on my Elmo voice.

Liam: Jason, I have a question that popped into my head in this conversation and it’s really out of left field. I’ll kind of string the question out a little bit to give you some time to think about it. Because you’ve talked about your definition of success as kind of keep moving forward, keep making progress. It’s not so much the pace, it’s the fact that there’s some sort of forward movement. And then you shared with us most important piece of advice or most valuable is all about continuing to learn. And you explained that your favorite thing to do at work is to be given time to address complex challenges and try to come up with a valuable professional response in terms of developing user experience that works. I wonder now that your daughter’s coming up– you said she was born in October so she’s a year and a half or coming up on a year?

Jason: She was born in June so she’s a little over a year.

Liam: And so she’s clearly learning. You just said earlier that she’s figured out how to close the door. As you watch her, as you play with her, as you be her dad and help her learn and grow. What are you, if anything, seeing or witnessing about her approach to learning that inspires you to maybe think about the way that you look at learning? Whole idea that it’s all new, they’ve never seen a door before, they’ve never twisted it before. And the things that you, and I, and Tara do as routine, it’s so new to children of that age. Everything is. I just wonder, because I’m not a developer, my brain doesn’t do problem-solving in that way. I don’t, not enjoy it but it’s not, show me a big problem and I’m good for days. I don’t do that, I’m more of a marketing and design kind of thing. I just wonder about that. Are you seeing things there that offer insight or value to you in some ways, aside from the joy of watching your daughter learn?

Jason: Yeah, I hadn’t really thought of that but just kind of top of my head what kind of pops up is that really she’s not really afraid to try things, even though she’s going to screw it up. It’s not going to work out, whatever she’s attempting to do. Just kind of like, “Oh–” With the door closing thing, she can close the door but she doesn’t know quite how to open it. But even today, she was trying to jam her fingers in the crack, and then she was me get the knob, and then a couple tries later, she was trying to reach up and see if she can get on her tiptoes to reach the knob. Luckily, she can’t quite grip it to spin it so she’s not able to just full run in the house yet. But yeah, I think kind of that experimentation failing and trying, and learning from that failure and kind of building on that is definitely something I see watching her learn. That’s something that I like to try to implement myself, too. With the Gutenberg stuff, really the first time– we have a monthly meetup I host and we didn’t have a topic so I was like, “I’ve learned a little bit of Gutenberg. Let me try doing a talk on it.” And it didn’t go well at all because I was like, “Oh, man. I don’t know the technical stuff of this quite enough to really explain.” So I was kind of stumbling over. But then by the time the WordCamp presentation one came around, I had put a lot more effort into learning all of the different things, kind of being able to build on that.

Tara: I think we have another possible talk topic here, we’re coming up with all these great ideas. I love the relationship between the way a child learns and how we implement that in learning as developers or learning new things is not being afraid to try it and fail. Very good point.

Liam: And to learn from others just by observing, right? It sounds like you grab the door knob and twist, but there she saws that, “Oh, now I know.”

Tara: Talk topic brewing. Very good. Alright. Jason, on that very productive note, I would like to thank you for joining us today. It’s really been a pleasure meeting you and hearing more about you and what you do and your family. Would you share with us and everyone else where we can find you online?

Jason: Yeah. And thanks for having me for sure. You can find me online. My website is Jasonyingling.me and then my Twitter is @jason_yingling. Yingling sounds like the beer but it is spelled differently.

Tara: Great, thank you.

Liam: Jason, it’s been an absolute pleasure. Thanks for joining us here today in the hallway.

Jason: Thanks for having me.

Tara: Thank you very much.

Liam: Bye-bye.

Tara: Bye.

Jason: Bye.

Tara: If you like what we’re doing here – meeting new people in our WordPress community – we invite you to tell others about it. We’re on iTunes and at hallwaychats-staging.ulpgsyz6-liquidwebsites.com.

Liam: Better yet, ask your WordPress friends and colleagues to join us on the show. Encourage them to complete the “Be on the show” form on our site, to tell us about themselves.

Tara: If you like what we’re doing here – meeting new people in our WordPress community – we invite you to tell others about it. We’re on iTunes and at hallwaychats-staging.ulpgsyz6-liquidwebsites.com.

Liam: Better yet, ask your WordPress friends and colleagues to join us on the show. Encourage them to complete the “Be on the show” form on our site, to tell us about themselves.