taylor desseyn

guidance counselor 2.0 · episode 479

aaron presley on leaving nike, freelancing & finding purpose beyond code

aug 29, 2025 · 19 min · with aaron presley · hosted by taylor desseyn

key takeaways

  • before going independent, ensure you can budget and live with lower income for an extended period
  • find a specific niche you're passionate about rather than chasing unicorn startups or generic opportunities
  • networking is a skill and muscle that gets easier over time even when it feels uncomfortable
  • contract-to-hire lets you evaluate real fit better than traditional interviews ever could
  • redefine success as happiness and bills paid instead of startup valuations or titles

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about this episode

how leaving a big tech company to freelance requires budgeting, niche focus, networking skills, and redefining success beyond money

full transcript

auto-generated from the audio, so expect a few typos. the audio is the source of truth.

I've never in my life been on a podcast. So for real? Yeah. Oh, heck, yeah, dude. Heck yeah. All right, so for those of you watching, welcome, I'm just going to call this the guidance counselor 2.0 podcast live at DevWorld. Not have a podcast that been doing it for five years now, virtually, where I interview people in the engineering space. I call it like the soft skills of the engineering, the soft skills podcast of the engineering world. So I'm here with Aaron, fellow American. It's good to see you, man. Nice to see you. You're glad to be here. Exactly. So basically, the whole thesis of my podcast, I was telling you before we started recording is around career job stuff, right?

We'd love to know just a quick background about you just to set the stage and we'll dive into some questions. But if you want to go ahead. Sure, yeah. Been a computer programmer since I found buttons as a little kid. And that had been pretty fascinated with it. It just so happened to grow up in a world where it became a good career to be kind of a computer nerd. Been programming for a long time, got an internship. Out of college and never really looked back. Yeah, I eventually got hired on at Nike where I became a globalization expert. So a localization architect is kind of the phrase that's used.

So at Nike was able to be on the team that sort of created all the logistics of all the translations throughout their app tens of thousands of words a day translated. It's crazy. Yeah, so it became a localization expert there, which was super fun. And so now I've kind of taken that on the road, so to speak. And I'm an independent consultant, helping companies like understand the coding infrastructure of translating their sites and making some human-centered code and adapting to different regions and stuff like that. So that's what I do now. That's all. That's all. That's cool. So I am curious, people that will watch this in the future.

They're probably like, man, you left Nike. Yeah. And now you're doing your own thing. Yeah, I make way less money. We'll talk about that, right? Because I think a lot of times I always talk about, you really got to pursue stuff you want to do. Yeah. And sometimes the money's there. Sometimes the money's not. Talk about that step to step out of Nike. What prompted you to do that? Yeah, I think the prompt was I became really passionate about the topic. So guy in the tech industry, I accidentally landed in this topic of localization, globalization. And that was really the first time I came across a scenario where like, oh, no, my job is to think about the human first.

And so I became really fascinated, not only from that perspective, but then linguistics, like I find really fascinating. And then beyond all that is the technical side, like the Unicode consortium, like all how all that is architected. All of us just being able to text emojis in different characters, like the way that actually happens is insanely fascinating to me. And so I think what prompted it is just a passion to help other companies figure out what I did at Nike. Not a lot of engineers have the ability to work in a code base or hundreds of code bases that support like 25 languages, 20 regions.

And so that and also selfishly, I want to be independent. Like I loved Nike, some of my best friends are from there still. But there's always something about wanting to strike out on your own. And if you niche into a topic, then might as well try and make something of it. And so I found some really good partners. I'm here with localized, who's a translation vendor or management system. And so yeah, I found some really good people in the industry to work with. And it's all I love. I love that. I think, of course, I talked about this is career stuff, but a little pivoting even when I told you before, he started.

But I am curious, going on on your own, what are some things people should consider before that? I do feel like lately with how the market's been, when I used to start recruiting 2011, people are like, I only want a full-time job. I'm never contracting. Now it's now people are way more open to contracting and freelancing than they've ever been. Because I really feel like the, in my opinion, the trust was a little broken from the company to employee around full-time over the last few years with how many layoffs and the layoffs that continue to happen. So what are just some words of encouragement of some things people just keep in mind before going out in their own?

Yeah, I mean, how are you with budgeting? Yeah, I mean, that would kind of be the number one thing. Like you have your money situated, you prepared to not really make a ton of money for a while. I think also it's easier to be more interested in freelancing contracting when companies aren't hiring as much. Sure. So that's a lot easier. I think the days of the easy money in the tech industry is kind of over. And so that's part of it. I would also personally, I kind of think it's okay to think smaller. Like everyone wants to make the unicorn start-up. They want to make all this stuff.

But like, hey, look around your neighborhood, see people have small businesses all the time. The power washing company down the street is able to pay their bills with their small business. And so we in the tech side have access to technology that can like, yes, it can scale to an insane amount. And that means your local area probably has a need in a small niche that you can help with, like, pay your bills. How about start there? And then maybe sell for a billion dollars. But I think that's kind of the advice I talk to people about. I think another thing too, and I want to bring up and kind of softball this to you is obviously, I'm sure, when you go out on your own, you have to have a network.

And you're at a conference now. Yeah. You talk about the power of networking and just showing up to these things. I mean, it's a new skill for me, honestly. It's, you know, I started as a, obviously, a programmer. I eventually became an educator where I talked to people about localization. And I never thought I would be someone who volunteered to go up and speak in front of people for any reason. And so I'm still learning the power of networking, like, even agreeing to do this as well out of my comfort zone, never in my life been on a podcast. So I'm... You're crushing about that.

I'm relying on people like you to tell me that the networking thing is worth it. But yeah, man, signing up for like going to dinner or all these events as well out of my comfort zone and not something I'm great at, honestly. Yeah. But in the, you know, since I've been independent only in the less than a year now, I can see that there's like, it's a bit of a flywheel that it's really hard to get started. But once you're going, it becomes a little bit easier. And it's still like, you have to, it's hard to make the decision every time. I'm like, okay, yes, I'm an Amsterdam.

I have like a crazy, you know, layover hangover pretty much. Yeah. And like, yes, I'm still gonna choose to be social. Like, that's not easy. And I don't always choose to network. Sure. But I am starting to like, over time, see the benefit of that keeping that flywheel to a muscle. It's a muscle. Yeah, it's a muscle. It's a muscle. For Dartside, I'll be mad at you and, you know, you. So talk about, I want to go back to one thing you mentioned. And I think it's going super niche, right? I feel like, correct me if I'm wrong, but I feel like your specialty is relatively niche.

Yeah, hopefully not too niche. Right. But like, because I do feel like people would say, I'm gonna build an ex uniform. It's like, I think you can be very specific right now and actually carve out a really good lane for yourself. Do you agree? Totally, you're a, yeah, I think that's, I hope that's the next way that technology is removing the unicorns, removing upset industries. Like, how about make something for your local community and have them pay you $5 a month to do it? And like, that would probably pay your electric bills. And like, have that mindset in the small business mindset. I would love a world of like, mom and pop tech companies.

Yeah. And so that's what I personally hope to see happen kind of in the next wave of tech. When it comes to, when it comes to kind of growing your career, right? I mean, you, you worked at a big company. What is kind of been maybe your secret sauce, right? Like, I feel like you just don't get to where you're at in your career without being really good. Maybe that's a interpersonal stuff, being good from a business perspective. What are some things you feel like you do really well? Think what a, yeah, that's all I said. I know it's so supernatural to me. I think just the ability to realize that being able to code, especially moving forward isn't the skill.

Like, it's going to be easier to write code for everyone. And so what do you have left when you remove the ability to like write a JavaScript function and use AWS? Like, all that's going to get easier and easier and easier. And that's no longer your edge. So what is your edge? Like, do you care about people? Do you like want to find a niche? Do you want to network? Like you do. I think there's a lot of directions you could go. Yeah. And I think if developers hold on to this mindset, they're like, no, my ability to write code is what gives me an edge over the next future.

I don't personally think that's kind of the way to have a winning recipe, but more being willing to say, like, all right, this is the reality. I'm in what do my skills give me an edge to do naturally and then experiment, try things. And so I wouldn't even claim myself as a success. I'm doing the same thing. Like, I'm trying new stuff. I've been able to build up a little bit of a consultation business. But it just depends on how you define growth. And I think I stopped defining like success or growth as like building this million dollar startup or billion dollar startup and more just like, am I happy and are my bills paid and then going from there?

You know, it's funny you bring that up. My wife and I've had that conversation at Tundlately. And I think like, and I've talked about a lot too. And I've talked with a lot of people in tech who, by the way, it's really funny. There's people with VR goggles on behind you. And they're all like doing some funny. And it's just like the funniest thing ever. But like truly finding happiness in a career tech can be hard. It's because, you know, I mean, we all have our, we all have our acquaintances who are killing it, right? Like literally there are recruiters who are more money than me.

There are people who have more speaking gigs in me. There are people who have way more followers in me on social media and the recruiting talent world. But I've kind of carved out my niche. And I'm very, very happy where I'm at, right? I get to interview you and Amsterdam. I mean, like, you know, I'm very blessed. And so I don't know if you have any more thoughts on that. But I always tell people you can only make outside of fan. You can only make so much money. There's always so many titles. There's, you know, so it's like you gotta figure out what you really wanna do.

Yeah, you gotta figure out what you wanna do or just be willing to kind of like take it as it comes. Even if you don't like think ahead and say like, all right, I know I want A, B, and C. Think about the things you do know and then like take that step. So like, all right, I know I wanna be around people. That was something I learned is that, I used to think I wanted to just code in a basement and like be bothered by anyone. And then it was a really weird identity shift to learn like actually I kind of like being around people and talking to them which was new.

Say, okay, well, I have this niche. I kind of like talking to people. I love educating them about internationalization and helping companies with that stuff. I think there's like a lot of unknowns around there. So that's the step I took. And I might make a different one later who knows but kind of not being so set on what you think is should happen to the detriment of like, what would happen if you were open to it. Yeah, for me, I've kind of gone away. I used to be really big on like New Year's resolutions, right? Yeah. Like, right there are all these things. And it's like now I don't even do it because what I've realized is that like, I feel like there are seasons within seasons of your life both professionally and personally.

And there's gonna be times, I mean, a full transparency, you know, I was a traditional recruiter for a long time. Like I know I've been very open about this because of the way the economy hit in the US. I mean, I was making 40 to 50% less year over year because I was heavily commissioned based. And so like my wife and I've had a lot of this conversation like, you know, are you happy? And I moved out of traditional recruiting because I was not happy. I was, I wanted something more and that sucked and that hurt my paycheck. And now I'm on the other side of it and I'm in a very great position, thankful for torque for that.

But it's one of these things where like, I was okay from a fine, I wasn't okay, but I was also in a way, okay, and I knew it was gonna work out because I was passionate about the new thing I was doing. I wasn't always chasing the money. Talk to so many engineers, so many people that are like, I just want the bag and listen, I get, I understand you want the bag, I get it. But I've talked to more people lately who are more unhappy with their career because most of the conversations have been around conversation. Yeah. Yeah, totally agree with that. Yeah, no notes.

Yeah, no notes, I love that. So in your career, have you hired anybody in your career or been a part of hiring? Just talk about that. What do people do well that you like, maybe in the past, what do people really bomb that you're like, ah, don't do that. Can you kind of shed some money around that? Yeah, and I don't even know if I'm a great person to speak on authority. I feel like I didn't hire well a handful of times, I hired. I love the honesty. More and frequently than I hired well. I think what I've changed, maybe that would be more useful in my approach is, you know, I was in a traditional big company going through the normal application process and like, all right, doing the lead code questions.

Yeah. And I don't think anything's wrong with that. I think it's good to have like a basic screen. But really the best experience I've had is whenever I have been willing to say, hey, can you, like, I will pay you three month contract? Like, I want to work with you extended. Or some kind of like, some period that makes sense for your company. It's not going to be the same for everybody. Sure. But like, all right, I want, I have a project. I want to pay you, you know, obviously going through some initial screening process. But like, all right, I'll work with you three months.

And then like in three months, let's kind of reassess if it's working for you. See if it's working for you. Talk to that. Yeah. And I went through that process with even cow.com, which is a really popular kind of like scheduling company. Yeah. I really love that process. And I chose not to move forward with that. You actually contracted. Yeah. Yeah, exactly. And so I really loved working with them a lot. And I went there. And that was kind of whenever I was deciding, like, what do I want to do with my life? And I was passionate about localization. And so I started talking to them about that.

And they kind of said, hey, happy to go through this contract process with you. It won't be able to be like fully localization. It's like, cool. I need a job anyway. And so I went through that process and really loved everyone there. But at the end of, you know, a few months, just like, yeah, I think I would just be better served following my passion. And so no hard feelings. I love that. And so I really, that really impacted me a lot of like, OK, I'm going to do this indefinitely now. Whatever I have the ability to hire. Yeah, I've talked about that a lot.

I think companies don't use contract to hire as much as they should. I think, you know, realistically, my hot take is, I don't think you can really evaluate anybody. Yep. In a traditional interview process, I don't think you can evaluate the person as a person. I don't think you can evaluate a person as a coder within three four interviews. Even six, eight interviews. I just don't think you can evaluate who the person is until you get them working with the team on something that matters. And so I've always been a big proponent. You know, we always call it in the staffing world or right to hire, meaning basically like, if both of y'all want to do it, it'll be great.

I think more companies should do that for a minute of you perspective. I think it's great. I think it doesn't waste time. You can work on a problem. The other person feels validated because they're getting paid. Yeah. And you work towards one goal. I think it's great. Yeah. And it's not a perfect system. Someone needs like health care or whatever. That can't necessarily work. But it feels like the least bad experience. Yeah. Absolutely. So anything else for what? What are some? I am curious. What are some mistakes you've made hiring? Because I'm really bad at hiring. I feel like I'm bad at hiring. But like, at least I'm awful at interviewing.

So like, do you have anything that maybe you are open to sharing that you kind of like? Should have done this. But in hindsight, you know, whatever. Yeah. I mean, I think it goes back to what you said. Like the process itself doesn't really lend you the ability to be confident about the decision. And like I always want to err on the side of like thinking of the best of someone. Same. Same always. And so yeah, I would say my mistakes are just going through the process and having a mindset of like, will this process sucks anyway? And so I like, I guess I'll just choose this person.

They like checked all the boxes, but out without really like feeling it in my gut. And I can't say I've ever felt it in my gut by going through that process. And maybe that's not, maybe it's unreasonable to expect to feel it in your gut. I don't know. But yeah, so the parts where I hired well, I went through the same exact process. And it just will happen that person clicked in a bunch of different ways. And whenever I didn't hire well, it wasn't that person. It was just they didn't really mesh with what the job was or I kind of shared it with this understanding on how they would interact long term based on a short interview.

So I think it's the process that was the mistake. And it was just luck that sometimes that worked out, sometimes it didn't. Yeah, that makes sense. So I just wrap up here on my podcast. I always ask every guest. If you could go back in time and tell young Aaron, one piece of career advice, what would it be? Career advice. I don't know. I think I feel good. In general, I don't think that I'd, I like where I am. So I wouldn't want to like, butterfly effect myself into somewhere that I'm not. So I think it would probably be to like not try to do the unicorn start up.

Yes. Yeah. And like that was just a lot of drama. And then I would probably say also just like, don't code until you talk to someone. Like find someone that is excited about like, hey, could I make this thing for you? And if they're like, oh, yeah, yeah. And you know, maybe not. So the mom test I think was probably the advice I would give tell myself is to read the mom test early on. I love that. Yeah. I love that awesome. Well, thanks Aaron. Yeah. Hey, you did it. You listened to an entire episode and I am very grateful. Cause you know why there's a lot of podcasts out there.

There's a lot of episodes and I myself rarely finish an entire episode. So I appreciate you so, so much for listening. Quick reminder, please rate and review this podcast in the app store. I want this to be discoverable to others and the only way that happens is if you take the time right now and rate and review it. Right now, unless you're driving, then don't do it. So thank you again. If you need to reach out to me at T-Dasting on all social media handles and I hope you have a fantastic day.

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