#176 From Therapist to six figure freelance dev
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Welcome back to the Free Code Camp podcast. I'm Quincy Larson, teacher and founder of freecodecamp.org. Today, we're talking with Kelly Vaughn. She's a self-taught software engineer who ran her own developer agency. She was also the founding CTO at a financial technology startup. Kelly runs the popular Ladybug podcast focused on women in tech.

We're going to talk about how to get into freelance and ultimately create a developer agency and get clients. She's also going to share tips for navigating the current developer job market. We're going to learn how to move from freelancing to working for somebody else. And we're going to hear about tips for recognizing burnout so you can know when to take a break. Hey,

Hey, Kelly. Welcome to the Free Code Camp Podcast. Thank you so much for having me. I'm excited to be here. Yeah. Well, you have had such an interesting career, of course, like learning coding on your own as a 12-year-old and then landing your first client at 14. But I'm sure along the way, you...

learned something that like, it was, it was kind of like a rock in the shore, in the sea that, that like maybe you scrubbed upon, I'm not sure what the verb is, but you scuffed a rock and you're like, Oh, I need to tell other people to look out for that rock. What was one early thing that you quickly learned? Oh, look, look out. There'll be dragons there. Yeah. If you, if you focus all of your time and energy on one building on one particular platform, you will find that you're actually setting yourself back technically. Yeah.

For me, that was with Shopify. And things have changed a lot since I started. Again, I started building on Shopify over 10 years ago. But I can say that I did not learn TypeScript until probably three years ago. And I started coding when I was 12, like a very long time ago. And that's a long gap to not understand core technologies that everybody else is using. I also...

learned the difference between web development and software engineering as far as what technologies were being used. The whole concept of just back-end development, building an application was totally lost on me for at least the first half of my career coding. So I had a lot of catching up to do when I stopped running my own company and started working for somebody else. Yeah. And just to be clear...

It's because you were building on some platform that provided a lot of abstraction, so you didn't have to necessarily worry about that stuff. Yes. And so you became overly dependent on the tool. Would that be a fair characterization? Yeah, exactly. Exactly. And most of the work I was doing was front-end development, so that does lean into it a little bit. But there wasn't such thing at the time. You were not compiling anything. And so you were writing vanilla JavaScript or even jQuery. Right.

I spent a lot of time writing jQuery well into my 2010s. Yeah. And of course, jQuery was famously deprecated to the point that even the dev who built jQuery was saying like, don't use jQuery anymore. Please stop. Yeah. Yeah. So that's a cool lesson. Like, so how did you kind of like discover, oh, wow, I've been like so dependent. Like, was it a series of revelations? Like what? Like, were you at conference talks and people asking you questions that you didn't know the answer to? Like, how did you kind of like...

stumbled upon this fact that like you've been kind of held up by this tool that made your life a lot easier and kind of delayed you learning a lot of other stuff that you probably should have learned. Yeah. It came from two angles, both socially and professionally, I will say. From socially, like

Take on social media, for example, watching what everybody is talking about, the technologies they're using. I'm like, I use none of these. What is happening? I can write the best CSS and HTML and vanilla JavaScript all day, but nobody's writing vanilla JS anymore for the most part. But professionally, I was building a lot of Shopify themes when I was running my agency. And when I had more and more customers asking me or clients asking me for Shopify apps,

And this would extend the functionality of what Shopify can do out of the box. And this required more full stack thinking. And I had never built an app before. And I had absolutely no idea what I was doing. I built my first app for a client back in, I would say maybe 2018 in Ruby on Rails. And I had never touched it before in my life. And I have no idea how that app worked, but it worked. Yeah.

Yeah. So you're talking about like specifically like Shopify apps. They just generically call kind of like widgets or extensions or something like that. Yes, exactly. But it's an application. It's, you know, any other web app or software app that you would build. It's similar in this case. Yeah.

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How did you go about like diving into something like Ruby on Rails? And Shopify, I think famously is written in Ruby on Rails and Ruby on Rails, like Rails is the, I guess, main thing that people still use Ruby for. I hope that's not overly generalizing, but I know. Yeah. So Rails, of course, this famous platform or framework that makes web development a little bit saner by applying convention over configuration, essentially saying like, Hey, I know there are a lot of ways you can do routing. This is how we're doing it.

If you don't like it, you can use some other framework, right? Exactly. So it's very opinionated and that allows you to move a lot faster without having to labor over every little decision. You can just learn the Rails way of doing it. Yeah. And then you can focus on actually getting things done instead of fighting holy wars over different paradigms and approaches. Yeah. And the reason why I had chosen Rails for that, honestly, was because the only tutorial available at that time was in Rails.

It's like, okay, well, if I need to build this app and this is all I can find, I guess I'm going to learn Rails. There was no more deep thinking beyond that. But just the concept of Ruby as well was so difficult for me to grasp. I have been professionally writing code for...

of more than, well, more than half of my life at this point, I needed a tutor to get through AP computer science in high school. I could not understand it. And that was in Java. Yeah. And Java, of course, notoriously frustrating language to learn. Yeah. Many people listening to this may have tried learning Java. And I will tell you, if you did not enjoy learning Java...

Take a deep breath and try learning Python. It's much easier. Try something else. I mean, I wish I had discovered Python so much earlier. I discovered Python in about 2015, I want to say. Yeah. And I was like, this not only doesn't make sense, but there's, as you said, like talking about opinionated languages, like the way, like you have to do it this way or it's not going to work. And like, I'm a rule follower. And so if you give me a set of rules to follow, I will follow them. Whereas JavaScript or, you know, any of the JavaScript family, it's the wild west.

And you can do whatever you want for the most part. And you can flex and bend and things will technically work, but it might not actually be written well. At least you know with things like Python, what you're writing. Obviously, for any language, there are performance things you need to be thinking about. But at this stage, it's like zero to one. Give me rules. I'm good.

Yeah. Well, I want to dive into like your early learnings because my understanding is, you know, you're, you joined a very illustrious, uh, collection of people who have been on the free cocaine podcast who got their start with Neopets. Yes. What is Neopets for anybody who is born after 2000? Oh boy. Uh, Neopets is a website where you can have your own virtual pet and you can, um, you know,

feed it and create a little house for it and have like a community based side of things as well. So they had a forum, they had communities that were called guilds. You can build, you know, your own personal website on there and you can chat with anybody. Uh, and so I, I joined Neopets very early on and I wanted to figure out how I can make my own guild, my own community. And in order to do that, to customize it, you needed to write code. You needed to write HTML, CSS, like that was it. Uh,

Uh, and so I was talking to my dad about this at the time and my dad has a very technical background as well. He was a COBOL programmer. So I've been around it for a very long time around programming anyway. Uh, and I was like, Hey, I want to learn how to code. And so he like buys this book for me called HTML goodies. And he's like, here you go, go have fun. And that is how I learned how to build my first guild on Neopets.

Yeah, and I loved the expressive possibilities of the early web like MySpaces and other websites where you could actually customize things. It was amazing.

Everybody's Facebook page looks exactly the same boring color of blue. I hated Facebook when I first joined for that reason. I'm like, I can't customize anything. I was selling my space layouts for $10 in middle school. Yeah. And that's what I want to get into is like your early hustle. So I know lots of people who are developing software like in their teens and, you know, even preteen, like 12, but I,

it's less common that people are actually making money from their adventures. Yeah. Maybe you could talk about the business acumen that you had early on and how you went about getting your first clients. Yeah. So my very first client was a family friend who... It's kind of funny. I went full circle and having spent so much time in e-commerce in my career, my first...

freelance client was a hunting supply store that needed an online catalog. There was no e-commerce component to it. You could not purchase online at this time, but they needed an online catalog. And I had so much fun having like a very specific project to build. And my payment for that was a t-shirt. This t-shirt was an extra large. It definitely did not fit my very tiny, you know, 14 year old frame that I had. Um,

And completely forgot about this shirt, long time. Actually, fun story. My dad texted me about six or so years ago and was like, hey, you'll never believe what I found. And he just sends me a picture of this shirt, the hunting supplies shirt that he was using as a dust rag in his laundry room. Wow. Well, at least it was used. Yeah.

It got used. Exactly. Yeah. That's so cool. Like a 40-year-old with a giant oversized hunting supply shirt that she got for a holiday comfort website. Yeah. Very cool. So where do you go from there? Like, I mean, you mentioned like, you know, big things have small beginnings and that is a

Clearly a very small beginning, but I mean, you went on to building kind of like an entire agency out of this stuff. But can you walk us through the progression of going from a solo dev just...

building for various clients to actually having a pretty sophisticated organizational setup? Yeah. Yeah. So the theme of my life is I say I never want to do something and then I do that thing like nine months later. I don't know why this theme keeps on happening, but this is who I am. This started with I never want to code for a living, which is why I have three degrees, none of which are in computer science.

For the transitioning from freelance to agency, I was doing a profile with MailChimp. They titled it A Freelance Success Story, and it's still in my wins folder forever because what a great title, right?

And in this interview there, I talk about how I never want to start an agency. I love this freelance lifestyle of just working with other freelancers, like a freelance designer or a copywriter, for example, and we're just jamming on random projects. And this is so much fun. And then I, not even three months later, it was like, I hit a wall because I hit a maximum, uh, like a cap on the projects that I could actually sign on, which is about $10,000, uh, for a website.

And I was like, I can't break past this wall without looking more, air quotes, legitimate and having businesses take me seriously as not a Kelly Vaughn, the freelancer, but as an agency. And so six months after that, I officially rebranded as the Taproom Agency and turned that into an actual fully fledged agency over the course of the next

That was 2017 over the course of the next five-ish years. I grew it to about 25 people globally. So it gets addicting after a while. Hiring your first employee and having them on payroll is terrifying because you're like, I'm now responsible for somebody's livelihood. And then suddenly you have 25 of them. You blink and you're like, oh, now I have this entire team. And there were lots of highs and lows that

We went through the pandemic with that. Being an e-commerce agency, you can imagine the boom of clients that we had at that time, as well as VC money being so like, oh, you breathe, here's some money. Wow, I've never heard of agencies getting VC money. Did you get VC money? No, we had clients with VC money. Oh, okay.

So there's just like tons of money sloshing around where people would not balk. Exactly. You know, like relatively high figures for getting things done. And then everything tightened up. Yeah. And suddenly they weren't spending money. They were getting very efficient with their money. And at this point we had moved up market so much that I think at my peak, the largest contract I signed was about $250,000. Yeah. So compared to the $10,000 I had done before, that's a pretty big contract.

Yeah, I had passed my million dollar threshold. Like that was my goal. I wanted to make a million dollars in a year. I think I did 1.4 million that year. And then it just came tumbling down.

And it was a very, very quick downfall. And even to this day, it's one of those things that I'm like, should I have done something differently to make this last? Or did I just kind of like, did I wait too long to make the hard decision to lay people off or shut down the agency? Because it was no longer not just working, but working for me either. Yeah.

Yeah. I mean, if it's not too painful to recount like the series of decisions and like a lot of people out there, like we're going to get into how to build like a freelance kind of empire like you built because I do. Do you still think it's possible to do that? Is it going to be harder now than it was during the pandemic?

I think it's honestly so much easier now. Okay. I absolutely want to hear why you think it's easier. And I'm going to put a pin in that. Let's talk about the sequence of events that like, if you can go into more detail, like the individual wins along the way and like milestones and then kind of like where things started to go back down. And then at what point, like in that downward curve that you identified, oh, things are going down.

Yeah. Yep. Okay. So I mentioned this was around 2016 or yeah, about 2016 or so when I had hit my cap of $10,000. That was the biggest contract that I had signed. October 2017, I rebranded, officially launched the rebrand as The Taproom. I signed on not even a month later, my first $32,000 contract. So I'm like, okay, something's working. This is great.

At this time, I'm noticing that we're getting more and more interest in e-commerce and building online stores, and the budgets are starting to increase as well. I noticed that as I was asking for more money, people were not really pushing back on me anymore. I'm like, oh, okay, I'm going to keep on pushing more and more and more. Worst they say is no, and then maybe I dial it back at some point.

And so I continued doing this through 2018, 2019. At this point, I think my team is maybe around 12-ish people. A mix of full-time employees and contractors, depending on where they live, because registering your company in multiple states in the United States is a very difficult thing to do without having actual HR people working for you. And so...

around 2020, beginning of the pandemic, the budgets start to tighten up. We don't know what's happening. Is it really just two weeks? We know it's not two weeks. And so some of my clients start pulling back their ongoing development budget with

me. This is not like project-based. This is getting customers on a retainer because you know they're going to be spending X number of dollars per month. Service businesses are very notorious for not knowing. You have high highs and low lows. Like ebbs and flows of cashflow are really, really rough in service business. Retainer contracts help

you know, stabilize that some. So the retainer contract was starting to dial back a little bit in 2020. And at the same time, I'm starting to, I've decided to take this bet that we know smaller businesses are starting to dial back, but there are a lot of larger businesses that are still getting a lot of VC money.

And if we go after the direct-to-consumer brands that have the VC money that need a full rebrand, some more custom work that they can't typically do on Shopify just out of the box, let's go after them instead. And then we're going to hike up our prices.

And so we do this. We are striking a really beautiful balance between getting these larger contracts coming in, $100,000, $80,000, $150,000, while also keeping our retainer budgets sort of stable. They were dialing back a little bit, but enough where we were still making enough money.

to cover payroll and continue to grow. And things spiked so much during the pandemic that we ended up needing to hire more people, which is how I ended up hitting about 20, I think it was 24 people total with contractors, of course, globally as well. And around 2021, like beginning of 2021, I hit a wall.

And I'm like, what am I doing with my life? I feel like all I'm doing is just like churning out the same projects again and again and again. I'm not getting joy out of this anymore. And I end up taking a month off work in May of 2021 to kind of just reflect of like, what is next for me? At this point, I am planning to put two of my employees into leadership roles to kind of take over the

at the agency to continue to close deals. And through this process, during this month off, I end up actually co-founding another company.

And this is a product company, not a service company. So this is in financial technology. And we ultimately decided to go the venture route. So we're like, okay. Awesome. You said so much. I just want to recap some of this. Yeah, sorry. No worries. I take notes when I listen to people talk. And then I try to digest and recap to make sure I've gotten all the juicy morsels.

It's a long story. Yeah. So just to be clear, retainer is something that you use where you essentially get the money up front?

And then later you can kind of build them, but you have the cash on hand. So that gives you the cash flow to be able to make your ends meet. And it also kind of like, it's also kind of like when you go to like an arcade and they give you a bunch of tokens and the tokens are like, it feels like separated from money because you're like using credit instead of actually like putting a dollar bill into the machine every time you want to get some more coins and stuff like that. Yeah. Or you're not actually spending quarters. So it's kind of like a,

Almost like a psychological trick to get people to, oh, what the heck? We've got the budget for that. It's on our retainer or something like that. Is that kind of how it works?

It is. Yeah. I mean, it's also helpful for the businesses because they can be more predictable with their spend as well. If I say, all right, I'm going to, if I'm billing hourly, for example, and my rate is $100 an hour, I'm just throwing out numbers for fun here, and you're paying me $2,000 a month, that means you get 20 hours per month to use whatever you want to use it on. Once those 20 hours are up, you don't have time available until the next month.

So it becomes predictable for them and it becomes predictable for me as well. And then on top of that, you were also going up market a little bit and diversifying your customer base because there were a lot of B2C, business to consumer type companies that were still getting VC money. So they still had the assets, they had the cashflow to be able to contract out work. So how does it generally work with these companies when you're working with them? Where do their budgets come from and how do they figure out

okay, we need an outside agency to do this versus let's just have our own devs do this. A lot of direct-to-consumer brands in particular don't staff developers in-house.

I work with a lot of direct and consumer companies, and then there are also larger organizations like Nestle, for example. They have developers, you know they have developers, but they have innovation teams that typically are trying to move a lot faster. And so instead of using in-house development teams, they will outsource that work to just say, hey, let's move fast and let's innovate and let's just figure out what works and what doesn't. It's a lot less at stake.

And so they don't use their in-house team to build those types of, uh, those types of projects. Yeah. And I can tell you that like a lot of times from what I understand organizations, they'll have like a certain type of engineering culture and they'll be like, all right, we have to do this, you know, very carefully and we need to plan all this stuff. And a lot of times, uh, somebody is just like, we need to do a quick experiment with this or we just need to get this live quick.

quickly. And we don't want to like shift all of our talent off of this or have to apply our own internal process for just getting the simple, like, and I hope I'm not denigrating too much, but like relatively simple Shopify website up or something. No, absolutely. Absolutely. And some of these, some of these things I can, you know, you can whip up a Shopify store in a few hours.

Like some of them are truly fast things. They just want to test something. The projects I was taking on were less that and more like, hey, we want to test bringing this in-store brand online and allowing customers to purchase this product online. Or, hey, we want to test introducing subscriptions, like a subscription model for this. Can you help us build that?

Yeah. And what proportion of the work you were doing was in Shopify? Was it kind of exclusively a Shopify shop or would you use other like WordPress and WooCommerce or different things like that as well if the client wanted it or did you just...

How did you go about that? This one was strictly on Shopify. Okay. I made that a line. That way we were not diversifying or splitting our talents too thin either. Okay. That makes a lot of sense. And obviously you can just be like, we are the Shopify shop. That's like our specialization. Was that a helpful marketing? It absolutely was. We know Shopify front and back because we don't worry about anything else. Yeah.

So would you say that that is actual advice to somebody who wants to be a freelancer or who wants to eventually build like an agency, like a stable of freelancers that are working in tandem, uh, to pick like a specific tool and get known for getting, for using that tool?

I would say it depends on how big the market is for that particular tool. And if it's already very crowded, it could be harder to kind of break in. It could be helpful when you're just getting started to allow yourself to kind of explore to see what works best and also what you're going to enjoy the most as well. Because if you find yourself building, let's say, Webflow, like on Webflow, and you're

And you're like, I hate everything about this, but this is where I'm getting clients. You're not going to keep on doing that forever. Yeah. And we're going to talk about burnout because I know that was, I mean, you just mentioned that you were kind of getting burned out of doing Shopify agents. But one thing I want to come back to is you did say that you think today in 2025 with all the uncertainty around like AI technology, all the uncertainty around other geopolitical things, like you still think now is

potentially a better time to start an agency than it was back when you were doing it? I think it's a great idea. And maybe this is a very spicy take, but I think now is a great time to dig in there because a lot of these technologies are still very early on. They're still nascent. And you're going to have to adapt your business to

However, companies see fit and how technologies are changing over time. But there is still in having, like I spent three years working in AI. So I know this, I've seen this, that there's still an inherent distrust in a lot of companies to adopt AI. This is changing, but there are still going to be clients and customers and companies that want humans to build the thing. I don't think that's going to go away.

Okay. And where do you think the distrust in AI, I mean, it's coming from many different angles. Some of it might be like, we don't know what the legal ramifications of using, you know, a model that is trained on a whole bunch of stuff that they won't publicly disclose because they'll immediately get sued, you know, like stuff like that. Like, like what are the different dimensions of distrust that you've encountered? Uh, and we're kind of jumping ahead to AI, but since you mentioned it, I want to dig deeper into that. Yeah. Uh, I mean, like you call it, uh, legal and ethical concerns, uh,

definitely. How is my data being used? Where is this being stored? Who has access to my data? There's just the change in technology moves so incredibly fast with AI because we are learning so much as we go. We are definitely flying this plane while we're building it. And you constantly have to change. You constantly have to look at what's new. It can be hard to keep up with it. And it's hard to build trust with something when it's constantly changing.

And we often also see anything that can be built for good can also be used for bad. And you don't have control over human behavior. And this is a very social thing that happens in humans. There's always going to be somebody who can find a way to game a system. And you will always see people who will want to use AI for something bad.

I'm not going to name examples, but I think we all know that those examples exist out in the world. And so there's a lot of distrust in like, if I build this with AI, can somebody take advantage of this? So I see that as well. Yeah. I mean, the main thing I see is just people cutting corners and being lazy and ultimately having bad products as a result. Yes.

I'm sure you've probably seen your share of that as well. Yeah. Can you share some horror stories of situations where things have gone completely awry because people adopted AI too quickly or they were too liberal with passing off tasks that used to be done by humans to AI just to, frankly, to save money? I think that's what 90% of the use case of AI is, is saving money. Actually-

90% of the use case of AI is saving money. Agree or disagree? Ooh, that's a good one.

I don't know if I fully agree, mostly because it's a very high percentage. I think a lot of it is saving money, but I think a lot of it is there's a creativity piece to it as well. There's a curiosity about technology piece as well. I wouldn't say it's a 90-10 split. Maybe it's a 70-30 split. Okay, and can you give me some examples of creative applications of AI that you've seen that you're like, okay, this isn't just trying to replace...

Some inexpensive artist in Vietnam who is going to be drawing the assets or somebody who is building 3D models. But this is actually a novel thing that humans couldn't do before. Yeah. No, I mean, I can say all the positive things about my former company, Spotty Eye, the one I just left. Yeah.

they're using AI for physical video. And this is something, you know, you often, you see a lot of AI for like development and, you know, the image generation and that kind of things, LLM sentiment analysis, to be able to have a set of eyes watching video at any given time to watch videos

actions take place or even be able to say this action might happen based on how things are happening in the video. Let's say a vehicle, you might be about to see a crash and you can see the speed, you can detect the speed of a vehicle in that video and then take action automatically based on that.

You know, we were able to see things like, you know, imagine you have a car wash and you have two vehicles going through the car wash. One hits the brakes and they're not supposed to be hitting the brakes or you're in park or, you know, not in neutral. And you see the other vehicle getting closer and closer and closer. AI can detect that speed of like, oh, this might crash and send a signal to the hardware that is controlling the car wash and stop the belt. So all cars stop so you can prevent that crash from happening.

You can use it for business efficiency. You can use it for safety. You can use it for security. There are so many examples of how this can be used. I also met with a prospect one time who was talking about how they wanted to make sure that their store shelves were constantly stocked with the right food. Think like if you want breakfast in the morning and then lunch in the afternoon, how do you make sure the right food is in the right place at the right time so people are actually able to purchase what they want to purchase?

So there are all different kinds of use cases just using video. Okay. So essentially, if I can recap kind of like that use cases, like it would just take such a vast number of humans that it would not be practical to have like a human watching like, you know, a car wash, you know, conveyor belt. Yeah.

Exactly. You wouldn't go out if you were running a local car wash and you're probably getting people to detail the car. You're probably occasionally having some maintenance guy come in to maintain the little spinner things. I have no idea what the terms are. But make sure the vacuums still suck. And...

You wouldn't necessarily want to hire somebody who's going to sit there. Okay, you're going to sit and look at this monitor all day long. And if something looks catastrophic, you're going to hit this button. It's unlikely to ever happen. But it's one of those things that AI could just do. So tasks that would just be prohibitive for humans to do. Cost prohibitive. I like to think about it. And we often talk about like, oh, AI is replacing our jobs. And I like to think about it as AI is a good opportunity to augment your job.

to allow you to focus on higher level tasks and let AI take over on the lower level tasks. Okay. Such as watching a screen and stopping machinery if two cars might crash. Yeah. Okay. That's great. So...

Let's dive back into what you were talking about earlier with like burning out at the agency. If that's a sufficient, like, I mean, I know you write a newsletter on burnout, uh, by the way, I have links to a lot of cool stuff. Yeah. A lot of cool stuff in the video description, uh, links to Kelly's newsletters and, uh, you can read more about her, but to ask like a specific question here, um,

What was it that you saw in yourself when you were working at the agency? Things are going well. You've got all these devs that are dependent on you for their source of income, and you're brokering these deals that are keeping everybody fed, essentially. And you're burning out from...

kind of like doing the same thing. Like you saw that, like I could basically just keep running back this, this, uh, game plan over and over and it would probably keep working. There might be diminishing returns there, but, but I could just stay in this holding pattern for a number of years. Did you get that vibe? Absolutely. Yeah. And that was the problem is like the, I lost the joy of the work and to spend so much of your life working and

I think it's important to be able to derive some joy from your work. And it is hard running a business. It is lonely running a business. And these are the kinds of things that you can't really commiserate with your coworkers about because you're the boss. You are the CEO, the chief everything officer of running your own company. And I was not having fun anymore. I was just not looking forward to working anymore, doing this, I should say.

And as somebody who has always been really passionate about entrepreneurship and about working with businesses and the creativity side of it, for me to lose, that was a major sign for me that I'm burning out. Yeah. So there's like this thing in computer science, uh, like the hill climbing algorithm. And like the idea is when you get to the top of a hill, you've got a really good view. And if your goal is to get to the highest point you can topologically, then you can actually see often mountains, uh,

or that are like taller than the point you're on. But in order to get to them, you have to kind of climb down and then you have to start climbing the taller one. And then maybe when you get to the top one, top of that one, you start looking around. Oh, there's an even taller one over there. And it sounds to me like you found kind of like a local maximum, uh, in that like, you're like, okay, like maybe there's higher. I can go with this, but like, I'm not really interested in climbing cause I can already see higher mountains elsewhere from where I am now. It would, would that be an accurate, like, did you see, did you already have ideas of what you wanted to do?

once you were kind of free of this, you know, gilded cage that you'd built for yourself? Yeah, yeah, I did. Because at this point, we were building more Shopify apps. And so I was actually seeing the world of software engineering more than just web development. And I was really drawn to this.

And I felt like the possibilities were basically limitless on what you could build and how you can grow a company. I've always been a high achiever. I've always been a high performer. This is just how I operate. And so as you said, I saw that higher mountain in my periphery that I wanted to climb. I needed to go down and take a far left turn to do that.

And so in order to do that, as I mentioned, I put some other folks in leadership roles at my agency, took a step back, and then co-founded that venture-backed startup. Okay, let's talk about that venture-backed startup. Yes. And the problem it solved, and then I want to know everything. I want to hear formation. You had...

Co-founder. Yeah. And like a lot of people have co-founders and like I don't have a co-founder and I always tell people like you don't have to have a co-founder. I know White Combinator wants you to have a co-founder, but you don't actually have to have one. And there's this entire book called the like founder issues or something like that. The founder dilemma. And it goes into like the many, many things that happen when you have a co-founder because most organizations do not have like two co-equal.

There is a separation, and every nation state, every most publicly traded companies, they have a single person at the top. Yes. Because there's that natural... Somebody will decide, I have to be the number one, and they'll beat their chest, right? Yep. But I want to talk about that entire process, and I'm just going to shut up and step back

Oh, it's going to be fun.

And then two, they needed more visibility into how those gift cards are being used or not being used because gift cards are a liability on the books.

That's where they show up for accounting, which means it's similar to like the retainers we were just talking about earlier. You purchase those ahead of time or like a Starbucks gift card. It is such a – like Starbucks on their books, since they're a publicly traded company, gift cards are a massive part of their liabilities for that reason. They're like one of the biggest banks in the world if you consider them a bank. I am part of the problem, but I keep on topping mine up. So that's fine. So I had built this app for a client and I was like –

this could actually be a really good product because other customers will want to use this as well. Other merchants on Shopify would want to use this too. And so I was talking to my what was then co-founder. I was like, why don't we turn this into a company? Because I think we have something here. They had more experience on running an app company than I did. I had more experience on the technical side of things. And so that's how we were balancing things out.

out. One of the mistakes we made is we could not decide who could be CEO or who should be CEO. And so we were both co-CEOs. Very few companies that just, it doesn't work. You have to have, if you're going the YC route or the Y Combinator route, you have to go, you have to have a technical co-founder and a non-technical co-founder typically is what you see. I was the technical co-founder for this. And so we...

We're like, let's, you know, we talked about this idea with the, you know, other people we knew in the Shopify ecosystem. We had a really large network of folks in the ecosystem at this point. We're floating this idea. They're like, I want to invest. Like, let me buy in on this because it sounds like a great idea. And so we ended up raising a little over a million dollars in three weeks.

from VCs and from angel investors as well, which was an unreal thing. I had never actually seen seven figures in a bank account before in my life. And so that was a really cool thing to see. And so we grew too fast. We were hedging our bets on a very specific event to happen in the Shopify ecosystem based on an acquisition that had happened. And we were hedging our bets

far too heavily against this one particular event. And the event did not happen.

And so we found ourselves in a position where we had grown our business too fast. We had hired too many people and we were burning through that VC money that we had gotten. And so, you know, all while this is happening, keep in mind, I still have the agency. I'm still running the agency. And this is one of the big mistakes I noticed about the agency is that I'm good at closing deals. And if I'm focused on this other company,

I'm not closing deals anymore. And so what was very natural earlier is suddenly a very hard thing that they're trying to grapple with. And they don't have the same close rates that I had. And so the agency's running out of money.

The VC-backed company is running out of money. And I'm like, I can't do this. I am running two companies at the same time that are slowly reaching this downhill pattern. And I had accumulated a lot of money.

debt for the agency to keep it running. Like low six figures to keep it running, to keep payroll running and everything. And then this is what I was saying. I think I waited too long to pull the plug on the agency. I should have done it months before I actually did. I also think I could have had an opportunity to sell the agency for seven figures and I never did. These are all things I can look back on and I can, you know,

agonize over the decisions I didn't make, but what's done is done. So at this point, I've made peace with that. But I was in probably the darkest time of my life when I came to the realization that I needed to

shut down the agency. I could not afford to run it anymore. And I also needed to leave the startup I co-founded because I could not afford to pay myself and also pay back the debt that I had owed, that I had accumulated from the agency. And so I had to get my first quote unquote real job. And so I had to leave both. Wow. Okay. So I just want to recap that. So you're, you're

running two companies at the same time, which is rarely advisable. Um, and one of them of course is this agency that, um, is in decline. Uh, and, and you're taking a debt and you're, and you're like, for lack of a better word, and I hope this doesn't sound like accusatory or condemning, but like to some extent you're in denial about how, how bad it is, how hard it's going to be to rebuild this agency and get back up to, you know, break even. Um, and, um,

To some extent, like, would you say it was like due to your sense of...

your kind of pride in like having all these people depend on you and like wanting them to succeed and do well and not wanting to cast them out to, you know, an uncertain job market. Like, did you feel protective of the folks working at your agency? Absolutely. Yeah. I mean, I had been working with these people, a lot of them since day one of starting the agency, like rebranding as the agency and the idea of breaking things off and leaving them without a job and having to have them, you know, some of them were, uh,

looking to start a family soon. Some of them are building a house. These are very important life events that me shutting down my agency would absolutely immediately disrupt. Yeah. It's certainly something that I think about a lot running Free Code Camp. Of course, we have a staff of 32 people in 21 different countries, most of whom are international. We've got a few people in the States too. I'm constantly...

Like, like you, um, like don't bleed out basically is what I tell myself. Like every, every month when I'm looking at the bank account processing payroll myself, uh, making sure all the wires go through. Uh, I actually send the wires manually because like one month chase decided to send like multiple wires in the same month. And we got like hit with a $25 fee. Oh no. One B uh, because like they had like offset it by one day and that, that we get like four free wires, uh,

And then the other one, and that's just for international wires, by the way, ACH, uh, it's like 25 or it's like two 50 for the first 10. And then they're like 25 cents each. So if you are trying to run an organization and you're trying to do payroll, uh, setting up automatic payments in your bank account, uh,

Give me a great way to do that. But you just have to make sure you have the cash on hand and then you move stuff over. Like in our case, we're a charity. So making sure that you're moving things to your endowment to make sure that you're at least getting some sort of growth in the market and stuff like that. Anyway, this is not an interview of me. But I frequently think about this. And the thing that keeps me up late at night is like, oh, what if we run out of money? And so that is like...

That keeps me hustling and trying to get grants from different organizations and stuff like that. And essentially to my limited understanding of what you were doing, like understand like, okay, they have given us this grant. We can use this grant to develop this course. The actual cost of developing this course is not necessarily commensurate with the total amount of grant. So we'll have some leftover that goes into the general fund that we use to pay for development on the core curriculum or pays for, you know, localization or instructional other forms of instructional design. Right? So,

I say this because I suspect that I can kind of relate to that feeling that you had when you didn't want to shut this down because you would basically be leaving all those people in a lurch.

with whatever major life event they were going through. Like you said, building a house, starting a family. Some people may be sick. They may be getting chemotherapy or something at the time. And then all of a sudden, healthcare becomes a consideration. There are all kinds of things, reasons why you wouldn't want to walk away from an organization even if it was languishing. Exactly. So again, you're the therapist. You're the licensed therapist. I'm not. But I'm trying to like...

I guess say like I can 100% understand what you're saying. And I, I suspect I can empathize to a degree with what might've been going on at that moment. Yeah. Yeah. I mean, it was, it was, I felt like a failure. Like I felt like I have never failed so much in my professional career. And I, I,

agonized over this decision. And it always like, I have to physically remove myself from an environment to make a decision quite often. Like I cannot sit here in my office and say, this is the big thing that I'm going to be doing. You know, I always joke that I make a lot of life decisions on road trips, but it's true. Like removing myself, that's what I've learned about myself. Removing myself from a physical environment gives me that fresh perspective to say, hey, like you need to take this seriously. And this is a change you really need to be making now.

Yeah. So when you have these big decisions to make, can you like put us in the shoes of like, like this inflection point? Did you make the decision to leave both like, like wind down the agency and to leave the startup? Like was that, what was that time period? Like between the decisions around the same, like the same week. Wow. What was that week? Like, like leading up to that week? I mean, do you remember that kind of crowded moment? Because I was, I was actually in New York for an event and,

And so I just remember breaking down in my room and just being like, I can't do this anymore. I'm done. I cannot do this. And I remember telling my leadership team first at my agency saying, hey, I need to shut this down. I cannot afford to keep this running anymore. And it was the hardest conversation. I cried so much that week.

Just processing and feeling all the feelings of I feel like I filled you. I feel like I filled myself. I feel like I'm a joke of a professional. And I know like obviously when you're in the moment, that's how it feels. Reflecting back three years later now.

I know I did what needed to be done. I'm very strong for being able to make those hard decisions and have those hard conversations. It wasn't easy, but I am a better person today for what I went through three years ago. Yeah. Wow. Um,

At what point did you start to like have kind of that fog of grief, which it sounds like you're describing grief. Yeah. At what point did that recede and did you start maybe feeling like the pangs of excitement of like, oh, now I can do other things? Is that what happened? Was there a moment where you started to like kind of come back into your –

ambitious, normal Kelly self. It came back in like little, little spurts, I would say like little things here and there. Um, there wasn't the excitement of a new adventure, you know, joining, joining an AI startup is like, okay, this is like three years ago. Joining the AI startup is, is very exciting thing. It's still exciting today. It was a very different AI landscape today with the number of companies out there now. Um, so that was exciting. It's a new start. I'm doing something very different. Um,

I still had a lot of weight on me where I had client projects. I still needed to finish up without any team. So I had to do the work.

While I'm also doing this full-time job, this new full-time job I have. And what was really weighing on me was actually paying my taxes, like filing my taxes. Because I was like, I am already so deep in this hole of debt. Like, what am I going to end up owing? And when I finally talked to my... This was like a major turning point for me.

I talked to my CPA at the time. She was running me through. She's like, all right, I have your numbers. Are you ready? I want you to sit down for this. And I'm like, oh no, what is she going to say?

I imploded my company so hard that I got back over $100,000. Whoa. Which went right to the debt. So that was taxes that you'd paid that you didn't need to pay? Yes. Did the IRS actually send you money back? Because I always imagine that being very difficult to actually get them to give you the money back. They actually did. And that's also how I learned that over a certain period of time that money has to be given to you or you start getting interest back.

on that money. If it takes too long, they, they, they waited to the very last minute to get me that money, but they did, but that wiped out over half of my debt. Just that alone. Huge relief. My goodness. Yeah. And that was, that was the moment I was like, I can breathe now. That was it. Like, is the debt, is the debt gone at this time? No, it is, it is long gone since then or since now, like I hustled on freelance projects to pay off that debt as quickly as I possibly could.

Yeah. And so knowing what, you know, just a quick, like lesson time for everybody tuning in. I like to drop these kind of like lesson breaks. You have created an agency. You've run it through the goods, through the lows. You've actually gone into debt, servicing it, um, and making, helping sustain it. What have you learned about how you structure it? And, uh, have you learned anything about like mitigating like personal liability and stuff like that along the way?

Um, I think it's a lot of like what I learned mostly was probably being more honest with myself, checking in with myself. I had no accountability partner really for this because I did run it myself. I have learned a lot about what I need to be asking and who I need to involve, whether it is my husband, whether it is a, my CPA of like, I need you to keep me in check to make sure this is still working. I also learned that I will probably never run a services based business again. Yeah.

This is, I think, I think the agency, my agency chapter, that book is, we're, we're closed. Like we're not, we're not opening for business again. Yeah. So with that in mind, then would you encourage, like what kind of person would you encourage to embrace agency life? I've talked with a lot of people on here who are like big on working at agencies, but I don't think I've actually talked to that many people that actually ran like a big agency themselves. Yeah. What kind of person would,

is a good fit for running an agency and what kind of person might feel like they're a good fit, but actually may not be ideal for such a, such a business. Yeah. I mean, there's a big difference between working for an agency or even freelancing and running an agency freelancing. You are responsible for yourself, you know, highs and lows. You work, you get paid, you don't work, you don't get paid.

agency is different. It is a business. You have employees often or contractors. You are responsible for other people. And there's a lot more liability that comes with that. And so...

You need to make sure you're working with an accountant, you're working with the legal team possibly to structure your business to protect it in any way possible. You are going to be on all the time. It is very hard to disconnect when you're running your own business, especially at an agency because service-based businesses don't follow a nine to five schedule.

Not necessarily. Things go wrong. Something breaks. Holidays happen, especially in e-commerce. So like Black Friday, Cyber Monday, big time for making sure websites are up. You need to be ready and on call in case something breaks.

And you can have team members do this, sure. But you're still ultimately responsible for that. And the larger you grow your company, the bigger the client becomes, the more liability you end up having. And I remember signing contracts with the likes of Nestle or Vitality. And I'm like, I have honestly no idea what I'm signing here. And I send them a contract and they redline my contract. It is half redlined. And I'm like, cool, now I have a better contract.

I don't know what I'm doing. So make sure you're asking for help and you have to be humble enough to ask for that help. You cannot try to figure it out all on your own, even if you've done this before. Yeah, absolutely. So trusting your CPA, trusting your contract lawyer, if you have one, and reaching out for help. Reaching out for help. And be comfortable with discomfort.

There's a lot of discomfort in running a company, whether it's an agency or not. There's high highs, low lows. Again, when you're freelancing, you accept those high highs and low lows. But when you have an agency, you have other team members, they're going to see that as well. If they don't have work to work on, they're going to be like, are we okay? Yeah.

Okay. That's super helpful. So, um, let's talk about life as an employee after you have moved on from these two different endeavors that you were doing at the same time, which seems incredibly inadvisable, but that's the biggest lesson from one company at a time. Yeah. Okay. So, so the, the, the, the kind of like fog is clearing. You said you, you had little, uh, bursts of like, Oh, okay. Like renewed enthusiasm.

Yeah. How do you pick yourself, dust yourself off? You said it wiped off half your debt, but how did you go about wiping out the rest of the debt? And what did the next few years look like for you? Yeah.

The rest of the debt, I continued to freelance on the side. So I continued to keep relationships with some of my clients, kept them on retainer. And a couple of them had larger $30,000 to $35,000 projects that they needed. And so I did whatever I needed to do to get that money paid back because I just wanted it to be gone. And did you do a lot of the actual development and stuff yourself? I did all of it myself. And you did that to...

Not have to further create obligation. Like, were you, did you feel allergic to like bringing on people to work under you after what had just happened? Um, not so much that, that I, this was something I knew I needed to control. Like I wanted to, I knew what, I knew what the stakes were. I knew what needed to be done. And so I knew that I know how fast I can build a Shopify store at this point or an app, whatever it is. And so I know that this is work that I can just knock out myself. Yeah.

And I still enjoyed building. Like that's the thing. When you get to running an agency or running a product company, you're spending less time in the code and freelancing still, still allows you to write code. Yeah.

So you've freelanced, you paid this off and now you're like, I mean, does it take humility to go from being like the top of the organization and being able to call the shots to just joining as an engineer or joining as I believe an engineering manager? Yeah. I joined as an EM or engineering manager. It is, it's an interesting, it's an interesting question because I get that a lot. Like how you're so used to being in control of everything. That's,

That was the hardest thing for me was letting go of that control. I joined a startup where we had not even, maybe we had like 60 or 70 people at the company when I joined. So it was still small enough for me to know everybody and know everything that was going on. And I am also the kind of person to want to know everything that's going on. And so that made it a little bit easier. And honestly, my entrepreneurship background, talking to customers, that brings a unique perspective

perspective into the engineering leadership conversation that I was able to add a different angle, a different aspect to the work that we are doing to make sure that we're actually serving customers in the best way possible. You could throw the mean, like the angriest customer at me and I'd be able to talk them down. Yeah. And maybe you can give like a high level overview of what your day-to-day is like.

As an engineering manager, I think a lot of people think of like, like there, there are various roles within the organization. There's kind of like the executive level, like CTO, CISO, um, you know, people like that. And then, uh, there's like a director of engineering type title, I guess. And that's a form of engineering management. I would, I would presume, but you, you have kind of an encyclopedic knowledge of,

Of engineering management to the extent that – is that – that's the focus of one of your newsletters? Yes. I write a newsletter called The Modern Leader that talks about being a leader specifically in tech companies since I, of course, am an engineering leader. And, yeah, I mean everything from CEO to CTO to VP to director to engineering manager to team lead, like –

There are obviously levels in between senior staff, whatever. But generally speaking, the lower you go down the rungs of the ladder, the closer your view becomes. So when you're an engineer...

you're like boots on the ground, you're writing code, you know exactly what's happening. Engineering manager, you have to know what's happening, but you might not necessarily know every distinct detail. You might help them make a decision of like which stack we should use or like what do we need to prioritize or talk to customers, for example, or you need to collaborate with design and product.

These types of things are what your engineering manager type role looks like. When you become a director, assuming your director level role means that you have engineering managers report to you, your 10,000 foot view becomes a 20,000 foot view where you're responsible for making sure the managers are able to

make their engineers responsible. So as you move up in an organization, if this is what you choose to do, the higher you move in the organization, the broader your view becomes of the work you're doing and how it relates back to the business. And it's less about the day to day work that you're actually doing. Yeah.

Do a lot of devs not feel like a lot of people just insist. I want to be an IC, an individual contributor. I don't want to have my view zoomed out so much that it's like so abstract that it's like, it's like pieces on a map. Uh, I want to be able to actually like be working directly with the code base and stuff like that. And, and,

How did you know that you would be the kind of person who could step back that many layers of abstraction and kind of like almost use people as a layer of abstraction and then the codes underneath the people? Yeah. It's from running my agency because I was already managing a manager through that. I got the experience of being the one who's writing the code to –

managing people who are writing the code to managing a manager who, you know, and going on. So I already had that experience. And I found that I, as I was mentioning, like you should be able to derive some, at least some joy from the work that you do. My favorite part of my job was the people.

I love solving people and process problems. I'm still very technical. I can have very deeply technical conversations with my team, but my value is not in, let's use this technology over this technology, or I'm going to sit here and review your pull requests.

There are other people on the team who spend those, those individual contributors who want to be ICs. They spend a lot more time writing code to be able to do a better job than I would at this point. Yeah. And it's cool of you to like acknowledge that. Like my, my general impression of this is like,

People only have so much time. And so people who are dedicating more of that time to the technical aspects, like re-architecting or creating some new API or something like that, they're going to generally be better at that. They're using those muscles more. Yeah. And thus, those muscles are going to be stronger. They're going to have more fiber in them. And then people who are really good at meetings and doing things like...

So there's like Ricardian comparative advantage. Yeah. Right? Like certain people have like an absolute advantage and then people have a comparative advantage. And I'm not going to attempt to explain that economics concept here, but I will encourage everybody to figure it out. Like you can be really good at...

Doing software development, but that is not necessarily the best application of your time. If you are, you know, like even if you're the best developer on the team, if you're also really good at overseeing other developers, then your time is better spent overseeing other developers than necessarily being. It depends on where the point of highest leverage is. Exactly. Like a hundred devs.

And you're like a really strong dev. You're just one of 100 devs. But if you're a really strong engineering manager, you can kind of almost set aside the fact. And maybe being a really strong dev makes you a really strong engineering manager. But you should be an engineering manager. That is at least what efficiency would dictate. But a lot of this comes down to joy derived from doing the work. And you said that the best thing about work is people.

Exactly. Exactly. And, and I am very good at translating technical concepts into like for non-technical audience and then taking their non-technical requirements and translating back into a technical audience. And that is a very unique skill that you see in leaders that if you want to differentiate yourself as an individual contributor and stay an individual contributor, that is one of the best things that you can learn how to do.

Yeah, absolutely. So I have like a lot of questions I want to fire at you because I'm, you have so many different areas of expertise. One of them is you recently started a newsletter on burnout and,

And of course you kind of walked us through your burnout journey, but, uh, maybe you could add additional color to like what burnout is. Like just give people like a feedback. Like, yeah. Is there a specific feeling that people can like look to, to say, Hey, this is a symptom of burnout.

That's what's interesting about burnout is that it looks different in everybody. For me, I would find myself waking up not being excited to work at all. And I would have a very short...

if the littlest thing made me angry, it was the biggest deal in the world. I would have to make sure and watch what I'm saying around other people because I'd get a little snarky. For me, this is how I react. For some people, they might be really sad all the time. For others, they might just be really angry all the time. Others, they're just like, it's almost like

depression and that you just you know you're you have brain fog you're just you're not really present you don't want to be present like you're you don't want to like you don't find joy in anything that you're doing right now so symptoms are going to look different from one person to the next but the idea is that you know you can do a check-in on yourself to say how am i feeling about the work that i'm doing today am i excited about the future of this company

Am I excited about my future at this company? Those are two very different questions. And you can start to just get a gut check on how you're doing. And don't do it just a single point in time because you might have a bad day. And we all have bad days. And you would be like, I'm going to quit my job tomorrow because this sucks. And then the next day, you're really excited about something that you're about to be building. It could change over time. But look for those patterns over time.

And then what's important is if you see that, you need to decide what is going to be necessary for you to do with that information. Taking a day off work does not solve burnout.

And it's just, it's one of those things like, oh, well, take the weekend or take, you know, take a three-day weekend. We take so much time to decompress from a very heavy, hectic work schedule that three days is nothing. Like, I think there was some study, I don't remember exactly how long it was, but it was like five and a half, like four and a half or five and a half days of like actually disconnecting before your brain can start to stop thinking about work and start thinking about something else.

Um, and, and for me, it takes even longer, you know, I can go on vacation for two weeks and I'm still thinking about work the entire time. And that sucks. I don't want to, you know, that, and that was, that was a major sign for me that I, I was constantly just, I was never disconnecting from work.

That's like such an unfortunate kind of like, I don't know, evolutionary trait in humans that it takes so long for us to like kind of halt that, that inertia or halt the momentum. Uh, so that we are no longer thinking about that and that, that has completely stopped rolling. And now we can kind of turn our attention to something else. Like that is a huge flaw. If you think about the way things get done in the real world and like taking your proverbial eye off the ball for like, you know, several weeks is probably not viable in like,

you know, a competitive space. Maybe if you're making buggy whips or something like that, then you can afford to take like a month off and the industry won't fundamentally change around you. But like in software, yeah, I mean that, that is quite a pickle because, uh, what would you recommend to somebody? Okay. So I'm going to recap what you said first, because I think it's very important. One, you need to, uh,

you know, figure out like through patterns, not just like, Oh, I'm having a rough day. Like you might just be having a rough day. Maybe you didn't get enough sleep, right? Maybe there's some sort of extrinsic thing. Like one of your friends is really sick or you just receive some other bad news. But, but if it's, if you're like randomly sampling throughout the day, maybe like journaling or something like that. And you realize, Hey, like I've noticed the sentiment in my journals has taken like a nosedive over the last three months. Maybe I'm burning out. And then once you had that revelation that, Hey, maybe I'm burning out.

What do you do with it? Uh, and, and I guess that's, that's like the big question is like, let's say hypothetically, it's not tenable. Most employers are not going to say, Oh, it's cool that you take like a six month. Yeah. Take multiple months off. No big deal. We'll just move some people around and you can come back at any time because employers are going to know like,

that that person may be permanently burned out or that they're probably over the next six months going to come up with some idea of what they want to be doing. It's probably not working for your company and that you're kind of like temporarily putting all this stuff in place, but you can be confident that you're probably putting it in place permanently. Do you know the stats for what percentage of people that take hiatuses actually come back to the company and just are cool with resuming the status quo? Is that common? I don't, and that would be a really interesting...

stat to know. And that's exactly what I was going to get to. For some people, a break, even a week break or two weeks will be good for them. And that's all they need. And they can just come back refreshed, excited for work. And that's great if that is the case for you. For me, my burnout was so many months over the course of probably four to six months.

that it did not matter how much time I took off or the role that I was doing. I needed to change. Like I needed to remove myself from the environment I was in and completely change my environment. Similar to how I was saying earlier for making any major decision, I need to remove myself from my environment to think through that.

I made the decision while I was on vacation that, okay, this is definitely the thing that I need to do. Like I need to actually remove myself from this company and start, you know, having conversations about potential new jobs. And so that's, that is what I did. And do you think that that is the most, like if you had to do like a best at one, like in,

Most cases, of course, I'm sure every case has like tons of circumstances. Uh, and I, and you can totally stop me if you're like, I can't give like general advice on this without knowing more about the individual. But like, let's say hypothetically, somebody has come to the conclusion. Like I genuinely think I'm burned out. Like based on everything that Kelly has said here, like I check all those boxes. Uh, this isn't just a phase. Like I, I feel like there's something fundamentally broken with what I'm doing here and a change needs to happen. Like,

What advice would you give to that person from that standpoint? The first thing you need to do is talk to your manager. You cannot keep this in by yourself because they cannot help you if they don't know something's wrong. Same with HR. If you have a good people team that you feel you can talk to an HR business partner, for example, and say, mentally, I'm struggling. I need to be able... I'm very burned out and I don't know what to do.

They will be able to help guide that conversation. If they don't have options, you need to think through what you can do. And I say that because there is a privilege to being able to take time off work that most people are not able to do. We have bills to pay. We can't just walk away from our bills because we're burned out. And so you need to decide, you know,

from your financial situation, are you able to, you know, do you need to leave the company? Is that the only way you can do this? Do you need to leave the company right now? If not, maybe you start looking for a new job instead so you can change your work environment instead of totally remove yourself from the work environment. Yeah. Well, I'm going to play devil's advocate. Uh, my favorite role as a podcast is a great role. Uh,

HR is not there to protect you. They're there to protect the company. It's true. I read this all the time in subreddits and stuff like that. People are always like, why did you talk to HR? They're just going to figure out how to get rid of you with minimal subreddits and stuff like that. Let's say hypothetically you're at some kind of like evil corp.

And maybe that's part of the reason you're burning out because you're helping contribute to like any cause or something. But let's just say you're like, I don't feel comfortable talking with my manager. I don't feel comfortable talking with HR. I'm sure they're just going to use this as an opportunity to shove me out the door and burn and churn. Where are some other places someone concerned about that might be able to go? I would find another peer who's not at the company to talk to. Okay.

You need to talk to somebody about it. That is the whole thing. This is not something you can solve on your own. If you can find a therapist, that's going to be your best bet.

You know, my therapist does not understand tech whatsoever, but we still have very, very good conversations. Um, but you need to talk to somebody about it. And I want to, you know, emphasize, I think you may have said this earlier in the conversation, but you yourself are a therapist, right? Like, like you've studied, uh, you have like a master's in social work. Yeah. So, so you're qualified to like kind of be your own therapist, but it's just like only a full, uh,

Has a lawyer or like serves as their own lawyer. I can't remember. Or a lawyer who, or what is the expression? I don't know exactly what it is. It's like a client or a client who has himself for the lawyer is, is a fool or something like that. Like, like never represent yourself. Never represent yourself. Exactly. Never. Yeah. Never interview as a team like they did in stepbrothers. And, and the other piece of advice is never try to be your own therapist. Would you say that's accurate? Yes.

The nice thing about being a trained therapist is that my therapist and I are able to skip the, so this is cognitive behavioral therapy and here's how we can use this. We skip that step because I know all of that. And we're like, okay, here's what we're actually going to do to kind of talk through. Let's try this coping mechanism. Let's try this thing. Like we can skip that step, but I need a therapist just as much as any other therapist needs a therapist. Yeah.

Yeah. Okay. That's cool. So you have to have the kind of humility to accept, like, I do need help and I'm not going to solve this on my own. So it sounds like that's like step one, identifying you have burnout. Step two, just having the humility to talk to somebody, whether that's somebody at the company, whether that's a peer, whether that's a therapist, it sounds like that's constructive advice. And is there anything else you'd like to say on the issue of like addressing burnout that like my questions didn't bring up that you think is just like a general kind of like

generally applicable thing that people should know about burnout? You can't work your way out of burnout. That is the most important thing you need to remember. And that is the difference between, you know, we're really pushing for a few sprints to get something new out the door. And it's really stressful right now too. I am so miserable in my job and the work that I do that it is affecting my personal life. You can't work yourself out of that. You need to change. Yeah.

Well, I want to emphasize, you said you can't work your way out of burnout. On the subject of work, a lot of people watching this are career changers. Maybe they're trying to get into tech from other fields. Maybe they recently graduated from college into a relatively inauspicious time to be looking for a job. In my humble opinion, certainly if you're trying to get a job in tech, there have been better markets than this one. Yes.

What advice would you have for people? Cause you have hired a lot of devs over the years. Yep. And you probably have a pretty nuanced perspective of like what constitutes a strong candidate, like what you look for. What do you look for? Yeah.

Um, I, you know, I know people don't like hearing this, but a lot of, a lot of jobs come from relationships is from who, you know, um, most of the people that I've hired as of late have been an introduction introduction in some way or another. Um, I have, you know, recently also hired people who cold applied to a role that I was opening, but I mean, just to put this into perspective, the last mid-level full stack engineer hire or like role that I had posted in five days, I got 2,200 applications, 2,200, 2,200.

That's 2,200 people submitting like a web form. Yes, exactly. For one role. For one role. And this is not at Google, which I think gets like more than 1,000 applications a day or something. Yeah, this is an AI startup. I might be 10 times that by now. Okay, yeah. Exactly. And it's tough. I understand that this is tough. What I always recommend is make sure you understand the job description. You don't need to have 100% of the skills listed in the job description, but it can't be a total stretch because, again, this market –

sucks for hiring, for job hunting. And so when you have two really great people, and I've been in this position where you have two really, really solid candidates, but one has slightly more experience than the other, you're probably going to go with the one with slightly more experience. If you are applying to a job that the main stack is JavaScript family, it's React node, and your experience is more on Python or PHP or whatever else,

you might be able to write React as well. But if that's not been your core focus, they're likely going to go with somebody else. So there are a lot of jobs out there. LinkedIn, it's hard to find jobs through that. But I recommend switching, and this takes a fair bit of effort, but I recommend switching to look at what's been posted in the past 24 hours.

is instead of like all of those things. Also WellFound is a really great place to look for jobs as well. Don't just use LinkedIn, don't just use one source to find those jobs. And I also recommend, cater your resume to the role. It is exhausting to have to keep on changing your resume, I understand that. Use ChatGPT to say, here's the job description, here's my resume, how close are they?

And if they're not close, they can make recommendations. Don't let ChatGPT write your resume though, please. I have had in those 2,200 applications I was reviewing, three resumes, one after another, verbatim, same exact thing, different company names. They all use ChatGPT to generate their resume and they all looked exactly the same.

Yeah. And, uh, I would, I would go further and say never copy paste directly from dash GPT for any reason. They're simply like these, these were like, you know, not fine, you know, morsels of knowledge or insight. This is just like a predictive texting, like, right. It's like autocomplete on steroids. And, uh, surely the person who's reading it, their time is worth more than reading like something that was just generated within, you know, a few seconds. Um,

I strongly believe whenever I write my newsletter, whenever I write technical articles, like Free Code Camp, we don't use these things for any of the text that goes into the curriculum or anything like that. We use it as a reference and a research tool. Yes. Mostly because Google sucks now because there's AI slop everywhere. And it's hard to actually find what you're looking for anymore. But also because you can't ask long-form questions. You go pretty deep. And you can do things like what...

what you just suggested where you, you take like your resume and like, like dip these two, like how far am I off? And if they're like, give me a percentage. Oh, you're like 80%. Okay. 80%. That might, I might be able to get it. Oh, you're, you're like 30%. Okay. I'm not even gonna bother applying. Yep. Okay. And then, and then just getting feedback, like how can I custom tailor this, getting some bullet points and then taking that and,

Like rewriting the resume. Rewriting them. Yes. And you said that is exhausting. Like how much time would you spend? Like, oh, okay. So here is like a, just a question that occurred in my head. A lot of people are like, I apply to 10 jobs a day or something like that. Like, what do you think? Like a reasonable saying,

volume of job applications you could do if you are actually like being selective and you're not just firing off at every single job. Uh, because a lot of people are like, I applied to 500 jobs. I couldn't get a single call back. And, uh, my, they're probably not custom tailoring their thing. They're probably not sorting by new, uh, and, and just applying to the newest ones. And, and, you know, fundamentally they may not understand a lot of other things. Yeah.

Yeah. I mean, that's, I don't think there's any specific number that I can really pin down there. Um, what I would recommend is for,

first you can't really treat job hunting as a full-time job it is so mentally and physically draining far beyond what you would expect it to be that i know if you want to cater your resume like two or three a day let's say in in you don't do every single day because again it is a lot of work to do that it's also you know when you're job hunting you're going to get a lot of rejections

And rejection stings every single time, especially when you're like, I was perfect for this role and I don't understand. You don't know. You're not always going to get feedback. I would love to give you feedback when I can, but I can't always give you feedback. Or I can't give you the feedback that I want to give you because you show up in an interview and you are wholly unprepared for this conversation. Yeah. Okay. Well, I'd love to read more about what you have to say about job hunting in general.

What is some advice that you would send back to yourself? Let's say hypothetically you were applying for jobs in 2025 and you had the skill set that you have or maybe like a kind of a junior version of that because you didn't have like, you know, decade plus working as an engineer and engineering manager. Like what advice would you give just more generally for going out and navigating this very uncertain time and this very kind of saturated job market?

The more visibility you can bring to yourself, the easier this job hunt is going to be.

That involves networking. That involves posting about your job hunt journey on places like LinkedIn and talking about, hey, this is what I'm learning right now. And this is how I'm building this thing just for fun because I'm building out my portfolio. Talking about your journey and interacting with others at various companies you're interested in, connecting with folks at companies that you want to get a foot in the door with. Like,

find a way to network with them because everything is so relationship driven. And the more your name shows up, the more likely you are to actually get that, oh, I know who this is. Yeah, I'll have a conversation with you. Or somebody is like, hey, I know so-and-so is interested in this role. Here's their resume. I know they're fresh out of college, but I think they'd be a really great fit and they'll learn really quickly. Yeah.

Awesome. So put yourself out there, maybe learn in public, uh, build those relationships. This sounds like solid advice and, uh, any parting, uh, encouragement to people who are out on the, on the job hunt, who, who've been spending time learning coding and just need to get that job.

Give yourself some grace. This is such an atypical market right now. You need to be able to allow yourself the space to enjoy this process wherever you can as well. Like I said, the more you communicate with others, the more you network with others, it's going to become more fun. Job hunting sucks for everybody. Nobody enjoys it. Hiring is not really fun either. I don't like having to send a bunch of rejections to people either.

So like, just try to find fun and levity wherever you can and make sure you're taking breaks. You cannot, you cannot treat this as a full-time job. You, you will burn out from applying to jobs. Yeah. Well, Kelly, it's been an absolute pleasure having you on the podcast. Uh, I encourage everybody to check out the links to Kelly stuff. Uh, I encourage you all to check out the ladybug podcast as well. I've really enjoyed listening to it over the years and I'm thrilled that you all are coming back and I'm really hyped to continue to learn from you through listening to that podcast.

Thank you so much for having me. This was so much fun. All right. Well, everyone, until next week, happy coding.