An Unexpected Shift from Selling Beer to Coding Bootcamp with Caitlyn Greffly (S7E6)

Updated on | Sign up for learn to code tips

Caitlyn GrefflyCaitlyn Greffly used to travel around the country selling beer, but it got tiring. So in pursuit of a more sustainable way of living, Caitlyn started teaching herself to code.

But the first time Caitlyn applied to a bootcamp, she was actually rejected. She was told she didn’t have enough coding experience, so she found herself learning to code online before applying to a different remote online boot camp called Thinkful. She was accepted, and after six months, she got her first job before completing the program.

In this episode, Caitlyn talks about learning with Thinkful, finding a job in the middle of the bootcamp, and reaching out to get tips, and shadowing experts in the field. She also shares her experience with the supportive tech community as a valuable resource and the changes she had to make with working due to COVID-19. (We also recommend our Guide to Tech Job Hunting during a Pandemic for additional resources.)

This episode was transcribed with the help of an AI transcription tool. Please forgive any typos.

Laurence Bradford 0:00
Hey, and welcome to another episode of The Learn to Code With Me podcast. I'm your host, Laurence Bradford. In today's episode, I'm chatting with someone who transitioned from selling beer to becoming a software engineer. All that is coming up after a quick word from one of our partners.

Interview cake is an online resource that helps you prep for interviews so you can land your dream job in tech. To find out more and get 20% off go to Again, the URL is

And we're back. In today's episode I talk with Caitlyn Greffly. Caitlyn is an associate software engineer at z approved where she works on Legal ediscovery software using Angular dotnet and AWS. I reached out to Caitlyn because her story is awesome. After working in beer sales for seven years where she didn't even work in a proper office, by the way, she decided to make the switch into software engineering at the age of 31. And that's exactly what we're talking about today. We're going to be talking about how she made that switch, what tips she put in place to make that switch in just six months. She has some awesome strategies, by the way, and what it's like being a junior developer in the midst of Coronavirus and the pandemic. Our conversation also touches on what it's like to transition from a coding boot camp to working at your first real dev job. So if you want to switch from a completely different industry and career This episode is for you. Enjoy.

Laurence Bradford 1:50
Hey, Caitlyn, thank you so much for coming on the show.

Caitlyn Greffly 1:59
Hey, thanks for having me.

Laurence Bradford 2:00
So I just want to get right into it. Can you tell us how you got started in software development?

Caitlyn Greffly 2:07
Sure. So I basically did not know that this was the path I was going to end up on. I came from the beer industry. I was selling beer for about seven years before this. And I just realized I wanted to change. And one of the parts I liked about my old job was data analytics. And so I started going down that path. I even applied to a boot camp for data analysis. And I got rejected because I didn't know any coding. And so that was kind of the first that had crossed my mind that I could get into kind of a more tech career. And I never thought of myself as techie. I'm not good with computers when the printer is broken. I have no idea what's going on. But I just started kind of playing around with coding on like Free Code Camp and stuff. And I pretty quickly realized I liked it and I was ready for a change so I made a quick decision to jump into a room Online boot camp called thankful. And I was in that for six months. And then luckily I got my first job offer pretty quickly. And I'm seven months into being an associate software engineer.

Laurence Bradford 3:14
Oh, wow, that's awesome. So you are selling beer for seven years. What did that look like? Briefly? Like, yeah, I honestly don't know much about. I don't know. Is it the beverage industry or?

Caitlyn Greffly 3:27
Yeah, the beverage industry. It was, you know, it was a lot of fun. I got to travel a lot. My most recent job. I had a territory that was from San Francisco, Lake Tahoe, all the way up to the Canadian border. So it was kind of fun. I would wander around I would go to venues like I sold beer, the Seahawks and music venues in San Francisco or just like, you know, Fred Meyer and stuff. So it was fun, but I got a little burnt out on the travel. I was on the road most weeks. Obviously there's a lot of drinking and volved and I kind of just was ready to not have that lifestyle anymore and have something more sustainable as I tried to kind of get into the next phase of my life and think about settling down having a family cetera.

Laurence Bradford 4:13
Yeah, yeah, I can imagine that that would require lots of travel and obviously taste testing and things like that. And it could it could become a lot. You said something, though, in your introduction? I thought it was. It stood out to me. You said that, like something with the data analysis piece that stood out to you with the your job in the beverage industry. So did you work with data when you were selling beer?

Caitlyn Greffly 4:39
Yeah, I did a lot. Actually, in my last job. I was working with a lot of chains like Fred Meyers Buffalo Wild Wings, and they're very data driven companies. And there is national data on beer very detailed, like, I could pick a small town in Minnesota and tell you how many six packs have, you know dish shoots IPA they've gotten through this week. There's just kind of massive amounts of data out there. And so I really enjoy kind of digging through it to find a story and to like, help me help people make better decisions about the beer that they brought in. Hopefully that included mine. And yeah, it was just kind of my favorite part of the job was digging through that data and then creating presentations for it and making complex stuff more understandable. Awesome.

Laurence Bradford 5:28
So okay, so you mentioned you apply to a data analysis Bootcamp, and then instead you ended up going to thankful and did you do the software engineering like they I know they have a handful as thankful but it's online, right?

Caitlyn Greffly 5:39
Yeah. So I think when I enrolled, it was called full stack flex now I think it's called the engineering flex program. And it was basically I think, they said like 20 to 30 hours a week of all remote all online like on your own schedule. I wasn't part of like, a cohort or anything like I made the decision sent in my mind. Money and my first day of school was the next day after they received it. So it was kind of like at your own pace. And it worked really well for me because I wanted to keep my job for the first half of the program. Just for financial reasons, I wasn't super interested in going into a lot of debt at this point in my life. And so I wanted something that I could really work around, like the odd schedule that I had been in the beer industry, right, that makes sense. And yeah, I feel like just like fully quit your job and go to a coding boot camp is such a big decision that yeah, totally makes sense to me why you would want to do both at the same time, especially as you were getting started. So when you were doing both How How did your schedule look? Because you were working full time and doing what, 2030 hours a week? That must have been a lot. Yeah, it definitely was a lot. I was lucky because at the time, my job was also remote. And so I really found out how efficient I could become at doing my job. So I think I probably sorry, former employer, but I think I probably cut my hours down to about six hours a day, I was still able to get everything done. I just, I didn't really take breaks or lunch. And I just, I don't know, I just zoomed through things as quickly as I could. And then I would try to most days, I think I did some in the morning and some at night. And then all day Sunday, I always coded all day. And so that usually ended up 20 to 25 hours. And it definitely was exhausting. I really didn't do anything else. During that time. I didn't have a social life. I don't think I exercise like it was all I was doing was working and learning to code. And then about three months through the program. I also wanted to work in the beginning too, because I felt like I was taking such a risk and making a guess, in terms of going to a coding boot camp like I played around online, but I didn't really know like, was this a career I would really want to pursue. And so after three months into the program, I was like okay, Yes, I really want to go like, put all my energy into this. So that was when I quit my job. And I picked up some kind of side jobs to get me through the rest of the program. But at that point, I was putting in 40 to 50 hours a week, either in the program or like applying for jobs, social networking, all that stuff.

Laurence Bradford 8:21
And apologies if you said this already, but how long were you in the program for start to finish? And kind of like secondary question with that is thankful the kind of program where you sort of pay every month or is it like a set duration? it like, you know, six months? And that's it? I don't know if that question makes sense.

Caitlyn Greffly 8:41
Yeah, it totally does. So I did it for six months. I actually didn't even quite finish my boot camp because I got hired right at the end. But it is intended to be a six month program. If you go over that time, you can either keep going on your own but you won't have the support of like your mentor and some of the time technical support that I found, I absolutely needed. But you could keep going for free or you could continue to pay a monthly rate or 1000 or something a month to continue having that support. I decided to just pay all upfront, so I didn't have to kind of worry about the money as I was going and it was just already done. But I think they also have a refund program. Like if you cancel or finish early, do get some money back.

Laurence Bradford 9:27
Gotcha. So that's really awesome that you got a job before you even finished the program. When did you start applying for positions?

Caitlyn Greffly 9:36
Yeah, I feel really lucky that I got a job when I did because I know people who are super talented who just haven't had that kind of luck. And I the first job that I interviewed for I didn't really it was kind of an accident. I was at a conference. They have a nationally it's called the act w advancing the careers of technical women. Highly recommend Anyone out there? Because it was such a great conference, they helped me with my resume. There was mock technical interviews, there was just great speakers that felt like they were there to like, personally helped me succeed in my career. And I met someone there who had a job opening. And he was like, You know what, like, I love talking to you, I'm gonna send you the technical interview. And I was maybe three months into my time in the boot camp, and I was kind of terrified, but I was like, you know, what, never say no to an opportunity. You never know. And so I took the technical interview, and I totally bombed it. It was awful. But that was kind of the start into when I was like, okay, like, even if the worst thing happens, where you feel like, I feel like I knew almost none of the answers to any of the questions that were on there. Again, I was only halfway through my boot camp. And I was like, even if that happens, like I survived, I'm fine. Like, never going to see that guy again. Maybe Um, so that made me feel more confident weirdly enough to kind of start putting more feelers out and applying for jobs. I think I really ramped up towards, like the fourth or fifth month of, of my time.

Laurence Bradford 11:12
Got it? Yeah, I feel like it's almost like when you go through that early experience, and as you said, he didn't really know what you were doing. It's like, it's almost like the low point. It's only up from here, right? Yeah. All right. Well, cut that out of the way now. I can better prepare for future ones. Have you found that like other jobs you interviewed after that, or you apply to interview for was the technical interview similar to what he experienced that first time?

Caitlyn Greffly 11:39
Now that first one was a timed online technical and so it was like 45 minutes and there were like six kind of short, more like algorithm based questions that I just didn't know. And then the other technical interview I had was, like, a couple hours in person and I did that Some live coding with someone kind of standing right over my shoulder and watching. And if I got really stuck, he could kind of nudge me. And then there was also, it sounds scary. But it was a whiteboard in which we were doing like app design and not like we weren't writing actual code on the board. It was more like, how would we design the front to back end of this app. And then the job I actually ended up landing didn't have like a traditional technical interview, they asked a lot of technical questions. And during the final interview, they pulled up my code from my portfolio projects and asked me specific questions about the code in there. And they asked me a lot of like, kind of vocabulary or understanding questions. But I was really grateful that there wasn't like, an actual technical interview because I think those can be so scary, especially as a junior and just the idea of having to like memorize something when I think so many developers regardless of level are, don't have everything memorized. Even things I've done multiple times before, they're always googling. So, yeah, those interviews where you can just kind of see what it would be like to work with someone, and what their understanding is of the code. I thought were I like those more.

Laurence Bradford 13:12
Yeah, yeah, for sure. Much less pressure, I think. So the company that you you worked at now and you said it wasn't like the whiteboarding, you know, sort of interview? Is it a smaller company?

Caitlyn Greffly 13:26
There is about 150 people there and about 60 of those are engineers, I believe so. Yeah, it's it's fairly small.

Laurence Bradford 13:35
Yeah. Not that small though. Cuz I feel like I was going to say that I feel like at like small startups that are, you know, growing quickly, maybe a bit like their processes and operations aren't as in place yet. I feel like it's quite common to not have as structured of like an interview process. But actually, that's bigger than I sort of thought you were going to say, but yeah, that's really awesome that that worked out for you. And I think you said this in the beginning, but how long have you Been working there now?

Caitlyn Greffly 14:01
About seven months? Yeah. And I think one of the reasons that they do the interview this way is there's just a lot of focus on like being inclusive and I think they see this as a more inclusive interview, which I agree.

Laurence Bradford 14:15
Yeah, yeah, for sure. So you apply to this job. You're finished with the boot camp yet. I kind of jumping around here but before you decided to go to thankfull How long were you coding for? or teaching yourself for?

Caitlyn Greffly 14:27
Like not I I made this decision like way too fast based on like, a very small amount of information and I'm really surprised that no one stopped me before I threw like $9,000 out the window, but I want to say like a week, maybe. Okay, wow, at all I was going off like a gut feeling. And I was also just kind of feeling like done with my current job at the time and I'm kind of an impatient person. So I was just ready to go for it. went for it. Yeah.

Laurence Bradford 15:00
Wow. Yeah, that's that's quite quick. Actually, I'm trying to think if I've had other folks on the show who have had such a fast turnaround time I'm not. I'm not certain. But basically you landed your first job then after only learning for like five months.

Caitlyn Greffly 15:15
Yeah, yeah. Six months. Yeah.

Laurence Bradford 15:17
Yeah. Which is awesome. Like that's as again, as far as like people I talked to that's a very fast turnaround time. But it sounds like you were doing it 2030 hours a week, and then you did eventually quit your full time job. And you were doing like thankful full time, essentially. Yeah, yeah. Yeah. Okay, cool. That's awesome. And when you started applying for your first job, I'm asking all these questions. That's really detailed ones because I know listeners who are just like, just starting out, they have all these like, questions, you know, like the specifics of everything. When you were applying to this job, maybe like five months in or whatever, what was the turnaround time so like, from like, application to job offer?

Caitlyn Greffly 15:58
Yeah. I think maybe Now boss actually kind of like sent me, I think our original communication recently and was like, oh, like our first time talking. And it was very sweet. And I think it was in like mid late August and I got hired in late September, and started in mid October. So yeah, it was about six weeks maybe from my first application to actually getting the offer.

Laurence Bradford 16:28
Nice. And before working in the beer industry. Did you have any other like employment or did you have any other work experience doing anything else? Or was that kind of it really,

Caitlyn Greffly 16:41
that was most of it. I got my undergrad degree in psychology and intended to kind of work with families and children. So throughout high school and college and the year after college, I did a lot of work with kids and classrooms and being a nanny and stuff like that. And I actually kind of ended up coming full circle as I was finishing up the boot camp. One of the part time jobs I got to get me through was working at coding with kids, which is just like kind of a part time summer camp that teaches kids to code using while I was working with a program called Scratch. So yeah, it kind of came full circle, and I got to put all the things I've learned together, but the beer industry is the majority of my experience. Gotcha. Okay. And you just answered my other question I was going to ask about if you went to college before if you had a bachelor's degree what what it was in when you were applying to these positions, and you had this experience that was you know, the beer industry, psychology? Did you do anything in particular to position yourself in a way that would stand out even though you didn't have a traditional computer science degree? I feel like I did a lot of research to see which companies had hired people from less traditional backgrounds. I felt like it might be easier to position myself for a job at one of those places then convince a more traditional company, they should take a chance on me. So I did a lot of LinkedIn sleuthing, which was familiar to me from my sales background, just kind of looking at people. And I'd reach out to some folks who had gone through less traditional routes and, and kind of see how their experience was. And yeah, I think those were the companies that became some of my targets and that I would really watch for jobs. And I wanted to be in a place that was accepting of junior developers and kind of excited to help them grow in the community, because I've heard of juniors having really bad experiences where they get in and, yeah, maybe they're the only one without a CS degree. And so their project, there's prejudice against them, or they're just not well supported. So I think I'm glad that I decided to look more specifically at Companies that did take bootcamp grads. Now that I'm on the other side, I really just want to help all employers see that there's such value in people coming from less traditional educational backgrounds. And it's a great way to increase diversity too.

Laurence Bradford 19:14
Oh, yeah, for sure. And I loved that tip you just shared a bit ago, I've never heard anyone shut up before. And I never even occurred to me. But that is that's really smart. like looking at companies using LinkedIn to see people with non traditional backgrounds and like what companies they work out because you're totally right. There's some I feel like it's becoming less common. But I know there's also companies that will literally require I think, a CS degree for people. Yeah, engineers, but I do think just as time goes on, and education is changing, it's becoming less rigid, but that's a great tip. So did you like compile a spreadsheet? Or how do you organize this information of like, okay, these are the companies that seem like they're more open minded as far as previous experience. I was,

Caitlyn Greffly 20:01
Oh, yeah, I love spreadsheets. So I had, I have a lot of extensive information on there, I would list like the company. Usually I would only put companies down that I thought might have a chance of hiring someone from a boot camp for whatever reason, I thought that I looked up like their Glassdoor ratings, which I know sometimes taken with a grain of salt but I still looked them up. And just all kinds of things like benefits size of the company if they were remote, I didn't really want to be remote at first, which is ironic now because pretty much everyone's remote. And yeah, I just kind of tracked also my contact with them through there. So I would track who I reached out to when when I followed up again, probably coming from my sales days, this experience of just kind of keeping track of contacts and stuff,

Laurence Bradford 20:51
but you didn't use like a proper CRM or anything now like Salesforce, okay. tracking the leads in the funnel and all That right not that fancy. Yeah no that's that's great though and again I love that tip I feel like people like should if they're applying for full time jobs they should definitely think about that because Yeah, that's a good one like evidence from past hires that they that they have. But speaking a bit about like your sales experience and spreadsheets and tracking things. In what way do you think your experience with sales slash the beer industry slash heck even nannying and your undergrad in psychology? Does it help you or how do those things help you today in your job?

Caitlyn Greffly 21:37
I think they helped me a lot when I was job searching for sure. And just in terms of like when I think of building my career in general, because I am more of an extrovert I like going to networking events. Reaching out was something that came easily I wasn't afraid to kind of do the like cold call on someone basically just find someone random on LinkedIn that I had. For their career path and send them a message, I will say that I had pretty good success with it. I convinced a fair number of people to sit down for coffee with me or chat, I found that people in this industry are very like, giving with their time and generous, like they didn't know me or owe me anything. So I think all those things, helps my helped me to get a job. Because I think there's so many, like, I know for the job that I ended up with, there was 200 applicants in the beginning and trying to differentiate yourself from that stack, really just knowing someone even if it's just kind of sending them a message, either through slack or LinkedIn or Twitter that will help them recognize your name when they're going through that pile. So just doing those extra little things. I think were really helpful now that I'm in the job. I think that probably just the communication skills I got from sales or my comfort with it. It's been super helpful to in the beginning, I feel like you have to So many questions, and you have to try and be more communicative to learn. And I think that that's something that's been really helpful for me.

Laurence Bradford 23:09
Yeah, that makes a ton of sense. So you said a bit ago. cold call? Do you literally mean cold calling? Or do you mean emailing? Because if you mean like, truly like on the phone,

Caitlyn Greffly 23:19
I'm like, wow, I haven't heard anyone like, I'm just gonna pick up the phone and call someone. No, not that but like, just like LinkedIn messaging someone I'm not connected with or don't know, or, yeah, like on Twitter, I one of the most successful things I did on Twitter was that I just sent a random tweet, maybe when I only had like, 500 followers, and I asked if anyone would be willing to let me shadow them so I could put my education into context. And I got like six different people who I ended up shadowing, one of whom was Scott hanselman, which was kind of amazing. And he, like everyone was just so nice and generous with their time and so I feel like asking those questions. It just doesn't hurt. Worst case scenario, you get crickets, but whenever.

Laurence Bradford 24:04
Oh, wow. So shadowing Could you explain like what you mean by that? Exactly?

Caitlyn Greffly 24:09
Yeah, so I spent like half a day at six different companies or just with the people and kind of saw what they did in their day to day life. My boot camp was remote. And I didn't know anyone in the tech industry. So I was like, I like coding, but like, what does this job actually look like? Because I know there's more to it. And so I spent half a day at like Colombia shadowing someone there and DevOps. And that was really interesting, but I was also like DevOps. I'm confused What's going on? And, and then I, you know, shadowed some people who did more front end stuff, and I was more drawn to that. And so it kind of helps me feel out kind of what environments I might like more in a workplace. It helped me understand like, what people actually do with their day, and just like make connections and everything One I met with was just such a like wealth of knowledge and information about what it was like to be in the industry. And I got to see so many different points of view. And yeah, really helped me put my education into context.

Laurence Bradford 25:15
That's awesome. You have so many like, Great little like tips of things to do here. I haven't, I guess I guess I know people who who do things like that, but I don't think I've had some on the show yet. who's done that exactly. As a beginner. So that makes a ton of sense. When you put out that request on Twitter. Were you like kind of specific to the area that you live in? Which is Portland, Oregon, right?

Caitlyn Greffly 25:37
Yeah, yeah. I asked if anyone in Portland would be willing to help me shadow them in person. Um, and yeah, like I like I said, I had such a great experience with it. And everyone I shadowed was said something like, I don't know why more people don't do this. This is a great idea. So actually, before COVID I had started to start a program to help connect people who wanted to shadow with People who would be willing to be shadowed and so I'm, I want more people to have that opportunity because I think people are willing to give a couple hours of their day to have someone just kind of sit behind them and like learn what they do and it's like such an invaluable resource.

Laurence Bradford 26:14
Yeah, and I feel like if you're kind of weighing what career path to go down like I think you said like DevOps front end whatever, it can probably give you a good idea of what you like what you don't like, oh, that person's day seems really exciting. Oh, that looks like something I wouldn't want to do every day. Yeah, that's like I mean, it's like real life absorbing what's going on you know, because you can research a bunch of stuff online to watch YouTube videos which I love you I watch YouTube live videos for anything like so many things I just like on YouTube look it up but it doesn't really like replace being there in person behind someone watching Watch. Yeah.

Caitlyn Greffly 26:53
Did you go to meetings with them and stuff? Yeah, they brought me into meetings. I went into like a sprint planning meeting. I went into some stand up some some other just like, Yeah, kind of everything I had some people bring me along like, like I was just really their shadow and then I had some people kind of sit down with me and explain what they did and their path and to this role and there's such a variety of experiences and they were all helpful in different ways.

Laurence Bradford 27:22
Yeah, so Okay, you talked about like the LinkedIn sleuthing finding companies that seems to hire people from non traditional backgrounds. You also just talked about this of shadowing, you talked about, you know, asking people to coffee, cold, emailing all that. Is there anything else that you did in those early days that you think helped you learn more about the industry, make connections get the job you have now?

Caitlyn Greffly 27:45
I think I mentioned Twitter, but I think that was more helpful of a resource than I could have ever imagined. I was not on Twitter before I started my boot camp. And I started an account at around tech, I think on the first day of my boot camp. Just thought, hey, this will be a place where all right things that I don't know or things that I'm learning and maybe need some other people in the industry and it was such a valuable resource because I would get stuck. And I would say like, I don't understand react, like Does anyone have any other resources and there'd be like 50 responses and people leaving resources and like giving suggestive hints and just like cheering me on, and I was just amazed at like, the supportive tech community that there's on there, obviously, not every single person is supportive, but the vast majority. And then I also think, like I mentioned that kind of before, but making that personal connection with someone, whether you whether they work with a company that has a job you're interested in or not like I think just making those connections were really helpful. So I joined all the local slack groups, you know, Women Who Code here, there's PBX women in tech. There's like a startups channel. And there's always jobs being posted and reaching out to a specific person, instead of just applying, I think was super helpful in terms of for one, it could tell me pretty quickly whether I was wasting my time applying or not because some places say two years of experience required and they really mean being a junior from a boot camp is fine. And some places say two years and they really mean two years or more or so just making those personal connections were really helpful. And I think it just made me feel better about my chances just having people to talk to

Laurence Bradford 29:39
awesome, that's great. So I want to switch gears a little bit. I you're talking about all this stuff, right, like in person shadowing, obviously now, at the time we're recording at the time this is going to go live too because it's not gonna be that much longer after we're recording this. Obviously Coronavirus COVID-19 is is affecting lives for everyone across industries in varying ways. What has it been like for you as a junior developer? Especially because you seem like very outgoing, very extroverted, you know, you love to ask people questions you love to get face to face. I know there's some folks out there who like, don't like doing that. But you seem to enjoy that. What has that been? Like? I assume you're totally working from home now.

Caitlyn Greffly 30:22
Yeah, so I was fully in office leading up to this. There is some flexibility at my company, people will sometimes work remotely one or two days a week. I think I've done it a handful of times, but I did really like being in the office, like seeing people. And so it's been about two months now that we've been working fully remotely. And at first, it was really hard because I think it made me very aware of how many questions I had. Because if you're in person, you can just kind of swivel around your chair and be like, Hey, what's that thing and someone would give you a quick answer, but I had to like type them all out and it made me feel like oh my gosh, I have so many questions. And then I think I felt sometimes like in the beginning I, I felt like I was lacking some of the motivation or energy I have in the office I think because I am an extrovert and I get a lot of energy from other people. And it was just it was hard to adjust. And it was I was feeling defeated a lot more often. I think one of the things that really helped me switch into a better mindset was I wrote an article on Dev. That was like, kind of just super honest, and I was nervous to post it because I was just saying, like, I don't feel like I'm doing as good a job as I was in the office like I I feel like maybe my career is not going to be able to grow at the same pace I felt like confident about when I was in person. And I think just putting that out there really helps me move past it. And I you know, I got a lot of support a lot of other people saying they felt similarly and I've been able to adjust by that Since then, and just having more instead of always just writing a message to someone, I'll request to do a slack call. And so we will get face to face and I'll share my screen and it can be easier than trying to figure out how to word your problem and get the other person to understand because it is so much easier to just talk some things through in person.

Laurence Bradford 32:24
Oh, yeah, for sure. One of the things I've been doing now I've always like worked remote aliy since 2018 when I left my job to do this full time, but one of the things I do all the time, which is probably very maybe very obnoxious for the people who get them but I do loom videos. Like them it's like a screen share, but I'll do it so it's like my face and my screen and I use I use it pretty much only for work purposes sometimes like like to explain something rather than writing a long email I'll explain through loom or sometimes if I have like someone write me an email with a question like about Should I go to a coding boot camp or something? Sometimes I just record a video and all I do is I just have it on their email and I just talk out loud because for me typing a lot I love to write but I feel like it'd be faster and just easier sometimes to say things for video okay anyway sorry that's like a kind of an aside but yeah loom it's they do have a free plan but then they have I forget what it cost because the they have certain on like usage limitation how many videos you can have in there super easy to share anyway, okay, that that talk about that later. I'm getting I'm getting sidetracked here. But I think what you said about the lacking motivation at first I imagine so many people felt that way. I mean, I know I felt that way. Like when when everything was first sort of shutting down. I was like, I found it so hard to focus at home and really hard to get motivation and like typically that's not really a problem for me like to be motivated to do something but yeah, that first like two weeks or something I just felt really like, Yeah, kind of like blah. Like, I'm not motivated. Yeah. Anyhow, I saw that article that you that you just mentioned, that you posted, either. That's how I found you or shortly after I found you, I came across that but before I reached out that sounds weird, I felt like when I

Caitlyn Greffly 34:18
reached out to you to come on the show,

Laurence Bradford 34:21
that's one of the things I looked at before emailing you and asking you to come on. But in any case, so you're so you've been working from home now for two for like two months, and but you're it's getting better. It sounds like you're you've adjusted a bit.

Caitlyn Greffly 34:35
Yeah, I think I have adjusted, um, I feel like just there's so much communication on our team. And I feel like everyone's got kind of gotten more used to it. So you know, instead of having threads on slack that are super long that no one can keep track of. We'll do a little like campfires and like, just get on a quick call with a couple people to talk something through. And I think I think the team itself has just figured it out better. And then I'm just more used to it. And yeah, I think just adjusting the rest of our lives like, Yeah, not exercising or not getting social interactions as much to me is like very draining. And so now I found ways to get those things into my daily life again, which just helps in general.

Laurence Bradford 35:20
Yeah, creating like structure or routine or trying to replicate, you know, things from before. That's what I've been trying to do at least. Yeah, so another thing that has popped into my head when you're speaking, before you are working in like a very different job, right, like doing sales working at beer industry, what was the transition, like, from working in a industry in a position to then doing software development, like the team dynamics, like was that a learning curve, like, like when you first started,

Caitlyn Greffly 35:50
I was really happy about it. I think I worked remote for five years before landing this job, and I had a lot of people being like, Oh my god, you're gonna have to Go to an office every day, like, you're gonna have that like cubicle life as if it was such a negative thing. But I feel like I really thrive in that situation. And I had a hunch that I would I'd never had an office job before. I never worked in an office a single day in my life leading up to this, but I just thought like that routine and the like, kind of consistent social interaction, and having a separate space to go to, that puts me in more of a work mindset. I felt like, that would be something that I would really like. And I did, and I figured if I don't, then there's plenty of remote software jobs out there anyway. And I can go find one of those. Yeah,

Laurence Bradford 36:41
yeah. So you were 31 when you decided to make this career change. And to me that doesn't feel late, but I know a lot of people listening to this. A lot of people that may be watching this video on YouTube, they may feel like once they're in their 30s or heck even like after college, that it Too late for them to switch into tech. What do you think about that?

Caitlyn Greffly 37:05
I mean, I, I had some of the same feelings. I think that's one of the reasons I chose a boot camp is because I was thinking like, wow, I'm 31. Like, I want to buy a house. And when I was kids at some point, like, do I really want to spend two plus years and like, maybe 40 plus thousand dollars to get a second bachelor's degree, it didn't really feel like it lined up with other goals I had. And then thinking about the idea of just not switching careers. It's like, yeah, it's, it's later than maybe I would have liked but I still have 30 plus years of working ahead of me, like I'm not gonna do what I'm doing for another 30 plus years. I don't even want to do it for another one year so it just didn't really feel like an option to not change and I think it's so much more common in our age group than it is like maybe our parents to change careers and I think tech has made it accessible to do that with boot camps. You know, there's there's some people maybe who have had a harder time trying to transition, but I think boot camps exist for a reason, because you can learn valuable skills there and that employers will hire you for. And so just the return on investment seemed like it was so good, you know, I'd spend six months and $9,000 and I could have a whole new life kind of and, and so I kept my focus on like the bigger picture and I think I always tried to play up when during my interviews and chatting with people that I think my experience, having another career and being a little older would be to my advantage in the new job. So

Laurence Bradford 38:45
yeah, I really like that. And I really like that you said that you still have like 30 plus years of your career in front of you, which anyone transitioning into tech in their 30s or Heck, even like Your 40s you still have 20 years, I guess, depending on when you want to retire when you plan to retire. And I think people that are in their 30s now, you know, I know it gets their their typical retirement age is 65. But Heck, my dad is older than 65. Now he still works full time. He really likes it. He actually works in tech, but and he he, I've mentioned this if people like listen to a lot of these interviews, you've heard me talk about this before, but my dad transitioned into tech. Well, I guess he always worked in tech when he was in his 20s and 30s. But not full time. He didn't get his first like full time tech job until he was like maybe 35. And he's been working in tech and kind of various ways since then. So the last 30 years. Yeah, and I mean, that was way before there was any of you know, boot camps or Free Code Camp, or dev

Caitlyn Greffly 39:50
or Stack Overflow or anything that

Laurence Bradford 39:52
was, you know, helping helping people out along the way. But I guess the point is like, it's definitely possible and if you're unhappy in your career, Like as you are, maybe tech isn't for you, but it's like, you know, another 30 years and other 20 years being unhappy like, is, you know, like, Don't Don't do that to yourself, you know? Yeah,

Caitlyn Greffly 40:12
yeah. People change careers all the time and make it work. So yeah, yeah,

Laurence Bradford 40:16
for sure. Well, we're running out of time. Your I absolutely love talking to you. This was such a good conversation. Before we wrap things up. I wanted to ask though, if you just had any final advice or thoughts for people listening to this? Who are, you know, where you were? a year or a year and a few months ago?

Caitlyn Greffly 40:37
Yeah, I think I would say like, don't try and talk yourself out of it. I think there's so many things that we can say like, this is a risk or what if it doesn't work? I think if you are excited, and you have the passion for it, and you try it out for me, probably more than a week and if something you're interested in then go for it. And it's going to be a good skill to have. And then just try not to be afraid to put yourself out there because I think that the people who might have an easier time finding work at the end are like one of the factors in that is just kind of making those connections and not being afraid to ask what may feel like sort of scary questions of asking someone to connect you with you or give you advice. So,

Laurence Bradford 41:25
yeah. Awesome. That's a great way to end things here. Where can people find you online? Caitlyn?

Caitlyn Greffly 41:32
I'm mostly on Twitter. I'm @thecaitcode. Cait spelled C-A-I-T. Like Caitlyn.

Laurence Bradford 41:37
Awesome. Thank you again for coming on. We'll definitely include that. The links and anything else we talked about here in the show notes. And yeah, thank you again.

Caitlyn Greffly 41:45
Yeah. Thanks for having me.

Laurence Bradford 41:50
Thanks for listening. If you want to recap of this episode, you can find the show notes at From there you can browse through recent episodes or find old favorites using the search icon in the upper right corner.

If you enjoyed this episode, you can subscribe to my show on whichever podcast player you use. For more free tech related resources, tips and recommendations, visit my website and blog at

Tune in again next week for a new episode of The Learn to Code With Me podcast. See you then.

Key Takeaways:

  • Pivoting into a career in software development takes some sacrifices at the beginning. When Caitlyn Greffly was working full-time and learning to code, she had little personal time, but she knew her efforts would pay off. (Click here to learn about other obstacles between you and your career in tech.)
  • Never say no to an opportunity. Being aware of events or people that could lead you to your next job is a skill in itself.
  • Do your research. Because she didn’t have a computer science degree, Cailyn looked for companies that hired people with less traditional backgrounds.
  • Be open to reaching out to other people for help. Caitlyn wasn’t afraid to message people on LinkedIn or Twitter, and that’s how she found shadowing opportunities to learn from others.
  • There are a lot of benefits to having a “cubicle job” where you don’t need to travel for work.

Links and mentions from this episode:

Where to listen to the podcast 

You can listen to the Learn to Code With Me podcast on the following platforms:

  1. iTunes
  2. Overcast
  3. Stitcher
  4. Spotify
  5. YouTube (new for Season 7!)

If you have a few extra minutes, please rate and review the show on iTunes. Ratings and reviews are extremely helpful when it comes to the ranking of the show. I would really, really appreciate it!

Special thanks to our partners

Interview Cake is hands-down one of the best coding interview preparation courses out there! Interview Cake comes with 50+ hours of practice questions and readings that don’t just give you the answer but teach you the right way of thinking about the question. Build the skills to derive the right answers yourself and explain your reasoning. Learn To Code With Me listeners get 20% off here: 20% off Interview Cake

“Every interview I’ve gone through since I started studying your problem set has included a variation of the questions on Interview Cake! There was one problem that wasn’t on here, but I was able to solve it because of the themes you taught. Today I am accepting an offer at a startup in SF!” – Ulises