The Career RelaunchPodcast

Episode Interview Transcript

Teaser (first ~15s): I just said, ‘I want to be a teacher forever, so I’m going to go do that right away.’ You can imagine sort of my head down, focused on just achieving these milestones without actually picking my head up and thinking, ‘Is this really what you want to do?’

Joseph: Krishelle, thanks so much for joining me here on Career Relaunch. I’m really excited to hear your thoughts on how you can apply design thinking to your career and the steps you took to shift from teaching to the tech industry. I was wondering if we could start off though by having you tell us a little bit about Dropbox and your role there.

Krishelle: Thanks, Joseph, so much for having me. I’m super excited to share my experiences from my own personal career launch. I’m currently working at Dropbox, which is a cloud data company where we store your data inside the cloud so that you can access it from anywhere on any of your devices. The role that I’m currently in is I’m a SRE or Site-Reliability Engineer. I’m sort of a hybrid between a software engineer and a system administrator. I’m focused on making sure all the systems that Dropbox depends on are reliable and that Dropbox is always available for our users. I utilize code to automate all the processes to make sure that those things happen.

Joseph: I know there’s a lot of different roles there at Dropbox. How did you decide on becoming an SRE versus other sorts of roles there at Dropbox?

Krishelle: Frankly, I was really looking for a really great running opportunity. I landed in the SRE role because the program was designed around bringing up people who were making a career change as apprentices in this type of role. I was really looking for something that would allow me to learn and be engaged in design conversations. Also, at Dropbox, we’re constantly trying to make our product better and trying to make it more reliable, more available and just create a better user experience for our users. That really forces you to be engaged in these critical conversations around problem solving and design. SRE allowed me to do that from all different avenues.

Joseph: I know, Krishelle, you haven’t always been a site-reliability engineer. Can you give us a glimpse into your former life as a high school teacher back in San Diego?

Krishelle: Prior to me becoming an SRE at Dropbox, I was teaching for about six years. Five of those years were in San Diego, California. When I went into college, I immediately pursued the route of becoming a math teacher. I had always been very strong in math. Both my parents were math majors. I thought, ‘This is the right path for me,’ and so I ended up pursuing that route.

The issue with that is that I don’t think that I spent a lot of time thinking critically about whether that was a job I wanted to do. I didn’t know a lot about it. All of us go through school. We all see teachers work. We don’t always know everything that goes into the profession of teaching. Although I had seen my mom go through it, most of my experience with her was watching her as an administrator, so I didn’t always have a clear view into the classroom.

As I got to the end of my program at university, typically when you’re finishing a credential program, you go into what’s called student teaching. That’s like an apprenticeship for teachers where you work under a master teacher and you learn the ropes.

As I’m in this program, I’m thinking, ‘This is pretty challenging. I can probably do it.’ I wasn’t sure if it was for me, and I think that’s pretty typical of new teachers. I think a lot of new teachers get in there, like, ‘This is very hard. This is harder than I expected.’ Typically, other teachers will tell you, ‘Give it some time. You’ll get the hang of it. Give it a couple of years, and you’ll really know whether this is the right place for you.’

Joseph: Was there anything in particular that made you a little bit uneasy about doing the teaching that you’re doing?

Krishelle: Part of the reason that I ended up leaving was that teaching itself, in addition to this idea of wanting to grow myself, is that it was really exhausting me. At the core, I wasn’t getting everything out of it in order to really feel fulfilled.

In that instance, I was able to tell that because my behavior was demonstrating it. I started to do a lot of side projects. The little free time that I did have, I would take on these little projects – things like event planning and cake decorating. I ended up taking a coaching position at my job, and I think I was doing that to sort of mitigate this feeling of lack of professional and personal growth. I’d say, ‘I’ll just take on all this other stuff. Maybe I can find it there.’

Eventually, that really led me to just be very exhausted, and I ended up in a position where I took a coaching position, and I made a commitment that the expectation was that I do that for a very, very long time and end my career in this particular position. I think that was a very important moment for me because I really had to confront the fact that I wasn’t getting everything I needed out of that career. That was the defining moment for me where I decided that it was time to make a change.

Joseph: What was the difference between this point of exhaustion and some of those mental rumblings that you had been feeling before?

Krishelle: I think at this point, the side projects weren’t even doing it for me anymore. They were not even helping to make me feel fulfilled. Those too were over-exhausting to me, and so I really felt this pull to see what else is out there. I was confronted by the fact, towards the end there, that I hadn’t really thought critically upfront about the choices I was making to go down this path. I knew that I needed to take more time to think about it, and I think when you get to that low point of exhaustion, you start to question all your choices. That’s sort of what happened.

Joseph: One of the things that you had mentioned—I think it was in your webinar you gave for women who code—was that you mentioned having your head down, focused toward achieving your goal. What exactly did you mean by that?

Krishelle: Once I got into university—I went to the University of San Diego—they asked you to declare a major. I immediately declared math major with the intent on becoming a teacher without even really thinking about it. I was very determined during that time to finish both my credential and my double major that I ended up getting in four years. At that point, I sort of put my head down, and I really focused on reaching the end goal of you will get your degree in four years. It will be in math and Spanish with a teaching credential, and then you will go on to teach. That was what I was focused on.

I ended up going on and getting a Master’s because I knew, within the teaching profession, you can actually move up the pay scale if you have a Master’s. So I just said, ‘I want to be a teacher forever, so I’m going to go do that right away.’ You can imagine sort of my head down, focused on just achieving these milestones without actually picking my head up and thinking, ‘Is this really what you want to do?’

Joseph: I’ve definitely been there myself, Krishelle. On the one hand, a goal can be really great, but then on the other hand, it can be a little bit limiting, and it can prevent you from being able to see the other options that are out there.

I read a couple of your blog posts on Medium and the Hackbright Academy blog. One of the things that struck me was how methodical you were about your approach to shifting from teaching into what you’re doing right now. For the rest of the conversation, I’d love to dig in a little bit more into specifically how you applied design thinking to your career change. I know that’s something that you’ve talked about before. Could you just walk us through how you applied design thinking to your life and career?

Krishelle: The idea of design thinking is that you identify a problem, and then you move on to develop several prototypes that address this key problem that you have. Then you go through this process of testing those different prototypes and keep iterating on the one that is ultimately chosen. This is a process that’s actually used when you’re designing anything, from a coffee to a computer mouse.

The problem that I started with was this idea that I’m not fulfilled as a teacher, and so I started to think about, ‘What do I like about teaching? What don’t I like? What are the other things that I’m doing, addressing that teaching maybe is not? What are the central themes about those things that I can pull out and try to make into a career for myself?’ Ultimately, I sort of reframed that problem statement into, ‘I need to find a career where I can use design,’ because designing was very key to all of those different activities I was doing, ‘where I could problem solve on a day-to-day basis and where I could have impact.’

There’s this really fantastic book called Designing Your Life. If there are any folks out there that are looking for some more strategies on how to think through this process, that’s a really great resource for you.

What I ended up doing after honing in around this problem statement of looking for design and problem solving and impact, I went forth and tried to create a list of what they called prototypes in the design world where I say, ‘These are the different careers that might be interesting to me. Let me explore them a little bit.’ That’s the sort of testing part of this whole process.

Some of the careers I looked at was computer animation. I grew up in SoCal. I was really into watching animated films and Disney, so I thought maybe I could go into that realm and become a computer animator because that blended technology and art and creativity and whatnot. I thought about that and took an animation class. That was my way of testing whether that was going to be an appropriate direction to go, and I ended up not liking that. It wasn’t for me, and so I pivot to another prototype.

As I mentioned before, I thought about doing some teacher training, I thought about going into tech as a product manager or an engineer. The way that I went about testing those three is I just started to have conversations with people. I started to reach out to people in EdTech or just in tech in general, different employees, CEOs, things like that. A couple of people that I came across were engineers within tech, not necessarily EdTech but within tech. They started to tell me about how they got to work on different projects, and they were always constantly engaged in this idea of design thinking and problem solving.

Ultimately, I learned about a boot camp called Hackbright Academy, which is a software engineering boot camp. It’s three months long, and it actually allows people to make a career change into tech to become an engineer at the end. That was ultimately the route that I chose, because when I went to speak to some folks at that school, I really felt that those thing I was looking were really going to be something that I would get out of an engineering career.

Joseph: One of the other things that you had talked about in some of the articles that I read that you had written, this part where you’re talking about testing prototypes is to test enough prototypes, and wait till you have that moment when one of them just speaks to you. Can you just explain how you determined whether something was speaking to you or whether it was just something that you kind of thought was interesting?

Krishelle: I had heard about this school called Hackbright, and I went to an open-house that they were hosting. I go in, I sit down, there’s a bunch of other women there, it’s an all-women school, and they had a panel. On the panel was a teacher. It’s like everything I had said to everyone in my life about what I was looking was coming out of this teacher’s mouth in this moment.

I think it’s important, as folks are out there and considering this career change, that as you’re talking to different people, if something jumps out at you, really piques your interest, really engages you, you engage in an activity that time flies by and you don’t even notice, to really pay attention to that, because that is something really speaking out to you that this is a path worth looking into or possibly pursuing long-term.

Joseph: This process you’re describing of applying design thinking to your career sounds very patient, very rigorous, very methodical, and it sounds like it really worked well for you. At the same time, it also sounds like it requires a lot of discipline and hard work. Was there any sort of tool you used to help you stay on track to keep track of this design process applied to your own career?

Krishelle: I am sort of a type A person in the sense that I like to write all of these ideas down and come up with a framework for myself. I actually wrote a blog post that maybe we can link to later on.

Joseph: I saw that. That’s exactly what I’m referring to.

Krishelle: It’s where I described how I thought about these things and how I broke it down.

In reference to a particular tool, I would say one that I really make use of still today is Trello because I think it really allows you to encapsulate all of your different ideas into small cards that could then be moved around and edited. I think if you’re someone who’s actually making a career change, and you’re going through the job search process, you can use it to really have a good view. It’s almost like a board to look at where you can see your progress right in front of you.

Joseph: That’s a really good segue way into how you landed your job at Dropbox. I read your article on how you designed your career change on the Hackbright Academy blog and how you really hustled to land your job at Dropbox. One of the things that you mentioned in there was about asking questions and asking intentional questions. Can you just explain what you meant by an intentional question?

Krishelle: I had done all of this work of designing my career blueprint and really thinking critically about what I want. By the time I was in front of the folks that would actually give me an opportunity to pursue that, I could tell my story very well because I have thought through it. I had really done the work to understand what I was looking for, and I could communicate it very effectively.

I ended up meeting a woman who worked at Dropbox. She was the Engineering Manager, still is, and I just started talking to her about what she does. What I found is that a lot of the common problems she faced, I had faced in my own project, and so we go in this really cool narrative. After she and I had communicated over email several times, I saw her at a different event. When I saw her, I realized how impactful she really was as a female leader in tech, which you don’t see very often frankly. I was just really impressed and inspired by her.

So I just decided to ask, ‘Would you ever take a junior person?’ because typically, when you come out of these boot camps, you’re at a very junior level. She happened to say, ‘Oh, we’re doing this program with a boot camp, and it’s going to be great,’ and then she sort of just walked away. That was an important moment because I went home and I thought, I should asked to be considered because otherwise, no one’s going to hand me this type of opportunity.

I decided to send her an email, and I said, ‘Hey, I’m really inspired by you. I would love to work for you. I’ll do whatever it takes. If there’s ever an opportunity, please let me know.’ Because I stepped out to ask that very poignant and audacious question, she was so impressed by that that she ultimately invited me to come and interview. Eventually, I was very lucky to land the position.

Joseph: What’s one thing that you’ve learned about what it takes to make a career change into the tech industry that you wished that you had known before?

Krishelle: The biggest thing is your network. That summer I talked about earlier where I spent the entire summer just pushing out my resume, I was not successful because I did not have a network here. The most important thing and choice that I made was to move up here and start building my network. I think it really does help when you know someone who can vouch for you and say, ‘Yeah, she’s really awesome. She would be a great addition to our team.’ Unfortunately, that’s the tough part because a lot of people may not know anyone at a particular company or within the industry.

It really is, at the end of the day, a lot of the times, about who you’ve connected with or what people know about you, whether it be through someone else or via what you put out into the world online. That’s something that I put a lot of emphasis on, and I focus a lot on: just making sure my online presence really shows who I am as a whole person and what I care about, because sometimes, it may not be about who you know, but it may be about someone seeing something that you did or you wrote about, piquing their interest and ultimately leading you to an amazing opportunity.

Joseph: I think that’s really important. Again, I know you touched on that in your article: just making sure that the message that you convey is consistent with your online narrative. I think that’s what you are alluding to there.

Before we go, I also wanted to touch on a project I know you’re really passionate about, which is The Bethune Project. Can you wrap up by just telling us a little bit more about that?

Krishelle: The Bethune Project is this amazing project that started this past year during Black History Month, and it was actually started by the great-grandson of Mary McLeod Bethune, who in the United States was a civil-rights activist. One of the things that he noticed was that there were a lot of negative imagery around African-American men in the United States. What he wanted to do was really turn that over and offer people a repository or collection of positive images of black men.

If you go to TheBethuneProject.com or you go to TheBethuneProject on Instagram, you can see this collection of these amazing images of black men. It’s a photo project. I encourage everyone out there to check out the project. Follow it and just support this amazing work that he’s doing.

Joseph: Thanks so much for letting us know about The Bethune Project. We’ll definitely include a link to The Bethune Project in the show notes along with a link to your articles, which I think do a really great job of walking people through exactly how you made this career change, the tools you used, the steps you took, how applied design thinking to your career search. In addition to that, where can people go to learn more about you?

Krishelle: They can go to Krishelle.me. That has all the links to all my other social media sites. Feel free to follow and engage in a conversation with me. I’d love to chat.

Joseph: Fantastic. Krishelle, I really admire your methodical approach to taking control of your career, and I really just wanted to thank you for telling us more about your life as a site-reliability engineer, how can apply design thinking to your career, and the proactive steps you took to land your role at Dropbox. I hope things continue to go well for you there.

Krishelle: Thanks so much, and thanks for having me, Joseph. This has been awesome. You are really someone who really helped me to make this choice and gave me some of the tools that I still use today. I really appreciate all the work you’re doing.