Find Your Career Advocates: Chris Ling’s Job Search Success Story

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Find Your Dream Job, Bonus Episode 34: Chris Ling

Find Your Career Advocates: Chris Ling’s Job Search Success Story

Airdate: October 5, 2020

Mac Prichard:

This is Find Your Dream Job, the podcast that helps you get hired, have the career you want, and make a difference in life.

I’m your host, Mac Prichard. I’m also the founder of Mac’s List. It’s a job board in the Pacific Northwest that helps you find a fulfilling career.

One of the best ways to get good at job hunting is to talk to people who do it well.

That’s why once a month, I interview a Mac’s List reader who found a job they love.

Our guest today is Chris Ling. He’s a data engineer at Flux. It’s an internal mobility platform that helps employees grow while contributing to the work a business needs to get done.

Chris Ling is an old hand at working remotely. Earlier this year, he found a position with a San Francisco startup that allowed him to do his job from here in Portland.

In a story you can find on the Mac’s List website, Chris says the job search tactic that worked best for him was connecting with colleagues who served as his advocates.

Well, Chris, why do you love your job?

Chris Ling:

Well, I think what I really found out about this job as I started going through my job search, which has been confirmed since I’ve been working there, has been a real focus on advocating for people who are looking for their dream job or looking for the right steps to their dream job. That’s completely meaningful to me. I try to be a very values-oriented person in the way that I approach my career, and Flux just kind of checked all the boxes.

Mac Prichard:

What boxes did it check for you, Chris? What made Flux the outstanding choice for you?

Chris Ling:

Yeah, again, coming from a career development background in law and in tech, I really resonate with the fact that people come from a variety of backgrounds and there’s not this monolithic understanding of what a professional is in any given industry context. And when I heard about the mission and story behind Flux, about how they are positioning themselves to be, within a company, an advocate for the people that are already there and already awesome and to help them navigate that path.

Whether it’s somebody who has a very strong idea of where they want their career to take them, or if it’s somebody who’s in more of an exploratory mode, they are an advocate for that. And that’s the way I try to approach my relationships in my professional life is to really understand an individual and to advocate based on what their needs are and who they are as an individual. Flux has exemplified that since I’ve been working there.

Mac Prichard:

Well, let’s talk about your job search. What was the biggest challenge you faced when you got started?

Chris Ling:

Yeah, when I got started, I think part of it is just brushing off the dust and the rust. I was at the point that I was looking for a job. I was pretty happy with my team and the work that I had been doing but I hadn’t been in that interview mode for a while. So, making that psychological step of saying, “I’m going to commit to this process,” was probably the most difficult part for me. And then figuring out, once I started applying for jobs, understanding what the landscape was like, in terms of what their expectations were, for interviewing a successful candidate versus when you’re on the job and performing. There’s usually a disconnect between how you perform on a day to day basis versus what you can identify or tease out during the interview process.

Mac Prichard:

Was there one thing that was especially helpful for you in getting into that job search mindset?

Chris Ling:

Yeah, I definitely leaned very heavily on colleagues, both within the industry and in previous industries, for a variety of things. Obviously, to get referrals or insights into companies and their needs and what positions were available, but also kind of as a reinforcement. I had gone through these processes in the past where I would interview for a job or in terms of up ramping up, like, “Oh, I do have this long history of professional experience, and I can really lean on that.” So, having them as a gut check as well as being a resource was the major benefit of having people in my corner.

Mac Prichard:

Was that hard to ask for help? For some job seekers, that’s a challenge; they worry that perhaps people don’t want to help others while looking for work.

Chris Ling:

By the time I made this latest job search, it wasn’t but that was a long process to get there. I first moved to Oregon in 2006 to go to law school, and I had no conception of how to network, how to meet people, how to ask for coffee. I also grew up in Hawaii and there, we build relationships because they’re small-town relationships, and you have that casual, small-town relationship. But when I started living in Oregon, it was the fish out of water. I had not built a network here organically, so for me, the barrier was not thinking in my mind, or learning that it was not a mercenary or very selfish way to interact with other people and it wasn’t an imposition.

You have to get to a point where you’re identifying that people are still willing to talk to you even if it’s a professional context, even if it’s in a job seeking context, and people know the experience that you’re going through because, at some point in their careers, they’ve gone through it. I think that was the turning point for me, was realizing that by not reaching out to people, it was really impacting my ability to build connections in my professional space, and that was impacting me on a longer-term scale than just immediately searching for a job. It was just that people didn’t know who I was and people love hearing about people.

We are social creatures, and so, even in a professional context, I think people are willing to give the opportunity to just get to know other people.

Mac Prichard:

How did you learn that lesson, Chris?

Chris Ling:

Well, I graduated from law school and became a lawyer in the recession, and I realized when I assessed where my resources were and I had none, I felt really alone, and I started building my network not because I was just job-seeking, but I was trying to find meaning at a point in time where I felt like I didn’t have any opportunity to show who I was as a professional. So, I volunteered a lot and it was in the course of building these organic relationships with other people, and saying, “Hey, I’d love the opportunity to work for free on this task.” Or help out in this initiative that was happening.

I started seeing those relationships developing, and it was like after I had developed those relationships for a while, it kind of clicked that, “Oh, these are akin to my personal relationships.” They’re just kind of directed more towards the work that I’m doing or this persona that I had in the workplace. So, it wasn’t a very intuitive connection that I made but it was just kind of a process that I made over time that I saw that this benefit happened. Because suddenly, my professional life became much easier to navigate and I had to start thinking about why that was the case.

Mac Prichard:

You work in software now but as you say, you started out as a lawyer. Why did you change careers?

Chris Ling:

Yeah, I think for me, I was going through…I was in my early 30s at the time, and there were a lot of changes going on in my life at the time. I practiced as a lawyer after some odd jobs for a few years in the legal field, but not as a full-time lawyer, and I practiced law for a while, and through that process, I started volunteering with diversity inclusion work with increasing the diversity of lawyers here in Oregon. And through participating with that on the nonprofit side and then eventually working for the State Bar for their diversity and inclusion department, I really got interested in working with stakeholders. Just hearing diverse opinions, understanding needs and experiences that weren’t my own, and it really…there was a creative aspect to wanting to develop programming and create these strategies to help improve the representation in our professional community here that I just really latched on to.

When I started making this transition, I think I was realizing the limitations that I had just being somebody who was communicating on that stakeholder level and developing programs in a very deliberate environment. I just felt like there were other things that I wanted to try to do and try to test and implement, and I wasn’t getting to the point where I was working on…I developed a thing or created a thing and I could iterate upon it. And so, I started thinking about what industries do that, and then I looked at software engineering and my younger brother actually went through a very similar transition from becoming a lawyer to a software engineer, and he was talking to me about what this transition was like and how you were able to rapidly develop things and iterate things and test things out, and that’s kind of the environment I wanted to be in.

I wanted to be able to test a theory or test my intuition or my hypotheses about things, and you can deliver a software product that people can interact with, and you can do it very rapidly and build upon it and see that iterative process. And when I put all of those pieces together and thought, how could I apply this to the work that I was doing, that really excited me and I really wanted the opportunity to lean into that.

Mac Prichard:

What advice do you have for a listener who is considering changing careers?

Chris Ling:

Talk to people. Go on LinkedIn, go on Google, talk to friends, family members, anywhere that you have any connection to the software industry, just start talking to people. Ask people to, in this time, a virtual coffee, scratch their brain, ask any sort of question that you can. When I had started thinking about the transition, I actually had a few colleagues in law that had entered the tech industry. Not necessarily as software engineers, but working in that space, and I did a deep dive. I asked, “Hey, what is your life like now, and what are the things you miss about being a lawyer? What are the things I need to do to prep me into being in this space?”

I randomly, around that time, met the founder of a start-up here in Portland through PDX Parent, there was a great article about him and work-life balance and being a parent and running a startup with his wife, and I sent an email to PDX Parent asking if I could connect with the founder and set up a coffee and just talked and I just said…you know, I talked about how it was really meaningful for me to see somebody who is both doing something that they absolutely love doing but also not deprioritizing their family commitment. I’m a single father myself so that was really important. So, yeah, meeting people in any context just to validate or investigate a little further is my first step.

Mac Prichard:

When you were getting ready to do your search for the position that you have now, one of the things that you talk about in your article on the Mac’s List website is that you brushed up your coding skills. Tell us more about that?

Chris Ling:

Yeah, I had a benefit at the time of a brother who was, at this point, several years ahead. I think it was like, 3 to 5 years ahead of me in this journey, so asking him about his experiences in the interview cycle, because I had only gone through that initial round. Flux is only my second position in this new industry. And just having him say, “Here’s the research that I did, here are the things that you might want to start looking at.” And he gave me recommendations for a few books, he talked to me a lot about, not just coding even, but time management skills when you’re in the interview, which really resonated with me as a lawyer. Because we’re all about time management when we’re studying for the bar exam, so understanding that it was not about just domain knowledge, like knowing what these algorithms are and knowing things about the concept of data structure, but understanding that even if you had that knowledge or didn’t have that knowledge, being able to take traditional time management skills, organizational skills, communications skills, to help ground you was super validating and important for me to understand when I was starting to do my prep.

Mac Prichard:

It’s striking as you talk both about the process that you went through before you left your career and as you prepared for the position that you have now, how much time you invested in research and study, and the curiosity that must have driven that. Talk more about how research helped you both in your career switch and to get the job that you have now.

Chris Ling:

Yeah, I’m a firm believer that doing things explicitly makes you more committed to doing the thing. I think we tend to speculate and there’s a lot of questions. I think I might have heard a previous guest on your podcast talking about, “Should I do something? Or would I do something?” And these speculative terms and I think that when we do that, when we aren’t putting pen to paper, even when it’s purely a psychological exercise, that it doesn’t feel real and we don’t feel committed to the process, and then it feels overwhelming and you get lost in all of the possibilities and all of the permutations of what could happen or couldn’t happen.

For me, grounding things in research was a way of taking things out of my brain and putting them to paper, or in this case, a computer file or whatever, and that kinetic, tactile exercise reinforced in my mind that this was a process that I was going through. And even if it was incremental, even if it was like, I looked at one job posting today and then I wrote some notes down, or I only studied and did one practice coding problem today, but I did it. You know, that was a step that I had taken, and that was way better than just being wrapped up in my brain and just thinking about the possibility of studying or the possibility of looking at this job posting.

It made things real and that was what really motivated me to keep going.

Mac Prichard:

Your job at Flux has always been a remote position. Did you set out, Chris, to find a job that would let you work from home?

Chris Ling:

I think indirectly, maybe not necessarily from the perspective of wanting to work remotely, but wanting to work with companies that were doing exciting things but not having…and then minimizing my ability to leave the state. I’ve been in Portland now for over 14 years, since this August, and I love Portland. Portland represents so many things to me in terms of its values and its beauty that I didn’t have growing up. It was a different kind of beauty. I’m from Hawaii originally, so people get a little weirded out by the fact that I say I love Portland, and they compare and contrast it with the beaches of Hawaii, but Portland is different to me because it’s meaningful to me but it’s also something that I’m drawn to.

To answer your question, I was seeking an opportunity that was a challenge, and disproportionately, unfortunately, the companies that are in the tech industries aren’t in Portland, and Portland’s done an amazing job in attracting tech companies in the last 5 to 10 years. I, in fact, remember, Mac, that you gave a presentation at, I think it was Vacasa a year…or maybe it was like 4 months before I made the switch, to go into coding boot camp, and you were talking about how we were on year 3 of a 10-year cycle of just explosive growth in the tech industry. We still have a lot…and it’s grown so much since then, but like, I was looking for places…I’m still looking for those opportunities where I wanted to work on amazing things with a lot of data and a lot of interesting problems, and unfortunately, we’re not at that critical mass yet but I feel like we’re getting there.

That’s what directed my search outward and that meant, to stay in Portland I would have to find a remote job.

Mac Prichard:

We’ve made a lot of progress but we’re starting from a small pace. We’re certainly not San Francisco.

Chris Ling:


Mac Prichard:

Well, when you were hired by Flux, did much of the hiring process happen virtually? Again, this was pre-pandemic.

Chris Ling:

Yep, virtually everything except the last interview was done via phone or via video chat. And it was like, I met with the CTO, I met with the senior engineer and the COO, and then after I had gone through, I think three interviews, they gave me an exercise to work on, exploring data, and then I met the rest of the team in person in San Francisco for the final interview. And then for those who were in New York and in Portland called in, so everybody in the company, I’m employee number 10, and so everybody in the company was in on the interview at the time.

Mac Prichard:

What’s your best advice for a listener who is about to start on a virtual hiring process? What worked for you, Chris?

Chris Ling:

Yeah, definitely find those resources, first of all, find a mentor, find those resources online. I actually volunteer quite a lot in the tech community; if you find me on LinkedIn, hit me up. I’ll talk with you about what the process is like. Definitely, to the extent that you have, anybody who is willing to sit in on a call, like just practice being able to communicate out loud, sort of the elevator speech but also presenting, maybe it’s a project or talking about something that you’ve worked on. Do it with someone else, and that’s really hard because you can’t meet with them in person, but I will say the same thing that I talk about when being explicit about the things that you do. You need the opportunity to have the words out, to hear whether or not you sound credible, to refactor, and to improve upon, how you’re presenting information and how you’re conveying who you are.

The only way you can really do that is by communicating with people. Again, if you can schedule people to video chat with you or even to audio chat with you so that you’re going through that interview process and feeling it out. It becomes more real and that will help you, even in this virtual environment.

Then on the more practical side, I always recommend that…a lot of the tech interview processes, before COVID, were centered around things like, maybe you’re whiteboarding something or writing something on the fly, I would say practice those things or start utilizing tools where you already have the ability to sketch something out- a workflow or draw up a diagram. Have those things in your back pocket and maybe even pre-do some of those things so that you feel comfortable interacting with technology as you’re having the interview because that’s a big roadblock, is you get frustrated because maybe the platform that you’re using to write down code suddenly has a delay, and that just builds all of these stresses upon stresses. So, the more that you practice on those things before the interview, that’s a big thing in the virtual environment that I would recommend.

Mac Prichard:

Well, finally, Chris, what’s your number one job hunting tip?

Chris Ling:

People, it’s always people. I used to be, back when I was young and naive, I used to think, it’ll be the work that I did and the grades that I had. You know, like all of these things that are on your resume, these “objective deliverables.” I am now wiser and older, and I know that that is definitely not the case. Relationships take a lot of the edge off of an interview process.

Relationships will open your eyes to opportunities that you wouldn’t have considered and will be the foot in the door and will be the advocates for you, either directly or indirectly. So, even before you start, and especially before you start the interview search, build strong relationships with people. Build meaningful relationships with people. They’re going to be in your corner, they’re going to have your back, but only if you’ve actually developed a relationship, as opposed to building a relationship solely to get ahead in your next job search.

Mac Prichard:

Well, thank you, Chris, for sharing your story. To learn more about Chris Ling’s job search, visit

And check out the Mac’s List website for dozens of other success stories.

On the second Friday of every month, we add a new interview with a Mac’s List reader who has found a dream job.  Go to

In the meantime, thank you for listening to today’s bonus episode of Find Your Dream Job.

If it’s been a while since you did a job search, you might feel a bit rusty. And that’s completely normal. One of your first priorities should be identifying the people who will help you work through the process, whether that’s through introductions to others in your chosen industry or simply standing by as emotional back-up. On this bonus episode of Find Your Dream Job, Chris Ling and I talk about his move from lawyer to data engineer. Chris shares how networking with others and practicing the skills necessary for his new career helped him achieve his career goals. Learn more about Chris’s career history below in this installment of our Success Stories series.

What do you do for a career? Who do you work for?

I’m a software engineer with a primary focus on back-end issues related to the ingestion, transformation, and visualization of large amounts of data for stakeholders. I also have my hand in some level of infrastructure and DevOps stuff as a necessary part of fulfilling the above responsibilities.

I just started working remotely for Flux as a data engineer at the end of February 2019. It’s a San Francisco-based startup with teams in SF, NYC, and PDX, and it focuses on applying data science and new tech to redefine how individuals’ unique expertise is understood, conveyed, and matched to work opportunities within a company or organization.

Before that, I was a software engineer for a little over a year and a half at Vacasa, a Portland-based startup in the vacation rental management industry. I worked on pipelines and visualization tools to facilitate data science and analysis related to setting vacation rates for Vacasa owners, using historical vacation market data.

How long did it take you to find this job?

I had been pretty selectively looking for new opportunities while at my previous position, so with that as context, probably around four to five months of targeted applications.

How did you find your job? What resources did you use? What tool or tactic helped the most?

Like most of the positions for which I applied, I heard about this position through a colleague in the industry who knew I was looking for new opportunities. In terms of my job search in general, I used a combination of resources:  colleagues/referrals, recruiting platforms (LinkedIn, AngelList, Mac’s List, etc.), and a couple of recruiters who reached out to me on LinkedIn.

I’d say the most effective tools or tactics in my job search were (1) having developed a network of people who knew me and could vouch for my professional skills, both as an engineer and in my prior career as a lawyer and diversity professional; (2) going through the sometimes painful process of honing my engineering skills through short-form and long-form coding exercises (LeetCode, books); and (3) self-reflection about specific things I’ve learned and where I could improve from projects I’ve worked on in the past.

What was the most difficult part of your job search? How did you overcome this challenge?

I actually transitioned very recently into software engineering in 2017, leaving a career in the law to attend a Portland coding bootcamp, the Tech Academy. While bootcamps are a great way for people from non-traditional backgrounds to enter the software industry, the practical focus of those programs meant that I didn’t have a formal, academic background in computer science.

I ended up applying to at least one company where the interview criteria was heavily focused on having a strong, solid background in computer science topics around algorithms and data structures, so I spent a solid two months building those skills into muscle memory, which meant hours upon hours of coding challenges, white-boarding exercises, and mock interviews. The intensity of that schedule was definitely the most difficult part of my job search, but a great benefit from going through that gauntlet was that it helped commit better coding habits into muscle memory, and made other interviews seem less daunting by comparison.

What is the single best piece of advice you would offer other job-seekers?

Build organic relationships with people in your industry and nurture them, regardless of whether you are looking for a new job at the moment. Your peers will play an outsized role in getting your foot in the door for great opportunities, and the more that a colleague can get to know you over time, the better they can advocate for you, directly or indirectly, when you’re exploring the job market.

Meet-ups and events you’re interested in are a great way to start those relationships, but I personally love just asking someone to a coffee or lunch to get to know them on a more focused, intimate level.

I’m particularly an advocate of building relationships by volunteering your time within your professional community. I currently perform short mock interviews and longer one-on-one career advising sessions with coding bootcamp graduates. I think these sessions provide new graduates a constructive environment where they can hone their interview skills and ask honest questions about the transition into a new industry. It also gives me the opportunity to view interview questions through the lens of an employer to more effectively understand and appreciate the interview process as a whole.

Why do you love your job?

I’m still in the on-boarding stage of my new position, but what attracted me to the job and what I think is validated by my short time here is a culture of trust, curiosity, and a desire to work on challenging problems. I work well with a small group of smart, thoughtful, and empathetic people, and I think I’ve been fortunate enough in the last few jobs that I’ve had the chance to work with people who embody those exact traits.

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