Learnings from an 18-month job transition in tech

Overview

This article recaps my journey between full-time tech jobs from September 2022 through March 2024. It was a period of professional transformation that included rapid upskilling in technical and leadership domains. I learned a ton. There were many growing pains. Now that I've settled into the new role, I’m happy to share stories and takeaways with you.

Note: I recognize that I am privileged in various ways. There are things I was able to do, risks I was able to take, that many don’t have the luxury of. I recognize the gap, as did one of my peers when he said, “if finding a job was that hard for you, what hope is there for the rest of us?” And yet everyone’s journey is unique. I invite you to take from these stories what is beneficial for your growth.

Decision to quit: Sep 2022

In September 2022, I made the decision to leave my job as a lead research scientist at Analog Devices. I had been there for 6 years and realized that my growth trajectory was far out-pacing what the group could facilitate. I tried for 8 months to find a way to stay because there were many things I liked. But it just wasn’t happening. The move took many of my coworkers by surprise. One said that he “triple-taked” when he saw my announcement e-mail. Others saw it coming a mile away.

I exemplified the challenge facing large corporations when it comes to retaining talent. The prevailing bureaucracy acts so as to limit the learning experiences employees can have. This “coercive learning” (Coutu, 2002) is administered according to “business need”, which includes managers’ personal agendas. My departure signaled that I was willing and able to take on risk to accelerate my growth.

Detox: Sep-Nov 2022

Working in a traditional corporate environment takes a toll on many employees. A week after I left, a series of memories floated up into my conscious mind for several weeks, spaced 3-5 days apart. I processed each memory in turn, fully experiencing the feelings that I had repressed at the time for the sake of professionalism and to keep survival anxiety at bay (Coutu, 2002). I used a variety of techniques to more quickly digest the memories: conversation, journaling, meditation, long walks, and ideating around my personal and professional visions. It was an extremely productive albeit stressful 6 weeks.

Discovery: Nov 2022-Jan 2023

I initially felt unsure about next steps, so I hired a career coach for 6 sessions. He was instrumental in non-judgmentally evoking insights within me. Through those sessions I realized that my preferred way of connecting with others is the way my coach had connected with me.

I read up on workplace “coaching cultures” (“High-Performing Organizations Have Coaching Cultures”, n.d.) and loved the sound of it. I wanted to level-up on all of it, so I looked into coach training and signed up for a 6-month program starting in January.

One day my wife mentioned the field of organizational psychology. It sounded well-aligned with my leadership development goals. I eventually became enamored with it and signed on for Harvard Extension School’s (HES) Masters program focused on Industrial-Organizational Psychology. While all of this leadership development was happening, I also started planning out large-scale software projects that would further my skills as a data scientist and software developer.

It was all very exciting, but also stressful because of the constant lapping of uncertainty against the shores of my mind. Am I making the right decisions? Is this a good investment of my limited resources (time, energy, money)? What do I focus on? How do I stay motivated? It would take me another year to more fully appreciate the entrepreneurial mindset that munches on VUCA¹ like it’s a snack food. It was all new to me at the time, and new = stress.

Growth: Jan 2023-Aug 2023

Coach training was beautiful, as were org psych classes. I felt reborn. In my last workplace, no one had explained the value of these things. Technical contributors who pursue this knowledge and these skills risk backlash. I’ve come to understand that this is a strategic and fear-driven response of management to employees’ natural desire for growth within a traditional corporate culture². Delving into the psychology of individual contributors, teams, and the workplace was incredibly refreshing.

The blog you're currently reading was my first live (static) web app. Following that was an end-to-end, full-stack ML software project. I got it up and running, piece by piece, struggling through this tutorial and that debugging session. I built a frontend web app and used it to annotate data streamed 24/7 through a microphone into a PostgreSQL database living on an Intel NUC.

The website is still live today, served with Node.js, Express, Nginx, Pug templates, with Python tools split into packages covered with tests and logging, readmes, and CI pipelines. Real software development, not a pile of undocumented research code. After that, I gobbled up learnings on containerization and cloud tools. I was getting more and more interested in backend software infrastructure.

Then things got busy with two classes: “leadership perspectives” and “negotiation and conflict resolution”. Each one was a full semester packed into 3 weeks with only a 3-day weekend between them. Exhausting, but totally worth it. I finished coach training and started the ICF certification process immediately after. That’s when I felt ready to start interviewing more seriously and find a job. It had been a year since I left ADI. Time to make it happen.

Interviews: Aug 2023-March 2024

A new kind of stress came crashing down. I started applying to jobs on LinkedIn and putting my resume on job boards. It was a blood sport. My inner critic had all sorts of nasty comments to slingshot my way.

“Wow, that’s all you did in the last 12 months?”
“You think you can get that job?”

Fortunately, I had skills in dealing with inner critics from coach training as well as peers to lean on across multiple coaching circles. They helped me work through inner conflicts as I helped them with theirs. This definitely made things more manageable.

Overall, though, the process was just as disappointing as dating. Over the 7 months I was actively interviewing, I applied to about 300 job postings and did 40 interviews. Roughly 70% of applications were black holes where I never heard back. Another 25% were generic rejection e-mails I received between 2 days and 4 months after I applied. The remainder were invitations to schedule a phone screen, half of which led to immediate rejection. The funneling effect was dramatic, leading to a 2% conversion rate to serious job prospects.

In those 7 months, I got to a final round interview 4 times. Google and Meta’s software and ML engineer positions were options, but I wasn’t willing to leave the Boston area and I was told by in-house recruiters that their Cambridge offices didn’t have openings.

Interview experiences

The job boards gave me experience with interviewing and helped me to hone my professional vision. However, it was a networking connection that got me a job. The networking approach is what entrepreneur and consultant friends had all told me was the way to go. It’s also what the authors of “Design Your Life” recommend (Burnett & Evans, 2016). See chapter 7, entitled “How Not to Get a Job”, for an in-depth explanation of why job boards are black holes. On that note, here are a few memorable interviews.

1. “We aren’t hiring for that”

My first final-round interview was with a startup here in the Boston area. They advertised the role as “data scientist”, which is what I was looking for. I had fun completing the take-home coding interview and had a good conversation with the CSO (chief science officer) about technology and workplace culture. We talked about the overlap between the MBA he completed and the MLA I was currently in. I was impressed and went into the virtual technical presentation to the founders with optimism. I wound up disappointed.

They were on their laptops most of the time and after I mentioned “healthy collaboration” during the Q&A, my would-be manager asked me what I thought of competition. Being a newly-minted IO psychologist of sorts, I said “well, if it’s collaborative and involves driving each other forward to accomplish more, I think it’s great. But if it involves undercutting each other and other unhealthy behaviors like that, I would say it’s not a good thing.” He said, “what about competition with other companies?” I said, “oh, well that reinforces my point because you need a strong culture to drive your group’s competitiveness in the market. That’s why you want to cultivate leadership.” The CSO then said “we aren’t hiring for that” in a disappointed tone.

It was at that point that I realized a few things. My would-be manager didn’t understand the interaction between culture and collaboration, and the CSO didn’t understand the difference between management and leadership (Zaleznik, 2004). On top of that, the founders’ questions in the Q&A revealed that it wasn’t a data science position after all, but a hardware simulation job. So they must not have known what a data scientist is, either.

It was a good warm-up that boosted my confidence. Also, they gave me feedback when I requested it, saying that they rejected me because I seemed more like a software engineer. It was the one and only time I would ever get direct feedback after an interview. I would later learn, in a course on HR management (Dessler, 2019), that giving feedback to candidates opens a company up to unnecessary liability. That’s why standard practice is to send a generic rejection e-mail and subsequently ghost the candidate. Yet another sign that these guys didn’t know what they were doing.

2. “Did we prepare for this meeting?”

The second final-round interview I had was an on-site, which is an in-person series of interviews at the company’s office. It was a software job at a startup. They seemed friendly when I arrived, got some snacks in me right away (not a bad move), and then started the interviews. The heads of engineering and software sat down with me and turned to each other to say “so yeah, uh, did we prepare for this meeting?” They laughed and waddled their way into questions about my background. I played along for the time-being.

Following that was a meet-the-team session where I found myself talking to 3 NCGs (new college grads) about their work. Seemed like a nice group. Then head-of-software started asking me coding questions.

He had two questions that I solved in a few minutes each. They were examples of unintuitive Python-specific bugs I had seen before. There were no algorithm, data structure, or system design questions. I was left wondering where the rest of the coding interview was. He also mentioned multiple times that “the work is rudimentary” and that they “find it hard to hire software engineers”.

Then came my conversation with their HR rep. It was time for some serious questioning. Not from her, but from me. I knew enough at that point to recognize a rotting culture. Their Glassdoor reviews had also raised red flags.

HR rep encouraged me to address all of my concerns out in the open, so I leaned in. “I’ve learned about power dynamics in the tech industry and how people can feel pressure to say yes to management. What happens here when someone disagrees with the CEO?”

She looked startled by the question, understandably. She assured me that they don’t tolerate disrespect, and that the CEO wants everyone to feel like this is their playground. At the same time, everyone needs to get their work done. Her surface acting was commendable (“Emotional Labor”, 2024).

When I got home, I sent her a follow-up e-mail. I wrote about how I really liked the conversation she and I had but that her colleagues left me thinking that this wasn’t a high-quality position. I explained why in detail and then suggested some avenues for job enrichment, which is HR-speak for what I would like to see change in the job description. She had asked me about this before and I had promised to let her know. Generic rejection e-mail.

3. “I guess it’s a sleepy day.”

The third final round interview was with a biotech startup that seemed like a great fit. I felt like I could communicate well with all the managers I spoke to. Their recruiter was very professional all the way through, very organized. After several one-on-one interviews, they brought me in for the final round, which was a 7-hour on-site at their office.

The full-group, collaborative problem-solving session was a bit slow at times and three members did the majority of the talking. It prompted one of the managers to say, “I guess it's a sleepy day.” I kept it light, saying “well it is a Friday” with a smile. Despite the compulsory awkwardness in a room of young engineers, I thought it went swimmingly. I felt accomplished on the Uber ride home.

After the Thanksgiving break, they asked to talk to my references, marking the pre-offer stage. A week later, I got a generic rejection e-mail. I called my references to check in with them and everything sounded normal. I have no idea, to this day, why they said no. I asked for feedback “to support my job search and professional development”. Nothing.

Other anecdotes

Here are some honorable mentions. Like when I asked in a third-round interview where I would work from, and the head of data science unmuted himself to say, in a low voice, “I think…office across from MIT…Sundays”, leaving others on the call confused. I responded, “so fully remote, then”. “We’ll get back to you about this.” Generic rejection e-mail. Or the time I felt self-conscious about my tenure at Analog when the guy interviewing me said, "wow, you worked there for six years, what happened?" Generic rejection e-mail.

How about the time I was passed along through a recruiting team to someone who asked me a long series of questions, half of which were answered on my resume, only to get to "do you have experience with recommender systems in the retail industry?" I said no, and she said, "well this client has a hard requirement on retail industry experience". Their team lead got an e-mail from me afterwards with feedback on their process. Or the time when a freelance recruiter said "they're looking for someone who can be a player-coach" and I replied "I'm very qualified for this position and I'm literally a trained coach who works with engineers." We agreed that it would help if I wrote a letter to the head of software making my case. No luck.

Then there was the time I had a great series of interviews with a company I connected to through a reputable recruiter. It was a contract-to-hire software position in the veterinary medicine space that excited me. The technical interview went well and, after passing my references along to them upon request, the recruiter told me it’s a no. This time it was because, yes, they liked me, but they found someone with veterinary industry experience. I related the story to a colleague who said, “how the f**k are you supposed to compete with that?”

Hope and hopelessness

Throughout these interviews, my emotions went up and down quite a bit. I did my best to reframe rejection e-mails as a sign of effort and progress. I also found hope in getting further in interview processes. But the months were going by with no clear sense of when my effort would convert to even a single offer. People like to talk about getting multiple offers so you can negotiate compensation. But despite my many privileges, this was one that continuous waves of layoffs across the industry wouldn’t allow.

The burden of non-stop rejection and delayed gratification (especially of an income) was surprisingly constant and heavy. I went through cycles of giving up or feeling numb and then after a few days getting back on it. Through it all, the support of fellow entrepreneurs and job-seekers made a huge difference. It was yet another reminder of the resilience that comes from community.

My wife in particular was incredibly supportive, able to crack tough eggs in my mind with a few well-placed words. She suggested leaving my last job, talking to a career coach, studying org psych, establishing a better work-life balance, and much more. Despite my career transition being hard on her, she was a source of strength for both of us. Married men: always consult the wife.

Shift towards networking

Once 2024 came around, I felt like I understood the interview process well enough and needed better ways to generate high-quality leads. So I started going to in-person networking events. They were exhausting and anxiety-provoking at first, but effortless and supportive soon after. Interestingly, I wound up connecting with many coaching clients that way, and it led me to more fully embrace ambiguity and all that it had to offer.

I also reconnected with former colleagues with whom I could do interview prep, discuss ideas, explore opportunities, and so on. I buddied up with one of them on technical development and job search. He eventually referred me to a health tech startup.

Landing: March 2024

I had a call with the CEO of the startup and it was a lovely conversation. They wanted a strong leader with broad expertise. Then I talked to the CTO. We covered technology, business strategy, leadership and organizational culture, even some topics in well-being and meaning in life. It felt right, but I had learned to expect nothing. So I went through the motions upon request and went back to being my best unemployed self.

Then came the call on a Friday to make me an offer. I accepted it and started the following Monday. Unsurprisingly, my wife predicted this a month earlier. She said that it would “just happen one day” once I had stopped trying so hard. And so, just like that, I landed. A year and a half later.

It took two months for unemployment anxieties to filter out of my system and there was an initial period of unclear expectations. Despite all that, we quickly found our groove and I'm happy to say that it's a great fit with meaningful work. We’re a dynamic, tight-knit team that has fun working our butts off. Our communication is both kind and efficient. We weave purpose, empathy, and trust into our conversations, and we rely on each other’s integrity. Simply put, it’s been a joy.

Nine takeaways

I learned a lot from this chapter and it’s hard to summarize the takeaways. Here’s what stands out.

Make well-being a priority

I take an hour-long mid-day break every day, even if I feel “fine”, to calmly eat lunch, walk my dog, and so on. It makes me more productive by enabling deep work (Newport, 2016) in the afternoon and reducing long-term fatigue. It also makes me happier.

I do a 20-minute breathwork meditation to energize myself on slow mornings and regularly opt for two cups of black tea over one cup of coffee.

I play music for an hour on some nights before bed to relax and sleep better.

I slow down once it’s clear that I’m on a path towards fatigue. If I feel unable to concentrate, I’ll stop what I’m doing and go for an hour-long walk packed with restorative mindfulness practices.

I completely re-did the physical spaces in my house where I spend work time. It sets a very intentional tone of empowerment: good lighting, organized bookshelves, whiteboards with to-do and wish lists, and sticky notes with empowering reminders like “breathe on purpose”, “embrace the unknown”, and “leave wrongdoing with the wrongdoer”.

Emphasize collaboration with like-minded peers

There’s a saying in Spanish that goes "mejor solo que mal acompañado", which translates to “better alone than poorly accompanied”. But if you find someone who you mesh with, consider teaming up with them in an open-minded way. It can make your life much easier. You also never know what opportunities it can lead to for both of you. Grow together.

Engage generously with multiple communities

Network within professional communities, Meetups, and other social groups to feel supported and make new connections. Embrace the unknown, simply connecting with others as a human being and exploring opportunities for collaboration. Be someone who connects others and they will in turn connect you. Networking groups thrive when everyone “pays it forward” (Grant, 2014).

Be patient with relationship-building

Even though it can be a struggle at times, take the time to build relationships, including with recruiters. It only takes one or two reliable contacts to open up a lot of doors in the medium-to long term. See every conversation as the beginning of something great while simultaneously expecting nothing. This is a mindset that you can develop with intentional effort. It's helpful in job search and entrepreneurship while also being a general life skill.

Process experiences with key people in your life

Transitions are grueling, so it helps to have one or two key individuals with whom you can more deeply process what you’re going through. They could be your partner, friend, mentor, coach, or therapist. If you don’t process things, they will accumulate and slow you down like lactic acid. Cry when you need to. No serious professional in the 21^st century should be wasting their precious life energy, and inconveniencing those around them, with clogged emotional plumbing. You empower yourself by treating emotions as data, not noise (Klotz, 2020).

Explore “being” questions

We often focus on “doing” aspects of our lives like our activities and accomplishments. But sometimes there’s far more power in “being” aspects such as identity, values, purpose, and vision. Don’t be afraid to explore these with rigor and embrace the transformative changes that come with them. “Doing” questions get us somewhere, “being” questions change who we are.

Embrace complexity

This is an org psych insight and requires a shift from “knowing” to “thinking”. It means relying less on assumptions and more on curiosity. Without this we are unable to learn effectively, which includes spotting job opportunities when they cross our path (Argyris, 2008).

Prototype your resume

As I progressed through upskilling and interviews, my resume became more and more honed. Reworking it once a month became part of a planning ritual because I could use that time to dream about what it could look like. I could then take action to make those dreams a reality. It also got attention from multiple recruiters over the many months, one of whom emphasized that “the point of the resume is solely to get you a face-to-face interview, nothing more”.

Value your own time

To feel more organized, I started holding an “executive planning meeting” with myself every Monday morning to recap the last week’s progress and plan for the week ahead. To stay well-aligned with my goals, I planned out every hour of the week, then adjusted in real-time as needed. One of my coaching client calls this "pre-deciding". It's a systematic approach for separating anxiety-ridden decision-making about the path forward from calm execution to make progress along the chosen path.

Conclusion

The voyage I undertook from one full-time position to another lasted 18 months. My technical skillset has been transformed, enabling me to work along the entire technology stack from sensor to cloud. My leadership skillset has also been transformed by a toolbelt of frameworks and knowledgebases around what it means to lead and collaborate.

The psychology angle of my training, coupled with a sensitive temperament, has made me extremely discerning. I am now able to understand certain things about individuals, teams, and organizations that they themselves are unaware of. I use this capacity to empower those around me by holding space for them to grow and succeed in our work together.

I learned that generosity goes further than we think it does (Grant, 2014). Looking for ways to add value to others opens up unique opportunities for ourselves. A giving mindset turns every new acquaintance into a potential lifelong collaborator and every difficult person into a serendipitous teacher (Bolman & Gallos, 2016). We build ourselves up by empowering others, one conversation at a time.

Happy voyaging. Be well.

References

Argyris, C. (2008). Teaching Smart People How to Learn. Harvard Business Press.

Bolman, L. G. & Gallos, J. V. (2016). Engagement: Transforming Difficult Relationships at Work. Wiley.

Burnett, B. & Evans, D. (2016). Designing Your Life: How to Build a Well-Lived, Joyful Life. Knopf.

Coutu, D. L. (2002). The Anxiety of Learning. In Harvard business review (Vol. 80, Issue 3, p. 100). Harvard Business Review.

Dessler, G. (2019). Human Resource Management. Pearson.

Emotional Labor. (2024, April 12). In Wikipedia. https://en.wikipedia.org/wiki/Emotional_labor

Grant, A. (2014). Give and Take: Why Helping Others Drives Our Success. Penguin Books.

High-Performing Organizations Have Coaching Cultures. (n.d.). In International Coaching Federation. https://coachingfederation.org/coaching-in-organizations/why-coaching-culture-matters

Klotz, F. (2020). Employee Emotions Aren't Noise - They're Data. MIT Sloan Management Review, 61(2), 52–55.

Newport, C. (2016). Deep Work: Rules for Focused Success in a Distracted World. Grand Central Publishing.

Zaleznik, A. (2004). Managers and Leaders: Are They Different? Clinical Leadership & Management Review, 18(3), 171–177.

Footnotes

¹ VUCA stands for Volatile, Uncertain, Complex, and Ambiguous. It is a term originally developed in the US military to describe ever-changing and unpredictable conditions. It is now used in the business and tech innovation worlds to describe the unique challenges of entrepreneurship.

² If you empower an employee too much, there’s a chance they will see the limitations of their assigned role, and how it may not be in their best interest to retain it. That goes against traditional corporate thinking, which tasks managers with maintaining control over their subordinates’ beliefs and behaviors. A loss of control is seen as a threat to the bottom line through reduced effectiveness of power structures. Thus a contemporary motto for corporate culture might read “bring your full self to work, our way.”