Patterns of Iteration: Celebrating Three Hundred Episodes of Career Podcasting

Nerd Journey: Career Advice for the Technology Professional

What can you learn from 300 episodes focused on career progression in technology? This week we’ll remind listeners of our show’s mission and share the origin story of the podcast. Listen closely for the lessons we’ve learned, the patterns we have seen in our discussions and guests, the feedback we want to hear from listeners like you, and some recommended episodes if you want to dive deeper in specific areas.

As part of episode 300 we’re also announcing the recent creation of our layoff resources page that you can find at nerd-journey.com/layoffresources. This is a curated list of our most impactful discussions on layoffs with HR professionals, career coaches, burnout experts, entrepreneurs, and technologists like you. It’s been put together in a specific order to help you process layoff events, get practical tips on moving forward, and learn from the experiences of others.

Original Recording Date: 10-26-2024

Topics – Restating Our Thesis, The Origin Story and Motivations, Lessons Learned, Trends and Patterns, Key Ideas and Books, Progressing as an Individual Contributor, Management as a Career, Looking at the Future

1:01 – Restating Our Thesis

• Welcome to episode 300!
• We wanted to start by restating our thesis for the show, especially for anyone who might be a new listener to the show.
  • We (John and Nick) are focused on serving the technology professional with the goal of bringing to light information on career progression and expansion that we did not know when we worked in IT Operations. We’re looking to answer questions like:
    • How do I find a new job if I’ve just been laid off?
    • How do I get better at my job?
    • How do I change job functions within the organization I’m in?
    • How can I change organizations / companies?
    • How do I gain recognition?
    • How do I progress in general in my career?
    • What are the different roles that exist under the technology umbrella that I might be qualified to do?
  • We’re extracting the patterns from stories of technologists not so different than you. Our guests have either worked in technology or have a unique perspective on the industry or trends within it. Releasing our discussions in multiple parts allows us to go deep into details and extract those patterns of the different ways one could go about accomplishing some of the aforementioned goals.
    • We also want to educate listeners on how many roles are possible under the technology umbrella as a whole and how you might be qualified for more jobs than you thought. You’ll hear us discuss relatable experience quite a bit on the show.

3:46 – The Origin Story and Motivations

• Right before Nick started a new job in late 2017 (that John had referred him for), John suggested the two of them start a podcast.
  • At first, Nick wasn’t sure what he would say on a podcast, but he said yes.
  • John says in the beginning neither of them was clear on what the podcast was about yet.
    • Based on his experience at a distributor and a technology vendor after being in IT Operations, John felt there were paths and roles that people did not know about that could result in greater pay. He thought they should publicize it and talk about different ways to accomplish it.
    • They also had other ideas like sharing details of the solutions their employer (a technology vendor) was releasing. John remembers recording several episodes on these topics that were never published. Nick recalls some of their first intros using the words “IT news and opinions based on our points of view.”
    • John and Nick didn’t think they could make an impact by just talking about the technology and promoting it. Many others were doing it.
    • “I think a lot of the career stuff just bubbled up to the forefront. We found the reason later on. It just got to be more and more clear that that part of it was the only thing that we should really focus on.” – John White
    • Nick says we have to talk about technology a little bit, but it wasn’t about the nerdy parts of the tech itself. It was more about how working in technology and focusing on it changed someone’s career, how they progressed, etc.
      • Nick had no idea there were so many different roles one could have when they started the podcast.
    • It seemed important to not only educate people on different technology focused roles but also talk about the process of applying for those types of jobs.
  • Nick and John worked together earlier this year to revise the podcast description. It was kind of right, but over time the theme had crystalized even more so than what was previously written in the description.
    • This is also part of the reason you see “Career Advice for the Technology Professional” in the show’s title now.
    • While we are not paid to give career advice, we sure do love continuing to learn on this topic!
• If you hear ads when you listen to our show, they are NOT from us! We’ve never used ads.
• Our costs for the podcast center more on time spent than money. Hosting costs and other subscriptions isn’t a huge expense. It did not seem realistic to monetize in a way that would offset the cost of our time, so we didn’t do it.
• What is it we hope to get out of the podcast if it isn’t money?
  • For John, the payback is more about exposure to guests, hearing their interesting stories, and knowing listeners are finding the models our guests are presenting valuable. One model is coming from a nontraditional background to work in technology. We’ve figured out that there is no “traditional” background.
  • Nick highlights the fantastic people we’ve met as we’ve heard their stories. For Nick, the podcast helps him in addition to helping other people.
    • We talk to people before and after we interview them and try to keep up with how they are doing.
    • Nick says when you edit the show, you get to listen to the advice given in episodes multiple times.
    • “Selfishly, I like doing it for me…. If it helps me, my hope is that it helps other people too.” – Nick Korte

11:43 – Lessons Learned

• Nick has found that you will make time for the things you like and enjoy. In fact, he and John recorded episodes while he was on vacation in Galveston right before the show launched.
  • Nick recounts editing the podcast on cruise ships, in the passenger seat of a car while on a road trip, in hotel rooms, and of course, at home…all out of an unwillingness to miss a release.
  • John had some major life events happen at different points like buying his first home and having a child which required him to step away from the show. The first time this happened, Nick had to learn how to edit.
  • Nick’s wife and daughter know how much he loves doing the podcast and support him in it. They know that weekends are for podcasting and editing. He is only able to do this because of their support.
  • If you plan to do something like this (start and maintain a podcast), make sure you have the support to do it.
  • A podcast takes time, and when you begin you will not be fast at any of it. Nick feels like he and John have improved in the questions they ask, their prep, and hope the quality of the show has improved over time.
  • Hopefully the findability of the show has improved over time with iterative improvements on the show’s description and metadata. Nick wishes they had done this better as the theme became more crystalized.
    • John thinks maybe we would have been better at this part if either of us had marketing backgrounds.
  • With the experiences being part of technical communities in the past and being in pre-sales for a while, Nick is not shy about asking people to be on the show if they have a great story. Neither is John.
    • It has not been hard to get people to say yes once we do the prep work and share what we’re trying to do.
    • “You don’t know when and where, but somebody’s going to be helped by hearing your story. I think people want to be able to help, so it’s finding people that have that compelling lesson that’s embedded in their story.” – John White

16:02 – Trends and Patterns

• Some things we have seen have changed over time, while some have been timeless.
• The strength of the job market has varied over time.
  • Right now, in late 2024, the job market is difficult, and we are seeing many layoffs in the tech industry. There are many reasons behind this – consolidation, interest rates, etc. There are still jobs open, but it’s a challenge when thousands of people have lost their jobs so close together because it might mean high competition amongst a large candidate pool.
  • In 2021, it was a very hot job market with tons of hiring, making finding candidates difficult.
  • As time goes by, the place we are in the job cycle changes quite a bit. John says it’s been interesting to hear our discussions during both a hot job market and a difficult job market.
  • If you are worried about layoffs or have been impacted, Nick mentions the recent creation of a layoff resources page you can visit at nerd-journey.com/layoffresources. You will see the title of “What Can I Do in Response to a Layoff Event?” This is a curated list of some of our most impactful conversations on the show about layoffs given to you in a specific order to help process the event and understand what you can control.
    • You’ll hear from business psychologists, burnout experts, career coaches, entrepreneurs, and technologists.
• John mentions some discussions we’ve done on the best practices in searching for a job. One example is accepting interviews even when you’re not actively seeking a new role to gain practice. Specifically, this is practice when the stakes are very low.
  • Taking an interview may help you learn about a really interesting opportunity.
  • John encourages listeners to know why they are staying at a particular employer. Staying at your current employer has to be better than making a move for you to stay.
  • We’ve talked about considering the type of company to work for and the role you would like to have, keeping them in generalities instead of specifics.
    • Consider the type of work you would like to be doing, the environment in which you would want to work, the types of co-workers you would want, how all of this might make you feel, etc.
    • The above goes back to concepts we discussed in Episode 19 – Process over Outcomes and Dreaming in Bands
• We have also done past episodes on resume construction. While we do not council people on resume writing for a living, we have written several of our own. Here are some recommended episodes from our foundations series that might help you (each contains links in the show notes to other helpful resources):
  • Episode 203 – Revisiting the Foundations of Resumes
  • Episode 204 – Revisiting the Foundations of the Job Search
  • Episode 205 – Revisiting the Foundations of Job Interviews, Part 1
  • Episode 206 – Revisiting the Foundations of Job Interviews, Part 2
• We’ve discussed interviews and explained the goal of an interview, which John mentions is not always obvious.
  • When John worked for Google he conducted many interviews even though he was an individual contributor. Much of it was to evoke how people think and solve problems.
  • We have also done episodes covering the different types of interviews like those with a recruiter or hiring manager, a technical screen, a vibe interview with a leader, etc.
  • There are also many great interview stories people have shared throughout the years. In the interview, we want to be able to tell our career narrative. This is something Jason Belk shared with us in Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2). One of the days we build a narrative is documenting our work and showing our work so we can speak about it with others.
    • Telling your narrative is not something a person can do if they haven’t thought about it!
    • How did your experiences change the way you think and solve problems?
    • “You need to think about it ahead of time and then construct it and then practice telling that story. And then revisit that because you’ll change. And then your perspective on the past will change also.” – John White, on career narratives

24:09 – Key Ideas and Books

• We’ve compiled a list of ideas listeners need to consider / think about as they start to focus on career progression (i.e. getting better at your current job, becoming a higher performer, etc.).
  • Proof of Work
    • This goes along with the book Show Your Work by Austin Kleon. This is a short and very digestible read containing stories about the power of documenting your learning, being a beginner, sharing your experience, and how it can help your career.
    • One practical implementation of this is blogging about learning a specific topic.
    • Kleon’s book makes a compelling case for learning in public, which means documenting the learning in some way so you can tell that career narrative we spoke about earlier.
  • Turn Information into Knowledge
    • This came to us via a book recommendation from previous guest Josh Duffney. Josh spoke about what he had learned after reading How to Take Smart Notes by Sonke Ahrens, which is often called Zettelkasten (a knowledge management system).
    • Be sure to check out our full discussion with Josh in Episode 156 – Better Notes, Better You with Josh Duffney (1/2) where you will find links to a book Josh wrote called How to Take Smart Notes in Obsidian.
    • John says this methodology has revolutionized how he works. It’s part of showing your work but also a way to keep track of things you know. We can take notes on what we are learning and then formalize our thoughts into our own words, putting them into a system that allows you to create connections between concepts you have learned. It becomes knowledge once it is in a system that allows retrieving it, taking action on it, and then publishing it.
    • Nick feels he could improve in note taking to make it more like the smart notes methodology.
    • John mentions this is less about full adoption and more about being exposed to the idea and trying to implement it in some way. There is no perfect way to do it!
  • Improve Your Ability to Do Complicated Knowledge Work
    • This point is based on Deep Work by Cal Newport. We recorded a 7-part discussion series on this book starting with Episode 141 – Book Discussion: Deep Work, Part 1 – The Why and ending with Episode 147 – Book Discussion: Deep Work, Part 7 – Become Hard to Reach. Episode 147 contains links in the show notes to all discussions in the series.
    • John feels the series of episodes we did stand out as an example of how to take smart notes as applied to the deep work concept. Even just listening to our first episode in the series will give you an idea of what the book is about and an overview of the concept of deep work.
    • This book is an example of why it’s important to be able to do complicated knowledge work and the things you need to do to be good at it. There are other books Cal Newport has written that Nick and John have also read. Cal Newport also has a podcast that is quite good.
  • Incremental Improvements
    • One of the first books we came across here was Switch: How to Change Things When Change Is Hard by Chip and Dan Heath. Another book many people have recommended in this space is Atomic Habits by James Clear.
    • The idea is making small improvements and building upon those improvements, which includes shaping your environment so you can do it well.
    • These overlap a little with the concepts Cal Newport spoke about in Deep Work.
  • Making Big Bets on Technology Waves
    • While there is no specific book here, it is a corollary to the above ideas. We’ve seen this pattern happen with a number of guests.
    • When Nick thinks of guests who have talked about technology waves he thinks of several episodes – Episode 80 – Certification and Mentoring with Manny Sidhu,Episode 188 – The Surfer of Technology Waves with Joe Houghes (2/3), and Episode 184 – Dive Deeper and Enjoy the Process with Michael Levan (2/2). Also check out Episode 264 – Back to Basics: Technology Bets and Industry Relationships with Brad Christian (2/2) to get Brad Christian’s take on making technology bets.
    • Manny Sidhu was the first one to bring up this idea. He came across virtualization in the early days and decided to go all in. The foresight to do that early on can be powerful in your career, but there may be ways to do it which are not as large of a risk.
    • If someone made a bet on blockchain a few years ago, it hasn’t played out just yet. Think about containerization and generative AI and how they will continue to change over time. Will you place a bet and position yourself within one of these trends?
    • Should we talk to more people about how to evaluate technology waves and the smart way to make a bet on a wave?
    • People often want to know where to place their focus to gain new skills and be valuable in the market. It’s a difficult problem to solve.
    • Making a completely safe bet on a technology wave might mean you are late to place your bet.

34:40 – Progressing as an Individual Contributor

• Another trend we’ve seen is progressing to a high level individual contributor, which we might refer to as becoming a principal engineer. The principal level is one of the highest job levels for individual contributors with things like distinguished one step higher. We’ve spoken to guests about what it takes to achieve the principal title and what it means to have the title in our industry.
  • A typical progression for an individual contributor might be systems engineer to senior systems engineer to staff systems engineer to senior staff systems engineer to principal systems engineer, etc. But this progression may look different inside the organization where you work!
  • This is a leadership track but not a management track. High level individual contributors like principal engineers often work on problems with a broad scope within an organization and sometimes outside the organization. It’s about technical depth and breadth but also developing other people too.
  • John highlights the principal as someone who can bring their knowledge to a project and then hand it off to someone.
  • The discussions about the principal title are some of Nick’s favorite. Recommended episodes for learning more about the principal engineer would be:
    • Episode 286 – Succession Planning: Delegation Skills and Technical Ownership with Max Kanat-Alexander (2/3)
    • Episode 287 – Scope Creep: Evaluating Impact in Career Decisions as a Principal Engineer with Max Kanat-Alexander (3/3)
    • Episode 242 – Modalities of the Staff and Principal Engineer with Ken Collins (2/2)
    • Episode 167 – Pause and Step Outside with Andrew Miller (3/3)
    • Episode 152 – The Theme of Your Career with Scott Lowe (1/2)
    • Episode 153 – Creating a Full Stack Career with Scott Lowe (2/2)
    • Episode 170 – Signal What You Want with Joe Chenevey (1/2)
    • Episode 171 – Coaches as Mindset Curators with Joe Chenevey (2/2)
    • Episode 185 – Make Accommodations for Success with Phil Monk (1/2)
    • Episode 186 – The Unassuming Architect with Phil Monk (2/2)

37:45 – Management as a Career

• This has been a trend we’ve seen. If you want to be a manager, what do you need to prepare yourself for, and what is the job of a manager?
  • We’ve had discussions about the differences between managers and the technical lead of a team.
  • There’s also the concept of the player coach where someone might be partially a people manager and still have individual contributor responsibilities.
  • John has made the transition to people manager from individual contributor. He shares that there is a 30% or so crossover of skills.
    • “Being a manager just is a whole new set of…very technical skills that don’t have anything to do with being that individual contributor.” – John White
    • John says there are companies who have developed philosophies that management can be a skill applied to any team, even if the skills of the team are different than your skills when you were an individual contributor.
  • We have also seen people move from manager back to individual contributor. It’s not necessarily a step down and might be right for you based on specific timing in your life. John says it’s just a different job.
  • If you’re listening to this and are thinking about becoming a people manager, check out these episodes:
    • Episode 244 – An Array of Decision Points with Tim Crawford (2/2)
    • Episode 252 – Management is War with Russell Swinney (1/2)
    • Episode 253 – Building Trust as an Interim Leader with Russell Swinney (2/2)
    • Episode 238 – Managers as Culture Keepers with Leanne Elliott (2/2)
    • Episode 278 – Uncovering Empathy: The Greatest Skill of an Inclusive Leader with Marni Coffey (1/3)
    • Episode 279 – Change Management: The Hardest Leap and Developing People with Marni Coffey (2/3)
    • Episode 280 – Life after Layoff: A Leader’s Sense of Duty and A Series of Good Conversations with Marni Coffey (3/3)
  • For more on the player coach role, check out Episode 231 – It Comes Back Tenfold with Chris Williams (3/3).

41:52 – Looking at the Future

• We would like your feedback on this we should be doing more of and less of. Please send any comments to [e-mail].
• Who should we be interviewing?
  • More practitioners / people who don’t work for tech vendors, resellers, or distributors?
  • Are there roles we haven’t covered that we should be like venture capitalist, procurement personnel, or platform engineer?
  • Do you have a recommendation for someone who should be on the show? We will take that and run with it.
  • Do we need to interview people in new, interesting verticals?
  • Are there specific types of companies you want to hear about?
• If you’ve heard one episode that has been valuable to you at any point, please take the time to rate the show 5 stars.
  • What did you find helpful about a show you listened to? Please share that and tag us on social media.

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: [e-mail]
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
  • Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_