It takes more than great code
to be a great engineer.

In this episode, Dave and Jamison answer these questions:

1. Hello Dave and Jamison!

   I’m a longtime listener going back to the early days of the podcast, and I’ve listened to every episode since. When I started listening, I was beginning my career as a software engineer. Your advice has truly helped shape how I think about work, engineering, leadership, and all the weird human stuff that comes with building software.

   Now I’m more than 10 years into my career, and I’ve run into a problem that I suspect many experienced engineers are dealing with right now.

   In episode 521, you talked about how brutal the current job market is, and the question asker from that episode had been unemployed for a year. I’m thankfully not there yet, but I recently lost my job in a large layoff, and the first couple of months of searching have been pretty discouraging.

   I’m applying to roughly 10–20 jobs a day. I tailor my resume to each role, ensuring it accurately reflects the skills and terminology in the job description. I usually include a cover letter too; AI gets the privilege of writing the mediocre first draft, and then I rewrite it into something I would actually say.

   Despite all of that, I’ve only made it past the resume screen three times so far, one of those was through a referral, and several other referral applications have gone nowhere.

   The strange part is that I’ve tried applying across the whole spectrum:

   1. Roles that would be a step up, where I think I could do the job but haven’t held that exact title before
   2. Roles at roughly my current level, where I can honestly check almost every box in the job description
   3. Roles that would technically be a step down, but that I’d happily take and feel extremely confident I could do well

   So my question is: How do you get companies to actually interview you when you’re an experienced engineer in a market overwhelmed with qualified candidates?

   At this point, I’m starting to wonder whether there’s such a thing as an awkward career middle age: too experienced for some jobs, not obviously senior enough for others, and competing with hundreds of people for everything in between.

   If you were in this situation, what would you change? More networking? Fewer but more focused applications? Different positioning? Showing up at the hiring manager’s house with a fruit basket and a printed copy of my GitHub profile?

   Would love to hear how you’d approach it from the other side of the hiring table.

2. Dave and Jamison,

   Hit me with your dumbest, funniest, most brutally honest advice because I need it.

   So here’s the deal: I’m a software engineer with 30+ year in the industry, a dinosaur who’s already reinvented himself like a half-dozen times, network, dev, infra consultant, back to dev. Now I’m having a midlife-ish (okay, late-life) crisis and I’ve fallen in love with security and compliance. Like, actually excited about compliance, which I’m told is a red flag in itself.

   Problem is: I’m less than 10 years from retirement and my brain doesn’t bounce back from “starting over” the way it used to when I was a spry young whippersnapper.

   So, am I an idiot for even considering torching my comfy expertise to go be a security newbie this close to the finish line? Or is this exactly the kind of chaotic energy I need before retirement?

In this episode, Dave and Jamison answer these questions:

1. Hi Dave & Jamison! I’ve been listening for almost a year now and have worked through nearly your entire back catalog in reverse. The podcast has genuinely helped me become a better engineer, so thank you!

   I’m two years into my software engineer career at a large infrastructure company. I was promoted to SWE II last year, and this year my manager told me she felt my work was promotion-worthy, but because I’d just been promoted and she had others on the team to consider, she wants to target me for next year’s cycle instead. She gave me a spot bonus and said she’d try to make up for it in my raise.

   I understand and appreciate the honesty, but I’m also a little disappointed because I’ve worked hard to hit every milestone on the roadmap she gave me, and career progression does matter to me.

   My question is: How should I navigate the next year? What should I focus my 1:1s on? Should I push for a mid-year promotion if that’s an option, or instead focus on building an undeniable case for next year? How would you approach this if you were in my shoes?

2. Hey Dave and Jamison,

   Long time listener. First time question asker :).

   I recently joined a major tech company. Before this, I worked at a mid-sized company with about 200 engineers. In my old role, I built customer-facing products. The work was challenging and exciting, and I genuinely enjoyed it. I ended up moving to a new city to be closer to family and started looking for a job. The job search was brutal. Honestly, by the end of it, I would have accepted just about anything. Luckily, a major tech company extended an offer. The money was great, and I thought it would be a huge plus to have a major tech name on my resume. It is a fully remote role, but they did mention that they could go hybrid in the future.

   I knew ahead of time that the team built internal tools instead of customer-facing products. But after joining, I realized most of what we do is closer to operations than actual software engineering. I know I should have screened the team better. I was just so relieved to get a good offer from a top company that I accepted without thinking twice. I am not enjoying the work at all.

   I am not planning to quit immediately. However, I want to be ready to leave in about a year or earlier if they decide to lay us all off. I want to make sure I utilize my time here as best as possible. Do you have any suggestions on how I can best position myself for an internal transfer or an eventual external move?

   Also, I have been in this role for close to 2 months now. I did a 1-1 with the manager in my first week, but after that, have not had any 1-1s. He has not scheduled anything. I was thinking of scheduling it myself but not sure if that can be seen as too forward.

   Btw this is outside US, if that matters :)

   Thanks again for your advice and laughs.

In this episode, Dave and Jamison answer these questions:

1. Hey Dave and Jamison, First, I love your show and it has now been part of my Monday evening routine for many years to listen to your podcast while cooking dinner.

   I recently joined a mid-sized software company (500 people) as a senior data engineer. The salary is a significant bump from my previous job and I really like the team on a personal level. Three months after I joined, the company laid off half its employees and announced a strategic pivot away from their previous core business to become an “AI-first company” and develop new products in novel, more profitable sectors. The product that my team had been working on until that point was scrapped and there are no new projects coming from the business side. In subsequent communications, it was revealed why: Management has no concrete ideas for the future strategy, neither on what products to develop nor on which sectors to target. Instead, our team (among others) is now tasked with coming up with new product ideas to “save the company”. I’m a data engineer, not a business development manager, and while I have dealt with high ambiguity from the business side in previous roles, it was never this extreme.

   I was looking forward to working on interesting technical challenges within a great, experienced team, but now I feel like I’m expected to become an “idea guy”, a role that doesn’t really match my personality. My question is: Should I be patient and try to turn this situation into “an opportunity for growth”, or should I start applying elsewhere? I’m a bit worried that the short length of stay at this company will leave a stain on my CV.

   Many thanks to my favorite space lawyers, an anonymous listener.

2. Hi!

   My current job is at a 10k+ large risk-adverse company that currently has nil, none, nada, nichts ai tools available for coding. I of course did the only reasonable thing. I’ve gotten a new job at a middle-sized fintech company that’s going ”AI first”.

   I’m really excited about finally using ai outside hobby projects. I worry however, that my future colleagues will go too quickly ahead while vibecoding, vibearchitecting, vibetesting… leaving a mountain of tech debt behind. A lazy colleague would actually be better than an intellectually lazy colleague in this scenario. (I sincerely hope that I won’t be that coworker)

   Are my worries overblown or sane? Any gotch’as to avoid? Maybe you can give a brief survival guide to the brave new AI world?