In this episode, Dave and Jamison answer these questions:

1. Hi Dave and Jamison,

   Long-time listener, first-time question asker. Thank you both for the wisdom, perspective, and jokes you bring to the podcast.

   I recently received an inheritance of around $500,000. It’s not “quit your job and buy a yacht” money, but it is enough to reshape my life. I’m in my late 30s, currently working in a senior engineering role. I’ve had a solid run in the world of code, but I’m ready to walk away from it, zero regrets, just done. What’s pulling me now is UX and product design: more creative, human-centered, systems-aware work.

   I’ve applied for a one year master’s program in UX design, starting in 2026. I’m planning a sabbatical before that to travel, reset, and explore - think trains across Canada, a design conference in Vienna, a food tour in Greece. I’m also investing in short courses and portfolio work during that time.

   Financially, I’ve been careful: I paid off my mortgage, invested part of the inheritance, and set up a buffer. So I’m not winging it… but I am stepping away from a six-figure salary, a career my friends and family have supported me to build, and am will have no income for the next 18 months, and that’s a little scary. I want to use this opportunity well, not just coast, or panic-spend, or accidentally put myself in a worse position five years from now.

   How would you approach this kind of mid-career pivot with a windfall cushion? Any mental models, risk assessments, or “soft skills” wisdom to help me stay brave and smart?

   Thanks again for everything you put out into the world.

2. Hi Soft Skills Engineering Team,

   I’m the oldest person on my team (by a respectable margin), and I’ve been taking great delight in gently baffling my younger colleagues with expressions like “I’ll get that done in two ticks,” “give me a bell if you need help,” and “stay on the line after stand-up” (even though we’re on Teams, not a landline).

   It has become a bit of a sport for me to see how many retro, obscure, or regionally-specific phrases I can sneak into our chats and meetings before someone finally asks, “What are you even saying?”

   My question is: What other delightfully old-school and vaguely professional expressions can I deploy to maintain my status as the team’s resident linguistic cryptid?

   Thanks for all the great advice you give, and for validating my mission to keep corporate life interesting!

   Warmest regards, Resident Old Person

In this episode, Dave and Jamison answer these questions:

1. I am a data scientist and was recently passed over for promotion to senior because my projects weren’t “senior level” enough, and I do too many ad hoc requests that delay delivery of my bigger projects.

   I am a go to for VP and C suite level execs in my company and am commonly asked to help with incidents, all of which are main reasons my projects get delayed. At the same time, I am told by my manager that requests from these stakeholders/incidents are more important than my projects. Every time I try to push back and let stakeholders know that a project will be pushed back due to incidents, they all agree it’s the right prioritization. And yet, every single performance review I get the same feedback about too much as hoc work.

   I would really like to try again for promotion but I feel like I haven’t been able to change my balance of ad hoc work at all (this is actually getting worse), and support from my manager is lackluster - I don’t feel like it’s even worth trying again in a few months. What can I do to change this dynamic? (Besides quitting!) or is this a poor management/process problem that I cannot solve myself?

2. A listener named Bob says,

   I want to transition into web development at the least. I have been teaching myself, but I also know that the dev world is more about connections than anything else. I have reached out to multiple people but really have not gotten far. I really want a career transition. I have found a Bachelor of Science degree in web development at Full Sail University. I would graduate in 2.5 years. Is it worth it to take this program or keep self-learning and building out projects? I would be taking this degree all while making time for my family.

In this episode, Dave and Jamison answer these questions:

1. I had my performance review two months ago where I scored a “Does not meet expectations”, which I definitely understand, and my manager told me that some of my coworkers had been complaining about me. I’ve been working hard on improving ever since and my manager told me that they were really impressed with my progress and told me that some of my coworkers had expressed similar sentiments.

   I have now gotten a really good job offer but I’m reluctant to take it. I’m still working on improving myself with the help of my manager and I don’t want to stop working on this. I would also like some more time to show my coworkers that I really have grown before leaving, feels like that would leave behind a more positive image of me. I’m fairly junior still so contacts seem good to have, and better performance does too, and a better job does too. What should I do? :D

2. Listener Michael Q asks,

   ‌

   Hello! I only recently discovered this podcast but it has quickly become a daily ritual in my commute to and from work. Although I am more of a mechanical and data focused engineer, I find the lessons extremely applicable! I work at a midsized biotech company. I have been in my current role for about three years as a product engineer. Because I’m on the commercial side, my contributions have been very visible to the higher ups and have gotten a lot of recognition, which has been great. I am now transitioning to the more hardcore engineering team. Although I admire this team and think they are the most innovative group on site, I think their work goes largely unrecognized as behind the scenes magic. I think they deserve more recognition and accolades for the work they do. How can I bring them into the spotlight? Or am I naive in assuming that just because I am motivated by recognition, everyone else would appreciate it too? Note: I do not want to quit my job.

In this episode, Dave and Jamison answer these questions:

1. A listener named Mike says,

   To what degree do you think it’s appropriate to talk with your peer managers about people that have moved from their team to yours? How much weight do you give their criticisms of an IC that they used to manage that is working out just fine under your leadership? How do you know if it was mostly due to a conflict in their relationship, or if there’s a nugget of truth you need to look out for?

2. Hi, thanks for a great show. I’ve listened to 400 episodes in a year - thanks for making my commute fun!

   I’ve been at my current job as a software developer for a year. It’s a great company overall, but we rely on a 30-year-old in-house ticket system that also doubles as a time reporting tool. It lacks many basic features, and project managers often resort to SQL and Excel just to get an overview. As you can imagine, things get forgotten and lost easily. Everyone dislikes it, but the old-timers are used to it.

   They want any replacement to be cheap and also handle time reporting, which really limits our options. I suggested to keep using the old system for time reporting only for now, but the reaction made me feel like I’d suggested going back to pen and paper.

   While the company is old and set in its ways in some areas, it has made big changes in others, so I’m not ready to give up hope just yet. How can I at least nudge the company toward adopting a more modern ticket system to improve visibility and planning? I’ve shown examples that save time and offer better overviews, but it hasn’t made much impact. Where should I focus my efforts—or do I just have to learn to live with it?

   Some more context: This is in Europe and the culture at the company is generally open to feedback and discussions from anyone. I have 10+ years experience and a relatively good influence. My manager is driving change successfully to make the company more modern but I suspect he might have given up on this one.

In this episode, Dave and Jamison answer these questions:

1. Mr A. N. Onymous says,

   Hi Dave and Jamison,

   Long time listened, second time caller! I wrote a little while back with a common new-manager question about how to handle one of my reports who was at the lower end performance wise, but at the top end on the pay scale. I’d been trying to manage it by getting raises for the rest of the team in order to balance things out a bit (and make the rest of the team happy). I did consider Limogeage but having them on the team was better than a vacancy.

   Fast forward a year or so, and the problem resolved itself when this team member left - or so I thought. We’ve had a few months gap before opening recruitment again, and it turns out this team member wasn’t happy at their new role and has applied to come back. Given they negotiated well with us the first time I’m guessing they’ve had a healthy pay bump at their new role. What should I do?

   On the one hand I know their performance, they do deliver well and I’m happy working with them and managing them. Would it be rude to offer them to come back at their previous salary (assuming they’re the “best” person when we interview)? Will they be offended if we don’t offer them the role?

   We haven’t had interviews yet - so help me Dave and Jamison, you’re my only hope!

2. AI has taken over my team mate’s brain. HELP!

   I work for a ~10ish or so team building a B2B finances related app for several platforms (mobile, web, backend, etc). On the Web team, there’s only two of us.

   I’ve been on this team for around 4 years now, and during this times I’ve had several coworkers (the previous ones have either left the company voluntarily or involuntarily, moved to other teams, or completely left the field). I’m 100% convinced it’s not because of me, so let’s take that out of the question right away :-). All of this to say is that I tend to be the person that knows the most about our (quite large) codebase.

   We work on a ten-year-old React application with some technical debt, but overall I think it’s pretty good.

   My coworker comes from Android development. While he’s a great developer and has AMAZING soft skills (probably a listener of this podcast!, or maybe not because he has not quit yet?) he’s a little bit lacking on the general “Web Stuff (TM)” knowledge and many of the specifics details of our codebase.

   A bigger problem is that he seems to have totally given up on learning web skills or understanding our codebase and is instead just tab-tab-tab-ing autocompleted AI crap all over the codebase.

   His code works as expected, but when reviewing his PRs I feel like a slave of the AI. I’m not reviewing another human’s work, but just what some AI model is doing. While it works, it’s terrible code for another human to maintain. For example, there’s lots of “inline” crap that we already have utility functions or libraries for, regexes everywhere, custom CSS all over the place instead of using our design system, abuse of the CSS cascade instead of using our CSS-inJS solution, large files with lots of code repeating existing logic that’s already somewhere else, and code comments every 2 lines or so which provide no value, but that’s what AI does to explain things.

   I’m not against AI (I also have explicitly to say this to prevent it killing me in the future). I use it for explaining things to me, writing utility functions, suggesting improvements, or as a google search replacement that saves a lot of time.

   But leaving AI to do your work mindlessly while you sip orange juice and watch how it codes is wrong. We’re not there yet. These PRs work and are difficult to reject because management wants to ship fast. However, they are harming the codebase. We’ll get to the point where only AI will be able to touch it due to the amount of repetition, duplication and overall non-human friendly code.

   How do I tell this person “Please stop doing this and instead learn things properly, and use AI as a tool and stop you being the tool of the AI” without hurting any feelings, and without being seen as the AI grinch?

   Thanks for your help! Love the podcast, and why scroll keeps jumping up when writing on this form? Seems like AI is boycotting me.

In this episode, Dave and Jamison answer these questions:

1. Albert Nonymous asks,

   I am the CTO at a small (5 engineers) tech start-up with non-technical founders. I was their first full-time employee and as such have been able to fully form this company the way I want. I’ve worked here for 9 years now and own 10% of the company. I enjoy the tech and the job itself. The pay is ok, not crazy Silicon Valley numbers but pretty good for a country with free health care.

   However, I started here while still in university. This is still the only job I’ve ever had. I am afraid that my resume will become less valuable the longer I stay here. I still keep up with current trends with hobby projects, but I’m worried that my resume will become less valuable if I ever need to look for another job.

   Also, I don’t believe this company will succeed in the long run. I am still the only person on the board who knows how our tech even works and I have found myself slacking off quite a bit during the last year since having my first child. In the meantime, I also feel like I can’t just quit this job since that will almost certainly spell the end for this company and all its employees (some of which I count among my friends after all these years). What do I do? Am I overthinking things? Can I just keep working here until it eventually goes under? Or do I absolutely need to bite the bullet and pull the Jamison and Dave Time-Honoured Special™ and quit my job before I become totally un-hirable?

2. For much of my 9 years as a software engineer, I wanted to be a leader. I just really enjoyed mentoring, training, improving workflows, working with stakeholders and co-ordinating on projects. Leadership seemed like a natural fit and so I was super psyched to be finally made a team leader last year.

   It has been hell.

   It has been like falling backwards out of a tree and hitting every branch on the way down, meanwhile it’s literally raining anvils and sabre toothed tigers. The constant pressure to have work lined up for the team and be able to report on the activities of the team at a moment’s notice is unbearable. I can’t stand being responsible for the delivery of other people’s work, writing up reports that no one reads or painstakingly de-noising pointless metrics. I dread having to pull eager young developers out of refactoring rabbit holes.

   Fortunately, as I took this ‘promotion’ with no raise, I’ve easily been able to get myself busted back down to IC. Happy days 😎

   The problem now is that I have no idea what to do with my career. My core experience is with dot net as a mid level engineer but honestly I’m what I would call a ‘hyphen’ shaped developer - I’ve seen and done a lot things but not to an expert level. Front end, back end, BI, and everything in between. That felt ok when I was aiming for leadership but now I feel lost. I honestly feel ready to go full goose farmer 🪿.

   What do I do next?

In this episode, Dave and Jamison answer these questions:

1. One of my employees is probably getting laid off, what do I do!?!

   I’m a tech lead / manager for a consultancy and a contract reduction means that one of the people I supervise is likely going to get laid off soon! We’ve found new roles for most of my people, but it’s likely that at least one will get laid off.

   I want to help this person out. How much support is typical for a manager / ex-manager to provide in a job search, and how can I go above and beyond without doing too much?

2. Over the last year, my company has gone through 3 rounds of layoff. The engineering culture has changed dramatically. With the fraction of engineers remaining, I am increasingly concerned that it’s going to be me next. The company’s posture is that everything is “business as usual” and there is nothing to be worried about, but this is what has been said all along. Morale seems to be low with low engagement in department initiatives.

   I am looking for some advice here, if I stay with the company – what is a healthy way to engage with the current culture to build it back up (or evolve it into something new)? If I decide to leave the company – how can I set proper boundaries to prepare for leaving, but remain engaged until a new opportunity arises?

In this episode, Dave and Jamison answer these questions:

1. Hey, long-time listener, listened to almost all episodes now and have been loving it since day 1!!

   I am a senior engineer at FAANG and work 45-50 hours a week and have a lot of cross-org responsibilities. I am lucky to have a beautiful wife and two wonderful young children. I guess, you can imagine how difficult it already is to manage work/life; especially because I am working remote from a different timezone with large dilation.

   I did lots of side projects before I had a family. But I was totally okay leaving all that behind for a great family life. Now, I have been struck by a really cool idea for an AI-based product that intersects with static analysis and my day-to-day work, which I cannot stop thinking about. I am sure that this project would be more than I could handle at the moment without cutting back on anything else.

   The question now really is, how do people with families and FAANG jobs do side projects? Or do they even? Do they have more than 24 hours in one day?

2. Hello! Love the show, one-time contributor :p

   I’m in agony about my recent compensation change regarding my promotion and I am looking for some wise guidance (and if not that, some funny jokes will do).

   Context: I work at a big tech company. I got promoted to a senior engineer, but. I didn’t get a bump to my salary. Instead, the company “indicated” that the raise would happen in six months, at the next performance review, which happened last week.

   What did I end up getting? Nothing :)

   Why? Apparently they have not been giving salary bumps to people who get promoted, and it has enraged people.

   It hurts my pride. I consistently get good performance reviews & peer feedback. People go out of their way to say how good my work is. I have every evidence to say I am a strong performer.

   My manager is very supportive and tried escalating my case. But the company didn’t budge. They did say that “there’s a chance” to “make it right” in 6 months.

   On the one hand it feels petty to leave a company because I didn’t get the raise I wanted, especially when I do really enjoy working here. On the other hand…I am very disappointed.

   What do I do? Do I stick it out for another six months and see what happens? Are there options left other than start prepping myself for interviews?

   You are amazing people. Cheers.