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.