Navigating Career Transitions and Financial Realities

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