Episode 468: Should I take a mini-retirement and doubling down on anachronisms

<p>In this episode, Dave and Jamison answer these questions:</p>

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<p>Hi Dave and Jamison,</p>

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

<p>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.</p>

<p>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.</p>

<p>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.</p>

<p>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?</p>

<p>Thanks again for everything you put out into the world.</p>
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<p>Hi Soft Skills Engineering Team,</p>

<p>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).</p>

<p>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?”</p>

<p>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?</p>

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

<p>Warmest regards,
Resident Old Person</p>
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