The Reasoning Show

The Reasoning Show AI moves fast. Thinking clearly matters more.

The Reasoning Show cuts through the hype to explore how the smartest people in enterprise AI actually make decisions — the strategy, the tradeoffs, and the hard lessons no press release mentions.

Every week, hosts Aaron Delp and Brian Gracely sit down with the founders building the tools, investors funding the shift, and operators running AI in the real world. Not hype. Not panic. Just clear-headed conversations with people who have to make actual decisions.

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The Reasoning Show

Mid Career Job Changes

February 15, 2019 • Aaron Delp & Brian Gracely

0:00 | 41:55

Show: 385

Description: Aaron and Brian talk with Keith Townsend (@CTOAdvisor) about jobs around the IT industry, and the opportunities, challenges and trade-offs in making various types of mid-career job changes.

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Show Notes:

Topic 1 - Welcome back to the show. Want to talk about the pros and cons of various types of jobs in and around the IT industry - Vendors, Integrators, Contractors, Consultants, IT within a Company (Customer)

Topic 2 - Most of the 2000s and about half of the 2010s were a huge boom for remote workers. It feels like that trend is reversing. Lots of Silicon Valley companies are reversing it, the major Public Cloud providers are specific about location, IBM had a push back towards offices. Walking the fine line between a remote team or an in office team. Also, challenges to stepping into leadership. Some leadership is not remote friendly historically

Topic 3 - If you decide that you want to work around “emerging” technologies, you’re usually having to decide between a few critical factors - travel, visibility/marketing/advocating, salary certainty, and career path.

Topic 4 - “Move up the stack” or “Move towards value” - Is this something that is realistic for people that have 5+ years in a skill set? What are some realistic things people could do in this domain?

Topic 5 - What are some examples you’ve seen or recommends you’ve been given about how to make these transitions?

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