Career Development

Non-linear career strategy under AI-era uncertainty — breadth over ladder-climbing, near-term horizons, and finance-aware late-career planning.

Also known as: squiggly careers, broken comb, Staying wide, Career ladder, tour of duty, Two-year horizon, whole self, extreme time value of money, time value of money

AI Fluency (as Career Expectation)

How authors use it

Oldest first (extraction date when no publication date is known).

AuthorTheir termTheir meaning
Scaling Uber with Thuan Pham (Uber's first CTO)
The Pragmatic Engineer · 2026-04-10
tour of dutyA self-defined phase of engagement with a company organized around a specific purpose (fix, scale, or stabilize)
Developing Your Leadership Skills toward Principal Engineering
Ben Linders · 2026-04-15
broken combA skill profile with deep expertise in several areas (the long teeth) and gaps between them — contrasted with T-shaped (one deep area) or generalist profiles. Having more 'teeth' from diverse life experiences makes you more effective as a principal engineer
Developing Your Leadership Skills toward Principal Engineering
Ben Linders · 2026-04-15
squiggly careersNon-linear career paths that include role shifts, moving in and out of management, lateral moves — presented as a positive pattern rather than a lack of focus
Developing Your Leadership Skills toward Principal Engineering
Ben Linders · 2026-04-15
whole selfBringing the full range of your skills, experiences, and identity — including those developed outside work — to your professional role, tied to psychological safety
Extreme Time Value of Money: Late-stage Career Planning
Kent Beck from the archives · 2026-04-21
time value of moneyThe economic principle that a dollar today is worth more than a dollar tomorrow because today's dollar can be invested. Beck uses it both as a finance concept and as the conceptual foundation of XP-style software practice (earn sooner, spend later).
Extreme Time Value of Money: Late-stage Career Planning
Kent Beck from the archives · 2026-04-21
extreme time value of moneyThe condition Beck names where mortality (or, in his case, Parkinson's-shortened usable time) makes the discount rate explode. The 'extreme' is what differentiates late-stage career planning from ordinary career planning.
Supporting Your Employees' Career Growth When Everyone Is Overwhelmed
Rebecca Knight · 2026-05
Career ladderAn outdated mental model of linear vertical progression through predictable rungs; treated as something to move away from.
Supporting Your Employees' Career Growth When Everyone Is Overwhelmed
Rebecca Knight · 2026-05
Staying wideCultivating breadth and scenario-based bets rather than deep specialization, because specialization carries automation risk in a fast-changing landscape.
Supporting Your Employees' Career Growth When Everyone Is Overwhelmed
Rebecca Knight · 2026-05
Two-year horizonThe planning window in which Bidwell claims one can speak with confidence about skills; contrasted with a ten-year horizon where one cannot.
Achieving Compliance as a Platform Engineering Team by Helping Developers
Ben Linders · 2026-07-23
Tour of Duty

Documents (30)

Propositions touching this concept (11)

By publication month, oldest first (extraction month when no publication date is known).

2019-02

2024-08

2026-04

2026-05

2026-07

2026-09

Open gaps (59)