The Pathless Path: How I Left a 12-Year VP Role to Build 12 Projects

The Bureau of Labor Statistics tracks that the median worker holds 12.7 jobs between ages 18 and 56.¹ But changing jobs isn’t the same as changing identities. Leaving a VP title after 12 years isn’t a job change. It’s a map change.

TL;DR

Paul Millerd calls it the “pathless path”: career transitions where the destination doesn’t exist on any established map. I lived this transition when I left ZipRecruiter after 12 years as VP of Product Design to build independently. No job offer waiting. No startup idea validated. Just four years of Past Year Review data showing that my energy came from building, not managing. This post covers what I learned: building financial runway, running experiments before committing, and following curiosity over credentials.

When My Map Disappeared

At ZipRecruiter, my career map was clear. Senior Designer to Lead to Director to VP. Each transition had precedents, mentors, and a salary band. The map worked for 12 years.

The map stopped working when I realized my best weeks were the ones where I coded a prototype, not the ones where I presented a strategy deck. My PYR data confirmed it for four consecutive years: building scored positive, coordinating scored negative.

There’s no career map for “VP who wants to write code, design interfaces, and ship iOS apps as an independent practitioner while building AI agent infrastructure.” The role doesn’t have a name. The comp model doesn’t exist. The LinkedIn profile doesn’t fit a dropdown.²

That’s a pathless transition. No destination on any established route. The choice is between forcing yourself onto someone else’s map or navigating without one.

Step 1: Financial Runway

Career experimentation requires time, and time requires savings. I calculated monthly fixed costs and multiplied by nine months. Nine months felt arbitrary, but the arithmetic replaced anxiety with a timeline.³

The number didn’t need to be dramatic. Three months of runway changes the psychology of decision-making from “I need a plan before I move” to “I can afford to explore for 90 days.” Six months converts exploration into serious experimentation. Nine months allows for a full pivot with job search buffer if the experiments fail.

I saved for over a year before leaving. The extended runway gave me permission to try things that might not work. Permission changes everything.

Step 2: Small Experiments (Before Quitting)

I ran experiments while still employed. Each one tested a different curiosity:

Experiment 1: Can I build and ship an iOS app? I built Ace Citizenship, a spaced repetition app for USCIS civics questions, over two weekends. The answer: yes, and I found the process genuinely energizing even after the novelty faded.

Experiment 2: Can I build a website from scratch? I built blakecrosley.com with FastAPI, HTMX, and plain CSS. Perfect Lighthouse scores on the first deploy. The answer: yes, and the design-to-code flow felt more natural than design-to-handoff.

Experiment 3: Can I write about technical topics? I published my first blog post and measured whether the writing process felt energizing after the novelty faded. It did. Four months later, I had 29 posts.

Experiment 4: Can I build AI tooling? I started building Claude Code hooks and a multi-agent deliberation system. 86 hooks and 3,500 lines of Python later, the answer was clear.

Each experiment cost low enough that failure was acceptable. A weekend. An evening. A side project. None required quitting my job. Each one produced a data point that introspection alone couldn’t generate.⁴

Step 3: Follow Curiosity Over Credentials

The test for genuine curiosity versus novelty: would I continue exploring this if nobody saw the work? Building hooks and agent infrastructure passes that test. I built 86 hooks and 141 tests for a system that only I use. Nobody asked me to. Nobody pays me for it. The work generates sustained energy because the problems fascinate me.

Building an AI agent framework because the technology fascinates you passes the test. Building one because “AI is hot right now” doesn’t. The distinction matters because pathless transitions take years, and only genuine interest sustains effort across that timeline.⁵

What I Built (So Far)

Not every project worked. Some stalled after the initial experiment. Some generated sustained energy and grew. The projects that survived are the ones where curiosity outlasted novelty.

What I Wish I’d Known

The identity transition is harder than the financial one. Introducing yourself as “VP of Product Design at ZipRecruiter” activates instant context. Introducing yourself as “I build things independently” triggers follow-up questions you haven’t rehearsed yet. The identity gap feels uncomfortable for months before a new one forms.

Small experiments compound. Ace Citizenship led to learning SwiftUI. SwiftUI led to SwiftData. SwiftData led to HealthKit integration for another project. The iOS skill tree grew from a single weekend experiment. No plan predicted this path.

The portfolio IS the resume. In traditional career paths, credentials open doors. In pathless transitions, shipped work opens doors. My 100/100/100/100 Lighthouse scores say more about my engineering capability than any VP title. The 86-hook infrastructure says more about my systems thinking than any design portfolio.

Financial runway buys psychological runway. The savings didn’t just buy time. They bought the willingness to try things that might fail. Without runway, every experiment feels like it needs to succeed. With runway, experiments can be genuine experiments.

Key Takeaways

For professionals considering a transition: - Calculate your financial runway in months, not feelings; the number grounds abstract anxiety in concrete timelines - Run three small experiments before committing; real-world feedback outperforms introspective planning - Track your energy data for at least two years; one year of patterns is suggestive, two years is conclusive - The pathless path is not planless; it’s iterative. Each experiment informs the next direction.

For managers supporting team members in transition: - Internal mobility programs that allow 20% time for adjacent-role experimentation retain talent that rigid career ladders lose - The strongest signal of a productive transition is increasing engagement in the new area, not a polished career plan

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