Unretirement

From Employee to Contractor

When Tim moved to Seattle in June 2020, Obsidian wasn't set up for out-of-state employees, so he was switched to contractor status. He was fine with it. Word spread that he was available, and he started getting calls from established developers and studios — all people you'd recognize, all under NDA.

These studios had already built substantial games. They weren't asking hypothetical questions — they had real projects with real problems and wanted Tim's help across various areas: dialogue systems, code architecture, level design, system mechanics.

The Consulting Work

What made this consulting valuable was the diversity and depth:

Every Studio Was Different

The games ranged from full RPGs to action RPGs to games borrowing RPG elements. Each studio had a different development process, different priorities, different personalities. One studio was heavily level-design-forward — they laid out maps before even finalizing system mechanics, thinking in terms of environmental flow and player movement rather than starting from setting and story like Tim would.

Spotting Hidden Assumptions

A key part of Tim's value was identifying underlying assumptions teams didn't realize they were making. At one studio, a level designer was building levels that assumed cover mechanics would exist — but the team hadn't actually committed to that system. Tim's question ("You seem to be assuming you're going to have cover mechanics — is that true?") likely saved the company significant money by surfacing the disconnect early.

Experience Over Hypotheticals

Unlike other contractors who'd say "I'm worried this might happen," Tim could say "this did happen — in multiple games, and here's what we tried." Having encountered the same problems across multiple projects and attempted multiple solutions, he could share what actually worked and what failed, and why. This concrete experience was far more useful than theoretical warnings.

The Playtesting Story

At one studio, the team asked Tim to play their game for a couple hours while the game director, a level designer, and a system mechanics person watched. As Tim played, he could hear them reacting: "Why is he doing that? Why'd he go in that way?"

Tim found a tower where the intended solution was to pick a lock or find a guard's key. Instead, he discovered he could climb part of the tower and reached a window that looked open and accessible — but wasn't actually enterable. The real issue wasn't that climbing should be an alternate solution; it was that the visual language was wrong. The window shouldn't have looked passable if it wasn't. This kind of insight — distinguishing the surface problem from the real problem — comes from deep experience.

Junior Designer Pitfalls

Tim notes that junior designers with outsized egos often think they've uniquely solved problems that veterans have already attempted dozens of times. They inevitably hit the same issues. Part of his value is simply having tried the "obvious" solutions enough times to know exactly where they break.

Why Unretirement

Contracting had downsides. Tim didn't enjoy the constant search for the next gig, the context-switching between wildly different projects back-to-back, and the fact that a single contract couldn't sustain full-time work. He preferred going deep on one thing rather than skimming across many.

What Unretirement Looks Like

Tim returned to Obsidian as an in-person employee in a consultant-like role — not a director, not in charge of any project. It's essentially what he did as a contractor but exclusive to Obsidian, much deeper, and with the intention of staying through project completion.

The Power of Spontaneous Conversation

The biggest advantage of being back in-office: spontaneous discussions. In just seven weeks, Tim had countless unplanned conversations — people stopping by his office to introduce themselves, chatting at the bagel counter, getting pulled into discussions about level design, art pipelines, system mechanics, audio, and narrative design.

These conversations follow a pattern: someone says hi, Tim asks about their role and project, and suddenly they're deep into a real design problem. Tim isn't their boss — he's just offering another way to look at things, another light to shine on a problem. No scheduling required, no billable hours to worry about, no formal meetings. Just "swing by my office" or "let me come by and we'll chat."

Tim is emphatic that these interactions would never have happened over video calls — and he knows this because they didn't happen during his remote contracting period. He considers in-person spontaneous conversation an irreplaceable advantage, while acknowledging remote work has its own merits and works well for some people.

The Bagel Test

Tim's description of bumping into colleagues at Obsidian's weekly bagel day — trying to distinguish blueberry from raisin bagels while colorblind, and falling into deep design conversations over cream cheese — perfectly captures what he values about being physically present. The best insights come from unplanned moments.

The Role in Summary

Unretirement is Tim applying decades of experience not by directing, but by being available — deeply embedded in one studio, easy to reach, free from the overhead of contractor logistics. He sees it as the right fit for this stage of his career: helping people at various stages of theirs by sharing hard-won knowledge through conversation rather than authority.

References

• Tim Cain. YouTube video. https://www.youtube.com/watch?v=akKcwfEkuKQ