First Tracks · 02 — The Overlook

You have a degree.
The job market doesn't look like
the one you were promised.

For college seniors and recent grads — the ones who picked a major at 18, did the work, played the game, and now find themselves in a job market that's been quietly rewritten by AI while they were in class.

We don't fix your resume first. We rebuild the strategy from your actual profile — what you'd do if money weren't a factor, what your major taught you that nobody on a job description cares about, and what AI is doing to every field you might be pointed at.

What you walk away with

A Trail Map for the next twelve weeks. And the next ten years.

The deliverable is a personalized written document — your assessment synthesis, three to five Core Paths ranked with rationale, two or three Halo Paths (the adjacent options nobody told you to consider), AI impact analysis for each direction, and a 12-week action plan that gets specific about what to do next Monday.

Because the foundation is who you actually are — not the major you happened to declare freshman year — the strategy holds up regardless of which entry point you take. Resume positioning, LinkedIn framing, and how to talk about yourself in interviews all become much easier once you know which story you're telling.

Who this is for

The AI piece, briefly

89% of the Class of 2026 believes AI could replace their entry-level role. Entry-level tech postings dropped 67% between 2023 and 2024. Big tech is hiring new grads at half the rate it did in 2019. None of that means careers are over — it means the careers that work in the next ten years won't all look like the ones that worked in the last ten. The Trail Map factors that in for every direction I point you toward.

How it works

Four steps. Roughly two weeks.

Start with a free First Look. Everything from there happens at your pace.

01

Assessment stack

Holland Code (RIASEC), Ikigai, and the Trailhead Overlook questionnaire — completed on your own time before we meet. Designed for people who have a degree but not a lot of professional context yet.

02

The session

A 60-minute working session, virtual. We walk through assessment results, Core Paths, Halo Paths, and the AI impact picture for each direction. We pressure-test your assumptions and ask the questions interview prep doesn't.

03

Your Trail Map

A personalized written document delivered within a week. Recommended directions with rationale, AI impact analysis, resume and LinkedIn positioning notes, networking strategy, and a 12-week action plan with specific milestones.

04

Two weeks of follow-up

Questions come up once you start executing. Email support is included for two weeks. If you want ongoing accountability through the actual job search, that's a separate Guide Sessions engagement and we'll talk about it at the end.

The Trailhead Promise

Start with a free First Look.

15 minutes. Real conversation. By the end you'll know whether The Overlook is the right move — and if you need something else, I'll point you there.

Book a First Look