First Tracks · 03 — The Switchback

A couple years in.
The work is fine.
And you know it isn't yours.

For 23-to-30-year-olds who don't need to start over — but know something needs to shift. You're competent at what you do. You're not falling apart. The problem is quieter than that. The work doesn't fit, and the longer you ignore it, the harder the correction gets.

We figure out what's actually misaligned and what's just early-career grind. Then we build a route from where you are to where you should be — without requiring you to quit on Monday to start.

What you walk away with

Three paths. Picked for you, not at you.

The Switchback Trail Map lays out three structured options: optimize the current role you're in (sometimes the answer is a better-shaped version of where you already are), pivot to a new direction that actually fits, or build toward a different five-year picture starting now while you still have a paycheck. Each path comes with rationale, AI impact analysis, the realistic trade-offs, and the specific next moves.

The point isn't to romanticize a leap. The point is to make the leap — or the re-shape, or the longer build — an informed decision instead of a 2 a.m. job-board scroll.

Who this is for

What this is not

This isn't executive coaching for performance ceilings inside a role you love — that's a different conversation. The Switchback assumes the misalignment is real and worth investigating. If you actually love the work and you're hitting a visibility or strategy ceiling, I'll tell you that on the First Look and point you in a different direction.

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 Switchback questionnaire — designed for people with real work experience to draw on. Now the workplace questions land differently than they would have at 18.

02

The session

A 60-minute working session, virtual. We pressure-test the three paths against your actual situation — financial reality, dependents, partner factors, geography, and how much risk the current setup can absorb.

03

Your Trail Map

A personalized written document delivered within a week. Three structured paths (optimize, pivot, build), AI impact analysis for each, the trade-offs called out honestly, and a 90-day action plan with specific milestones.

04

Two weeks of follow-up

The questions get harder once you start executing. Email support is included for two weeks. Ongoing Guide Sessions are available as a separate engagement if you want a thinking partner through the transition itself.

The Trailhead Promise

Start with a free First Look.

15 minutes. I listen first. By the end you'll know whether The Switchback is the right move — and if it isn't, I'll be honest about that.

Book a First Look