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Career Crossroads Session

Career Crossroads Session

Offered by Caolan H.

5.0

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600+ Clients | Global Opportunities | Cross Borders, Cultures, & Mindsets

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Studied at Columbia Business School

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Worked at On running

Description

One 90-minute deep-dive plus a 30-minute follow-up call, for professionals facing a high-stakes decision: relocate or stay, new market or current one, job vs. degree abroad, rebuild after a layoff. The 90-minute session: We map your full situation, what you've tried, what's blocking you, what you actually want (not what you think you should want). We identify which stage of the transition you're stuck at: deciding on the move, positioning for the market, performing in interviews, or landing the offer. We pressure-test your current plan against the realities of your target market. Within 48 hours: You receive a written one-page diagnosis: where you are, what's actually blocking you, and a recommended path forward including whether further coaching would help, and if so, exactly what kind. If the honest answer is "you don't need more coaching, do these three things," that's what the page will say. The 30-minute follow-up (within 2 weeks): Once you've sat with the diagnosis and taken a first step, we reconnect to refine the plan and answer what's come up. This session is for you if you're at a genuine crossroads and want a clear, honest read on your situation before committing to anything bigger, a decision, a move, or a longer engagement.


What you'll get from this package

A written one-page diagnosis of your situation: where you are, what's actually blocking you, and why

Clarity on which stage of your transition needs attention first: deciding, positioning, interviewing, or landing

A recommended path forward with concrete next steps you can act on immediately

An honest read on whether further coaching would help (and if not, I'll tell you)

A pressure-tested version of your current plan, with the weak points identified

A follow-up call to refine the plan once you've taken your first steps


Caolan H.

Offered by Caolan H.

Joined January 2026

5.0

600+ Clients | Global Opportunities | Cross Borders, Cultures, & Mindsets

I help ambitious professionals navigate high-stakes career transitions, from breaking into top companies to stepping into leadership roles. I am the former Global Head of Content at On, where I scaled the brand team from 7 to 35 across three continents and led narrative through a $10B IPO. I now coach executives at Netflix Korea, Woven by Toyota, and Banco Santander. I hold an MFA from Columbia University and speak four languages. Most of my clients already perform at a high level. What brings them to me is the sense that something important is getting lost in translation, culturally more than linguistically. I help them communicate clearly, make confident decisions, and move forward without second-guessing. If your career depends on people in different places understanding you clearly, you are in the right place.

Coaches professionally

Experience level: Executive

100+ people coached for Career Coaching

$250

2h of coaching