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Description
For high-performing professionals considering a significant international career move, whether direct relocation, pursuing a degree abroad, or transitioning to a new market, who want to make a strategic decision that compounds their career rather than interrupting it. This coaching package is designed for professionals at a crossroads: weighing a direct international move, considering a degree abroad, or evaluating multiple pathways into a new market. Over four structured sessions, we will move beyond logistics and spreadsheets to build a clear, honest, and actionable strategy for your move. The goal is a clear decision and a written strategy: which move, why, and exactly how to execute it without losing career momentum. Delivered over four structured 60-minute sessions, concluding with your personal Move Strategy Memo, a written document covering your chosen pathway, the reasoning behind it, and your 90-day execution plan. (Ready to be taken through the entire transition, from decision to signed offer? See The Cross-Border Career Transition.)
What you'll get from this package
A clear, confident decision on which international move to make: direct relocation, degree route, or market transition
A written Move Strategy Memo: your pathway, the reasoning, and a 90-day execution plan
A decision framework you can reuse when circumstances shift mid-move
An honest assessment of each pathway's risks: visa, market, financial, and career-momentum
Clarity on what your target market actually values in your profile, and where the gaps are
Additional details
Coaching delivered via live sessions.
4 x 60-minute 1-on-1 coaching sessions via Leland video call. Move Strategy Memo: a concise summary of your decision, narrative, and action plan. Translation Checklist resource for reframing your experience for a new market. 4-Part Decision Lens Worksheet, a fill-in-the-blank tool for evaluating any international move. Leland Messaging Support: you can message me via Leland between sessions for quick questions (expected response within 48 hours, excluding weekends). Direct, practical, and honest. I won't hand you a relocation checklist: I'll help you make the decision you've been circling, and put it in writing so you stop re-litigating it. Most of my clients are high performers whose instincts stop working when the market, culture, and rules all change at once. That's the gap this package closes.
Payment: upfront before the first session. Scheduling: 24 hours' notice for cancellation or rescheduling. Late cancellations and no-shows will not be rescheduled or refunded. Engagement window: all four sessions must be completed within 10 weeks of the first booking. Unused sessions after 10 weeks are forfeited. Move Strategy Memo: delivered via Leland messaging within one week of the final session. Messaging support: quick questions between sessions via Leland messaging; responses within 48 hours, excluding weekends. In-depth reviews are folded into live sessions. Between sessions: short exercises using the Decision Lens Worksheet. The quality of the final memo depends on the work you put in. Refunds: no refunds after the first session. Unsure if this is the right starting point? Book the Career Crossroads Session first. Upgrade path: if you continue into The Cross-Border Career Transition within 30 days of your final session, $300 of this package's cost is credited.
Services included:
Career Planning
Resume Review
Personal Branding
Networking Strategy
Job Search Strategies
General Exploration
Interview Prep
Skill Building
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
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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.
$650
4h of coaching