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Package Description:
Session 1: Diagnosis (60 min) We map your current situation. What have you tried? What is blocking you? What do you actually want, not what you think you should want. You leave with a clear problem statement and one immediate action. Session 2: Strategy (60 min) We build a decision framework for your specific crossroads (job vs grad school, staying vs moving, corporate vs freelance, etc.). You leave with evaluated options and a strategy, not more confusion. Session 3: Action Plan (60 min) We turn strategy into a 90-day plan with milestones, deadlines, and accountability. You leave knowing exactly what to do next and when. Between sessions: One brief exercise or reflection prompt per week (15–20 minutes). No homework for the sake of homework. Only what moves you forward. This package is for you if: You are stuck between multiple paths and need structure, clarity, and accountability from someone who has been there.
What you'll get from this package
A clear decision framework tailored to your specific crossroads
A 90-day action plan with concrete milestones and deadlines
One immediate action you can take within 48 hours of our first session
Clarity on what you actually want
A way to evaluate future opportunities without getting stuck in analysis paralysis again
Additional details
Coaching delivered via live sessions.
Direct, practical, and focused on action. Most of my clients already perform at a high level. They come to me when they are stuck between options and need someone to help them think without the noise.
Cancellation / Rescheduling: 24 hours notice. Late cancellations or no-shows will not be rescheduled or refunded. Between sessions: You will receive one brief exercise or reflection prompt. Completion is optional. The value you get from this package is directly proportional to the work you put in. Email support: Quick check-ins between sessions (clarifying questions). I respond within 48 hours, excluding weekends. Sessions expire: All three sessions must be completed within 8 weeks of the first booking. Unused sessions after 8 weeks are forfeited.
Services included:
Career Planning
Personal Branding
Leadership
Salary Negotiation
Job Search Strategies
Interview Prep
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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Custom hourly · $133/hr
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Caolan also coaches for Master’s Programs, MBA, Communication & Public Speaking, Marketing, and AI for Sales & Marketing. View all.
Offered by Caolan H.
Joined January 2026
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.
$399
3h of coaching