Whittaker Coaching

Insights

Essays on leadership transition, partnership strategy, and the realities of building a career in law and finance — particularly in cross-cultural environments.

Partnership Track Latest
A lawyer sitting alone at his desk at night, head in hands, weighed down after being passed over for partner

You've Been Passed Over for Partner. Here's Why

Being passed over for partner is rarely about legal ability. It is about sponsorship, firm fit, and a business case you have to build deliberately.

May 2026
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Legal Relocation
Lawyer walking down street in asia symbolizing the complex transition of international relocation

The Expat Lawyer's First Year in Asia: What You Should Know That People Don't Tell You

For lawyers working abroad, failure at the mid-career level or above isn't usually due to aptitude. It's caused by not fully appreciating relevant cultural and structural contexts.

April 2026
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Leadership Transition
Law firm partner sitting alone in a corporate office, reflecting on the isolation of leadership transition

The Brilliant Lawyer, The Failing Partner: Why Legal Excellence Doesn't Translate to Leadership

The primary reason law firm partners struggle with management is that the industry equates legal brilliance with leadership capability. Here's how to bridge the gap.

April 2026
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Work-Life Balance
Can lawyers have it all

Can Lawyers Have it All? Maybe with a Little Remastering.

Work-life balance is a fallacy. Not because it doesn't matter, but because the idea that your career should function like an on/off switch oversimplifies the reality of working in the legal profession.

February 2025
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Personal Reflection
Grappling with middle age

Grappling with Middle Age: Reflecting on What I've Seen and Learned Thus Far

Middle age can be perilous, but it can also be a wake-up call. Reflecting on the transition from viewing time as infinite to recognizing the urgency of living with purpose.

January 2025
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Personal Development
Setting goals that help you get what you want

Setting Goals That Actually Help You Get What You Want

A practical guide to setting goals that actually lead to the life you want, using the PARCS framework to overcome disillusionment and make tangible progress.

August 2024
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Work Together

If this is on your mind,
I'm happy to think it through with you.

ICF-certified executive coach, Harvard Law graduate, and Asia-based leadership consultant. I help lawyers and executives navigate the transition from expert to leader.

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