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.

Firm Leadership Latest
Editorial illustration of a lawyer in a suit sprinting toward a towering pile of gold coins, bars, gems, a crown, and a luxury watch

Why Money Alone Won't Keep Your Best Lawyers

When a deep-pocketed rival comes for your best people, matching the offer is the one lever you are likely to lose. Talent stays for culture, not comp.

July 2026
Read
Partnership Track
A newly promoted partner holding a glass of champagne at a Congratulations New Partners celebration, looking uncertain while colleagues celebrate behind him

Just Made Partner. Why Do I Feel Like I'm Failing?

Partnership is one of a lawyer's biggest milestones, but also one of the least planned-for transitions. Many arrive and think: I made it. Now what?

June 2026
Read
Law Firm Management
A law firm partner analyzing the cost of associate attrition and the ROI of executive coaching

The Hidden Cost of Foregoing Coaching

Coaching is a small cost relative to losing good associates or failing to integrate partners. The long-term impact can justify the investment.

June 2026
Read
Partnership Track
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
Read
Legal Relocation
Lawyer walking down street in asia symbolizing the complex transition of international relocation

The Expat Lawyer's First Year in Asia

For lawyers working abroad, mid-career failure is rarely about aptitude. It usually comes from missing relevant cultural and structural context.

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

Why Brilliant Lawyers Can Fail as Partners

Law firm partners often struggle because the industry equates legal brilliance with leadership capability. Bridging the gap requires a different skill set.

April 2026
Read
Work-Life Balance
Can lawyers have it all

Can Lawyers Have it All?

Work-life balance matters, but treating your career like an on/off switch oversimplifies the reality of working in the legal profession.

February 2025
Read
Personal Reflection
Grappling with middle age

Grappling with Middle Age

Middle age can be perilous, but it can also be a wake-up call: a shift from treating time as infinite to living with more purpose.

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

Setting Goals That Help You Get What You Want

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

August 2024
Read

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.

Schedule a Conversation