Taking the leap from being a successful attorney in the city to a financial advisor in the Berkshires would have daunting to many. But for Matthew Chester it was all about actually building a real relationship with his clients, something missing in the narrow focus of being a specialized financial attorney in New York City. As his career path shifted, so did his personal life, as he and his wife Catherine are raising two young daughters Leah and Zoe at home in Stockbridge. In our conversation we cover Matt’s decision to shift from law to financial advising, his time in Taipei, Mandarin as a second language, sunk cost, psychology in investing and finances, inflation, the housing market, the permanent and not-so-permanent changes post-pandemic, wages, labor vs. corporate profits, corporate responsibility, college planning, retirement, Malcolm Gladwell’s research of dynamics in elite colleges, 529 plans, the origin of the name: Tableaux, the Levi Strauss principle, growing up near Seattle, his pull to the East Coast, meeting his wife at Cardozo Law School in NYC, work/life balances in the Berkshires, fatherhood, the art of parenting, how financial advisors get paid, broker model vs. investment advisor, and more. I hope you enjoy my conversation with Matthew Chester.