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To round off the year, we speak to James Lewindon, Head of Client Development UK at Pinsent Masons Vario, the global law firm and alternative legal services provider. Although he started out as a history teacher, James has built a strikingly varied, ‘squiggly’ career: from working for a newspaper and entrepreneurship skills programmes in schools, to leading a science centre team building exhibits, moving into management consulting within a global law firm, launching and scaling a legal resourcing business, serving as a CEO in a legal employment and training business, to now joining Pinsent Masons Vario in 2025. James’ story shows us that a long-term career plan isn’t always essential for a fulfilling career. Driven by a fear of “Groundhog Day,” James moves on when the sense of challenge fades, shaping a path that plays to his strengths and preferred environments. Rather than pursuing a fixed-end career goal, he prefers to seek roles that offer stability, but also the space to grow, learn, experiment, and create. In this episode, we also explore imposter syndrome, the experience of redundancy, and the power of asking your network for feedback and support along the way. 00:00 Introduction and Guest Welcome 01:13 James's Early Career as a History Teacher 06:23 Realization and Decision to Leave Teaching 10:54 Exploring New Career Paths 19:12 Transition to Project Management and Beyond 27:43 Exploring Diverse Career Paths 28:12 Transitioning to the Legal Industry 30:07 Building a New Legal Platform 31:18 Facing Career Barriers in Law Firms 32:35 Considering a Career Change 34:03 Embracing Career Flexibility 34:40 Navigating Job Titles and Roles 36:02 Finding the Right Career Fit 39:30 The Importance of Security and Change 47:34 Reflecting on Career Choices 53:16 Seeking Help and Embracing Vulnerability 57:19 Final Thoughts and Advice