The future of work started yesterday, and everyone's scrambling to figure out what's next. Join Milly and Lindsey, as they build Generalist World and ask the quiet questions out loud. Generally Curious is the show where the minds shaping tomorrow's workforce gather to swap notes, learn, teach, shortcut, and predict. And now, you have a front-row seat! Each episode is no-nonsense, packed with answers to the questions you need to know to navigate an ambiguous future. Subscribe now for meaningful conversations that equip you with actionable strategies for your career.

In this episode of Generally Curious, we sit down with Libby DeLana, a creative powerhouse known for integrating her passions and experiences into a multifaceted career. Libby's approach to life and work exemplifies the generalist mindset, seamlessly blending roles as a co-founder, author, and designer with her unique practice of mindful walking. We'll explore how Libby's diverse interests and insatiable curiosity have shaped her path, offering insights into the value of embracing a wide range of experiences in both personal and professional spheres. If you're interested in how diverse career experiences can enrich your life and work, and how simple daily practices like walking can inspire creativity and clarity, this conversation with Libby is for you. Join us to hear more about living intentionally, staying curious, and finding inspiration in every step.

Introduction (00:00:01)

Introducing the podcast and its purpose, setting the stage for the conversation.

Libby's Diverse Career (00:02:28)

Libby discusses her career journey, the value of diverse experiences, and the role of curiosity and creativity in her professional life.

The Beginning of Intentional Walking (00:07:23)

Libby shares the pivotal moment that led her to start her intentional walking practice and its significance in her life.

The Transformative Power of Walking (00:12:47)

Libby shares a powerful personal story of how walking helped her navigate a challenging life event and how it has become a tool for understanding emotions.

Accessibility and Democratic Nature of Walking (00:19:09)

The accessibility and universality of walking as a practice are discussed, emphasizing its democratic and inclusive nature.

The keys to walking (00:20:30)

Libby discusses the analogy of online gaming to explain the access and lessons gained from years of walking.

Influencing change in the creative industry (00:21:36)

Milly asks Libby for advice on influencing change and inclusivity in the creative industry and leadership roles.

Authenticity and bravery in the workplace (00:22:07)

Libby emphasizes the importance of showing up authentically and bravely in the workplace to influence change.

Building confidence to find your voice (00:24:44)

Libby shares advice on finding confidence and support to speak up in a professional setting.

Social responsibility and cultural impact (00:27:12)

Libby discusses the role of companies in creating cultural impact and social change through their messaging and actions.

Navigating career paths and following passion (00:30:25)

Libby shares her perspective on navigating career paths by following what excites and energizes us.

The power of storytelling and community (00:38:31)

Milly and Libby discuss the power of storytelling and community in inspiring and helping people at scale.

Defining generalists (00:39:42)

Libby defines a generalist as having broad knowledge with a splash of exquisite curiosity.

The impact of note-taking in career journey (00:40:07)

Libby shares the outsized difference note-taking has made in her career journey.

The joy of being around generalists (00:41:48)

Libby highlights the fun and resourcefulness of generalists, emphasizing their ability to connect dots and contribute to conversations.

Exploring Diverse Career Experiences (00:43:03)

Milly, Lindsey, and Libby discuss Libby's varied career experiences and the value of integrating personal passions into work.

The Transformative Power of Intentional Walking (00:43:09)

Libby shares insights from her book "Do Walk," emphasizing the transformative power of intentional walking and its impact on understanding emotions.

In this eye-opening episode of Generally Curious, hosts Milly and Lindsey delve into the multifaceted world of entrepreneurship with Ash Phillips, the Founder and Chair of Rebellious Co.

With a career spanning over a decade, Ash shares the patterns of success and common pitfalls he's encountered in his journey. From building and scaling companies to navigating the uncertainties of entrepreneurship, Ash provides deep insights into the risk management frameworks that have guided his path. As an angel investor, he also sheds light on what investing has taught him about business and life.

Furthermore, Ash, a renowned speaker, shares invaluable advice for aspiring speakers on becoming more confident on stage and landing both their first and bigger gigs. This episode is a must-listen for anyone interested in entrepreneurship, leadership, and the unique blend of skills that drive innovation and success in the business world. Join us as we explore Ash's dynamic career, his contributions to the UK startup ecosystem, and the invaluable lessons he's learned along the way.

Fun Fact: Ash introduced Lindsey + Milly, so this podcast quite literally would not have existed without Ash 👏

The introduction (00:00:01) Milly and Lindsey introduce the podcast and its purpose.

Introducing Ash Phillips (00:00:59) Ash Phillips' background and accomplishments are introduced, focusing on his impact in entrepreneurship and leadership.

Insights into entrepreneurship (00:02:12) Ash Phillips' insights into entrepreneurship, leadership, and innovation are discussed, along with patterns of success and common mistakes.

Patterns of success (00:03:41) Ash Phillips discusses the patterns of successful people and the role of confidence.

Common mistakes in business (00:07:07) The discussion shifts to the common mistake of focusing too much on small details and neglecting the importance of selling in business.

Career and self-reflection (00:09:45) Ash Phillips reflects on his career path, self-awareness, and the importance of taking life one step at a time.

Internal work and risk in entrepreneurship (00:13:23) The conversation delves into the internal work required for entrepreneurship and the tolerance for risk and uncertainty in building companies.

Objective vs. Holistic Approach (00:18:31) Ash discusses intuition and gut feel in decision-making, emphasizing the importance of subjective and objective approaches.

Evaluating Risk and Fiscal Management (00:21:14) Ash explains the importance of evaluating risk and fiscal management, providing insights into using mathematical analysis for risk assessment in business.

Angel Investing and Founder Market Fit (00:22:41) Ash shares his experiences and insights into angel investing, emphasizing the significance of founder market fit and subjective evaluation in early-stage investments.

Getting Started in Angel Investing (00:26:51) Ash provides tips for individuals interested in angel investing.

Becoming a Confident Speaker (00:29:31) Ash offers advice on becoming a more confident speaker, emphasizing the importance of having a common theme and understanding that most people in the audience may not care.

Energy and Engagement in Speaking (00:33:57) Milly discusses the importance of bringing energy and humor to speaking engagements.

The unique perspective (00:35:37) Discussion on the power of combining unique perspectives in entrepreneurship and the value it brings to the industry.

Bento box time management (00:39:24) Explanation of a time management strategy using a visual representation of time allocation, known as a bento box.

Spinning plates (00:41:37) Ash Phillips provides an overview of the different projects he is working on and how they intersect or operate independently.

Lightning round questions (00:44:17) Quick-fire questions about defining a generalist, the impact of social media on career journey, and the potential of generalists in the world.

Conclusion (00:47:13) Closing remarks and gratitude.