Rick Foerster spent 12 years at a healthcare startup, from early employee to public company exec managing hundreds of people. He built the network. He accumulated the war chest. He had 100+ company ideas ready to go. He was standing at the starting line of what he thought was his entrepreneurial dream.

Then he “went dark”.

What was supposed to be a three-month sabbatical turned into two years of what Rick calls "the wilderness phase". No networking, no building. Rick wanted to figure out who he was when he wasn't on the hook to do anything.

Now he’s writing post-apocalyptic fiction, has a completely different relationship with work, and believes most of us need to get lost before we can actually find anything worth doing.

We talk about why his executive coach told him to disappear, what led him to writing about his experiences on Substack, the trap of suppressing existential questions with productivity, the "first mountain vs. second mountain" framework, and why following weird creative interests matters more than having a plan.

Resources mentioned:

• Rick's Substack: https://www.thewayofwork.com/
• Book: Working Identity by Herminia Ibarra
• Book: The Second Mountain by David Brooks
• Book: Transitions by William Bridges

Connect with Rick:

• https://www.thewayofwork.com/
• https://substack.com/@rickfoerster

More from Imperfect Creatives:

• Newsletter: https://newsletter.imperfect.club/
• YouTube: https://www.youtube.com/@imperfect_creatives
• Instagram: https://www.instagram.com/imperfect_creatives
• LinkedIn: https://www.linkedin.com/in/michael-carruthers/

Ari Magnússon is a fantastic photographer and writer whose newsletter 'One Lens, Too Many Stories' explores borders, identity, and what it means to belong. He's lived in seven countries, holds three passports, and is now based in Berlin where he's documenting his neighbourhood one frame at a time.

In this conversation, we talk about what that split identity actually feels like — growing up between Iceland and the UK, restarting from scratch in Montreal, and eventually landing in Berlin. We also get into why he shoots Leica (including the cost), how he developed his photographic style, and what he's actually trying to achieve with his work.

Links & Resources

• Ari's Newsletter: One Lens, Too Many Stories
• Ari’s Instagram: @admagnusson

• Modern Color by Fred Herzog
• William Eggleston
• Sunshine Terrace by Emily Shur

Chapters

• (0:00) Intro
• (0:57) Writing vs Photography
• (2:55) Living Across Seven Countries
• (5:45) Cultural Identity and Belonging
• (7:11) Exploring Borders Through Photography
• (12:22) Photography Philosophy and Purpose
• (26:47) Building a Body of Work & Editing Process
• (29:58) Making a Living as a Photographer
• (32:50) Moving to Berlin
• (34:47) Camera Shyness and Street Photography
• (38:58) Ethics and Motivation in Photography
• (41:47) Developing Your Own Style
• (46:47) Film vs Digital Photography
• (51:47) Final Thoughts and Recommendations

What happens when you chase your entrepreneurial dream for four and a half years and then realize it's not actually what you want?

In this episode, I sit down with Jacob O'Bryant, creator of The Sample (now Yakread), to talk about his journey from quitting his job in his early twenties to going all-in on building his own products, only to discover that entrepreneurship wasn't the path he thought it would be. Jacob is refreshingly honest about the psychological toll, the gradual realization that he valued invention over business-building, and why going back to a full-time job wasn't defeat, it was clarity.

We also explore the framework that sits between pure research and entrepreneurship: invention. It's a way of thinking about your work that doesn't require monetization or academic rigor, just meaningful exploration. Plus, we dig into unbundling social media: what it means, why it matters, and practical steps you can take as an everyday person to support a more open internet. If you've ever wondered whether the "quit your job and start a company" narrative is really for you, this conversation might give you a different perspective.

Resources Mentioned:

• Jacob's website: https://obryant.dev/
• Jacob's "Invention" resource page: https://obryant.dev/invention/
• Jacob's product: https://yakread.com/
• Jason Crawford's "We Need a Career Path for Invention" essay: https://blog.rootsofprogress.org/a-career-path-for-invention
• "You Can Help Unbundle Social Media": https://obryant.dev/p/you-can-unbundle-social-media/
• "Wherever you get your podcasts is a radical statement": https://www.anildash.com//2024/02/06/wherever-you-get-podcasts/

Chapters:

• (00:00) Intro
• (01:40) Being a "Recovering Entrepreneur"
• (04:30) College Was a Waste
• (07:00) The Initial Itch: Ambition and Meaningful Work
• (09:20) Planning the Leap: Money, Marriage, and Runway
• (14:50) The Sample and Yakread
• (19:10) Not Going All In Again
• (21:00) Invention is Between Research and Business
• (26:30) The First Months: Euphoria to Reality
• (29:30) Why You Shouldn't Monetize Your Passion
• (31:15) Hustle Culture vs. The Messy Middle
• (34:00) Going Back to a Day Job Wasn't Defeat
• (36:30) How Entrepreneurship Changed Jacob's Work
• (38:30) Job Searching with Entrepreneurship on Your Resume
• (42:30) Unbundling Social Media
• (46:00) What Everyday People Can Do About It
• (51:10) Final Takeaway and Resources