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The online business world sells you a dream that doesn't work. Jessica Lackey shares the reality outside of the entrepreneurial casino. We chat about the the real path - the long, hard path - that's often the only way to sustainable success. More from Imperfect Creatives: Substack: https://imperfect.emailYouTube: https://youtu.be/_0FRrrmBAMQInstagram: https://www.instagram.com/imperfect_creativesMore from Jessica: Website: https://www.deeperfoundations.com/Substack: https://substack.com/@jessicalackey Chapters (0:00) How Jessica ended up in the casino (5:48) Why social media stopped working for networking (8:30) Puppy dog internet theory (12:28) Building two businesses at once (17:20) The cost of running a content engine (20:00) Procasti-learning (25:56) Doing the stuff that sucks to do the stuff that sings (28:52) What are you optimising for? (30:28) Delivery vs content business (33:20) Don't force the art to pay the bills (35:06) Step-change functions and limiting factors (41:38) What kept Jessica going in the early years (45:32) The zone of enoughness (50:10) Idea composting (55:14) Roots to fruits (57:46) Signal vs momentum (1:01:14) Niche down, but let the pattern emerge (1:07:22) Playing the long game (1:11:31) Key takeaway & recommendations

Dave Kang spent years trying to figure out his “one thing.” His Ikigai. It didn’t work. Now he's embraced life as a CEO. No, not that kind. A Chief Exploratory Octopus. A generalist with multiple interests (aka tentacles) reaching in different directions, without forcing it all to converge into one neat identity. Now he writes about this on his Substack, helping other multi-talented, multi-interested people break free from the pressure to pick just one thing. Chatting with Dave was an absolute joy, and I left feeling inspired and reassured about being someone with “too many” interests. Chapters (00:00) The Ikigai Lie (03:34) Becoming an Octopus (06:56) Managing Multiple Tentacles Without Overwhelm (11:20) Picking Up and Dropping Rocks (13:40) Breaking Free from Optimization Culture (16:56) The Three Hearts of an Octopus (19:02) Time, Calendars, and Cultural Obsessions (24:50) The Pressure to Monetize Everything (30:02) When Work Kills Creative Passion (31:44) Configuring Your Tentacle Portfolio (36:12) Accomplishment vs. Living True to Yourself (41:46) Destigmatizing Quitting (48:14) Start with "Why Not?" Instead of "Why" (54:10) Embarrassment and Putting Yourself Out There (59:38) Finding Your Tribe and Mentors (1:10:32) Book Recommendations (1:13:56) Final Takeaway More from Imperfect Creatives: Substack: https://imperfect.emailInstagram: https://www.instagram.com/imperfect_creatives More from Dave: Substack: https://davekang.substack.com/ Books Mentioned: The Pathless Path by Paul MillerdThe Great Work of Your Life by Stephen CopeRange by David Epstein4,000 Weeks by Oliver Burkeman

Karin Majoka is a photographer, YouTuber, psychologist, and psychotherapist-in-training, who somehow makes it all work without burning out. We chat about how she balances multiple creative passions with a full-time career, why internal motivation matters more than external validation, and how treating photography as "just one language" opens up creative freedom. As a huge fan of Karin's work this conversation was a pure joy to have and we dove in to much more, from the struggle of overthinking, to the temptation to "pick one thing," and ultimately why experimentation might be more valuable than trying to find your one exact creative style for life. More from Karin YouTube: https://www.youtube.com/karinmajokaInstagram: https://www.instagram.com/karinmajoka/More from Imperfect Creatives: Substack: https://imperfect.emailInstagram: https://www.instagram.com/imperfect_creativesBook recommendations: You Are What You Do by Daniel ArnoldTwilight by Gregory CrewdsonArt Work: On the Creative Life - Sally Mann Chapters (00:00) Balancing Psychology, YouTube & Photography (02:36) Internal vs External Validation as a Creator (05:12) Planning vs Spontaneity (08:08) Searching for Your Style (12:17) Identity: Being Multiple Things at Once (16:14) Why Both Psychology and Art Make You Better at Each (18:39) The "Artist" Label Problem (20:11) Photography is Just One Language (26:34) You Can't Think Your Way Through (28:24) Killing Your Dreams to Actually Live Your Life (30:30) Recovering Overthinkers Anonymous (35:28) Opening Doors vs Shouting at Walls (37:42) Low Expectations, High Purpose (40:09) Creating Under a Pseudonym as a Therapist (43:15) Female Representation in Photography (45:47) The Rise of Authentic "Grandma Content" (48:08) Would Your Work Matter Without Sharing It? (52:01) Doing Your Homework (56:46) Follow Your Curiosity & Experiment (58:51) Book Recommendations

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 IbarraBook: The Second Mountain by David BrooksBook: Transitions by William BridgesConnect with Rick: https://www.thewayofwork.com/https://substack.com/@rickfoersterMore from Imperfect Creatives: Newsletter: https://newsletter.imperfect.club/YouTube: https://www.youtube.com/@imperfect_creativesInstagram: 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 StoriesAri’s Instagram: @admagnussonModern Color by Fred HerzogWilliam EgglestonSunshine Terrace by Emily ShurChapters (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

In this episode, I sit down with Laura aka "Couch Polyglot", a polyglot and YouTuber with over 44k subscribers who creates awesome language learning content whilst also working a day job. We explore how she balances both worlds: maintaining multiple languages as well as a growing channel without burning out.  We dig into practical language learning techniques, why Duolingo might not cut it for serious learners, and how mindset often matters more than natural ability. Laura also shares what it's really like building a YouTube channel, the unexpected challenges of content creation, and her best advice for anyone juggling creative work with a day job. Resources Laura's YouTube channel CouchPolyglot: https://www.youtube.com/@CouchPolyglotLaura's website: https://www.couchpolyglot.comImperfect Creatives Newsletter: https://imperfect.emailImperfect Creatives website: https://imperfect.club Chapters (00:00) Intro(01:03) Starting a YouTube Channel During the Pandemic(03:09) From Teaching to YouTube(09:35) Balancing YouTube and Full-Time Work(13:42) Challenges & Realities of Content Creation(26:20) Mindset and Approaches to Language Learning(34:02) Is Duolingo Effective?(35:48) Starting from Scratch: Learning Basics(37:25) The Importance of Comprehensible Input(38:37) Maintaining and Activating Languages(39:57) Overcoming Language Learning Barriers(42:11) Finding Fun(46:58) Language Tandems (01:02:32) Resources & Recommendations

Elena Mostovova is a product manager and art enthusiast who writes Art for Breakfast, a weekly newsletter making art accessible and relatable to everyone. In this conversation, we explore how art can be a shortcut to understanding culture, why starting with contemporary work beats historical pieces, and Elena's journey from writing a personal art diary to building a public community around her writing. We dig into practical tips for connecting with art without needing an art history degree, how to navigate galleries as a beginner, plus specific gallery recommendations for Berlin and New York, as well as why emotional connection matters more than market value when it comes to both art as well as sharing your own work. Elena's Newsletter: Art for Breakfast - Subscribe on Substack Book Recommendation: Seven Days in the Art World by Sarah Thornton Chapters (00:00) Intro(01:22) Connecting with Culture Through Art(02:58) The Role of Art in Understanding History(05:59) Elena’s Personal Journey with Art(11:19) From Personal Diary to Public Sharing(15:10) Making Art Accessible(17:40) Practical Tips for Engaging with Art(22:52) The Human Side of Art(26:27) Art Collecting(30:16) Supporting Artists Beyond Monetary Investment(32:23) Galleries and Digital Spaces(34:38) Balancing Passion and Professional Life(36:11) Building a Community Through Your Work(43:27) Exploring Art Scenes in Berlin and New York(49:00): Resources & Recommendations

Catt Small is a staff designer who's figured out something most of us struggle with: how to juggle multiple creative projects without burning out. She's written a book, runs online courses, organizes conferences, develops games, and somehow manages to be intentional about where she puts her energy even with all of these competing interests. Also interesting is that Catt climbed to director level as a designer, then consciously stepped back into individual contributor work because she knew what gave her the most energy. We talk about how to build influence without a manager title, why validation matters before you commit hundreds of hours to a project, and how to say no to some projects so you can say yes to the right ones. Plus, practical advice on making the leap from senior to staff level and navigating workplace politics as an Individual Contributor (IC). This one's packed with insights for anyone trying to level up in their day job or figure out how to balance multiple creative projects alongside a demanding 9-5. Resources mentioned Pre-order Catt's fantastic book "The Staff Designer" here: https://rosenfeldmedia.com/books/the-staff-designerCheckout Catt's websiteGame Devs of Color Expo (Sep 16–19, 2025)Catt's Staff Designer courseCatt's book choices: The Crossroads of Should and Must by Elle Luna and Designing Your Life by Bill Burnett & Dave Evans More from Imperfect Creatives Subscribe to the newsletter:⁠⁠ ⁠⁠imperfect.email⁠⁠The website:⁠⁠ imperfect.club⁠⁠⁠⁠Instagram:⁠⁠ ⁠⁠@imperfect_creatives⁠⁠⁠⁠TikTok:⁠⁠ @imperfect.creatives⁠⁠⁠YouTube:⁠⁠ ⁠@Imperfect_Creatives Chapters (00:00): Intro(01:41): Catt's Early Programming Journey(03:31): From Web Dev to Graphic Design(06:05): Navigating Career Choices & Financial Realities(09:44): Evolving Relationship with Work & Side Projects(12:27): Balancing Multiple Projects & Avoiding Burnout(15:52): Saying No & Identity Beyond Projects(20:41): Handling External Perceptions & Self-Awareness(28:14): From Blog to Book(36:03): Staff vs. Management: Leadership & Influence(49:00): Building Influence as a Staff Designer(56:19): Game Devs of Color Expo(59:38): Resources & Final Takeaways

In this episode, I sit down with Paul Hughes, who's career is far from the traditional 9-5, being that he's worked as everything from travelling salesman, military photography, radio host, to now running AFN Europe's radio programming across 15 stations, 8 countries, and 4 timezones. We talk about the struggle of finding work that's truly meaningful, following the spark of excitement in creative work without getting bogged down by the 'score' of ambition, and why putting yourself out there might be the only way forward, even when imposter syndrome keeps whispering that you don't belong. If you've ever decided it's too late to chase something that feels impossible, this conversation might change your mind. Resources mentioned "Awaken the Giant Within" by Tony Robbins - Paul's book recommendation "A Hard Kick in the Nuts" by Steve-O

Dr. Rod Berger has a degree in clinical psychology, has interviewed over 4,000 people, and just wrote his first book "The Narrative Edge", but his real expertise is in finding the human behind the talking points. In this episode, we explore what makes storytelling important, how Rod breaks through people's scripted responses to get to authentic connection, and his philosophy that "if you're not telling your story, someone else is." Rod shares how his "Forrest Gump-like" career of saying yes to unexpected opportunities led him from psychology to refugee work to becoming a master interviewer. We dig into the vulnerable process of writing his first book, why he refuses to ask questions you could find in a press release, and how true presence and authenticity can change everything. Whether you're struggling to find your authentic voice or wondering how to connect more deeply with others, this episode will make you rethink how you show up in your own story. Links for this episode: Dr. Rod Bergers book "The Narrative Edge"Subscribe to the newsletter:⁠ ⁠⁠imperfect.email⁠The website:⁠ imperfect.club⁠⁠⁠Instagram:⁠ ⁠⁠@imperfect_creatives⁠⁠⁠TikTok:⁠ @imperfect.creatives⁠⁠YouTube:⁠ ⁠@Imperfect_Creatives Chapters (00:00) The Journey of Storytelling (05:36) Embracing Opportunities: The Power of Saying Yes (13:43) Crafting Your Own Narrative (22:09) The Art of Authentic Interviewing (30:46) The Addictive Nature of Storytelling (36:52) The Impact of Connection (42:51) The Importance of Being Present (46:56) The Evolution of Storytelling (54:59) Capturing Stories with Integrity (01:00:18) Episode Wrap-Up

What if the biggest breakthrough in your communication isn't about being more persuasive, but about being more curious? Dr. Michael Gerharz, a communication coach with a computer science background, joins me to unpack why so many brilliant ideas die in boring PowerPoint presentations. We dive into his PATH framework (Plain & Simple, Actionable, Transformative, Heartfelt) and explore how empathy beats ego in every conversation that matters. From navigating blunt feedback in tech teams to making presentations that people actually want to listen to, Michael shares practical tools for anyone tired of dancing around topics or watching great ideas get lost in translation. Resources mentioned: PATH in a NutshellSpeak EasyDouglas Adams' The Hitchhiker's Guide to the Galaxy - Michael's book pickPresentation Zen by Gar ReynoldsStay in the loop: Subscribe to the newsletter: ⁠⁠imperfect.emailThe website: imperfect.club⁠⁠Instagram: ⁠⁠@imperfect_creatives⁠⁠TikTok: @imperfect.creatives⁠YouTube: ⁠@Imperfect_Creatives

Orel Zilberman quit his job to become an indie hacker, and then built 9 projects and made… nothing. And then everything changed with his latest product, WriteStack, an AI writing tool now generating thousands in revenue. In this conversation, we dig into the messy reality of quitting your job to be an indie hacker and building in public. Orel shares how customer feedback completely pivoted his product direction, why he spends time daily DMing strangers who engage with his work, and how he balances running WriteStack with maintaining his Substack (the IndiePreneur) where he openly shares his journey every step of the way. Stay in the loop: Subscribe to the newsletter: ⁠⁠imperfect.emailInstagram: ⁠⁠@imperfect_creatives⁠⁠TikTok: ⁠⁠@imperfect.creatives⁠YouTube: ⁠@Imperfect_Creatives⁠ More from Orel: The IndiePreneur (Orel's Substack newsletter) WriteStack Other Resources Mentioned: ⁠The Million Dollar Weekend by Noah Kagan⁠ ⁠David Goggins - Can’t Hurt Me⁠ (Orel’s book choice)

Michael Box is a filmmaker, writer, musician, juggling indie film production with a full-time job and family life. In this conversation, we dig into how he and his creative partner Patrick launched Echo Eterna Productions to create "Speakeasy”, a dystopian film about punk musicians in a world where self-expression is regulated. We talk about time management, writing scripts in parking lots, working with ADHD as a superpower, the emotional vulnerability of putting creative work out there, and more. ✉️ Stay in the loop: Subscribe to the newsletter: ⁠imperfect.news⁠The website: ⁠imperfect.club⁠Instagram: ⁠@imperfect_creatives⁠TikTok: ⁠@imperfect.creativesYouTube: @Imperfect_Creatives More from Michael Box & SpeakEasy: SpeakEasyTheMovie.comInstagram.com/EchoEternaInstagram.com/SpeakEasyTheMovieInstagram.com/MikeWritesMovies Other Resources Mentioned: Craig Maizen’s Scriptnotes podcast Masterclass.com Chapters: (00:48) Wearing multiple hats (01:00) Time management (03:02) Managing ADHD and Staying Motivated (05:47) The Importance of Creative Outlets (06:07) From Music to Filmmaking (10:04) Launching Echo Eterna Productions (17:21) Networking and Collaboration (21:12) Crowdfunding and Production Challenges (28:42) Advice for Aspiring Filmmakers (30:06) The Challenges of Shooting on Film (31:20) The Importance of Collaboration (32:06) Overcoming Creative Obstacles (33:40) Balancing Creativity and Mental Health (38:13) Managing ADHD in Creative Work (45:51) The Influence of Punk Music (53:18) Supporting SpeakEasy

What does it take to walk away from a broken system and build something better? In this episode, I talk to Toni Finnimore, founder of The Social Society, about her journey from “climbing a mountain of treacle” in the charity sector to creating a platform that actually helps people give back in more human, meaningful ways. We talk about founder life, compassion fatigue, and how to actually make a difference when you don’t know where to start. 🔗 Mentioned in this episode: Toni’s org: The Social SocietyThe Alchemist by Paulo CoelhoThe Do Book Co ✉️ Stay in the loop: ⁠Toni on LinkedIn⁠Subscribe to the newsletter: imperfect.newsThe website: imperfect.clubInstagram: @imperfect_creativesTikTok: @imperfect.creatives Chapters: (0:00) Intro (01:22) What Is The Social Society? (04:14) Toni’s Background (08:33) Leaving the Sector vs. Building Something New (11:07) The Reality of Starting From Scratch (13:29) Volunteering That Actually Works: Skills, Not Guilt (17:01) Micro-Volunteering and Making It Frictionless (20:22) Founder Burnout and Setting Boundaries (23:10) Gender Bias in the Founder Journey (26:05) Growing Slow, Staying Rooted (30:41) Balancing Strategy with Intuition (35:18) Rebuilding Local Connection in a Remote World (38:50) Holding Space Without Absorbing Everything (41:55) Starting Small to Beat Overwhelm (45:30) Why Good Events Aren’t About Glitter and Hay Bales (48:00) Finding Purpose in the Chaos (49:38) Final Thoughts and Book Recommendations