Working With Designers

The Truth About AI and the Future of Design Work

AI isn’t coming for your job—but it is changing how designers work. In this episode of Working With Designers, we unpack the real impact of AI on creative work, design strategy, and client expectations. Jake and Kristin explore how AI tools like ChatGPT and Canva are showing up in real projects, what designers should (and shouldn’t) worry about, and how to navigate the shifting landscape of originality, ownership, and value. Whether you’re using AI to write proposals, polish emails, or speed up mockups, the message is clear: your value isn’t in what you make—it’s in how you think. In this episode * How clients are misunderstanding AI’s capabilities * The best use cases for AI in a design workflow * Why taste, strategy, and curation matter more than ever * What new designers should not worry about * The legal and ethical gray areas of AI-generated work Chapters 00:00 Strategic Design vs. Production 01:39 AI in Creative Work 04:14 Understanding AI Tools 06:33 Communication and AI 09:00 Client Expectations with AI 11:30 The Accessibility of Design 14:07 Legal Implications of AI Generated Content 17:58 The Challenges of AI in Art and Copyright 19:50 The Rise of Handcrafted Art in a Digital Age 20:17 AI's Role in Communication and Professionalism 23:42 AI as a Tool for Brainstorming and Mental Health 26:59 AI: A Reactor, Not a Collaborator 29:42 The Future of AI and Copyright Issues 30:57 The Value of Human Curation in a Digital World 35:44 Navigating the Pressure of AI in Design 40:32 The Efficiency of AI in Creative Processes 48:56 The Impact of Social Media on Creativity and Comparison 50:24 Navigating Social Media's Impact 53:01 The Homesteading Trend: A Cultural Reflection 01:00:57 The Future of AI and Marketing 01:06:45 Authenticity in Marketing and Content Creation

Beyond the Portfolio

Kristin Silva and Jake Cooper dive into the realities of running a creative business—from strategic networking and portfolio challenges to marketing, sales, and client management. They reflect on local creative communities, the pitfalls of bad industry advice, and the tech gaps small businesses face. The conversation highlights the balance between strategy and execution, the evolution of design expectations, and the value of building habits, community, and sustainable creative practices. ‍ 00:00 – Networking Events and Community Building 06:06 – The Value of Networking and Building Relationships 12:02 – The Importance of Strategic Networking 15:01 – Advice on Portfolio and Case Studies 27:12 – Balancing Depth and Simplicity in Portfolios 32:58 – The Gap in Tech Solutions for Small Businesses 39:03 – Rented vs. Owned Audiences in Marketing 50:59 – The Balance Between Creative Execution and Strategy 01:04:54 – Navigating Career Milestones and Creative Blocks 01:47:58 – Sales Strategies and Portfolio Management

"It's On Us to Dictate This"

Summary In this episode, Jake and Kristin dive into the messy, meaningful side of client work—where strategy meets real talk. They unpack the importance of setting expectations early, owning the process, and leading clients with clarity and confidence. From subscription models and value-based pricing to design briefs and project pivots, they share hard-earned lessons from the trenches. It’s a candid conversation about when to push, when to listen, and why it’s up to us—the creatives—to steer the ship. Takeaways Here’s the deal: if you’re not leading your projects, your clients definitely will—and that’s how good work goes off the rails. This episode is a reminder that it’s on us, as designers, to set the tone, define the process, and hold the line. That means crystal-clear briefs, real talk about strategy, and pushing back when things get fuzzy. Subscription models? They’ll eat you alive without boundaries. Value-based pricing? Useless if you’re afraid to talk about risk. The takeaway? Take control, stay accountable, and stop waiting for permission to lead. ‍ 00:00 — Intro 04:13 — Navigating Client Relationships and Design Tests 08:46 — Subscription Models: Pros, Cons & Pitfalls 15:00 — Strategy vs. Execution: Finding the Balance 28:08 — Why Design Briefs Matter (More Than You Think) 38:30 — Client Communication: Say It Early, Say It Often 49:58 — Owning Accountability in Your Creative Business 56:48 — Value-Based Pricing: What It Really Takes 01:12:12 — Pricing Models and Managing Risk 01:24:00 — Setting Expectations (Before They Set You) 01:29:27 — Outro ‍ Keywords creative business updates, managing client relationships, design process testing, design project workflows, subscription pricing for designers, retainer models for creative services, brand strategy implementation, client communication strategies, writing effective design briefs, educating design clients, professional development for designers, creative project management, accountability in client work, creative business strategy, value-based pricing for creatives, managing pricing risk, delivering impactful design, self-reflection in creative work, setting client expectations, boundaries in design projects, design feedback and iteration, scope creep management, onboarding design clients, creative services pricing models

Navigating Creative Partnerships

Summary In this episode of 'Working with Designers', hosts Jake Cooper and Kristin Silva engage with Sean Clancy and Elina Picciocca, co-founders of Space Out Design. They discuss the realities of creative partnerships, the journey of starting a design studio, navigating roles and responsibilities, client relationships, and the challenges of transitioning to full-time freelancing. The conversation emphasizes the importance of financial strategies, mental health, and the design of one's life in the creative industry. In this conversation, Elina Picciocca, Jake Cooper, and Kristin Silva discuss the intricacies of managing a creative business, focusing on project processes, time estimation, financial goals, and the balance between work and personal life. They share insights on overcoming burnout, the transition from designer to business owner, and the importance of community support. The discussion also touches on productivity strategies, the role of music in creativity, and the necessity of setting boundaries to maintain a healthy work-life balance. Takeaways * Creative partnerships can enhance productivity and creativity. * Navigating roles in a partnership is essential for success. * Client relationships require clear communication and boundaries. * Taking the leap into full-time freelancing is a significant decision. * Financial strategies are crucial for sustaining a freelance business. * Mental health plays a vital role in the creative process. * Underestimating project hours can lead to burnout. * It's important to find a balance between work and personal life. * Designing your life is as important as designing for clients. * Having a safety net can ease the transition into freelancing. We start breaking down every single project. * We overestimate our ability to work fast. * You have to do research and talk to the client. * You have to have that kind of awareness. * We figured out if we put our goal, we complete the goal on 70%. * We start structured, but we spent like we weekend at least at the week we not work. * You have to love the graphic design. * Don't undercharge, price is self-perfectly. * We went year and a half without day off. * We start doing boundaries. Chapters 00:00 Creative Partnerships and Business Beginnings 10:27 Balancing Full-Time Jobs and Entrepreneurship 15:03 The Dynamics of a Business Partnership 36:47 The Intersection of Law and Design 40:36 Taking the Leap: Transitioning to Full-Time Freelancing 54:48 Finding Balance: Mental Health and Work 59:54 Designing Your Life: The Business of Freelancing 01:15:01 Navigating Burnout in the Creative Industry 01:25:04 Finding Creative Flow and Productivity Hacks 01:48:07 Wrap-Up and Outro Learn more Spaceout Design spaceoutdesign.com [spaceoutdesign.com] Studio Quiche studioquiche.com [studioquiche.com] Jake Cooper Design jakecooperdesign.com [jakecooperdesign.com] Working With Designers workingwithdesigners.com [https://workingwithdesigners.com/] Keywords creative partnerships, design studio, freelancing, client relationships, business strategies, design process, mental health, collaboration, entrepreneurship, design industry, project management, creative process, time estimation, financial goals, work-life balance, burnout, design business, pricing strategies, community support, productivity

To Niche or Not To Niche?

This episode of Working With Designers explores the complexities of niching as a creative professional, including when it's beneficial, when it’s limiting, and how to balance specialization with flexibility. Jake Cooper and Kristin Silva break down real-world experiences, industry misconceptions, and strategies for making the best decision for your business. 00:00 – Weekend Reflections 03:03 – The Challenge of Niching 08:23 – Why Audience Focus Matters 13:30 – Defining Niching & Its Benefits 18:48 – Personal Experiences with Niching 24:05 – From Niche to Portfolio Building 29:12 – Specialization vs. Generalization 38:36 – Strategy & Visual Design Reflections 50:15 – Understanding Value in Design 54:20 – Niche Marketing & Client Education 01:03:54 – Defining Your Unique Value 01:14:05 – The Portfolio Dilemma 01:16:22 – Branding vs. Marketing 01:28:50 – Final Thoughts on Niching