Understories 004: Linds + Kat, Q&A With Cloudfields

This week is the last week before we all disappear for the holidays, so just for fun, we turned the tables and my brilliant colleague Kat interviewed me.  We dive in to the last nine months of working together, the challenges of 2023, how I work, what my plans are and what the future just might hold. It’s always great to chat with Kat, and was fun to reflect on the year together and our experiences so far.



In this conversation, Lindsay and Kat reflect on the past year of working together and discuss the challenges and growth they have experienced. Lindsay shares how she has conquered fears and become more focused on the future of the business. They also discuss the importance of dedicating time for reflection and the desire to write a book. Lindsay reveals her favorite pillars of working with creative businesses, including finance and the big picture. They emphasize the importance of empathy when presenting financial information to clients. In this conversation, Lindsay and Kat discuss the importance of making decisions and moving forward, being patient and empathetic in decision-making processes, and the role of risk and decision-making in business success. They also explore the unique application of the audit process to evaluate and improve creative businesses, the challenge of lead generation, and the vulnerability of putting creative work out into the world. They discuss the need to zoom in and zoom out in business thinking, the journey of starting a business, and the importance of following curiosity and not worrying about career trajectory. They reflect on past disappointments and the positive outcomes that can arise from them, expressing gratitude and looking forward to the future.


  • Reflecting on challenges and growth can provide valuable insights and help in planning for the future.
  • Dedicating time for reflection and writing can lead to clarity and new ideas.
  • Finance is a crucial pillar in understanding the health and potential of a business.
  • Empathy is essential when presenting financial information to clients, as it can be a sensitive and personal topic. Make decisions and move forward, evaluating and adjusting as necessary.
  • Be patient and empathetic with others who are struggling to make decisions.
  • Embrace risk and be comfortable with the possibility of failure.
  • Use the audit process to evaluate and improve creative businesses.


00:00 Introduction and Recap
01:00 Reflecting on the Past Year
05:19 Feeling Grounded and Confident
08:01 Dedicating Time for Reflection
12:28 Writing and the Desire to Write a Book
18:16 Favorite Pillars: Finance and Big Picture
22:41 The Importance of Finances
25:46 Empathy in Presenting Financial Information
26:49 The Importance of Making Decisions
27:36 Being Patient and Empathetic in Decision-Making
28:16 The Role of Risk and Decision-Making in Business Success
28:52 The Audit Process and Its Unusual Application to Creatives
30:27 Using the Audit Process to Identify Potential and Build a Vision
31:34 Asking the Right Questions and Focusing on the Main Problem
32:16 The Reward of Helping Clients Discover Their Potential
33:21 Applying the Audit Process to Evaluate and Improve
34:29 Continuously Improving and Tweaking the Audit Process
35:28 The Challenge of Lead Generation for Creative Businesses
36:45 The Vulnerability of Putting Your Work Out There
37:14 The Need to Zoom In and Zoom Out in Business Thinking
38:24 The Difficulty of Balancing Different Pillars in Business
40:25 The Unique Experience of Being a Creative Business
45:12 The Journey of Starting a Business and Building Something Special
48:53 Following Curiosity and Not Worrying About Career Trajectory
49:47 Realizing That Things Tend to Work Out
51:09 Reflecting on Past Disappointments and Seeing the Positive Outcomes
52:01 Expressing Gratitude and Looking Forward to the Future