Thriving as a UX/UI Freelancer with Jesse Showalter

Episode 387

How can you be successful while wearing many hats?
How do you react to life’s unexpected challenges?

Niching down and focusing on UX/UI has allowed Jesse Showalter, UX/UI designer, educator, YouTuber, and entrepreneur to integrate his passion and his calling into every hour of his life.

This week I want to introduce you to Jesse Showalter. He has been a pastor, designer, creator, vlogger, web designer, dad, husband, freelancer, and now entrepreneur. He has built a YouTube channel based on teaching UX/UI and encouraging others. While building this community organically, he has recently launched a community where there are live monthly meetups to talk about anything that gets in your way as a freelance UX/UI designer.

Jesse loves people and helping others grow. As we focus on Web design this month, Jesse will talk about mindset, people pleasing, client relationships, and so much more.

I hope you’ll join us this Wednesday, August 18th at 7:30pm BST / 2:30pm ET / 11:30am PT / 8:30am in Hawai’i. Sign up to get the link at

You can always join us for the live taping experience and be part of the community. Come a little early and introduce yourself in the chat, tell us where you are located in the world and say hey!  

We start at 7:30pm BST / 2:30pm EDT / 11:30am PDT / 8:30am in Hawai’i on WEDNESDAYS.

Or listen here

Questions for Jesse

  1. Jesse, can you give everybody a little background about your start in design and what you focus on? How long have you been in business and what services do you provide? Who do you normally serve (audience) (customers who watch you on YT and clients)?
  2. You have been growing your YouTube audience and teaching about UX/UI and web design for how long? When did you start creating content on YouTube? What was the focus of content in the beginning and how has it changed now?
  3. How has your business pivoted and changed from when you started?
  4. Has your mission or vision been consistent? What about purpose how has that been refined and revealed to you?
  5. What is your greater purpose? How are you living that out today?
  6. What kinds of lessons have you learned in the last 6 months or year as you have changed from working for a start up to now?
  7. You had a vlog episode about a year ago when you were going on your first vacation in years and you had gone full time on your own freelance? How do you roll with unexpected challenges?
  8. How willing are you in your business and life to take risks? Do you think risk taking is important for an entrepreneur in the UX/UI industry?
  9. We have a mutual friend, Mario Quezada and I saw you at his Mindset Reboot Conference. You talked about some things that really resonated with me that I need to work on. Can you talk about how being a people pleaser has played a role in your business? In your mindset?
  10. At the Mindset Reboot Conference you also talked about starting then staying. Can you go into what that is about a little more and why that has been important? (I also wrote you stayed for a so long in a place without windows, I wasn’t sure if that was metaphorical or not but it is a beautiful image of why you needed to get out.)
  11. You have spoken about the desire we have to be valued and we can get lost when we pin our value on our output. This value and worthiness is something I struggle with personally. Have you dealth with this? How have you overcome it? How do you deal with it?
  12. What is your motivation to build your business?
  13. You also were a part of a mastermind group and you talked about how important it’s been for you to surround yourself with people who encourage you and want you to grow.
  14. Has being a part of that group or other groups made it easier for you to ask for help? For support? For accountability?
  15. What are some of the reasons you’ve started an online community?
  16. How do you recharge? What inspires you?
  17. What is next? Courses launching this fall…

Connect with Jesse

Social Media

Course Info
He is releasing two pretty large courses this year. The first course is an introduction to product design and is still a secret since it’s being launched in partnership with a very large design focused company. It should launch in September and he’s very excited because it’s a huge course that can really help a lot of people who want to get into the digital product design space.

The second course will be releasing around December and is all about becoming a freelance UI/UX designer. It will cover everything from the freelance process Jesse uses to find and book awesome clients to the process of making awesome digital products, and also how to hand those projects off to development teams. To get more information about the course and sign up to get notified when it launched here

Jesse’s Community
He has started an exclusive membership community where his members get access to exclusive content, live streams, meetups & more. He review’s work, mentor, chat with members through office hours and events.

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