The JobQuest Podcast · Don't search for a job. Embark on your job quest!

The wonderful thing about Tiggers

·37 min·2 clips

Justin Dickinson says, "find the thing that makes you one of one."

1. The JobQuest Podcast episode "The wonderful thing about Tiggers" centers on Justin Dickinson's job search and portfolio advice for designers. 2. Justin Dickinson is the guest, a design leader who has worked in front-end coding, product design, management, Vimeo, Namely, and TPT, and host Derek Kang is the founder of JobQuest. 3. The episode asks how a designer can present themselves clearly enough that a hiring manager can see their fit for a specific role. 4. Dickinson says he started in flash websites, doing both HTML and CSS, before moving into product design as the role matured. 5. He describes management as the place where he found his "love and my place," especially in a "player coach" design manager role. 6. He says he was more motivated by helping his team achieve goals than by individual success. 7. Dickinson says his work at Vimeo involved filmmakers, and his time at Namely involved HR software users dealing with taxes, health insurance, and quarter-end reviews. 8. He says he joined TPT in February 2020, launched a digital product called Easel, and worked through a rebrand and restructure as schools moved toward hybrid classrooms. 9. Dickinson says he took time off to write more, meditate, and get back into self-help interests before re-entering the job market. 10. He says the job search then became harder because the market tightened and companies wanted "the exact not unicorn but like the key for the lock." 11. He says he gave a South by Southwest talk titled "your portfolio is garbage" because many portfolios left him with no clearer sense of the candidate than when he started. 12. He says hiring managers are trying to solve a specific approved problem, so candidates should answer that problem instead of presenting "your entire life as a designer." 13. Dickinson says candidates should act like the hiring manager is the user and ask, "what's the problem that you're facing right now?" 14. He says a strong application gives the hiring manager a soundbite, such as "I have scaled teams in a new product of ambiguity while also acting as a player coach." 15. He says his own portfolio once looked too branding-heavy because two of his first five entries contained the word "rebrand." 16. He says he now builds custom PDFs that guide people through his case studies instead of sending one large link. 17. Dickinson says the job search is lonely, so he meets twice weekly with friends who are also looking and shares applications, portfolio feedback, and updates. 18. He says he treats the process more like a qualitative design problem than a spreadsheet, even though one friend tracks applications and interviews in a sheet. 19. The tone is conversational and reflective, with long stretches of practical advice, personal examples, and a few jokes about Nick Fury, Samuel Jackson, and Tigger. 20. Designers, job seekers, and people rebuilding a portfolio after a break will get the most value, while listeners wanting a short celebrity-driven interview can skip it.

As heard by us

A job-search episode that turns portfolio presentation and peer accountability into practical work.

This episode treats a job search as something to clarify, not amplify: what makes a designer distinct, how to shape a portfolio around that difference, and how to stay steady when rejection keeps coming back.

Read the full review in PlayNext →

Why you'd press play

If your portfolio feels invisible, this gives you a cleaner way to show what makes you one of one.

Read the full recommendation in PlayNext →

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from The JobQuest Podcast