Episode Overview

Title: Squiggly Shortcut: 5 Questions That Will Transform Your Career Conversations
Host: Sarah Ellis (with Amazing If / Squiggly Careers)
Release Date: January 15, 2026

This Squiggly Careers “Shortcut” episode focuses on five powerful questions designed to transform the way you approach career conversations. Whether preparing for a one-to-one discussion with your manager, coaching yourself, or simply taking stock at the start of the year, Sarah shares practical ways to deepen reflection and unlock new possibilities in your professional life.

Key Discussion Points & Insights

Introduction: Using Career Questions to Spark Change

[00:34]

• Sarah frames the episode as a quick, actionable tool for “useful career conversations.”
• The five questions are versatile: for prepping career chats, team management, self-coaching, or fresh-start New Year reflection.
• Sarah notes the power of “zooming out” to reflect on the big picture before zooming back into everyday work.

1. What do you want to be true in 12 months’ time that isn’t true today?

[01:05]

• Encourages “mental time travel”—imagining life a year from now to inspire change and set new goals.
• “This typically tends to be about doing something for the first time, so something new and being a beginner or making a change.” (Sarah, 01:23)
• Tips for brainstorming:
  • Jot the question down and do a three-minute mind-map.
  • Don’t force answers; go for a walk to let thoughts flow.

2. When do you feel most fulfilled in the work that you do?

[02:09]

• Focuses on identifying what energizes you—work activities, moments, or team dynamics.
• “If I was answering this, I would talk about kind of creating with my co-founder... solving problems together.” (Sarah, 02:16)
• Prompts:
  • Frequency of fulfillment—are you leveraging your strengths enough?
  • Look beyond your job; consider team or industry context.

3. Which confidence gremlin gets in your way the most at work right now?

[02:49]

• Addresses limiting beliefs (“gremlins”) like imposter syndrome or fear of conflict.
• “It's very rare that they're there shouting really loudly all of the time. So can you spot the specific situations?” (Sarah, 03:34)
• Strategies:
  • Identify specific triggers and contexts.
  • Invite others to help support or “cage” your gremlins.

4. What are you curious to learn more about in the next three months?

[04:10]

• Focuses on short-term curiosity for actionable growth.
• “I shared actually on LinkedIn this week: I’m really curious to learn more about systems thinking... but I see it pop up in lots of different places.” (Sarah, 04:28)
• Choose one topic that intrigues you—keep goals manageable.

5. If you weren’t doing what you do today, what opportunities or possibilities would you like to explore?

[05:13]

• Encourages creative, open-ended thinking about alternatives beyond your current career identity.
• “Just really thinking creatively and just imagining the different roles, maybe different organizations.” (Sarah, 05:24)
• Tip: Try the “scanning” exercise—collect data from various job descriptions for inspiration.

Notable Quotes & Memorable Moments

• “Learning has never been more important at work, but it’s also never felt harder to do. And we think that lobsters are the role models that we've all been missing.” (Host, 00:12)
• “If you find any of these questions a bit daunting or intimidating… set yourself a timer for three minutes and do a three minute mind map… just to warm up your thinking.” (Sarah, 01:30)
• “Often other people might have ideas or even they might just be able to support you in those moments where that gremlin is sort of shouting loudly.” (Sarah, 03:57)
• “Helen and I actually asked ourselves that question last week… actually once we got started, we could think of loads of other things, and that's despite the fact we really love what we already do.” (Sarah, 05:39)

Timestamps for Important Segments

• [00:34] – Introduction to the five questions and how to use them
• [01:05] – Question 1: 12 months from now
• [02:09] – Question 2: Fulfillment at work
• [02:49] – Question 3: Confidence gremlins
• [04:10] – Question 4: Learning curiosity
• [05:13] – Question 5: Exploring new possibilities
• [06:12] – Recap of all questions and invitation for listener feedback

Final Thoughts

Sarah closes the episode by encouraging listeners to try these questions in any career context—whether mind mapping, discussing with a manager, or talking with friends. She invites listeners to connect and share their own favorite career questions. The tone throughout is practical, encouraging, and supportive, empowering listeners to take simple, meaningful steps toward their own career development.

“Whether you’re mind mapping, having a career conversation with your manager, going for a walk and talk with a friend... I hope you are finding these squiggly career shorts useful.” (Sarah, 06:26)