Squiggly Shortcut: 4 Questions to Help You Make a Difficult Career Decision

Podcast: Squiggly Careers
Hosts: Helen Tupper (Amazing If)
Date: October 16, 2025
Episode Type: Squiggly Shortcut (short, action-focused)

Episode Overview

This concise Squiggly Shortcut episode, hosted solo by Helen Tupper, explores how to approach difficult career decisions—an inevitable part of modern, “squiggly” (non-linear) career paths. Helen offers a practical four-part framework aimed at helping listeners gain clarity, separate fact from feeling, and take actionable steps toward a confident decision.

Key Discussion Points & Insights

1. The Challenge of Difficult Career Decisions

• Squiggly careers involve frequent change and decisions—sometimes by choice, sometimes by circumstance.
• Difficult decisions are challenging due to self-doubt, fear of making the wrong move, or feeling stuck.
• Over-reliance on others’ opinions can be problematic:

  “The problem with that is it's not their career. And I also don't want you to feel stuck in a situation. So, we need to take more ownership.” (Helen, 01:40)

2. The Four-Part Framework

Step 1: Distance

• Gain perspective by imagining your life five years from now, focusing on your “perfect day or week.”
• Questions to consider:
  • Who are you with?
  • What are you working on?
  • Where and how are you working?
  • How do you feel?
• Connect today’s decision with your envisioned future to see which option brings you closer to it.

  “We’re just trying to zoom out from where you are right now to this ideal future state and see whether that creates any clarity for you.” (Helen, 02:14)

Step 2: Data

• Balance emotions with objectivity.
• Exercise: Divide a page in two; list facts on the left, feelings/concerns on the right.
• This process highlights whether facts or emotions are dominating and helps “tame” emotional reactions.

  “If you can name the emotion, it is much easier to tame the emotion.” (Helen, 03:29)

• Simply writing things down can help manage overwhelm.

Step 3: Discussion

• Speak to at least two people:
  • Someone who’s done it: Ask about their thought process and reflections.
  • Someone who’s doing it: Ask about their feelings, considerations, and factors influencing their approach.
• Avoid asking “What would you do?”—aim to gather insights, not outsource your decision.

  “We're not asking them, 'What would you do?'… We're not doing that. The person that's done it, ask them, what was your thought process? How did you reflect on it now?” (Helen, 04:18)

Step 4: Drivers

• Reflect on your intrinsic motivations—understand your “why.”
• Clarity on what drives you fuels resilience (“grit”) and helps sustain your commitment even if the decision remains hard.

  “Understanding the why behind what you are trying to do will grow your grit.” (Helen, 05:21)

Notable Quotes & Memorable Moments

• On Ownership:

  “We don’t know what the right thing is to do. We tend to maybe get a bit stuck in a situation or we outsource the answer to somebody else… but it’s not their career.” (Helen, 01:40)

• On Emotional Clarity:

  “If you can name the emotion, it is much easier to tame the emotion.” (Helen, 03:29)

• On Motivation:

  “Knowing the why behind what you want to do will help you to do that.” (Helen, 05:33)

Timestamps for Key Segments

• 00:00 – 01:01 – Pre-episode book announcement (skip for main content)
• 01:03 – 01:38 – Introduction: Why difficult career decisions are common and complex
• 01:38 – 02:22 – Step 1: Distance—gaining perspective through future-thinking
• 02:22 – 03:38 – Step 2: Data—separating facts from feelings
• 03:38 – 04:24 – Step 3: Discussion—seeking structured conversations with others
• 04:24 – 05:33 – Step 4: Drivers—uncovering your personal motivations
• 05:33 – End – Summary, further resources, and contact information

Actionable Takeaways

• Use the four-step framework (Distance, Data, Discussion, Drivers) to gain clarity on tough career choices.
• Seek insight, not answers, from others who’ve faced similar crossroads.
• Document your facts and feelings to manage emotional responses and build confidence.
• Stay anchored in your motivation (“why”) to act with resilience, even when the decision is tough.

Further Resources

• For an in-depth exploration, check out episode 297 of Squiggly Careers (as referenced by Helen, 06:03).
• Contact: helenandsarah@squigglycareers.com for questions or feedback.

The episode delivers highly practical advice in a friendly, conversational tone, making the process of tough decision-making relatable and manageable, true to the “Squiggly Careers” ethos.