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

Summary

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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)

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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.

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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)

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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)

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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)

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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

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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.

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Further Resources

• For an in-depth exploration, check out episode 297 of Squiggly Careers (as referenced by Helen, 06:03).
• Contact: [e-mail] for questions or feedback.

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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.

Transcript

[A]

Hi, it's Helen from the Squiggly Careers Podcast. And before you listen to today's episode, I just wanted to let you know about some news that Sarah and I are very excited about, and that is that our new book, Learn Like a Lobster, is ready to pre order now. We really care about everybody learning and growing at work, but we know it is not easy to do, and so we're borrowing some brilliance from lobsters to.

[B]

Help you to do it.

[A]

The book takes three inspiring and surprising abilities of lobsters in terms of how they grow and applies it to how we can learn at work. So if you want some inspiration and you need some practical insights to support your learning, growth and development, this is.

[B]

The book for you.

[A]

And if you pre order now and send your Pre order to helloearnlikealobster.com you can join the Lobster Library where we have a community of lobster learners ready for you to learn with some live sessions. And this will all happen before the book arrives. So pre order the book now, send it to [e-mail] and get started with.

[B]

Your learning straight away.

[A]

Now let's get onto today's episode.

[B]

Hi, it's Helen from the Squiggly Careers Podcast, and you're listening to one of our weekly Squiggly Shortcuts. These episodes are a lot shorter and very focused on ideas for actions. And today we're going to be talking about when you're faced with making a difficult career decision. Because Squiggly careers have lots of change in them, it is inevitable that you are going to have more decisions to make about your development. Sometimes that's because of choices that you're making. Sometimes. Sometimes it's because of situations you are responding to. But the challenge with making decisions is.

[A]

That sometimes we can doubt ourselves.

[B]

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, you know, what would you do? And 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, we need to take more ownership. We need a way to work through this difficult decision. And we think the easiest way to do this is to follow a little bit of a framework. That's what I want to talk to you about now. So the first part of the framework is getting a bit of distance when you are coping with a difficult career decision. And this might look like deciding whether you should apply for a new role. Or it could look like deciding whether you want to change the structure of your working week or deciding whether you want to leave a company. Like lots of difficult decisions, the problem with these decisions is they can sometimes feel a bit overwhelming when you're in that moment. And what we need to do is get a little bit of perspective and distancing can help you to do that. So imagine yourself five years forward from where you are right now. Think about what your perfect day or week might look like, who are you spending time with, what are you working on, where are you working, how, how do you feel in that moment? And then what we want to do is connect the decision that you are faced with today with that future version of you. And we're trying to work out which decision will move you closer towards. So we're just trying to zoom out from where you are right now to this ideal kind of future state and see whether that creates any clarity for you. Now, it might help a bit, but there's still more work that we need to do. So that's where the second part of the framework comes in. This is all about data. So difficult decisions can feel really emotive. Often we're worried about getting it wrong. That can cloud our clarity. We need to get a bit of data. Data is much more objective. So I would recommend that you set a timer for five minutes and what you're going to do in those five minutes is take a piece of paper, divide the paper in two. So you've got a left hand side and a right hand side. On the left hand side you're going to fill it with facts. What are the facts of your current situation? Everything that you know to be true. On the right hand side you're going to write down your feelings, things you're worried about or your concerns, just the emotions that are currently going round your head. What this helps you to see is whether you've got lots of facts, so you've got lots of detail and actually not many emotions, or maybe whether the emotions, emotions are clouding your clarity a little bit. And the psychology on this, which is if you can name the emotion, it is much easier to tame the emotion. So just the act of writing it down can actually help you to manage it a little bit more. So we've got distance, we've got data. Now we can move into some discussions and I would recommend that you talk to at least two people about the decision you're trying to make. Two people that you can talk to relatively quickly so you're not stuck in this situation, the two people that I'd recommend talking to are somebody who's done it and someone who's doing it. So someone who has already done the thing that you are thinking about doing, the decision you're thinking about making, and somebody who's likely to be in the same situation at the moment. Now, we're not asking them, what would you do? What do you think I should do? Because that's just kind of outsourcing the answer to them. We're not doing that. The person that's done it, ask them, what was your thought process? How did you go about making that decision? What, how do you reflect on it now? The person that's doing it, ask them, you know, how are you feeling? What are you considering? What factors are you thinking about? Just get a bit more insight from how other people have approached or are approaching this situation. Then you've got to make the decision. Okay, you've got to decide what you're going to do. But this comes to the last part of the framework, which is all about your drivers. This decision will still be difficult, and even with distancing, even with data, even with discussing, it's still going to be difficult. So I want you to really think about what is driving you. Understanding the why behind what you are trying to do will grow your grit. So even it might still feel like a hard decision to make, and even when you've made it, it might not feel easy with whatever outcome you get to. So you want to feel that you're connected to your grit and knowing the why behind what you want to do will help you to do that. So I hope that's given you a.

[A]

Bit of a framework to follow if.

[B]

You are faced with a difficult decision. Right now, if you want to listen.

[A]

And learn to more, we've got a.

[B]

Full episode on this. It's episode 297 of the Squiggly Careers podcast. We'll put a link in the show notes and if you've got feedback, you can send it to us. Helen and Sarah squigglycareers.com.