Squiggly Careers Podcast – Episode Summary

Episode Title:

How to Ask for Help at Work (Without Feeling Awkward)
Host: Helen Tupper (Amazing If)
Date: January 29, 2026
Duration: ~17 minutes (Squiggly Shortcut episode)

Episode Overview

In this Squiggly Shortcut episode, Helen Tupper tackles the common but tricky challenge of asking for help at work. She shares a simple, actionable four-step framework designed to make seeking support at work easier and less awkward, offering personal examples, practical advice, and encouragement to help listeners move past the emotional barriers that can make asking for help feel daunting.

Key Discussion Points & Insights

1. Why Asking for Help is Hard—but Essential

• Stigma & Emotional Barriers:
  • Many people fear looking incompetent or vulnerable when they seek help.
  • Concerns include being a burden to others or admitting to struggling ("I have this sort of dogged persistence where I think, well, I’ll just work a bit harder and then I’ll be able to do it." – Helen, 03:01).
• The Cost of Not Asking:
  • Not asking for help can lead to longer struggles and less effective work.
  • "It's faster and easier and often more enjoyable when we ask for the help that we need at work." (03:55)

2. A Four-Step Framework to Asking for Help Effectively

Helen introduces her framework, developed from personal reflection and scribbled on a Post-it note, to neutralize the emotional weight of asking for help:

Step 1: Identify What You Need Help With

• Action: Make a list—neutral, unemotional—of concrete things you need help with in your work and development over the next 6–12 months.
• Examples (Personal):
  • Growing in new markets (US and Middle East)
  • Building products to support services
  • Integrating new technology
  • PhD challenges

"Spend five minutes writing down all the things that you need a bit of help with at work … be quite neutral. I’m not panicking right now." (05:07)

Step 2: Specify the Type of Help You Need

• Three Types of Help:
  • Support: Emotional or peer camaraderie.
  • Solutions: Expertise from someone who has ‘been there and done it.’
  • Sounding Board: Someone to bounce ideas off or help build on your thinking.

"Rather than saying can I have some help, which feels quite big … we are going to think, well, with that thing I need help with, specifically what kind of help do I need?" (08:21)

Step 3: Identify the Right Person to Ask

• Action: Write down who is best placed to provide the help you need for each area.
• Tip: If you don’t know someone yourself, ask your network for a connection.

"For the PhD, I’ve got a giant question mark because I don’t know who can help me—and that’s OK." (10:28)

Step 4: Frame the Ask Clearly and Confidently

• Avoid: Vague or general requests like “Can you help me?”
• Do: Frame as a specific ask for advice or insight.
  • “Do you have any advice on how I can build my reputation and brand in Dubai?”
  • “What would you do if you were running my business?”
  • For peer support: “What are you finding hard and how could we help each other?”

"Framing your ask for help without always mentioning the word 'help' means that you will feel more confident when you make the ask." (13:29)

Notable Quotes & Memorable Moments

• On Neutralizing the Ask:

  "Right now, I think a very useful thing for you to do is to spend five minutes writing down all the things that you need a bit of help with at work."
  (Helen, 05:07)

• On the Power of Specificity:

  "If you write it down, it’s a lot clearer and it's easier for you to communicate."
  (Helen, 14:46)

• Framing Makes the Difference:

  "Avoid the 'Can you help me?' … it's big, it's ambiguous … Instead, I would try to ask for advice. I'd frame it differently."
  (Helen, 12:10)

Timestamps for Important Segments

• 03:01 — Emotional barriers to asking for help
• 05:07 — Step 1: Identifying what you need help with
• 08:21 — Step 2: Types of help: support, solutions, sounding board
• 10:28 — Step 3: Choosing who to ask
• 12:10 — Step 4: Framing your ask confidently
• 13:29 — Practical examples of how to phrase your ask
• 14:46 — The importance of clarity and preparation

Actionable Takeaways

• List out—even privately—what you need help with, removing panic or judgment.
• Be specific about the type of help you need before reaching out.
• Consider your network: if not direct, ask for introductions.
• Frame the ask as an invitation for advice or insight, not an ambiguous cry for help.
• Script your ask in advance for clarity and confidence.

Additional Resources

• Helen mentions supplementary visuals on their YouTube channel and on Amazing If’s [Instagram and LinkedIn pages].
• Feedback and topic suggestions: helenandsarah@squigglycareers.com

The Squiggly Tone

Helen’s style is friendly, conversational, and encouraging, blending personal anecdotes with structured, practical advice throughout the episode.

This summary distills the episode for quick reference and actionable guidance, keeping Helen’s engaging and supportive tone intact for listeners seeking help with their squiggly careers.