Squiggly Careers – Squiggly Shortcut: You Don’t Need a Perfect Plan to Change Careers — Here’s What to Do Instead

Hosts: Sarah Ellis (and mention of Helen Tupper)
Date: November 6, 2025

Episode Overview

This Squiggly Shortcut episode tackles the often-daunting topic of career change, emphasizing that waiting for a flawless plan isn't necessary—or even helpful. Using encouragement, lived experience, and actionable advice, Sarah Ellis (co-founder of Amazing If) outlines tangible steps for anyone considering a career pivot, whether it's a dramatic leap into a new field or a subtler shift within a current organization.

Key Discussion Points & Insights

Career Change in the “Squiggly” World

• In a “squiggly career,” most people will experience 4-5 types of careers throughout their working life.
• Career changes are both exciting and daunting, but inevitable and commonplace.
• Not every shift is drastic; sometimes, meaningful change can happen through roles within your current organization.

1. Progress Over Perfection (03:04)

• Main Insight: Taking action is more effective than just thinking or planning. Career change is a process, not a single decision.
• Practical Suggestions:
  • Try small experiments: projects, volunteering, or low-risk opportunities to "try before you apply."
  • These mini-experiences help you test fit, lower risk, and build relationships.
• Memorable Quote:
  • “You can't think your way to career change… you have to take action. And this action can be really small experiments.” – Sarah Ellis [02:00]

2. Curious Career Conversations (04:10)

• Main Insight: Conversations are key to understanding the day-to-day reality and challenges of different roles or teams.
  • The more people you talk to, the more insight you gain, and the more opportunities you uncover (“You never know who knows who or who knows what.”).
• Advice for Introverts:
  • Ask for introductions to reduce awkwardness; most people like helping others talk about their experiences.
  • Clarity in your "ask" makes outreach easier and more targeted.
• Sample Script for Outreach:
  • “I’m exploring moving to sales and marketing at some point in the next few years. Do you know anyone who could give me some insights into that or share a bit about their experience?”
• Memorable Quote:
  • “People really enjoy talking about what they do. So never apologize for asking for a bit of help.” – Sarah Ellis [04:55]

3. Talents Over Titles (06:05)

• Main Insight: Focus on transferable skills—your unique strengths, not your current job title.
  • Consider the HOW of your work (e.g., collaboration, creativity, problem solving) rather than just the WHAT.
  • Craft your narrative around talents that could be valuable in your target area.
• Pitfall to Avoid:
  • Don’t let intimidating job descriptions deter you; they’re “wish lists” and rarely match any one person perfectly.
• Memorable Quote:
  • “What would you take with you to a very different job next week? It’s usually your HOWs.” – Sarah Ellis [06:30]

4. Beware the “Perfect” Opportunity

• Many people are put off by job descriptions that seem to demand everything, but few candidates ever fit every requirement.
• “Think about those transferable talents. Have those career conversations. Do the progress over perfection.” – Sarah Ellis [07:15]

5. Bridging Roles Make Real Change Possible (08:00)

• Main Insight: Big shifts rarely happen overnight. Bridging roles—jobs that are a step closer to your desired field—can be essential.
  • These roles leverage some of your current skills while adding exposure to new ones.
  • For most, earnings and security matter: incremental change is often both more realistic and more sustainable.
• Personal anecdote:
  • Sarah and Helen’s transition to running Amazing If took seven years; it was a “test, learn, iterate” experience with bridging roles along the way.
• Memorable Quote:
  • “Successful career change does tend to happen incrementally, and bit by bit. There's no silver bullet of going from one thing to something very different overnight.” – Sarah Ellis [08:45]

6. Be Kind to Yourself & Manage Expectations

• Long-term outlook: Careers are now long and squiggly; immediate transformation is rare.
• “Just kind of be kind to yourself and, you know, think about your own expectations around how to make these things happen.” – Sarah Ellis [09:35]

Further Resources

• For deeper dives into real stories and research on changing careers, Sarah recommends:
  • Episode 379: Interview with April Ryan on career change (includes practical examples and additional inspiration).

Notable Quotes & Memorable Moments

| Timestamp | Quote | Speaker | |-----------|----------------------------------------------------------------------------------------|-------------| | 02:00 | “You can't think your way to career change… you have to take action. And this action can be really small experiments.” | Sarah Ellis | | 04:55 | “People really enjoy talking about what they do. So never apologize for asking for a bit of help.” | Sarah Ellis | | 06:30 | “What would you take with you to a very different job next week? It’s usually your HOWs.” | Sarah Ellis | | 08:45 | “Successful career change does tend to happen incrementally, and bit by bit. There's no silver bullet of going from one thing to something very different overnight.” | Sarah Ellis | | 09:35 | “Just kind of be kind to yourself and… think about your own expectations.” | Sarah Ellis |

Episode Timestamps

• 01:03 – Episode intro, defining “squiggly career” and contextualizing career changes
• 02:00 – Progress over perfection (try before you apply)
• 04:10 – Curious career conversations: getting beyond your current circles
• 06:05 – Talents over titles: what are your transferable skills?
• 08:00 – Role of bridging jobs and the incremental nature of real career change
• 09:20 – Encouragement to be patient, reflect on expectations, and further listening suggestion

Conclusion / Final Takeaways

Sarah distills career change into actionable, reassuring principles: take small actions, talk widely, reframe your skills, use bridging roles strategically, and remember that incremental progress—not overnight revolution—is the norm. The episode closes with encouragement and a pointer to a deeper interview on the topic for those who want more.

This episode is a quick, energizing boost for anyone on the brink of a career change, full of empathy and real-world wisdom.