Squiggly Careers Podcast: End of Year Review – What Our Highs & Lows Taught Us in 2025

Hosts: Sarah Ellis & Helen Tupper
Release Date: December 16, 2025

Episode Overview

In this reflective and informal episode, Helen and Sarah share a candid, behind-the-scenes review of their year—both professionally and personally. Using their signature “high, low, learning” framework, they swap stories about standout moments, unexpected struggles, and the lessons that emerged along the way. Throughout, their conversation is packed with practical reflection prompts, light-hearted anecdotes, and actionable insights for your own year-end review, whether solo or with a “learning buddy.”

Key Discussion Points & Insights

1. The Power of Year-End Reflection ([01:06]–[02:57])

• Why Reflect?
  Both hosts encourage making space to reflect on highs and lows, and share prompts you can use individually or with a team.

  “I think you learn as much from your lows as you do from your highs.” — Sarah [03:23]

• Structure:
  Each reflection uses a “high/low/learning” lens—what worked, what didn’t, and what was learned.

2. Best & Worst Days of 2025 ([04:02]–[14:04])

Highs: Dorset Village Hall Planning Retreat ([04:15]–[09:05])

• Description:
  Both Sarah and Helen recall their favorite workday: a mid-year escape to a village hall in Dorset to strategize their new book, “Learn Like a Lobster.”

  • The retreat was “exactly what we needed”—a blend of space, light, collaboration, and creative freedom.
  • Sarah used AI (Claude) to find the venue:

    “Top tip. AI found that space for me… Claude found that village hall and it was like, what about using this village hall? It cost like £25.” — Sarah [05:11]

  • Their dynamic works best: Sarah generates a flurry of ideas on sticky notes, Helen synthesizes and connects ideas.

• Memorable Moment:
  Sarah’s partner comments on the chaos left in their bedroom after prep, texting Helen:

  “It’s either the work of a genius or a psychopath.” — Sarah [09:05]

Lows: Ill-Timed Illnesses & Tech Fiascos ([09:12]–[14:04])

• Helen’s Low:
  Missing out on a major Lisbon work event due to illness, stuck in her room in a nice dress.
• Sarah’s Low:
  The infamous “Windy Wi-Fi Day”—storms knocked out her home internet, leading to stressful last-minute venue changes and working from a male-dominated coworking space where she was offered tea and digestives mid-session:

  “He knocked on the door in the middle of a session that I was delivering for Lego to ask me if I wanted a digestive biscuit.” — Sarah [11:26]

• Lesson:
  Sharing problems early (“fast flags”) helps diffuse stress and brings unexpected solutions.

3. Work Experiments: Hits & Misses ([14:07]–[28:09])

Successful Experiments

• Helen’s Meetups in Edinburgh and New York ([14:52]–[17:02])

  • Used LinkedIn to set up coffee meetings and a rooftop meetup with podcast listeners and connections.
  • “Brave things can lead to things.” — Helen [16:45]
  • One attendee is now a future podcast guest.

• Sarah’s Podcast Format Revamp ([20:57]–[24:53])

  • Switched to the “Borrowed Brilliance” format—basing episodes on fresh insights from diverse sources, revitalizing their enthusiasm.
  • Greater enjoyment and creativity:

    “Experimenting just helps you move forward with so much more pace and you make more progress. And then really quickly you can see like data, does it work? Does it not? And some of the data for us on that experiment was how much are we enjoying it?” — Sarah [23:38]

Experiments That Didn’t Stick

• Helen’s LinkedIn Posting Challenge ([17:08]–[19:33])
  • Tried daily posting—helped with creativity but wasn’t sustainable or authentic for her.
  • “I think it’s okay sometimes to try something… but if it doesn’t work for you, then let it go.”
• Podcast Logistics Struggles ([24:54]–[28:09])
  • While the new format worked, behind-the-scenes logistics became a recurring pain point.
  • Sarah: “I think we've lived in the messiness… rather than calling it out. And that's one of the things I want to get better at next year: fast flags.”

4. Personal Highs & Lows: Life Beyond Work ([28:45]–[37:17])

• Helen’s High:
  Completing home and garden renovations for improved well-being.

  “I'm really excited to be in here... I just feel really happy, honestly. I look outside, I sit in my office, and I'm happy, really happy.” — Helen [30:07]

• Helen’s Low:
  Facing her first Christmas without her beloved 96-year-old nanny present, a poignant moment of change.

• Sarah’s High:
  A family trip to Iceland—whale watching, zip-lining, and reconnecting with adventurous travel.

• Sarah’s Low:
  Ongoing struggle to set boundaries between work and family:

  “I don’t feel like this year I’ve probably got my boundaries quite right.”
  Candid about messiness (“I've bought a lot of headphones this year…”) and the impact of busyness on her home life.

5. Anticipating 2026: Hopes & Hazards ([38:48]–[46:26])

• Anticipated Highs:
  Both are excited for upcoming US trips—new collaborations, book-related ‘bucket list’ opportunities:

  “There are some moments that I'm really looking forward to doing with Sarah in the US that we have never done before. And it's a bit like, it's a bit bucket listy for us.” — Helen [39:44]

  • A mix of excitement and challenge: “Definitely courage zone stuff for me.” — Sarah [40:08]

• Lows to Avoid / Commitments:

  • Helen: Avoid saying “yes” impulsively—pause to consider impact on her support network.

    “I just want to… not put [my commitments] on other people.” — Helen [42:46]

  • Sarah: Stop recurring “familiar frustration” conversations; shift to problem-solving over venting.

    “I don’t want to end next year and be like, oh, I’ve just talked…the things that we are getting out of the system are the same as they were last year.” — Sarah [45:17]

Notable Quotes & Moments with Timestamps

• On learning from lows:

  “You learn as much from your lows as you do from your highs.” — Sarah [03:23]

• About their creative process:

  “There’s just this fit between yours and my brains…that’s where the best stuff comes in our business.” — Helen [07:49]

• Laugh-out-loud: Post-it chaos at home:

  “It’s either the work of a genius or a psychopath.” — Sarah (quoting her partner) [09:05]

• On the “windy Wi-Fi” travail:

  “He knocked on the door in the middle of a session that I was delivering for Lego to ask me if I wanted a digestive biscuit.” — Sarah [11:26]

• Advice after experiment failure:

  “If it doesn’t work for you, let it go … reaffirmed that ‘running your own race’ thing for me.” — Helen [19:33]

• On podcast revitalization:

  “Borrowed Brilliance…has ignited curiosity and given a different way in.” — Sarah [22:47]

• Work-life boundaries & home chaos:

  “I have bought a lot of headphones this year…The busier I am, the messier I get because I actually get very single minded.” — Sarah [35:07]

• Anticipated high:

  “There are some moments that I’m really looking forward to doing with Sarah in the US that we have never done before. And it’s a bit bucket listy for us.” — Helen [39:44]

• What to avoid:

  “I want to avoid saying yes without checking first… because I could be making life harder for the people who support me.” — Helen [41:11]

Timestamps for Key Segments

• [01:06] What “high/low/learning” reflection means
• [04:02] Best and worst days: Dorset retreat & “Windy Wi-Fi”
• [14:07] Experiments: Meetups, LinkedIn posting, and podcast overhaul
• [28:45] Life outside work: Renovations, travel, and boundaries
• [38:48] Looking ahead: 2026 highs to anticipate and lows to avoid

Reflection Prompts for Listeners

The questions discussed—and several additional ones—are available in the episode’s downloadable “pod sheet” at AmazingIf.com. Helen and Sarah encourage listeners to use these prompts solo or with someone else to guide their own year-end reflections.

Next Episode Preview:
Upcoming episodes feature Squiggly Career Trends for 2026—ten trends, impact, and practical steps for development.

Tone:
Conversational, candid, pragmatic, frequently humorous, and genuinely supportive—true to the Squiggly Careers brand.

For more summarized tools, episode sheets, and inspiration, visit: amazingif.com/podcast