Podcast Summary: The Creative Boom Podcast

Episode: From Twitter to Ramps & Resilience – Haraldur Thorleifsson on Building with Kindness

Release Date: October 19, 2025
Host: Katy Cowan (Creative Boom)
Guest: Haraldur “Halli” Thorleifsson

Overview

This episode features an intimate and inspiring conversation between host Katy Cowan and creative entrepreneur Haraldur “Halli” Thorleifsson. Known for building one of Iceland’s top digital agencies (later acquired by Twitter), launching major accessibility initiatives, and publicly navigating loss, disability, and high-profile career challenges, Halle discusses the through line of kindness in his life and work. The pair explore how adversity fuels empathy, the perils and gifts of ambition, the trap of overwork, and the importance of building a career—and a life—centered around service, connection, and self-acceptance.

Key Discussion Points & Insights

1. The Roots and Importance of Kindness

• Origin of Empathy:
  Halli reveals that personal hardships, including the loss of his mother and living with muscular dystrophy, shaped his deeply empathetic worldview.

  “I think with that you get a shared sense of humanity, which I don't think you get when everything goes really, really well for you for a long time.” – Halli (02:34)

• Choice and Practice:
  Kindness isn’t innate or constant—it’s a continual, daily choice, especially in the face of pain and adversity.

  “It's not a binary path. It's a choice you have to make constantly...I think it's a choice you have to make every day.” – Halli (04:09)

• Finding Peace Amid Pain:
  Both host and guest share personal stories of injury and acceptance, emphasizing making peace with life’s realities to avoid bitterness and find meaning.

2. Work and Burnout: From Escapism to Overwork

• Substituting Addictions:
  After overcoming struggles with alcohol and substances, Halli channeled his energy into work—sometimes excessively.

  “When I stopped drinking, I substituted my alcoholism with workahol.” – Halli (06:05)

• The Rush and the Trap:
  The satisfaction and 'rush' of building something, winning clients, and overcoming creative obstacles can itself become addicting, leading to potential burnout.

  “It grew so fast and it was hard to appreciate after a while how good we had it...I had a hard time getting excited about the work. And that's when I realized...I can't keep doing this.” – Halli (15:28)

• Learning the Value of Balance:
  Halli reflects on reconstructing his career for sustainability, family, and personal stability rather than relentless achievement.

3. Achieving Success and What Comes Next

• Hitting Milestones and Redefining Purpose:
  After selling his agency to Twitter and running through a long “bucket list,” Halli grapples with the question of what’s next and the challenge of reigniting purpose.

  “I went through my bucket list and I’m not sure what’s left.” – Halli (11:02)

  “I need a new one. I need some things and...if anyone listening has thoughts and ideas, definitely send them to me.” – Halli (30:51)

• Advice for Creatives on Ambition:
  The conversation warns against “chasing mountains you don’t actually want to climb,” advocating for intentionality in ambition.

4. Giving Back & Social Impact

• Ramp Up Initiative:
  Halli discusses ‘Ramp Up’, the nonprofit he founded to improve accessibility through building 2,000 ramps across Iceland, and now expanding globally.

  “It’s a very quick and easy fix that can completely change the lives of people...something I’m really passionate about because it's such a small thing...that can completely change everything.” – Halli (14:05)

• Sense of Duty:
  He expresses a strong sense of obligation to give back, now that he has resources, rooted in childhood memories of poverty and gratitude to his supportive society.

  “Now that I’ve had some success, I feel like it is my duty to give back to the society that was able to help me get to where I am today.” – Halli (08:39)

5. Navigating Career, Identity, and Change

• Generalist vs. Specialist:
  On whether being a creative generalist is the future, Halli suggests there’s room for both, and values building teams that mix big-picture thinkers with deeply specialized talent.

  “A good team has a good mix of both...But then you need really specialized, really smart people to...do something that's excellent.” – Halli (28:06)

• Ongoing Self-Discovery:
  Reinvention and adaptability—both career-wise and personally—are recurring themes that help Halli stay resilient and creative.

  “Multiple times...that's why I keep switching who I am. It's been really rewarding to try new things and...become a different person.” – Halli (27:29)

6. Social Media Reflections

• On Twitter/X and Social Platforms:
  Halli provides a measured, nuanced view on the evolution (and polarization) of social media, considering the sustainability and pitfalls of such platforms, while noting they aren’t likely to disappear.

  “Twitter was never able to live up to its full potential...It was kind of this beast that nobody really knew what to do with...it’s maybe become [a battleground] even more. But I think that's intentional.” – Halli (22:47, 24:06)

7. The Power of Connection and Friendship

• Investing in Long-Term Relationships:
  Halli treasures his lifelong friends from childhood; these enduring bonds, he notes, are rare, grounding, and precious.

  “I think it's rare and I think it's precious. And I...really work on those relationships because...having that something to ground you is really, really precious.” – Halli (33:18)

• Kindness and Inspiration at Home:
  Citing his activist wife’s compassion as a daily inspiration, Halli emphasizes how surrounding oneself with caring, motivated people shapes one’s worldview and actions.

  “She inspires me every day to push on, to do better.” – Halli (34:56)

8. Wisdom, Acceptance, and Seeking Joy

• Advice to Younger Self:
  Halli movingly wishes he could reassure his childhood self not to be afraid—of rejection, loneliness, or trying.

  “Be less afraid. I was very afraid as a kid...I was afraid of trying, really...I wish I could have...help him understand that it's going to work out pretty well.” – Halli (35:07)

• On Living Well Today:
  A good day might mean listening to audiobooks, playing chess, time with family, pursuing fun projects, or simply seeking out small joys.

  “If you seek out joy, there's a lot of it around.” – Halli (36:47)

Notable Quotes & Memorable Moments (with Timestamps)

• On Shared Humanity:
  “With that you get a shared sense of humanity, which I don't think you get when everything goes really, really well for you.”
  – Halli (02:34)

• On Kindness as a Choice:
  “It's not a binary path. It's a choice you have to make constantly.”
  – Halli (04:09)

• On Success and Burnout:
  “It was hard to appreciate after a while how good we had it...I just realized I can't keep doing this.”
  – Halli (15:28)

• On Purpose:
  “Purpose is the biggest thing we all need as people. If you find a purpose, that can guide you.”
  – Halli (09:52)

• On Giving Back:
  “It is my duty to give back to the society that was able to help me get to where I am today.”
  – Halli (08:39)

• On Overcoming Fear:
  “I was very afraid as a kid...I wish I could...help him understand that it's going to work out pretty well.”
  – Halli (35:07)

• On Seeking Joy:
  “If you seek out joy, there's a lot of it around.”
  – Halli (36:47)

Timestamps for Important Segments

| Timestamp | Topic | |---------------|------------------------------------------------------------------| | 02:34 | The genesis of Halli’s empathy and humanity | | 04:09 | Choosing kindness and peace over anger, daily | | 06:05 | Substituting alcohol with overwork | | 08:39 | Rationale for giving back to society | | 11:02 | Reaching goals, questioning what comes next | | 14:05 | Ramp Up nonprofit—impact and philosophy | | 15:28 | Burnout and losing excitement for agency work | | 20:34 | Restructuring career post-San Francisco, balancing family/life | | 22:47 | Thoughts on Twitter/X and changing digital platforms | | 27:29 | Reinventing identity through various life stages | | 30:51 | Need for a new bucket list—remaining open to new adventures | | 33:18 | The rarity and value of lifelong friendships | | 34:56 | Being inspired by his wife’s kindness and activism | | 35:07 | Halli’s advice to his younger self | | 36:47 | Everyday joys: chess, audiobooks, family, and “seeking out joy” |

Closing Thoughts

The episode is a heartfelt, candid meditation on resilience, meaningful work, and living with purpose. Halli’s story foregrounds the quiet power of kindness, community, and continual self-examination. It’s a gentle but motivating invitation to consider what “success” and “purpose” really mean—and to show up every day with empathy for ourselves and others, even (and especially) during tough times.

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