Cover art for podcast Reimagine Work

Reimagine Work

94 EpisodesProduced by Paul MillerdWebsite

Reimagine Work is one of the top future of work podcasts hosted by Paul Millerd of Boundless. Reimagine Work explores our modern relationship with work and features conversations with philosophers, freelancers, self-employed entrepreneurs, thinkers and generous humans who share their perspective on … read more

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Valuing Options & Possibilities On The Solo Creator Path with Kris Abdelmessih

November 10th, 2021


Kris Abdelmessih has one of the most unique perspectives on life and works I've stumbled across in the past few years.  He uses his experience as a trader to look at decision-making and work investments through the lens …

The Formless Path - Money, Fatherhood & Creativity (Howard Gray)

September 27th, 2021


Howard Gray is the founder of Wavetable, a studio that helps brands and companies come together to develop fan-based experiences to help teams teach and share ideas.

The two things that drive him are to "create space …

The Shadow Side of Solopreneurship - Darren Joe

September 19th, 2021


“You can’t study or learn your way into a new identity” - I love this quote from Darren Joe.  He’s been thinking about carving a different path from 2003 to 2004.  He said that he was driven by a natural drive to be …

Six Months In The Creator Economy - Michael Ashcroft (Part 3)

August 19th, 2021


In parts 1 and 2, I interviewed Michael about his plan to quit his comfortable consulting job and start a new path creating and selling courses …

Accidental Freelancer To Brand Consultant, Founder & Freelance Coach (Austin Church)

August 4th, 2021


Austin Church thought he was going to be a poet.  When that didn't go as planned, he joined the business world.  Six months later he was laid off in the 2008 recession.  Luckily, his firm hired him back as a freelancer …

Burnout & "Living At Work" In 2020 - Natalie Rachel

July 22nd, 2021


Natalie Rachel went through her own experience with burnout before turning to help others.  She found that "with burnout, rest doesn't touch it," you need a deeper strategy.  We compare notes on our own journeys where …

Narratives, Work & What Matters - Ben Hunt

July 6th, 2021


Ben Hunt is a father, husband, former academic, author turned blogger, former hedge fund analyst, investment advisor, and farmer.

And he’s also my podcast guest in this episode.

His writing has been an inspiration to me …

Money Fears, Self-Employment & Living Abroad With Kids - Jenni & Lisa Dazols

June 24th, 2021


Jenni and Lisa Dazols read an essay six years ago which made them question their frantic & busy lifestyle.  They could barely take care of their …

A Sabbatical Every Seven Weeks - Sean McCabe

June 17th, 2021


Sean McCabe runs seanwes and in 2014 he was working seven days per week.   Yup, no breaks.  He knew he needed to make a chance but the problem? All of his friends and even his wife worked at the company.  He decided he …

Youtuber and Doctor - Ali Abdaal on Identity, Prestige, Creativity & Meaning

May 3rd, 2021


I had a conversation with Ali Abdaal about his year away from medicine, how he grapples with his identity, the challenges of veering off the course of traditional metrics of success, enjoying the journey, and the …

What happens six months (and three months) before you quit? - Michael Ashcroft

April 13th, 2021


I talked with Michael Ashcroft six months before he was planning to quit his job.  We talked about his plan to quit his job, what was going through his mind, his fears and what he expected might happen.

We then chatted …

The Self-Employment Meta-Game (Dan Vassallo)

January 26th, 2021


I had a delightful conversation with Daniel Vassallo a self-employed creator for the last three years who seems to have gone through many of the same …

Who are digital nomads? (Professors Rob Litchfield & Rachael Woldoff)

January 19th, 2021


Robert Litchfield & Rachael Woldoff have recently written a book titled "Digital Nomads: In search of Freedom, Community, and Meaningful Work in …

Quitting To Teach History to 500k+ on TikTok (Michael McBride, Creator of Idea Soup)

January 11th, 2021


Michael Mcbride left his job almost a year ago to work on building out Idea Soup, an instagram and TikTok channel focused on helping re-inspire people’s passion for history and knowledge.

We talk about his creations …

Curating Goodreads Remotely (Uri Bram, CEO of The Browser)

December 24th, 2020


Uri Bram is the CEO of The Browser which runs regular newsletters to help people find good articles, podcasts, and videos to read.  He has been …

Packy McCormick - Bringing Fun To Newsletters Since 2019

December 4th, 2020


Packy says that his differentiation "is that I’m going to be having more fun than most people”

I've been a big fan of the energy he's brought to his writing over the past couple of years. But he didn't set out to have a

Podcast Update Nov 2020 - The Pathless Path

November 3rd, 2020


I decided to record a short little update with my friend Travis.  What have I been up to, where have I been living throughout the pandemic and what is in store next for Reimagine Work.

If you'd like to watch on YouTube, …

Angie Wang - My Partner On This Crazy Journey

October 19th, 2020


I interviewed my wife, Angie, who has gone through a major career change and has launched a number of creative experiments and projects over the past couple of years.  She reflected on what its been like going along …

Carving a 21st Century Life & Career - Steph Smith

September 16th, 2020


Steph has a hard time identifying as anything.  Remote worker, writer, or coder don't really do it justice.  The thing that stands out when you talk to Steph is that she is a LEARNER.  Through competing in chess as a …

The Possibilities Of Life Beyond Work with Oshan Jarow

September 8th, 2020


Oshan sums up his worldview as:

"We’re all going to die, but in the meantime, the world is far more mysterious, wonderful, and stimulating than human …

Amy McMillen - Wandering In Uncertainty & Writing A Book (Mid Pandemic)

August 31st, 2020


I had a great conversation with Amy McMillen via a live group conversation and we talked about her journey of leaving her full-time job WITHOUT a …

Will Bachman: Building an Independent Consulting Practice With a 5-Decade Success Mindset

May 28th, 2020


Will Bachman is the creator of a community-first talent platform for management consultants, Umbrex and hosts a podcast for independent consultants …

Reflection with Andrew Taggart on Work & Life

March 26th, 2020


A conversation and reflection with Andrew Taggart on total work, the role of the human amid our current crisis and an exploration of philosophical …

Laurel Farrer: The Global WFH Experiment & Long-Term Promise Of Remote Work

March 18th, 2020


Laurel and I decided to jump on a video call to talk about the world emerging work-from-home experiment amid the evolving Covid-19 pandemic.  We …

Imagining A New American Dream (Diania Merriam, Econome Conference)

January 8th, 2020


In 2015, Diania Merriam discovered the Mr. Money Mustache blog about financial independence and reading it was like a refreshing punch in the face. At the time, she was living in NYC and $30k in debt. She got out of …

A Remote Company With 40 Vacation Days?! (Amir Salihefendić, CEO Doist)

December 10th, 2019


Amir Salihefendić is the Founder and CEO of Doist, a fully distributed, remote company that creates productivity tools (Todoist & Twist). We dive …

The Lazy Person's Guide To Freedom, Generosity & Creative Work (Moataz Ahmed)

December 2nd, 2019


Moataz Ahmed otherwise known as “motizzy” is a graphic designer, consultant and hand lettering artist.  He recently published Part 1 of his book …

Twitter Friends & Threads, Self-Employment & Curiosity (Visakan Veerasamy)

October 30th, 2019


I connected with Visa on twitter, where he’s made many friends over the past several years. I wanted to interview Visa to talk about his leap to self-employment over the past couple of years, but we talked about so much …

Rest, Leisure, Working Less & The 4-Day Workweek (Alex Pang)

October 22nd, 2019


Alex Pang is the author of Rest about how you can do more while working less and is author of the forthcoming Shorter, which shares stories of companies that have shifted to a four day workweek.

Hear about Alex's own …

Geography & Culture Side Hustle Experiments w/ Rohith

October 17th, 2019


I'm experimenting with some shorter episodes where I explore side hustles and creative experiments with people taking action on experiments they are excited about.  

This one features Rohith Amruthur, creator of the …

The Phases & Emotional Journey Of Making A Work Shift (Stephen Warley)

September 19th, 2019


I had a 2nd conversation with Stephen about the phases and emotional experiences of what a shift looks like.  He's coached hundreds of people so has a good understanding of what people typically face.

I created this as …

Good Writing & Doing Work That Matters (Andy Sparks, CEO Holloway)

September 4th, 2019


Andy Sparks founded a company called Holloway, which is trying to solve the problem of sharing knowledge online.  He shared how his startup is trying …

Coworking That Works & The 10k Independents Project - Alex Hillman, Indy Hall

August 21st, 2019


" coworking at its best isn’t an occupancy based business at all. If the only time your members can get value from their membership is when they’re in the room, you’re limiting the potential of your community "

Alex …

Should Everyone Have A Coach? (Ben Brooks, Founder of Pilot)

June 19th, 2019


Years ago, Ben wrote that his personal mission statement was “to help people reach their full potential” and our conversation touches on this theme …

What living on a boat for 18 months can teach you about work & life (John Zeratsky)

June 12th, 2019


John Zeratsky was a designer in the tech industry has worked with hundreds of startups in his time at Google Ventures.  He’s also obsessed with redesigning time and thinking about what matters in life.  Earlier this …

Hannah Wei on her nomadic life, Muay Thai fights, Tinder experiments & community

June 5th, 2019


Hannah Wei has been living as a digital nomad for the last four years traveling across the US, Canada and Southeast Asia.  When she is not working as …

Microadventures, Long-term Travel & Busking Through Europe (Alastair Humphreys

May 22nd, 2019


I talked to Alastair Humphreys after he had returned the previous night from a micro-adventure.  It wasn't a four year biking trip or a challenging long walk across the desert (he's done that though!), but instead a …

Dreaming, starting a tribe & living on an island with three kids (Ben Keene)

May 15th, 2019


After attending a few corporate recruiting sessions, he didn't take for granted that his path was to enter the corporate world.  Twenty years later, he is still carving his own path and has recently returned from Koh …

Heather McGowan on learning, adapting & identity in the future of work

May 8th, 2019


Heather McGowan is the most thoughtful writer and speaker I follow on the future of work. She is able to connect the dots between work, culture, …

Building A Company And Life Filled With Joy (Rich Sheridan, CEO)

May 1st, 2019


Rich fell in love with coding as a child but lost that passion when coding just turned into a job in the late 1990s.  As he looked around and saw everyone overwhelmed in his industry, he decided to take a different …

A Mission-Driven Life & Career (Jerel Bonner)

April 24th, 2019


Jerel calls himself one of the original "job-hoppers."  While he never found a great fit in the corporate world, in the 1980s, he was inspired by Steven Covey to develop a "personal mission statement."  He used this to …

How To Fill Your Morning With Purpose & Joy (Craig Kulyk)

April 17th, 2019


I met Craig at a conference called The World Domination Summit and when he introduced himself he gave me a pack of tea with his business card on it. …

Beyond Average: Co-Creating A Life & Company (Tanya Zhang & Wesley Kang,

April 10th, 2019


Wesley Kang and Tanya Zhang are the co-founders of Nimble Made, an e-commerce clothing brand that makes “actually slim” dress shirts.  

Before taking …

Lessons from 13 years of entrepreneurship & living nomadically (Chris Kirkland)

April 3rd, 2019


Chris Kirkland is a bootstrapped entrepreneur who has been living nomadically since 2006 and is the founder of several web businesses including and

We talk about how he has experimented with …

Creating Art Filled With Magic (Martha Balaile)

March 27th, 2019


Martha Balaile is a fantasy illustrator living in Cape Town, South Africa originally from Tanzania.  Her mission is to figure out how magic, …

From the basketball court to the yoga mat via the corporate world (Gabi Macra)

March 13th, 2019


 Gabi Macra was a top Canadian basketball player that never really thought about the "life after basketball" before dealing with a major injury …

Learning To Quit & Life Reinvention (Christine Bader)

March 6th, 2019


 Christine Bader is currently living in Bali, Indonesia, where she is spending time focused on her family and self.  She is the author of The …

Building & Investing In Calm Companies (Tyler Tringas)

February 13th, 2019


Tyler Tringas is an entrepreneur and traveler.  He's started two companies (one worked!) and now is founding Earnest Capital where he wants to help companies avoid going into $50,000 of credit card debt (like he did) to …

Paul on success, storytelling, learning & experiments (UX Gorilla Interview)

February 8th, 2019


I joined the amazing Jagriti Pande for a fun conversation around a number of different topics.  You can subscribe to her master series on UX designers and other creatives here.

Her amazing editing, way-too-kind-intro …

Launching Uncommonly: One Year Later (Chris Donohoe)

January 30th, 2019


"I didn't think I'd be turning down work and choosing not to grow"

I spoke with Chris Donohoe one year ago about his just-announced launch of his …

Guest Episode: Joe Dumars x Adam Grant x Cody Royle

January 23rd, 2019


This episode is a special treat from friends of Boundless, Cody Royle, who came on the podcast last year to talk about what the business world can learn from sports.

I wanted to share a special episode from his podcast …

Learning, Self-Employment & Making Business More Human (Mike Tannenbaum)

January 16th, 2019


Mike was always a self-driven creator, developing TI-83 apps for his classmates to keep track of their grades from an early age. He spent a lot of time "head in in the clouds, making things." It is no surprise then, …

10 Career Myths We Should Stop Believing (Jeff Hittner)

January 9th, 2019


Jeff Hittner of Your Project X and Paul talk about their favorite 10 career myths. They dive deep into the beliefs and mindsets that drive these …

Mini Episode: Five Things Before You Leap: Lessons From The Self-Employed

December 21st, 2018


In this short episode, I talk about the five lessons I've found that help people make the leap to self-employment:

  1. Find a friend taking a different …

Bryan Victor's Education: wedding planning, year-long travel & building a visual animation studio

December 12th, 2018


Bryan Victor has never taken a traditional path but he doesn’t know any other way. Perhaps that is why he started his own podcast in Singapore, Misfitswhich interviews unconventional Singaporeans.  At 20, he saved up …

Why every company should adopt the 4-day workweek (Tash Walker)

December 5th, 2018


Tash Walker is the founder of a firm and spends her Fridays making marmalade.

Before instituting a four-day workweek at her firm, The Mix, she barely had time for her relationships. She decided to start doing research …

The Humans Behind The Gig Economy (Sarah Kessler, Quartz)

November 28th, 2018


Amid all the buzzwords and reports on the future of work, I find Sarah Kessler's stories about the gig economy to be the most insightful and the most …

Screw The Cubicle (Lydia Lee)

November 14th, 2018


Lydia Lee was a self-described "multi-potentialite" growing up and loves to experiment and play games growing up. You can probably draw a straight …

How A Remote Company Enables Freedom, Trust & Digital Dance Parties (Wade Foster, CEO of

November 7th, 2018


Wade Foster was graduating during the worst recession in the past 100 years and traditional employers were simply not hiring anyone. He reached out to a local software company in Missouri and talked them into hiring him …

"My Name Is Nemo and I Don't Do Small Talk"

October 31st, 2018


Nemo Ashong's bold vision is "a truly inclusive and empowered world" He helps people to be fully expressed and to be more authentic, be more unique …

Ervin Ling On Escaping The Corporate World At 30 To Travel The World

October 24th, 2018


Ervin Ling followed the default path as an actuary, passing test after test. After passing all the tests, he found himself working harder than he was …

Ted Bauer: The Absurdity Of The Corporate World & Real Future Of Work

October 17th, 2018


Ted Bauer is a freelance writer and content strategist who writes prolifically about the future of work. In this episode, he talks about some of his …

Shayne Spencer on the dumb idea project and how failing econ helped him start his firm

October 10th, 2018


While Shayne has built a successful marketing consulting firm, there was no "plan" to do this. His first exposure to marketing was out of necessity - …

Jacqueline Jensen on sabbaticals, rethinking work and building a "calm company"

September 26th, 2018


Jacqueline Jensen has been a digital nomad for 3.5 years, living and working globally. It might surprise you to find out then, that she's written a book called "Travel Isn't The Answer." While counter-intuitive, she …

Dr. Laura Gallaher on using humor at work, leadership at NASA after crisis, and building a business traveling the world

September 19th, 2018


Dr. Laura Gallaher joins me from Serbia, where she is part of Remote Year, a community that travels to twelve locations within a year with a cohort …

Andrew Taggart, Practical Philosopher, on how "total work" is taking over our lives

September 12th, 2018


Andrew is a Practical Philosopher who believes that "there may be no greater vexation in our time than the question of how to make a living in a manner that accords with leading a good life." We dive deep into the …

Podcast Update, Digital Course Experiment & Moving To Asia

August 8th, 2018


Paul provides a summer update:

  1. Shifting the podcast from making sense of the future of work => "The Human Side Of The Future Of Work"
  2. Early lessons …

Tony Triumph on growing up entrepreneurial, moving to NYC with $300 and building incredible relationships

July 18th, 2018


Tony grew up around entrepreneurs but did not use the label at the time. At age 19, he was going to college in Maryland and felt the pull to …

Reflections: One year of freelancing, experiments & other people's reactions

June 13th, 2018


In this short "reflection" episode, I check in on where my head is at one year into my freelance journey and share some of the opportunities I have had, how I have changed my mindset over the last year and how people …

Luke Kanies on his journey from commune to CEO and why people hate working for big companies

June 6th, 2018


Luke grew up on a commune and then ended up as a co-founder and CEO of a startup that raised $87 million. He talks about his unique path and how that shaped his thoughts about building an organization. He raises the …

Candace Cabrera Moore, fearless yoga entrepreneur on building a global business, brand and community

May 30th, 2018


Candace was first inspired by her mother who always looked for solutions to problems rather than admitting defeat so always had an entrepreneurial …

Stephen Warley on the biggest shift since the industrial revolution (Episode 19)

May 23rd, 2018


Stephen has been self-employed for more than 18 years. At first, it was by accident. He referred to himself as a “reluctant freelancer.” We talk …

Nita Baum on how to "be free" and self-employed (Episode 18)

May 9th, 2018


Nita Baum is a rock star self-employed freelancer. She has been working on her own for over a decade and now splits her time across many domains, describing herself as an "entrepreneur, co-creator, facilitator, …

Boundless/Unleashed: Paul on the future of work, freelancing and his media diet (Episode 17)

May 2nd, 2018


This was an interview of Paul on the Unleashed podcast hosted by Will Bachman, who is the founder of Umbrex, a platform for independent consultants.

Damien Peters on blogging, wealth, and building a remote business from Spain (Episode 16)

April 25th, 2018


Damien Peters is a self-described "personal finance nerd" - which explains how he ended up founding, a platform to preach and teach about the importance of financial freedom and generational wealth to …

Connor Gillivan on entrepreneurship, selling on Amazon and working with freelancers (Episode 15)

April 18th, 2018


Connor's path as an entrepreneur began when he was in college via an AIM chat with a classmate in one of his classes. What started as a textbook …

Jen Morilla on breaking plates and traveling the world with purpose (Episode 14)

April 11th, 2018


Jen Morilla is an impact travel influencer. What does that mean? It means she travels the world and writes about her experiences but also has a central mission. At first, she started out with the mission to "change the …

Romy Rost on leadership, freelancing & coaching as a skill (Episode 13)

April 4th, 2018


Romy is an employee engagement consultant turned coach. She built her career consulting for and working in Fortune 100 companies on all challenges …

Tanya Alvarez on entrepreneurship, community & redefining failure (Episode 12)

March 28th, 2018


Tanya Alvarez is the Co-Founder, and CEO of OwnersUP is a platform which advances solopreneurs business through accountability, goal setting, and …

Pauri Pandian on tennis as a career, coaching & healthy masculinity (Episode 11)

March 21st, 2018


Pauri started playing Tennis when he was seven and it has turned into a clear passion. He wasn't always sure that was the path he wanted to take, but when a job as a teacher fell through because he decided to attend his …

Ben Dubow - From State Department Rejection To Propaganda-Fighting Startup Founder (Episode 10)

March 14th, 2018

Ben is the founder and COO of Omelas, a startup that is focused on using technology to fight propaganda. Ben's journey, however, does not start …

Paul Millerd on Finding Work That Matters To You (Episode 9)

March 7th, 2018

This is a copy of the interview I did with Stephen Warley on the Life Skills That Matter Podcast. Stephen is a bit of a role model for me. We have …

Amma Marfo on Combining Humor, Creativity & Writing (Episode 8)

February 28th, 2018

Amma Marfo cracked me up several times on this podcast. It is no surprise then, that she describes herself as "thoughtful yet incurably silly." She …

Tom Critchlow on Personal Branding, Freelance Consulting & The Future of Work (Episode 7)

February 21st, 2018

I discovered Tom by reading a piece he wrote on freelance consulting.  I was fascinated with his approach and how similar it was to mine - especially …

Cody Royle on The Talent & Performance Secrets of The Sports World (Episode 6)

February 14th, 2018

Growing up all Cody thought about was sports. He saw his path as becoming a professional Aussie Rules Football player. However, after competing at …

Janet Matta - Rock Star Career Coach On The Alternative Paths We Fail To See (Episode 5)

February 7th, 2018


Janet is one of my favorite people. We have a similar belief that people are capable of more than they believe and that alternative paths are more …

Super Bowl Minisode - Cody Royle on The Patriots and what business can learn from sports

February 4th, 2018


In this episode Cody Royle and I discuss what sets high performing NFL organizations like the Patriots and the Giants (and others apart from the rest). Cody is the author of Where Other’s Wont: Taking People Innovation …

Chris Donohoe on "uncommon" leadership, starting his own firm and "limitless creation" (Episode 4)

January 31st, 2018


Chris is the founder of uncommonly and an avid fan of the long-running CBS television show Survivor. A former teacher, marketer, and management …

David Vaucher on Ending His Career to Start His Life (Episode 3)

January 25th, 2018


David was born abroad then moved to the US at a young age, all while being raised to believe that the path to success rests solely on going to school …

Noel Boyland on “doing the things you want to do” in your career (Episode 2)

January 18th, 2018


Although Noel claims he lacks wisdom, he has a lot of it. He describes his career as “eclectic.” Starting his career in the 1980’s the environment around him (greed, money) influenced him to question what he was really …

Episode 1 - Why do I care about the future of work?

December 20th, 2017


Paul talks about why he is passionate about the future of work and shares some of his personal journey

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