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Madeline Miller is an ex-entertainment lawyer turned career and leadership coach, helping professionals find purpose and fulfillment in their work.
From working on Hollywood blockbusters like the James Bond franchise to launching her own coaching business, Madeline shares her journey of navigating burnout, imposter syndrome, and the fear of leaving a secure career. Her story is a powerful example of how taking risks and aligning with your values can lead to personal and professional fulfillment.
You’ll learn...
Exactly how Madeline transitioned from entertainment law to coachingWhy chasing money doesn’t always lead to fulfillmentHow to overcome imposter syndrome when starting something newThe importance of aligning your career with your core valuesHow Madeline built her personal brand and scaled her coaching business through contentInstagram - @madelinemillercoaching @heydeanreilly @work.worth.doing.podcast
Newsletter - workworthdoing.transistor.fm
Learn how I built my Airbnb Business below:
https://join.thesaco.co.uk?affiliate_code=e019b7 -
Adam Smith is an ex-hospitality manager turned coach, entrepreneur, and business builder who has transformed his life by helping others.
Adam shares his story of moving from late-night bar shifts to creating a thriving coaching business, emphasizing the importance of resilience, self-awareness, and acquiring the right skills to succeed. From battling self-doubt to building a million-pound business, his journey offers inspiration and practical advice for you if you're looking to reinvent a part of you.
You’ll learn...
How Adam leveraged his hospitality experience to transition into coachingThe key habits and mindset shifts that helped Adam overcome self-doubtHow building the right partnerships accelerated Adam's business growthPractical steps for starting and scaling a coaching business from zeroWhy defining a clear long-term vision can protect you from burnout and distractionsInstagram - @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fmLearn how I built my Airbnb Business below:
https://join.thesaco.co.uk?affiliate_code=e019b7 -
Saknas det avsnitt?
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Dean shares a solo episode about the lessons learned from a £16,000 loss early in his entrepreneurial journey. This candid account provides actionable advice for handling setbacks, staying resilient, and navigating the emotional challenges of business ownership.
You'll learn...
Why I lost £16,000 ($20k usd)What to remember when buying any online courseHow to soften inevitable setbacksMy biggest realisation from this painful lossInstagram - @heydeanreilly @work.worth.doing.podcast
Newsletter - workworthdoing.transistor.fm
Learn how I built my Airbnb Business below:
https://join.thesaco.co.uk?affiliate_code=e019b7 -
Troy Munson is an ex-enterprise sales executive turned entrepreneur who left the corporate world to build his own businesses. From selling two startups to launching Demo, Troy’s journey is about taking risks, learning from setbacks, and creating a life of purpose.
Troy shares his transition from high-paying sales roles to entrepreneurship, the challenges of building on the side, and the rewards of taking control of his career and life.
You'll learn...
-How to transition from sales to entrepreneurship
- The risks and rewards of starting a business while working full-time
- How to turn your side hustle into a full-time venture
- The importance of resilience and long-term thinking
- Why success looks different for everyoneInstagram - @troy.munson @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fmLearn how I built my Airbnb Business below:
- https://join.thesaco.co.uk?affiliate_code=e019b7
Timestamps:
00:44 - Troy’s journey from sales to startups
03:30 - Why sales executives earn more than surgeons
07:06 - The hidden dangers of comfort in enterprise sales
09:43 - Why Troy always knew he wanted to be an entrepreneur
12:45 - Building Vocal: From idea to selling the business
18:36 - Dealing with doubts and setbacks as a founder
23:50 - How to start a business discreetly alongside a job
30:02 - Selling Referral: Solving problems with creativity
37:01 - Why success looks different for everyone
43:36 - What motivates Troy to keep building businesses
48:04 - Final thoughts: Taking the leap to build your dream life -
Chris O'Connell is a recruitment industry leader, entrepreneur, and advisor who built a £20 million business, only to lose it all and start again. His story is one of resilience, transformation, and adversity.
Chris opens up about his journey from childhood trauma to building a successful recruitment business, navigating personal and professional setbacks, and ultimately rebuilding his life and career with a newfound sense of purpose.
You'll learn...
- How to overcome adversity and build resilience
- The challenges of scaling a business to £20 million
- How to rebound from major financial and personal setbacks
- Why authenticity and vulnerability are key
- Actionable steps for starting a businessInstagram - @chrisoconnellcoach @heydeanreilly @work.worth.doing.podcast
Newsletter - workworthdoing.transistor.fmLearn how I built my Airbnb Business below:
- https://join.thesaco.co.uk?affiliate_code=e019b7Timestamps:
00:44 - Chris’s childhood and its impact on his drive
03:42 - From top recruiter to business owner
05:37 - First steps in starting a recruitment business
07:46 - Landing the first big deal and scaling quickly
09:49 - Building a £20 million business and taking risks
12:45 - How trauma fueled his success and challenges
18:36 - Losing the business and starting over
23:50 - The mental toll of rebuilding from scratch
30:02 - Advice for new entrepreneurs: Just start
43:36 - What’s next for Chris: TED Talks and investments -
Aaron Knightley is a multi-talented entrepreneur, events business owner, investor, podcast host, and content creator with over 400,000 TikTok followers.
Aaron shares his unconventional views on time freedom versus financial freedom, the importance of taking responsibility, and how he helps others transition from a 9-to-5 into their first business. His direct approach and controversial ideas will leave you thinking differently about work, money, and life.
You'll learn...
- Why time freedom matters more than financial freedom
- How to quit a 9-to-5 and start your own business
- Why taking responsibility is key to success
- How to handle financial stress and build wealth
- The power of delayed gratification and consistencyInstagram - @aaronknightley @heydeanreilly @work.worth.doing.podcast
Newsletter - workworthdoing.transistor.fmLearn how I built my Airbnb Business below:
https://join.thesaco.co.uk?affiliate_code=e019b7
Timestamps:
00:00 - Introduction: Why freedom is better than financial success
03:15 - Aaron’s turning point: Having a child at 20
09:12 - Why most people only act when it’s too late
12:45 - The dangers of dependency on a 9-to-5 income
18:36 - Why money makes you happy and secure
25:28 - Taking ownership of your financial future
31:22 - The importance of discipline and delayed gratification
37:01 - Why most people stay stuck in a job they hate
43:36 - Building a business with minimal resources
52:42 - How Aaron’s program helps people quit their jobs -
Blandine Pais is a property entrepreneur who transitioned from 19 years as a personal assistant to building a thriving property business, generating £15-20k per month.
We cover how she did it, starting from scratch, and building a new life in property despite the odds being stacked against her. From juggling single parenthood to managing setbacks, Blandine shares how she found freedom and flexibility through property investing.
You'll learn...
How to start a business as a side hustle while keeping your jobWhy resilience is essential for success in entrepreneurshipHow to scale a property business and generate consistent cash flowHow to find the right mentors and avoid bad adviceWhy it's never too late to start over and pursue your dreamsInstagram - @blandine.pais @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fmLearn how I built my Airbnb Business below:
https://join.thesaco.co.uk?affiliate_code=e019b7Timestamps:
00:44 - Blandine’s transition from PA to property
03:30 - How she started her property journey in 1997
09:12 - Learning new strategies during COVID lockdowns
12:45 - Managing property with the rent-to-rent model
18:36 - Juggling a full-time job and building a business
25:28 - How she scaled her property business
31:22 - Why education and mentorship were key to her success
37:01 - Overcoming challenges as a single mom
43:36 - The importance of curiosity and persistence
52:42 - Advice for starting a side hustle you love -
Dean shares a solo episode about navigating change, breaking free from unfulfilling work, and transitioning to becoming a business owner.
This episode is packed with insights on how to handle uncertainty, stay motivated, and embrace the messy journey of transformation.
Dean outlines three core steps for tackling change and building a life of flexibility and autonomy.
You'll learn...
- How to clarify your vision and purpose
- Why embracing discomfort is essential for growth
- How to take consistent action while letting go of outcomes
- The importance of focusing on the process, not just the results
- Why privilege gives you the power to create the life you wantInstagram - @heydeanreilly @work.worth.doing.podcast
Newsletter - workworthdoing.transistor.fmLearn how I built my Airbnb Business below:
- https://join.thesaco.co.uk?affiliate_code=e019b7 -
Scott MacPherson is a property entrepreneur who shares his journey of resilience, learning from failures, and finding success while navigating personal and professional challenges.
Scott’s story highlights starting his business from scratch, dealing with burnout and anxiety, to building resilience in the face of setbacks, all while balancing life with his partner.
You'll learn...
How to build a property business from the ground upHow to be authentic in content creationHow to document your journey and have fun doing soHow Scott has managed massive setbacksInstagram - @scottmacphersxn @heydeanreilly @work.worth.doing.podcast
Newsletter - workworthdoing.transistor.fm
Learn how I built my Airbnb Business below:
https://join.thesaco.co.uk?affiliate_code=e019b7Timestamps
00:44 - Starting a business with minimal resources
03:30 - Why Scott moved 400+ miles to start fresh
09:12 - Dealing with anxiety and panic attacks
12:45 - The importance of having a supportive partner
18:36 - Navigating the challenges of building a business
25:28 - The power of documenting your journey
31:22 - Authenticity in property content
37:01 - Managing financial risks and debt
43:36 - The lessons learned from setbacks
52:42 - Finding joy in the small wins along the way
1:01:30 - Building resilience through tough times
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Tommy Lewis is an ultra-runner and content creator, who shares his journey of self-discovery and creating impactful content around his passion.
Tommy’s story covers everything from quitting the unfulfilling, to embracing long-distance running, overcoming self-doubt, and building an authentic online presence.You'll learn...
How to start a fulfilling career by pursuing your passionsThe mental and physical demands of ultra-runningHow to create content that resonates on a personal levelTips for building an online presence that stays true to who you areWhy Tommy lives on the edge of his comfort zoneInstagram - @tommyrunpt @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fmLearn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7Timestamps:
00:44 - Quitting an unfulfilling job for passion
03:30 - First steps into content creation
09:12 - How ultra-running transformed Tommy’s mindset
12:45 - The journey to self-discovery through running
18:36 - Dealing with burnout and finding balance
25:28 - Building an authentic personal brand
31:22 - Lessons learned from ultra-marathons
37:01 - The importance of setting big goals
43:36 - Handling online criticism and negativity
52:42 - Finding meaning in every moment of life
1:01:30 - Why fitness is a gateway to self-improvement
1:13:45 - Reflections on identity and growth
1:25:22 - Connecting with an audience authentically
1:37:50 - The role of self-discipline in achieving goals
1:49:30 - How to sustain motivation for the long term
1:58:00 - Final thoughts on embracing discomfort -
Dan Budden, co-founder of 53 Degrees Property is someone you should listen to.
Dan shares his journey from university sailing to building a thriving property business, discussing everything from managing multiple Airbnb units to dealing with difficult guests and scaling a business that allows him to travel the world.
***This episode was before Quittable rebranded to Work Worth Doing***You'll hear us talk about...
How Dan scaled his side hustle to £70k monthly profitHow to build a scalable Airbnb businessHow to build a business that suits your desired lifeHow to make your business not rely on youLearn how I built my Airbnb Business below
https://join.thesaco.co.uk?affiliate_code=e019b7Instagram - @the_property_athlete @heydeanreilly @quittable.pod
Website - workworthdoing.transistor.fm
Timestamps:
00:44 - 53 Degrees Property business overview
03:30 - Profit breakdown and scaling challenges
05:52 - Dealing with negative feedback and scrutiny
07:06 - Sailing to property: Dan’s background
10:32 - Managing rapid growth and scaling to 100+ units
14:48 - Challenges of the service accommodation industry
18:15 - Dealing with difficult guests and operational hurdles
23:04 - The ethics of selling high-priced property courses
29:46 - Balancing work, travel, and building a remote business
43:36 - The importance of setting long-term goals
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Our guest today is Sam Shortall, founder of Limitless Academy, an online coaching business helping people transform their lives through fitness.
Furthermore, he also can help you to become a coach too!
Sam and I discuss his journey from losing his sales job to building a successful online coaching business during COVID. His story is one of resilience, transformation, and taking risks.
***This episode was before Quittable rebranded to Work Worth Doing***
You'll learn...
How a shock surprise pushed Sam to build a businessHow to get started in online coaching with no qualificationsThe importance of accountability and building client relationshipsWhy losing a job or facing adversity can lead to successLearn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7Instagram - @samshortall_limitless @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fm
Timestamps:
00:44 - What Sam had to quit to become a coach
03:15 - Losing a job just before COVID
05:52 - How Sam started his coaching business
09:12 - Starting a business with no safety net
12:59 - Moving to Liverpool to cut costs and go all-in
17:28 - Struggles with self-belief and overcoming adversity
23:00 - Building a team and scaling his coaching business
31:33 - Why you need to delegate tasks in business
43:36 - Dealing with body dysmorphia and fitness insecurities
52:42 - How to get started in coaching with minimal experience
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Our guest today is Lewis Kemp, founder of Lightbulb Media, known for his no-BS approach to personal branding and digital marketing.
Lewis shares his journey from starting his agency to retiring his mom, and how his focus on authenticity, patience, and long-term thinking led him to success.
***This episode was before Quittable rebranded to Work Worth Doing***
You'll learn...
How to build a personal brand without being a dickheadWhy emotions play a crucial role in your marketingHow to retire your mum by building wealth through business and investmentsWhy patience and delayed gratification are key to long-term successLearn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7Instagram - @lightbulbdmediauk @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fm
Timestamps:
00:44 - What most people get wrong about personal branding
03:30 - Building a brand by focusing on emotions
05:42 - Handling negative comments and online trolls
07:06 - How Lewis retired his mom
09:58 - Investing strategies that helped him retire his mom
13:11 - Running a digital marketing agency with 25 clients
17:28 - Why integrity is essential in business
23:04 - How to avoid burnout while running an agency
29:46 - The real cost of scaling a business
37:01 - Advice for building wealth and playing the long game
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Our guest today is Neil Sands, an Irish entrepreneur and former Salesforce executive, who has launched several innovative businesses.
Neil shares his experience launching brands like Lost Irish Whiskey and MASK during COVID-19, and his insights on spotting opportunities, building businesses from passion, and taking calculated risks.
***This episode was before Quittable rebranded to Work Worth Doing***
You'll learn...
How to spot opportunities nobody else seesHow to create a product that resonates deeply with consumersWhy passion, not just profit, should drive your business decisionsHow to deal with financial stress and losses as an entrepreneurLearn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7Instagram - @cxoneilosands @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fmTimestamps:
00:44 - Launching Lost Irish Whiskey during COVID
03:30 - Creating whiskey for adventurers
09:43 - The power of human-centric design
15:29 - Starting MASK for domestic PPE production
23:00 - Challenges in PPE supply during the pandemic
29:30 - Building resilience in entrepreneurship
37:27 - Dealing with financial stress and big losses
45:00 - How Halo.ai helps protect racehorses
53:00 - Finding the right moment to take the leap
58:00 - Advice for people unhappy in their current careers -
Our guest today is Henri Ghijben, a business owner, property investor, mentor, and podcaster.
Henri shares his journey from losing everything to rebuilding his life and businesses. His story is one of resilience, learning from failure, and the importance of self-development.
***This episode was before Quittable rebranded to Work Worth Doing***
You'll learn...
The value of failure and how it can be a powerful teacherWhy self-care and time management are crucial for successHow Henri overcame 500k debt and rebuilt his lifeThe impact of a near-death experience on Henri's perspectiveHow to transition from winging it to mastering your craftLearn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7Instagram - @hrg_tree_surgeons @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fmTimestamps:
00:44 - Balancing multiple businesses
03:13 - The importance of morning routines
05:51 - From Fail Forward podcast to Tree Surgery podcast
09:59 - Challenges in the tree surgery industry
17:19 - Life before mentoring and service accommodation
23:15 - Winging it to seven figures, but at a cost
29:04 - Losing everything and starting over
34:49 - Getting into property and service accommodation
41:01 - Health scare: A stroke and its impact
50:01 - Fear of the unknown and stepping out of comfort zones -
Our guest today is Joe Caulfield, a former sales professional who took a bold leap into the world of broadcasting.
Joe's journey highlights the ups and downs of leaving a stable career for something completely new, and the resilience needed to pursue what truly fulfills you.
***This episode was before Quittable rebranded to Work Worth Doing***
You'll learn...
How to recognize when it’s time to make a career changeHow to take risks and trust your gut even without a backup planHow to build confidence in front of the camera and the microphoneHow to manage and embrace the uncertainty in a creative careerLearn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7Instagram - @joe_caulfield_ @heydeanreilly, @work.worth.doing.podcast
Website - workworthdoing.transistor.fmTimestamps:
00:44 - Leaving a sales job without a backup plan
03:30 - Turning down a high-paying job offer
09:43 - Finding a passion for broadcasting
17:29 - Getting into broadcasting during COVID
23:21 - Balancing a day job with a broadcasting dream
29:30 - Landing the first big gig
37:27 - Learning to love public speaking
42:21 - Choosing passion over a high salary
47:18 - Finding fulfillment through hard work
53:00 - Advice for those considering a career change -
Our guest today is London-based entrepreneur, Fabio Cao.
Fabio has traveled to 198 countries and is the first person to pull this off with an Italian passport! Alongside his incredible travel journey, he has built a successful chain of hostels across Europe and South America.
***This episode was before Quittable rebranded to Work Worth Doing***
You'll learn...
How to build a business that supports a lifestyle of freedom and travelHow to take calculated risks even with no prior experienceHow to survive and adapt your business during unforeseen scenarios such as a pandemicHow to use YOUR passion to drive your entrepreneurial journeyLearn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7Instagram - @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fmTimestamps:
00:44 - Starting with a passion for freedom
03:30 - Launching a hostel with no experience
09:43 - Taking an 80k risk
17:29 - Building a business to support travel
23:21 - Dealing with COVID-19's impact on tourism
29:30 - Why not taking risks is the biggest risk
37:27 - Balancing work and a life of adventure
50:00 - Motivating yourself with long-term vision
55:00 - The value of persistence over talent
59:00 - Final thoughts and motivation -
Our guest today is Dublin-based entrepreneur, Paul Jackman.
Paul has launched and scaled the fragrance line, Handsome Scent, starting in Covid and in just 4 short years scaling it to a 7 figure brand!
***This episode was before Quittable rebranded to Work Worth Doing***
You'll learn...
- How you can launch an e-comm brand as one idea then change it’s trajectory
- How you can leverage YOUR story to generate interest in your business
- How you can get comfortable talking to a camera
- How you can manage scrutiny from people in and outside of your circleLearn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7Instagram - @pauljackman182 @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fm
00:44 - Launching business during the pandemic
03:30 - Reaching 20,000 customers
05:48 - Why he chose not to take on investors
09:43 - Unique selling points of his fragrance
17:29 - Pivoting entire product strategy
23:21 - Why he started
29:30 - How you can start an e-commerce business
37:27 - Founder-led content to drive engagement
50:00 - Criticism and how it fuelled his determination to succeed
55:00 - The future of Handsome Scent -
In this episode of Quittable, host Dean shares his personal experience with fear and the THREE WAYS you can implement tactics to stop fear from preventing you doing the things you want to do in your life!
Fears are always going to be there, so get used to them. The trick is dealing with them correctly such that you continue on your path.
Expect to hear stories from the psychological warfare of posting on social media... the fear that could be stopping you taking the risk you want... insights from Outwitting the Devil... and most importantly... how to SOFTEN these inevitable fears and still march forward.
***This episode was before Quittable rebranded to Work Worth Doing***
Learn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7
Instagram - @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fm -
Our guest today is Nathan Stapley. Nathan has dedicated his entire life to helping children with disabilities on a remote island in madgascar get access to education. Something they have never had before!
***This episode was before Quittable rebranded to Work Worth Doing***
Nathan's sacrifice and story is incredibly humbling, selfless, and will inspire you with whatever summit you're trying to currently climb!SUPPORT/DONATE TO NATHANS WORK
- Business Instagram: @labcharity
- Nathan's Instagram: @labnathan
- Website: labcharity.orgLearn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7Instagram - @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fm
Timestamps
00:00 - Introduction and Madagascar Background
02:15 - First Trip to Madagascar
04:14 - Corruption in Non-Profits and Inspiration for LAB07:42 - Founding the LAB Charity
11:47 - Persistence and Early Challenges in Set-Up
17:24 - Fundraising Struggles and Pandemic Setbacks22:55 - Rebuilding the Centre After Setbacks
30:32 - Daily Life for the Children at the Center
38:37 - Finding Purpose Without Financial Stability
44:12 - Expansion into Guatemala - Visa fler
