Meet Your People

“Honest, curious, raw but also forward-looking.”

Julia Checchia

“I feel that the Career on My Own Terms program came at exactly the right time for me. It helped me step back and think more deliberately about the different directions my career could take, rather than feeling I had to fit into one path only. You in the facilitation role brought insight, warmth and practical wisdom.

I felt I had space where I could be honest, curious, raw but also forward-looking. I found the experience great and inspiring. I do have a way to go to complete all the tasks and truly be aligned with the future path, but you definitely set the path, helped me with systems and have been a great accountability buddy. I will miss our time together.”

“A life and career that works for me, my family and my clients.”

Laetitia

“I highly recommend Penelope Barr’s Career on your terms masterclass. Through this experience, I have gained greater confidence in my ability to create a life and career that works for me, my family and my clients. Penelope has thoughtfully curated the best ideas, practices, skills and systems on how to create a career and life on your own terms. Throughout the masterclasses, Penelope shared real-world examples and coached participants on how to apply these concepts/ practices to their situation. It’s been a wonderful experience – thank you Penelope!”

“Penelope is a genius.”

Megan

“Me (before I started ‘Career on your terms’): Theoretically, I’d love to be in the driver’s seat of my own career but hasn’t the new series of ‘Glow Up’ just landed on Netflix? Also, is it zeitgeisty to say ‘landed on’ or does put me into some kind of time warp Boomer bucket? Also, if I was going to be any good at running my own enterprise wouldn’t I be DOING it already? Also, I’m too old. Me now: Penelope is a genius.”

“Insightful but also practical.”

Taural (Taural Rhoden)

“Taking Career On Your Terms was a fantastic experience. The course was thoughtfully structured, blending both familiar and new concepts in a way that was not only insightful but also practical. Penelope has a real talent for weaving these elements together, making the learning process feel both seamless and engaging.

What stood out most, though, was the level of attention and support she provided—not just during the course, but beyond it. She genuinely invests in her community, and I can already tell that being part of the COYT network will continue to provide value well into the future. For anyone looking to take ownership of their career in a meaningful way, I’d highly recommend Career On Your Terms.”

“Just what I need to get my purpose, strengths, and offer clear.”

Adam

“Penelope’s Career On Your Terms masterclass was just what I need to get my purpose, strengths, and offer clear when I stepped out on my own as a solo consultant. The group sharing was invaluable and I now have clarity on where I am headed, the steps to getting there, and most importantly what I need to do next.”

“An immediate return on investment.”

Gretchen

“The Career on your terms masterclass provided an immediate return on investment for me. Penelope presented information in a timely and considered manner, which allowed me to pull together many disparate pieces of work and start to monetise them.

Penelope’s expertise and experience in portfolio careers, along with her capacity to draw out thoughtful engagement from the cohort, gave us unique insights into our own abilities and the needs of our individual circumstances.”

“What’s the point of living a life, if it isn’t on your own terms?”

Dipti

“I have been fortunate to participate in the Career on your Terms Masterclass with Penelope. This has been an incredible experience. Over the last few years I struggled with finding the answer to the question ‘What am I good at’. But through these masterclasses I could not only get my answers but also was assisted with putting together a plan on how I can leverage my talent on my own terms.

Penelope is gifted with this unique skills of curating strategies in bringing the best in people. The workbooks and her guidance were spot on and well structured. I highly recommend these Masterclass to everyone. What’s the point of living a life, if it isn’t on your own terms”

“Deep expertise and extensive network.”

Sharon Samson

“I had the pleasure of being part of Penelope’s Accountability Community during my recent career transition. The support, shared experiences, and encouragement within this group helped me stay focused and motivated and it was invaluable to have a space where challenges were met with guidance, progress was celebrated, and meaningful connections were formed.

Penelope’s deep expertise and extensive network empower professionals at all levels to navigate their career paths and uncover opportunities that align with their goals. I highly recommend reaching out to Penelope if you’re looking for the guidance and support to take the next step in your career with confidence.”

“Ability to influence others to achieve a common goal.”

Clinton Licht

“I met Penelope on a NFP board, and was immediately impressed by not only her attention to detail, but also her ability to see things in a very different way. She has an ability to influence others to achieve a common goal and is skilled in managing all levels of performance objectives.

Penelope is not afraid to speak her mind, but does so with the utmost respect for her colleagues. She is a true professional.”

“Unique style of management balancing the client needs and business priorities.”

Velmurugan Ganapathy

“I had the pleasure of working with and supporting Penelope when she headed the Client Initiated and Transitions Portfolio at Superpartners. She has unique style of management balancing the client needs and business priorities.

Under her effective leadership, I have evidenced streamlining of the end to end client engagement processes and significant improvements to project delivery. The most notable quality is her ability to motivate her team, thereby building and maintaining a highly successful team.”

“A terrific leader, visionary, speaker, daily experimenter, and human being.”

Jenny Ramirez

“I have been fortunate to work with Penelope since the very beginning of the ANZ Scale Agile Transformation, within New Ways of Delivery – Centre of Expertise. She is a terrific leader, visionary, speaker, daily experimenter, and human being. Her leadership skills have been key in building the team and the approach to uplift agile delivery & technology capability across 500 squads and 4 countries.”

“Avoids following process for process sakes and is always focused on continuous improvement.”

Jeff Hon

“As the Head of Client Initiated & Transitions Portfolio at Superpartners, I found Penelope to be an astute delivery driven leader who was always seeking the best possible outcomes when engaging with external clients and internal stakeholders. Penelope takes a pragmatic approach to project delivery, avoiding following process for process sakes and is always focused on continuous improvement.

During her time at Superpartners, Penelope has been able implement significant process improvements within a challenging and often difficult environment. I would recommend Penelope as an asset for any organization and look forward to working with her again in the future.”

“Wise beyond her years.”

Claire Holt

“I worked with Penelope for a little over 12 months while she was in the UK and thoroughly enjoyed the experience! She has a pragmatic, straightforward approach and a strong work ethic – vital to delivering strategic change in either projects, systems or culture. She’s also lots of fun and wise beyond her years, something I value in her enormously.”

“An entrepreneurial spirit… willing to take on ideas.”

Louise Dewar

“Penelope is a very capable leader who as Executive Manager at nabtv displayed a great passion for her role. She has an entrepreneurial spirit, is approachable and above all willing to take on ideas. I’d happily work with or for Penelope again.”

“The voice of reason.”

Kerryn Harvey

“Penelope has been the voice of reason for me as I write my first book. Her regular check-ins to see how my writing is going, and her calm, knowledgable responses to my questions have been invaluable. I am incredibly grateful Penelope has taken the time to share her expertise, and mentor this first time author throughout the book writing process.”

“Delivers every time, on time and on budget.”

Katrina Fleming

“Penelope has a high level capacity to manage people, projects and strategy within a complex corporate environment. She protects brand, nurtures teams, allows you to do your job, provides clear direction, is always on message, has a hardworking ethic, engages and manages multiple stakeholders and delivers every time, on time and on budget.”

“The perfect sounding board.”

Scott Nathan

“Penelope is the perfect sounding board (I know this first hand), to help you work through the complexity of work, life, career tangles or what she calls the “Messy Middle”. I specifically recommend reaching out to Penelope if you are working through a new project or balancing a portfolio career.”

“The confidence to pitch with joy and with ease.”

Salli Cohen

“I engaged Penelope to help me with preparing a pitch for my first book, Rollercoaster. How to be a bloody good policy officer. Like many things, pitches are hard to craft. However Penelope guided me through a thinking framework, tested it with me, and provided me recommendations for improvements and insights as to how my pitch would ‘land’. Having Penelope in my corner gave me both the confidence that my book was worth pitching and the confidence to pitch with joy and with ease.

Penelope has an extraordinary gift of creativity, word-mastery, the delight of curiosity and a beautiful generosity to share her nous to make things better and brighter for others. She’s fun to work with and I highly recommend her.”

“Able to utilise a broad range of channels & skills to create a compelling business proposition.”

Dimitri Katchalov

“Penelope is a visionary leader who is able to utilise a broad range of channels & skills to create a compelling business proposition & effectively implement it within a complex environment.”

“A gentle wake up and a way to realise what else is out there!”

Katrina Gowans

“I participated in Penelope’s COYT program at a time when I felt stuck in bad habits and old ways of thinking. She gave me the framework and tools to help think about my career on my terms in a way that was authentic for me. I recommend this program for anyone needing a gentle wake up and a way to realise what else is out there!”

“Pivotal to my successful book proposal pitch.”

Janine Stratford PCC

“Is she the person to go to? Absolutely. Penelope was pivotal to my successful book proposal pitch. The invitation to pitch arrived and I had about 72 hours to put something together ready for an in-person meeting. Penelope gave me a very clear idea of the best message to convey for the meeting and walked me through how to strategically present my proposal. It went brilliantly and I secured the publishing contract. Thank you Penelope. It might have been very different without your help.”

“Uses a coaching approach to build a mature and capable team.”

Teresa Simmermacher

“Penelope is a trusted and supportive leader who uses a coaching approach to build a mature and capable team. Her approaches are creative and effective. I look forward to the time when I can work for or with her again.”

“Her acumen, professionalism and high level management were always on point.”

Mimi Kwa

“Penelope was instrumental in my transition between network television journalism at ABC / Channel 9 and corporate presenting. Her acumen, professionalism and high level management were always on point. As a program host for NABTV, I enjoyed working with Penelope at the helm of our department for many years.

I would welcome working together again and would never hesitate to recommend Penelope for any position she might pursue.”

“A 1 in a million thinker and connector.”

Andrew Sloan

“Penelope is a 1 in a million thinker and connector. As my mentor, Penelope fueled the creation and success of my first book. She doesn’t do this in traditional ways; she gets underneath the surface to conjure up a clearer vision, then provides the spotlight needed to turn a set of fragile hunches into stronger beliefs and a more certain direction.

Do I trust Penelope? Yes, of course. But more than that, I know what we have created together transcends a project. She is now truly a part of my community—a community of humans that create, produce, and connect each other to make the professional and personal more excellent, but at the end of the day, more likely to be possible.”

“She makes things simple and digestible.”

Nosh Darbari

“Penelope is a very wise human she makes things simple and digestible. I did her Career On Your Terms (coyt) course. I thoroughly enjoyed it. I wanted to get my time back to do things I really wanted to do. She understand what your situation circumstances and personalises it to suit your needs ensuring you receive value from it. Talking about value personally I think it is priceless. I have already put things in place and I can see my path ahead.

Above all she makes it so much fun, honestly I had so many breakthroughs. Thankyou Penenlope for creating this course eternally grateful for helping me live the life I once dreamt of……”

“A strong legacy of bold, creative solutions.”

Kirsty Mitchell

“I’ve known Penelope Barr professionally for many years and am continuously inspired by her innovation, pragmatism, and leadership. Penelope’s reputation for bold, creative solutions and sharing her experience and ideas with others is a strong legacy. Recently I’ve had the privilege to be part of the Accountability Community that Penelope facilitates with care, and generosity.

Penelope shares invaluable insight relating to job search, building a portfolio career, and designing an ideal lifestyle/work life. Whether you join the Accountability Community or get involved in one of her programs, being inspired and coached by Penelope will be extremely beneficial – I highly recommend!”

“Not afraid to challenge others.”

Gavin Wilson

“Penelope has a wealth of Financial Services knowledge and experience, she takes a structured and outcome orientated approach to her work and her depth of knowledge allows her to add significant value. She’s not afraid to challenge others and projects an air of confidence and authority without being arrogant.”

“Allowed us to get on with the job of delivery.”

Purnima Fernando

“Penelope was a pleasure to work for. Her pragmatic approach and the support she provided made both by job and life a lot more pleasant, in a difficult and unstable environment. She was able to buffer myself and the other project managers that worked for her, from unrealistic requests coming from more senior management which allowed us to get on with the job of delivery.

Working for Penelope allowed me to learn a lot from her, improve myself as a project manager and I look forward to an opportunity to work with her again in the future.”

“Her ability to simplify complex challenges and bring clarity to ambiguity is invaluable.”

Prosper Taruvinga

“I had the pleasure of hosting Penelope Barr on the Online Prosperity Show, and what a game-changer she was! Penelope’s insights on innovation, transformation, and her unique 6:3:3 lifestyle were not only inspiring but packed with practical takeaways.

Her ability to simplify complex challenges and bring clarity to ambiguity is invaluable for any business facing digital transformation or seeking to implement agile strategies. If you need a trusted advisor to navigate change, solve problems, or enhance your leadership team’s capabilities, Penelope is the expert you’re looking for!”

“Her PM skills are second to none.”

Darren Vukasinovic

“I worked with Penelope under an extensive digital content strategy initiative that encompassed one of the most significant brand partnerships Sensis had undertaken. Penelope’s PM skills are second to none, encompassing an extensive skill set with stakeholder engagement and people management skills that are rarely found so well represented in the one individual.

She made planning, executing and measuring the benefits of this partnership a fluid process, ensuring problems were identified and mitigated before they translated to true business impacts. I highly recommend her as somebody who not only gets the job done but ensures all involved are informed, engaged and accountable at every step of the way.”

“A perceptive and strategic thinker with a super engaging and warm approach.”

Nicola Ballenden

“Penelope is a perceptive and strategic thinker with a super engaging and warm approach. She has an impressive ability to very quickly understand complex organisational and human challenges and provide timely and thoughtful advice. She also provides a range of practical tools to help you think through issues and holds you to account in the most tactful way.

I have no hesitation in recommending Penelope for any organisation or leader who needs some thoughtful guidance around business transformation, strategic planning, leadership development or professional coaching. She is particularly helpful in terms of helping think through ‘whats next?’ in terms of career planning.”

“She generously shared her knowledge, process, feedback and framework.”

⭐️ Christiane Anderson

“Last weekend I had the privilege of spending a day with Penelope on creating a podcast. She generously shared her knowledge, process, feedback and framework for creating impactful messages that come from the heart and tap into your passion. I recommend anyone working with Penelope on bringing your ideas to life, be it a book, pod or shifting your career laterally.”

“A knack for seeing things from a different perspective.”

Christopher de Waas

“Penelope was a lovely person with whom to work. She is a great listener, and is a thoughtful and supportive leader who really knows how to bring out the best in her team. She is incredibly experienced, and has a real knack for seeing things from a different perspective.

I learnt a lot from Penelope, and am immensely grateful for having had the opportunity to work in her team.”

“She creates a supportive environment built on trust and accountability.”

Ziyue Wang

“I had the privilege of reporting directly to Penelope, and she is truly an exceptional leader. She provides clear direction and strong strategic guidance, while remaining hands-on and deeply involved when it matters. She consistently encourages innovative thinking and challenges the team to improve processes and deliver better outcomes.

What stands out most is her genuine commitment to developing her people. She creates a supportive environment built on trust and accountability, empowering the team to grow and perform at their best. I’m grateful for the opportunity to have worked under her leadership and would highly recommend her.”

“What had felt abstract suddenly became tangible!”

Kate Stewart

“I had the best day at Ship It Sundays with Penelope! For anyone unfamiliar, Ship It Sundays (run through whyleavetheisland.com) is a focused, structured day designed to help you finally move from idea to execution on something meaningful you’ve been sitting on. I’d been circling the idea of podcasting for years. In one day, with Penelope’s guidance, I clarified my voice, my purpose and my positioning. I mapped out my first episodes, recorded a live segment (!) and set a realistic recording schedule. What had felt abstract suddenly became tangible!

Penelope brings structure, momentum and expert perspective, and created a space that felt generous and supportive. Big thank yous Penelope – I love the Ship it Sunday concept and can’t wait to join you again for another productive session.”

“THE person to go to when you find yourself in a crossroads.”

Monica Espinosa Estopier

“Penelope is THE person to go to when you find yourself in a crossroads in life, her extensive experience as a life coach, professional guidance and up to date knowledge of trends, tendencies and predictions is incredible. I am fortunate to be a member of her Accountability Community, a group that is committed to offer guidance, support, personal and professional development, her unwavering commitment and approach to people, their organisations, plans, challenges and projects is invaluable.

The level of support and guidance Penelope offers has transformed my life and has inspired me to achieve greater things in life. Penelope will no only be a pivotal point in your career goals, but will support you through the journey and encourage you to achieve everything.”

“A rare combination of project delivery, stakeholder management and IT expertise.”

Danielle Stewart

“Penelope was a highly effective Project Delivery Director overseeing all client initiated projects at Superpartners. Penelope’s ability to proactively engage with internal stakeholders was outstanding as was the connection and rapport Penelope was able to build with external clients. It is a rare combination of project delivery, stakeholder management and IT expertise that Penelope brings to the table.

Penelope was responsible for running a team who successfully delivered large scale projects that were first to market in the industry. Penelope is professional, intelligent, articulate and would be an asset to any organisation.”

“A safe space to share challenges and celebrate progress.”

Emma Barker

“Being part of the Accountability Community, led by Penelope Barr, has been a transformative experience during my search for my next ‘thing.’ The sense of connection and support from others going through the same journey has been invaluable.

This community provided a safe space to share challenges and celebrate progress, keeping me motivated and focused. It’s comforting to know you’re not alone, and I’m grateful for the positive impact this community has had on my journey. I’m also grateful for the wonderful new connections I made through this community!”

“She excels as a motivator.”

Sara Wexler

“I am delighted to recommend Penelope, whose exceptional qualities and unwavering support have made a significant impact in our professional community. Penelope is a kind-hearted and warm individual who genuinely cares about helping others reach their full potential. Her welcoming nature and willingness to go out of her way to support and work with others is truly commendable.

Penelope excels at keeping people connected and accountable. She excels as a motivator, consistently encouraging people to strive for excellence and celebrating their achievements. Penelope’s ability to inspire and uplift those around her is a testament to her exceptional character and leadership.”

“Dedicated in the development and delivery of innovative solutions.”

Glenn King

“Penelope is a passionate professional who is dedicated in the development and delivery of innovative solutions that add value to the bottom line. Engaging and focussed. Glenn”

“Always empathetic, always practical.”

Adam Murray

“Penelope has an amazing ability to get, at any particular moment, where someone is at and what they need to move forward. Always empathetic, always practical, working with Penelope as a collaborator or being coached as a solopreneur means having someone on your side in moments that can feel like one is doing it all alone. She helps identify blockages and unknowns, finding ways to move through or test them, and to do so without getting too hung up on any particular outcome.

I highly recommend Penelope for anyone looking to work as a solopreneur, or already on their journey and looking for a wonderful guide.”

“An innovative thinker, a gatherer of people.”

Andrew Williams

“Penelope is the real deal. An innovative thinker, a gatherer of people and someone who is making a significant contribution the world we want to all want to live in. I always enjoy my conversations with Penelope. I like her thinking and her energy. She was a mentor to me when I wrote my last book – Getting Unstuck. Her interest and ideas helped me to write the book in quick time.

I highly recommend anyone who has an entrepreneurial spirit or is a budding author to seek Penelope out.”

“She provides clarity in complex situations.”

Louis Liu

“Penelope is one of the great leaders I have come across over the course of my career. She’s visionary and caring. It’s a great pleasure to be part of her team. She provides clarity in complex situations and always delivers great results for the organization while helping her team grow at the same time! Not that many leaders can do it well and Penelope is among the best!”

“Takes personal responsibility for her communication.”

Ha-Dieu Ford

“Penelope’s core strengths noticable from her contribution with Women in Finance includes her project management skills – especially in meeting time schedules and maintaining high quality of events. She is a good communicator and has the ability to take personal responsibility for her communication, manage expectations to achieve effective outcomes and meet the objectives of Women in Finance.

I am pleased to be able to recommend Penelope and have no doubt when she is ready to re-enter her career, she will be a valuable asset to any potential company she chooses.”

Australia, 2026

Meet Your People

the unconference for unconventional careers

Melbourne, Australia

19/11/2026

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