Planning for Non-Linear Career Trajectories

Future of Work Interviews: Paul Millerd vs Al Dea: two thought leaders on how work is changing.

Welcome, curious minds!

This week we have a short double interview through which we explore the future of work through the eyes of two thought leaders: Paul Millerd, author of the "Pathless Path" philosophy, and Al Dea, a former management consultant turned entrepreneur specialising in talent and leadership development who hosts the popular podcast The Edge of Work

Let's dive into their perspectives on various aspects of the evolving work landscape with a short commentary and food for thought/questions.

Planning for Non-Linear Career Trajectories 

Source: Linkedin CEO Ryan Roslansky


We’ve talked about how non-linear careers before (here ‘Quarter-Life Breakthroughs, AI Companions and Lateral Careers and here ‘Develop 100 different lives for career success) which in my personal opinion should be a subject taught in schools. We need to be ‘antifragile’ (yet another concept by Nassim Taleb - it describes systems that not only benefit from disorder, uncertainty, or volatility but actually thrive on it)

Paul Millerd: "On a pathless path, I think you realize that life is always a learning process whether you are employed or not. From the outside it looks like this path is risky but that's only because the costs are obvious: fear, lack of support, financial uncertainty. But once you're on a path like this you realize that being aware of those things all the time can provide a lot of wisdom about life, or at minimum, teach you that there's not much to be afraid of."

Al Dea: "My career journey is a testament to the importance of adaptability and innovation in the face of change. I successfully transitioned from a traditional corporate role as a management consultant at Salesforce to a thriving independent entrepreneur, specialising in talent and leadership development. This transition, which I made during the early days of the COVID-19 pandemic, was driven by a desire for greater autonomy and the opportunity to focus on my passions."

Going back to the ‘Antifragile’ concept, both Millerd and Dea emphasize the importance of embracing uncertainty and change in one's career. Millerd's "Pathless Path" philosophy suggests that the journey itself is the destination, and Dea's experience highlights the potential for significant career pivots even in challenging times. These are times of growth, when you’re going outside of your comfort zone.

Food for thought: How might embracing more uncertainty in careers lead to unexpected opportunities? How would one go about evaluating this when hiring?

On Education and Lifelong Learning

Big topic, also recently covered in The Death of Degrees and the rise of Company Universities. As seen from the chart above, skills can be very unstable and new ones come up in very short timespans. My key question here, which I’m obviously asking myself pretty often since I’ve become a father is: ‘how can you prepare your kids for the increasingly complex, uncertain and competitive world of work out there?’

Paul Millerd: "With our daughter, we hope to just help her get to know herself better and root for her to follow her own interests and curiosity. I don't really have any 'goals' for her in terms of outcomes like fancy colleges, private schools, or impressive jobs, but there are things we value in our family like kindness, generosity, and curiosity, and I hope we can help her cultivate those things too."

Al Dea: "In a world where technology is rapidly advancing, it's more important than ever to invest in employees' development. By creating a culture that fosters creativity and innovation, we can unlock the full potential of our workforce. I believe that organizations must foster a culture that values creativity, innovation, and critical thinking."

Food for thought: This is a tough one to balance. How might educational institutions balance the development of practical skills with the cultivation of personal qualities like kindness and curiosity? In what ways can organizations create a culture of continuous learning that goes beyond job-specific skills?

On AI and Human Skills

Paul Millerd: "I'm using Claude to help me in writing now, mostly to help generate different ideas of writing sentences or synonyms or tone differences and things like that. It's like a writing coach. I also use ChatGPT for cooking which is excellent at answering my beginning questions."

Al Dea: "Even as AI becomes more sophisticated, there will always be a need for human empathy and understanding in customer service. It's not necessarily about choosing either or, but really trying to figure out what exactly are the strengths and capabilities that are at play and who is uniquely positioned to do them. In my case of use, how I've been using AI, I've tried to actually use it. A lot of people say, let AI take the first pass. I've decided to use it. You know what? I actually want to take the first pass in this case because I feel pretty competent in what I'm doing, but I do want to augment it with something else."

Both Millerd and Dea see AI as a tool to augment human capabilities rather than replace them. They emphasize the importance of understanding how to best leverage AI in various contexts, from creative work to customer service.

Food for thought: How might the integration of AI in your daily work change your role or the skills you need to develop? In what areas do you think human skills will remain irreplaceable, and how can we ensure these skills are valued and developed in an AI-driven world.

How do we tackle Demographic Shifts?

Paul Millerd: While we didn’t talk about this directly with Paul, his philosophy indirectly speaks to adapting to changing workplace dynamics. 

Al Dea: "The demographic shifts we are experiencing are unprecedented. As the workforce ages and becomes increasingly scarce, businesses must adapt their strategies to attract and retain talent. In many developed countries, the population is aging rapidly, leading to a shortage of skilled workers in certain industries, such as healthcare and technology. I suggest that businesses may need to invest in training and development programs to upskill their existing workforce or explore alternative talent acquisition strategies, such as hiring from overseas."

I’m particularly interested in this aspect, given how ‘underrated’ it seems to be in the news and books I read on the topic. Ageism is already a big problem both in job search and in the workplace and it’s incredibly tough to combat. How do you break that discrimination when there are no real tools to do so, and in an increasingly competitive market? 

Food for thought: How might companies need to adapt their cultures and practices to accommodate a multi-generational workforce? What opportunities might arise from tapping into previously underutilized talent pools?

On Solopreneurship and Independent Work

Both Paul and Al are now solopreneurs. This is a rising category of workers, and even more so with AI. 

Paul Millerd: "I miss the team-based work with smart colleagues working at a fast pace. It probably happened on 3-4 projects over 10 years. I also miss being able to be part of the training teams at some of my jobs and being able to fly around the globe in business class doing those. I don't miss 80% of it though."

Al Dea: "I can't tell you how helpful AI tools have been for that, particularly as someone who is a one person shop. I can literally type in, summarize show notes and they will within two to 3 seconds give you a summary of the show notes. I very much view my creativity as my unique engine that enables me to do the work that I do. But I know that I alone am not the most creative person in the world. And so in many ways I'm using it to check myself as well as to potentially augment or to get something in my head to bounce something off of it. So maybe I can think of something even better."

Food for thought: How might the rise of solopreneurship and independent work change the nature of collaboration and innovation in the future? What support systems or technologies might emerge to address the challenges faced by independent workers?

On Key Skills for the Future

The change that will come with AI will require honing on different (and in many cases new) skills. We will need to master how to prompt and use the machines, but then soft skills will become critical. 

Paul Millerd: "People think far more communication is taking place when they present information than they think. Unless you are clearly saying simple and powerful things, an audience of 10 people will think 10 different things about what you think."

Al Dea: "In my experience, the most crucial skills for the future workplace include adaptability, creativity, and effective communication. As AI takes over more routine tasks, our uniquely human abilities to innovate, think critically, and connect empathetically with others become even more valuable. I've found that fostering these skills within organizations can lead to more engaged employees and better business outcomes."

Comment: Both experts emphasize the importance of effective communication, with Millerd focusing on clarity and simplicity, while Dea broadens the scope to include adaptability and creativity. They both recognize the increasing value of distinctly human skills in an AI-driven world.

Food for thought: How might education and training programs need to evolve to develop these key skills for the future workplace? In what ways can organizations measure and reward these soft skills alongside more traditional performance metrics?

Final Thoughts and Learnings

Paul Millerd: "People should aim to take a sabbatical sometime in their career, if only to double-check that they are really living the life they want. Too many older people regret how they spent their prime years of their life. Taking three months off is very doable - humans achieve far more challenging goals like buying dream homes, cars, and funding college educations, all the time. Just find 3 months to take off."

Al Dea: "The pandemic has led many to take control of their work narratives, seeking to define their own stories rather than letting others dictate them. I've observed that understanding one's work story is essential for finding meaning and fulfillment in work. As we move forward, I believe it's crucial for both individuals and organizations to embrace change, prioritize continuous learning, and focus on creating value through our uniquely human capabilities."

Comment: Both Millerd and Dea advocate for intentional reflection and self-directed career development. Millerd suggests a sabbatical as a way to reassess one's life choices, while Dea emphasizes the importance of crafting one's own work narrative.

Food for thought: How might organizations benefit from encouraging employees to take sabbaticals or engage in deep reflection about their work? What strategies can individuals use to continuously reassess and align their work with their personal values and goals?

That’s it for today - hope you found these points of views and reflections useful, but would love to know your thoughts, drop a comment or reply! 

Ciao,

Matteo

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