Design Thinking

How the “Hello Monday” Podcast Gave Me The Confidence and Strategies to Resign from Apple

It’s Monday and my favorite way to start the week is with an episode of Hello Monday with Jessi Hempel from LinkedIn.  This has been my weekly routine since the podcast first began in 2019. It’s a podcast about the changing nature of work and how that work is changing us. Many referenced the year 2021 as, “The Great Resignation.” If you are considering resigning or changing paths, or know someone who is then here is the first of the three posts where I’ll share what helped me make my decision as I resigned from Apple.

How the “Hello Monday” Podcast Gave Me The Confidence and Strategies to Resign from Apple

In May of 2014 Jessi wrote a blog post where she shared:

“Today’s job market looks so different from the one my college prepared me for in the late 90s. That change hardly feels dramatic compared to what’s coming–artificial intelligence, self-driving cars, augmented reality. So what can we all be doing right now to make sure we’re ready for that change, and energized by it?”

In May of 2019, the one thing no one could have predicted was how the pandemic would challenge the traditional world of work, and what we value in the work we do. If there’s one resounding theme from each and every episode of Hello Monday, it’s that we are rarely ever ready to make a leap, pivot paths, and pursue the life we want.

During the early days of the pandemic the guests and questions Jessi was asking became a guide for navigating my own team. What I did not anticipate was how listening to this podcast each week was building my confidence toward changing the work I do and advocating for myself in the midst of a challenging situation. 

Hello Monday podcast
The Hello Monday podcast with Jessi Hempel

Stepping Outside Your Comfort Zone

“Sometimes we have to step out of our comfort zones. We have to break the rules. And we have to discover the sensuality of fear. We need to face it, challenge it, dance with it.” – Kyra Davis

This is advice that we hear often. I’ve come to learn there are two scenarios in which this happens. One in which someone consciously makes this decision, strategically and well thought out. However without insight into the behind the scenes, it may just often look this way. 

The other scenario is you are confronted with a situation where you have to make a choice. You can let your comfort zone hold you back, or you can make a decision that aligns with your values, your strengths, and your vision. I fell into this category. As everyone says, and held true for me as well, you will never feel prepared.

There are three areas that prepared me more than I knew, that I didn’t realize until after I had made the decision – podcasts, people, and my personal brand. Today I’m talking about the first of these – podcasts.

While there are many podcasts I could name, here are three episodes from Hello Monday that resonated deeply with me. 

Elizabeth Gilbert on Career vs Calling

Elizabeth Gilbert is the author of books such as Big Magic, EAT PRAY LOVE, and City of Girls. This episode gives you the permission through a framework to differentiate what you do vs what you love. If they align – great. If they don’t – great. She says there are four layers, a hobby, a job, a career, and a vocation. 

  • Hobby – this is something you do for fun, you may or may not make money. 
  • Job – the thing you have because it pays the bills. It doesn’t have to fulfill your emotional life because you can get this through your hobby. 
  • Career – a job that you deeply care about. If you are in a career that you hate, quit it. Then, get a job or get a career that you are passionate about. She notes, not everyone needs a career.
  • Vocation – a sacred calling

I found myself at the intersection of a career and a vocation.

As I share on my website, my mission, or vocation as Elizabeth would call it, is to design schools that give young people the mindset and skills to thrive in their workplaces and as global citizens. I didn’t feel aligned in the work I was doing at Apple. So, after a series of incidents (which I’ll discuss in another post), I knew this wasn’t a place where I would be able to fulfill my career or vocation. 

This is what I find so helpful about podcasts. Hearing the stories of others, and how they frame dilemmas that many of us experience provides us with the language, and permission to explore our own challenges, feelings, and opportunities. 

The Ten Year Plan with Debbie Millman

Debbie Millman is a writer, designer, educator, brand consultant, and host of one of the world’s first podcasts, Design Matters. In this episode she shares, “The Ten Year Plan.” Debbie talks about how she was struggling with confidence. Also, that she had a stack of books about the topic in her office. She shares how someone came into her office one day and said, “confidence is really overrated and that confidence only really comes about after courage. That it is important to have the courage to take a step into the unknown.”

When I had to make a decision about which direction to take, this is a line that I remembered. I would never have the confidence to do the things I wanted to do. We all struggle with the inner voice inside our head. In my case said, “Wait till next year, or “When X happens then I’ll do X”. Of course, let’s not forget all the people who tell us we are crazy for leaving comfort.

Yet when those timelines we set for ourselves arrive, we find new excuses.

Courage and confidence are two “Cs” that we don’t talk enough about cultivating within ourselves. It’s one of the reasons I love introducing design thinking to students early on. The design thinking process nurtures your creative confidence. It does this with structures and scaffolds to take your ideas and make them actionable. 

Another highlight from this episode was the importance of creating a ten year plan. Not just general goals, but to write the details. What does each day look like? How are you feeling? What are the details related to what you are doing? Manifesting through articulating and declaring what you think you are able to achieve is a powerful exercise.

Time and time again she shares the emails she receives from students years down the line sharing how what they wrote came to be. I love how Jessi tied the creation of a ten year plan to courage. It takes courage to take our ideas and write them down, and say them out loud. Click here to get the questions to try the exercise yourself. A wonderful act of courage as we close out 2021 and enter 2022. 

Jonathan Fields on Finding Your Purpose

This was the most serendipitous episode of them all. This episode aired on September 19. At this point I had spent the past three weeks grappling with making what in my head felt like a huge life transition in resigning from Apple. Reading, “SPARKED: Discover Your Unique Imprint for Work That Makes You Come Alive,” gave me the clarity in contextualizing why I wasn’t aligned in the work I was doing. If you haven’t taken the Sparketype test, I highly recommend it. I love personality tests that give you the language that give you the clarity to articulate how you are feeling in different scenarios. 

The alignment between my Clifton Strengths and my Sparketype were telling. One of my top five Clifton Strengths is “Futuristic.” Also, my Sparketype was “Scientist”. Both of these represent thriving in the unknown where you figure things out. Here’s the excerpt I read and the moment that gave me the clarity and confidence to make the decision:

The following weekend Jonathan Fields hosted a webinar for anyone who had bought the book upon release. Having ordered the book right after listening to the Hello Monday episode, I received the webinar invitation. It wasn’t a webinar talking about the book. It was a series of exercises led by Jonathan and his team to dive deeper. So, it was like he was sitting there planning my next steps with me. 

“What if you’re locked into a job, role, industry, set of processes, course-of-dealing, or context where everything is fairly figured out, nobody seeks change and most people want everything to stay the same? If there is no next problem to solve or thing to figure, fix, or improve, you can’t get lost in the process of figuring the thing out. You can’t do the thing you’re here to do if it has already been done, and no one wants it done better.” 

Looking Ahead to 2022

I can’t recommend this podcast enough. Last week LinkedIn shared the “29 Big Ideas That Will Shape 2022.” In it they share:

 “The pandemics next act will focus on mental health. In 2022, the world will need to reckon with the trauma the pandemic has left in its wake. Life may be normalizing, but many people are still grappling with grief, depression and anxiety.” 

Each week Jessi Hempel asks thought-provoking questions. She shares stories about people who are navigating the changing world of work. Also, shares real strategies and questions that you can take back for discussion with your teams.

As Erik Brynjolfsson shared in my interview with him on the podcast he shared that during the first industrial revolution it wasn’t until 30-40 years later when work was reinvented that we started to see productivity gains that allowed for an increasing number of society to benefit. The pandemic has brought us to this inflection point in today’s world of work as well.

The conversations we have will dictate how we design new ways of working that leverage the power of the technology that we have.

As Jonathan Fields shared in his episode, “Moving forward how might we step back into a place of personal possibility.”

I’m Sabba.

I believe that the future should be designed. Not left to chance.

Over the past decade, using design thinking practices I've helped schools and businesses create a culture of innovation where everyone is empowered to move from idea to impact, to address complex challenges and discover opportunities. 

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