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Happy holidays. I’m wrapping up the year with a final podcast and then, on Wednesday, I’ll send out the second annual Rebooting Awards. In the meantime, my final podcast of the year is with Rishad Tobaccowala, a longtime advertising executive who is now also publishing his own newsletter, The Future Does Not Fit In The Containers Of The Past. If you enjoy The Rebooting Show, please leave a rating and review on Apple Podcasts – or share it with others. But first, a message from this week’s sponsor, Mediaocean.

Next week many are heading to Vegas for CES, the annual confab of the tech, media and advertising worlds. I know some of you will be skipping the action this year, but that doesn’t mean you have to miss out. Mediaocean has set up a livestream of its programming of the Mediaocean Retreat so you can still enjoy the thought leadership the Retreat will feature from an array of top executives, including Twitter chief customer officer Sarah Personette, Cadillac CMO Melissa Grady and S4 Capital CEO Martin Sorrell, not to mention my podcast guest this week, Rishad Tobaccowala. The programming will run Jan. 5 and Jan. 6 from 12pmPST to 4pmPST. Check out the agenda and register now. Be sure to tick the box for virtual and you’ll receive access links. Also, the recordings will be available on demand following the event.

Rishad Tobaccowala has long been known in the advertising industry for his sage view of the need to embrace change – “Change sucks. Irrelevance worse.” – often delivered through pithy phrases and neatly numbered lists of points. For the final episode of 2021, I wanted to speak to Rishad to take stock of where we are and where we’re going as we come up on two years into the pandemic era.

For Rishad, the pandemic is a marker of a profound shift, part of what he calls the Great Reinvention. The pandemic is not a singular crisis like previous shocks such as the Financial Crisis, but is instead a polycrisis affecting health, the economy and society. That is leading many to reassess their approaches to life – just see the rise of the so-called anti-work movement. As he put it at the start of the crisis: 

“We had not just a financial crisis, not just a social crisis, not just a health crisis but all three, occurring not just to some people but to all people, not just for a short period of time. If you take the entire world and put them through a financial, social and health crisis for two years and expect things to be the same, you should not be in business and should resign immediately.”

Below are highlights from our conversation.

The unbundling of media

One impact of the rise of Substack and other newsletter platforms is they have given a convenient outlet for people to share their expertise in their fields. Rishad is one of them, starting a Substack back in August 2020 to “remain relevant and keep learning new things.” It became much more, serving as the basis for a new