Rishad called it in 2018. Here's what he sees next.

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In 2018, my third-ever guest sat down with me in a cigar lounge in Chicago. Rishad Tobaccowala was Chief Growth Officer at Publicis at the time, and we spent a lot of that conversation on what we were still calling "machine learning."

As I remember it, his warning was blunt: this technology was going to reshape what a job even is, and if employers and society didn't figure out what to do about it, people would be out in the streets with pitchforks.

Seven years and 270+ guests later, I broke my one rule and had him back. He's still the only repeat guest in the show's history. Here's why: he was right then, and I think he's right again now.

The big idea: we're at peak full-time jobs

"We are at peak full-time jobs. I did not say we are at peak jobs, and I did not say we are at peak work or at peak opportunity." (Rishad Tobaccowala, author of Rethinking Work)

Rishad's argument is that jobs are a phase work is going through. Companies will increasingly ask what work needs to get done, not what jobs need to be filled, the way you build a playlist instead of buying a stack of CDs. Work gets done by a mix of full-time people, fractional people, and AI agents. He's not a doom-monger; he calls himself a "pragmatic enthusiast." His point is that the crisis isn't technological. It's a leadership crisis.

I've lived this. After nine years at an influencer agency, I was laid off when we lost our biggest client. The full-time CRO offers that used to show up every year didn't come. At first, I was scared. Then I went fractional, doing biz dev for smaller companies trying to reach agencies and brand marketers. A year and a half later, I'm more satisfied than I've ever been, and I don't have all my eggs in one client.

Here's my sales brain on it: a single full-time job is a pipeline with one deal in it. No CRO would sign off on that forecast. So why do we run our careers that way?

3 things to do about it

1. Make yourself the head of your HR department

"You are the head of your HR department. Your HR department is not your friend." (Rishad Tobaccowala)

Rishad isn't anti-HR. His point is that their incentives aren't yours. Your job is to maximize your optionality: multiple clients, gigs, workflows and opportunities. Optionality doesn't just protect you if one goes away. It lets you be honest with people, nicely and respectfully, because you don't need any one of them.

This week: write down every source of income or opportunity you have right now. If the list has one item, start building a second. A side project, an advisory role, a podcast, anything that isn't tied to a single employer.

2. Spend your AI dividend on relevance and relationships

Rishad's formula for a career that lasts: resilience comes from relevance and relationships. Relevance means constantly upgrading your "mental operating system." Relationships mean getting out from behind the screen.

His practical advice: spend at least an hour a day learning, and pay $20 to $60 a month for a premium AI tool and actually use it. For me, the time AI gives back goes straight into the field. I'm now at a conference every other week, shaking hands and getting off Zoom whenever I can. It almost feels like AI is giving us the chance to be more human.

This quarter: block one hour a day for learning, and put one in-person event a month on the calendar. Treat both like client meetings.

3. Give away 20% of your time

"Generosity to me is an amazing strategy." (Rishad Tobaccowala)

This one surprised me. Most career advice is all "me, me, me." Rishad says spend about 20% of your time helping others, without keeping score. You feel good, you learn things you'd never have run into, and eventually some of those people come back around to help you.

In sales, we'd call this building the network before you need it. The best pipeline I've ever had came from relationships I invested in years before there was anything to sell.

Next week: say yes to one coffee, one intro, or one piece of advice where there's nothing in it for you.

Bonus: AI is the indie's slingshot

On the agency world, Rishad thinks the holding-company model will grow less important, and that small and independent shops are growing faster because AI "is the slingshot that allows David to fight at the same level as Goliath." I've felt that too. Over the holidays, I made an ad for my own consultancy in Adobe Firefly that I'd always assumed needed a production company.

Best line of the episode

"A story is data with a soul." (Rishad Tobaccowala)

Watch the full conversations

In the new episode we also get into Claude Cowork, the future of the holding companies, and the Athena Project, the community Rishad co-founded for leaders figuring out their next act. It's 50 minutes.

Watch the 2026 episode on Spotify. Want to hear where it started? Listen to our original 2018 conversation. Also on Apple Podcasts and YouTube.

More from Rishad, all free: his weekly thought letter at rishad.substack.com, the key ideas from Rethinking Work at rethinkingwork.io, and the career exercise he mentioned on the show, here.

Want the next one? Every issue takes one conversation from The Ad Podcast and turns it into ideas you can use. Subscribe free at adpodcast.beehiiv.com.

Talk soon,Dylan