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How to prepare a strategic plan for a successful career change

The COVID pandemic has caused many to rethink their relationship with their careers and much ink has been spilled about the Great Resignation. In this episode of Toughest Call, Rishad Tobaccowala, futurist, and author of “Restoring the Soul of Business: Staying Human in the Age of Data,” talks about his strategy for leaving an already successful career decades in the making to achieve something completely different.

Rishad Tobaccowala: Rishad, every career has a midnight hour. The smart people leave at five to 12.

Chaz Thorne: Welcome back, or welcome to, Toughest Call, a podcast for organizational leaders where we hear stories from your leadership colleagues about career-defining decisions. I'm your host, Chaz Thorne. 

In this episode, I'm talking with Rishad Tobaccowala about how he prepared for an exit from an already successful career to something completely different. Rishad, a futurist and keynote speaker who advises global businesses, is the author of “Restoring the Soul of Business: Staying Human in the Age of Data.” His thought letter on Substack: The Future Does Not Fit in The Containers of the Past, is read by thousands each week. 

The COVID pandemic has caused many to rethink their relationship with their careers and much ink has been spilled about the great resignation. Rishad shares the process he went through after deciding to move on from a leadership position at Publicis Groupe that had been 30 years in the making, to an uncertain entrepreneurial future as an author and thought leader.

Rishad Tobaccowala: I had worked for 38 years at the Publicis Groupe, which was a large, global but French-based marketing communications and now we say business transformation advertising firm. And over the last decade, I had been working globally at the org level on strategy and growth for the 70,000-person company, which included helping on mergers and acquisitions, helping decide what things we needed to do in order to ensure that we remain relevant with clients. And I was also to a certain extent, the resident futurist of the group.

Chaz Thorne: How do you define futurist as it applies to your vision of the world and business?

Rishad Tobaccowala: So I apply it as how can I help an individual or a business with their strategy. And I define strategy as future competitive advantage. So my belief is you cannot have a good strategy unless you are thinking about where the future is, both from where people will be, where technology might be, where the globe might be, and where your competitors might come from.

Chaz Thorne: So you had some big changes coming up in your life, the big one, obviously, being reaching a landmark birthday of 60s, there were some changes happening at the company that you had been at for quite some time. What was the big decision that you needed to make?

Rishad Tobaccowala: So the big decision that I needed to make were actually two that were intertwined. So one was: Do I leave something that I've been associated with, and which in many ways, might be the reason I was successful? So as my wife reminded me, she said, “How do you know it's you? And it's not the company?” And so I said, it's obviously both, but she says, “How do you know it isn't primarily the company, and that you happen to be thinking, you're moving really well, but because it's the horse you're riding on. But once you're not on the horse, what's going to happen?” So that was, do I leave something that is extremely successful for me? And when nobody was asking me to leave? 

And then that led to the second question, which is, okay, if I left, what would I do? Right. And what would I do then was the reason was because I started studying about what happens when people leave companies, or quote, unquote, retire. I wasn't planning to retire. But there was a book, which I strongly recommend to people called “Retirement and Its Discontents.” And the three big things I read in that book, and the three big things that came out of the book was that when you left work, you weren't leaving work. But you were basically leaving potentially three things. A, you will leave a community because when you were at work, you had a community both at work of partners and clients, so you are now leaving that. And for most people, they were surprised when they thought that because the community almost disappeared when they stopped working. Obviously, they had some friends, etc. 

The second thing that you were basically sort of leaving was a sense of identity, that a lot of people define themselves by what they did. And so you sort of woke up. And then you said, like, what am I doing? So you had no community, and then you had no identity. 

And the third thing that people begin to worry about, obviously, was purpose, which is, okay, what's time for? Because in many ways, when you are at work, it's like a distraction. It doesn't make you ask like, so. The idea was, okay, so I'm going to lose my community, my identity, and my sense of purpose. Why do I want to do this again?

Chaz Thorne: So what was the process that you went through to finally come to a decision about what you would do?

Rishad Tobaccowala: So there were four things that I did. One was, I spoke to a lot of people both inside my company and outside, which included my mentors, bosses, old bosses, etc., and said, I was thinking of doing this, what did they think, so I was getting their input. And the smartest piece of advice I got, which made me decide I was going to do it, was a line that I got from someone who was at that time, who had just left being like the vice chairman of Kraft, and who had done a lot of big things for Kraft/Mondelez. And he said, every career has a midnight hour, the smart people leave at five to 12. So his stuff is when they like you, and you can leave on your own volition, leave. It's not, you won't get this occasion, you might be leaving a little too early, but leaving one minute late spoils everything. So don't do that. So that basically said, okay, I'm gonna go, because then my other bosses themselves said, I don't understand what this five to 12 stuff is. It's quarter to 12. But I said, No, I think it's five to 12. Okay, so that was one. So that was a big thing. 

The second thing was just getting people's input. Second was obviously listening to my wife who has a special type of input. And her whole stuff is like, hey, I want you to make sure that when you come out of this, that you have a plan as to what you're doing because I don't want you like sitting at home and watching television and things like that because she says, I know that would keep you happy. And if nothing else, you will get in my way. Okay, so do what you'd like. But, there was a different piece of advice, which is like, how will what I do impact the life of my wife and children and my children are grownups. It wasn't that was a but it was more like, if I changed my life, how does it affect her life? Right? So that was sort of a second whoever, your partners, or whoever's around you. 

The third was, what will I do? So I started thinking about what will I do? And I put together something that was very simple initially, and then I built an amazing architecture. And once I built the architecture, it was like, Oh, my God, this actually makes sense. Right? And, it was very simple. So I started off by saying, I'll have a book. So I'll write. And then maybe I'll speak about the book, and then maybe advise about the topics about the book and that will be it. But that didn't sound sexy, right. So what I actually developed was a service, I said, I was going to do cognition as a service. So I was going to help people through my thinking, so cognition as a service. And I was going to market and a one to many, one to some, one to one method. And the one to many would be writing, the one to some would basically be speaking and teaching and one to one would be advisory. 

And the last thing was, and this is extremely important, which is elegant exiting. So then I put together plots of elegantly exiting. So a lot of people talk about how important entrances are. People forget that exits are as important as entrances. So how should I leave in a way where there were some people, including some of my bosses, who were not exactly sure why I was leaving, right? But how could I leave in a way that was elegant, both because I'd worked for a place for 38 years, so why don't make sure that it was elegant. And then I felt good about the place. They are left and they still felt good about me.

Chaz Thorne: As you were coming up to the point where you had clearly done your due diligence you had decided you decided what you were going to do. How were you feeling emotionally as you were going through this, and then just before you made the leap, where you were going to communicate the decision that you had made.

Rishad Tobaccowala: So, you know, initially it began with clarity, which is I need to do this, then I went from clarity to sort of uncertainty, which is how do I do it? Right. So, to me, what was very important that gave me clarity was that a big part of the reason I believe that I was successful was because I had an amazing relationship that I've built over the years with two people, to senior people. And my sense is when they retired, and I was not interested in taking their places, whoever would come and I knew everybody who would come would actually be younger than I. And in order to build the same relationship, it would take me a few years. And at the very same stage, if you were smart enough, and you looked around, they had their equivalent of me. Right? So my whole stuff was, it's very clear that at some particular stage, this movie's going to end. And unless I'm willing to commit for another five, six years, and that I wasn't willing to do because of that, 60 or five, but I wasn't willing to do that. So to me, that was clear, I got to go. Right. But what became unclear was, what do I do? How do I do it? What do you mean, like, you got to go. And that was, that's where you had, I didn't have fear, uncertainty and doubt you don't want to talk about it wasn't fear, uncertainty and doubt? I would basically say it was a combination of three different words. 

So one was a certain sense of unknowing, right, like, what am I sort of unknowing sort of lack of clarity. And as a strategist, and as someone who was working with a lot of things, I used to be able to have clarity, but sometimes when it's yourself involved, you don't have as much clarity, so that was why I had to go get help from people, so that was one lack of clarity. The second was that I couldn't basically sort of explain until later, like, what exactly did I want to do? I knew I had to leave. But what exactly are you going to do? Are you going to stay at home? No, I'm not going to stay at home. So what are you going to do? And is this thing real? Or is this something different? So that was that? And the third was a slight sort of questioning capability? Which is, can I do this by myself? I've never done anything by myself. And I'm doing this by myself. And I wasn't really by myself, I would have people but I always worked at a company, I'd never been a company of one. Right? So it was like, those were the concerns. It was not fear, uncertainty and doubt. But there were some flavors of that. It was for lack of clarity, lack of being able to describe exactly what you were doing. And then some questioning as to like whether I could do this by myself. And that was the emotion.

Chaz Thorne: What has happened in the two years since other than remaining on with advising the other piece of what you said you wanted to do. 

Rishad Tobaccowala: What has happened is two years later, instead, that'd be the best decision I made. Okay, so, and in part, because I'm still connected in some ways to how the decision gets made. But my book came out, which has done well and continues to do well. So I came out with a book called “Restoring the Soul of Business: Staying Human in the Age of Data,” and that was one and also because of my hunger to learn COVID plus the birth of Substack, I started a thought letter, I call it a thought letter as the newsletter. We just started as an experiment to write, just to figure out substack. 

So my writing career, which is my one to many, has taken off my one to some, my speaking career, my one to some, has taken off oddly helped by COVID because of two reasons. One is I could be in many places without having to physically travel. And people realized, hey, it doesn't matter where he is, we can get him. And because I did not have to move, it turned out to be a bargain price for them. And the last one is that my advisory business worked out really well. Primarily the new things were in private equity because private equity was looking for sort of guidance in particular areas as well as startup, but my big focus and the big learning that I had over the past two years to actually succeed, and obviously generalizing and simplifying, but I really do believe there are only two, which is to embrace technology had to upgrade talent in today's world, so to embrace technology to leverage it as much as you can to understand it, and when disruptions or opportunities it can bring, and then it's to upgrade your talent, which is, it could be your existing talent, or bring in new talent or some combination. And I began to realize that my superpower, if I had one, was being able to help companies upgrade their talent. But because I knew enough about technology, I could do it, I could talk a little bit about where the world of technology was, but my upgrading talent was only about technology. So my basic belief is, Hey, your point of leverage is just imagine if you take your talents and make them 5% more productive. Think about all these things, just make them 5% more productive. And then my whole stuff is, I think I can help you towards that 5% in less than four hours.

Chaz Thorne: Obviously, you're Tough Call worked out, which is great to hear. When you look back at it, though, either the process of making the decision, how you communicated the decision, anything that happened afterwards, is there anything that you may do differently if you have the chance to do it again?

Rishad Tobaccowala: So the two big things for me that if I knew this, earlier, everything would have been much faster and easier: So it wasn't that the journey gave me the stuff, it was so obvious, but my whole stuff is somewhere in all this, like nonsense, I forgot it, which is, hey, what you do is you help see, help people see think and feel differently, and you help them grow. And like it is not really powerful, but I wish I had come up with it before. Right? Advice coming up with grow yourself, your teams in your business that allows me to be personal coaching, or a company, which is very different. 

But the other one really is developing a website, developing the substack, which came a year later. But you know, having a write the substack would have helped me if I had that, and I had you know, 20,000 readers, it would have helped me launch my book even easier. But what happened is now everything is self-serve, people basically come to my website, they subscribe because it's opted to my substack, right? And then they basically asked stuff, so literally, people will come and so can you speak about this article that you wrote? Can you do this? So everything is people come to me and say, here's what we want. And here's how we want it customized. And they tell me how they want it customized. So they do a lot of the work. And I do a lot of the delivery. I should have received this because I was telling people about Google and Facebook when I was working at Publicis, right? But the inability to know what my real superpower was, and inability to figure out what the model was, even though both of them were staring me in my face. Right? And the only learning besides like I've done and it takes me time to figure it out. I think really what it was because I was dealing with all this emotion of like, how do I get out? And what do I do? I couldn't think about how do I sell myself? So it was the extraction process? Versus what's the pure sale process?

Chaz Thorne: Are there any words of advice that you would share with someone who comes to you who's looking at making a similar decision? Tough Call around having a career 2.0? Or, in the case of many younger people now 3.0, 4.0? What would you say to them in terms of how to make that decision for themselves.

Rishad Tobaccowala: So what I would say to them is number one is ask people you trust, it may not necessarily be in your company or in whatever you're doing. But ask people you trust. And that is in addition to a partner you might have who might be emotionally attached to this, but ask people you trust to and work through them what you're trying to do, because they will give you guidance on how to do it.

So my basic belief is if you want to do it, that's fantastic. So now the only questions you have are how to do it, which is what you need to ask people to do. The second is try as far as possible to recognize that you're going to have a four year career and therefore you're going to have many exits and try to make those exits as elegant as possible. So even if you don't like your company, you don't like what you're doing, don't basically do a Jerry Maguire, try to do something a little bit more elegant. It might not feel good that you can't blow up something as you leave. But it would serve you well, you know, unless you're obviously trying to blow up some dastardly evil scheme, obviously, then that's a different thing. So that's the second thing. 

The third part of it is, be patient. And be kind to yourself and don't hold yourself to a very high standard in trying to figure this out. Because you've unlike, usually, when someone leaves a place, one of the reasons they leave the place besides their boss not liking their boss, is they don't believe they're growing anymore. But that means they're really good at what they do. But when you're trying this, you don't know what you're doing. And you try to hold yourself to the same standard which is I could do that in my sleep. How come this makes me lose sleep. So that would be the third one. So it would be to ask other people, be elegant about exits, and be kind to yourself.

Chaz Thorne: Rishad provides a lot of great thinking in this episode about what to do after you decide to bring about a major shift in your career. But what process can you follow to make that Tough Call in the first place? Many of us can get caught in our heads when we're faced with big decisions. And this overthinking results in overwhelm, and oftentimes, ultimately inaction. 

In a letter to shareholders in 2016, Jeff Bezos, the founder of Amazon, said that most decisions should be made with around 70% of the information you wished you had. To make this tangible for your decision around a career change, make a list of the 10 Must-Haves required to move forward, though, you could likely make a much longer list, when you get past that 10 you're likely getting into less critical details that can be dealt with later. 

From there, it's pretty simple. 

Once you've checked off seven, move forward while continuing to work on the three elements that aren't quite there yet. Interestingly, this exercise is also helpful if you're the opposite type of person who jumps into big decisions without thinking them through. By forcing you to pause and think of a list of things you need to have in place before you leap, you're much more likely to be making a thoughtful rather than an impulsive choice. 

For a free download of this tool, go to and select defeat analysis paralysis under decision-making exercises. If you'd like to learn more about Rishad and sign up for his weekly thought letter, you can check out his website at

And if you'd like some assistance with your own tough calls, we've compiled a collection of free tools just for you. Go to to check them out. If you're not yet a subscriber to Toughest Call, please add us wherever you listen to your podcasts. Thanks for listening. I hope this conversation helps you when faced with your next tough call.

Chaz Thorne breaks down Rishad’s three guiding principles for making a successful career transition—watch the video analysis

Rishad Tobaccowala

Rishad Tobaccowala is a futurist and keynote speaker who advises global businesses. He is the author of “Restoring the Soul of Business: Staying Human in the Age of Data.” Rishad also publishes a weekly thought-letter, “The Future Does Not Fit in the Containers of the Past,” which is read by 25,000 subscribers every week including industry leaders from around the world.

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