October 18, 2023

Regan Robinson on spending time in the future, using imagination, things that make you go hmmm, and hyper-awareness (AC Ep15)

“Imagination has a trigger event. It begins with a mental spark that acts as a catalyst, throwing everything into question. It ignites your curiosity and starts shifting your perception.”

– Regan Robinson

Robert Scoble
About Regan Robinson

Regan Robinson is a futurist, business strategist, advisor, and investor working with founders and C-suite executives to help make them future fit. She is currently Chief Futurist and Executive-in-Residence at Happy Ventures, with extensive experience working in startups, high-growth companies, and global firms including VICE Media and Edelman.

Website: www.reganrobinson.com
LinkedIn: Regan Robinson
Instagram: @socialgal

What you will learn

  • Embracing proactivity, shaping the future with strategic foresight (02:50)
  • A holistic approach to futurism (04:35)
  • A deep dive into futuristic brainstorming (10:13)
  • Cultivating well-being and mental agility (13:50)
  • Reiteration of the transformative power of imagination (19:02)
  • Exploring people’s own paths to rest and digest creativity (26:40)
  • Cultivating intuition and overcoming cognitive biases (30:47)

Episode Resources


C&C Music Factory


Thriving on Overload by Ross Dawson


Ross Dawson: Regan, it’s awesome to have you on the show.

Regen Robinson: Thanks for having me. I’m super excited for our conversation today. I love talking with people who share a love of the brain like I do.

Ross: You are a futurist and strategist and you help leaders to amplify their cognition, we could say, to see the future and to create it better. How do you do that?

Regan: In a world that is constantly changing and evolving, which is our current / forever reality, at least I believe, I help people and companies spend time in the future so that they can be active agents in creating it. This is about being proactive versus reactive. I do it in a lot of different ways. But essentially, I do this through insights, tools, and experiences that empower visionary people and companies to see and think differently, so that they can gain the confidence that they need to strategize for the future more effortlessly.

I like to say sometimes that I’m a Michelin-starred chef, where I’m constantly experimenting with inventive recipes, I’m trying out new ingredients, and I’m trying to push the boundaries of our profession as futurists, as much as I can. It’s in response to the biggest mistake that I see which I’m sure you come across or encounter a lot as well, Ross, is waiting until it is too late to think about the long term. Short-termism is the greatest threat to your company or your career. I think it’s the biggest reason why it or you might not be around in five years, I think it’s a major contributing factor to why nine out of ten companies fail. That’s why I just think it’s so important. It doesn’t matter if it’s your business, you’re working in someone else’s business, so a lot of what I do and talk about is applicable in your own career as well.

Ross: You use the phrase spend time in the future. How do you take somebody to spend some time in the future?

Regan: I know, it’s funny, as I have been on this journey the last few years, especially focused on being a futurist. The language is always interesting. People are like, what! Spend time in the future? What the heck does that mean? Again, there are a lot of different ways that I do that, whether it’s workshops, whether it’s programming, whether it’s a multi-month journey, sometimes I actually go in-house and do things for a longer term. But, what all this is about is foresight, as you know. A lot of what I do is around my approach to foresight. It is complimentary to some of the traditional methods, it’s actually a little different in three ways, and I’ll share the top line, and then we can kind of dig in.

First of all, it’s holistic. I am a generalist futurist and I use a unique blend of hindsight, insight, and foresight across a litany of topical areas. I don’t go super deep in AI. If I need that expertise, I bring that in. I have my fingers in a lot of different areas. That enables me to bring a big picture, divergent thinking, and possible futures together that my clients and those that I work with aren’t even considering. It’s more than just connecting dots, it’s like no, actually, here are dots that you’re not even seeing. One of the biggest problems I see is when people are narrowcasting, they’re focusing on the familiar, they’re in their own echo chamber of their industry or who they’re talking to. My approach tries to kind of break people free of being stuck, where they are currently.

The second thing that’s a bit different is it harnesses imagination and intuition. These capacities drive the process to enable a more continuous dynamic way of being, as I like to say. It fosters iterative learning and discovery. While there is some data involved in the process, it’s way lighter than what I would say some of the traditional methodologies that I used to use before I landed on this new way of approaching things.

Then the last thing is, it’s mind-body connected, and there are two parts to this. First of all, practicing well-being in my view is a foundational skill set, individually, as a team, and as a company. That’s because you have to create the conditions for this way of thinking and being. You have to activate your rest and digest nervous system as opposed to your fight or flight. That is key. If you’re not starting there, in my view, why even bother? You really need to set that foundation.

Also critical to that is recognizing the unconscious biases, limiting beliefs, and assumptions, and taking action to prepare your mind, address those emotions, challenge assumptions, and get unstuck. This just popped into my mind, but maybe it works. It’s like you’re cleansing the palate before the work actually begins, before you even start to spend time in the future or think about big ideas or something long-term. These are all much harder to master or even practice than perhaps it might sound initially. This work, I would say, is not for the faint of heart, but I believe that there are superpowers and when you combine them together, they’re almost the ultimate superpower. Because at least in my experience, to date, very few people are cultivating all of these things at the same time.

Ross: Fantastic. One of the classic things around working with leaders around the future is, first thing, you have to get them to believe things they wouldn’t have believed before. You have a certain belief, okay, this is the way the world might work or it might happen. Then, to create value, you have to get them to think more things than they’ve thought before, to believe, Oh, I never even imagined that, I never conceived of that before, now, I’m aware of that and can understand that or things I didn’t believe were possible, I now believe are possible, things that need to be incorporated into our thinking. It’s all about essentially expanding the scope of what they think and what they believe around what could come to pass. How do you create experiences to take leaders to that place? 

Regan: I do. Again, there are a lot of ways that I approach this. It depends on where I’m meeting people. Because sometimes I work with people, they’re on the bus, so to speak. They get it, they realize, wow. They may not know all the stuff, but they’re like, well, I’m ready for this, I’m ready to take the leap. Then there are people who are on the opposite side of the spectrum and need more work. One of the things that I try to do, sometimes maybe a bit much for people, but it always works is we try to open the aperture as big as humanly possible.

What I do is I have them do different types of exercises where they are, independently or with their team, really brainstorming. Okay, what are sort of the big things that could impact our future? What are the major disruptive forces? Because it’s always still going to be through their lens that we think might be important, or could impact the future of our company, our customers, etc.? Nine times out of 10, what they come with is super small actually. But yet they’ve thought because I’m like, No, go big, I want to see all kinds of post-its, I want to see something totally crazy, and they thought they’ve done the exercise.

Then when I start to say, Okay, here are all the other things that you weren’t even thinking about. Sometimes I’ve been told, sometimes it can be kind of fire-hosey, like, Wow. That starts to open their mind to the fact that okay, I made, first of all, assumptions about what I thought was going to impact me, I didn’t really realize this over here, or I could have forgotten, maybe I didn’t think this is important, but you’re bringing this to the fore, and then I try to go through. Sometimes what takes some time is what if, what could be just… my goal is to try to get everything out on the table that we possibly can before we even go to the next step, which is more where, in my process, ownership and intention come into play, but let’s get everything out so that we can see as many possible things as we possibly can as a starting point. It also is helpful because then we can put things in the parking lot. I’ve just found it’s a really great way to help people realize, okay, wow, clearly, I was thinking like this, and I need to start thinking like that.

Ross: Fantastic. The exercise is essentially you start yourself, then see that there’s a lot bigger space, and then be able to just acknowledge that there’s more there and to see a bit of the scope.

Regan: Yes. I also try to throw I might say, what if, then I start to connect dots, maybe that they’re not thinking about. I think that’s also too… because we’re innovation… the future is already here, it’s just not evenly distributed – one of the best quotes ever, because it’s so true.

Ross: Yes. As I wrote in my book Thriving on Overload, part of the process is being able to nurture an openness to experience, and part of it is…There are many, many ways to be able to approach that. If we’re closed off to new ideas and thoughts, then we’ll always be limited. We have to get to a point where we are open not just to accept but also to look for and to see things that we wouldn’t have seen otherwise. That’s part of a shifting process. There are many ways to do that. That’s one of the things you’re doing here is to nurture the saying, Oh, I have been close, I have had my blinkers on, now I see the value of opening out and hopefully, that’s creating some lasting shift of being more open to ideas and thoughts or things that weren’t part of the everyday.

Regan: Exactly. The other thing that I would add, as I mentioned a few moments ago, is the well-being component of it. Well-being is a complex concept. But to me, it’s more than physical vitality, includes good mental health, high satisfaction, purpose, and the ability to manage stress. While the research on good health and performance is clear, well-being in that context isn’t exactly what I’m talking about. That’s important but I actually have two other things that I look for in people before I work with them, is having the mental clarity to imagine what could be, so you have to address, you have to have your wellbeing house in order to be there. This is also very important, letting go of fear and ego, and having faith in the future’s possibilities rather than coming from a place of scarcity. Because the data on anxiety and burnout that people are experiencing is overwhelming.

I think there’s a lot of baloney and lip service out there happening around what companies are actually doing to address this. I have conversations with Chief talent officers and what they tell me is, frankly, quite shocking. That’s why it’s important to understand where people are at because when they’re exhausted, before tired, you fall into a scarcity mindset. You think about what you don’t have, and you’re not as adaptable, you’re not as open, you’re not as open to learning or new ideas. Again, if you’re not starting there then already, you’re at a deficit. Just like professional athletes who continue to invest in their physical and mental health, not just before the race, but it’s all the time, I believe that leaders have to be fit to face whatever comes their way and for however long it takes, so they can support themselves and others.

I often joke when I do speaking engagements that if every executive had a psychotherapist and executive coach, we could all work together better, and we could all clock in about 20 hours a week. Now, I’m not totally kidding when I say that, from personal experience as well as what science is starting to tell us, the other aspect of this is we’re preparing our minds. If we’re an athlete, we are preparing our minds. You have to recognize unconscious biases, limiting beliefs, and assumptions. There are nearly 200 cognitive biases that affect our thinking and decision-making. The sheer number in and of itself should teach us some humility about what the brain can do.

On top of that, if that already wasn’t hard enough, there are a lot of psychological barriers to future-mindedness. It’s the tyranny of the urgence. Being crazy busy enhances our perceived status and self-worth. I always say busyness is the new stupid. I’m starting to believe that maybe I need to make this into a t-shirt. Part of why I do that’s a lot, right? Part of it is figuring out where people are at whether it’s an individual, their company, or their team, and then figuring out okay, what are the most important things on a psychological level? On a wellness level? If people come to me and if they feel harried, I’m like, that’s not the time for us to work together. Because I just know the job to be done is going to be that much harder.

Ross: Yes. We know, and there’s plenty of research that shows that if we are stressed and anxious, our field of perception, both visual and also in terms of just the world, narrows. It’s surprising. For stress, probably we should be focusing on something right in front of us. We need to get beyond that to be able to perceive more broadly.

Regan: Exactly.

Ross: Part of that journey is imagination. You can provide some of the pointers to say, Oh, you missed that, and here are some other things you hadn’t thought about. But of course, they need to be able to do that for themselves to imagine what might be possible and how they should be preparing for that. How do you take people on that journey of nurturing their imagination?

Regan: Again, the athlete who is constantly conditioning themselves, I advocate for, same goes for this. I hope that you actually never stop because in my personal journey, as I went from a former type A overachieving stressed out 100-hour week executive to who I am today, that was a seven-year journey, and I’m a vastly different human being. The way that I work and the things that I see, you can’t even compare. I’ve actually done the work myself and walked the journey so I can empathize. I get those people because I was them. I was you.

At the simplest level, imagination is the ability to create an idea of something that doesn’t yet exist. It allows us to explore what’s possible. It’s like a mental mining expedition into uncharted territory. We have a long way to go to fully understand what imagination is but we do have important insights about it from cognitive science, neuroscience, and humanity. Imagination is actually a neurological reality. Our brains are constantly updating with numerous cognitive functions that enable this awesome power that we as humans uniquely have, which is also super important in the age of AI.

As we think about imagination, three aspects to the process are important to understand. The first one is that imagination is about relationship-building and connection-building. We do this by combining and restructuring things to explore ideas and to create new, meaningful relationships between them. The second thing is that time and perspective play a role. Imagination is a method of thinking and framing that allows you to step into the present, revisit the past, and then anticipate possible futures. The third thing that is important to know about imagination is my absolute favorite, is imagination has a trigger event. It begins with a mental spark that is a catalyst, or surprises that throw everything into question. They spark your curiosity and they start shifting your perception.

To answer your question about how I start helping people with this is…One, just even understanding that this is how it works. I remember when I first learned it, my mind was blown. I couldn’t believe it. I was like, Wow, all that stuff is actually happening unbeknownst, in our subconscious, we don’t know that this is actually happening. What I do with clients and people that I work with are three things.

First is helping them get intentional about what they care about and what drives them nuts. Because aspirations and aggravations relevant to the work that you’re doing will enable you to notice triggers that form the building blocks of imagination. For example, I care deeply about helping leaders create the space for emergence, getting them out of the day-to-day so that they can create this continuous future-focused growth. I am very passionate about pioneering alternative ways to build funds and grow companies because much of what I see isn’t sustainable or working for most people. We desperately need to reimagine business models, funding options, and roles. That’s what you and I talked a bit little bit about on LinkedIn. These are some of my aspirations and aggravations that are always bouncing around in my head.

The next thing is to notice productive surprises. You laid the groundwork with your intentions, and then you have to prime the mind. Surprising events are everywhere right, it rains, you weren’t expecting it. But the triggers that are useful for our imagination are the ones that challenge our thinking, that seem out of the ordinary. My shorthand for this, which I’m dating myself into… is the C&C Music Factory song from 1990, the things that make you go Hmm. Many times, I could feel in my body the things that make me go hmm, that is something that might be worth exploring. To continue the thread on my example that I’m sharing, several years ago, I experienced a triggering event that compelled me to start developing a different way to approach foresight. I was talking to the CEO of a venture back scaleup about my consulting offerings. What she said doesn’t matter. But it gobsmacked me. It was just like, woah, out of the ordinary. This surprising conversation triggered my imagination and threw everything into question. It caused me to get curious, ask what-if questions, and think about, okay, what could be new potential courses of action.

Then the third thing or component of this is creating the conditions for productive surprises. Again, your mind needs to be prepared to act so that you can see and sense things more deeply. This is where it connects back to the well-being component is we know from neuroscience and cognitive science that you actually have to be in a rest and digest state, not fight or flight, to harness your imagination. I was blown away when I learned that. That is why you have great ideas in the shower, or while you’re taking a walk in nature, and so the only time that your mind can start making those relationships among things, playing with things in a new and different way subconsciously, is if your rest and digest nervous system is activated.

Ross: As you say, the imagination could spark by these surprises or productive surprises. Part of it, as you say, is being in a more open state of mind, more clustered off-state. But there’s more to it than that. Because I think there are some people whose imaginations are sparking all the time. There are others who we can probably observe outside and maybe their internal experience is they’re not imagining lots of new things all the time. There are times of the day or times of state of mind where we are better prepared for it. But I think there’s a longer process of nurturing that ability to imagine. How else? Again, the mind-body, which you described, is all part of that as well. Is it seeing the value of imagination that people start to do that? Is it just simply being aware of that? What are other ways in which we can get people to be more prone to imagining?

Regan: That’s a great question. I think that is the starting point. Because it is a lot for people to process. I discovered this two years ago, and it’s still knocking around in my head. I think that’s a great jumping-off point. You can take it to the next level. Again, awareness is half the battle with a lot of these things. Things like mind wandering, or daydreaming, actually making this a habit. Because people are going to have to experiment with what is going to work for them, not everything just because daydreaming or walking through nature might work for me, I’ve actually had people tell me the things that I would have never anticipated is actually what gets them into that rest and digest state. I do feel there’s a little bit of personalization and experimentation that needs to happen.

A lot of it is also just the awareness of okay, I’m so excited to read your book because I think there’s a lot of harmony between our work and you probably have a lot of thoughts on this. But, the information by which we’re seeing, the amount that we’re seeing it at, it’s a lot. I’ve found at least in my work and my own personal experience, by starting to practice this hyper-awareness and this rest and digest state, which actually feels very opposed or it’s almost a paradox, but once you get to that state, I don’t want to say I will never, but I’ve yet to meet a person that hasn’t come back to me and says, Wow, okay, I’m seeing things a little differently. I’m connecting things that I wasn’t connecting before. I am using all of the creative fields, art, and music, they have their own raw material, likewise, same goes for this. I’m taking all these different pieces of raw material, and I’m starting to make things into something that I wouldn’t have anticipated, or I didn’t realize that watching…One thing that I love watching are shows…I’m a big history nerd so I’m always watching historical documentaries and just things that I continue to be surprised at how I’m like, Umm, there might be an application way over here. But it’s because my mind…I continue to practice to be hyper-aware but yet in this rest and digest state.

Ross: Yes, love the idea of hyper-awareness. I used the same concept for myself. Part of it is that some people, either don’t want to meditate or say, I can’t meditate, and they just have this thing: meditation is just not for me. Whereas hyper-awareness is, in a way, basically the same thing or an aspect of the same thing but you can bring it to people in a different way, and it’s also completely part of our every day as in saying, I am actually going to be as aware as possible of my environment. It’s actually a beautiful state of mind because you’re living completely, you’re living richly, and you’re not just wandering off thinking about other things, you are there. As you say, that totally brings you into a state of mind that is of openness to ideas, to perceptions, to see more of the world, it is richer thinking, which is what we are trying to engender. To round out, I want to make this as grounded as possible in terms of what it is that people can do. What are any tips, approaches, or strategies that people can implement to take part of the wonderful space you’ve described today into their lives?

Regan: I’d say a couple of things. In the first area around cognitive biases and starting to address your blind spots, step one is to be aware. The best way to prevent cognitive bias from influencing the way you think see or make decisions is by being aware that they exist in the first place. Secondly, challenge your own beliefs. Once you’re aware that your own thinking is heavily biased, continuously challenge the things you believe. This is where divergent perspectives, talking to people…I talk to everybody because I never know what I’m going to learn or what is going to arise from that conversation.

Then, as if I haven’t emphasized this enough, slow down and relax because that allows you to receive stimuli and a very different way than when you’re running around in that fight-or-flight mode. I talked about mind wandering, but there are a lot of different things in terms of switching on your rest and digest that you might not think about, whether that’s listening to music, journaling, stargazing, going on a drive, cooking, lingering over a meal, doodling, gardening, I’ve tried to like capture as many as I can, but doing these things, making time to reflect and to allowing the distractions to come your way.

Then I would say, and this is more on the intuitive side of things, there are a couple of tips that I have. The first would be to prioritize. Establish clear priorities for your work in life because your intuitive responses are driven by the brain’s limbic system which is responsive to whatever you’re establishing as a priority. I love practicing daily pauses, 15 minutes time to unplug, my clip is 20 minutes, every 20, I’m standing up and I get around and move. I don’t care what it is that I’m doing because I feel like that movement recenters me, it clears my mind. I don’t look at my phone, but I’m just actually getting up and moving around, I might just walk back and forth. It’s a game-changer. It sounds stupid. It’s like so simple but I would say it’s pretty game-changing. The other thing I’d say is trust in yourself. 

Ross: Always?

Regan: Listen, it might not always be right, you have to be okay with that. I think that’s more of a question. But when you’re honing your intuition and your imagination, trusting yourself and releasing that resistance, because we do doubt ourselves. Again, this is fear, anxiety, and ego, playing a role. Our cognitive minds may overthink a situation, this is when analysis paralysis comes into play, even though our gut intuition may be telling us something else. Trust yourself as much as you can, like you’ve got it, and then take it slow, and create a practice that calms the nervous system. Stress and overscheduling impede our ability to imagine, to notice, and to use our intuition. All these things do fundamentally come back to that component, which is not easy. I’m not being flippant about it. I know. I’ve walked the path, but it is important.

Ross: Everything we’ve talked about today is all about amplifying cognition. It’s all about thinking better and easier. Many of these things are what people miss. They’re using their electric brain stimulation and all sorts which can be useful but just sitting back and getting into a more relaxed state of mind, and I just say, opening yourself to seeing the world more, has to be the starting point.

Regan: Yes. It’s a marvelous thing. It is game-changing. It truly is. Again, because I operated very, very differently, I feel the difference in everything I do and how I show up and what I’m seeing and noticing and it’s just a marvelous thing. That’s what people feed off of when I work with them too, so I’m like, wait a second, why don’t I show you how to do this? You can do it too.

Ross: Fantastic. Where can people go to find out more about your work?

Regan: You can go to my website, reganrobinson.com. You can also follow me on LinkedIn @reganrobinson, I share a ton of tips, practices, habits, provocations, and perspectives to help you spend time in the future and more. I’d love it if you would follow me there.

Ross: Awesome. Thank you so much for your time and your insights, Regan, it has been a real pleasure speaking to you.

Regan: Thanks, Ross. I enjoyed our conversation. 


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Futurist, keynote speaker, author and host of Thriving on Overload.

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