Ollie Ollerton is a former UK Special Forces Operator and familiar face of Channel 4's "SAS: Who Dares Wins". Now a best-selling author with titles including "Break Point" and more recently "How To Survive Almost Anything", Ollie also runs coaching courses for corporations using the lessons learned from his experiences.
TD: Before I set the recording we were talking about “experience” and how it's very easy to say “oh he’s experienced” or “she’s got experience” without really thinking about what “experience” means. So what I’d like us to explore is the question of “at what point does someone become experienced?” or more specifically, “when is experience realised?”. Is experience realised when you do something for the first time, is it when you teach something to someone else or is it when you use what you have learned to plan something in the future?
OO: I think we have to understand that there is a big difference between “an experience” and “being experienced”. You can't be “experienced” unless you go and experience - that’s really the starting point.
You then have to understand that it takes effort to put yourself into that short term discomfort, when you're going through uncharted territory - and this is stuff I've learned through my experience - when you enter unknown territory your mind is reluctant to embrace it at first. Your mind is always going to want to go back to the more familiar. So when people step into that discomfort zone they will often have a small honeymoon period when it feels good and then when the hard work really starts that's when they can lose appetite for it.
Now there’s two things that might have happened there - they haven't really understood that there is going to be a level of discomfort to get anywhere, to change anything, to do anything. To change any negative habits, to have any kind of really fulfilling experience you're gonna have to feel uncomfortable for a short while. You also have to really make sure that your reason for doing it is worthy of the discomfort you're going to go through because if the “why?” is not strong enough, as soon as it gets uncomfortable, you're gonna walk away. That’s when you slip back into what is more familiar to you, that’s what we call your comfort zone and in that comfort zone there's no growth. There's no fulfilment, there's no satisfaction whatsoever, it's just familiar, a snapshot of the past.
To change any negative habits, to have any kind of really fulfilling experience you're gonna have to feel uncomfortable for a short while.
TD: And what was your military career like in terms of a learning curve?
OO: For me it was a massive learning curve as a civilian going into the Royal Marines. I was 18 years old when I joined and really from the age of 14 I wanted nothing more than to join the military. I just felt it was my calling. I was decent at school but I just lost all interest in it. I could not understand why I was going to school every day to learn stuff that I really had no passion for. I couldn't see the relationship to me and how that related to me after school so I just lost all interest in academia.
Looking back I think “bloody hell 14 years old is quite a move to say I want to be a Royal Marine and that's what I'm gonna do”. I look at my son now he's 21 he’s unsure on what he wants to do. I did have some military history with my family so that kind of further furnished that passion I suppose.
Joining the military itself was a massive learning curve and as with any kind of elite fighting unit you don’t get much time to palate things, you have to stick with it and that's why it can be pretty brutal. That’s why not everyone passes the course and becomes a Royal Marine commando. When I look at it I think that the transition from civilian to Royal Marine was harder than that from Royal Marine to special forces.
TD: And with such a hard and fast learning curve, how do you make sure you take stock of the lessons you learned along the way?
OO: You make sure you keep looking behind. I’ll use my recent climb of Mont Blanc as it’s a useful analogy actually. I remember the going was so slow due to the altitude, I wasn't my fittest so I made it really hard for myself. You’re looking at this never-ending summit which is so overwhelming. I found that when I got into those moments, when your mind starts to think “why do I want to do this? What’s the point? It seems like I'm never gonna get there? Everything is against me.” All it took was a moment just to stand, turn around, breathe and look back - and that really makes you understand the depth and the clarity of that journey you’ve already completed.
You shouldn’t always be looking forward, sometimes you need to look back and reflect. We think we've always got to reach that summit but it's so important that we keep looking back and take stock of everything we've done, everything we've learned, how far we've come and the fact that we're still here.
We think we've always got to reach that summit but it's so important that we keep looking back and take stock of everything we've done, everything we've learned, how far we've come and the fact that we're still here.
TD: So would it be fair to surmise that you can’t know if you’ve learned a lesson if you don’t know what problem you set out to solve in the first place?
TD: You will often hear that when an individual joins the special forces they start from scratch in terms of rank, to a layperson like myself it feels like more of a democracy of experience. Is that an accurate image?
OO: Yeah absolutely fair to say that it's like you start again once you pass special forces selection. I’ve always said that selection doesn't train you to be a special forces operator. It is a test to see if you have the mental robustness and the capacity to be able to learn new skills very quickly as part of a team.
TD: What do you think are the benefits to that kind of approach? That “democracy” of experience, for want of a better word.
OO: At the end of the day you've got to respect it. You can't have people coming in thinking because they were a certain rank they've got some kind of superiority. That’s because being a special forces operator is a very different job, the way you operate, the way you follow orders, the whole command structure is totally different. You have to be flatlined straight after selection, you’ve got your skills and your prowess and your rank will be appreciated at some point later on in that journey but at that moment when you first join that unit you have to learn to work together.
One thing I'll say about special forces teams is that they are more a group of leaders, as opposed to in the big green army where you have one bloke telling the rest what to do. When you get a special forces team it's very much a different command structure and you obviously do have a team leader but everyone is an affected member of that team and everyone is contributing to what that team achieves.
TD: That’s a really interesting point, going back to our theme of experience, on whether there is strength in a hierarchy of experience or more a cauldron or conglomerate of experiences. Maybe that’s a lesson that should be transferred to civilian life, that sometimes actually a high rank or position doesn’t always mean the one who has the best or most valuable experience.
OO: Absolutely, we take this old, archaic view of hierarchy which doesn't work in a corporate structure - you can’t militarise a corporate structure. However, there are things that you can take from the way we as operators used to work and put that into a corporate structure and allow everyone to benefit from that.
For example, in a four man team you need to be able to make decisions when the pressure is on and this comes down to effective leadership. You've got to have a team leader that can relinquish control when required. You've got to understand that a lot of the time some people have better ideas than you, have certain skills you don’t.
Being an effective team leader is more about coordination, more about delegation and more about the motivation of achieving the goal. You can’t have the person in charge so insecure that he has to do everything to prove that he's the best, that doesn't work. Anyone who does work like that is acting from a place of insecurity.
We take this old, archaic view of hierarchy which doesn't work in a corporate structure - you can’t militarise a corporate structure.
TD: This takes us to our next section nicely. So far we’ve talked about the idea of doing something and getting experience from it, in the next I’d like to talk about how we pass on that experience to others. Let’s talk about your books and your coaching work and how you transfer your experience into teaching others.
OO: Yeah so when I receive feedback on my talks, most people say “well it was great but it wasn't what they expected” and a lot of the time people expect it to be all about war zones, all about special forces, this that and the other but that was only a part of my life. Whilst that taught me some really great fundamentals, I've done a lot more since then. When I look back on my life really I look at my special forces experience and the training and everything I went through and really that was preparing me for the biggest battle ever and that was the battle with myself. When I left the special forces I spent a long time in absolute turmoil, I didn't know who I was. I had no idea where I was supposed to be, I was doing what I was expected to do and not what I wanted to do.
TD: This is maybe a slight tangent but do you think that this could almost be interpreted as being caught up and maybe held back by experience? It must be really hard to look forward when you’ve got so much behind you that is so different to what you’re moving towards.
OO: And that’s why people have got to understand that experience isn’t specifically about what you do on a weapon system or firing range, experience is your wisdom, it’s your mindset - everything is all about your mindset. You can't do anything without this, people tend to separate mind and body but there's no difference between the two.
It all starts in your mind, people say “well how did you manage that physically” but nothing happens without the mind. This is where people leave the special forces and they think that their training, that everything they've done is linear. So they go to war zones as a contractor and all these similar kind of industries.
Look at Louis and Staz though, from special forces operators to entrepreneurs, business owners with a clothing brand. That is not the natural way to go but the fact is that what matters is that drive, that determination, that mindset that you can put into anything. It doesn't matter where you go, but the thing is once you label yourself you limit yourself and this is what the majority of people do. They think that they have to fit into this box that society provides and that's who we are and that's our identity and it's not.
For me that really started to change shape after thinking about contractor work, thinking that was my calling, I could earn loads of money doing a job that I have the credibility to do but really it was the worst place for me to be. I now call it “fool's gold” because I will never go back and do that job again, not for what it cost me mentally.
It wasn't until I stumbled across an experience in Southeast Asia when I went across and worked on anti-human trafficking operations. Rescuing kids from prostitution and slavery, that changed my life and that was the power of helping other people. I wasn't being paid but it was the best investment I've ever made in terms of feeling personal fulfilment.
TD: You've already touched on the feedback you've had from people who have attended your talks and read your books, is there ever a way that you can really validate that what you've taught has sunk in? How do you measure how well your coaching and your books are being received in terms of lessons learned?
OO: For me it’s when I get messages on email or on Instagram about how a certain book has changed someone's life, I’ve had them from people at the brink of suicide or massive trauma in their life. My first book was “Break Point” which was really about the foundation of who I am, what I've been through, my experience and what I did to myself when I came back from overseas. I was literally at breaking point, I had no money, nothing, I had problems with alcohol and drugs. Then one day I told myself “this is not happening anymore”, my everyday life had become a repeating pattern of the past.
So I set about to change and that's when I shut myself in a house for three months where I worked on these habits and behaviours. It was the time spent in that house that laid the foundations for my new life and when I emerged was when I got my first big break with SAS: Who Dares Wins.
I've not stopped doing the things I learned in that house in 2014 so that was an absolutely amazing transformation for me and it's great for people to understand that if you are having a bad time, if you are really in a bad place you can change. Because people think that they're locked in, that they can't get out - but you absolutely can. It takes a lot of determination though and a lot of work to do so.
When I look back on my life really I look at my special forces experience and the training and everything I went through and really that was preparing me for the biggest battle ever and that was the battle with myself.
TD: My next two questions are a couplet if you like, my first thought being what does experience become when it’s been taught? For example, you might teach me your experience, but I wouldn’t then consider myself “experienced”. And that then begs the question, do you think we confuse “knowledge” and “experience”? We might read something, or watch something but what is the value in that compared to actually getting out and seeing or doing that thing for yourself?
OO: The problem is we have far too many people engaging in “mental masturbation” these days. There’s so much to read and watch online but so little of it is of any real use. You’re best off triaging in this situation and looking at three or four smaller pieces of information and acting on them - because regardless of whether someone else has experience of something, your experience of the same thing is going to be totally different.
That’s why my goal is to use my experience to give just a bit of direction, to get people to take that first step into discomfort. But there are a lot of people out there that haven't got the courage to step forward and actually do something about it. You need to take that step forward because nothing is anything without taking action that actually counts. And when you do you can always take a step back and go “well my experience was totally different but because I’ve done it once, I can make that step again in future.”
Look at the likes of Roger Bannister and the four minute mile. None thought it was possible for a human to run a four minute mile until Roger Bannister did it. Before you knew it, a few years later everyone was then running four minute miles. And that is how experience can create belief.
TD: I guess it almost sounds like a test and learn process? A hypothesis of sorts? You try it, you see how it goes and it might take you one way or it might take you another.
Moving on to our final area of discussion, we have the question of “is experience realised when planning for the future?”. To think about this I’d like to talk about your upcoming expeditions and whether you have a template approach to planning expeditions based on what you have learned?
OO: Yeah so I climbed Mont Blanc in 2019 I think it was and then last year I climbed Ama Dablam which was amazing, absolutely amazing. Then next year I plan to climb Mount Everest. So for me it's fundamental that we do those things in a chronological order so that I can gain the experience to go and do something greater each time. I'm all for optimistic challenges but you've got to make sure that you're getting in the experience en route to that.
For me, at the moment, I know exactly what my mind is doing to prepare for this and once you gain awareness and you start to analyse your thoughts and understand why we think the way that we do, you start to see how the mind is trying to protect you.
Preparing for Everest there's a lot of procrastination starting to work its way in. I can feel it, I know what it's doing - it’s the mind really trying to protect the species. So to combat that you have to really commit to something that you want to do and the best thing for me to do right now is draw a line in the sand and commit. To forget all the stuff in the middle, forget your mind telling you “oh what about this? What about that?” Forget all that rubbish, when your mind can't see the target it thinks it can’t be done - it wants to see the blueprint first.
You have to understand that when you want to do anything that you haven't done before you need to chart your own course, don’t follow the footprints of anyone else. Start by setting a goal and then you work backwards until you can visualise the path from back to front or top to bottom. If you do it the other way and you start by pushing forward without a clear end point or destination, it's like trying to push that mountain towards nowhere.
It doesn't matter where you go, but the thing is once you label yourself you limit yourself and this is what the majority of people do. They think that they have to fit into this box that society provides and that's who we are and that's our identity and it's not.
TD: To pick up on something you said at the start of our conversation, would it be right to say that the incremental approach you described, to keep checking back helps you manage your goal setting once you’ve drawn that line in the sand? To borrow your analogy, Everest might be 8,000m plus but you don’t climb it all in one go. Does that kind of incremental approach help keep the procrastination in check?
OO: Yeah 100%. For example, I know that Ama Dablam is 6,189m or thereabout - I didn't measure it. So I know I’m capable of 6,189m of Everest’s 8,000m plus. I’ve done it before.
TD: And when you are using what you've learned to move forward how do you make sure and keep in check that it's not dogma as such and that you don't lose that degree of flexibility? Because with experience there must also come a flexibility to assess and readjust at any given time?
OO: You have to remain dynamic on these things, I don’t think I’ve ever stuck to any plan ever. But you have it as a framework and that is what you’re taught in the special forces so that when you do have a structured plan and it goes wrong everything doesn’t fall apart. Life gets in the way, challenges do crop up, I’m guiding a 160 mile loop through Colorado in two weeks time but I see that as a stepping stone in the bigger Everest picture, not an obstacle. The focus has to be that one day I’ll be on top of that mountain. Your focus cannot be on the journey and the problems you might encounter, you have to visualise what you want and what that feels like. Then it becomes about creating that feeling and making it reality.
TD: Goodness, so I set these questions quite wide and maybe I didn’t truly expect them to be answered but I think this has been a really interesting assessment, obviously taking in your background, your experience and the lessons we can learn to help us move forward. What I’m taking away from this is that the nature of experience is so much bigger. It’s very much an incremental process “Right I’ve done this - bank it. I’ve now done that - bank it.” it’s not a linear process in the sense of one day you’ve not got it, the next you have. It’s constant.
OO: I mean yeah, to me I’ll always have experiences but I’m never going to be “experienced’. There won’t be a day where I sit back and go “I’m the one source of knowledge” because every day is a school day and I’m going to go to my grave not knowing things. But while I’m here I’m going to learn and experience as many things as possible.
I think, at the end of the day, the reason we see so many mental health issues at the moment is because we’re not setting enough goals. You always need to be aiming higher relative to where you are right now. Because the moment you accept what the mind wants you to do you slip back into that comfort zone and you take the path of least resistance. It does take a lot of effort to step through that, but you have to do it.
As humans our instinct is just to survive, it’s the dominant strength above all else. Yet our soul wants to experience, it wants to seek adventure and do these great things. And that’s where we encounter this friction. Technology is flying past us at an astronomical rate and yet our primal instinct remains the driving force in each and every one of us. And that’s a topic we don’t have time to get into today George!
The focus has to be that one day I’ll be on top of that mountain. Your focus cannot be on the journey and the problems you might encounter, you have to visualise what you want and what that feels like.