PTBM Logo H5

Thriving Under Pressure | Simon O'Shaughnessy

Today’s Guest Simon O’Shaughnessy

Simon has spent over 40 years of creating and delivering projects and figuring out this whole entrepreneurial thing! Starting out life as a dentist, moving into the sunbed and eventually the health spa game he sold it all and moved to NZ. Now he creates change and development in peoples lives and their business, with 1-2-1 coaching and mentoring. He's also been doing a lot of short-term change assignments in the health sector.

  • Entrepreneurship is about more than just having a good idea--it's also about being confident and resilient. It can be difficult for entrepreneurs to find the right team members who complement their skillset, but it's essential in order to create a successful business. Resilience is key in entrepreneurship--without it, businesses are likely to fail.
  • As an entrepreneur, it is important to be able to work in the front line and understand what the real problems are. It is also important to have a mind that is resilient and can tolerate ambiguity. Part of being an entrepreneur is learning to be a leader. A leader is someone who works in the front line and has enough capacity to take on other people's problems.
  • Matt and Simon discuss the importance of core values and how they can help you understand when it is time to move on from a situation. For Simon, one of his core values is people. He loves being around people and finds them essential for success. However, he also recognises that as he gets older, he may need to find ways to recharge that don't require so much face-to-face interaction.

Links for Simon

Links & Resources from today’s show

Sponsor for this episode

At Aurion Media, we're committed to helping you set up and run your own successful podcast to grow your business and impact.

"You know what? I have found running my own podcast to be really rewarding. It opens doors to amazing people like nothing else I have seen. I have built networks, made friends, and had a platform to champion my customers, my team and my suppliers. I think just about any entrepreneur, or business leader should have a podcast because it has had a huge impact on my own businesses." - Matt Edmundson.

Is Podcasting Right For Your Business?

This is a great question and one we think you should really think about. Podcasting is proving to be a great tool to open doors to dream clients, network and build phenomenal customer relationships. But we know that podcasting might not be right for everyone. That's why we have put together a free online workshop to help you decide if Podcasting is right for you and your business as well as to understand what is involved for you.

Is Podcasting hard?

It certainly doesn't have to be. The technology has got easier and cheaper, so the trick is making sure your strategy is right from the start. Most podcasts end because it was started on a whim or even a good that just wasn't thought through or planned. Once you've got that in place, it's then about the right guests and consistency which all comes down to the team that you have around you that can help with this. No worries if you don't have a team...Aurion has a series of done-for-you services that can help you get the right strategy and bring the consistency you need to have real impact on your business.

Want to know more?

Visit our website for more info. We'd love to help!

Matt Edmundson: Welcome to Push To Be More with me, your host, Matt Edmundson. This is a show that talks about the stuff that makes life work and to help us do just that. I am chatting with my very great friend and guest today, Simon O' Shaughnessy, all the way from the other side of the world. We're gonna be talking about life as a perpetual entrepreneur, the importance of your core values and making meaning, amongst other things, I have no doubt.

Now the notes and transcripts from our conversation, uh, will be available on the website Also, whilst you are there on the website, you can sign up for our newsletter and each week we will email you the links from the show, the notes they all get sent straight to your inbox.

Auto magically it's totally free. Uh, and so make sure you sign up for that. Now, this episode is brought to you by Aurion media, which helps entrepreneurs and business leaders set up and run their own successful podcast. You know what chief, uh, I just say by the way, lemme just say clarify. When I say chief, I mean Simon.

I've always called him Chief. You'll find out why. Uh, you know what I found running my own podcast to be super, super rewarding. It opens doors to amazing people like nothing else I've seen. I've built networks, made friends, and had a platform to champion my customers, my team, and my suppliers. And I think just about every entrepreneur or business leader should have a podcast because it has had a huge impact on my own business.

Of course that sounds great in theory, but in reality there's the whole problem of setup, distribution, getting the tech right, knowing what the right podcast strategy is, and so on and so forth. You see, I love to talk. I know I do. It obviously goes without saying, uh, but, but I don't like all the other stuff.

Uh, so Aurion Media takes it all off my plate. I do what I love, talking, and they take care of the rest brilliantly. So if you're wondering if a podcast is good for your marketing strategy and for your business, why not connect with them at That's We will of course link to them on our podcast website as well, and their link will be in the show notes if you're signed up to the email.

So thank you Aurion Media for sponsoring this podcast. Uh, and that's. Check that. Check that out. Yeah. Yeah. So let's talk about Simon now. Simon has spent over 40 years of creating and delivering projects and figuring out this whole entrepreneurial thing. Uh, he started out life as a dentist, moved into the sunbed industry, which is when I started working for him and eventually the health spa game.

Uh, he sold it all and moved to New Zealand. Now he creates change and development in people's lives and their businesses with one-to-one coaching and mentoring. He's also ironically come full circle. He's been doing a lot of short term change assignments, uh, in the health sector. So he started out as a dentist and now he runs kind of medical practices in New Zealand.

Uh, so Simon, welcome to the show. Great to have you here. Thanks for joining me. I'm really excited about this episode, by the way.

Simon O' Shaughnessy: Thank you. Matt. What's that? Auto magically a few minutes ago. Yeah. Yeah, sure. Heard you.

Matt Edmundson: Yeah. Auto magically it comes automagically. It's such a great word, isn't it?

Simon O' Shaughnessy: Automagically, it sounds like most of my career.

yeah. Automagically. I'm not quite sure how we got here, but here we are.

Matt Edmundson: You should put it on your business cards.


Simon O' Shaughnessy: automagically. It doesn't, doesn't go down well with the linear people, which, which I actually decided before you asked your question, I think is always the confrontation between an entrepreneur. Yeah. And, and business in the, um, you know, entrepreneurs and I suppose I am one, cuz I seem to keep doing stuff. you can't escape, you know? And, and, and someone asked me the other day, you know, is it always original?

I thought, oh, embarrassingly it probably is. Yeah. You know, I've got the idea from somewhere. I've synergized something together. But actually in the end of the day the output is original. Which, which, which sounds sort of a bit posey really, but I think that is what entrepreneurs do. They, they sort of create something, a step, yeah.

That actually suddenly changes an industry or a product or, or something like that. But gosh, they're not liked by the establishment. Not promoted I feel. No, no. I mean, I, I always remember, I mean, if I was thinking back to early days, it was a long time ago, you know, the things you remember of course from the bank, like, you know, when will we expect more funds, Mr. O' Shaughnessy. Very, very important questions like that for a yeah, who's, you know, shocking things just carry off, you know, have I got to have structure? Oh, okay. You know,

Matt Edmundson: what's that all about?

Simon O' Shaughnessy: Yeah, so I, I, um, I think the more I think about it, the more my life has been about actually protecting that sense of self, that, that individual person that tends to want to do this.

And um, I'm on a creativity course at the moment, which is bizarre. Which is a wonderful course with about 60 people internationally. And, and most of it work is done early morning cuz people are in different time zones. Yeah. But a lot of what I'm hearing in the creativity course is just the same as I think being an entrepreneur.

Um, you know, these amazing people are making, golden kangaroos in Australia and, you know, our standup comics in New York and, and, and writers and all sorts of things. Yeah. But actually the process is very similar, which is, um, rooted in confidence that you are okay despite, and, and, and most people will chip away to make you fit a shape, fit a box, and it's, I think as an entrepreneur, it's very difficult to accept there is a box. Yeah. You, you don't, you don't think, it's not that you're being Posey. I reverse that comment. And it's more, you just don't think in terms of boxes, you don't think in terms of being been contained, there's always possibility.

Um, there's always a chance to make something different somewhere. And so you, you sort of, you sort of wrestle with that hope, um, and, and you have to actually learn quite a lot of resilience to deal with the naysayers, the structurers, and then you need to learn to work with them and act because you can't do it all.

I mean, that's the other classic thing I think, um, you can see in entrepreneurism is, is this naivity to believe that because it's your idea, you should be able to deliver everything. Yeah. And, and, and I think that is small thinking and usually doomed to failure quite quickly.

Matt Edmundson: It, I, I get that because yeah, I, I do get that, um, that, that sort of thinking which says, you know what?

I have this idea. I know what I'm doing, therefore I'm gonna go ahead and do it. And actually part of the. Part of the thing that I've had to learn over the years is actually letting go of that and letting people loose and, and bringing other people in and, and helping champion their cause, you know? And that's not easy to do.

Uh, no. I, I, I don't think it's particularly easy to do. I think part of it is ego. Um, part of it is, Um, actually at this particular point in time, I think I could probably do a better job, and so it's easier for me to do it than it is to let you loose, you know, and train you and go through all that pain. Um, there are lots of reasons aren't there?

And it's, it's a really interesting one, have you had to wrestle with that yourself as through these sort of 40 years?

Simon O' Shaughnessy: I, I, I was sort of thinking again, you know, for this podcast about my early life and I think you're so um, blasé, and unconnected actually, if you know, seriously, I think though I was certainly so unconnected, I think I knew I had this sense.

I think this is the other strange thing about being an entrepreneur. You, you, your core senses are probably intuitive. Yeah. You know, you, you, you've probably got a skill set somewhere. You know, mine was sciences and, and, and understanding holistic principles. You know, actually that that living things didn't actually work sequentially.

So I think my basis underneath it was this sort of belief anyway, that things would evolve, which is probably quite helpful, um, to being an entrepreneur. So I don't think, I don't think I fought with it. I think I fought with it more later in life. I, a very good friend of mine, I just got this recent gig to, to help sort out quite a complicated medical center that's falling apart.

And when I was talking to one of my best friends, she said to me, said, Just a question. She said, have you got anyone to sort the detail out for you? And, and I thought, I thought, bless her. She knows me so well. Mm-hmm. That actually, you know, uh, detail. Oh, right. Yeah. What's that? ? What's that? You know, uh, I mean, I mean, I can read the spreadsheet. I can read a profit loss. You know I know, I. can But, but am I interested? Not really. No, not.

Matt Edmundson: Does it drive you No Not really.

Simon O' Shaughnessy: No. Not really. Um, I think one of the most helpful things I did, and I wish I'd done it many years younger, was actually really good personality profile. Um, when I, when I did, I did an H B D I one.

Nice cuz it's got colors and it got shapes. It seems always helps. Always helps. Yes. Not a lot of words, you know. It was, it was actually quite helpful. And, um, when, when I did that about, I think about 2002, 2003 and, um, my profile was so, um, empathetic, creative. Yeah. And so processed and detailed and analytical.

Um, I mean the, the, the examiner, the profiler only said one thing to me. He said, look at that. He said, that's world class. Do more. Yeah. And I think that was the most powerful thing I've ever heard. Do more, it almost gave me permission. Yeah. You know, to sort of be myself. Yeah. But equally, I showed it to my daughter who, who, who has got psychology, and she looked at it and went, oh dad, dad, you just don't care. Do you?

This was the other side of, yeah, she was laughing too. Um, which I suppose if I tumble forward here with you, Matt, that goes on to having the right people with you. Yeah. You know, this is simple. Learning curve is to understand, as an entrepreneur, you are not a superhero. Mm-hmm, you have got a special set of skills which will take you somewhere in life, but you, blimming will need the rest of the people around you to make something of it.

Yeah. And I think that profiling, I mean, if I'd seen that. Before I started dentistry, I wouldn't have been the dentist.

Matt Edmundson: Would you have done that? I was gonna say, you wouldn't have gone. There's just, there' just not.

Simon O' Shaughnessy: No. I'd be like, well, Matt, what? What sort of color teeth would you like to do? ? That would, that would look great.

Matt Edmundson: Do you wanna keep your teeth in your mouth? I don't know. Do you wanna move them out? They don't need to be there if you don't want them.

Simon O' Shaughnessy: There are, there are other concepts and possibilities, you know, I mean, it's not the sort of person you wanna see as a dentist, is it? Yeah. Or you know, or bless the people I deal with mostly now the doctors, I mean amazing people that have a skill that actually works through process and analysis and logic.

And hasn't, you know, enough empathy to be with you, but not to be lost. And then actually creates, you know, in youthis is the journey we go on. I mean, that's what you want. Yeah. When you see that sort of person. Yeah. Um, it's unlikely you'll get that with most entrepreneurs. Um, they, they might think by the way that they can do it all, you know, they have this because you sort of can adapt.

Yeah. Like I know I. You know, if you force me to look at an Excel spreadsheet or, or do something in numbers or something like that. Yes, no, I can do it. Do I enjoy it? No. Am I really good at it? No. No. I mean, there are people I usually try and have around me that just can do it and love it. Yeah. And that makes like the better.

So perhaps that's the other thing, team, finding a team and actually being able to collaborate, I think are essential features of being an entrepreneur.

Matt Edmundson: Yeah, I couldn't agree more. And I think the, the longer I do this game, the more I realize actually as an entrepreneur, um, my skills need to lie in one, having.

It's not necessarily a clear vision, but at least some understanding of where I want to go to, of what the future looks like, and, and galvanizing a team to join me on that journey. And in some respects, to take me on that journey, uh, and, and focusing more and more on team and less and less on, um, you know, the other stuff seems to pay dividends, but I, I didn't know that 20 years ago.

Simon O' Shaughnessy: No, I don't think being an entrepreneur, entrepreneur is an individualistic sport. Mm. I mean, I, I, I play rugby, but I wasn't interested in, ended up on the squash court because I liked it because it was me, you know? So there was always that there, there is this strong individualistic drive going on in the entrepreneur, but absolute folly, if you think that will take you consistently on through the way you will crash and burn somewhere.

Because actually the pressure, I think the pressure is quite high. Being an entrepreneur, I think, I think your resilience has to be very good, and I think you have to know yourself very well.

Matt Edmundson: Um, what do you, um, what do you mean when you use this word resilience a couple of times now. What do you, what do you understand by that word?

Simon O' Shaughnessy: Mm. I I think there's a classic definition, isn't it? That, that you, you overcome the, the, the turbulence of the day, you know? , but I, I, I think it's deeper than that. I think it starts in a, in a core sense of knowing mm-hmm. And, and that's not something that happens over, you know, you can't read a book on resilience and go resilience, now I'm resilient, you know, um, you can get some ideas, but.

Resilience is found, um, under pressure, isn't it? You know, pressure comes and you find, um, your resilience. I, I'm watching at the moment. Um, Pat's got me to watch, uh, limitless.

Matt Edmundson: Oh, with Chris Hemsworth. I was literally watching that earlier on. Yeah, yeah, yeah. I was watching the fasting one.

Simon O' Shaughnessy: I, I, I don't normally go for programs like that, but I start watching and I thought.

Oh, this is interesting. This is, this is a man teaching himself resilience. Mm-hmm. You know, I mean, just watched him do an Arctic swim. Yeah. Where, you know, he had to halfway through cuz he was dying halfway through. That was, that was the death spin in the water. Mm-hmm. Um, he had to put his mind back in to the frame of what he was told by the expert.

And that's, that's resilience because he actually adopted a different line of thinking that actually allowed him to move forward past where he was into, into success in this case. So I think, I think resilience sort of looks like that to me. Um, I think, I think for me it also is, is being able to deal with volume.

I mean, at the moment, being a, if you like an administrative manager, leader of a practice, um, or practice, you get bombarded. Um, you know, no one comes and goes, how are you today? They're not, they're not interested who you are. It's like, solve my problems. Yeah, fix, fix this for me now. And so you'll literally get five people in the row asking for something to be fixed. Yeah.

You know, so I think you've got to be able to cope with that as an entrepreneur as well. You know, there are multiple parts moving. Um, some, some of them you're not quite sure why they're moving, but it seems a good idea, you know, I'm sure it'll end up somewhere, you know?

Yeah. Um, which is back to my holistic idea that actually you've gotta allow this, this ambiguity going on. If, if something's gonna be created, it won't all add up, you know? Um, and that there'll be stuff happening and you've gotta have a mind, a resilience and mind that thats that. Yeah. And that, that's not, that's not true for everyone.

Some people will find it really annoying. Yeah. You know, I'm thinking a person will go, well, let's fix that and then let's fix this and let's fix that. Um, I mean, the most linear I've ever been. You know, because if I had my desk when we worked together, you know, I had one pile over here and that pile would end up over here.

So I knew I'd done that pile of whatever it was. I mean, that was me attempting to actually be methodical and linear cuz I didn't wanna upset the people around me. and things were gonna get progressed in the time scale that they need. Yeah. But, but my mind isn't like that. Um, my, my thinking process isn't like that.

My, and I, I have a tolerance for ambiguity. Mm-hmm. , which allows me to have multiple things just there and, and I'm not too bothered about it because eventually something will come forward and fit.

Matt Edmundson: Do you, um, do you find then with that, cuz I, I get what you mean When you walk into the office and everyone says, right, here's my problem.

I need a solution for this, this, this, and this. And you're like, well, I, whoa, whoa, steady on Tiger. And, um, I remember, uh, a couple of months ago, you remember this story. We, um, Sharon had a breast cancer scan and um, I remember. This was, it was quite an interesting time for us, obviously, uh, as a husband and a wife dealing with this concept.

Uh, the first time we had to deal with it. And what was interesting to me was, it was really the first time in a while that I'd noticed that the first thing people do when they see you is go, right how, how I need something from you, you, and try and suck something out of you. And at that particular point in time, I just needed someone to put their, their hand up and go, Matt, how are you doing?

Do you know what I mean? And it was that kind of, and it, and it felt in some respects, a little bit isolated and a little bit lonely. But fortunately I have people that I can talk to. We chat regularly. You know, I've got, uh, the good friend Tony and, and stuff over here that I chat to. And so I, it just, it, it was a really interesting point for me to notice that actually when you are a leader.

When you are the entrepreneur, when you are the person at the top of the pyramid, maybe at the bottom of the pyramid, if we invert it, maybe that's a conversation for another day. Um, but it's, uh, wherever you are in the hierarchy, it's very difficult. I think for those that you lead to ask you how you are doing and for you to be vulnerable and say, oh, this is how I'm doing.

Right. I dunno if you have found that, um, in your entrepreneurial walk. And so if so, how have you built this resilience? Have you had people to talk to?

Simon O' Shaughnessy: Hmm. I was actually in the back of my mind thinking about leadership, you know, and I think, I think this is probably where I'm going at the moment with this, to answer your question, um, I I think part of being an entrepreneur is learning to be a leader.

Mm. And a leader is, is, is not the old idea of a leader that is untouchable and that has got all the answers. Um, it's, it's actually someone that works or is prepared to work in the front line, um, that understands what the real problems are and, and has enough capacity to actually take on other people and other people's problems.

But somewhere in that, for me anyway, there is the spark and the joy, you know? So, I mean, I had a heavy day yesterday with all sorts of stuff happening, but the joy was in two or three distinct moments, which, which could have gone pear shaped, but actually ended up, you know, I mean, one delightfully with an older lady was a hug, you know?

And she said at the end of this very difficult conversation, sit off, said, um, What if we could, I wouldn't mind a hug. I mean, I mean, I was already there cause I thought she, she had been brilliant and I thought she had cut with a really difficult situation. So, so I think for me, I find the sustenance in, in, in people.

I mean, my core values are, are change, creativity and people. Um, and, and I have got a number of people that I will really open up to. Yeah. And have conversations with. Um, you know, as, as a couple, we've always had one couple over years, which were bizarrely now in New Zealand as well. Yeah. Yeah. But I mean, you know, I mean if we wanted to go and see someone, we would go and see them and we perhaps only see them once a year, you know, cuz they live a little way away.

I mean, we're there straight away. Mm-hmm. So I think we've all gotta have that. But I think, I think for me, part of my resilience is day to day enjoyment of people, you know? Um, and, and you go, oh, that was, that was wonderful. We touched, you know, we, we've dealt with something difficult. We've worked through it, we've been human and we've been normal.

And that, that works. I mean, I couldn't be an entrepreneur that was just locked up in a room with a computer. I, I just go nuts. Um, the new entrepreneur. Yeah. Yeah. As, as, as you know, up north and you know, it was quite rural. I dunno why we bought this house. It was rural.

Matt Edmundson: No, stunning. And it was beautiful and the location was phenomenal. I can see why you fell in love with it.

Simon O' Shaughnessy: Yeah, yeah, yeah, yeah. But if you thought about.

Matt Edmundson: It wasn't practical, but yeah. I mean,

Simon O' Shaughnessy: no, not practical at all. But there you go. That's, that's the life of entrepreneurs sometimes. And you'll like that. Let's do that. Let's see what we can create. Um, so lovely. A joy, but also, you know, sheep and cows.

Yeah. No people. Or if you did meet people, people, how are you today? Oh, that's a good idea. Is it, what do you think of this? Not exactly sort of in depth help you solve it. Yeah. And after, after two or three days, I mean, Patty used to look at me and go, go and find some people. Will you?

could, could you, could you go away for a day and go and find some people? You know? Because, because actually that for me is, is the sustenance, you know, that that makes a difference. I think, I think that's why, well, my background is said too is, is is biochemistry and, and organics and things like that. So I think I've always thought holistically and I've always thought there, there has to be human value somewhere.

Yeah. For me, anything I create, you know, it has to create change and you know, it has to be something that someone goes, wow, look, I want to do that. But it's, it's that sort. Part of it that becomes interesting. Um, of course once that happens on board and

Matt Edmundson: we need the next thing. But how did you, you see, it is interesting you say that, right? And you talk about it has to be this and it has to be that for me to, to be interested. And then that once it's done its point. I don't, you didn't start off your entrepreneurial journey, knowing that, I'm assuming, and it took a little bit of space and time to work that out.

So how did you, how did you, I guess, in some respects, start to understand that, how did you figure out your core values, and this is what made you tick, you know, what was that journey like?

Simon O' Shaughnessy: Mm-hmm. , I, I had a couple of people to help me. One, one was actually a very unusual man. Um, was semiotic specialist.

Mm-hmm. that, that's the person that creates the signs and ambience in inside a shop. Mm-hmm. . So when you walk into an Apple shop, you know it's an apple shop because everything is set out and engineered for the interactions that they want in that shop. So it's very cleverly designed and, and we went off for a period of time and we thought, well, can you do that to people?

Can you actually find the, the buttons, the things that are important that, that, if you will, their brand I suppose. Um, cuz we do have a brand, um, quite distinctly. And actually to, um, enjoy that brand is I think part of being resilient as an entrepreneur Um, so you always, you always take the Mickey outta me, you know, I'm always wearing Ted Baker, you know, I mean, you could probably tell me the brand of shoes I'm wearing, don't say it, you know, and things like that right now because, you know mm-hmm. that there are certain things that I do.

And it's, it's not, it's not Posey. It's actually part of me to be and delineated and it actually stops thinking about it again. You know? Yeah. Because I need, here's the thought. I think as an entrepreneur you need the stability of some sort of structure. I think it has to be certain people.

I think it's certain ways of living. I think it's even the way you wake up and what you do in the morning, you know the way you take some exercise. Yeah. I think you've got to have some sort of substructure there. Yeah. Because after that, everything is chaos, frankly. And that actually is fine, because that is where you find the possibilities.

Now, I didn't know any of that. When I started, I mean, I just, just thought, well, that's a good idea. Let's have a go at that. You know, I'm sure that will work. You know, and, and you probably been luckier to get successes rather than failures. Mm-hmm. But then you, and again, you deliver a real dozo, you know, you go well, looks nice.

It has the framework that could have worked. Yeah. You know, and there's probably a lot of you in it, but you go, yeah, but no. No, no, no one's interested. You know, and then you go, well, okay, that's fine. It's not a big problem and you move on. Um, going back, I think to what you asked a little bit clearer, did I know there was this sort of churn Yes. Going on?

No. No. It, it's, I'm very lucky to be married to a woman that copes with it and actually hasn't got a prop. She actually sees it as excitement as adventure. You know, so, so, you know, we've been lived in so many different places, so many different houses, and we've, we've made decisions. You know, you sit in bed at night and you, you still say, I've been thinking about New Zealand.

Hmm. I've been thinking about New Zealand too, you know, and really you're halfway down the flight path. Yeah. To leaving. Yeah. You know, cuz it was already there. But I think you've gotta be very lucky to be with someone like that. I mean, I remember when we came to live to Liverpool. That literally what bed time conversation and, and and, and I said, look, I've been thinking about this lot.

What do you think? And, and, and she just burst into tears. And she said, I've been thinking about it too. You know, and that it was like, I didn't want to think about it, but I have been thinking about it. And actually I know that, you know that, I know that we should come. Yeah, it will be a major shift. We'll leave our business behind, which is not such a clever thing to do when you've got shops and things like that, you go, let's move 172 miles away.

Matt Edmundson: Yeah, that it'll be fine. That work before the internet. Yeah, before mobile phones. It'll be fine.

Simon O' Shaughnessy: Yes. Yes. The card index will still work fine. I'm sure

I think we had a fax machine. We did have a fax machine shortly afterwards. Yeah.

Matt Edmundson: That was, that was a, I remember walking into your house actually, um, uh, the first time and, and seeing the fax machine and going, ooh, they've got a fax machine.

Simon O' Shaughnessy: Shining. And the buttons go do do do. We really liked the buttons.

Matt Edmundson: You know what, half the audience listening this podcast are going bloody hell's a fax machine?

Simon O' Shaughnessy: I tell you someone that still has faxes. Medical practices.

Matt Edmundson: Really? Oh yeah, they do. Yeah.

Simon O' Shaughnessy: Stunningly, when I walked into this medical practice, if you pre covid, there were these great, chunky, expensive fax machines and it's because they thought they were the only secure way to send information, so they sent it down fax line.

I mean that, that's, that's all changed now cuz we don't want paper, you know, we don't want to touch things. We do things electronically, but, they didn't want to change. It's fascinating, isn't it? We trust the fax machine. Yeah. Interesting. Right?

Matt Edmundson: Yeah. Really interesting. So you've, you went on this journey then of figuring out your core values.

You worked with this guy, um, where you, you sort of did this, can we figure out this with, with people? What were some of the things that you discovered in that process?

Simon O' Shaughnessy: I think when we say core values, I think these are, Um, parts of you that you, you end up going, but it, but it is, it, it's important, you know, if you have a discussion with someone and you get them to a point of identifying a, a value, a true core value, it, you cannot in the end explain why.

It just, it, it's, and I think, I think that cuz we have lots of values, don't we? And our values almost change. When we do, when we interact in different ways, you know, but core values are, are like the pillars of your personality. And, you know, I've walked outta jobs literally because I can't be creative and it's just, I'm, I'm sorry, I can't do anymore.

I can't be creative. I need to leave. And I, I usually, I usually these days, program that in advance. Yeah. To give them more. Learn that. Yeah. Yeah. I'm about to tell this latest group that, you know, I won't last much past July. Mm-hmm. Which would be a shock because you know, the contracts for a certain period of time, but I, I know past July I would've got through what I can do.

Mm-hmm. And actually I need to hand the baton on. So, so I think, I think discovering your core values and there's lot, I mean, there's lots of processes. People can look it up on the internet. You can go through things, you can choose words, you know, the, the systems. But I think to, to get to an understanding of, of where your meaning is.

Yeah. These are making parts of you. And, and then to notice when things go wrong. Cuz one way to really see a core value is to, is to see when actually it's impinged. Yeah. You know, so, so if you, I eat creativity I've just told you about, you know, I've got to go. Why? Can't make stuff any longer. Yeah. You know, or I can't change anything anymore.

I've changed as much as I can. Mm-hmm. And I think I begin to know when I should stop changing things for the sake of it. Yeah. Yeah. Because you can go, you know, I go now actually that's enough. Yeah. You know, I need, need to hand over to someone else or, um, you know, perhaps, perhaps the people element dies to a certain extent in the sense that you, um, you can never quite get any further with, with these people. You've done an exchange in honor with everyone, but actually get to a point going, I, I I can't do anymore. You know, that there's no more spark. Um, these, these, these are quite hard things cause it sounds like you can be quite callous and I'm not callous at all, but you do get to points.

I found it particularly in coaching. Um, you know, I coached a lot of people. I think for some years I was coaching somewhere around 35 to 40 people a month, you know, for two hour sessions. So it was pretty intense. It's pretty intense. Yeah. One to ones with people. Um, and these were all C-suite people, so you know, you know, some big CEOs and also a lot of sort of number two, general manager.

stunning people. I mean, I was just in awe of some of the ways they ran their business. I had so much I could learn, but every now and again, you know, you started engaging with someone and after about four or five sessions you thought, no, I can't do anything here. Mm-hmm. That the, the, the fit is not for me.

Mm-hmm. , um, you know, they're great. They need to go off on their own, but, but I need to get out of this gig. Mm. And, and. I'm fairly clear now about that as well. Um, so people are essential, like we've talked about. Mm. I understand as an entrepreneur, I cannot do it by myself. Mm-hmm. but I have to lead because that's part of being an entrepreneur.

Yeah. Um, I have to learn to delegate and I absolutely need and thrive off of people. Mm-hmm. . But there's also a point where for your own self sake, This core, which is where everything is built upon. You've got to move on. Yeah. Um, and, and, um, you don't do it callously. You do it graciously. Um, but it's actually essential.

Matt Edmundson: Um, that's really interesting. Yeah. So for you then, It sounds like one of the things that you would, one of the things that's important to you to fill your tank is just being around people. People sort of fill your tank, right? That's how you sort of recharge your batteries. Yes. Um, and obviously you've, you've had challenges to overcome.

You've had to build resilience over the last however many years, 40 odd years in all the various different sectors. Understanding your core values and understanding how to be resilient is important in that section. So where do you see tomorrow. Where do you see the future going for you, uh, in all of this?

Simon O' Shaughnessy: Well, I'm getting older and, um, I think, I think I realize some of the things that I used to do. It just takes a little bit more effort every time. Um, um, I, I, I think I love the stimulation but you, you get to a point, you have to start thinking about what else is possible that doesn't require perhaps, um, so much face to face.

Yeah. So much intensity. So, so at the moment, I, I've got, I mean the reason I'm on this creativity course with these wonderful people internationally was, it was a challenge, like a judge. Something I thought was potentially a future for me. Um, It's something I haven't really experienced before. Yeah. I mean, writing, writing a book, creating a journal, um, you know, finding, if you will, products that still will go out into the world to create change and possibilities and, and allow, allow other people to do their own thinking, which is, which is for me, essential.

Yeah. You know, as part of success. If I, if you said to me, what's, what is success? It's seeing someone else do what they can do, which will be different, not necessarily better, but just different from me and I find that quite exciting. Yeah. So I'm, the future for me at the moment, I'm becoming quite conscious about, you know, I shouldn't be up at six every morning in next few years, you know, over 70.

I might want to be a little bit more rested in the morning, take the dog for a walk, enjoy breakfast with the wife. Yeah. Things like that, you know, so I probably need to develop another career and, and, and so I will.

Matt Edmundson: Um, does that scare you cause you, you, like you say, you're in your seventies or you will be, you're, you're approaching seventies now, aren't you?

You're in that decade. Traditionally people have gone, wow, I'm gonna go play golf for the rest of the, you know, not to disparage those of listeners who have retired. Um, I guess I can never associate the word retirement with Simon O' Shaughnessy. I just can't do it. So it would not surprise me that you would reinvent your career or yourself in your seventies.

And you'll probably do it with gusto and Pat will be cheering you on and joining in. No, like, no doubt like she normally is. But does that scare you? Does that, um, or does that thrill you, that concept?

Simon O' Shaughnessy: Both. Um, Because I think, I think if you, I think if you push into anything mm-hmm. You know, it's, it's got to come with, um, the same things that we've just talked about.

I mean, it, it is, it is wash and repeat. You know, I, it's, um, anything worth doing actually requires effort. Someone we both know who was very successful in worldly sense when he was asked, you know, would you, would you do it all over again? Said, oh no, too hard. And this was towards the end of his life. And I thought that was a very telling phrase.

Yeah. You know, no too hard, I think. I think you realize how much effort you have to put in. Mm-hmm. Can you stop? No ? Not really. No. Not really, because it's, it's, it's how you're wired. Mm. You know, um,

Matt Edmundson: I was gonna say, would you actually want to stop? I don't think you would. Would you?

Simon O' Shaughnessy: No. No, not really. No. I, I, I mean, you know, on my, my table at the moment here, there's a whole variety of stimuli, notebooks, you know, stuff going on because there are, there are ideas and projects.

you know, somewhere in all this. And I mean, I, I like it. I want to play with all this stuff. I've just gotta learn to play differently. Yeah. And, and I think hopefully, hopefully that's wisdom. Now, I don't know.

Matt Edmundson: I don't, but did you not find that like I'm, I'm, I'm, I'm approaching the decade of the fifties now.

Um, and I think my approach to life as I approach 50 is quite different to my life when I approached 40. Uh, and I think that's just part of aging, isn't it? Or just part of wisdom, I suppose. And learning a little bit about life as you go along is like, how are you gonna approach it? So, right, I've got to the stage of the podcast where I'm gonna introduce a new segment.

I mentioned to you that you are in fact, the Guinea pig. Uh, we have a block of questions here, right? And, um, I'm gonna tell you, you're gonna say stop. Uh, and I'm gonna, I'm gonna stop wherever you tell me to, and I'm gonna, whatever questions on the card we're gonna ask, I think it's quite fun. So, uh, go for it.

Simon O' Shaughnessy: Stop.

Matt Edmundson: Stop right there. Okay. This is an interesting question, so I'll hold it up to the camera. If you're watching it on YouTube and I'll read it out loud. It says, when do you feel lonely? Gosh.

That's a great question, isn't it?

Simon O' Shaughnessy: Yeah. Okay. I could, I could answer that superficially, which would be in line with the interview and say, obviously without people, and I've told you stories. Yeah, yeah. If I answered it honestly. Mm-hmm, and this, this, this is, this is I think one of the problems of being an entrepreneur. The answer is always. Yeah. And I think, I think for me, anyway.

Holding on to everything that's going on in the end creates a little bit of separation and, and I'm, I'm aware of it. It's not that I particularly want it or don't want it, it is just there, um, it's a bit like. You know, if you talk to a lot of creative people and they're being really honest, there will be a moment where they admit to the old black dog you know depression?

Yeah. Mm-hmm. Is some, is some, they, they're probably controlling it really well. Yeah. You know, but, but it, it is there for a creative in my opinion. You know?

Matt Edmundson: Is that the, the, the balance, is that the opposite? The ying and the yang, if you are creative, there's, there's the depression side of that as well. It seems, out of all the creative people I know, I'd probably say that's the one thing they suffer with concurrently.

It's like there's a tension. I don't know if that's true of everybody, but I'm, I'm just curious to know what you think.

Simon O' Shaughnessy: What, what is, do they suffer with it or is it part of the package? I mean, and, and I think loneliness is, I think somewhere, part of the package for a lot of entrepreneurial type brain sets, creatives, because actually you, you need that experience.

You know, you need that understanding and breadth of empathy. To do a lot of the stuff that you do. Yeah, I, I, I had, I had a semi argument with a psychologist on this one once, and, and she was wonderful lady, really enjoyed talking with her. And, and I said on, you know, the, the black dog, you know, it sits quietly in the corner most of the time.

And she said to me, so, so what would it be like if we removed the black dog? And I was gonna fight her. I was not letting you take that black dog away. You will not take this away. It's, hold on. It's my black dog. Yes. You know, and, and I could see this was a, this was a non sequitur for her. This was not acceptable, but I'm going, no, no, no, no, no, no.

I, I can live with that as a creative. Primarily my, my, my brain works creatively. I, I can live with it. I know where it is, and actually pretty much now I can control it, you know? Um, I think the same is true for the loneliness. It's it's life spirit almost, that you've got to learn to recognize when it would be impairing and deal with it.

Um, but I think you live with it. Or I do in that sort of sense. Um, and, and no amount of prodding. I mean, if you prod me, you'll just annoy me anyway, you know? Well, come on. You know, get, get with it, you know, join the party. Well, I don't want to.Thanks. Yeah, I'm quite happy. Yeah, so I, I think, I think my honest answer, great question.

Yeah, I could have passed. Really, couldn't I?

Matt Edmundson: Yeah. Yeah. It would've been very dull though, had you have done, um, but no, I, I get that. I get, there's when I think if you are in some form of leadership entrepreneurship where, you know, some kind of leadership, it can easily be a lonely place. And that's why I go back to.

When Sharon had the breast cancer scare, I was very grateful for the people around me that actually I could talk to and, and confide with because those, um, those, everybody else didn't know what to do with the news. Do you know what I mean? It, it wasn't, people weren't being, um, difficult or rude or any, they just didn't know what to do with it.

Right. Um, but I'm, I'm grateful for the people around me that actually just put their arm around me and just went, man, that's crap. Let's walk through this. Right. And I think, um, so yes, I get actually leadership and loneliness I think is synonymous. Uh, and I, I think it's, um, it's a tricky situation if you're a leader.

So you do need to create that community, right?

Simon O' Shaughnessy: When, when we, when I was running CEO groups, they, they, I mean, wonderful guys, individualistic, strong personalities. I mean, you know, they'd eat you life in some ways, you know, but, but they also said, said, do you think we ought have a T-shirt for our group? I said, what's that?

They said, CEOs are humans too.

you know? Yeah. And, and, and I understand. That's it. It's the same thing. It's the same. Yeah. You know, there are very few people we trust ourselves to talk with, but I, I desperately want to talk with you because you are my friends. Yeah. And I think, I think that's, that's the essential little link because most of it is not, um, It is not the team as far as you are concerned, it's leading the team.

It's quite different.

Yeah. Yeah. Brilliant. Good question. Thank you.

Matt Edmundson: Yeah, very good question. Uh, so don't thank me. Thank the box of a hundred questions. We like the box. Woo. As you know, this show right is sponsored by Aurion Media, which specializes in helping good folks like yourself set up and run their own podcast.

So I'm curious, right? Let's assume Simon has the O' Shaughnessy podcast, the Catalyze podcast. Who is on your dream list of guests? Who's your, who would you really love to have on the show to interview and why?

Simon O' Shaughnessy: I'll be a bit iconic and New Zealandish here. Mm-hmm. um, during the first covid about where things were really hitting the fan. Out the blue, and you guys won't know him, but there's, there's a Dr. Ashley Bloomfield in New Zealand who the director general of health, and this is public servant who stood up and actually became the face of, you know, the covid response in New Zealand.

Mm-hmm. . Mm-hmm.. Um, he was totally brilliant. ,um, in fact, I think at the end of the day there were Ashley mugs, Ashley tshirt. Oh, wow. You know, we, we love Ashley. I mean, you know, he just went, he went over in the nation so well that people could trust. Um, we were lucky enough cuz we were doing like a team session every other day in the practice, a big practice, 70, 80 people.

And we just took a punt and rang him up and talked to his secretary and said, do you think Ashley would come onto our, our teams meeting in the morning? And he said yes. Oh wow. So the director General of Health ends up on a little private channel talking to my group. You know, one morning in the middle of our huddle an he was just, he was just brilliant and we were all in awe.

In fact, one of the doctors said to me after, said, I didn't hear a word he said, I was just so overwhelmed. Yeah. But I mean, and I wished I'd asked him more questions. Mm-hmm. you know, the things that interested me was all the things we've talked about, but here's a man, not like, Who does not think like me, who has a very different background.

I mean, to me How fascinating. How totally fascinating. That's really interesting. Someone like that, you know? So, um, Ashley.

Matt Edmundson: Fantastic. Well, when you record the episode, I'd love to hear it. That'd be brilliant. Uh, Simon, listen, it's very rare I call you Simon. I appreciate, uh, but I thought I'd do that for the podcast Chief.

It's been brilliant to, um, catch up and have a conversation with you and record it. Uh, cuz this is normally what our conversations are like, uh, and we just, we just riff off of each other, which is great. Um, if people want to connect with you, if they want reach out to you, what's the best way for them to do that?

Simon O' Shaughnessy: Probably LinkedIn or by my email. Yeah.

Matt Edmundson: Okay. Uh, and what's your email?

Simon O' Shaughnessy:

Matt Edmundson: And of course you can search for Simon O' Shaughnessy on LinkedIn. And uh, you are also there, uh, quite active on LinkedIn, or at least you used to be. Do you still do the LinkedIn thing?

Simon O' Shaughnessy: I think I, I've had a bit of a pause on LinkedIn over the last, you know, few weeks because of this new job.

Just suck the life right outta you. And, um, and stupidly, I thought, oh, hold on, let me do this creativity course online as well. , which, which, which requires you to blog every day. Oh wow. To do, you know, those three or four quite chunky questions a week as well. Mm-hmm. So that's sucked out my energy. I haven't been able to divert it into LinkedIn for a while, but fair enough. But we can.

Matt Edmundson: Yeah, no, fair enough. Well, it's been brilliant. Chief, thank you so much for joining me on the podcast. Honestly, it's been an absolute treat. Really, really appreciate it and no doubt we will have you back on again at some point, talk about all kinds of stuff, something. Yes. Something I've no doubt.

Uh, so that's it from Simon. Thank you for joining me. We will link to Simon's info in the show notes, which you can get for free along with the transcript, uh, and all that kind of stuff at or it comes auto magically to your inbox. Uh, if. Automagically, if you're signed up to the newsletter.

So big shout out to today's show sponsor. Just like, just like, just like that. Just like that.

A big shout out to today's show sponsor, uh, Aurion Media. If you are wondering if podcasting is a good marketing strategy for your business, do connect with them at That's We will, of course, link to them, uh, on the Push to Be More website, um, and it will also be in the newsletter, which is automagically coming to you if you are signed up.

Be sure to follow Push To Be More wherever you get your podcast from because we've got some great conversations lined up and we don't want you to miss any of them. And here's my favorite part, in case no one's told you yet today, dear, wonderful listener, uh, you are awesome. Yes you are.

It's just a burden you have got to bear. Simon has to bear it. I have to bear it. It's just the way we've been made. Uh, Push To Be More is produced by Aurion media. You can find our entire archive of episodes on your favorite podcast app. The team that makes this show possible is Sadaf Beynon, Josh Catchpole, Estella Robin and Tim Johnson.

Our theme music was written by my amazing son, Josh Edmundson. And as I mentioned, if you would like to read the transcripts and show notes, head to the website,, where you can also sign up for the automagic weekly newsletter and get all of this good stuff direct to your inbox, totally free.

That's it from me. That's it from Simon. Thank you for joining us. Have a fantastic week. Uh, I'll see you next time. Bye for now.