Simon Jackson launched the superb Moors One Hundred bikepacking event in North Yorkshire. He guided me around some of his favourite trails on a glorious day of summer heatwave. Simon has a normal job and the usual commitments of raising a family. So he has to work hard to squeeze in bursts of adventure and spending time in the wild places that he loves. I loved the story he told me about setting himself the Strava challenge of cycling every single street in his hometown.

Simon is an evangelist for the North Yorkshire Moors and I could see why. We cycled over open moorland, through forests, and sweeping singletrack. It was a hell of a ride. Best of all, given that it was blazing hot, was that Simon planned our ride via a pub lunch and a return ticket on the famous Goathland steam train.

Listen on Apple Podcasts, Spotify, Stitcher, TuneIn ("Alexa, please play the Living Adventurously podcast") or on your favourite podcast platform such as Overcast, Google Podcasts, Pocket Casts, Breaker, Soundcloud, Castbox, Castro.

Your very own outdoor experiences are waiting for you. Go explore more with komoot. Use the voucher code ADVENTUROUS to claim your free region maps bundle.

The personalised planning and navigation tools ensure you plan the adventure that’s perfect for you. Komoot is Europe’s number 1 outdoor app, with route planning and navigation functionality, and strong community-driven inspirational features in the form of recommended Highlights and inspirational route Collections. It is used by nearly 10 million adventurers worldwide. Komoot is becoming the app of choice for cyclists and hikers the world over, with rapid community growth in the UK, the US and other parts of Europe.
You can see my ride’s route on komoot here.

Alastair Humphreys
Right. I'm sitting in a camper van. Very, very sweaty with Simon. Hello, Simon. Hello. Welcome to the podcast. Nice to be here. Are you in? Are you a veteran of lots of podcast?

Simon
No, this is my first podcast experience. Excellent.

Alastair Humphreys
That's how we like it. And what's your day job?

Simon
I have a small garage. Nothing terribly interesting.

Alastair Humphreys
What do you do then to try and fit adventure into your

Simon
normal life, try not to be at work. And that's, that's the key. Especially midweek because they're the best adventures made week. Yeah, they're the best ones they feel and feel a lot more special. Because you should be at work. You know, you shouldn't be sat behind your desk, you shouldn't be doing something tedious and mundane. You know, and other people are, and it feels great not to be doing that.

Alastair Humphreys
Okay, so what then is the secret of not being at work in the middle of the week?

Simon
And having good people around you you can rely on a very understanding wife that complains but doesn't really mind in a heart that you are taking a day off to kind of blow off steam?

Alastair Humphreys
how'd you go get your adventure kicks? Would you like doing

Simon
anything you know, it can be something you've seen on TV, something you've read about something you fancy doing something you read in a in a book, something that fits in with that available time that you've got something that's going to be worthwhile when you don't have a lot of spare time when you're working when you've got a family has to be quality notes. You can we just Well, that was all right. Yeah, there's a pressure there to do something. Interesting. You just gotta try and make the most of it. And if you ponder it too much, never gonna do it.

Alastair Humphreys
Yeah, that's very true. So we've just been out for a day out on a few hours out backpacking around North York tomorrow is that's how we got in touch originally, you run the most 100 is

Simon
that we call it last 100. Yeah,

Alastair Humphreys
yeah. Which is a bike packing

Simon
as a bike talking event that runs on the most hundred miles, hence the name over two days. Pretty much doable for anybody of any level on any bike, very sociable. It's great fun, I really enjoy organise it and everybody's who's done it say the vast majority or whether whether you really did or not, but there seems to be a lot of happy faces.

Alastair Humphreys
So I you you've been showing me around some trails day and I really enjoyed this beat North York was a beautiful place to this is beautiful. It really is. And you're clearly a real evangelist and passionate about it. You kept telling me all these facts and figures and interesting stuff about it. So I get the you like it, but why bother? organising an event already busy enough? Why are you organised by you organise the most 100

Simon
I don't know. He got he got the Lake District. He got the Peak District. And it's it's rammed it's really busy. There's a lot of conflict with walkers and mountain bikers these days. Come on North Yorkshire, most as you've seen today, apart from down at the train station, we've seen no deal day, I've seen absolutely no, there's not that conflict. And people that do come to North York tend to head to the trailer centres at Dolby. And don't get me wrong, I love the place. It's great. And I think it's a really, really wonderful place to spend time whether that's walking aside and and I just want to kind of educate people to that. And you know, it's so worthwhile just having someone say, That's brilliant. I'm going to come back here on my kids, I'm going to bring the wife back here on a partner. It just, that's the reason why really, it's just it's just to expand

Alastair Humphreys
on that really? Well, I think it's I think it is an event lots of people enjoy so highly, highly recommended. I am very sweaty right now.

Simon
It's very hot. He has been the hottest day of the Actually, it's been a sticky one.

Alastair Humphreys
But what one of the things I like about being out biking with someone. And actually, it's nice if it's someone you haven't met, it's just nattering away about the world. And I like today your approach to life in the world. So I wondered if you might like to answer some of my questions. These are my These are my big questions for life. I'm looking for answers for you seem like a wise man. From the top. Let's, if you don't answer you have to

Simon
what would you say to someone who told you that your life was becoming less adventurous?

Alastair Humphreys
Know, is your life becoming less adventurous? Or is your Are you on the way?

Simon
I think it ebbs and flows, isn't it, you know, your life changes. circumstances change when you've got children, there are periods in that time where you have a little bit of spare time away haven't. It's something to be mindful of. Quite often, it's something you may not have control over. So it is about grasping those opportunities whenever you can, and really making the most of them and then not letting them

Alastair Humphreys
go by new you're in your 40s Now, are you conscious of trying to

keep up an adventurous life?

Simon
Yeah, cuz as you get older, and I've been mountain biking for 30 years and things ain't as easy as they were. Things don't heal as fast. Knees are getting creaky and going upstairs, you know, that whole thing of Oh, yeah, I could ride across India for one to two. One day, I could make it even right to the shops. So there is that sense of, you know, the bigger things that you've always fancied to do that, you know, as the years go by the small pressures and achieve those things, you know, on the other hand, you see your guys on bikes, and they're still enjoying themselves.

And there's other things walking claiming to be about bikes. It's about having fun and enjoying yourself, isn't it?

Alastair Humphreys
See? You don't have any intention

Simon
to accelerate? governor? No, no way.

Alastair Humphreys
No. Good, right. Next question.

Simon
What are you willing to sacrifice from mission.

And,

again, it's about finding the balance, isn't it?

There's lots of things I'd love to do. I mean, we've discussed family and stuff, as we've been riding along today, I do miss my children and my wife a lot when I go away. So that's like, you've gotten this thing where you really want to go away, you see these, these things, these places you want to go. But on the other hand, you know, sometimes when you go, you're going to be a bit miserable, because you messaged them. So although I want to be adventurous now, great fun. There's gotta be a limit, really.

Alastair Humphreys
So you need you see these ideas of big adventures, but you're not willing to sacrifice time away from your family for that. So

Simon
it's not so much it's not an issue, not conscious. Where the thing is, it's kinda in the, in the heart of it, say, on paper, you think, Oh, well, you know, it's just a few days or a week or something. But you know, it's going to be difficult. So it's not a it's not really a conscious thing. It's not something you really have much saying is it?

Alastair Humphreys
Yet as perfectly valid thing. So in that case, then if you if you're then pausing your ambitions of let's say, I'd know cycling cross India, how do you then scratch the itch, while still fulfilling all the responsibilities in your life? It was

Simon
hard, isn't it, you just gotta,

you just gotta look at things that are attainable, are achievable. And, and find pleasure in that, you know, there's still so many things that we've seen today where you can see, you know, beauty and things are interesting things are, you know, a great bit of trailer, something, you gotta be, you gotta count your blessings, you got to be thankful for some of your doorstep, or what you can achieve in that time scale. Right? somewhere new, right, with someone different, you know, what a great time today.

That's, that's what you gotta do, really, you've got a temperate in a different way.

Alastair Humphreys
And you can't just say, when you're cycling around the North, you must suck out of it as much as you can. Bearing in mind, you say not the cycle across India,

Simon
twice, some guys do. And you know, it's always nice to find a new piece of trail of learn something new or compensation and learn something new. Some of the times you just want to go out and paddle and you just want to enjoy this. You know, just wanna enjoy the scenery. And I don't, I don't think you can do any ride and not take something from it. I mean, it can be a miserable day weather and the chain snaps and the rains howling sideways. But you still take something from that, even if it's a negative

Alastair Humphreys
thing. Or even just the as you said today, just the gratitude of getting back to your van in the end.

Simon
Yes, it's just nice to get back.

Alastair Humphreys
I've often found that that sometimes a day so miserable, that the only good part of it, which is a good part is how grateful you feel to get into bed with your sleeping bag. And just that actually noticing it and remembering to appreciate it. Yeah.

Simon
And you and you adjust what you do going forward, you know, maybe a piece of kit that doesn't work or a piece of trail that was horrendous in the wet, but it was great. Last time you went down in the summer stage. Use it in the summer. Yeah, listen, you've got options. You know, it's not as though you're stuck on a treadmill and do the same thing day in day out. You adjust and you adapt.

Alastair Humphreys
That's very true. And next question. Here we go.

Simon
I don't got my glasses.

Well, you doing at times you feel that you are being a parent?

Alastair Humphreys
Yeah, Woody, what are the what are you doing at the time to nearly got it sorted about

being a

either husband or a dad

Simon
really know, just

Alastair Humphreys
just getting through life and so many challenges these days? It seems to be more and more. But I think there's a difference between the times when you think you're just travelling through the routines of school, do the shopping, take the bins out? And then the time to think yeah, this is this is going good.

Simon
Yeah, you get that. But you still you've still got you still got space in your mind to daydream about things as well. So you might be doing the iron in our cooking results or something like that. But you can while you're doing that you're on a kind of autopilot. So you are thinking about riding that trip across India, right in the middle. So it's been a while since I've been to the Lake District. So you never kind of switched off really a cane if you can do you can, you can be doing one thing in a physical practical sense. And you can be daydreaming about the other thing. But

Alastair Humphreys
yeah, I find interesting say that because I find in my own life that I really when I start doing that, that's when I don't do things well, and I'm trying to dabble with two different things at once is it's one, it's one of the reasons I have my shed to work in Turkey, go to my shed, and write books, and then leave the shed and then I get on with the rest of my life and try. And so I find that to really separate things like this part of my life. Yeah. And this part of my life for the time, so I try and mix them or model them or blend them into good

Simon
kitchens that place with me. When I'm in the kitchen. When I'm cooking something I'm just right. I've done this before. I'm on autopilot. I know I'm doing right that routes that I've got plans and you know, tick tock and I'm working on that in my head and is kind of writing that needs to boil for two minutes, the phone comes out and I'm looking at the map and looking at options and listening. Yeah, that works. Okay, so even though you've you've got the what some people might think as mundane things of the day to day life, it doesn't mean that you can't be thinking about adventure and planning adventure. I think that's the difference. If you keep that adventure mindset, whatever you're doing, whether you're actually physically doing thinking about it, so it's all good.

Alastair Humphreys
So are you thinking about adventure? Quite a lot of your time. So when I eat when you

Simon
Yeah, all the time? Yeah. Yeah. And it's not just a base I think places you could go and places protect the children to and things you can see are something that you've read about that you want to go and see. Or even just reading about things, you know, something new, you've heard you hear a snippet of something, I see an image anything I want to learn about that, you know, so that's an adventure in itself because it leads you from two different avenues as well of learning and knowledge and seeing different things, seeing other people's opinions.

Alastair Humphreys
So do you do you think it's possible to scratch the adventure six, do you think it's possible to live adventurously without

Simon
leaving the house? No, no, let's go. There's got to be a balance and

Alastair Humphreys
there's gotta be a balance.

Simon
You've got to

I think as long as you think of Benji and fit in every spare moment, the camera

doesn't children's

life semester, and he just sat around the house when he could be out doing something. That's the difference. We've all got busy lives. We all have things to do whether we want to do them or not face these challenges when you get them take them.

Because you've been thinking about it for so long. You've already got pretty formed idea. So it's not like oh, what am I going to do myself? It's like, bang don't do it.

Alastair Humphreys
Yeah. And your self confessed? Bit of a struggle obsessive. We have been perhaps at some point.

Getting you miles in

Simon
Yeah, get me miles in Yeah, not be fast, but just Okay.

Alastair Humphreys
Tell me tell me about the time that you rode around your town.

Simon
That was a great afternoon. I suppose. That was an afternoon where I seen the idea in one of your books and of walking around the town. And I came out the house one day I thought I wish I could go today and I've done this. You know, I'm gonna ride around every street in the town. It's far more difficult than you think it is not big town I come from I can't think population off the top my head. It's not it's not big. It's a typical market town. Things don't realise how big these players are. How many little streets and Nick Cole this x and avenues, little nooks and crannies. And you think you're doing a pretty good job of taking them all off you go into one street. And when I when I got home and have a look at the results on Ostrava met such a massive it. There's so much it missed out. So what you've done. There's like a kind of a math puzzle here.

Alastair Humphreys
It's amazing, isn't it? how little we know about where we live?

Simon
Yeah, it was, that was a really cool thing about it. Because it be street that you've driven past every day, or an entrance to something you driven past or a hedge that when you sat down low in your car that because you're on your boat, you could see over it. And there's a there's a house, or something, so many things that didn't know about your hometown. It's just adventure. I went home that night, and I thought was pretty good. I've done like, probably 50 miles or something in this little market. And I'd seen so many things, and I bumped into a couple of people and really nice day. So if that's not adventure. Yeah, I know. It's not climbing to the top of Kilimanjaro or anything that I had a great day.

Alastair Humphreys
Yeah, I agree completely. And do another another count. Yeah.

Simon
Tell me the storey of something. You think

Alastair Humphreys
it's a good thing to learn from them?

And

Simon
then we'll do stuff that would be great.

Alastair Humphreys
At some point. Remember, this is a public podcast.

Simon
Yeah. Yeah. And I mean, I've always tried to be pretty decent. But I mean, you make certain decisions that didn't work out. But I think if you learn from your mistakes, not saying yourself.

Yeah, yeah, it's a tricky one to answer that one. Okay. Good. As long as you as long as you learn from that one, I think.

What will you be able to do in 10 years time? Can you do that he can then so I'm probably hook really big gap jumps on bicycles. As you get older, you get a little bit more cowardly. And the things that I wrote down 10 years ago, that I wouldn't write down now. So in 10 years time, I'm just wondering what that what that that graph, if it's linear, or whether it's the stuff that I will do now will terrify me in five years time? And does

Alastair Humphreys
that affect what you choose to do now?

Simon
Yeah, it does. Yeah. Because there's certain routes that you can do. Not so much in the northeast, most it's all pretty mellow. And there's nothing really scary, but you can go go to certain places, and this was where you need some commitment. You know, breaking down Dolly work waggon pike on the hotel the other week, you know, I was thinking, Man in it, you know, 40 odd years old. And if you come off at this speed onto that surface, it's really going to hurt.

Were a senior. So 20 years ago, you see these skinny kids on YouTube and stuff are in the button jeans, and they have massive accidents, and they get up and it's all high fives and stuff, you know, and it's reverting back that way.

So yeah, there's this thing's I that yeah. So that has a bear and away you go. And we can get off and walk them. But

Alastair Humphreys
you're right that

Simon
Yeah. There's no shame in walking.

Alastair Humphreys
Good. I'm glad to hear that. No, definitely not. Next,

Simon
what he is scared of

running that time.

Running that time?

Definitely. Me too. It's terrifying, isn't it?

Yeah. When did that kick in? as well as

Alastair Humphreys
I thought I had it for most of my adult life. Right. I actually remember

my 25th birthday. I was in Beirut, cycling around the world. And I'm freaking out that day thinking I'm 25 a quarter of a century old. My life must be nearly over to be 25. Yeah. And I was currently at the time of cycling around the world, but I was having the time of my life. But even so I just sense of mortality. Now this is passing by. So I've always had that affliction. And actually, it's, I don't think it's good that it encourages you to get on and do stuff. But if you become a bit obsessed with it, then it's not particularly healthy, I think.

Simon
Yeah, I can imagine if you dwell on it too much. Yeah. Quite. Now that's that's the big fears and time.

Alastair Humphreys
So what have you got to do in that time? Just

Simon
try and make the no grand, massive ambition to do this. There's things I'd love to do and Amir be able to do and the kids are little bit older. Boy, for me is about just grasping them little moments and making the most of what you have got. rather than sort of like painting thought you can do and I'd love to do this. I'd love to do that. Just go for it and what you can and just be conscious that you can't get away with doing this forever.

Alastair Humphreys
Yeah, that's very, very wise. But we're both very hot and sweaty. And I'm quite

Simon
monstrously here

Alastair Humphreys
today. So my final question is what you're gonna have for tea tonight?

Simon
Whoo, good question.

I don't know. I think I'll swear by the allotments my way home and see what looks ready. And in the hundred and 50 yards allotment to the front door, I will have worked out a master plan. And that will be what I'm having fun. Sounds good. Today could be red onion. And Goosby sandwiches, which sounds pretty horrible, doesn't it?

Alastair Humphreys
Yeah. Hope you can do the chip show. Yeah.

Well, thank you for thank you for chatting to me. And thank you again for showing me around and I hope lots of people sign up

Simon
for the more than 100 that would be really nice if you did because you will have a really really nice time. The trails are awesome. Yorkshire is absolutely stunning and the people you will meet really are the best people are really really great people. And you have a right smashing.

Alastair Humphreys
I agree with that. Thank you very much. Thank

Simon
you very much. It's been an absolute pleasure.