A better way to approach scary life choices

Hey everybody, welcome to the OnSchedule CEO Podcast. I'm your host Jonathan Courtney and you know, welcome. If this is your first time listening to this podcast, this is a... unedited it's kind of like a live stream so it doesn't have all the normal stuff podcasts have like uh editing out the bits where i'm just like answering the door if someone delivers a package or uh i don't know

editing bits out where i just don't know what i want to talk about and um yeah otherwise welcome back i'm doing a quick one today um because i've got a lot of stuff coming up this week but there is a topic i wanted to bring into the podcast today and i think it's It's one of these things which I think is actually valuable to know about. Many of you will know that one of my favorite books of all time is called Hell Yeah or No. And occasionally I'll do a whole episode.

on a chapter of that book. And that's what I'm about to do right now, because there is a learning from that book. And this has been a big learning in my life over the last five or six years. And I don't know how I'm going to bring this all together in this episode.

because it's just a lot of it's it's you know i wrote the word nuance in my notes app i was like episode idea nuance um but What I'm trying to get at here, what I want to teach you today using the amazing Derek Sivers LER notebook is something that I think everybody, every human needs to know, but not everybody intuitively does. So what I'm going to do is I'm just going to read the chapter. It's, you know, it's only like one or two. It's probably like a two minute long read. And yeah.

It's funny, I remember back in the old days of this podcast, which is only like two years ago, people would complain that I would just read stuff. But that's what this fucking podcast is about sometimes. So we're going to do that. Okay. You know what I'll do as well? I do have my little music device connected here. So maybe I'll read while attempting to create some music live.

um and it's either going to be terrible or okay but not good this is i'm always trying to recreate the interstellar or my own version of the interstellar sort of main Interstellar song. The movie Interstellar has a great soundtrack, if you don't know that already. I've talked about it multiple times. And whenever I get a new music device, I'm now playing around with the OPXY. I always try to recreate it.

So what you're going to hear me doing here right now is like layering on some bits of music or layering on some instruments and seeing if I can. All right, let's let's where's number. Oh, she had already fucked it. Okay, let's try this. Okay, so I'm gonna read the thing. Let's turn it down a bit.

So people sometimes ask my help in making big decisions. They're usually trying to decide between two options. But that's not a decision. That's a self-created dilemma. You have to remember that there are always more than two options. When someone says, They have only one option. What they're really saying is, I have no choice. And you know that's wrong. At the very least, add do nothing and go insane as options.

When people say they only have two options, it means they got stuck. And once people get two options, they start comparing the pros and cons of those two and forget to think of more. And I think this is kind of back to me. I think that's a very common thing we do, right? We're like, either I do this or I do this. Either I go here or I go there. Either I'm with this person, I'm with that person, whatever. So I think there is a very common thing that we do as people, which is...

We try to, we're like somehow intuitively come down to two things and start comparing them with each other, which is kind of, I don't know, I guess it's just like a thing we do as people. What's interesting here... What I find very interesting about this chapter in the book is just calling out that that is just like a self-created dilemma that doesn't need to exist at all. So...

I'm going to go back to it here again. As an example, a friend was trying to decide whether to stick to his frustrating job or quit or start his own company. So either quit his job. or start his own company and i had some suggestions for him so he here's what derek sivers kind of put together he's like well you could build your new company outside of the work hours

Do this until the income from the new company is 50% of your salary and then quit. That's one option. You could show up to your job, but secretly just work on your own company all day and do this until you get fired. You could also bring your new company idea to your boss and propose it as a division of their company so that you can stay on salary. You can also do neither of these and, you know, quit your job and move to New Zealand to be a tour guide.

After exploring more options, my friend realized that he didn't actually want to start a new business, but he was just avoiding fixing his current situation. So great insights come from opening your mind to many options. brainstorm them all, from hybrids to the ridiculous, takes under an hour, but also always helps my friends feel less stressed, think clearly, and get excited about decisions that used to feel like dilemmas.

And that's the end of that chapter. For me, this is pretty, I mean, I don't know. On the surface, you might be like, yeah, well, I know there's more than two options. But for me, when... what i really learned a lot over the last four years and and there's there's also a lot of people who helped me with this there are people when i need advice i go to people who will

give me basically the the there are a couple of people in my life um when i go to them with a dilemma their answers are never obvious like they're they're I'm expecting them to say this or that or this specific thing and then their answers are always a lot more nuanced than I expected. And it opens me up to the idea that, oh yeah, maybe I've been inventing.

a dilemma here that didn't exist in the first place and the only reason that it's a dilemma is because i've made it a dilemma because i've watched other people live their lives like this where they essentially you know have a decision to make and they're like i need to do this or i need to do this and and it's just a lack of creativity and a you know i guess social conditioning showing us what are the options um and then us

running with those options um i'd love to give you more examples of this but there's some of them are a little bit too personal to share on the podcast for now anyway um but You know, a simple example of that is I'm really sick of this part of the AJ and smart business. You know, the consulting part of the business was really pissing me off the last couple of years.

And my headspace is, I'll shut it down. It's like, shut it down and keep it going. But there is another alternative, which is, why don't I just break? aging smart up into small little companies and I dip in and out of them when I have the energy or excitement or when something fun comes up in those companies and so that's what I did And, you know, this piece of advice came from Blake, one of my mentors, who was just like, yeah, you can just, or one of the other things was like,

Facilitator.com is really stressing me out. Like this is the business that we're trying to get to 10 million, but it's really like a day in, day out, constant, crazy amount of work. And he was like, well, why don't you... not obsessed about getting facilitator.com to 10 million um and you know you have these other parts of the business and these other things you want to explore why don't you check those out and see uh if the whole thing

gets to 10 million instead of obsessing and and putting all of your eggs in that particular basket and uh yeah for me like even the partners business the new age ain't smart partners business um which is now potentially we will end the year with that being the most successful part of all of AJ and smart. You know, that wasn't even an option on my mind this time last year.

There was always this idea like, oh, I don't want to be a marketing agency. That was the other thing, right? Everyone kept suggesting, oh, you guys are so good at funnels. You should. you know, have a funnel business. And I was like, I don't want to have a fucking marketing agency. I either, you know, I either want to make my own products and, you know, sell them. I want to either make my own products and sell them.

Or nothing. It's pretty much like that. But partners is a nuanced and different way of us doing what we are good at without having to be an agency. And it was just not something I'd been thinking about because I just wasn't.

creatively laying out all of the options on the table and thinking about which one to choose. And I think being more comfortable with the idea that when you need to make a decision, there's a lot of options. And sometimes you're not choosing. And it's good to know, like, why am I not choosing or why am I ignoring some options? It could be that you're worried about hurting someone else's feelings. Could be social conditioning. It could be.

that you're worried about having to pursue the thing, you're worried about what success in that thing would look like. But I'm not saying all those things are wrong. Maybe you don't want to hurt that person's feelings. move away from your social conditioning, but at least you should know that that's what you're doing. At least you should be aware. I'm only able to choose from these two options because of the situation.

that I've put myself imposed essentially, and this is the way I want to live. So yeah, I don't know. This is a, for me, a fascinating topic. Just the idea that there's... The majority of my life, I think I really, really very simply thought about how decisions are made. And like, probably. made my life way harder than it needed to be by thinking I have to do this or I need to do this when there's probably many, many, many, many other ways to do things. And sometimes those things just come up.

and you figure them out on the fly but yeah many times i guess i just imposed it it's either this or it's this and you know there's a a nuance to this as well where some people just get completely stuck and don't make any decisions. So in the end, just making any decision, just making a decision is better than making no decision. But yeah, I think what the point of this...

I guess, chapter from Derek Siver's book is there are always more than two options. Like what is something in your life where you're like, I either need to, it's usually, I either need to stay in this thing. or i need to get out of this thing right it's it's a or i need to like in the job i guess it's actually you could put you could put jobs relationships a lot of things on this friendships

I either need to be with this person or absolutely not with this person and it's over, right? Or I need to be in this job or absolutely not in this job and it's done. Whereas, especially in the job situation. I mean, that's pretty stupid because and I actually always thought about this with when people would either quit AJ and smart or, you know, just wasn't working out for a long term. And eventually I just would have to let them go.

where I was thinking like, if these people kind of would leave their options open or think more creatively about this, then there's probably lots of other ways we could have worked together. um and again i'm not saying i was thinking creatively about it but if you're especially if you're thinking of um a job and leaving a job um yeah you can There's so many ways you can work with that. There's so many things you can do, like hundreds of different approaches you can take.

It doesn't have to be this big, oh my God, I'm going to quit. And oh my God, the person's going to be so disappointed. Yeah, you know. There's a lot of ways you can think about these things.

I mean, even this podcast, right? I mean, for me, I was thinking, I don't want to do another podcast. I don't want to be stuck doing another podcast. I hate interviewing people. And then it was like, either I... Either I have a podcast, right? My dilemma was with the Jake and Jonathan podcast because that was popular. Much more popular than the unscheduled CEO.

I the problem I was having there was my there was a lot going on in my life and coordinating recording a podcast with somebody else is actually very complicated when both of you are extremely busy people.

And so basically the decision I made in my mind was I either do this podcast or I do no podcast. And eventually I was kind of thinking and, you know, looking at other formats and I was like, wait a minute, what if I. I mean, I still enjoy doing a podcast and there's still an advantage of having a podcast for the overall business as well.

So what if I just do it on my own time and do it whenever I want and do it within my own way of doing things, this unscheduled approach? And obviously that's where this podcast came from. You know, this kind of...

appeared out of that other option that I hadn't really been thinking about. And the funny thing is, I think it took me like two years to even figure that out because I just... thought i was listening to everybody else's podcast and i was like podcasts are interviews podcasts always have two people podcasts are always oh yeah that was another thing the editing the uploading schedule

all of that stuff, I was like, that's what a podcast is. That's what you have to do. But that just wasn't true. That just wasn't the case. And so, yeah, this piece of music that's playing in the background, if you know, this is not mine. This is just something. built into this roadcaster and i found it online or i found it online and i put it on the the podcast device so yeah there's always more than two options i think the nuance thing um

I don't know if I'm going to go into that right now, but maybe a different episode. But I can tell you that one of the, again, biggest learnings for me in the last couple of years is this idea of... you know i would go to i would go to one of my mentors or one of my friends um and i would kind of just have this dilemma again and i'd be like probably it was just usually i either have to do this or do this and

just listening to this other person or you know a mentor the fact that they would almost always present options that i hadn't thought about at all just made me realize oh man why do i keep why do i keep like making it and and often those other options were just way easier and way more enjoyable and way more beneficial to everybody else so i'm i kind of started to realize fucking hell um i just come up with

way too difficult like it's it's almost like i you know if life is some sort of choose your own adventure it is basically i guess if you believe in uh free will um if life is some sort of choose your own adventure game um a lot of us i think you know instead of having a like seven options when when a dilemma or when a challenge comes up instead of having like you know well actually infinite but let's say seven or ten options

We're like, no, I'm just going to choose two and they'll also potentially be extremely different from each other. So like, you know, doing this cuts everything off from this one and doing this cuts everything off from that one. And they're like almost like binary and often somewhat destructive. And I guess a lot of the reasons that we, if you think about quitting a job, I think a lot of the reasons that we make.

these extreme binary decisions number one obviously it's just that we've we kind of don't realize that we can redesign our operating system and realize that there's never just two the other is that

we don't want to have the tough conversations you know so let's say um the the idea of quitting where you're working um i know what this is like it's it's uh You don't want to let the person down. You also don't really want to let them know ahead of time because you don't want them to like change your or not give you a raise just in case there's one coming up. You want to keep all your options open.

all of that stuff um but in the end if you're able to let's say go to your boss and say hey look i actually don't really think this is working out for me um but i love

you know, this part of the company and this part of the company. Do you think that if I went freelance, we'd be able to do it a different way? And that was kind of how I did that in my very first job in Berlin. I was working at this company called... an icon thank you again guys for hiring me that was my first job um and uh and i could have done this way better but when i was starting aj and smart i was like hey guys look i really want to start my own business can i

Can I like reduce? First I was like, can I reduce my hours to four day a week? We did that. And then I was like, actually, I think being freelance is better for me. I think that that's just my way of doing it. And so I freelanced for them for a while until AJ and Smart was at the level where I didn't need that anymore. Right. Again, I could definitely have, you know, I wasn't the best at having.

tough conversations but uh it it gave me more options i think the point of this if you're listening to this uh and you'll be it'll be monday 16th of june Like what are the things in your life where you're like, I have to do either this or this, or it's some sort of burning the bridges, explosive decision you need to make. Maybe it doesn't need to be. And so, by the way.

By the way, sometimes it does. Sometimes there's just like a situation where you're like this fucking needs to end right now or I need to I just need to like have a clean decision here. It doesn't need to be super nuanced. And, you know, you don't want to get lost in nuance and, you know, again, not making any decisions, et cetera, et cetera. But there are just so many, so many, so many places.

where you do not need to be so binary with your decision making. It doesn't have to be this or that. It can be all of the options on the table.

and even working with you know the other person or the company or whatever it is i guess it could even be um i'll give you another example actually uh which has come up in a friend's lives and um uh, in my life. So, you know, okay. What's a really big decision. A lot of people make is I am going to move out of the city and live in like nature, right? I'm going to move a couple of hours outside of the city.

It's fine. I, you know, I love the city, but it just doesn't, you know, I just can't do it anymore. It's, it's not, it's just, it's just. Not for, I am raising children. You can't live in the city. It's like a binary thing. Many of you listening to this must know this dilemma. I think during COVID, a lot of people were like, I need to get out of the city. I'm going to have a place out in the middle of nowhere. Okay, so.

I was watching that happening and I found it weird because first of all, it's an extremely crazy decision, right? I'm going to stop renting an apartment and I'm going to buy a house. So you've now essentially built a lifelong mortgage situation that you're locked into. I'm not saying there's anything wrong with that. I'm just saying that. That is a pretty huge decision to make. And it's because the decision is, hey, I want a bigger space. I want to be away from city things.

And even though I love the city and love living here, that chapter of my life is over now. I think if you say that chapter of my life is over now, then you're officially in the space of... I do not have the mental capacity or interest in thinking about making decisions at like a deep level. Whenever anyone says. Hey, that chapter of my life is over now. Or, you know, just closing all the options. I'm like, okay. Like, you know, you're just saying that sentence. It doesn't mean it's true.

and it's it creates unnecessary dilemma so moving house right um you want to move out to you want to move away from the city you're you're feeling conflicted about it um but you you whatever you know And I'm always like shocked that people don't just rent an Airbnb for six months in the area you want to go to.

I mean, in many of the cases that when friends talk to me about this, there are Airbnbs. Yes, they're more expensive. Like it's an expensive thing to do that experiment. This is just one example. Just so you know, that's a much less expensive experiment. So renting out your place for a couple of months and doing an Airbnb in the area you're thinking of going to or something similar, something like also an hour away from the city, et cetera, et cetera.

It just gives you a feel for, well, what would that be like? Another alternative is what if we just had like a, instead of buying an entire, you know, house for 600K or a million, what if we just have a small. nice summer house thing that costs way less and we continue renting in the city. There's lots of different ways to think about this. There's lots of different ways to play these games.

But it's, yeah, it's the general thing that people do is, no, that chapter is over now. I am moving to the next chapter. And I see people like also like, especially over that COVID period. Or what I've definitely seen many times is people being a very common one is, OK, I've had I'm having kids now and building a family. And by the way, I'm not just saying this. This is guys as well. This is not just women.

And actually, I'm thinking mostly of my of guy friends where it's like, OK, I was excited about, you know, building something. I really enjoy my work. But now, you know, that that sort of. chapters over in my life and now I'm here I'm building a family and it's not that I think there's anything wrong with that I think that's lovely but the

longer-term results I'm seeing of such a binary decision. So the decision happening there, and this is, by the way, if you're listening from the US, you're going to be kind of confused about this. This is a very European thing, where then that person just... gives up like essentially switches off their brain for anything relating to career forever essentially and and you know puts you know

The sentences are, I'm putting, you know, I'm putting my career on the back burner. You know, this is, you know, the next 10 years or so, I think, you know, this is the chapter where it's about the family.

and uh not about me not about the business etc and you know i was curious i guess how these things would play out but how they play out in general that i've seen in most cases is that um and I can, you know, speak for the guys here is, oh, you know, five, six years later, being kind of feeling a bit like. you know after essentially you know in europe you can it's actually it's kind of amazing if you have a kid you almost don't need to work anymore um

But yeah, this sense that, oh, fuck, like I don't really have a thing I do anymore. Like when the kids are in school or when the kids are in the kindergarten or when they're not that interested in me anymore, I don't really have a thing.

anymore um and unfortunately then obviously i end up being the person who has a company that they would like me to give them a thing to do um but i'm like yeah there's there's you know you can you have to figure that out yourself it's it's it's the result of just taking making extreme decisions for no reason you know you don't have to you can just uh take time off and have a kid

then you can come back. You don't have to like decide like finally, as soon as this happens, I'm moving into the middle of nowhere. Work is no longer a thing that I do. As in, it's just like a background thing. And then I don't know what I do anymore. It's I don't know if this is going to connect with people. I don't know if you guys know what I'm talking about with that specific topic. It's very, very, very common here.

And then I, I, and by the way, like, it's not, it's not everybody. Almost every, I think almost everybody has kids in my company. Is that true? Let me think. At least half of the people in my company have kids. It's not true for everybody that everyone's like, I'm done now and then not happy about it. In some cases, people are like, I'm done now and they are happy about it.

But in many cases, especially I've seen this like with over the years, entrepreneur friends, et cetera, where it's like, oh shit, I have nothing to do or like a constant search for, okay, I'm. I had the kids. I moved out. I got a house. I renovated the whole place. Then it turns out we didn't want this. Then I moved to a different country. Then we got a house there. And it's like, in the end, the thing that they...

In the end, the kids are an amazing element of it, but having this binary thing of now the kids are everything and everything else is nothing is just one of those, again, self. created dilemmas and this is this dilemma i think is very big in uh europe like uh you know when I was having my first kid, you know, like people are like, Oh, that's the end of that. Like, you know, that's the joke is people are like, Oh, that's the end of all of this. And now that's the end of all of that.

Or like, I don't know, if you're getting married, people are like, oh, you better get it all out of your system now. And I'm like, wow, what the fuck are you talking about? Like, it's just a weird way to look at life, I think. extreme binary thing by the way i've got a boat i've got a bone to pick with some if you're a guy listening to this i've got a bone to pick with you i should have put this near the start of the podcast myself and my girlfriend were talking about this a lot recently

Um, if you're, if you're one of those guys who's like, um, first of all, if you ever tell me, if you're, if you're ever talking to me and you're, and you know, I don't know.

you're like oh well that's uh yeah that you know uh if only i could go back to being 25 and blah blah i'm like what what do you mean you know there's so many guys who i'll give you an exact example video games there's so many guys who when they find out that i play video games um they're like oh you know lucky lucky you you know the wife only lets me do that on on saturdays i'm like what do you mean

The wife lets you do your 38. And this is something which is very, very alien to me and always has been. That's so many. People just fully decide now this age equals this thing. And this age, I mean, there's obviously, you know, I don't want to be 50 years old hanging out in a... a club full of 18 year olds or something i'm not talking about this but things like video games like uh if you still i still enjoy video games um at the age of 37 and uh as long as i can you know

still do the things you know be a good father and partner all of that kind of stuff still run a business i'll do it if i want to and just that it just it's always confused me when i hear uh people saying things like oh you know and easy for you to say because blah blah blah blah I've been getting easy for you to say for the last hundred years guys you can you

If you want to play video games, you can. You can do that. You're allowed to. I'll give you the permission. Or if you, you know, it's not a... It's so weird to me. And again, play the game. Think about it. If you want to do something, there's always more options than just I do it and piss the person off or I don't do it and I'm pissed off.

There are multiple options here, right? There's multiple things you can do in these cases. Again, back to the binary thing. I've really gone off track. I just... It really annoys me. You know, the Switch 2 has come out. And I get, I hear it a lot. I hear it a lot from guys. I know a guy, I know a guy who's only allowed. Remember, this is a 38-year-old man who is only allowed to play video games for like an hour and a half on a Saturday.

Huh? What? Oh, God. Yeah. Anyway, maybe I'm wrong about something. i just find that crazy i just find that it's a recipe for extreme resentment and i think a lot of these things you know

um a lot of these situations where you think you only have two choices it creates resentment because you think if you're working at a company the thing i always found really weird um at aj and smart is when someone's like you know really feel I can sense they are almost acting as if they are... When someone's starting to get irritated at working at AJ and Smart, the vibe I get is like, they're doing me a huge favor.

by working at AJ and Smart. I mean, I'm happy if they want to work here, but that energy is a recipe for resentment. You're trying to find win-wins with these decisions that you make. It's not that, hey, I'm either I'm going to work here or I'm going to quit. And that, you know, those two decisions that you've now decided are the only two ways to play this game.

also mean that you know me in this case as the boss it means i have to deal with the fact that you're you kind of feel like you're doing me a favor by taking option one or i guess if you're in a relationship that you're not happy with um and you're like sticking it out and and you know you're like it's either i'm with this person or i never talk to them again um and then of course you're

doing them a huge favor by by being with them um because you're you're you're you've decided there's only these two ways to do things um yeah i don't know if this made any sense either it made a lot of sense and you guys are like this was interesting or i've completely fucked it up i don't know um

The video game thing, probably. I hope some of you guys... I hope some people understand what I'm talking about. And video games is just an example. I just find it very... It irritates me when... I guess I get irritated like, I don't know, if I'm like playing video games or I don't know, playing music or painting or whatever, just like things that I used to, that I enjoy doing.

Someone says to me, yeah, well, those were, you know, yeah, I mean, back when I was 17 and I had loads of time, that's what I used to do. But, you know. This it's just like this this chapter approach to life. It's like I'm a martyr. But. The other thing is we also make these decisions ourselves. We decide to have kids. We decide to be in a relationship. We decide to do these things in most cases. And so we can also decide on a day-to-day basis.

how we, you know, within those structures, um, what's what sort of things we also want out of it as well. Um, yeah, it's, it's a, I think that Derek Sivers. Article or chapter is a nice broad kind of way of saying when you have kind of tough decisions to make may be the reason it's tough. maybe is because you've decided there's only two, there are only two options. Okay? Okay. Yeah. That is all. Thanks so much for listening everybody. Have a great day. Bye.