Coaching as a Side Hustle, with Will Helliwell

Coaching as a Side Hustle, with Will Helliwell
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Brian Casel: [00:00:00] Hi there, Brian Casel here. I'm the founder of Clarityflow. And today I'm talking to Will Helliwell. He, when I connected with Will initially, his website was Notion Dad, and he has repositioned his coaching service to, under the name ProductiveDad. com. So we actually talked about that. The, uh, you know, it was a really interesting conversation. Uh, the discussion of his shift in focus from working with clients to help them set up Notion to helping them set up the software ClickUp.

Um, and, uh, you know, very similar to my conversation with Jason Resnick. It's an interesting idea to kind of attach a coaching practice to a very popular piece of software. And Will has been doing that effectively um, lately with the ClickUp software.

We also talked about Will's balancing of his [00:01:00] day job with pursuing a side hustle in, uh, in launching a coaching practice like this. He actually went from teaching guitar on the side to, um, to this sort of, uh, helping teams, uh, implement ClickUp and Notion and being more productive.

So it was a really interesting conversation. I hope you enjoy it. Here is, here it is. It's my conversation with Will Helliwell. Enjoy.

Will Helliwell, thank you for joining me. Great to meet you today.

Will Helliwell: And you. Thank you so much for having me.

Brian Casel: Yeah. So, um, you know, as we were just discussing offline, uh, I'm just trying to talk to as many different types of coaches and, uh, and people working with, with clients in really interesting and, and unique ways. And, uh, you know, your, your website, um, and your work really just stuck out to me. I think it'll be interesting to hear how you've been, uh, you know, getting into this [00:02:00] space and the, and the different kind of changes that you've been making in your business.

So, um, you know, I know that you've been, you know, recently going through like a rebrand and maybe we can talk through that and kind of hear it.. What I really love in general is like, uh, working in public and hearing about changes that are happening now or as close to real time as possible. I think that's always really interesting.

Will Helliwell: Yeah, I, I share everything on Twitter. Everything I'm doing is all in public.

Brian Casel: I love it. Yeah, I do the same. That's, that's really cool. Um, all right, so I mean, why don't we just start it off the way that I've been starting most of these interviews off with, if you can tell us a bit about what you do, but from the context of what a, what a client sees. So maybe you have a recent client or two. Um, who, who are they and how do they come across your work and, and why do they engage in services with you?

Will Helliwell: Sure. So my clients recently have been all about ClickUp, so it's mostly solopreneurs or maybe some small businesses [00:03:00] who have got click up and gone, oh, this is complicated. Like how do we set this up? Well, they've maybe tried themselves and it's all gone into a bit of a mess. And so they find me or see my stuff on Twitter and they come to me and they say, can you tidy this up? Can you give us some best practices? Can you help? And so I sort of do, you know, an hour call or they can book a few at once. And I go through sort of giving my knowledge so.

A little bit of backstory. I use ClickUp in my day job, so I'm sort of in it seven hours a day. And I think that gives me kind of real world, uh, evidence, let's say real, real world like things that are happening. So I can see stuff and mistakes that I've made. And then I can kind of move that on to the client and say, Hey, here's the mistake I made. Don't do that. So that's helpful as well.

Brian Casel: Very cool. All right, so there are so many different threads that I would like to pull on here that I think could be interesting for folks. I mean, I, [00:04:00] I recently, uh, spoke to Jason Resnick on this podcast, uh, and he is a coach who specializes in helping people set up and implement ConvertKit the, the email marketing tool.

Will Helliwell: yeah.

Brian Casel: So, so that was a really good example of someone sort of like attaching their coaching to a really popular tool. And in your case, you're doing it with ClickUp. I, think that's a really interesting pattern that a lot of, you know, coaches can, can really get into.

Will Helliwell: Yeah. I found.

Brian Casel: I think, I think we can also get into like your, your like balancing the day job with coaching, which usually is kind of difficult because calls and coaching sort of need, need to happen at different hours. Um, but, you know, maybe we can get into both of those.

Will Helliwell: Yeah, definitely.

Brian Casel: I, the, the last thing, um, I don't know the order that we'll get into them here, but like, you know, when we first connected, you were more focused on Notion and then the recent change to ClickUp. Um, why don't we actually start there? Like, tell, tell me a bit about this, uh, the current change that seems to be in real time here for you.

Will Helliwell: Sure. [00:05:00] So the reason I've changed, so in my day job, I was, well, it started off at the very beginning we were using pieces of paper. Like I, I was in the IT department working in a literal basement, and the team upstairs would bring down little squares of paper and say, this is the ticket. Can you work on that please? Like, yep. Okay. That was the system. Yeah.

And then we tried out a few things over the years. I think I've been there like nine or 10 years now in that day job. . We tried out a few things and then I saw Notion came along about three years ago now I think it was, and I was hooked. I was like, this is amazing. This is cool. Let's all use this. Let's stop with these other silly tools. So we used it for a while and I just found it was too, too free. You could do so many things with it, but that also meant you could break it really easily and.

Brian Casel: You know, I, I think so many people have had that experience with Notion, and I took so many years of kind of hating on Notion for that reason. Like, I, I would open [00:06:00] it up, I would love the way that it's designed, and then I'm like, I don't know how to organize this. And then I put it down for another year and then I try again, and then I put it down and, and maybe like the third or fourth round of that, I was like, you know what? I think I could get, uh, you know, get at least this, this current company organized in there.

Will Helliwell: Yeah, I think if I was using it just myself, like what I'm doing for myself at the minute, I think it would be fine. But because I was trying to use it in a team, it would break a little bit and then I'd have to go and fix it, and I'd just always be maintaining it. And we were working in sprints, and sprints weren't a thing in Notion at that point. You just, you had to build your own sprints.

So every week I would have to go new sprint. And I was like, this is ridiculous. Let's do, let's do something else. So I went searching. . And found ClickUp and it was built as a, as a task manager and a project manager like it. That's what it's for, rather. The Notion is kind of everything. What do you wanna do with it? ClickUp was, here's your project and task manager. Oh, and we do docs, so, okay, perfect. Let's try this. So I've gone through [00:07:00] the

Brian Casel: I, uh, I Had the same experience with, with ClickUp too, where it was like, I. I was dabbling in Notion, I was like, you know what? I think I need more structure. And that's where ClickUp seems to be strong. Like it actually does dictate like this is how things should be structured. Um, and then I kind of wanted more of the loose, like wiki style stuff for my, for the current organization and Notion. So,

Will Helliwell: Yeah.

Brian Casel: um, I'm, I'm curious, like, okay, so I understand like the difference in, or like the, the reason, especially if you're working with a team to move from clickUp. But for you as a coach and working with clients, why did that make more sense?

Will Helliwell: For that reason, it was because I was in ClickUp all day. So as Notion started progressing and they started adding new features, I couldn't keep up as I was trying to manage two apps, and one of them I was in all day, and the other one after work, I was like, oh, what's the update now? And it was just too much.

So I thought to help people with what I know. And that was [00:08:00] ClickUp. Like I don't, I do know Notion. I do still help some people with it if they need it, but I'm trying to just shift everything across to ClickUp now and say, I don't do Notion anymore. Hence I've gotta change NotionDad. Com to

Brian Casel: Yeah. So your website was Notion, dad, do you have, do you have the new website?

Will Helliwell: I've got the new, yeah, I've got the new domain. It's TheProductiveDad.com.

Brian Casel: Okay,

Will Helliwell: So

Brian Casel: good. So

Will Helliwell: it's

Brian Casel: not like, you're not totally tying yourself to one

Will Helliwell: Exactly, and then I can talk about more things. I can talk about parenting and how to do this kind of stuff and like right now, the little one, I just did bath time quickly. I've got a two year old girl. So bath time's done, did her teeth and then it's over to mum to do bedtime.

So it's, yeah, those kind of things I can talk about as well.

Brian Casel: That could be interesting. Productive. I mean, I like for like family vacations, I've like organized the calendar in Notion and share, share it with my wife and like show, show the Like, okay, that's cool and all, but like what time is the flight leaving? That's the only thing I care about,

Will Helliwell: Yeah. Have you got your passport?[00:09:00]

Brian Casel: Exactly. Um, so in terms of your clients, like who again, like who, what types of people or businesses have this sort of need to, uh, to hire a consultant to help set up, ClickUp.

Will Helliwell: So most of it at the moment seems to be like solopreneurs or entrepreneurs with like really small businesses. Um, and it's, yeah, they just come to me and they've either tried ClickUp or want to move off of Notion maybe, and they need some more structure or they just want to fast track in instead of going through all the documentation. They just wanna know how does it work? Can you set it up for me? I'm busy. Please do this.

Brian Casel: Got it. So solopreneurs like, do they have, is there any commonality in the types of businesses? Are they like software or freelancers, agencies?

Will Helliwell: Um, I. agencies a little bit. I'm thinking the last Notion one I did, so when I was still working in Notion, it seemed to be the Notion clients were the bigger ones who wanted big, [00:10:00] complicated systems. Um, but again, there was no real commonality between them. And now Click Up the commonality seems to be they're all solopreneurs or very small teams of people. There doesn't seem to be anything quite connecting them yet.

But I'm recording obviously, all of the consultant calls I do, I'm recording them and I'm trying to find right now like a common thread between them. What is the most common thing people are asking about, and then with the idea of boosting that knowledge and maybe productizing it at some point. But yeah, but then I can target, I'm like, oh, these people want that a lot. I should probably go and find more of them and help more of those people.

Brian Casel: Yeah. Yeah, definitely helps to, to niche down. I guess it would also help with the delivery of the service if it's like a predictable, everyone can even use the same templates or the same like packages

Will Helliwell: Exactly, yeah. Would really speed things up and I think I'd be able to help them more because I would really know that niche a lot more. Like my niche right now is, because [00:11:00] I'm on a software development team, sort of. So my day job is I build telephone services in Python. Um, so I'm in this IT department, and so that's really what I know. I work in sprints. Everything's estimated and sized, so that's what I know and that's kind of the people I'm trying to target who also do that. But if somebody gets in touch and says, Hey, I need help, I go, okay, I'll help.

Brian Casel: Interesting. Um, so yeah, like tell me a little bit about how you, well, okay, I have a question about this. 'Cause I, I got into this with Jason Resnick about how he works with ConvertKit clients. You know, anyone can just go to customer support for ClickUp ask like, how does this button work? And, and, or, or how do I do this or that? In, in the software, right?

Will Helliwell: Yep.

Brian Casel: What would be like the difference between someone just going to their, the, the actual company's customer support versus working with like a consultant like you to, get in there and work together?[00:12:00]

Will Helliwell: Yeah, I think there's a couple of things. One of it is it's a lot more custom, so you can ask for best practices. Where I feel like support, they're gonna tell you how things work, but if they, they might not say, you know, okay, you are a software team. Maybe you should work in two week sprints, not one week because of this, that kind of thing.

And then I think there's the prep as well. So if you know you've got a call coming up, then you have a whole itemized checklist. These are all the things I need to do. This is what I'm preparing for them. And then at the end, you can deliver some, you know, some nice PDFs or some ClickUp docs, which is really handy, and give them all the information that they've been requesting in a really nice way that then they could give to their team. Whereas support is, Hey, I have a problem.

Brian Casel: like you're really actually, you're like literally being productive with them. You're, you're helping them actually implement stuff, whereas a, an email support is just gonna sort of like link you to a doc and go, all right, go figure

Will Helliwell: Yeah, exactly. Yeah.

Brian Casel: Interesting.

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so how do you deliver this?

Like what, what does a typical engagement look like? I think you, you mentioned it a little bit, but like, when a client reaches out, what's usually the first thing that happens, do they, do they get a single call with you? Is it live? Are you doing asynchronous? What does that look like?

Will Helliwell: So normally they'd reach out DM on Twitter, or they'll send me an email, I'll send them a link to.. So my tech stack at the minute is, I think I'm using Cal.com to book calls. So I'll send them a link to that and we can have a 15 minute, half an hour discovery call.

Uh, but then there's different options there. So there's different links I can send them if I think, are they? . Do you want something big? I can send them like an hour long discovery call. So it'll be, have a call, find out what their needs are, and then I've got a template in ClickUp where I click a button and it goes, and it gives me all of my proposal, documentation and all the steps I know I need to do to [00:15:00] work with a client.

So then I'll send them a proposal based on what they've asked. And inside there it's also got some um, yeah, just more customized details about their project and say, Hey, is this okay? Send them a document to sign. And then this is the bit where I was actually really interested in Clarityflow because I feel like I need to onboard them somewhere and onboarding them at the moment is I can onboard them to ClickUp so they have their own space in ClickUp. but Clck Up when you get it it looks complicated. So if you've not used it

Brian Casel: why they hire you.

Will Helliwell: Yeah, exactly. . So they're hiring me to help with ClickUp and then I invite them to ClickUp and they go, but I don't understand what's go. This is all, yeah. . So I feel like I need something more simple. I've tried out Slack as well, so I've got a Slack group, um, that I can talk to people on. But again, that doesn't, it's, it's too everywhere. There's not enough structure. It's just they'll send me [00:16:00] messages at one o'clock in the morning and I'll feel like I need to reply to them.

Brian Casel: Yeah. Yeah. Also, the thing with Slack is like, those, the messages get easily lost, especially if they're like several weeks or, or months ago. Um,

Will Helliwell: Yeah. It relies then on

Brian Casel: is where,

Will Helliwell: it to a task and setting it all up and, yeah.

Brian Casel: Yeah. And also I think they expire too. Like they, the, the search, you know, and, and especially for something like what you're doing, where it's like We, we hired that consultant they, they helped set this thing up and that was like two or three months ago. But what was that thing that he showed me? I can't remember where it was or what it was. I, I'd love to be able to pull that up. That's where having like an archived conversation and, and messages obviously I'm partial to, Clarityflow for that sort of thing. But like, um, yeah, that, that makes a lot of sense.

Will Helliwell: Yeah. So the delivery will be at the minute, like a Notion Space or a ClickUp Space that I've built for them, and that's the delivery. And the link will always be there and working. . [00:17:00] But yeah, it's, it's disjointed at the minute, so I'm still, still building, still learning, still searching,

Brian Casel: Cool. Um, okay, so, so when when they get onboarded, you're like, what do they, what needs to happen? As they get started with you, and is it all leading up to like a date on the calendar? Like that Friday the 15th? That's the day that we're going to get on a live call and work out your ClickUp set up. Is that basically how it works?

Will Helliwell: Yeah, so there's two real systems. There's the get on a consultant call and if you book it and do you select the times with Cal.com, it's like Calendly they select the time they pay up front. There you go, sorted, you know, I'm free and it's done. Um, and they can put in, they get linked to a form where they can enter some more information and email address and everything so they can send me all the details that they need. So that's one bit .

And the other bit would be building out spaces. So for that bit, it's a bit more involved. That's when you [00:18:00] need the proposal and you need the start date, the end date, the deliverables, like what's gonna happen, when do you need it? Um, and what does success mean? Like there needs to be something that says this project is a success. That's one of the key things.

Brian Casel: So that's an actual project where, where you are sort of working in their ClickUp account, uh, alone and like setting things up for them and organizing things and then like at the near the end, you'd sort of like present and, and train them on what you've organized.

Will Helliwell: Yeah, exactly that. So it'll be a bit more, depending how long the project is, but a bit more, there'll be like three stages of, okay, you've told me what you want. I'll build it inside, ClickUp. I can then share a link with them and they can just duplicate it to their space. The same with Notion, or I can build it inside their space if they're happy with that.

Uh, and then get feedback on that. So there'll be like two or three feedback sessions until the final delivery date when it's training. They all kind of know how it works by then anyway, so away they go, hopefully

Brian Casel: Got it. Yeah. And what [00:19:00] does the training actually look like? Are you getting on like a group call with their whole team? Are giving them recordings that they can share with your team? What does that look like?

Will Helliwell: Uh, so most of it will be, there'll be weekly calls that I can have with, you know, the team or with one person. But I much prefer doing recording videos where it's structured. I know exactly what I'm saying at the time. They can ask questions afterwards. Um, but yeah, async is much more preferred. And then I'll do it in, I dunno if you've heard of Descript.

Brian Casel: Sure.

Will Helliwell: I'll do it in Descript and then I'll either just send them a link to the Descript video, just like you would with Loom. Or what I found is if you, upload a video to a ClickUp task, I dunno if it's intentional.. Well, they've said yes, that happens. I dunno if it's intentional, but the link to the video is public.

So even if the task is not public or anything, the link to the video is, so I'll do a video Descript or just straight onto the MacBook, upload it to a ClickUp task [00:20:00] maybe, and then send them that link. So then I've got a list of everything I've sent them.

Or finally ClickUp doc, put the videos in there, and so then they've got everything in one place to just go to one link. It's all there for them.

Brian Casel: Got Yeah. And that, that's pretty, pretty much how Clarityflow works is where you can have like a whole lineup of videos all in one place. Um, and they can even reply to them, but, but it's also like you can make it visible to the public so that like they're teammates who aren't even in Clarityflow, they still access the videos and everything.

Will Helliwell: Yeah, I was watching some, some Clarityflow stuff on YouTube today. To prepare. I thought it looked very cool.

Brian Casel: Oh, nice. Um, let's see, so yeah, why don't we talk a bit about the balance of, you know, working in the day job and taking on this, this coaching stuff. I'm curious, like when, when did you start doing the coaching on the side?

Will Helliwell: So my daughter is two and a half now, so it would've been [00:21:00] just, I think I started before she was born,

Brian Casel: So if having a two year old was, was not enough

Will Helliwell: That was, that was the incentive.

Brian Casel: a side

Will Helliwell: Yeah. But that was the incentive. Well, again, backstory, I've always had some sort of side hustle going on. Um, I started as a guitar teacher when I was 18, so I dropped outta college because I was like, that's when you were still allowed to, in the UK. Now I have to stay, I think till you're 18 or something.

But I dropped out of college and I went to music college instead and played guitar for two years, which was very cool and good fun. And then from 18, up until still now, uh, was teaching guitar. So I did that and worked in function bands and that gave me the taste of, oh, you're gonna earn money without having a job. Like this is cool. And then I got a job, , and so I've always had that itch to do it again. Yeah.

Brian Casel: Mm-Hmm.

Will Helliwell: So, yeah, daughter comes along. Before that, I was like, we're gonna need money. We're gonna need [00:22:00] to do stuff like pay for things, nursery. Nursery's, a whole extra mortgage at the minute. It's crazy expensive. So I thought, right, I'm gonna start this thing.

I created a new Twitter account called @NotionDad. 'Cause I was all in Notion at that point and just started it from scratch because my work, I tried to do something on the side before. But it was kind of directly competing with my day job, which is not advised, don't do that . And they found it. And so since then they were watching my personal Twitter and I went, okay, I won't do that again. Created a new Twitter. Let's do that again. But nothing to do with the day job really. It's more, yeah, just helping people.

Brian Casel: Wow. Okay.

Will Helliwell: So hopefully.

Brian Casel: You ever do the, get the, and I'm a lifelong guitar player too. Um, I've never given lessons, although I did when I was a kid to, to the kid down the block. But that was about it. Um, how, like, have you ever offered lessons online, [00:23:00] like remote over video like this, or is it always in person?

Will Helliwell: No, it's always been in person. When there was lockdown, I decided instead of offering it, I would just have a break, like just relax, which was lovely. But no, it's always been in person and that was my.. Back in the day, that was kind of my thing. I would go to their house rather than them come to me as well. So I would always take, I have my portable gear, I've got an iPad. Plug the guitar into there, I've got a little speaker. Sounds lovely. And that was my kind of selling point. It's like, I'll come to you. You don't have to do anything. So..

Brian Casel: That's great.

Will Helliwell: That was good.

Brian Casel: Um, so I mean, well, okay, the, you, you said that, that your, uh, your, your daughter you said,

Will Helliwell: Yeah, daughter. Yeah.

Brian Casel: I, I have two girls as well. Um, so that was like the inspiration to do like a side, a side hustle like this.

Will Helliwell: Yeah. It was the main incentive. And then you realize this is a lot of work, , so it still was.

Brian Casel: Do you, did you pursue [00:24:00] that as like, okay, this is sort of like something extra, something additional to supplement, or is the goal to eventually phase out the day job and go like full time on like a solo consulting thing?

Will Helliwell: I think the goal is to phase it out. At the beginning it was just to get some extra cash. I had that. I had guitar teaching. But it's always, it's still exchanging your time for money. So yeah, the goal is to eventually still do that, but then be able to choose your clients a bit more, like take on the really cool ones and then also productize it a bit as well.

So replace the day job and have some sort of product, which then gives you the money to work on even cooler stuff and make cooler products and yeah, that, that's the dream anyway.

Brian Casel: I think that's where, you know, niching down and, and really getting focused on like one type of client who has a very common repeatable need. That's where, that's where that can become a lot [00:25:00] easier, I think. Not only to to like market and grow the business, but to be able to deliver it in, in a repeatable way to a point where you can just train an assistant to do, to like, you know, follow this process. 'cause we've, we've done it a hundred times, you know.

Will Helliwell: Definitely, and I was thinking about this yesterday as I was going through all my notes, and I think one thing I want to really focus on, something that I've got experience in is . Moving people from Notion to ClickUp. I was like, 'cause that's a whole, the whole thing going on there. You've got the wiki side, you've got the tasks, you've got so many things to think about, you've gotta learn, ClickUp.

And I thought, I've been through all of that. So that would be a really good thing. I need to see if the demand's there. But that'd be a really good thing, I think to niche down on and build, productize and help people with that specific flow.

Brian Casel: Yeah. I like it. As we start to wrap up here, I mean, how are you finding these clients? Like how, how, how do you get in touch with folks who might be switching from notion to ClickUp or they're trying to adopt, ClickUp with their team? You know I, I don't think it's a common [00:26:00] job posting, right? Like, I, I need help setting up my ClickUp. Or..

Will Helliwell: Yeah,

Brian Casel: How do do you, like, where would you find folks who currently have that need?

Will Helliwell: So I haven't been searching actively. It's all been inbound just because, again, so we're talking about balance. I. I don't have too much time to do, like I could do take on one big project in a month or take on a few calls, like a couple of calls a week and that will be busy enough.

So it's all been inbound and lots of it is focus.. So I'm focusing on Twitter, I'm re-posting to LinkedIn 'cause everyone's like, yeah, go search for people there. But I think that's where I need to do the outbound, 'cause the things I'm posting on LinkedIn aren't hitting, but Twitter they are, but it's probably 'cause it's the same content. I'm just reposting, but most of it is on Twitter.

And then I'm known now for ClickUp. So I think I officially became a ClickUp ambassador and then started working with them a bit more closely. And, um, yeah, [00:27:00] so people will tag me, someone will say I need help with, ClickUp, who can I talk to? And then someone will tag me and I'll go, oh yep. So I'll DM them and jump in that way.

Brian Casel: I think it's great. Again, I was talking to Jason Resnick about this, and I think it's also another running theme with most coaches these days. It was like becoming associated with, in your case, it's like, it's with ClickUp, right? Like, oh, this person needs help with ClickUp. Will is the guy for that.

Right? Um, just the, that, that brand association. Um, but it doesn't even need to be like a tool. It could just be, you know, a concept or, uh, you know, some, some top, some common commonly known topic. Like, oh, that's the person for that,

Will Helliwell: Yeah, definitely. Like for me, if I needed, uh, help with note making or note taking, I'd go Nick Milo. He's the note making guy. Like that's what he does. He's known for that. So I don't want to, again, I don't wanna be stuck in a box. I don't wanna make the same mistake I had made last time. I'm going, I'm the ClickUp guy. It helps [00:28:00] with that.

But I've also just finished taking a course, um, called the ICOR Framework by Paperless Movement. And so I've just gone all through that. And that's really interesting because it gives you. A more holistic framework of your productivity system, and then once you kind of sussed it out yourself, you could then help people with that. So there's another thing bubbling on the side that I'm thinking about helping people with and branching out a bit more again, ClickUp and then productivity stuff.

Brian Casel: Yeah. Uh, The Productivity Dad, that, that's the, uh, that's the website. We'll get everything linked up and, um. It's really interesting to see this like transformation and, and kind of, uh, all all the possible roads that you can take take with this. So,

Will Helliwell: Yeah.

Brian Casel: um, Will, thanks for, uh, thanks for taking the time. This has been, this has been really cool to, to hear your story.

Will Helliwell: Yeah. Thanks so much. It's been been a pleasure.

Brian Casel: Alright,

Will Helliwell: Cool. Speak to you soon.

Brian Casel: See you.

‚Äč[00:29:00]

Coaching as a Side Hustle, with Will Helliwell

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