A Very Honest Update on Regret, Feeling Like a Failure & Painfully High Standards - DTJ Ep 59

Matthew Kelly talks about lingering regret from a business collapse around 2021 and the weight of impossibly high standards. His current startup makes millions, but he still has nightmares and feels like a failure. He's trying to shake the feeling by building something bigger.
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Back with episode 59 of Documenting the journey. I'm not wearing a hat for once. I thought I'd mix it up. I do very much need a haircut. I've gone back semi blonde and I'm already being inconsistent with the pod. And a few people message me, which always amazes me about where's the pod? Etc etc, and I just feel like I'm becoming boring by making these videos. The nature of doing this and documenting shit at my desk, which is how I do it, is that it has to be like real and raw behind the scenes. Not even behind the scenes, just like a little snapshot of me sat on my desk talking about being behind the scenes. And it has to be transparent and real and all this shit. Otherwise it kind of defeats the point of it. But the nature of doing it is that. And I saw a comment on one of my videos recently and it kind of, I mean I definitely agree with it, but it kind of resonated with me, I think basically someone said I look fucking depressed and. And moody all the time. Something like that. You know, kind of had a tone of like genuine concern and like what's up sort of vibe to it. Well, I thought a few things. Firstly, I tend to only make these videos at least recently. I don't know if it's a new habit of mine when I'm feeling like pensive and reflective and maybe a bit like down about the process because when I'm feeling motivated and better, I just don't feel the urge to make a video. I don't know, maybe it feels like less cinematic and less dramatic and so on. But having said that, I look back at videos just before this. I literally look back at a video from Summer22, which is probably when I've felt the happiest in recent years. I'm trying to think like what was the difference then? So yeah, I'll try and keep this video semi short. And I was thinking about it. I mean I think about a lot of things. Chronic overthinker, probably like a lot of founders in particular because by nature of having a. Probably overactive mind is what makes you be a founder to some extent or gives you the ability to believe you can be a founder and do shit that people don't normally do. I'm already rambling. But yeah, I was thinking about a bunch of shit. And yeah, to be completely honest, I've not been very happy recently. I mean, I'm not going to go make a fucking sob story video because I've done that before and I've deleted it. And I kind of regretted sharing that part of my mind on the Internet because that's the dichotomy of this. And the thing I struggle with is for it to be authentic you have to be transparent. But I do think there's a line of what you should share on the Internet. I really do. Just, just from a professional sense, if anything, not just saving face and keeping your brand and all this. But yeah, so I wouldn't say I'm a particularly happy person in general. That's kind of my, my genetic baseline, sadly. I think sometimes I am, but I go through periods and you know, I'm not going to go into this. People that know me know I've struggled a lot with that for many reasons. But you know, a side of it is biological and genetic, but another side of it, which is probably the more prevalent side of it if I'm completely honest, is in summary, I just thought I'd be way further ahead in life by 28. I really did. And it's really sounds like bitter and resentful and I hate that part of me that comes out when I feel this way. But it's just true. When I was 18 or probably more relevantly when I was 21, when I started like making a bit of money and traveling the world and being a full time founder and all this and everything was so exciting. I probably, to be honest, I thought by 28 I'd have 30 million quid and I'd be fucking living in a mansion in Bali and I don't have that. But also maybe more, more relevantly like I thought I'd have built bigger things and be more. I don't know, I thought I'd be somebody more than I am now. And that's. It does stem from just ultimately and I've had a therapy about this to be completely honest, but it's not helped me that much from transparent. Basically my entire like self image and challenge with myself and kind of the challenge of being, which I struggle with, to be honest sometimes without sounding overdramatic, is it comes from comparing myself to the 0.0001% because I believe I can be one of those people, not just financially but also like having built something that's big and respected and all that and ultimately not being there yet. So yeah, the headline is I genuinely feel like a massive fucking piece of shit failure every minute of every day. Pretty much, give or take. Like maybe not every every minute of every day, but all the time. Like most of the time there is that shadow of I do not feel remotely successful no matter what anyone says to me. And, you know, all this virtues and this is all this virtue single on LinkedIn of like, everyone's so successful and happy and all this and it's just all bollocks. Most of it's bollocks in my opinion. Whereas I'd like to think I'm the opposite of that kind of larping where I'm probably doing decent stuff. I mean, people tell me, you know, building a brand in this market, like, you've achieved a lot and all that, but I genuinely don't feel like I have at all, not even to 1%. I feel like a complete loser with my business most of time. And I know it's unhealthy and very toxic, I genuinely know it is, but it's still there. And I think a large part of it is my last business failed dramatically and I became really. I know that's where I started the poll, I spoke about that. But I reckon that shit haunts me more now than it did then because I know from a lot of people on the outside, I know you had an econ brand that failed, but actually I lost a fuckload of money. I completely lost my confidence in who I was as being this like, driven, creative, kind of happy, go, lucky founder type. And honestly, ever since that's it, that ever since 2021, I genuinely feel like I've been a different person because, yeah, got fucked financially, but also, and probably more prevalently, like got destroyed on social media. My reputation was pulled through the mud and, you know, thankfully I corrected that because I didn't do anything wrong ultimately, but, well, I guess I did. Cause everything's my fault as a founder, but you get the point. And yeah, probably, like, I mean, that was nearly three years ago that business went into administration, but I still think about that every day and I have so much regret around, oh, fuck, Coulda, woulda, shoulda. And like, the headline figure of Coulda, woulda, shoulda for me is I could have got that business right and made 20 million quid when I was 26. And I didn't. And that really pisses me off every day. But also it just kind of sits there like, yeah, I don't know, it's very painful because I do have a lot of regret for not getting that right. And the fact that I ultimately fucked that up and, you know, lost a lot of money, fucked my credit rating, shit that no one speaks about when stuff goes wrong. And more importantly, completely destroyed my confidence and probably like my subconscious fabric of who the fuck I am, to be honest. And ever since then, I've been battling to kind of get back. And it's funny, in like 2022, if anyone follows my shit, you know, I lost a load of weight, got fucking shredded, ran a sub 3 marathon, started the business, got over my ex girlfriend, all this shit. It was like a pretty good story. And then 2023, I sort of felt like the dust had settled. Things are going pretty well, but it just kind of felt meh. And then maybe now in recent months, I don't know, because it's a new year, you know, I was turned 28 a few months ago. The business is growing. We're back to kind of scale that I was previously at Nearly at the Peaks previously. But it's almost like because everything's going quite well now, it's giving me more time to kind of escape that. That deep hole I was in two and a half, three years ago, which I obviously documented a lot of when I started the podcast. But, yeah, it's almost like now the dust is fully settled on that I've had more time to think about. Yeah, like why I feel this genuine, don't know the right words. Like why I genuinely don't feel good about myself a lot of the time and lack self confidence. And it's weird. It's a weird, strange combination. And because I'm ultimately net optimist. You have to be, as a founder. But I also really fucking don't like myself a lot because I should be way further ahead. And I know a lot of people that are way further ahead than me, that are younger than me and some that are older than me and some are the same age and, you know, they're great friends to have. But the downside of that, I've been fortunate enough to spend my formative years since, like I was 20 years old, surrounded by entrepreneurs and ultimately people that have done very well, either financially or, you know, built sick brands and genuinely they go hand in hand and lived cool lives. And I guess also this is a fucking therapeutic one, isn't it? But I made a lot of money and saw a lot of fancy things, had all my dream cars, lived in the penthouse flat, traveled to every fucking country on First Class on Amex Points. All this in my early to mid-20s and the bar has been set so high for me now. But I guess things that would, you know, really excite someone. For example, I remember when we went into Holland and Barrett, a few of my team members said, oh, this is amazing. Like investors said, it's amazing. Are you happy? And I just literally, I said it doesn't fucking mean shit. And maybe that's a great prudent, you know, kind of, I don't know, great robust founder mentality to have. But also I genuinely didn't give a fuck. I was like, it's a tiny order. Loads of people have done this before. I'm not some virtue signaling larper that's gonna then post this on LinkedIn. Although I probably did. Cause you kind of have to, but I just didn't feel anything about it. Yeah, I don't know, it's funny and I think part of that is cause I set such high standards for myself and I compare myself to people that are running 30 million pound brands and 100 million pound brands and all this. But also I was exposed to, I guess, such rapid. Well, it wasn't actually that rapid. Oh, but you know, such young success, like I was driving a Ferrari when I was 24. Like, I guess reflecting on that, that was very unusual. I don't give a fuck about material things in the same way that I used to then. And in hindsight I was very stupid with a lot of money that was coming in at the time. But you know, don't regret it. But that felt normal to me back then because I hadn't grown up around it at all, come from a normal family. But I mean I'd grown up in my formative entrepreneurial years around that and normalizing that and yeah, I mean that's great things to have happened. I've experienced so much and met great people and you know, experience bad things as well in business which have made me objectively a better entrepreneur. But the shadow that it does have on me now is I've done all that ultimately the past few years my life has been, I guess less lavish because, I mean, partly because I was stupid back then, but also partly because the business has been smaller and I've intentionally, you know, chosen to lead a slightly more humble life, which is probably a good thing. But yeah, there is a contrast and I think growing stuff and being profitable and all that is a lot harder than it was. I'll just fucking say that and everyone will say that. But yeah, I don't know where I'm going with this. But like there's a few things, genetic predisposition for sure, which I'm not going to go into, but I've made videos on that before. Massive failure in the past and well, genetic predisposition, being exposed to Success really young and setting my. As a result setting my standard for everything so ridiculous high like I guess, you know, compare myself to the 0.00001% in everything I do and therefore when I'm even in the top 1% or top 0.1%, whatever it is in something, I still feel like a massive failure because there's people ahead of me. And then the big, you know, the big whammy was my massive dramatic failure three years ago, which I don't think many people can understand how painful that was. And I'm not just talking about oh, the business went into, you know, there was a lot of shit I haven't spoken about that happened off the back of that. And I'm massively scarred by emotionally more than anything. But yeah, it's probably something I have to deal with. And I convinced myself that the answer is just make this business way bigger and make a fuckload more money and then I'll be happy and I'll. And that's the answer to everything. But a part of me is now like mature enough and self awareness now that I probably won't even fix it. And I just always think and I guess it genuinely is PTSD or trauma to some extent and I hate or I hate like people overusing these things, but it fucking is like I've literally had nightmares in the past few weeks, like bad dreams, thinking about, I guess, my shortcomings in the past and shit. And you know, convince myself that my family don't fucking want anything to do with me if I'm not successful, which is not true. But I genuinely convinced myself with these stories in my head and they come from a very negative, dark, cynical, resentful place, which I don't like about myself at all. But it just, it is there. It's like a dark shadow of everything I do. I've even convinced myself that my fucking girlfriend's gonna not like me soon because are not successful enough. And like that's kind of painful to say and I hope you don't listen to it. But that's just me being like the most real I've probably ever been on the pod, funnily enough. And yeah, I think the answer is you got to fucking deal with it and be successful. But until I get to, you know, massive heights, I'm probably always going to feel like a genuine fucking loser. And I would really love. I'm envious, not jealous. I'm envious of people that have lower standards for themselves, which I guess is probably where it comes From. I don't say that from an arrogant way. I say, like, you know, someone has a normal job and a normal income and a normal life and they're genuinely happy with that. I'm actually fucking jealous of that because, yeah, it's pretty poisonous. Like, the. The calibration of my mind as a result of my formative years in my early to mid-20s as a founder has really screwed my, like, mental foundations going forward. And that's quite a good way to put it. I'm pretty proud of that, the use of words. But, yeah, it doesn't make it fucking easy. Makes every day, not every minute of every day or probably even every day, but a good chunk of my life is there's always this kind of cloud in the back of my mind that I'm a fucking loser because I've failed before. And I feel like I'm the only one that's ever failed because no one fucking talks about it. And I did it very, very, very dramatically, especially for like, that age and point in my life, and I've never really got over it. And, yeah, this is me probably just giving myself therapy and maybe just explaining why sometimes I come across like a fucking cynical, depressed, for lack of a better word, character. Because that isn't like the real me. The real me is like the real me, like the version me that I kind of prefer and see in a lot of my past videos and endeavors, is kind of like super optimistic, super bullish and everything. Work hard, play hard. But yeah, there's been a shadow across me the past few years and I'm gonna stop rambling, but maybe that explains why. But, yeah, I struggle with it every day and I don't really know where to go with it because I've spoke to my mates about it and they don't feel that way about themselves. It was difficult and I feel like I don't want to come across like some fucking pussy because I'm not that either. Because I've never been someone to just, you know, put my head in the sand and not get on with shit. Like, I train, I look after myself, I work hard, I'm building something. You know, by 99, I'm also aware of the reality from, like, most people's perspective. By 99% of people's perspective, I'm doing really well. I've got their dream life. I'm running a startup that I created. We're doing millions in revenue. You know, I'm on the right path, but I just don't feel that way. So, yeah, so I need to work on. And this was meant to be a 5 minute video or a 10 minute one and it's now 18 minutes or something. But yeah, I don't want to be too doom and gloom, but I just thought I'd give context onto why maybe I come across that way sometimes and especially on this channel. And yeah, gonna keep working at it. I'll keep documenting the process of trying to shake that feeling about myself off by ultimately building a fucking big business. And that's not easy, but I've committed to trying to do that and I've also committed to trying to document doing that on this channel. And that means just being real. And hopefully this is relatable to some people because, I mean, that doesn't feel like it is. And that's what makes it harder because I feel like I'm the only one that feels like this. But I'm sure everyone's got their own shit they're dealing with and this is a big chunk of what sits in my brain, probably like unprocessed a lot of the time. And sometimes I think I'm shooting myself in the foot by putting this stuff on the Internet. Because what if the wrong person listens to it? What if it gets taken out of context? What if it gets shared to someone that I'm trying to come across as professionally or whatever, or a new team member or something? But yeah, that's how it is right now. Business is growing, business is chaotic. Definitely in that rapid growth, like, fuck me, everything could break any minute, sort of time. There's a lot of problems, but team is growing. I know what I'm trying to achieve this year. I've been very clear on that and just get on with it. Time is flying. It's February 6th already. Cheers for watching. Appreciate, appreciate the support on the pod, the messages people send me, which is still quite a lot. Which, yeah, it's very kind. Yeah, if you're in the trenches building some shit, then I salute you. And if you're not, have fun as well. I'm probably quite jealous sometimes. Anyway, enough. I'll catch you in the next episode. Cheers for watching it.










