#495 The September Reset: Stop Old Habits, Start New Wins

2 Sep 2025 · 39 min · 15 chapters

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In short

September “reset” habits—what to start and stop to protect your future self, plus a team exercise to share starts/stops and ask for support. They also promote a free “Squiggly Careers skill sprint” (15 Sept, one week) focused on squiggly skills and AI prompts/tools.

Guests

No guests. Hosts are Sarah and Helen (Squiggly Careers podcast).

Key claims

September creates a “fresh start” effect (fresh start/new pencil case analogy). People struggle to protect future selves; do starts/stops as reflection and team support. Accountability helps (e.g., Wind Watch review). Small actions beat waiting.

Notable examples

Helen’s starts: weekly “borrowed brilliance” and “parallel learning” via Peloton + podcasts; monthly mentor conversations (Sept–Dec). Helen’s stops: stop writing actions on post-its; stop moaning about Mondays (consider “as-is/to-be” meeting changes). Sarah’s stops: stop waiting to respond to emails; leave phone behind in evenings to be present. Sarah’s starts: weekly borrowed brilliance; build stuff from scratch using AI (e.g., Canva AI cards).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Fresh Start Effect

1:04 to 2:09

Discussion about the psychological impact of September as a time for new beginnings.

“two weeks until the start of our Squiggly Careers skill sprint.”

Fond Memories of School

2:09 to 3:00

Hosts share nostalgic memories related to school supplies and the back-to-school feeling.

September Starts and Stops

3:00 to 4:22

Hosts discuss the importance of identifying personal starts and stops for the new season.

Sarah's Starts: Borrowed Brilliance

4:22 to 7:30

Sarah shares her first start of committing to a weekly borrowed brilliance segment.

“So we've both got two, two starts and two stops that we haven't shared with each other before the episode because we just always think it makes it more interesting.”

Building with AI

7:30 to 10:34

Discussion around using AI for building projects and exploring creativity without code.

Helen's Parallel Learning

10:34 to 14:00

Helen shares her experience of integrating learning with regular activities like Peloton.

Parallel Learning: Incorporating Education into Routine

14:00 to 17:44

Discover how to integrate learning into everyday activities to maximize time efficiency.

“And that was like four hours a week, if not more, when I could listen to podcasts.”

Intentional Mentoring Moments

17:44 to 19:24

Learn the importance of seeking out mentors and setting intentional goals for personal growth.

Overcoming Email Delays and Responsive Habits

19:24 to 23:06

Explore strategies to improve email responsiveness and reduce unnecessary waiting.

Being Present: Balancing Work and Family

23:06 to 27:26

Understand the value of being present with family over distractions from work.

Show all 15 chapters

Streamlining Note-Taking: The Case Against Post-Its

27:26 to 28:00

Learn effective note-taking strategies to reduce clutter and increase organization.

Organizing Notes and Actions

28:00 to 30:06

Learn effective strategies for managing notes and action items to reduce stress.

Improving Mondays

30:06 to 31:36

Explore ways to cultivate a positive mindset and improve Monday productivity.

Reassessing Monday Meetings

31:36 to 33:59

Discuss the need to reassess and potentially restructure Monday meetings for better outcomes.

Accountability and Support

33:59 to 36:56

Understand the importance of accountability in personal and team goals.

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Transcript

Automatic transcript. May contain errors.

0:00Helen:So it's September, obviously I was using AI to see what was on people's minds. Restart, reset, refocus. I guess it's just a memorable time isn't it? That September time when it feels like I can do something different now than I was doing before. And things that you think, now is the time to stop that thing because it's getting in my way. So we thought we would share our starts and stops and hopefully inspire you to think about it too. We're not very good at protecting our future self. We have to think about the being kind to the future version of us and what we want that person's Monday to look like.

0:33Is it because that start and stop was too ambitious? Is it because you need more help from someone? This conversation is useful hopefully for two things. One, for your own reflection, but also for your awareness of what other people want to start and stop and how you can support each other. So we would highly recommend that you do this as a team activity.

0:51Helen:Hi, I'm Sarah. I'm Helen. And this is the Squiggly Careers podcast. Every week we talk about a different topic to do with work and share some ideas and actions so we can all navigate these Squiggly Careers without a bit more confidence and control. And it is now only two weeks until the start of our Squiggly Careers skill sprint. This is the third sprint that we are running, but we've changed things up a bit this time. So this sprint starts on the 15th September. It is only for one week, so kind of easy to start and stick to. The past ones we've on a 20 days. This hopefully feels a bit more accessible.

1:21And our focus is on squiggly skills times AI. So we've taken the five squiggly skills, strengths, values, confidence network, and future. We've got some AI prompt and some new tools for you to try out. So if you fancy a bit of an accelerated start for your development in September, sign up for the sprint. All you need to do is go to squigglysprint.com. Sign up is completely free and we will then send you everything else that you need to know.

1:46Helen:So it's September and obviously I was using AI to see what was on people's minds and also I asked our team. I feel like they're my two default sources of like reality and AI and everybody pretty much said they do see September as a bit of a restart, reset, refocus and we talked about it before and I talked about it with Katie Milkman in our interview this idea of the fresh start effect and this can be any moment it can be a Monday it can be post a holiday but I think there is something about a September probably because we were all conditioned to go back to school in September at some point during our lives that you never quite lose that you know the sort of I wouldn't call it the fresh start in September I'd call it the new pencil case I used to love getting a new pencil case pencil case I love it it was like the best and a new school bag that got very exciting when I got a bit older but so maybe I should get some new stationery that'd be exciting right slight diversion we're allowed to a little what was the best school bag that you ever had like the one you know like the one that you remember yeah so I actually do and I don't have a very good memory I do really remember this so it was um pretty much all black because obviously you don't want to stand out or I didn't want to stand out certainly not the school I went to um it was like a kind of like a satchel one so quite quite a sort of square rectangle shape so it like folded over with like velcro and the brand was quicksilver little a little um quicksilver logo in the corner which felt not too obvious not everyone was going to have that but just that little bit different um and i loved that bag mine was a kangaroo bag and it was black with a big thick white stripe down the middle i remember those simple symbol was uh you know like an actual it was a kangaroo right it was like right in the middle and i thought it was the best bag ever um they're fond memories but um that's the only time i'm going to talk about bags i think in this episode but it is it's i guess it's just a memorable time isn't it that that september time when it feels like i don't know it feels like i can do something different now than i was doing before um and so that energy has inspired this episode which is about your september starts and stops so things that you might want to start doing because you've got this energy and it feels like you might want to use it for something sort of productive for your development and things that you think now is the time to stop that thing because it's getting in my way and I've got the kind of motivation to just stop that thing happening anymore so we thought we would share our starts and stops and hopefully inspire you to think about it too.

4:26Helen:So we've both got two, two starts and two stops that we haven't shared with each other before the episode because we just always think it makes it more interesting. We were also talking about and our team don't know this yet so some of them do listen so this is coming team uh we are going to repeat this exercise um as a team and ask everybody for one start and one stop i actually think this is a really good conversation to have as a team at the start of september you know so that you know where everyone is what's on people's minds give people a bit of chance to to think about it beforehand but it's quite a nice way of reconnecting and recalibrating i think as a group as well as you can also obviously do it individually uh helen do you want to go first or do you want me to go first oh you go first i'm more interested in yours go on what are your starts my two starts yeah um so i liked the starts better than the stops i found the starts a lot easier which probably says a lot about me i don't want to take things away but i just want to i want to do things so start number one is a weekly borrowed brilliance.

5:30Helen:So I sometimes in an ad hoc and occasional way write a borrowed brilliance segment for our Squiggly Careers in Action newsletter and I really I've really enjoyed doing that because I think it's a forcing function to make me read, watch, listen to or just think about like who and where am I learning from at the moment. Then I did a job crafting exercise quite recently and that sort of identified that I feel like borrowed brilliance is something that I can own I can make happen and it fits really well with my values of achievement because I feel like I've I think I feel like I've achieved in the learning as well as in the outcome of actually the writing up so I feel like I get like a double dose of achievement it definitely helps me to have ideas because I think I start to connect dots in a kind of different way and I think when I look back at lots of the ideas that I'm really proud of that perhaps we've worked on together they've often been sparked by some borrowed brilliance and fun fact having read Moral Ambition for a recent borrowed brilliance most inventions or ideas obviously are sparked by something that someone else has already done.

6:40Helen:Learning obviously it kind of is a learning activity and variety because every borrowed brilliance is different I think it kind of creates more variety and so until now it's been occasional in August I've been able to make it I've done like two a week because I've had the space and the ability to do that and I think I've just realized I was like I love it I've got ideas for how we could make it bigger I've started to put them all in the same place so I can see them all stacking up and also I want to make sure you know they're not all too similar and I don't I could imagine doing the same one twice in like a year's time um but that's that's one of the things I want to start is like from September when my work week looks very different to August I want to commit to it and then it would be so easier to just stop doing it every week and just do it and go back to that ad hoc um so yeah that's my first one can I ask you some questions of course um is because at the moment you have as like a source of accountability a fortnightly requirement to borrow brilliance into our newsletter are you thinking you'll do that weekly in the newsletter now um well what's interesting for me is the fortnightly thing for our newsletter I ignore anyway so that just that doesn't which our team may or may not appreciate as Helen sort of shakes her head in disapproval slash disbelief that that doesn't actually motivate me um it that that's not the thing that's made me do it I think the thing that's made me do it more has been the focus of oh a book I'd like to read an article that I found interesting like it's the discovery that is the bit that works for me so I the reason I'm going to do it every week is I'm basically going to create them every week into this document we can use them for the newsletter every week if we want to but what I thought is I would post it on LinkedIn every week it's just a borrowed brilliance so I don't really post on LinkedIn lots most of the time because I think I'm not sure I've got anything particularly interesting or useful to say um and I think my then also my filter of my own personality gets in the way there's like two things it's like can I be useful and then there's like do do I want to do it with a kind of more introverted personality um saw some interesting stats recently about how young people are becoming more introverted from the FT um and then Bruce Daisley actually posted them on LinkedIn today as well if you want to look at some trends of how personality traits are changing very interesting I was like oh maybe that could be a borrowed brilliance so I think it's got my like I and like antennae for curiosity kind of sparked it so I think I probably do need some accountability the question behind the question was that it was like great more content for the newsletter but also I was just thinking you know what makes it useful for you but useful for other people too so I think people having consistency like knowing they're going to get this is makes it useful for them and then I was also thinking if you've gone to the effort of creating the brilliance you I feel like oh it should go in the newsletter it should go on LinkedIn and it should go to our team like it should I feel like one bit of knowledge from you one bit of brilliance could belong in quite a few places so it helps more people so that was that was that was the question behind the question yeah and I think the thing probably I need to think about is I'm never super motivated by like the sort of the oh always post it on a Friday if anything I think I find that sort of gets in my way Helen's like I know you well but I think if I knew there was a bigger goal for it um which is not hard to imagine if I knew oh at some point we're going to put it all together and we're going to create create a borrowed brilliant series or something like the pod book we've done or whatever it might be then I think that that would help me more um but it's early days but I do I it's made a difference I look forward to your borrow also just one tiny little bit feedback I think when I see it it inspires me to stay curious because I'm like oh Sarah's reading around an area and I'm cool I want to read as much so it has a does have a like a secondary benefit as well okay so that was your first start weekly bar brilliance what was your second so my second one is to build stuff from scratch using ai so i've got a lot more confident with ai um during 2025 so both of these starts are definitely built on something that's gone before and actually i've been really enjoying it i think i've been experimenting i don't think I'm the earliest adopter when it comes to AI but I I've got to the point now where I've played with it I feel like I've been quite playful and that's that's worked quite well ahead of the sprint in a couple of weeks time and I sort of now want to move into actually kind of building things without code and I've seen some really good examples of how you can do that I even experimented with one today where you can kind of create these like cards in Canva using AI um so you're not just using you know a lot of the time you use AI either as a thought partner maybe for ideas or to build on ideas and it's prompting it's you're using a lot of prompting I feel like I've got really used to using that now I've kind of added that into my day-to-day so I'm like obviously you want to keep adding it in but what I haven't necessarily done is like created anything or built anything um so that is my other start oh remember it was last year and I went on um that entrepreneur winning women thing we built a business so we had an idea i think someone started it was like a menopause snack was the random idea or something and so you started in you started in chat gpt and you were like where basically you got to where i think at the problem at the problem we were sold we start with a problem which is menopause like products people with menopause and then and then you use chat gpt to generate data and find like a gap in the market and then help you get to a brand and then I used mid-journey to create some uh a brand packaging so you kind of have brand images and then there was another app that I've forgotten the name of but basically it created a soundtrack so like for an advert and so they you use like four or five different things basically to build a whole product but it's quite it was quite a good way I could imagine a team meeting where you ever you all started with the same problem and you said like using AI only in an hour create a product package it launch a product to solve a problem and obviously it's a mythical product but it's more the skill that you create you know being released in that way the skills that you have to use to get something started yeah it's a good point I think probably you need like a user case right to you could just try and build something but I had actually got a couple of things in mind that are ideas that you and I have had for ages where we've always been a bit like oh it's like a bit it's a bit difficult to make happen or we're not sure how we would do that or we've perhaps tried to outsource it you know to other people thinking oh other people do a better job of this and for whatever reason that's just not happened and so I thought I wonder if like we could just do it like even like if I was like if you could do a basic version for people to build on you could get people experimenting with it worst case you learn best case people actually use it yeah so I think probably I need to challenge myself that it needs to I probably won't do it unless I build it where it will be used so even if I was like I share it with the squiggly career community they use it for one week and then we go oh there are 10 things wrong with this but you know like I've I've actually done something that I could share with other people otherwise I think it'll always feel like a nice to do rather than a need to do yeah ah what are um well the first one you're not going to like about mine I just know you're not going to like it's just not very Sarah but I feel like I'm finding it really helpful so I'm calling it like parallel learning um so it's the whole like I guess it's just habit stacking but it's specifically with learning so it's finding things that I just do regularly where I could add learning in at the same time so the what has basically really helped me here is the peloton I mean I've obviously got to the Peloton in every single episode but it's because I do Peloton regularly and normally like honestly for the past like four years of Peloton I just press the Peloton program that they have and I watch somebody talking who tells me how I can make my life better by you know running a bit faster or whatever but I've I've I've worked through my favorite Peloton instructors and I was getting a bit bored so I've now just started listening to podcasts whilst I'm Peloton I'm like why have I not done this I'm Pelotoning I couldn't because I used to listen to podcasts when I was commuting to Microsoft.

15:02That was my time. And that was like four hours a week, if not more, when I could listen to podcasts. And I've completely lost that. And I haven't really found a way to fit it in that doesn't feel like it's in conflict with other things I'm trying to do. You know, oh, well, I've got to be with kids or I've got to do some work or whatever. I haven't found a place. And I actually think maybe there are more places. So there's a Peloton for a start. That's like two and a half hours a week now. Maybe two, because I still like a little bit of music. I still like it.

15:31Helen:Yeah, I was like, I take the joy of it away. I still like a little bit of self-improvement chat. You know, like the, you can do it. I'm like, yes, you can. AI is very good at that. All the AIs are like overtly positive, aren't they? It's like, that is a fantastic question. I'm like, oh, God. So I still like a little bit of that. But like, two hours a week that I can now, so I'm going through loads of, I listen to all of Emma Greed's podcasts. It's a very good podcast. I like that a lot. I like Emma Greed. And I'm now doing another one. what is it called um I've forgotten but it's one I don't think it's not a Sarah podcast but it's a bit cheesy but I'm learning quite a lot on it anyway so I was thinking there must be more moments in my week when if I think about it consciously I could do a little bit of parallel learning like every week for example I spend half an hour cleaning out rabbit poo from a every week half an hour that is half an hour that I could maybe listen to an audiobook or I don't know I could probably watch i just think there are moments when i could do some parallel learning with i just i've just got out of the habit of using those moments and what i'm probably doing is i'm on peloton i've just got into a different habit that's maybe not quite as helpful or i'm scrolling or whatever it is else i'm doing and it makes me feel really good when i've done it i'm like oh i've got another i've got another idea and i can share that with somebody and it just sparks me much more to use that time for learning and I don't have to find more time I just have to re-look at the time that I'm using yeah and so I want to find more moments like that more like why wouldn't I like that idea because it's too efficiency based yeah it's like efficiently using your time isn't it but um I mean the other day Helen you left me a voice note either mid peloton or post peloton where you could barely breathe so I mean it's hardly a surprise i was like right i'm gonna i was actually watching a youtube video at the same time but i paused my youtube video and then i went back to the youtube video you know that section that we've got in our new book about um single task time yeah this is not that but i'm going to start doing more of that one more time a week that i could do that and my second thing is i am going to just for the rest of the year just that's all it's not a forever thing but for the rest of the year I am going to have a monthly mentor moment so I'm going to have a time because I feel like I've really just not thought intentionally about what I would like to get mentored on and who could be the best mentor for me and this is not this is one conversation so it is not it is just me identifying do you know what I could do with learning a little bit more about this thing who's got the knowledge that I need I'm just going to set up a conversation with them and I just thought between September to December if I just do one of those I think it would just give me a little bit of helpful boost slightly different perspective and I really haven't intentionally thought about mentoring in a while and I thought it just it just just it's just I feel like it's an achievable an achievable goal to go after we often talk about the difference between you know in the moment mentors and then perhaps some mentors who stick with you beyond a conversation so it sounds like what you're aiming for is like just some in the moment mentors like what do I need to learn who can help me yeah I was thinking like Simon Alexander Ong who's been on our podcast before has written a good book called energize he's like his youtube channel's growing really quickly and I thought you know what I will I will go and have a chat with him about how he's done it and what he's learned by it there are other people like obviously you know new book coming out um I was thinking I might chat to people who've launched a book in the last six months and just ask them particularly in America which is a new market for us for like a book launch I might just put that conversation in a diary so I'm just gonna it's just to the end of the year because I think if you try and do this stuff forever sometimes you lose energy but it's like you know five conversations I just need to get in the diary so that's my other stuff nice we'll be able to review these things that Christmas Christmas party special um yeah so my theme I got a theme for my stops is it about Helen was that one of yours yeah my theme about stopping Helen um no my theme for stopping um was actually so the word I kind of had a word and then in two different ways my word is waiting okay so in two very very different ways and in some ways they might even sound contradictory I don't know so I'll say them both and see see what you think but the first one is I sometimes wait for too long to respond to people because I am waiting to find the right moment to do a good job to maybe give something I think thought but more thought that it actually needs and so then that lack of responsiveness actually causes me problems because it plays on my mind that I've not responded um I then feel bad I feel guilty because then I'm like I'm going back to somebody later than I wanted to and a lot of the time I think that if I think about those it's typically emails where I'm like oh those people are waiting they're waiting for me I could very quickly usually same day or next day at least acknowledge go back and say if you know so let's say I'm in a really kind of busy week and it's maybe not the right time to respond in a more thoughtful way I could go back and still say oh thanks that's really useful just wanted to let you know I've read it in the middle of a super busy week but I actually also I've got some more thoughts I'm going to come back to you with or whatever it might be um and I think that would make me more efficient and kind of more effective and I tested it today so there were two emails in my inbox and they weren't sort of urgent I don't don't imagine either these people were like waiting for me to respond but I wanted to respond to both of them so both of the people were squiggly career supporters and sponsors they both emailed me with some like feedback on one of them actually had done some of our learning and how much she'd enjoyed it and why and this other lady also called Sarah was talking to me a bit about some AI and ideas like again really kind of thoughtful really useful so obviously you could just not respond but I was like I would never I would never want to do that and then when I responded today I was like I'm just going to test out my theory of could I respond to each of these in less than five minutes is it more of like you know a David Allen two minute task or actually is it as big as I'm imagining because in my head I'm like this is like I need at least half an hour to like do this properly to like think through what I want to say and I did both of them in under five minutes oh so combined time yeah yeah so um I was like I don't know what I've been waiting for but all it's done is kind of created a cascade of wasted energy effort guilt like not usually um and it's also because it's it's slightly you know sometimes you have to push against your natural personality and I think that is a good thing I I don't think you can use your personality as an excuse to not get better.

22:42Helen:You know, that whole thing of like, obviously, we don't want to do something that's too far away from who we are. But do I think that's something that I could just be like, when I see something like that, at least go back to it, even if it's like a for now rather than all of all of the answers. But I suspect most time I could just do it. How will you know if not waiting is working? Because I would have less emails flagged in my inbox. okay because i flag them okay i just and i can i and some are flagged but not a flag because i don't know i just need to go back to the information but some are flagged because i want to respond and i reckon i always have this cluster of red flag responses which are not oh a client needs something because obviously as a team we would have gone back to those but they are people just emailing asking a question or with an idea or with some feedback it's those ones um and so yeah that would be that's my first waiting one okay yes my other one um which is sort of like I say sort of the opposite of that is knowing in an evening that pretty much 99 % of what we do can wait to the next day and so I can leave my phone behind and what I get stuck in is in the week I get so into the work that we do I sort of end up and particularly this is when I'm at home and actually even probably when I get home if I've been out for the day I always carry my phone with me from room to room always I'm like and and like I'd carry even if I'm not looking at it it's always kind of relatively close by even though I don't I'm quite militant about like notifications regular listeners will know um I'm carrying into like focus so I have no notifications popping up or anything like that but I definitely would still let's say I went downstairs and my little boy's watching I don't know how to train a dragon again and I'm a bit like he's not even interested in me and then I might be like I'll just take a quick look at my emails and then straight away you know like you've got distracted you're not present like or whatever and I think what he would probably quite like me to do is sit and watch how to train a dragon for the millionth time with him he wants me he wants to tell me what's going to happen before it happens because he's seen it before I have also seen it before but sure and I don't think that is like I think I will feel better about how I am showing up I don't reckon there's any upside you know like it's it's never like an urgent I'm never like really adding value and on the odd occasion where I might need to look at something for the next day that's always something where I need to kind of go back to where I work anyway so I could leave my phone there or I could leave my phone in the bedroom so it will make me I think the thing I was really trying to think I hold myself to account for this I was really trying to think through how I'd feel about doing it I think the thing I'd find hardest would be me and you because you know what this is so funny because i nearly put this one on my list so it didn't make my list for that reason because i thought oh it'd be healthier if we didn't if we had a little cut off point and i was like oh but that's just not how we work and so that just wouldn't work i would feel like i was letting you down if you needed me to respond to something and i didn't respond so i reckon if this because this is major list it didn't make mine because i two other things but i did think about it but i think we would need to have something between us that you know that we could like so i could protect that for you if that's if that's the thing you want to stop i think i'm probably the moment your biggest challenge but i guess it would just be i think what would feel weird is you and i are very like immediate about whatsapp so we just be like whatsapp whatsapp whatsapp like all the time for two weeks and see like oh my god no even I can't imagine well don't let's maybe do my version first and then let's work out I'm trying to work out how we would run our business without whatsapp but um I'm sure it's possible but I do think I think I will find it really hard um but I also think maybe it'll also give me more time I'd rather my eight-year-old see me read a book or an article than I would be on my phone the whole time because I'm like you learn by what you see in role modeling and he's getting to the age now where I'm like you know he notices that he will know he notices kind of what we what we do um and I remember talking to Zoe Blakeney recently we in one of our LinkedIn lives and she said basically you need 10 minutes of being really present like as a minimum every day and I was like oh I think I do that already but I definitely have moments where I'm I'm half I'm half and half I'm half listening to the how to train a dragon pricey and I'm half thinking what's that email I've just had through or that team's message um and I think it would be good for me and good good to good to try but I think I'll miss you well is this you like you're you're breaking up with me between the hours of like seven and ten yeah basically then probably I'll get to my phone at ten o 'clock I'll be like ah um yes well we should you should let me know what you need me to do that might be just don't message me between that time or just expect a response i suppose yeah yeah maybe that's it um okay so my stops then my two are stop writing actions on post-its actions post-its so this is a very specific thing so i'm at my desk this is this is only going to benefit anybody who's watching this on YouTube but I'm at my desk and I have a lot of post-its on my desk like I literally have well I've got these ones and just just in terms of the doctor these ones these ones I also have some large extra large ones these are some post-its everywhere the problem with having post-its everywhere is when I'm like if I'm having a meeting with you and I make a note it goes on a post-it and then I get really confused and I have like multiple actions all over the place and I find it really stressy and really messy stressy and messy because then they all go in my bag and I think well that doesn't look professional when I rock up and I've got like random bits of paper this also has led to some mistake moments because I've accidentally done certain things as a result of my messy stressy notes so I'm not going to do it so I'm allowed to write notes like I just wrote an idea that we were talking about which made a good podcast good um social post I'm allowed to do that but actions go in the file of facts she's got it I knew where we were going with this so no actions will go on a post-it note actions only belong in the file of facts I also was on holiday with some friends last week um and I meant to talk to him about it but I thought it probably wasn't holiday chat but he did bring out like a book every day with like a bullet journal thing going on like bullets and I was like I was like oh what's what's your code but I thought it was an appropriate holiday chat for me to like geek out on his bullet journaling code but and he was doing his own based on reading something then he was bulleting or just his own bullets like organizing his organizing time and planning things he got his laptop out and then he got a diet and there was definitely like bullet thing i was like oh i thought that was not holiday i thought how bound is that i was like that's not holiday chat but it will be next time i see him but i might need a bit of that going on so they stay organized here but at least they're in one place so my first stop is stop writing actions on post-it notes so if you see we need to say to you yeah so that actually needs to go in your file of facts yes put the post-it note down helen and put it in your file of fact and you can secretly have a little look in my bag and if you see lots of yellow bits of paper in your bag you know i'm failing and you can you can hold me to account you're still you're going to use them for like ideas and stuff though right that's fine but that's that's fine like that's that's okay it's the actions that are problematic because okay then it all gets a bit messy so that's my first one my second stop is to stop moaning about mondays it's monday what about today sarah i'm recording this in august and this is for september so it's fine because i'm gonna do actions in august that will stop me moaning about mondays from september onwards so in order to do that we have to reflect on why am I moaning about Mondays because I have too many back-to-back meetings and there's no time to like get my thoughts together and so it's a bad it's a bad start to the week also my Mondays are going to get harder from September because I my I've got a change in child care which means I now need to do the drop-offs every morning on a Monday so I do there is a bit of a like forcing function as well for me to make my mondays a bit better um so there are a few things i need to change there are a few people that i need to talk to to work out how we protect mondays but that is i want to feel better about mondays because then i think i bring that energy into my week and i don't like moaning i'm not a moaner i don't want to start my week i think it's also not a great way just to start is it it's not a great way to like start a week to be like it's not really good to inspire your team moaning about i'm fed up a moan i'm bored of moaning like no more moaning about mondays so yeah maybe you've got to do that you know that great phrase your diary doesn't lie you know that we that we both kind of come back to maybe you have got to do the whole start from scratch thing on your mondays because i feel like this is a recurring red flag more for you actually than for me because you do more more team stuff on a monday than i do so like we talked about it loads i think we have incrementally tried to tweak for you together and kind of none of that has quite worked so if you I think you've almost kind of got to go right if I was starting from scratch on a Monday blank you know like the Shopify thing of where they took all meetings out for two weeks I think you've got to take the Shopify approach to Mondays and you've just got to go completely clear and then you you kind of you know the whole maybe you maybe oh this this maybe you have two weeks your first two mondays in september if this was even possible might be too late for this now you know like i'm thinking two clear mondays you know like you go i'm gonna do two no meeting mondays i'm gonna do nothing on a monday other than perfect monday because i do love our team meeting on a monday no i know but maybe what i'm saying is maybe you have to start from that though to then be able to go maybe the team meeting could still make the cuts because that's our idea i don't need to go cold turkey with meetings but i do need to i do think i would be very good i think to have an as is and a to be and then yeah that's a good idea yeah that with you and people in the team that influence that and i and say i will be better because of having the to be version of my monday like please help me to make this happen that's my that'll be my that will be my ask but I think people can only help me if I if I think if I present that as is and to be picture for them yeah and I guess there'll also be inevitably with any of those kind of time trade-offs there'll be those crunchy moments where it's like well if you want to if you want your Monday to look like this this is something you're going to have to say no to or not yet to or you know like those kind of the which always feels hard right but I guess it's probably that it'll feel hard in the moment but it will feel helpful when that Monday comes I think that's sometimes what I try to remember with the work that we do because I think I could work all day every day and still have more that I would want to do in what we do because I always think oh but that would be useful or we could help more people if we did this but I think I always go back to but I still want to be helping people next year and in five years time and in 10 years time I've forgotten what the research is but you know the the research about how like basically like how present biased people are so you ask and I'm like yes sure we're not very good at protecting our future self so yeah the the Helen at the end of September on a Monday right I'm not very good at protecting that Helen like because I'm more like oh yeah I'll do that now I'll do that now now yeah where we kind of have to like think about the kind of being kind to the future version of us and what we want that that what we want that person's monday to look like not necessarily how you're feeling right now about it because i might be like right now it was end of monday i could do it again i could i've done this one i could do it again whereas actually no it doesn't feel like that when you're in it um so i wonder whether what do you think we should as a little bit of accountability we should put a meeting in at the like first of october just as a little checking because i don't could you leave it to the end of the year it's too late but we could do like just put a little diary meeting we don't even have to have the meeting but i could just put a note in our diary with our start and stops in just as a little account like accountability moment to go oh have we done the things we wanted to start and the things we wanted to stop i suppose what we what we could do talking about um your habit stacking thing is we have a win watch every quarter so uh on our next wind watch which will be that'll be a kind of our that'll start in kind of September October time we could put this on our wind watch like how are we doing with our September starts and stops because that is something we already use to review how we're doing and also we both look at it enough that you like it would remind us oh actually I'm still whatsapping Helen 15 times every evening that's probably a conservative estimate or like you know and I think often those things the accountability things I think can sound a bit daunting or a bit intimidating but I think the purpose of them really is just is noticing it's like noticing what's not working is it because that start and stop was too ambitious is it because you need more help from someone do you need to think about it in a different way I don't think it's designed to beat yourself up it's just to like just to learn so I think this conversation is useful hopefully for two two things one for your own reflection but also for your awareness of what other people want to start and stop and how you can support each other so we mentioned at the start about doing this as a team but we will definitely be doing this with our team so we know what they want to start and stop and we would highly recommend that you do this as a team activity I'd probably say give people the heads up beforehand just to say this point earlier of the stops in particular took a little bit more time maybe just say oh we're gonna you can always get them to listen to the podcast if you want to but we're going to do this exercise as a team everybody's got five minutes to share their one start and one stop um and ask for any support that you might need and then we'll kind of all go around so maybe just prep people so that feels like a like not a pressured not a pressured kind of thing for them to do but we hope you found that episode useful let us know uh you can get in touch with us at helen and sarah at squigglycareers.com if you've given it a go if you want to share your september starts and stops um if you've got ideas for other episodes um we have I've got quite a big back catalogue, which I know sometimes actually can feel a bit overwhelming.

37:25Helen:But there are loads of ways that you can search through the podcast for what you need. You can do it on the website. There's search functionality. I use an app called Overcast, which is just really good for searching, really quick and easy. And AI is your friend. I've now started using Claude to search our own podcast for episodes we've done to make sure that our no repeat guarantee continues. We should create. That could be one of our, your little create from scratch. a squiggly searcher. And we could put all of our episodes in and a squiggly searcher will help you find the right recommendations.

37:57Helen:That's a good one. You know, like there's, it used to be in the old world, there's an app for that. Now there is actually a website called, there's an AI for that. And maybe we could have an equivalent of like, there's something in squiggly careers for that. Career conversations, interview, getting a promotion. There's a squiggly career. I need a better name. I need a better name. Okay, we'll get there. We'll get there. But it's a nice idea. And everyone, do not forget to sign up for the sprint. it starts on the 15th of september go to squiggly sprint.com sign up it is free and get involved thank you so much for listening and back to you again next week bye for now everyone

From the publisher

🥇 Sign up for the sprint here: https://bit.ly/41jasYO


Are old habits holding you back from the progress you want to make? September often feels like a natural reset point—a chance to stop what’s no longer serving you and start building new wins. In this episode, Helen and Sarah share their own September “starts” and “stops” to inspire you to reflect, reset, and refocus. You’ll hear how small, intentional changes can help you create space for growth, protect your future self, and build habits that last beyond the September spark.


⏱️ Timestamps


00:00 Announcement

01:02 Introduction

03:45 Why September feels like a reset moment

07:18 The power of starts and stops

10:35 Weekly Borrowed Brilliance

15:40 Building from scratch with AI

21:58 Parallel learning (habit stacking with podcasts)

26:45 Monthly mentor moments

32:30 Responding quicker instead of waiting

36:55 Leaving the phone behind in the evenings

41:48 No more post-it actions

44:55 Stop moaning about Mondays

48:20 How to use this as a team activity

52:00 Wrapping up & accountability


🎯 What You’ll Learn


  • Why September is such a powerful time to reset and refocus
  • How to identify habits that are helping—or holding—you back
  • Practical ways to design new starts that spark motivation
  • How to stop habits that drain your energy and confidence
  • Why sharing starts and stops as a team builds connection and support


📚 Resources Mentioned


How to Change by Katy Milkman (for the “fresh start effect”)


For questions about Squiggly Careers or to share feedback, please email helenandsarah@squigglycareers.com


More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

🏃‍♀️ Join our next Skills Sprint: https://bit.ly/skillssprint2024

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/


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