Career Plans and Parenthood Pivots with Emily O'Brien

“People come to me with problems that I have myself, and I find it so easy to coach them out of it. But then as soon as it comes to myself, there is definitely a barrier there. But there's a great quote that I really like that is, 'You can't see the label when you're inside the jar.'“ - Emily O’Brien

[00:00:05.340] - Lucy Critchley

Life is a series of chapters. Some we write and others are written for us. But what happens when we reach a turning point? Welcome to Untold Chapters with me, Lucy Critchley. In this podcast, we'll explore the real-life stories behind those pivotal moments, the heartbreaks, triumphs, and decisions that changed everything. These are the moments that are sent to challenge us, inspire us, and remind us that we're never alone.

[00:00:34.320] - Lucy Critchley

This week on Untold Chapters, I'm joined by Emily O'Brien, a brand strategist who had her sights set on becoming Yorkshire's answer to Don Draper. She was on track for a big promotion and about to transform her forever home until life had other plans. Finding out she was expecting identical twins meant big changes. A new house, a career shift, and a whole new way of looking at work and family. But in embracing the unexpected, Emily found joy in freelancing, the perfect place to raise her growing family and a life that, while a little chaotic, is exactly where she's meant to be.

[00:01:12.800] - Lucy Critchley

Hi, Emily. Thanks for joining me on the podcast today.

[00:01:15.880] - Emily O'Brien

Hi. Thank you for having me.

[00:01:17.550] - Lucy Critchley

My absolute pleasure. We've had some technical problems this morning, haven't we? So let's see how we get on on this recording. But to begin with, I have been asking all my guests to give us an overview of their Untold Chapter.

[00:01:31.430] - Emily O'Brien

I was working for a digital and brand agency, and when I went off on my maternity leave, the plan was to come back and train up to become the brand director, so responsible for brand strategy, tone of voice, messaging, and overseeing brand campaign delivery. And I kind of foresaw myself as being like this female Don Draper. That was my career goal. And whilst on maternity leave, COVID happened, the brand sector of the agency ended up kind of making redundancies. I still went back, but in more of a project manager role.

[00:02:08.740] - Emily O'Brien

And then I had another pregnancy, which surprised us with being twins. And that was very soon after my first pregnancy in that my daughter was still one when I gave birth to the twins. And so I had three kids under two and the childcare situation here. And to be honest, the living situation as well because we didn't plan for having three kids, so our house was not appropriate. Meant that we just need to move house, move home, move close to my family, give up my job at the agency and become self-employed so that I could try and build a business around having the twins at home because there was just no financial capability of putting them into childcare and then travelling to a job and working in an office or even hybrid working and having that rigid hour structure.

[00:03:04.650] - Emily O'Brien

So yes, that's my sort of untold chapter in a nutshell of not really quite going Don Draper and instead working around nap times and kids trying to freelance.

[00:03:17.710] - Lucy Critchley

I can only imagine the juggle. I've got one and that's a juggle enough sometimes. So dealing with three times nursery fees and stuff, it's just cost prohibitive, isn't it?

[00:03:33.010] - Emily O'Brien

It was just-, yeah, it was crackers. We're lucky in that we're Yorkshire-based, so I don't even know how I would start down in some of the more expensive cities for childcare. And we are lucky in that one of our childcare settings provides a sibling discount, so that made it a bit more feasible as well.

[00:03:53.800] - Lucy Critchley

Oh, nice.

[00:03:53.840] - Emily O'Brien

But yeah, we've got a real juggle in that we've got one child who went to one nursery, and then the twins went to a different nursery because we live in a village now and there isn't actually the provision for three kids of a similar age to all go to the same childcare setting. There just weren't spaces. So it was very much just scatter approach, the kids and then do like a-, to wrap off and then round them up at the end of the day.

[00:04:20.190] - Lucy Critchley

Yeah. Oh, wow. So does your eldest start school in September?

[00:04:24.790] - Emily O'Brien

She and I both cannot wait.

[00:04:30.580] - Lucy Critchley

Sounds like mine. My daughter starts in September. And she's very excited to go, but is also aware that she won't go to preschool anymore. That's been quite a big, like, realisation, that, 'Oh, I'm not going to be going to see my friends at preschool.'

[00:04:50.380] - Emily O'Brien

Are they different friends that will go to school?

[00:04:52.930] - Lucy Critchley

They're not going to the same school, no.

[00:04:54.600] - Emily O'Brien

Oh, that's tough. My daughter is quite okay in that she's just moving straight from nursery to school with the same kids, so it's not too bad. And she's already left as well. So we've got proper summer holiday juggle before she starts school.

[00:05:10.410] - Lucy Critchley

Oh, wow.

[00:05:10.630] - Emily O'Brien

But that's quite nice because she's already kind of had that leaving time to recover from it before starting. But yeah, and then childcare funding starts for us in September as well. So this next year is just a lot easier for being able to have more of a routine, more financial stability.

[00:05:32.540] - Lucy Critchley

Yeah, yeah, definitely. Oh, amazing. And I'm curious to know when you were working in agency life before your lovely kids were born, what sort of work were you doing? What sectors were you working in? What were your clients like? What did you enjoy the most?

[00:05:51.300] - Emily O'Brien

So the agency didn't have a particular niche when I first started. When I moved into the agency side, because I used to be based in client businesses I worked in-house. And then when I moved to the agency, they were just really starting, and I helped them set up the comms team. So I was responsible for all of copy, social content, any form of content, any form of word went through me from that agency. And then I merged into the brand strategy after a few years, but started to specialise in healthcare, education, property, and charities. They were the kind of four main areas. I came from a charity background, so I had a lot of experience in that side, which is what I'm now focusing on.

[00:06:39.160] - Lucy Critchley

Yes, I was going to say we have a sort of-, I was going to say a client in common, but a sector almost in common in a client that you have in and related one that I have. And I was wondering what the sort of origins of working in that world, where did that come from, working in charities?

[00:06:54.420] - Emily O'Brien

My first job, proper, you know, salaried full-time job, was a receptionist for a health policy think tank down in London. So I just needed a job to fund my Masters. I was doing a Masters in Health Promotion at King's College London, and I just needed a full-time job to be able to pay for that and live London. So I got a receptionist job, but it was for a think tank that was in health care.

[00:07:21.400] - Emily O'Brien

And we were responsible for the Ofsted rating review of hospitals that's now the CQC rating. So they did the work around that, that type of thing. So it wasn't a charity, but it was not for profit, and it was all about the policy and science behind health care. And I really enjoyed that. I did that for about four years, and then I moved into Cancer Research UK in their statistics team. So that was the move from not for profit think tank straight into charities.

[00:07:51.340] - Emily O'Brien

And I was there for a while until I came out of charity sector, worked for a health technology sales and marketing kind of role. I didn't really enjoy being out of that sector and then actually got poached by their agency to head up their comms team.

[00:08:07.110] - Emily O'Brien

So that's how I got into the agency. It was the agent, I was their client. So it's nice to then come back to the charity sector now and start using those skills again, because it's totally different sort of charity comms to sales and marketing. It's obviously a different skill and I much prefer that side.

[00:08:28.000] - Lucy Critchley

So the agency that you worked in up north, when did you move back up from London?

[00:08:33.910] - Emily O'Brien

Yes. So the agency I worked in was based in York. I moved from Cancer Research up to York, and that's where I got the sales and marketing job. That was 2015. I just got tired of London. I'm not from London, I'm from Yorkshire, as you can probably tell. And I went down to study, and then I got a job, stayed in the job, met my now husband, stayed down there for work and relationship. And I just got to a point where I was just like, I just need to get out now. I'm just tired of being down there. So yeah, it was 2015, moved up for my career. Weirdly, coming out of charity sector meant that actually I was able to get a promotion. And then, yeah, that's how I ended up working for a northern agency.

[00:09:21.100] - Lucy Critchley

Amazing. I moved to London after uni with my boyfriend at the time, who is now my husband. We'd just got engaged in-, I get this wrong, 2015, we got engaged. And it was that. I always get mixed up because we moved on a New Year's Eve and I always get mixed up, whether it's 15 into 16 or 14 into 15, but I'm pretty sure it was 15 into 16.

[00:09:50.280] - Emily O'Brien

That sounds like a chaotic New Year's Eve plan.

[00:09:53.300] - Lucy Critchley

Yeah, it was. But you know what? It was actually amazing. We packed up our flat. We lived in North London in a place called Winchmore Hill, which was near Southgate on the tube. And we loved it. We had a beautiful flat that we obviously rented, we're not owning any property in London. And the realisation that we probably wouldn't be able to afford to buy anywhere in London, and that both of our families were in the north was just quite a big pull for us to leave.

[00:10:26.060] - Lucy Critchley

And he was freelance, and I was thinking about going freelance. And then I found a job working on a TV show that was filming in Cheshire. So I got the job and that's what pulled us out of London. And then a friend who worked in TV pointed me at a production company in Leeds. So I can really relate to that, like, needing to get out and make that move. I had a great experience living in London, but the lifestyle was probably not conducive to, like-, for me, anyway, the rest of my 20s and 30s and beyond. I can't imagine being there now, if that makes sense, with a kid, and-,

[00:11:10.940] - Emily O'Brien

Yeah, yeah, it sounds similar. We wanted to buy a house, settle down, have a family. We got engaged whilst we were still in London, and we kept moving further and further out. So we ended up sort of Lewisham, and that's when we decided to get a little run-down car so that we could get out at the weekend easily.

[00:11:32.930] - Emily O'Brien

But I was just tired of the commuting, tired of the crowds, tired of the expense as well. Again, working in the charity sector, funnily enough, I wasn't on a staggering salary, and I was also still paying off my Masters degree as well. So it was-, I was just counting down to payday all the time, and it was just not really the way I wanted to live. And then coming back up north, we lived in a very-, it was like, I think someone described it to me as this chocolate box picturesque cottage near Newmillardam Country Park. And it was a terraced Yorkshire stone cottage. It was tiny, but it had a garden. It was next to a pub. It was brilliant. And it was a total gear shift from where we were at. But just-, my soul just felt so much happier there. It's just-, that's my kind of vibe.

[00:12:28.290] - Lucy Critchley

That's it. And that's really important to find what that is, isn't it? We moved to Chapel Allerton in Leeds, and we rented a three bedroom house with a driveway and a garden, and it cost £200 less a month than our one bedroom flat in London cost to rent. It was crazy. And it was-, you know, just a different speed of life, I suppose.

[00:12:51.250] - Lucy Critchley

I like going back to visit, and I like to go and see some friends that are still there and you know, all that kind of thing. But the thought of that being my life-, at first I struggled with-, I don't know. Leeds is a very good place for, like, everything's really convenient, but London is just another level, isn't it? I definitely struggled with, like, public transport and like, you know, all that kind of thing. But I much prefer this. Even in a city, it's a slower pace of life. It makes all the difference.

[00:13:22.130] - Emily O'Brien

Yeah, yeah, it does. I mean, we took it to the extreme, moving to this remote village, because we couldn't even walk to get a bottle of milk. If we ran out of milk, we had to get in the car. And there wasn't really any public transport. But I think it just made us a lot more conscious of-, you've got to plan everything and buy in advance. And then that saved us money as well because we couldn't just walk to a corner shop and get your dinner that night. You had to plan it. And when we had a mortgage to save up for, a wedding to plan and save for, it was so easy to save up when you'd been used to living the London way.

[00:14:02.020] - Lucy Critchley

Yeah, that's it. You're not doing that kind of pub after work every night.

[00:14:08.160] - Emily O'Brien

I do miss that bit.

[00:14:09.880] - Lucy Critchley

It was pretty nice. So you made this big shift and you moved from London and you were working for the agency in York, had your babies, and then decided to set up your own business. So do you want to tell us about your business and what you do and who you do it for?

[00:14:33.790] - Emily O'Brien

Yeah, sure. So when I first set up, as I say, I was working around the twins' nap times, and I was getting up really early and working before my husband started work, and then I was working late after he finished into the night. So I wanted to initially do a freelancing service that would be kind of asynchronous. I could do around any time without needing to be present for calls and things like that.

[00:14:58.080] - Emily O'Brien

So I just went straight into copywriting which was obviously my experience from the agency, and it's what I was doing in-house for the charities and for the healthcare company as well. It's not particularly my passion, I say, gesturing loudly, like a lot of copywriters have. I like writing blogs and website content, but it's more the meaning and the reasoning behind the copy and why you're talking that way that I've really enjoyed, but I really couldn't get into that without having capacity during working hours to be able to do workshops and to really get stuck into things.

[00:15:35.290] - Emily O'Brien

So it took a good six months or so for me to start turning over a decent enough income to be able to justify sending the twins to a childminder. So I went straight for a childminder because that's a bit more affordable. She came up with a bit of a deal. I can't remember exactly what it was, 10% off or something like that. But it was basically-, she was like, 'You didn't pick to have twins. It happened to you. So you can't be expected to pay double for childcare.' So that was quite nice.

[00:15:59.830] - Emily O'Brien

So it was a really good sort of stepping stone for being able to pay for more formal childcare. And I was able to then start offering-, I started doing content strategy. And I think because I'd had such a big time out from the agency with COVID and then being sort of more admin behind the scenes, and then I got furloughed whilst I was pregnant with the twins because that was a rocky pregnancy, that I just had real imposter syndrome about offering brand strategy.

[00:16:27.270] - Emily O'Brien

So I ended up, I did the Chartered Institute of Marketing Brand Strategy course. I did Sarah Robbs' Brand Strategy Academy. I just used a lot of my time to keep soaking up brand strategy learnings whilst continuing in content strategy because content strategy is just what I've always done.

[00:16:44.720] - Emily O'Brien

And then I relaunched my brand and content strategy/project management services, January of this year, so January 2024. I used to be called Content by Emily because that was what everything I did, content. But now I wanted to do the brand and project management stuff. It's now Folly, which I thought I'd go for a slightly fun name so that I can do different services because Content by Emily, a lot of it felt jarring to me. Content, obviously, was what I did initially, so that started to feel jarring with offering brand and project management.

[00:17:21.950] - Emily O'Brien

But I also felt not quite right because I work very collaboratively. And actually, a lot of the stuff that we come to at the end of a project isn't all by me. It's facilitated by me, it's coached by me. But it's not-, it didn't feel right. It's not the process that I worked by. And then, yeah, Emily's fine, it was me. But it just didn't feel like all of those words really felt right for how I worked. So Folly as well, it kind of means something without purpose. It's a bit of frivolity. And quite a lot of my businesses need help defining their purpose and then delivering that definition of their purpose. So brand strategy is quite often creating and coaching out of them what the reason for their business is, why they do what they do and what their story is.

[00:18:14.120] - Emily O'Brien

So it felt quite relevant, the name. And the project management service that I do alongside it is because, again, that's what I did throughout the agency. It's coming up with strategy and then actually managing the delivery of it. And it's a nice way of building that long term relationship with clients, so I can do the strategy for you, but then I can either help project manage it or do the delivery of everything that's in that strategy.

[00:18:38.620] - Emily O'Brien

So that's what I've currently been doing. But yeah, it's mostly been for not-for-profit charities or impact-driven businesses. So it's not about you not making a profit. That's not why I won't work with you. It's more about what is your story? What change are you trying to make with the world? It sounds really grand. But yeah, so there's been sort of education, there's been policy again. I'm currently about to start working with a recruitment agency, but that's again about sort of reviving the recruitment industry and making it a bit more fun, which I've bought into for that reason.

[00:19:15.620] - Lucy Critchley

Amazing. And as someone who's-, personally, I've had a few jobs via recruiters, and I've always found the ones that I've worked with very engaging and friendly and interested. Obviously, I know that that's an element of the job that they're there to do. But then it's got to be the right fit, hasn't it, with a recruiter, industry and sector as well as person to person. And I think that that's a really interesting equivalent in the sort of work that we do. The client side of things has got to be a good fit, hasn't it?

[00:19:48.250] - Emily O'Brien

Yeah, it's all about relationships, isn't it? At the end of the day, making sure that values and everything match. So yeah, there's a lot of matches there.

[00:19:57.650] - Lucy Critchley

Yeah, yeah, absolutely. So now, your twins are with a childminder, presumably at the moment, not right now, but like, generally. And your oldest is going to start school and all the rest of it. So what will September look like? I know you mentioned that they've got nursery.

[00:20:14.250] - Emily O'Brien

Yeah, so the childminder, we stopped using the childminder about a year ago. I think it was last summer because I started to get bigger projects which needed more availability, more routine, whereas we were struggling a little bit with childminder, people get sick or there's not as much cover. There's not as much reliability with the childminder. So we did move them into a nursery last year and they're going to be there for the next year. So they're there for two days and then my parents have them for a day.

[00:20:46.600] - Emily O'Brien

So I have three days to work whilst Imogen's is at school. And it's so much easier knowing that there are set hours that I will definitely be able to work. I mean, obviously, there's sick days and all that kind of stuff. But yeah, generally, September is just looking a bit more available. I wouldn't say growth. I'm not particularly planning on taking on more time of work, if that makes sense, more client time.

[00:21:11.960] - Emily O'Brien

I haven't had much time to actually focus on me and my business in the last 12 months because every ounce of spare time has had to go to chargeable work. So I'm quite looking forward to having a little bit more flexibility with my own time, you know, do all of the marketing stuff that I tell other people to do.

[00:21:29.560] - Lucy Critchley

Yes, oh, my gosh. I can relate to that so so much. It's easier to work with other people to support them to do theirs, whereas your own, it's just a bit-, it goes by the wayside for me, personally.

[00:21:46.890] - Emily O'Brien

Definitely. Yeah. People come to me with problems that I have myself, and I find it so easy to coach them out of it. But then as soon as it comes to myself, there is definitely a barrier there. But there's a great quote that I really like that is, 'You can't see the label when you're inside the jar.' And I think even when you're a marketer or a coach or whatever you do, I think there's always a point where you need to tap into other people just for help. And it's not against your skills or it's not a downplay on what you can do for yourself.

[00:22:22.380] - Emily O'Brien

It's just when you're so absorbed in it yourself, to be able to take a step out and have a look at what you do and summarise it and do your own marketing, it's so hard. But yeah, I quite liked that quote that I found. I think it's definitely-,

[00:22:38.510] - Lucy Critchley

Yeah, that's a really good one. Yeah, and so true. So, so true. Oh, Emily, I've got two questions that I ask my guests as we come to the end of the recording, and I would love for you to answer them for me as well. First one is, looking back on this whole experience of working in third sector and working in agencies and now doing your own thing, raising a family, moving cities, like, one of those bits alone is quite a big thing. So when you add it all up, that's such a massive experience. I'd love to know what your biggest learning from it all, what's that for you?

[00:23:20.320] - Emily O'Brien

A big learning for me is to realise that you are always learning. And I know that that's a lot of the word of learning within a sentence, but it's understanding that there's always more growth that you can do. And every experience that comes your way is a learning experience. So terrible clients, just-, it happens to everybody. Don't see it as a negative on yourself, just learn from it and make it as positive as an experience as possible.

[00:23:51.710] - Emily O'Brien

And that's happened sort of throughout all of my jobs, I've learned something new. So I've gone from policy, I learned so much about how the country is governed, what goes into policies, about the research and the stats, which then I tucked into my next job. And it was then about how much stats can be manipulated by the user to really say whatever they want them to say. So you can't take a stat out of context with any meaning. And that was quite a good way of then rolling that out into my comms.

[00:24:28.570] - Emily O'Brien

And now the work that I'm doing now is just context, context, context. I think this is kind of two things in one, really, it's like, yeah, always learn, learn on the job. I absorb so much. I've always got a budget and time set aside for development still because there's always growth you can do. But then, yeah, always context, context, context as well, the stuff, if that makes sense.

[00:24:54.790] - Lucy Critchley

Yeah. And I think that context side of things is really important, isn't it? Because you can look at-, taking marketing, you can look at somebody's business on the internet, what they put out there, for example, and think, 'Oh, they've got it made. They've got it so sewn up,' as an example. But actually, when you get to know that person, they're just human like you are. And I think it helps unravel and make that context a bit clearer in your own mind. Does that make sense?

[00:25:23.730] - Emily O'Brien

Yeah, definitely. There's always a bigger story behind everything you see. And it's just-, appreciate that you can't see that story all the time. And also, if you are going to start using something, you need to read into it. And the onus is on you to understand how people got to that end stat, social graphic, whatever it is that you're going to start using. And I think that's more important as well now in a world of AI stuff is, again, just the onus is on you. If you're going to use stuff, you need to understand the story behind it and the work that's gone into it.

[00:25:57.010] - Lucy Critchley

Yeah, absolutely. And especially in this brand marketing content world, that's a really important reminder, isn't it?

[00:26:04.300] - Emily O'Brien

Yeah.

[00:26:04.840] - Lucy Critchley

Cool. And then my final question is, if you met somebody tomorrow that was due to have twins and was having this big life shift, what advice would you give them?

[00:26:18.720] - Emily O'Brien

So, yeah, the twins thing really was-, it was a big thing to get over, but I'd not change a thing. And I would say to anybody that's in the similar situation, if they just found out that are having twins, and they're probably reeling from it because it is quite a whammy. Just know that whatever life throws at you, you can handle it.

[00:26:39.490] - Emily O'Brien

You can split yourself in that way and be able to be a good mum. And all the girls are good big sister to both, like, there is enough of you to go around, but there is so much-, I had a coach at one point because I was struggling for quite a while while I had my-, setting up my business and dealing with the kids and having them home because I had so guilt around not doing anything well.

[00:27:02.460] - Emily O'Brien

There was a really good thing that she said that really sat with me, and I think I'd probably leave it to them as well, is just, like, there was so much data. When you're having twins or you're having a new life event like that, that is just-, it knocks you completely off kilter. Give yourself time to take in all of that new data, realign it, and come out with a plan.

[00:27:24.940] - Emily O'Brien

You can't just hit the ground running all the time and have a plan straight off the bat that's going to work well and you're mentally okay with it all. Give yourself space to not be okay, to take things slower, to drop balls, to have a cry. It's fine because in a year and a half or a year or so, all of that data will make sense to you now and you can just-, it'll just be your new way of life and it's fine. Whatever life throws at you, you will be fine. Just give yourself space.

[00:27:59.130] - Lucy Critchley

Oh, I love that, I love that. I think that's really, really important because even when we came home from-, I didn't have a great pregnancy with my daughter, and I know that you had a tricky time when you were pregnant with the twins. And that whole thing of like, 'Well, what do I do? Am I doing the right thing? Am I a good mum? Am I doing what I'm supposed to be doing? Does she like me?' There's big questions that you ask yourself.

[00:28:28.810] - Lucy Critchley

And I think, One, you've never done this before, so get yourself some slack. But then also for me, the thing that I kept coming back to was, I had had therapy at the time, and my therapist had said, 'The fact that you're worrying about doing a good job means that you are doing a good job, because if you didn't care, then that's just as big a thing, you know, of wanting to make sure that you are doing the right thing by your family, that you're looking after them and so on.' It doesn't strip away any of the guilt that we all feel and stuff. But I find it really useful to have that, as I'm sure you might have done with your coach, to have that external person who's just there for me to talk about it all.

[00:29:18.330] - Emily O'Brien

Definitely. I think that almost goes back to the jar and label quote again. Even if you feel like I don't need a therapist or I don't need it, it's so helpful just to have that time to talk to someone who can echo it back to you and help me make sense of just everything, all of the data. Yeah, she knew I worked in stats before, so she spoke my language.

[00:29:46.590] - Lucy Critchley

All of the data, absolutely, and that's it. I was going to say she's really nailed that analogy, hasn't she, that metaphor. Oh, thank you so much, Emily. It's been a pleasure to talk to you. And I know, obviously, as a podcast, people can't necessarily see this, but we're both wearing green stripy tops. So clearly, we're in good company today. I really appreciate you coming to talk to me and sharing so openly. Thank you very much.

[00:30:22.220] - Emily O'Brien

Thank you for having me. Thank you.

[00:30:25.970] - Lucy Critchley

Thank you so much for listening to this episode of Untold Chapters. I really hope you enjoyed it and found something that resonates with your own story. If you enjoyed this episode, please don't forget to rate, review, and follow us wherever you get your podcasts. Your support will help us share even more incredible stories. Untold Chapters is an Untold Creative production. Until next time.