How to overcome the big obstacles in your career

Everybody will come up against an obstacle in their career at some point or another, and the intimdating question of “How do I get over this?” can seem overwhelming.

Unfortunately, career obstacles occur much more frequently for professional women than men, and this can be either as a result of direct or indirect discrimination. A lot of the time it is unconscious bias, influenced by gender ‘norms’ that can lead to career-driven women feeling stuck in a position, feeling unheard or lacking confidence in senior positions.

It can be tough out there – in the workplace – and the more senior you get, and the more responsibilities you take on in your role, the more obstacles you’re likely to face with career progression. The glass ceiling still appears to be very real, even if slightly more and more subtle over the years…

To help us out with overcoming these career hurdles, career coaches and founders of Working Wonder, Calli Louis and Nichola Johnson-Marshall have answered our burning questions with amazing insight. With extensive corporate backgrounds, and by working with ambitious professional women as clients, Calli and Nichola are well-placed to teach us a thing or two about managing career challenges.

Calli Louis and Nichola Johnson-Marshall, founders of Working Wonder and career coaches.
Calli Louis and Nichola Johnson-Marshall, (left to right) founders of Working Wonder and career coaches.














Lauren: What are the common problems and the common obstacles that you see career women experience?

Nichola: “This is a really interesting question. I think, first of all, you default to what it is that’s just stopping women in themselves and and I think definitely confidence, and definitely impostor syndrome.

“I think that what’s key here is: it’s not women’s fault. It’s how the workplace has traditionally been structured so if you look at the time that work first started, it’s a very male dominated environment. And also, it’s a very white male dominated environment. I’m not saying that’s awful; I’m just saying that it is a systemic culture which has been created.

“I think that when you have been working in an environment where quite often you are a minority, and it hasn’t been adapted in terms of flexible working policies, remote working policies, adapting to the fact that you have other things going on in your life, then actually, then it is going to jar on your confidence and you start thinking that, ‘Oh, I don’t lead in that way, or I’m looking at a leader who isn’t like me and I don’t possess some of those traditionally masculine leadership traits.’

“You can see how mindset-wise, you really need to focus on keeping that positive mindset, because the environment in which you were trying to progress your career is really an environment that probably isn’t as inclusive as it should be. So, you know, you’ve got traditional workplace culture, you’ve got the masculine leadership traits. But they are evolving and they’re really changing. Leadership now is certainly looking at how more soft skills are important for leaders – empathy and kindness and things.”


Lauren: Do you think that lockdown has sped up that evolution towards soft skills?

Nichola: “Yeah it has. Also, I’d say that what’s interesting since lockdown is that companies have always had the technology to go remote – yet haven’t adopted it. I remember launching Skype when I went to eBay 15 years ago and people just didn’t really adopt video calls, and now all of a sudden – funnily enough when we have to – everyone can do it.

“I think that now lockdown has happened and people can work remotely, it’s actually going to blow up all of the traditional, you know, flexible working policies and the ‘Oh no, you can’t work remotely, you’ve physically got to be in this office.’

“I think that women’s career progression has been hindered by things that aren’t necessarily their fault and there are some things we really want to raise people’s self-awareness about.

“Why are you feeling unconfident? Why do you feel like an impostor? Is it because this belief is limiting you? Having that self-awareness is your secret weapon to then know how to deal with it, how to manage it moving forward. So, quite often when you look at women and women’s career progression, it’s put on the woman. And actually, we’re trying to say: some of these things really aren’t your fault. Just be more aware of it and learn what you can do to, you know, to arm yourself with the tools to be able to push yourself forward in your career in the environment in which you are in.”

Calli: “I think the mindset is definitely the biggest challenge, but I think it’s about that piece on working culture being naturally more male driven. It’s just having sight of those role models and if you don’t have them in your working environment, it’s: where do you go to get those role models?


Lauren: “OK, so there are some common problems that we see with women on an individual level, but then there are common problems that we see with kind of being the ‘minority’ in working culture. I think an appreciation – like you said – and awareness of the way things have been in the past and where they are moving towards, is a good step here.  

“What do you think when a woman says ‘I’m not very confident.’ Where do you think that comes from and how would you help her understand where that’s come from herself?”

Calli: “The good thing is that I actually think women are good at talking about this stuff much more so than men. It is not to say that men don’t have confidence issues, because I’m sure they do, it’s just women will naturally voice them more. They maybe bring more emotion to the workplace which, again, I think is a good thing. I think empathy and leadership is a brilliant marriage.

“Going to your question about the root cause… I wish I had known this when I was younger, and I think there’s this brilliant thing about the ‘4 phases of your career.’ It’s from a book by Avivah Wittenberg Cox.

“It’s basically that: women’s careers have different trajectories than men – not all women obviously but most women – and what happens in a typical man’s career is basically different.

“Women start in exactly the same place. Hopefully we get a job – you work hard, you work every hour God sends, you get a promotion, and the pattern repeats. Then you hopefully kind of have continuous success that is an uninterrupted career trajectory. But when it comes to women, women have children – not everybody and I totally get that if that’s not what you want to do – but, by and large, people would suddenly decide to have a family and so your uninterrupted career trajectory up to that point stops. Therefore, you kind of gone through, ‘Well this is all brilliant in my 20’s, that guy there, we completely match, no difference at all.’ But that’s when this sort of inequality starts to show. So if your 20’s is all about that kind of thriving and being driven, all the rest of it in your 30’s is what she [Avivah Wittenberg Cox] calls a cultural shock that hits your system. Because basically your career potential at that stage and your parenting responsibilities or your home life come crashing together like a force that you don’t really expect or are prepared for – as much as anybody can kind of ‘tell you.’

“And you then kind of have to go through this thing and balancing it all up so you’ve got your kind of your ‘pre-kids head’ on which is going: ‘This is what I want to do! I want to be up here, and I’m going to make it happen!’ And then you’ve got your daily life of, ‘Oh my God! I’ve got a baby to look after! What am I going to do?

“I remember when I first returned to work after maternity leave. I thought that basically I would drop my son off at nursery, I wouldn’t hear anything all day, and then I will go to work, and then I would come home – and my work life would stop and I will pick up again at home. But that doesn’t happen. I don’t know why I thought it would – total ignorance.

“It’s all very compartmentalised: my job fits there, and I walk in the door and I pick up my son and the next morning it all kind of… No, no, no. I mean literally the nursery will phone you up saying, ‘They have got a temperature, you have to come and get him,’ and you are sitting running a meeting. You have to leave. There is no choice. I had to run to the train station. I literally ran out of a meeting because I didn’t keep my eye on the time. Or you’re trying to breastfeed, and a work call comes in… and all of these things suddenly kind of kaboom together and it’s just working through that and I think it’s really difficult.

“There is this reality check of ‘I can’t do it right now,’ and actually, that’s okay, because you don’t have to continue its [your career] ‘trajectory.’ Your 30’s is this weird kind of period for women, for which men don’t have. It’s unfortunate that this is at a time when your career largely is really starting to drive forward. I think phase 4 [from the book] is really interesting about this resurgence – when it then comes in your late 30’s and 40’s, where women suddenly (their kids are a little bit older) can actually start doing more things. And there’s stats around about how many entrepreneurs or people setting up small businesses – women in their 40’s are the biggest demographic in that. Then you kind of go into your 50’s which is much more about self-actualisation.

“I guess the summary of that… I think that if more women understood that, I think in the middle kind of clash phase, it would provide a lot more comfort and it would really help your confidence and your mindset to go: it’s not about failing at anything – which so many people feel like. And I definitely felt like that. It’s actually fine and you are not coasting or anything, it’s just a pause.

Nichola: “It’s awareness of those phases, but also, everyone thinks that your career goes like that [pointing upwards] and it doesn’t. I actually think the younger generation coming in have got that more settled in their head then possibly my generation, because I think we naturally were told your career has to go like this [up]. Actually, I’ve done sideways moves, I’ve done all different moves, now I’m running a business and I’m also working in a role share.


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“There’s new rules now and you can make them. Think about what you want to achieve. Also, don’t judge yourself by other peoples’ successful traditional career routes. It annoys me. I mean I used to work in LinkedIn – it really irritates me still on the LinkedIn profile that you can’t show the fact that you’ve got more than one side hustle or whatever. Or that if you do have a side hustle it just shows a linear career, and I’m like, ‘Careers don’t work like that anymore!’ So on my LinkedIn profile I can’t really show that I’m a co-founder of a business and I work in a roll share I have to sort of weirdly put it in my bio because LinkedIn is still unable to. So, I’m always emailing their product people at LinkedIn even though I’ve left! They’re like, ‘Yeah we know it’s on the road map! We know!’


Lauren: “I think it’s so ingrained, isn’t it? So there’s a definitely the link between our confidence and the expectation of what we set ourselves. And then when it [our career] doesn’t match the expectation we feel like that’s a poor reflection on us, rather than seeing it as the expectations being unrealistic in the first place.

“So, overcoming those problems of confidence, and feeling heard, and feeling like a failure because you’re not on track in the way that you thought you were, how do you overcome those feelings? What are the strategies that you would say to somebody say to a client if they were feeling that way? What are the practical steps that someone will be able to take to help them?

Nichola: “There’s something in psychology, it’s all around a growth mindset and a fixed mindset, it was developed by Carol Dweck, so it really is taking it from seeing things in black and white and then actually moving it to be more around… you’re not afraid of failure, you will try new things. A lot is around self-limiting beliefs, so something you could believe to be true about yourself, which has been holding you back to the years in your career. So – my one. I always talk about is. I have this belief from about 10 years ago, 15 years ago now, when I worked at EBAY in the US. I had a problem. They muddled up my tax payments because I was being paid in the UK, but living and working in the US, so I was left with a massive tax bill and I didn’t notice because I was working between different time zones and currencies – and having a great time basically! From then I had this thing and belief that I was really bad at managing finances and it haunted me throughout my career.

“I was always scared of doing budgets and then interestingly during my career I’ve managed really massive PR budgets and because I’ve got this fear of money of finances I’ve never gone over budget I’ve run really big campaigns and I’ve also made sure that we stuck to the finances and then sort throughout its really taught me a lot of lessons to just be really super diligent I’m no accountant but I actually now know that I need to really work hard at doing things with this and it was only when I dug into well why am I feeling this way or it’s because of this eBay thing that happened years ago and actually I’m not rubbish at managing finances I had this one thing happens to me which wasn’t my fault but actually since then I’ve learnt and done it and I think a good exercise you could do is grab a pile of post it notes and write down all the things you believe to be true about yourself and then look at those and really dissect them and say why did why do I think that is it true do I still want that to be the right thing and I think that that can really help you start to be more aware so that’s quite a good tool to use to just give yourself a bit of a sense check of why am I feeling unconfident and what can I do to fix it and it’s just it you won’t fix it completely but it’s all about you having better self-awareness of it so you know what it is.

Calli: I would say there’s another one that we talk about which is all about identifying your super powers. Women tend to focus on the weaknesses and spend a lot of time worrying about the weaknesses rather than focussing on their strengths. The big thing wrong with that obviously is if you’re using all of your energy to focus on the weaknesses you’re not leaving anything else to give to really focus on your strengths and actually that just doesn’t make sense. So, you kind of need to go, you know, ‘What there are certain things that I’m not so good at?’ and make yourself comfortable with that. And it’s really, really hard. I remember being given that advice years ago and that someone said to me previously, ‘You’re not going to be good at everything.’ And I was like, ‘What? You are joking me? I’m clearly good at everything, you can’t just dismiss me straight off!’ But it was more that focus on what your good at. Make sure you properly identify what your good at and use that as your superpower and make sure you are the best at that thing.

“That’s something’s really good to do with a career coach or you can explore your kind of career timeline and just have a think about – When were those key moments when you thought, ‘Oh my god I smashed that! I was absolutely brilliant! I’m so pleased I did that!’ And it can be the smallest of conversation to a big business when it doesn’t matter but it’s identifying those moments and pulling out what those strengths are. It’s really a good exercise to do.

“The third thing you can do is collate working wisdom from other people. So, give yourself a set of questions to send out to trusted colleagues and friends and go, ‘What do you think I’m good at? And most people will be really happy to do that. I would be very shocked if anyone didn’t want to help. It’s a bit cringey but, you know, you just have to get over it and ask. People will be so happy that you have actually asked and care about their opinion. I think identifying your superpowers, and then making sure you have the right environment, are the two kind of key things really – and then it super charges from that.


Lauren: I think leading on from what you both said, maybe just like a last question to wrap it up,  would be around accessing coaching and how and why you would do that. I think a lot of people individually are probably quite reluctant. I mean, if it’s in corporate for example, and the team think someone’s coming in as a coach, they hope they aren’t really, really dry and boring! I have a business coach and have a life coach, I love coaching! But I think there’s still things that need to be done and these exercises you talk about are fantastic! But I do doubt that a lot of people will sit there and on an A4 piece of paper be like, ‘Okay, my strengths are…’ And maybe that accountability that comes with the coach is essential.  So, what are your tips of how and why women should access it [coaching] and find the right coach for them?”

Nichola: “The one thing I would just jump in and say is I understand what you mean about the branding and perception of coaching, because it used to be my experience of learning, about coaching, during my career. To be honest it wasn’t that positive. So I remember always being in that dreaded annual year review – the only time you get feedback – you zone in on anything they say negative because that tends to come up, because you’re not giving the feedback until the end of the year which is silly! You should be given the feedback regularly. I remember asking for a coach when I worked at a financial services organisation and was told, ‘You can’t, it’s only for very senior people.” And it was ironic because I wanted to have a coach because I was told I didn’t have the leadership skills!

“I think you want to look for one, look for the type of person not that you necessarily want to be, but have a chemistry call with coaches. You should interview them as much as they should decide if they want to work with you. Anyone who comes to Cali or I – we say we’re not bothered which one of us you choose it’s your choice to choose which one of us as well. But often I say to people, ‘Have you spoken to any other coaches?’ And sometimes they say no and I’ll say, well actually, I don’t mind, go and speak to some other coaches, have a chemistry call with them, because it’s as important that you feel comfortable with the relationship! I think it’s about doing your research.

“The other thing I would say is don’t fixate on just having a coach or just having a mentor. You have different people around you that can support you. I think that obviously we’d say it’s great to have a coach but I’d say think about the different people who can help you in your career at different stages and can do different things for you as well.”

Calli: I think it’s such a misunderstanding about what a coach is and actually I think it starts from people thinking s*** somethings gone wrong! I need someone to fix something! I think it’s actually a point of empowerment, I don’t think it’s about a fix because I think it’s you making an active decision to talk to somebody about where you want your career to go. I think if you frame it that way, immediately it feels more positive and feels more empowering. What I really love about having a coach and being a coach is it gives you that time to focus on nothing but yourself.

“And like you were saying about I don’t think somebody would sit down and write down their own strengths and weaknesses – I totally agree with you. I don’t think they would either. But I think in a coaching situation when there’s a topic or something that comes up and you want to unpack something, having that time to physically reflect and have somebody who doesn’t have an agenda of their own – they’re not going to throw in their opinion and tell you the answers… Because as a coach I mean we believe that everybody is very capable and whole and they can do anything they want to do! It’s just they may not have asked themselves the questions. So I think it’s just a brilliant positive environment for you to explore what you want to do or what challenge you face – whatever it is you want to do next. And I actually think it’s really good because it does drive actions.


Lauren: 100% agree! and I hope more Yellow Eve members will feel the same! I think it’s knowing where to go as well. We just talked about mentors – not just paid coaches – but mentors and reaching out. And I think a lot of people are receptive to helping you, but you have to have the confidence – maybe it’s a vicious cycle of being able to reach out?

Calli: That’s a really interesting point you said about the confidence to reach out because with some of our workshops we’ve had, actually, we’ve had some people messaging us saying we don’t feel brave enough to come to the session. And we say, ‘Just come to one, put your video off, we don’t have to see your face don’t worry – just listen in.’ And then your sort of confidence builds from there. Your network is really good and things like social media, Nic you found your coach through social media.

Nichola: Yes I’ve been following her on Instagram and she’s a journalist. Also, we talk a lot about passing it forward. Whenever I agree to mentor someone, my first question is well, one is yes I can do it, but the second request of mine is, ‘Who are you going to mentor in return?’ I always now have it reciprocated and if they say, ‘I don’t know who to mentor,’ I match them up with other people. My big thing is: if I’m giving my time, which I’ll happily do, I really want you to see the value in it and give up your time for someone else. I think that that’s a nice way of thinking about what help do I need? But what help can I give? Also interestingly it really builds the confidence of the person who was going to find a mentor in the first place because they’re like, ‘Wow my mentor thinks I know enough to give to someone else!’

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