Ep. 65 How to develop self-esteem and confidence

how develop self-esteem and confidence

In today’s episode, Anna looks at how to develop self-esteem and confidence, how you can feel more confident in what you do and how you market yourself as a business owner.

Isn’t it ironic that when you come out of school and university, you’re brimming with confidence, having no experience whatsoever and very few skills, and you think you’re the best thing that could happen to any company in the world… Then 10, 15 years later or more, you lose that confidence and you think, “Am I really good enough?” This week, we’re exploring how you can develop confidence in who you are and what you do – in particular when you’re transitioning out of the corporate world and into working for yourself.

*Resources mentioned during the episode*

The One Step Outside Facebook group– Join us over in the Facebook group to meet like-minded people who are working on reimagining success in their life and business and to get access to direct support and free training sessions from Anna. www.facebook.com/groups/onestepoutside




Hello there and welcome back as we look this week at how you can develop confidence in who you are and what you do. And this is a topic that came up as a very popular one, very much in demand over in the One Step Outside Facebook group. So hopefully this is going to be of value to you as well. I think as somebody said in the group, we can always do with getting more confident or at least most of us can. There might be a few exceptions in the world who are already maybe on the arrogant end of the spectrum. But most of us, I think can probably err on the side of becoming more confident. So why is this an issue? Why are we even talking about becoming more confident?

Well I think in the context certainly of making big life changes, changing career, changing job, even coming back to work after maternity leave, maybe being made redundant and having to look for other positions.

Certainly quitting a job to start a business, starting a new industry, become an entrepreneur and a business owner as compared to being an employee for so long. These are all massive changes and so it’s natural that we’ll feel a little bit out of kilter. We’re getting out of that very comfortable zone in which everything’s familiar. We know how things work. I think human beings are, from an evolutionary perspective, very much, I don’t want to say designed, and I’m going to say something wrong from a biological perspective, but my feeling is that we tend to want to belong and feel safe and we want to have that little cave and know the lay of the land outside. We know where the sabre tooth tigers are. We know where those other tribes are. We have our hunter team who are out there protecting us and so on.

Apologies to those of you who know more about these things than I do, but this is my understanding. And so it’s human nature to feel safe, to want to feel safe. It’s the bottom of Maslow’s Hierarchy of Needs. Having that security, having the shelter, and in our world today, certainly you listening to me, we’re very privileged to generally have that fundamental basic sort of shelter and home and hopefully also social connections and so on. So within that we are then throwing ourselves a little bit out of that, shaking things up a bit and putting ourselves into a new situation when we’re going to adapt. Again, human beings are very adaptable as well and you are more than capable of landing on your feet and getting to grips with this new job, industry, role, whatever it might be. But it does mean that we are going to have that initial phase of uncertainty and questioning ourselves and so on.

It’s ironic and I’ve talked about this before, that when we come out of school and university, we’re brimming with confidence, having no experience whatsoever, very few skills. And we think we’re the best ever thing that could happen to any company in the world. Where suddenly 10, 15 years later or more, we lose that confidence and we think, am I really good enough? And what if and so on, and there’s a few phrases, terms that come to mind here and of course one is Imposter Syndrome. Imposter Syndrome, unfortunately is something a lot of people relate to. Sometimes I think it’s not very helpful to label these things because having a word for it makes you think, oh yes, I have that and then you just sort of accept it and it’s certainly not something we can or need to or should have to accept, it’s certainly something we can work on.

But Imposter Syndrome, feeling like an impostor, feeling like we don’t belong here, someone’s going to see through us, who am I to think that I’m good enough for this and so on. Sometimes there are male-female differences.

There is that classic sort of statistic which is along the lines of most men, let’s say a lot of men will apply to a job when they tick, I don’t know, 6 out of 10 of the boxes. Women tend to not apply unless they tick 11 of them and that’s not just men or women. I’m sure there are differences and within gender as well, but certainly, some of us maybe are less confident than others and really want to feel that, yes, I know I’m capable and I’m more than capable. And it’s interesting because I certainly have a bit of that. And I know when I was working at Proctor & Gamble, we talked about them hiring insecure overachievers. So a lot of people who are very much always pushing themselves, very capable, competent, smart people, hard working.

But for that reason they’re always going to push themselves a little bit too far actually, constantly looking for that sort of gold star, the complements, the praise, the whatever it is, the salary increase, the promotion, whatever it is that drives them. But being a little bit insecure is what gives you the edge. And to be honest, it’s no bad thing to have a bit of an edge. And you certainly don’t want to be resting on your laurels. And again, err on the side of arrogance and think I’ve got this. Certainly the world is changing continuously. So even if we happen to be excellent today, who knows what will happen next week, next month. So we do need to continue to invest in our own skill, capability building, personal development and so on.

But all this to say that it’s totally natural to feel a bit of that Imposter Syndrome.

I’ve talked about the Good Girl Syndrome as well when we’re again looking for that permission, looking for the gold star, the teacher telling us we’ve done a good job and so on. So of course the question is what can we do to feel more confident? And specifically I’m talking about confidence in who we are and what we do. And that could be in a normal job as they say, office job. But I think when you have a job, for example, I would say I’m brand manager at P&G or I’m head of digital here, or whatever it might be, that already gives us a bit of kudos or respect. We have that kind of backing of the big organisation, the heading, I’m president of this, I’m senior manager in that and so one. Whereas somehow suddenly when we’re working for ourselves, we lose that whole big company backing.

Ironically a lots of us will give ourselves really fancy titles in particular in tech startups. Everyone will say, oh, I’m the founder of this. I’m the CEO of that. Which, fair enough you are. But you’re not telling people that you’re the only person in the company or you have no sales or profit right now. So I think that’s a little bit ridiculous when we do that. And to be honest at conferences and things, everybody will see right through that. So we do need to swallow our egos a little bit and recognise that you know what? And of course it all comes down to our definition of success. I’ve taken a step back up from this position for a reason because I don’t identify with that level of success, or that type of success rather. I’m not looking to proceed, progress up that linear career ladder to get to VP, whatever it is in the organisation. I’m looking for something very different.

And yes, for a few months, years I might have to take a little bit of a step back, but you certainly aren’t starting from scratch completely. You can and absolutely should leverage your existing skills, strengths, experience, and you need to use those things to rebuild your confidence to get back on top in a way in this new field. So looking I guess specifically at working for yourself, running your own business, how can you develop that confidence in who you are and what you do? And the first thing of course, and I’m going to give you five little tips here.

The first one of course, is to get clear on who you are and what you do because having the clarity and conviction of knowing that you have worked out what success looks like for you, you’re clear on what’s really important to you, you know your values, you know exactly where you’re heading. And I’m not talking about the exact business model and step-by-step for the next 10 years. I’m talking about the general direction. I know that I’m being true to myself right now. I know that it’s really important to me to have an outlet for my creativity, to be able to express myself, to be authentic to who I am. I know that teaching mentoring is a really important part of what I thrive on. I know that I am a really good independent worker and I really value autonomy, freedom. So really understanding those parameters, understanding that I’m really working towards this bigger mission, my bigger why is this, I want to help people in my case, find their definition of success and really find work, create work that aligns with their priorities, that works around their life rather than vice versa and so on.

So what’s that bigger why? What is important to you?

What, I guess to some extent, what’s your personality? I work in my programme I have a exercise, I guess that I call sort of the different characters, which can be quite enlightening in terms of thinking okay, for example, for me, I certainly used to have, maybe she’s gone a little bit. But there’s a bit of a free spirited hippy in there. There’s the serious sophisticated business owner. There’s the mother now, whatever adjective I want to add to that, loving, maybe nurturing mother. There’s hopefully sort of a sexy, independent woman in there as well. There’s the partner, there’s daughter, there’s all sorts of facets to your character and understanding those and ideally allowing each of those to come out, to come into play in some form.

Maybe it’s through your work, maybe it’s personally and so on, but really allowing all sides of yourself to come into play. So really clear on who you are, what’s important, what are your values. And then when it comes to the business, and of course this is a whole other topic, but being really clear on what you do. So there’s the classic elevator pitch. I do X for Y so that they can dah, dah, dah. So who do you help? How do you help them? And say what’s the real reason why you’re helping them? What’s the ultimate result they’re getting? And not getting caught up in job titles. Again, it’s not, and I can obsess over this. Am I a business coach? Am I a success strategists? And so on. Nobody cares. You really need to understand how you’re helping people. People just get it, and it used to be a normal language that people get.

And of course you can tweak it for the audience as well. If you’re at a conference, you can speak in a much more natural way perhaps than you would on LinkedIn, on your website. You might use a bit more formal language, when I’m on camera, might say something different and so on. So getting clear on who you are and what you do. And of course, as we talked about a couple of weeks ago, knowing that there is no right answer. So don’t obsess about I haven’t quite got the right title or positioning or whatever it is. You can tweak. You absolutely will evolve over time. Number one, get clear on who you are and what you do.

So number two is map out your skills and strengths.

And as I hinted a few minutes ago, do not forget all your years of corporate. So for example, for me, I could say I started coaching in 2015, I set up my business in 2014. So a year earlier, it’s already five, six years ago, which is great. It feels well both long and short to some extent. However, I could also say I’ve been coaching since at least 2011 when I had my first direct report and manage the Digital Centre of Excellence at P&G. Not just coaching there, but presenting, pitching, negotiating, speaking, writing to be honest. I’ve been writing publications and all sorts since I was, I don’t know, 10, probably younger, right?

So it might be silly to say that I’ve been a writer for 35 plus years, whatever it is. But certainly we can look back and dig into our history and find things that we’ve been doing, skills, strengths in our hobbies, in our personal lives and work as well, that can really bolster our confidence and go, hang on a second, I’m not just a newbie here. I’m not just starting design today. I’ve not just started this communications business now. I’ve been doing this pretty much my whole career and as Steve jobs says, “You can connect the dots looking backwards.”

And a third one then is collecting your compliments. Now certainly I don’t want us to rely on external praise, this whole Good Girl Syndrome of needing people to tell you you’re good and relying on that to validate ourselves. However, let’s face it, it’s pretty nice when people say good things and I think most of us tend to downplay those. And so, and I had this just the other day, in fact. We should 100% believe every single amazing thing people say about us because for some reason we tend to believe the negative stuff. If a client doesn’t buy from us, we go, oh my gosh, I didn’t do that right. The program’s wrong. I’ve got to tweak and I didn’t do the sales core properly and so on. If some troll on the internet, something negative about you being privileged and dah, dah, dah, whatever it is, you go, oh my goodness, yes I am. I can’t believe I’ve done that.

If you’re, I don’t know, partner or friend says something a little bit negative, then you get really upset and you take that really personally.

For some reason when people say something amazing, we sort of brush it off. So your job is to believe 100% absolutely every single positive thing that people say to you and to really amplify it because they say you need five good things for every one negative thing which means we need lots of good things. So client testimonials, feedback, emails, little thank yous, take screenshots, put them in a folder, put post-its. This is first of all, of course, good for your website and social media, and so on and for your credibility, but it’s also good for you. Every time someone says something, just write it down in a little notebook, put it in a little jar, collect all those compliments, collect the praise and you can refer back to that when you have a bit of a dip. And to be honest, probably regular, you should be looking back into that and reminding yourself, oh yeah, look at all these amazing things people have said about me.

Now the fourth thing is to work with a coach because a coach can really be a sounding board.

They can offer you a different perspective and importantly they can really cheer you on through those dips and remind you, they’ll reflect back. So I can really mirror back to you, hold on a second. I hear you saying that you’re really lacking confidence in this and you don’t feel that you have the experience and you don’t feel comfortable selling yourself and so on. However, just a minute ago I heard that you are saying, but I know I have the skills and experience and I’m so passionate about helping these people and I know I can make a difference. So just hearing that from somebody else is really important and then you can think, oh yeah, I did say that. So maybe hang on a second. I do have that confidence. I just need to remind myself and to realise that this is just a bit of fear sort of creeping in because you’re outside the comfort zone, bit of resistance to let’s say selling yourself and so on.

So having that sounding board, the different perspective and someone to mirror back to you actually the things that you’re saying and pull out, draw out the confidence that is already existing in you is really powerful. And of course again cheering you on through the dips. And the speaking of cheering you on, of course, in addition to a coach having that community that will lift you up. So of course I’ll refer to the One Step Outside Facebook group. Fantastic place to be. You can share your wins and really meet lots of like minded people who are working on re-imagining their own success as well as the outsiders business accelerator.

So this is something I launched early this year, so 2020. I’ve got the first group having joined now, been working together for a couple of months and it’s really designed for that ongoing support. So once you’ve set up the business, now what?And I think unfortunately the reason why most people fail is because they give up too soon. And when they give up is after that initial euphoria and excitement of starting the business. When it gets a little bit tough then or maybe a lot tough, then they tend to think, oh this isn’t going to work and I better take another job or so on, right.

So that’s what the business accelerator is for, of course, to help you with strategies, support and so on from a tangible business perspective.

But also just having that community, you can share your wins, you can share, hey hang on, I feel a bit sort of down about this and whatever it is. And that can really help you to develop the confidence and resilience to keep going. So working with the coach, finding community.

And then finally, of course, again, very obvious for me, One Step Outside, start with one little step. You don’t have to go out there in the world and go, boom, I’m incredible at this. I’m going to pitch Oprah. I’m going to be on BBC News here in the UK, whatever it is, right? So you can start, especially if you’re early on in the process, practising your elevator pitch, say it at home, maybe write a little short form post on LinkedIn, maybe pitch yourself to a small podcast that’s just started, only have a few episodes. So they’d be really happy to have you and you’re not going to be pitching yourself to one of the top, Entrepreneur On Fire, whatever podcast that has millions of people. In fact, you have to pay for that one now anyway. So start with little steps.

Once you get comfortable with pitching that little podcast, then you can pitch a slightly bigger one. And so on. And before you know it, you will be on Oprah. Amazing. So tweak and refine as you go as well. Swallow your ego. That’s really important and be curious. Just be willing to learn. Now that you know what? Yes I am to some extent starting from scratch here. So it’s natural, as I said right at the beginning, that getting out my comfort zone in a very different scenario here. Of course, I won’t be amazing from day one. If you were, it’d be pretty boring because part of the reason why you’re doing this new thing is because you want to get onto a steeper learning curve. You want to challenge yourself. So bring that approach, embrace it, enjoy it, be willing to learn, be curious and start with those little steps.

So those are a few little insights about developing your confidence, some suggestions as to how you can develop your confidence in who you are, what you do. Get clear on who you are and what you do first of all, map out your skills and strengths, collect your compliments, work with a coach and find that community and then start with little steps.

Now as you listen to this, we will have just done a free workshop on this in the Facebook group last night. So first of all, of course do come on over and join the One Step Outside Facebook group to make sure that you access this training and other trainings as well. And you can also vote for topics in the future so you can really influence the content that I’m providing you with. However, it’s also available on YouTube. So if you go onto YouTube, you can find my channel and you’ll be able to find all the videos from our previous Facebook lives as well. So you won’t get the interaction, you’ll have the opportunity to ask me questions, but you can find a Facebook live workshop playlists there and you can watch all those training sessions as well. But if you’re active on Facebook, would love to have you over there, because of course that’s the best way to really, again, get that community to interact with other people and to work with me one on one with all those questions and so on.

So again, hopefully this is a few little indications of things you can do. Have a think, maybe listen again, make a note of where you think the biggest opportunity for you is. Maybe it’s actually getting clear on who you are and what you do. That’s going to really give you that confidence. Maybe it is doing that compliments jar or folder. Maybe it’s joining the group as a first start, or reaching out to me to see if we can work together in a coaching capacity. So really have a think about what’s one thing that’s going to make the biggest difference for you.

And next week we’re continuing in a similar vein because we’re looking at comparanoia. So comparanoia is excessively comparing ourselves to other people. And that’s certainly very related to that idea of developing your confidence because if you’re constantly looking at other people, you’re not running your own race. You’re not focusing on your own definition of success. That is going to really get you down rather than what we can do to give you a bit of a glimpse already of next week’s episode, is to really get inspired by other peoples’ success. Embrace it, celebrate it, and see it as proof that you know what? This can absolutely work for me as well. I’m meant to double down and work hard. So that’s on next week’s episode. So do check that out, comparanoia, overcoming comparanoia. So have a wonderful week and I’ll see you back here next week. Bye for now.

Connect with Anna:




If you’re ready to start to reimagine what success could look like for you, here are some of the ways in which Anna can support you:

Get private mentoring for your business – Partnering with a business coach can help you see those blind spots and get both external accountability and expert guidance to take your business to where you want it to be. www.onestepoutside.com/freeconsultation

Get private career coaching – Individual coaching is fully tailored to your specific goals and desires so we can create the programme that works best for you, with the support that you need to move forwards. www.onestepoutside.com/claritycall

Grab a copy of Leaving the Corporate 9 to 5 – After interviewing 50 people who have left the corporate 9 to 5 to forge their own path, Anna has collected their stories in a book that will inspire you with the possibilities that are out there and reassure you that you’re not alone in looking for an alternative. www.leavingthecorporate9to5.com

Join the One Step Outside the 9 to 5 Business Incubator – This is your roadmap to transitioning from a corporate job into setting up a meaningful business that will bring you more freedom, flexibility and fulfilment outside of the corporate 9 to 5. www.onestepoutside.com/9to5

Level up with The Outsiders Business Accelerator – This is a mastermind for entrepreneurs, freelancers and small business owners who want to create a long-term sustainable brand and business. www.onestepoutside.com/accelerate

Up-level with the Fast-track your business programme – This is your guide to taking your business from surviving to thriving and making sure that you achieve the freedom, flexibility and fulfilment that you dreamed of when you started. www.onestepoutside.com/fasttrack



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