Ep. 104 What to do when you want to quit your job

what do when you want quit job

In today’s episode, Anna looks at what to do when you want to quit your job, and then common mistakes and pitfalls to avoid as you navigate the transition of leaving your 9 to 5 to work for yourself.

Leaving behind everything that you know in the world of full-time employment to embrace working for yourself is a huge decision and a massive change, and it’s easy to focus on everything that could go wrong. “What if…?” “But maybe I can’t…” “What do I do if…?” A lot of mistakes can be avoided if we think it through, plan ahead, and work with someone who has “been there, done that”.

*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, hello, how are you? I hope you’re well and enjoying the series on leaving your nine to five.

Now, today I wanted to address some potential mistakes because, of course, there are some pitfalls when you’re navigating this transition, this big decision to leave possibly a career of years, if not decades, in a particular environment as a full-time employee to pursue something else, to work for yourself and so on.

So I wanted to talk you through five common mistakes that I see again and again, probably saw in my own experience, certainly seen it in friends and colleagues and clients and so on, so I want to address those with you today. And of course if you have any more that you’ve had from your experience, because I now have lots of listeners who have already quit their job, then of course I’d love for you to share those. Maybe comment on the social channel wherever you’re listening at the moment to let me know your thoughts as well so other people can learn from your experiences.

But the first mistake is actually not to do with you, it’s to do with other people. In fact I’ve seen this when I’ve asked the question, I’ve seen other people ask in Facebook groups what’s the number one thing stopping you from achieving your goals? Interestingly people, a lot of people do say other people, which is odd and I found that quite disempowering in a way because we’re really putting our destiny, our goals, our happiness on other people and of course we have to recognise that, and in fact we have to take ownership of our own decisions, regardless of what parents are saying, friends, colleagues, bosses and so on. Ultimately we are human beings with their free well and we can make our own decision within the context of where we are, so that’s important to remember.

However, in this context, this idea of other people, so the first mistake I want to talk about is letting these other people discourage you from exploring and finding your own way.

And it’s something again and again that comes up, so the classic is it could be a partner, although many partners are very supportive, of course, and that’s really key to navigating this transition.

More often than not it’s perhaps some traditional parents, family in particular in certain cultures, well meaning people who care about you who are worried, it might be a partner who themselves are questioning a little bit their own career choices and of course you beginning to question yours will cast doubt on theirs and put them on some shaky ground. So they’ve been comfortable, look, we’re all in this together, we’re doing these corporate jobs. Yes, we’re not 100% happy, but that’s kind of the way it is. If you start questioning that, then that will have reverberations on your partner, on your friends, on your colleagues and so on.

So certainly your colleagues and probably most of your friends will be in your little bubble. Most of my friends, if not from the same company or at least from a similar kind of academic background, working in a full-time job as an employee, I certainly didn’t have a lot of entrepreneurial friends, freelancers even, people who are writing books and doing TED talks and so on, when I began this journey, so that’s important to remember. So, the first mistake is to let other people discourage you.

Now, okay, briefly how can we address this? And there is a whole episode if you scroll back on the podcast app that you’re listening to at the moment on how to overcome objections from other people, so do find that and let me know if you need the link to the episode. That will be interesting to listen to.

But in a nutshell, recognise that it’s not about you, it is about their own insecurities and fears. Obviously you need to determine is this someone who I want to listen to or not? If it’s your partner, your parents, your sibling, your close friend, then it’s very important to recognise that is someone who loves you and who you love and you might want to listen more seriously and work with them closely to help them understand. If it’s a stranger on the street, if it’s some distant colleague or some one relative who you don’t care so much about what they think, then maybe that’s something you can really just try to ignore. Certainly if it’s a stranger on the internet, definitely ignore that one.

So determine who it is and how important their opinion is to you, but recognise it’s not about you, it’s about their fears, their upbringing, probably having grown up in a different kind of environment and their insecurities as well.

Now, what I always tell my clients is try to incubate yourself, incubate your idea. When you’re starting out, you already have lots of insecurities yourself, and other people just reinforcing those fears and insecurities isn’t going to be helpful. If you are every day saying to your partner or to your parents, “Oh, I’m going to quit my job and travel the world” or “I’m going to become a writer.” “No, actually I’m going to be a coach.” “Oh, I have this idea I’m going to start this business.” “Oh, there’s this co-founder who wants me to come on…” If every minute, every conversation is a different direction, completely fair enough, because you’re just exploring and you’ve got lots of ideas and that’s fine, but you can see from the other side of the equation how somebody might think you’re a bit flaky, wishy-washy and they might start worrying about you because you’re all over the place.

So what I would recommend is take a step back, by all means find a trusted friend or someone you can speak to, of course working with a coach, that’s what my clients do with me. We can really talk these things through without then going back every day to the partner or to the best friend or family member. We can sort of get the clarity on what’s important first and then once you have at least a loose kind of plan or a direction, then you can, of course, and you may need to, discuss this with someone who will play an important part, for example your family if you have older children, if you’ve got a partner, you know, your livelihood depends on your income and so on, and so it will be important to have that conversation.

But again, recognise it’s not about you and incubate your idea, and if possible, bring them on board.

I know somebody who actually did a PowerPoint presentation to show his parents, “Look, this is what I’m going to do. I’m going to start a blog,” and so on, and that was back in the day when people didn’t really know what that was about. Even now, of course, lots of our parents probably don’t really understand how we’re making money with our businesses, and that’s okay, but it is important to have that support, so if you can try to bring them on board as well.

And of course, and I said this many times, but find your tribe, as we call it. So I have the One Step Outside Facebook group. I cannot emphasise enough how important it is to find those people who are out there, who are doing the things you want to be doing and you’ll realise soon enough it’s not naïve what you’re thinking, it’s completely possible, people are doing it already, you can absolutely do it. But in order to believe that, you need to surround yourself with new voices. Listen to podcasts like mine and many others that will inspire you and give you concrete tips and ideas, meet people either offline or online, read books, join a programme, just make sure that you have those positive influences as well as the negativity that might come to you.

So that’s number one, don’t let other people discourage you. Then number two, don’t, and this is bringing it back to you because that’s what’s important, don’t undervalue your skills and experience. Again, it’s something I’m sure I’ve talked about before, but when we come out of school and university, we’re uber confident with thinking, “Oh my goodness, I’m the best gift to any industry and I’m going to change the world,” and the reality is we have no experience, we have maybe have a bit of an academic degree, probably in an unrelated topic, and so it’s pretty naïve of us to come out, but nonetheless we have that confidence.

Bizarrely, ironically, 10, 15-plus years later, we have less confidence because we’ve been in that sort of pigeonhole box. Recruiters will want to put us in the same box, we feel like that’s all we can do. Yes, we’re in our comfort zone and we’re great at what we do, but somehow we’ve limited what we believe is possible and we’re only thinking, “No, I can only do this social media management or project management or marketing in a corporation for this type of product. I couldn’t possibly do this other thing. I can’t work for myself,” and so on.

And that’s a shame because you have so many transferable skills, you have so much more than you had, certainly when you were 18, 20 in your early career, and you’ve built so much career capital, whether it’s, by the way, your network, of course, people you’ve met along the way, but also things like problem solving and negotiating and presenting, managing a budget, maybe you’ve been responsible for a P&L, managing a team, coaching, leadership.

There are so many aspects that you have to look beyond your job title, and again, partnering with someone else to really go through, look beyond the CV, look beyond those little bullet points of your achievements and the kind of achievements you would really consider within the ranking and the job review process internally and really think beyond that, and by the way, think beyond your work as well, because you have hobbies and interests and as a parent, and even if you’ve taken a career break to have children, there are so many things.

I worked with someone some years ago who had taken a very long career break and she had done so many activities with the kids’ school, courses and so on, and yes, it’s not the same as having done maybe a large chunky senior role in a company, but there are so many aspects there that really make you more interesting if nothing else. So really look beyond the obvious and certainly don’t think, “Oh, this is the only thing I can do and I couldn’t possibly start my own business. I couldn’t possibly have anything to offer.”

What’s really important to realise is as an expert, and it’s strange to think of yourself as an expert, but you only need to know, some people say, 1%, 10% more than the person you’re working with, so I could definitely advise somebody who knows nothing about SEO and Google Analytics and so on, I could definitely help you get set up. It’s not something I particularly enjoy or would focus on because I’m not completely advanced in that, but if you literally know nothing about it, I know enough to give you the tools to get the basics there, right? Then there’ll be someone else, of course, who can teach me because they’ll be ahead of me and they’ll be the ultimate expert in the world, you know, Google themselves and so on.

Of course, we’re not going to be Google ourselves, that’s fine, but nonetheless, I can still have a service if I wanted to, or certainly an element of a service that I was offering where I was helping complete newbies, teaching them how to set up in Google Analytics SEO.

So, it could be anything. It could be, I’ve said this many times too, I’m not going to go out and tell you, hey, I’m going to get you to an eight, nine figure business and a massive team and a product business where you’ve got the distribution internationally and so on, right? I focus on service-based entrepreneurs, mainly at least, and even though I come from product background, interestingly, and I feel very confident with helping you through the process of navigating the decision to leave, I’ve done that, to deciding what you want to do, to setting up the beginning of the business, to consolidating the business and growing the business to a certain level, so a really wide range of things I can help you with, and for someone who’s at the beginning of the process, I will be seen as an expert because I’ve done it, I’ve been there, I’m way ahead of them, actually. You don’t want someone who’s too far ahead of you, but certainly a few steps before, right?

So I can guarantee you there are many areas of your life, your business, your career, where you absolutely are an expert in the eyes of some people.

So don’t undervalue your skills and experience, and related to that, the third mistake that we can make is to assume that you need to [inaudible 00:10:42] in formal qualifications and degrees.

Now, I remember someone, and again, I’m sure I’ve mentioned before, and I don’t want to paint this person in any dark colours because everyone makes their own choices, but I’ve seen, in fact several people, let’s say, who have done a degree at Oxford, they’ve done their master’s at Cambridge, they’ve done an MBA and Stanford, they’ve done this, that and the other, and it’s just adding accolades to your CV. “I’m going to do a PhD now. Oh, no, I need an MBA, or I’ve signed up to this really expensive programme. It’s a three-year course to X, Y, Z.”

Now, I’m all for academics. I’ve done an undergrad and a master’s, I love doing course. I’ve done so many courses over the years. However, informal learning is so powerful these days. It’s available to us, there are free courses, in fact, online university courses. You can study via Harvard, MIT, whatever, if that is what you want to do. You can learn on the job, you can learn by working with a coach, a mentor, there are so many ways in which we can learn, and again, don’t assume that you have to have all these skills and qualifications and accolades before you get started.

It happens especially for coaches. We feel like, “Oh, I’m starting from zero and I need to have this formal qualification, I need to have this, that and other,” and the reality is a client is going to work with you when they can see that you can help them, when they believe that you can help them, so there’s the whole know, like and trust.

Okay, they know who you are, what you do, they really like your style, they’ve joined your lives and they’ve read your content, they get it’s clear that you’re an expert, they trust that you can deliver on the promise to them, so whether you then have this particular accolade or you’ve done that course or this course, of course it gives you things to talk about, of course if you’re working with a particular target like corporate organisations, they might want those formal qualifications and things, and that’s a specific audience that you might be working with.

But really, people want to work with you if they believe that you can help them, and even if you do want to or need to invest in those qualifications eventually, certainly don’t let that stop you from getting started because you can start now. Again, remember you’re an expert to somebody out there, so start helping with what you can help with and then by all means expand and evolve, and we should all be investing in our lifelong learning and skills development and so on. But don’t think you first have to re-qualify, retrain with some expensive training, and the biggest mistake there, of course, is that we do that retraining only to wake up at the end of it saying, “Ooh, this isn’t actually what I want to do at all,” which is a complete waste.

Now, speaking of that, number four is don’t narrow down your options too soon, so don’t, again, from the limited space of being in this corporate job, think, “Oh, I’m going to do this kind of consulting,” and that’s all you can do. Because, actually, there are so many other things that you might have considered, that you might want to consider.

So I always with clients and everyone in my Facebook group in any training I do, I always say, take that step back if you can, whether you do it alongside a job. If you’re lucky like myself to be able to take a sabbatical, if you’re able to even take a little bit of time off just to explore, reflect, imagine, brainstorm, really map out any idea you ever had. Explore your values, think about what’s important to you. What are the criteria? What are all the ideas you’ve ever had in your life and really explore the possibilities.

Now, some things might not be possible today or tomorrow, but knowing that, you know what, in the future my vision would be to have this space by the sea and the retreat [inaudible 00:13:57] this and I have a horse and a vineyard, and however far off and crazy and naïve it sounds, knowing that is the direction you want to get to will at least help you then take the right next step and rushing into, again, a formal qualification or applying to lots of random jobs online, ending up somewhere where you’re thinking, “This isn’t at all what I want to do again,” that’s just taking your step back if nothing else. You won’t be any better off a year, two years, three years down the line. So really take that time to explore, imagine before you narrow down your options.

And then the final thing is don’t wait for the perfect moment because, guess what? It’s never going to arrive.

So we’ve all heard this fallacy of “I’ll do it when…” I’ll do it when I’ve got a promotion, when the kids are older, when the kids are born, when the kids are not born. Maybe we don’t have kids. Who knows? They’ve moved out of the house. When I’ve sorted this, when I’ve lost weight, I’ll do it next year. I’ll do it when COVID is over, or whatever, and that’s fair enough because it could be that there’s a very good reason for why now is not the right time.

However, if you are going to postpone the decision, postpone the process, I’d really urge you to make sure that you have a plan, a milestone. This is the deadline and an action plan with milestones. You’ve got the support, you’re working with a coach or a programme to get you to where you want to be and to make sure that you’re not just saying, “Yeah, I’ll do it later.” But really, “Okay, yes, now is not the right time. I’ve thought it through, I’m going to do it this time next year and this is the plan to get myself there.”

So there we go, five mistakes that I want you to avoid if possible. Learn from my mistakes, learn from the pitfalls that other people have gone through. So number one, don’t allow other people to discourage you. Two, don’t undervalue your skills and experiences. Three, don’t believe, don’t assume that you have to invest in some kind of formal qualification. Four, don’t narrow down your options too soon and make a decision that you might regret later before you’ve explored it, and five, don’t put it off indefinitely. If you do have to postpone it for now, that’s absolutely fine. Make sure you give yourself a deadline, a plan, milestones and criteria for when you will be able to do it, and get the help you need to get you there to make sure that the situation has changed a year from now, rather than be in the exact same situation and then again delaying it again and again until it doesn’t happen.

So I hope that was useful. Again, I’d love to hear your insights if you have already gone through this process, if you have other mistakes that you’ve made or managed to avoid somehow.

Thank you so much for listening and I’ll see you back here next week. Bye for now.


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

Up-level 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


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