Ep. 44 Questions about leaving corporate

questions leaving corporate

In today’s episode, Anna answers some of the questions about leaving corporate that have come in, in relation to the Outsiders Business Incubator.

Questions include…

-How much savings buffer do you need when you leave your corporate job?

-How do you keep up to date on the latest developments when you’re self-employed?

-What does participation in the programme look like in practice?

-In the programme, how do you handle working with people at different stages of the process?

-Would you ever go back to corporate?

Still have questions? Get in touch at podcast@onestepoutside.com

*Resources mentioned during the episode*

Join the Outsiders Business Incubator programme– 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

Questions leaving corporate


Hey there, and welcome back. Now, if you were listening to our episode last week, you’ll know that we have opened the One Step Outside the nine to five doors for enrollment.

This is the new revamped version of the programme. As we are speaking now, September, 2019. So, it’s a comprehensive 12-month programme to take you from a state of confusion, procrastination, feeling stuck about which direction your career should head in. Do I want to start a business? What business should I start? How on earth? Do I get this off the ground, right through a position of clarity and confidence and conviction that you’re on the right path.

And let’s throw in a few more alliterative words there, creating that freedom, flexibility, and fulfilment they’re always talking about. So, all the details of the programme are on onestepoutside.com forward slash nine to five. And the nine and the five there are numbers. So, one step outside.com forward slash nine to five. However, this week I wanted to do a slightly different type of episode, a bit less polished maybe than usual, because I wanted to do a bit of a Q&A.

I had quite a few questions coming in, in the different forums over the last few days. And I thought it would be a good idea to answer some of them here. Of course, if you have any other questions as well, then do email me podcast@onestepoutside.com. So, let’s dive straight in.

The first question I got was if you’re leaving the corporate nine to five, which is what we’re talking about, of course, and when you’re starting out, how much do you recommend saving, putting aside for bills? Is it three months pay, seven months pay, 12 months pay, what’s the magic number?

And you may have seen a magic number sometimes. And I’ve certainly had three months before. I’ve had six months before. A friend of mine actually said, you know what? I think you need 12 months of savings. However, it really depends on a couple of things. And as usual there isn’t really a simple answer. First of all, it depends on your level of spending, your obligations, your family situation, and so on. What discretionary spending can you actually cut down on?

So, how much is leaking out of your bucket? Because of course the more the leaking out, the more you’re throwing out the bucket and the more you’ll need in terms of saving. Certainly if you’re going to quit and take that leap of faith without building the side hustle alongside your corporate job. You’re going to very quickly go from high six-figure-plus income in your corporate job to nothing at all, unless you have a bit of gardening leave and so on but the package will only take you so far.

So, how much do you need in your bucket depends on how much is leaking out, how much you’re throwing out. When I say throwing out, the reason I say that is because when I first put… Between my consulting contracts I was very lucky to land on my feet and have some really big corporate client contracts when I left. However, in between those contracts, I was very much living a pretty amazing life. I was travelling a lot between each contract. I’d go to Asia or Australia. I was in Japan.

I went to a wedding in New York. I did some fantastic things in, California. We went hot-air ballooning in Napa and flew over Grand Canyon and so on. As you can hear from what I’m telling you, incredible life experiences. However, also very expensive. And initially I was working as a consultant, but then I actually sort of quit that work and then went through what I always call my hippie phase, when I wasn’t bringing in a lot of money. And so, I was very much working through my savings.

So, if you’re like me and you want to really enjoy that life, that’s all well and good. But of course that means that bucket is going to leak out much more quickly and you are going to need a whole lot more savings. The other side of the coin of course, is the money coming in. So, again, of course, if you have your full-time job still, or a part-time job or a contracting job, you can do, that’s going to bring in additional income and buffer for you.

So, it’s not just about savings you have, but actually have revenue coming in, which is much more important and much more effective than just having savings. So, rather than just cutting down on your spend, you’re actually bringing in money. So, it might be that you still have that salary or you’re getting the part time income coming in, or maybe you’re already far along already and you’re thinking about your business. You already have a pipeline of clients and you reckon you can really hit the ground running.

In which case you’ll start bringing in that money much more quickly than someone who’s much earlier on in the process. So, not to complicate things for you, but of course, there is no easy answer here. It very much depends on your situation. And, if you want to chat to me about that, then you can always get in touch. But again, do consider the two sides of it: So, cutting down your spending and saving more on the one hand, but also of course ultimately need to be bringing in money.

So, it could be through consulting, freelancing, it could be through your existing job. And ultimately you want of course to be through your business.

Now, another question, which is not so much specifically related to the programme, but just a doubt around being self-employed, which I thought was great, which was: how do you stay relevant with changes in technology, best practices, the digital space and so on?

And I think that’s a really interesting question because when I was at Procter & Gamble, I worked with high-level agencies, Google, Facebook would all come to us and teach us the best practises they wanted to partner with us.

We did some incredible pioneering things on YouTube and so on, right? So, we had access to the best minds, senior directors at these leaders in the digital space, not to mention all the training and so on, that the company, of course, paid for. Now, I think it’s great that you’re asking this question, because if you recognise the importance of getting that training for yourself, then that’s already a step in the right direction. And I would definitely recommend that you put aside a portion of your budget as soon as possible.

As soon as, again, you bring that money in. Or if you can, from your savings to make sure that you’re investing in yourself and staying on top of things. Now, that does include digital tech and so in my case, because I’m teaching people about these things, I’m doing digital marketing consulting and so on. And I must say that I find my training comes from really reading. So, whether it’s on LinkedIn, Twitter, Google, and so on, listening to podcasts, subscribing to newsletters and so on.

Potentially going to conferences and things, but make sure that you’re going to a conference that really does have the elements that you want to find out about. Some of them can be a bit quite glossy but actually don’t learn very much realistically. And then, of course, the other piece is in my case, the work I do by its very nature means I have to stay on top of it. Number one, because I do this, marketing, writing and training in the areas, the very latest areas of digital disruption and things like artificial intelligence and internet of things and smart speaker marketing and so on.

And so, I’m very much I’m on top of all those latest trends, but also because I run my own business. So, I have to, as a business owner, as an entrepreneur, stay on top of these things and make sure that I’m learning the latest things. So, there’s an element of knowledge and skills and that kind of thing, but there’s also an element of mentoring guidance and of course coaching. And that’s something again that I absolutely recommend that you put aside a chunk of money for the plan that into your expenses. And that really is a business expense.

So, I would absolutely always have a coach myself, as a coach, I think that’s absolutely critical. And if you’re considering coaching the first thing you absolutely must do is get a coach both because you need to be coaching yourself at being coached to become the best version of yourself. Which is what we’re hoping to be ourselves and also help others become. So, you can really invest in your own personal development, but also more pragmatically. You want to learn what other people are doing.

You can see how they set up their calls, their consulting, discovery calls, their funnels, perhaps their programmes, their materials and memberships lines and things and then you can learn how you want to do yours and how you might want to do them differently. So, absolutely put aside budget and time for training, coaching, learning. And again, it can be also early days, free materials, but do you make sure that you’re getting quality and per to not just… The free stuff isn’t necessarily the best, I suppose, I would say.

Now one question, or comment, was: I’m not so comfortable with the online interaction. I really love face-to-face the in-person real people, real talk kind of workshop scenario.

And although I do offer that, one-day workshop now, as some of you will know, I now have a young daughter and the practicalities of having a one-day workshop isn’t necessarily as it was before.

However, more than that, I want to reassure you and I’m sure you will find this when you experience it through yourself, that the online interaction is incredibly rich and effective. It’s practical in the sense that you don’t have to travel. So, you miss the commute, you can listen on your commute. In fact, you can, read the materials on the train journey. You can listen to the audios while you’re doing the dishes you can call in over your lunch break and so on, right?

So from a practical perspective, it’s incredible. And if any of you have been part of the various workshops and challenges I’ve done in the group, if you have been part of the programmes, and in fact some past clients would say this, there is an incredible energy and dynamic and really productive sense of making progress through even those quick short workshops that we do for one week. And you can imagine then what you can get out of a programme where you’re interacting with the same group of people, really supporting each other, learning from each other and working through the membership site at your own pace.

So, I would definitely recommend trying the online interaction and sampling it, maybe joining one of my free workshops over in the Facebook group, for example, or watching the YouTube videos. And above all, I think if you’re going to be running a business most of us, even those who are going to be more traditional brick and mortar businesses will want to have an online element. So, I think getting really comfortable with that both as an individual, but also as a business person will be absolutely critical.

Speaking of that online interaction, another question came in about how logistically it all works.

And if you go back to last week’s episode, you’ll hear about all the content and the things that are included. However, to give you a bit more detail of the practicalities of it, the three key elements of the programme are the membership sites. So, again, the comprehensive 12-month programme and therefore 12 modules, there’s a new module every month.

*UPDATE 2020: the programme has been re-shaped into five modules to cover the five pillars of a sustainable business.*

The membership site is something that you get access to when you join, of course, and you will then be able to dig into audios, videos and PDF worksheets that are each a building on the previous module. You have access to all these materials from the get-go. So, you’re not going to be drip-fed and the things he can depend to the bits that are most important for you. However, I would always recommend, of course, starting with the beginning of Re-imagining Success, looking at that big vision, working through mindsets and so on.

So, the membership site is really the heart of the programme. That’s where the materials are for you to work through at your own pace. On top of that, however, you have weekly coaching and the past we were doing fortnightly. Now, you have a weekly hour-long group coaching session where you can turn up. And of course, if you turn up every week, then you’ll get very comprehensive, effective, massive leaps, forwards from not only working through the materials yourself, but also getting on the phone with me. Getting essentially customised one-on-one, tailored feedback and coaching on the particular situation that you’re in and on your version of when we get to those pieces, the business strategies and so on.

And so that, of course, is a really important element of it really getting that live coaching. And that takes place on UberConference. It’s a conference line where you can log in for free on a computer, or you can dial in and the local conference number and that’s all free on the website or it’s a local number for you and your country and it’s audio. And that will then record. And we’ll upload that to the site afterwards. If you can’t join, you can always listen to the recording as well.

And then the final elements, for those of you who are on Facebook. I know some of you aren’t any more or never have been. And the Facebook certainly for me is still playing a role in my business. And I think it is the best form at the moment for having this membership community. And so, we’ll have a private Facebook group there for the members of the programme where you can ask your questions between the coaching sessions, get feedback from other members of the group, get feedback from me. And of course, I can hop on there and do some extra lives and trainings there as well.

A few more questions. So, one was around, people seem to be in different stages of the process, how do you handle that?

And the only thing I can say is that it has worked, so far, and it is true that some of you might be at the very beginning of the process. You don’t yet know what you want to do, and you’re going to be really spending more time at that beginning exploratory phase. And then some people perhaps already have a business idea, and you’re really looking more for the nitty-gritty business and marketing piece.

It’s still incredibly valuable for everybody to go back to the beginning and look at the visions, spend that time, getting clear on who you are, your values, your vision, both for your life and for your business. And even those of you who are at the beginning of the journey will benefit from hearing what those of you who might be a bit more advanced are working on in terms of business and marketing and websites and so on. So, I think it really feeds into itself and really builds on each other.

And all of you will really benefit from listening to others. If you can stay for the full hour of coaching, then you can really learn from other people as well.

Now there have been a lot of questions around marketing in terms of what do you do when you have too many clients, how do you do referrals? And, let’s see what else, which social media platforms should I be using? How do you outsource and so on?

And these are all things that are very much covered in the programme. So, as much as I talk around the vision and the mindsets and so on, the core business content is absolutely there.

And as you may know, my background is in branding and marketing, from one of the best really companies in the industry. So Proctor & Gamble really known for almost inventing the brand. They certainly amended the soap opera in fact, back in the day. So, that’s where I had my really foundational training in terms of building quality brands. I worked on a range of brands from lower-end Point of Market Entry brands, right through to high-end luxury brands.

So, I really have the range of knowledge there both from design roles, working on concepts and more the visual side and advertising and creative side, right through to the commercial and operations side, media planning and so on, I now mentor startups and entrepreneurs as well. And as I mentioned a few minutes ago, I do a lot of writing and training in the latest trends and best practises of digital marketing and business. And of course I have my own business. So, hopefully that gives you a bit of an idea of where I’m coming from, in terms of my knowledge, both from the big brand, big budget, big corporation side of things, right down to the small startup entrepreneurs, solopreneurs side as well.

In terms of the business content, just to mention that as well in the programme we really get into in the second portion of the programme. So, the first portion is really around exploring your options, narrowing down, filtering, and making a decision. The second part is really where you’re going to grab your business idea and run with it. So, we’ll be looking at understanding your clients, choosing the right business model, building your brand, and really making it work for you. So, things like the value proposition, canvas.

The wants, fears and needs of your customers, the benefits, the results you’re providing with your products and services. The business model canvas and by the way, I have my own versions of these. So, these are phrases you may have come across. There are various versions of these out there on the internet, and I’ve tweaked those with my experience from P&G and my own experience with solopreneurs as well to make it more relevant to us.

So, everything from the customer, the problem you’re solving your solution and why you’re credible in delivering that solution, the exact pyramid of services you’re going to be offering from the free attraction marketing kind of services, right up to the pinnacle, the VIP, the high-level, perhaps one-on-one coaching, let’s say in your case. And marketing, how you’re going to reach your audience, how you’re going to track those people. And what you need to invest and the support you need and so on.

Content strategy, one of my favourite things from P&G again, I already had up a pioneering piece of work really with the media agencies with YouTube, with Google on defining the content strategy. Content really sits at the sweet spot between what your audience, what your clients, what your customers, what your ideal people that you’re going to be working with are looking for what they want to know, what they need to know on the one hand.

But also then the other side of the coin is what your brand stands for. And the sweet spot between those two is really where you’re going to choose the themes you want to talk about the formats, the types of content, and then choosing the right channels. And then finally, we’ll also look at the latest trends. So, if you are interested in innovating and staying in touch with the latest, we are going to be covering that, whether it’s things like videos really big at the moment, again, at the time of recording might create content.

So, things like stories and little pieces of texts and posts and short form, as well as audio smart speaker marketing, and we’ll even get into the detail of helping you with your LinkedIn profile, setting up your Facebook page and Instagram accounts and so on. And so very comprehensive, very solid foundations of business, getting up to speed, getting your business off the ground, right from the very beginning.

And the final question I’ll close with is, would you ever go back to corporate consulting, contracting?

And I think that’s a great question. And I have to say, I cannot imagine ever going back to corporates. And I know a lots of people who did go back and I think perhaps for the wrong reasons, or perhaps they left for the wrong reasons, they were very naive and thinking that their business idea was the next Uber, Airbnb, whatever. And they were very disappointed when it was much harder than they realised that it didn’t go so well. Or perhaps they missed the team, the social side of work, they missed the accountability, the support from senior bosses and so on.

And I think in that scenario actually, it’s very possible to set up and I believe that and I think we should do that. Set up a business that’s going to work for us in terms of having the social side. You can create a team if you want to have a team, you can go to a coworking space if you miss that social side of things, there are ways in which you can set up your business. You can have a co-founder for example. And so, really making sure you’re designing the business to work for you is what’s going to make it sustainable.

And in my case, that’s what I’m doing. It is evolving with time. I am re-imagining success for myself personally and in the business as we go. And that does change over time. And but absolutely I couldn’t imagine at the moment, never say never, but right now, I can’t imagine going back to sort of the Monday to Friday, so-called nine to five, which of course never is nine to five. Travelling, commuting into an office. I always feel a bit of a freak when I’m in the city.

And I remember even years ago when I travelled in for a meeting, which I tried to avoid as much as possible, I must admit. But I was going against the tide. I think I was wearing a bright blue coat. As I remember everyone else was wearing black and grey. They’re all heads down, looking at their phones, looking miserable. And I was sort of humming along, a little bit sad that I had to be there in the city and at that time of day in the rush hour, but much more radiant I’d say.

And very much standing out in a field, in a pool, in a whatever you want to call it sort of black and grey and that corporate conveyor belt going in one direction. So, no, I don’t think I’d ever go back. I love what I’m doing and I really believe that you can too. So, I think I’ll leave it there. I think I’ve actually talked for longer than I usually do, because there were so many questions that I wanted to cover. If there are any questions I haven’t covered, if you have anything as well based on what I shared last week, or having a look at the sales page, again, onestepoutside.com forward slash nine to five, has all the details of the programme.

Then do, let me know. You can get in touch at podcast@onestepoutside.com and I’d be happy to answer any questions you have and make sure that you’re making the right decision for you at this moment in time. So, I’d love to work with you. I would love to take this step with you and follow along, support you through your journey. And I can’t wait to get started. Thanks so much for listening and I’ll see you next week. Bye for now.


Let us help you design a business and a life that gives you freedom from the 9 to 5. There are several options for how you can work with us. Choose the programme that’s right for you.

The Outsiders Business Incubator

A year-long business incubator for experienced corporate professionals who want to translate their skills and passions into a profitable and fulfilling business. onestepoutside.com/9to5

The Outsiders Business Accelerator

An ongoing mastermind for service-based business owners, freelancers and online entrepreneurs who are ready to achieve success on their own terms. onestepoutside.com/accelerate

The Outsiders Business Academy

A self-paced course for you to work through in your own time, to learn – and implement – the foundations of building a profitable business that lets you escape the 9 to 5. onestepoutside.com/course

1:1 Coaching & Mentoring

If you’re looking for one-to-one support to help you achieve your specific life and business goals, Anna has a limited number of spots for individual coaching and mentoring. onestepoutside.com/course 

The Outsiders Business Incubator

A mentoring programme focused on implementation support and accountability to help you grow your expert business faster – without sacrificing your personal life to do so.


You might also like

“Everything you’ve ever
wanted is one step outside
your comfort zone.”

Book a free consultation

Get on the phone with Anna to discuss your unique goals and situation to determine the best programme for you, so you can start taking action towards creating the business and lifestyle you desire.

Get a free assessment of your business

Download this scorecard to review where you are on each of the 5 pillars of building a life outside of the 9 to 5, and get clear action steps to help you fill the gaps.

We will use and protect your data in accordance with our Privacy Policy.

Looking to grow your expert business?

Download this FREE Business Assessment to identify the gaps that are preventing your growth so that you can take actionable steps towards building a more successful and sustainable business.

We will use and protect your data in accordance with our Privacy Policy.

Download the brochure

Find out more about our flagship mentoring programme for experienced professionals who want to translate their skills and experience into a profitable business that brings them more freedom, flexibility, and fulfilment.

We will use and protect your data in accordance with our Privacy Policy.

Privacy Policy

This privacy policy sets out how One Step Outside uses and protects any information that you give One Step Outside when you use this website (https://onestepoutside.com/).

One Step Outside is committed to ensuring that your privacy is protected. Should we ask you to provide certain information by which you can be identified when using this website, then you can be assured that it will only be used in accordance with this privacy statement.

One Step Outside may change this policy from time to time by updating this page. You should check this page from time to time to ensure that you are happy with any changes.

What information we collect and why

We only ever collect the information that we need in order to serve you.

Generally, this just means collecting your first name and email address that you enter, for example, when you request a resource, register for a webinar, or submit a message via a contact form.

If you are a paying customer, we also collect your billing information including your last name and your postal address.


When visitors leave comments on the site we collect the data shown in the comments form, and also the visitor’s IP address and browser user agent string to help spam detection.

An anonymised string created from your email address (also called a hash) may be provided to the Gravatar service to see if you are using it. The Gravatar service privacy policy is available here: https://automattic.com/privacy/. After approval of your comment, your profile picture is visible to the public in the context of your comment.

Contact forms

We use Gravity Forms to allow you to contact us via the website. We will use the information you submit for the sole purpose of that specific form and will explicitly ask you to provide your consent to allow us to do so.

Embedded content from other websites

Articles on this site may include embedded content (e.g. videos, images, articles, etc.). Embedded content from other websites behaves in the exact same way as if the visitor has visited the other website.

These websites may collect data about you, use cookies, embed additional third-party tracking, and monitor your interaction with that embedded content, including tracking your interaction with the embedded content if you have an account and are logged in to that website.

Advertising and Analytics


We use Google Analytics to track and optimise performance on this site as well as embedding video content from YouTube, and this means that your web browser automatically sends certain information to Google. This includes the URL of the page that you’re visiting and your IP address. Google may also set cookies on your browser or read cookies that are already there. Apps that use Google advertising services also share information with Google, such as the name of the app and a unique identifier for advertising.

Google uses the information shared by sites and apps to deliver our services, maintain and improve them, develop new services, measure the effectiveness of advertising, protect against fraud and abuse and personalise content and ads that you see on Google and on our partners’ sites and apps. See their Privacy Policy to learn more about how they process data for each of these purposes, and their Advertising page for more about Google ads, how your information is used in the context of advertising and how long Google stores this information.


We use the conversion tracking and custom audiences via the Facebook pixel on our website. This allows user behaviour to be tracked after they have been redirected to our website by clicking on a Facebook ad and enables us to measure the effectiveness of our Facebook ads. The data collected in this way is anonymous to us, i.e. we do not see the personal data of individual users. However, this data is stored and processed by Facebook, who may link this information to your Facebook account and also use it for its own promotional purposes, in accordance with Facebook’s Data Usage Policy https://www.facebook.com/about/privacy/.

You can allow Facebook and its partners to place ads on and off Facebook. A cookie may also be stored on your computer for these purposes. You can revoke your permission directly on Facebook here: https://www.facebook.com/ads/preferences/?entry_product=ad_settings_screen. For more guidance on opting out you can also consult http://www.aboutads.info/choices.

Who we share your data with

We use a number of third parties to provide us with services which are necessary to run our business or to assist us with running our business and who process your information for us on our behalf. These include a hosting and email provider (Siteground), mailing list provider (GetResponse), and a payment provider (Stripe).

Your information will be shared with these service providers only where necessary to enable us to run our business.

How long we maintain your data

If you leave a comment, the comment and its metadata are retained indefinitely. This is so we can recognise and approve any follow-up comments automatically instead of holding them in a moderation queue.

For users that register on our website, we also store the personal information they provide in their user profile. All users can see, edit, or delete their personal information at any time (except they cannot change their username). Website administrators can also see and edit that information.

The main reason for collecting this information is to be able to send you resources, updates and, sometimes, information and products and services, as well as for internal record keeping.

The rights you have over your data

If you have an account on this site, or have left comments, you can request to receive an exported file of the personal data we hold about you, including any data you have provided to us. You can also request that we erase any personal data we hold about you. This does not include any data we are obliged to keep for administrative, legal, or security purposes.

How we protect your data

We are committed to ensuring that your information is secure.

Where we have given you (or where you have chosen) a password that lets you access certain parts of our site, you are responsible for keeping this password confidential and we ask you not to share a password with anyone.

Unfortunately, the transmission of information via the internet is not completely secure. Although we will do our best to protect your personal data, we cannot guarantee the security of your data transmitted to our site; any transmission is at your own risk. Once we have received your information, we will use strict procedures and security features to try to prevent unauthorised access.

Links to other websites

Our website contains links to other websites. This privacy policy only applies to this website so once you have used these links to leave our site, you should note that we do not have any control over that other website. You should exercise caution and look at the privacy statement applicable to the website in question.

Changes to our privacy policy

We keep our privacy policy under regular review. Initially created on 18th November 2016, it was last updated on 23rd May 2018 to be compliant with GDPR.

Contact information

If you have any questions or concerns related to your privacy, you can get in touch here >>