Ep. 150 Alternatives to a 9 to 5 job

150 Alternatives to the 9 to 5

In this week’s podcast, Anna celebrates 3 years since the publication of her book with a look at the alternatives to a 9 to 5 job

The book Leaving the Corporate 9 to 5 looks at 5 alternative career paths – changing sector, going freelance, starting your own business, creating a portfolio career, or taking a leap of faith into the unknown – along with the advantages and disadvantages of each.

*Resources mentioned during the episode*

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 to a 9 to 5 job. www.leavingthecorporate9to5.com 

10 steps to quitting your job to work for yourself

This roadmap gives you an overview of the most important things that you need to consider so that you avoid some of the most common pitfalls and start thinking practically about how you’re going to make this escape happen.


Alternatives to a 9 to 5 job


Hello there, and welcome back to the Reimagining Success Podcast. I’m your host Anna Lundberg, and this week we’re celebrating three years since the initial publication of my book, Leaving The Corporate 9 To 5, Stories From People Who’ve Done It And How You Can Too. Now, this was a massive personal achievement for me, as of course it would be, to produce a book, and I am holding it in my hand right now. It still gives me goosebumps and certainly a level of joy, that I’ve created this. But more importantly, it’s played an important part of my business, Funnel, as it were. It’s an entry into my ecosystem, using all these lovely marketing terms.

It’s a low-cost product that clients or prospective clients, would-be clients, can buy from me. I’ve been able to give it out as a prize in challenges that we run on our Facebook group, and most of all, I hope it’s a valuable resource. It still stands the test of time, it’s not that old, it’s absolutely timeless. So it’s 50 stories of people who’ve quit their job to do something else, which I’ll talk about in a moment.

And although the individuals inevitably will have moved on in some way, they’re shaping their business in a different way. In a couple of cases actually I know, having reconsidered and rejoined the so-called nine to five in some shape or form. And certainly the ones who didn’t know what they were doing five, six, seven years ago, have found their calling or a calling, and made incredible progress and an amazing impact since then.

So if you don’t have your copy, of course the first thing I should say is, Leaving The Corporate Nine To Five, you can get it at leavingthecorporateninetofive.com. Click through there on my website, or you can search for it on your local Amazon site. And it is available in, I was going to say Kindle is the one, Ebook form, and paperback. And in fact, no I lie, it’s now available as of this year in hardback, so you’ve got three formats to choose from. We haven’t yet done the audio book. I have this aspiration to have different people voicing the stories, because of course it’s not my story, it’s the story of these 50 people. But for now, you’ve got the three, paperback, hardback and Kindle version to use in the meantime. Plenty of options for you.

So what I thought I’d do today, obviously assuming that you’ve now already gone on and clicked to buy your chosen format of the book, I thought I’d look into what the alternative to the nine to five is.

Now, this is a chapter in the book, before I get into the 50 stories, but it’s also something that we’ve been talking about for the last few weeks in fact in the context of the great resignation, all these millions of people sort of quitting their jobs all around the world, and something that maybe you’re considering and certainly I’m thinking even more about from a deeper perspective as we go, as to what is the alternative to this very old construct of the nine to five.

And of course in the last year or so through the pandemic, we’ve had to reconsider how things have worked, lots of offline in-person businesses have had to go, which I think is a good thing, online. There’s this idea of hybrid work, hybrid offices now, flexible working has grown, so lots of really positive trends. But I think it’s an interesting thing to think about, if not the nine to five then what, right?

So first of all, I want to talk through what I mean by the nine to five, the conventional nine to five as I would call it. So for me I’d include the following parameters, and hopefully this makes sense. I’d be interested to hear what you would define this as as well, because of course this is a concept that Dolly Parton and many of us have understood to mean something in particular for quite some time now, certainly the last 50, 60, 70 years.

So for me, it’s working at a private corporation, and the primary motivation of that company is profit. And in a way, you’re sort of a small cog in a big machine. That’s one of the big drivers of what I mean by the corporate nine to five.

You’re working in an office-type environment, and that’s interesting now, that’s something I’ll have to reevaluate given the changes, but certainly that’s traditionally what we’ve seen to be part of that corporate nine to five. You’re reporting to a boss, a manager. You’re working standard hours, pretty much Monday to Friday. Obviously it was traditionally nine to five, but now we do longer days. Thanks to tech, we can work from home, evenings, weekends, and so on.

And then finally, really important of course, which is both an advantage and a disadvantage in some cases, receiving that regular salary. And other benefits like health insurance and a pension and so on. So that’s what I mean by the corporate nine to five. Private corporation, you’re a small cog big machine, office-type environment, you have a manager telling you what to do effectively and deciding on your promotions and so on, you’re working those kind of standard hours, it’s a traditional structure I suppose, and then you’re receiving that regular salary.

So in terms of alternatives to a 9 to 5 job, that could mean you could break it down. Number one, working in a different type of company or organisation, right, that has different motivations where it’s not profit, not-for-profit, so that’s suggests already a non-profit organisation or charity. Working from home or in another non-office environment. Of course, that’s again something that’s become very topical recently. Working for yourself, or for a number of different clients rather than just having that one boss. Working A-typical hours, hopefully that you can choose yourself would be the main thing, not just working night shift for the sake of it. And then no longer in fact receiving that regular salary and benefits, which means that you’re in control of your income. There’s no ceiling as there is on a salary, but of course it also means that you’re then responsible for bringing it in. You don’t get the money regardless, you actually have to do the work and build the business.

So I wanted to look at a few of the main alternatives to a 9 to 5 job that I do go into, and that’s how the book is structured in fact.

So again, Leaving The Corporate Nine To Five. The first section is, people in fact are moving into a different sector. So it’s not something that I focus on as much, I focus really more on going freelance and starting a business and so on. But in a way, the least dramatic change from a corporate nine to five, would be sort of a non-corporate nine to five, right? So keeping the rest of the environment more or less the same. Going from private to public, moving maybe to a more creative industry. Maybe agency side instead of client side. Joining an existing startup or so on, right?

So you’d still maintain the office environment more or less, you’d have a boss, you’d work kind of those standard hours still, and you’d still get your paycheck, but you’re in a different industry, maybe with different motivations and values of the organisation, right? And it could be that that change is enough to get you motivated again, especially if you’ve moved towards what we talk about, the icky guide, the purpose, a cause that you’re already passionate about. Not to mention the fact that you’ll be learning new skills, there’ll be a steeper learning curve, and that’s really exciting is that new challenge so many of us are after, and yet you’ll still have the familiarity and the comfort of working in a more or less similar way.

And you’ll still have that regular, maybe lower, salary. But nonetheless, that regular salary coming into your bank account, unless you’ve gone for a sort of an early stage startup where it might be a bit riskier. But of course, the advantages are also the disadvantages, because that familiarity and comfort of keeping so much the same, means that you might not be addressing the underlying problem and the frustration you’ve been feeling.

So that’s moving different sector, the next one is going freelance. So it’s a really attractive alternative, and something that a lot of us go into either as a transition, or as a longterm gig as it were, pun sort of intended. So you’ll be usually working for several clients on different projects, so you have the excitement and the variety. You’re especially common in the creative and media industry, but also of course writers, designers, web developers, social media managers, photographers, and so on. There’s some subtleties in terms of IT in particular, we have contractors, consulting is sort of another variant.

There’s of course the digital nomad phenomenon of being location dependent and so on, and they could be freelancers, or contractors or entrepreneurs for that matter.

But essentially, freelancing, using quite a broad term there, is providing that service on an independent basis. So lots of advantages again, you can choose clients and projects, you can work from home, you don’t have to commute, you don’t have a boss as such, in a way you have several bosses. You can adjust your workload, you can say, “Hey, I’m going on holiday.” You can manage your time, right? And importantly, you can decide on your own rates. If you want more money one month, you can take on more clients. If you want to take a holiday, you can take on fewer clients.

Disadvantages, it can be hard especially when you’re starting out, to set those boundaries. We talked about that a few weeks ago on the podcast, saying no to clients. And most likely, especially in transition, you will end up working with similar clients to the company where you were working before. So if you didn’t want to work with those private corporations, that’s not ideal. You may still have to travel to client’s offices. Working from home of course comes with it’s own challenges. And again, as I said, you don’t have a boss, but you will still be reporting to your clients, so in a way you’ll have several bosses.

And in practise, although we say we can adjust our workload if we want to go on holiday, or we want more money, especially when we’re starting out, there is this kind of feast or famine scenario, the rollercoaster, that we either have too much work one day, or we have too little the next day. And that’s something that we need to really smartly handle in terms of business models, and so on. And then, a lot of clients might have, in particular some industries, standard rates you can’t negotiate, you find it stressful to do so anyway, and you’ll always have pressure from clients to discount your prices, right? So there can be some disadvantages in freelancing too.

The next one would be more the entrepreneurial, the pure entrepreneurial I suppose, whether you’re a solo preneur running your own show, or you have one or more co-founders, or you’re building a team. And to be honest, I see a freelancer as being an entrepreneur too, so it’s sort of a fine line, but I guess a business is more around systems, and automation, and having something that’s separate to you. In the U.K. you’d have a limited company, rather than having your personal self-assessment and being a sole trader as it were. So that’s sort of the legal and financial distinction.

And as an entrepreneur launching your own business, you can choose what problem you’re going to solve, what sector you want to work in, which clients you want to work with. You can definitely work from anywhere if you want to, depending on the business model you choose. You are your own boss, you choose your own hours, you set your own prices, right? And then all the profit goes to you, unless you have the, and I think of sort of bootstrapping your own business, so I’m not talking about getting external investment and investors, and shareholders and so on.

Of course, as with freelancing, it may be that you have the most skills and expertise in the area you were working before, which means that you’ll still be where you perhaps wanted to leave. If you do start in a new field, that brings its own challenges, because you may well be starting more or less from scratch, right? In theory, you can work from anywhere, but it can feel quite lonely to be by yourself. And of course if you launch a physical product business for the brick and mortar store, you will be tied to that location at least in the short term.

You’re your own boss, which is an advantage and a disadvantage. It means that you don’t have someone to support you, you’ve got to make all your decisions yourself, and that can be quite stressful. Probably in the shorter term, you will be working longer hours in fact, so that’s the whole social media meme about, I’m now working longer than I was in my corporate job, and those lines between work and personal life will become very blurred. And then look, you can get a business up and running without having to have that huge investment. You can just put up a website, you can chat to people, you can develop a great business quite easily, as it were.

The reality is, you’re unlikely unless you’re very lucky, to be bringing in a whole lot of money and replacing your salary right away, right? So generally we say you’re lucky if you break even your first year, if it’s a product business it can take three years to break even. So it’s just being a bit realistic.

The final option I want to talk about, is creating a portfolio career, and this may well be my favourite, because it basically means you’re doing some combination of those options, right? So it’s really a great proposition for people like myself, and I’m sure like you, who are multi-passionate Renaissance men and women like Leonardo Di Vinci, lots of talents, interests, and we can’t quite settle on one type of work to focus on. If nothing else, it’s a great transition. So for example, I might continue with marketing consulting, because I’ve been doing marketing in my corporate job for those types of clients on the one hand, but then in parallel I’m building my true passion business, so in my case more of the coaching, writing, speaking side.

So lots of advantages. You can really find a great match you can bring to the fore your different skills and interests, have different roles, different sectors. So lots of variety, really bringing to life the different aspects of your personality. Potentially, you can work from anywhere, at least in a variety of different locations. You are your own boss, you can work flexibly, and again, you set your own rates. And having a portfolio of different roles and jobs, also means that you have a more diversified income, so if one area has a bit of dip, you can compensate with the other.

Again though, if you have that portfolio, probably one of the jobs in your portfolio will be directly connected to a similar role in the sector as before, so you won’t have the clean break that you might be after. It can end up having several jobs, because you’re running back and forth between different clients, different locations, you might need to have different social media platforms for you content for different audiences. You may still have a boss or clients to report to, depending on the type of portfolio you develop. Lots of more complexity. And again, you might not have a lot of steady income, at least in the beginning.

So those are the options in terms of looking at alternatives to a 9 to 5 job…

Moving into a different sector, so keeping more or less everything the same just moving into creative, or different kind of environment, non-profit perhaps. Freelancing, launch your own business and creating a portfolio career. And coming back to the book, the final category, the final sectio in the book, is actually taking a leap of faith. Now, this is perhaps not a longterm strategy or alternative to the nine to five, but it is the, hey, just taking some time off, enjoying the freedom of leaving the nine to five, and then exploring what you might want to do instead.

That is a very real option, especially if you’re perhaps untied to a massive mortgage and children or so. Maybe your children have… you’re an empty nester now, they’ve moved on. Maybe you’re at the beginning of that journey like I was, single with a sort of very cheap rental flat that I could easily get rid of, no car, no kids and so on. But taking a leap of faith means of course, you can say goodbye to your job today if you want to, assuming you have the savings and so on, the safety net. You can travel the world, you can rest, you can learn, you can do whatever you want. Complete control of your schedule, plenty of time and energy by the way to work out what you want to do, and then to actually start building that business. And taking on new opportunities as and when they present themselves.

However, pretty obvious, you’re not going to have an income coming in right away, so you will either need to make some big compromises when it comes to your life, or you’ll make a big dent in your savings, and that can be quite stressful. The initial euphoria that you have, the enthusiasm, can soon be replaced by panic as you begin to struggle to decide on what it is you do want to do, and, “Oh, is it going to work out? Oh my goodness, do I have to get another job?”

Ironically, and I certainly found this, I was less productive when I had all those weeks and months stretching ahead of me without any structure, right? So you do need deadlines, structure, support, to make sure that you’re not just letting months and years pass without getting anything done. You may unfortunately again, be tempted to take on work that you don’t want to do, or even going back to that full-time job. And again, it does take time, so in the meantime there’ll be a lot of uncertainty. So that is a bit of a risky proposition, in terms of just taking the leap of faith, but it’s certainly a possibility. It’s something that I, to be honest, pretty much did and many people in the book did too.

So of course, in terms of which alternative is right for you, it depends on your goals, what success looks like for you, but I hope I’ve opened up your mind to different possibilities that are out there, and also helped you to consider more seriously the advantages and disadvantages so you can work out what might be the best fit for your goals and priorities.

So again, that’s sort of the beginning section of the book, Leaving the Corporate 9 to 5. We’re celebrating three years this week. 3rd of October, 2018 was when we published it last… well, three years ago in fact. It was my birthday, still is my birthday, 3rd of October, and divided into these five sections of alternatives to a 9 to 5 job. So do grab your copy if you haven’t already got it, I’d love to hear your feedback. And of course if you have read it, please do leave a review, it helps me, it helps people like you find the book as well. And I hope it is valuable to you as you consider leaving the corporate nine to five.

Thanks so much for listening. Happy three years to the book, and hopefully you can join us in the next edition of the book with your escape story, I’d love to have you. Thanks so much for listening, I’ll see you next week. Bye for now.

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.


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/coaching


Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

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 >>