Episode 310 – Living in the Grey: Exploring the spectrum of career possibilities

In this week’s episode, Anna challenges the common dichotomies we often face professionally. Why must we choose between a toxic corporate job with a steady salary and the freedom of entrepreneurship with financial uncertainty? Drawing inspiration from “Emily in Paris” and a recent LinkedIn post, Anna explores the rich, nuanced spectrum that exists between these extremes. Reflecting on her own journey—from a successful corporate career to becoming a digital nomad and an entrepreneur—Anna emphasises the importance of redefining success and embracing the “grey area” where diverse possibilities exist. Join Anna as she debunks unhelpful myths, encourages creative thinking, and inspires you to design a career that truly aligns with your unique aspirations and life circumstances. Let’s dive into this multicoloured world of potential and reimagine what success can look like for you.

*Resources mentioned during the episode*
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. www.onestepoutside.com/coaching

Career Possibilities

Why does it always have to be either or? Why does it have to be EITHER you work in corporate, you have a toxic work culture, a terrible boss, no freedom, no flexibility, OR you’re free and loving life, but not earning money. Why do you have to either be a hustling entrepreneur who works harder than you did in corporate, living the exciting life, or you have a stable, dull, regular nine to five? Why do we have to choose between freedom and salary, between meaning and money, between working in an office and working flexibly? Why can’t we, as Emily in Paris would put it, live in the grey area? There is so much richness in the nuances that live in between these extremes. I was inspired partly by Emily in Paris, but more so by a post on LinkedIn, I have to admit, to reflect on this topic, and the more I think about it, the more I get passionate about it. For those of you who perhaps don’t know me, if you’re new to the podcast, if you’re new to my platform, I started in corporate, loved my work, worked in a fantastic organisation. So many doors have been opened thanks to that network, the schooling that I got there, and that was an amazing experience. However, it wasn’t where I saw myself going forward. So in 2013 I left. In my initial years I did consulting for corporate clients and travelled in between.

I then discovered coaching and I was really working for myself while doing the digital nomad thing. I was young and single and carefree, so I was travelling the world while trying to build my business and blogging and doing calls and so on virtually before that became as mainstream as I suppose it has. Because of the pandemic, I have always continued to work with companies running workshops, largely virtually partly because of my own desire for that flexibility. And then, of course, Covid. And in later years, then because I have young children, more in person happening now, but different workshops, executive coaching. I also am doing more speaking now, which is in person, which is really exciting. I’m working even more with corporates and partnering with them because there is so much interesting work happening in this grey area. Or I would like to call it the rainbow world of unicorns and magic.

No, but it’s a. It’s a multicoloured spectrum of different possibilities, different constellations that I have explored, that I will continue to explore. I’ve seen clients, and again, if you don’t know me, my initial business proposition, and which has carried through my two books that I’ve published, are really around helping professionals in corporate careers transition out of that world, out of the so called nine to five and into working for themselves. My belief has been that that has been the right decision for me. When people therefore come to me and are exploring that too, I support them in that and I believe that for some of us that is an amazing proposition and there is a way to get that balance. Right now we’re twisting different knobs, calibrating, moving the sliders all the time. It evolves. Our definition of success evolves.

Mine has changed since I was single and ten plus years younger, without a partner, a house, a family. And I went through an adventure phase where I was travelling and doing all sorts of exciting things around the world. I went through a phase when I was very much tied to breastfeeding and being at home and so on. Again, we had the pandemic and now I’m in a new phase as well, where I’m doing a bit more travel. My kids are both Monday to Friday and I’m exploring this again. Grey area Rainbow World of collaboration integration synergies between the organisation, space and I, so called entrepreneurship. We always focus on this. We have this binary thinking where we believe as individuals, we have to make a choice between a corporate job or entrepreneurship, between being five days in the office and fully remote, between having freedom or security, between making a difference and doing meaningful work or.

And earning decent living. And these dichotomies, they’re not only inaccurate, but they’re also not helpful. They’re not helpful beliefs or frameworks for us as we go about pursuing a fulfilling career in life. It’s just not constructive, it’s not valid, it is not helpful to think in those terms. It makes it incredibly stressful for me if I am today, and I always paint the extreme picture in a terrible job and my boss is awful, the organisation, it’s all, you know, so clear that I need to leave there. But then the prospect that faces me is to leave behind all security, my entire salary, and go and live in a van somewhere and, you know, not be able to send my kids to school anymore, not be able to travel, I have to sell my house, etcetera. Now there are people, and certainly in the early days of doing this work, I was with a lot of younger people especially, but all ages again, all different generations and phases of life, who chose to live that simpler life. And I think there’s so much joy and value to be found in that.

And freeing yourself from the ties of mortgages and Range Rovers and luxury handbags and so on, no judgement. I like these things too. However, you don’t have to do that. Right. And in the presenting yourself with those, that really stark choice between either I can put food on the table for my family, but I have to stay in this terrible, toxic finance job, or I need to throw caution to the wind and, you know, we’re gonna have to live in a tent, the kids won’t be able to eat and I’ll have to, you know, I will be happy, but I have to give everything else up. Then of course that decision is going to be hard. The post I saw on LinkedIn was talking about, and I don’t think I went into the detail at the beginning of the episode about this, was talking about how not everyone should be an entrepreneur. Some people should be an employee.

And I would agree with that. Whatever should means, it is an individual choice based on your life circumstances, your goals, your personal preferences, your finances, your interests, the state of the economy, etcetera, etcetera. There are so many factors, but what’s exciting is, and also maybe a bit scary, and I always say scary and exciting come together, that we have the opportunity to design, to create something that’s really unique to us again, that will evolve over time in the world of working for yourself. And I’m doing quotation marks, but you can’t see me. You could put that into buckets of freelancing, consulting, contracting, having a portfolio career, by the way, with multiple income streams, having a service based business or a product based business, being an expert, being a coach, being a consultant. So even within that, oh, I’m working for myself, there is a huge spectrum, a range of different constellations of stress and finances, different sectors, different industries, and we can do different types of work and earn a lot of money. We could do the same type of work and earn less money. And it’s, there’s so, so many factors, right? And we have to decide what is important to us, the what always before the how, and then we can look at, okay, how might I go about creating that? So, of course, it starts with, as always for me, redefining what success looks like.

Success is not either progressing on the linear corporate ladder in an organisation and becoming CEO, or having a VC funded startup that you sell to a big corporation, Google or whatever, further down the line and make millions. It’s not either, you know, working on the beach with your laptop in, in tow with a pina colada, or travelling in commuting to London. As we’ve seen, partly thanks to the pandemic, many more of us are opening our eyes. Sadly, some are closing them again. But to the possibility of more flexible work arrangements. There are most importantly, I’d say, more leaders and managers who are empathetic, who role model and who believe in the importance of taking care of your health, putting family first, organisations have more people first strategies. I’m a huge believer and proponent of human first, human designed more human workplaces, environments, organisations. And there’s a hugely exciting thing happening right now because of the pandemic, because of AI coming under the scene, and because of these kind of tectonic plates shifting.

And I think we can choose to be part of that. And I struggle sometimes myself, or I say often with this podcast if we’re going to get very meta. And the work I do, because I work with individuals, business owners, experts, and my books are called leaving the corporate nine to five, outside the nine to five. And I do a lot of work and I love the work and I think it’s valuable work, meaningful work with organisations. When it comes to those empathetic leaders, motivated employees, people first, businesses, that is possible. I can have those different hats, I can be a coach and a speaker, I can do training workshops sometimes and sometimes do more of the keynote type of engagement. I can work online and I can work offline. It’s not about complicating things with a business model that suddenly makes me have to do everything and dilute my message and so on.

But as long as it makes sense to me and to people I work with, that’s what matters. Other people looking at me might, you know, if they see everything on a list, they might say, oh, that’s strange. What are you actually an expert in? What do you do? But for the people I work with, it all makes sense. And most importantly, it makes sense for me. So redefining what success looks like and then, you know, doing away with these myths, because they are myths that you can’t make good money if you’re doing something meaningful, or likewise that corporate jobs are inherently evil, right? I have my own personal anecdotes, client stories, so many examples that would challenge any of those beliefs and myths that are out there, right? So you choose what you want to believe and go forth and find the examples that will support that belief and you’ll be surprised, or maybe not. So how many examples you will find of people creating their own unique path, having squiggly careers, having portfolio careers, being multi potential like multi passionate renaissance men and women, generalists, whatever you want to call us, exploring that grey area, right? So I want to leave it there really, because I don’t want to get into details of how you can do this and give you exercises and download this scorecard, etc. Etc. But I want you to rather reflect, challenge your own thinking, challenge other people, whether it’s your partner or someone at work who seems to be stuck in that rut of, oh my gosh, I have to take this job or I can’t possibly do that.

They haven’t even asked their boss if they can do part time work. They haven’t even looked for, you know, possible routes within that industry. They haven’t even tried. And that’s where I think we’re stopping ourselves before we’ve even started. And that’s doing ourselves a disservice. So let’s challenge those binary choices. Move away from the black and white thinking either or, and explore the spectrum of possibilities. If you, of course, have your own story of exploring your own grey area, I’d love to hear from you.

I share monthly interviews with people who are redefining success and creating their own world of grey. Or I need a better word for it, because I prefer the multicoloured rainbow world. And so if you’d love to share your story, I would love to hear from you. But above all, as I said, just try to shift your own thinking, challenge yourself, challenge other people you talk to and get creative with exploring those nuances between the otherwise very starkly different extremes. Maybe we can have it all, as it were, in this context, but we need to work out what that all is. We can’t have it all right away. At the same time, it will take time, perhaps, to build this new solution, and it will evolve over time. And that’s okay.

But let’s get comfortable with being uncomfortable. Let’s embrace that grey area. Let’s start to create our own little constellation calibration version of success that perhaps doesn’t fit any of those stereotypes and is unique to you. But that’s the whole point. It makes sense to you. It uses your strengths, interests and works for your family’s circumstances, your lifestyle, aspirations. And that will lead you to live a life that’s full of potential and happiness rather than trying to live up to someone else’s expectations or limited view of what is and isn’t possible. I leave you with that thought.

So let’s embrace the grey, the rainbows, exploring those nuances between the otherwise not helpful binary extremes that we tend to trap ourselves into. Looking forward to hearing from you. I’ll see you next week.

WORK WITH ANNA

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