Am I Making The Right Career Change Decision?

Making The Right Career Change Decision – How Do You Know If You’ll Even Like Your New Career Or Business?
(Episode 9)

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What’s This Episode About?

How do you know if you are making the right career change decision?
How can you know if you’ll even like running your own business?
What if turns out to be even worse than the work you are doing now?!
Worries like that often indicate you are treating your career change process like an intellectual exercise (i.e. your efforts have likely never gotten further than your own head). 

Let’s change that! If you want to discover whether something is right for you  –  You need to get out of your head and start test-driving.
Experimentation is the only way to discover if something is right for you. 

In this episode, Rikke will show you how to identify and test-drive individual elements of a career or business – So you can get concrete, real life feedback which will enable you to  fall in love (or not) with your career change or business ideas. 

If you have a tendency to overthink everything – This is a must-listen episode! 

Full Transcript Of Episode 8:
Am I Making The Right Career Change Decision?

Intro: Welcome to The Career Change Podcast where you’ll discover the frank and practical advice and resources that are already proven to work in the real world when it comes to changing careers, or figuring out what business is right for you when you are a smart, but likely also stuck, overwhelmed or overthinking person in your mid 30s, your 40s to your mid50s.

I’m your host Rikke Hansen, a Career Change Advisor, entrepreneur, and former corporate HR professional with over 15 years experience of helping thousands of people just like you identify or create careers or businesses that are both meaningful and future proof. Welcome home!

Hey, it’s Rikke here and welcome to Episode 9 of The Career Change Podcast!

This will be an episode that’s specifically designed to answer a question I’ve been asked by a lot of my newsletter subscribers over the last couple of months. And it’s:


“How do you know if you’re making the right career change decision or business decision?”


“How Do you Know If You’ll Even Like That New Career Or Business You’re Considering?”


If you’re new to this podcast, or as a reminder, a lot of what I cover in the Career Change Podcast is actually based on the most frequently asked questions from my newsletter subscribers over at

So make sure you subscribe, so you can also let me know what you’d like me to cover on this podcast.


I often get asked variations of: 

“Rikke, how do I even know if I’m going to enjoy or like that new career?”


“How do I know if I’m actually going to enjoy running my own business? I’ve never done anything like that before!”


Also a variation of that and this is very much something I often hear from my private clients once they’re getting more serious about their transition. I often get an email or a call saying:


“But Rikke, what if it’s going to be even worse, this new thing, and I’m going to hate it even more than the job I’m trying to get away from now!?” 


If that sounds like you, I’ll give you some really concrete tips that I’ve already successfully used with my own career change and entrepreneurial clients for years. So if you’re already feeling now like I’m inside of your head, it’s because I’ve spent years helping clients change careers or start the right business. But also a lot of what I do in my work, whether that’s my 1:1 or my online programmes, is really help people deal effectively with all of those blockers that they put in their own way. You know exactly what I’m talking about, right? 


Have you noticed how often you just make things so much harder for yourself? 


You’re in good hands. Welcome to the Career Change Podcast. 


Here’s what I’ve noticed: 

A lot of the people who ask me the question “How do I know if I’m going to like that new thing?”, whether that’s a career or a business. 

They tend to be smart, intelligent, well-educated people. 

But what they tend to have in common is that they often spent years in professions or careers or jobs where they are paid to think and analyse and research their way through to answers. 

I.e. Any problem or challenge or project they encounter, they treat it as an intellectual exercise.


The problem though is when it comes to their own career transition process, and they then decide to apply that very same mindset and approach to their career transition, where they think that if they just think hard enough or research hard enough or overthink or over intellectualise hard enough, then they will get the answers. Does that sound familiar?

That is why they’re stuck and it’s likely also why you are stuck, which is why you’ve probably hit play on this episode, right? 


Because here’s the deal: 

When it comes to the really big questions in life, they’re not just a purely intellectual exercise. 


Now, I still wince when I say that, “they’re not just a purely intellectual exercise,” because I used to be the classic analytical intellectual overthinking type too!


But having worked with hundreds of 1:1 clients as their career change advisor and having advised thousands more online, I know that it turns out that us smart, overthinking people, we have the hardest time changing careers or starting our own business because we insist on overthinking and bulldozing over everything intellectually, right?


Smart, overthinking people have the hardest time changing careers or starting their own buisness.

Have you noticed? 


That’s why I know that’s so important to change. 


That overthinking type is literally the majority of my clients – The reason why I specialise in this group is we make things so much harder for ourselves because we overthink and over intellectualise, right?

I’ve been a career transition advisor and entrepreneur since 2005.  And most of my clients, they are literally the super smart people in professions where they are told to do these very over analytical things. So you my friend, if that’s you too, what I can tell you and what I’ve noticed is that:


Overthinking, overanalysing and over-researching, as much as they can be helpful, they also tend to be the very things that you are likely sabotaging your own career transition or own business efforts with. 


So just think about right now, whether that might be true for you too. Whether you might be doing that thing to yourself, as in you’re really trying to overthink and over-research and over-intellectualise this thing, and that is potentially why you won’t know whether you’re going to like it or not, because it is NOT just an intellectual exercise. Or decision. 


Does that make sense? Are you doing that? Can you see yourself doing this over intellectualising? Then you are absolutely in the right place!


By the way, I often get told that this podcast should come with a hypochondriac warning because people feel like I’m so much inside of their head.
But please know that’s because I really think there is a gap in the market for actually talking about how you might be feeling right now and for you to know that you are not alone.
It’s just is a classic scenario of smart people shooting themselves in the foot.

But most importantly of course we’ll also talk about what to do about it because here’s what I know for sure having helped so many people figure out what the right thing is for them:


When it comes to the big things in life, whether that’s falling in love, finding the right place to live or finding the right job or career or business for you, it is not just an intellectual exercise. 


You need to get out of your head and start test-driving things in the real world. 


Just like with love.
You can’t think your way through to whether you’re going to fall in love with someone, whether you’re going to like being with someone.
You need to take them on dates.
You need to allow yourself the opportunity to fall in love with them, to experience who they are, how they make you feel. 


You need to experiment. 


And it’s exactly the same thing when it comes to career transitions and starting the right business. You need to start test driving that in the real world.

It is a full contact sport, just like the good kind of dating, right? 


There is a wonderful quote from the entrepreneur who started Tough Mudder, which is an endurance sport company where they test both mental and physical endurance and it’s a guy called Will Dean.
And in his memoir he has this really great quote that says, 


“Entrepreneurs learn by doing. MBAs fail by overthinking.” (Will Dean) 


And this is relevant whether you want to start a business or not. It’s the mindset that matters!


Will actually went to Harvard Business School back in, I believe he graduated back in 2008, and he had the idea for Tough Mudder already as part of the MBA programme. But his professors were like, “Oh, your business plan is too optimistic. It’s too simplistic. You should be a management consultant instead.” Does this sound familiar? But he actually went on to start what used to be an incredibly successful business that made millions of dollars in sales where they took over these military training grounds and charged people a ton of money to do these fancy endurance races.

So, that’s just what he meant by that is that all these professors and academics, it was that mindset. As in instead you should just go ahead and do it, right? 


In his memoir he describes The Marshmallow Challenge or The Marshmallow Problem that was originally set by the head of design of Palm, Palm Pilot, Peter Skillman. And also it was a challenge that was popularised by Tom Wujec in his TED talk. It’s this exercise where you get teams of four people and they’re asked to build the tallest structure possible using 20 strands of dry spaghetti, a roll of tape, a ball of string and a marshmallow and they get 18 minutes to do that. 

So you might’ve heard of this, especially if you worked in the corporate world. I used to work in HR. This is one of those exercises we will give people.


But what’s really interesting is that making a structure out of spaghetti with a marshmallow on top is actually really, really hard to think your way through.
So what they’ve found, because they tried it with all kinds of different teams –

Guess what teams always did the worst?
They were recent MBA business school graduates because they were overthinking and overanalysing!


Who do you think did the best?
Kindergarteners! Because they got their hands dirty. They got right in there and didn’t think about hierarchy or overthinking.  

That’s why kindergarteners would consistently outperform MBAs. Isn’t that interesting?


So just think about it. 


Are you treating your career change or your business transition, like an MBA , where you’re overthinking and overanalysing and over-researching?

Or would you be willing to behave a little bit more like a kindergartener? As children, we naturally play, we iterate, we keep going. 

The kindergartners generally tried a lot more models of that spaghetti tower than the MBAs!

 But we (adults) are so afraid of allowing ourselves to experiment. 


So that’s why I love that quote and I recommend that you run it past you when you’re stuck.

Am I behaving like an MBA or am I behaving more like a kindergartener?

It’s turned into this classic lean methodology, agile startup methodology. So if you’re in that world, you might’ve heard about it. But I really love it. 


A lot of my clients over the years have been MBAs. And if you’re listening right now, you will know that we’ve had so many discussions.
I get these long emails about “what about this?” And “what about that? And I’m like, “Well, have you tried DOING this?” “Uh, No…” is their answer. 


I would literally translate this quote, “Entrepreneurs learn by doing. MBAs fail by overthinking.” And like I say, that’s whether you want to start your own business or not, it’s still relevant to career change. I would literally translate this quote into:


Whether you successfully discover whether a career or business is right for you depends on how willing you are to test it, to experiment and to get out of your head and interact with it and iterate. 


And if you don’t manage to change careers or start your own business, it’s very likely because it never got further than your own head. You are still overthinking it. 


Often when I challenge people they’re like, “Oh, but this is the problem. Or “That’s the problem.” And I’m like “Well, have you tried DOING something about it?” And they’re like, “Meh,” (but they’ve been THINKING a lot about it!). 


Somebody once asked me in an interview, “Rikke, what would the board be that you would put on Times Square?” And for me, for career changers, it would very much be:


How can you get out of your head today? 


Get out of your head, not to be confused with off your head! 🙂


That is so important. We want to get you quickly to the stage where you get out of your head and start getting real life feedback because that beats overthinking. 


How To Make The Right Career Change Decision?
Experiment + Test-Drive To Get Real Life Feedback

(Always Beats Overthinking!)


So let’s talk about how to test drive, because you’re like, “Yeah, that’s all very well. But how the heck do I test drive?” 


How To Test-Drive


So how do you test drive? How do you get feedback from the real world?
How can you figure out what it’s like to run a business if you’ve never done that before, or be a human rights lawyer or a nutritionist?

Clearly you cannot go from A to Z in one fell swoop, right? So I have another suggestion for how to approach it.


And no, there is no way you can know every single bit about whether you’re going to like it or all that kind of stuff.
Just like with relationships, but there’s a lot of stuff you CAN do.

We would all end up alone if we never dared going on dates and nobody would ever dare getting married. There will always be surprises down the line, but there’s a reason why we date. 


Let’s look at how you can date your idea. 


So here’s what I want you to do. 


Don’t think of any career or any business as fully fledged. 


This is normally where I see smart people shooting themselves in the foot.

They’re like, “Oh, but there’s this big (fully fledged thing) that I’m thinking about transitioning into.”

“How can I go from A to Z?”

“How can I know what the entirety of that experience is going to be like down the line?” 


You can’t! So stop insisting on binaries.


Start Test-Driving ELEMENTS 


Often I find people are stuck because it’s either all or nothing. 


Let’s just look at how we can figure out at least part of it. 


How can we experience something, a part of it? 


How can you test drive individual pieces?

And that’s really how I want you to think about this. 


Think about that thing you’re considering right now, whether it’s a job or business or a career. 


Look at how can you break it into individual ingredients, individual elements, individual parts. 


So if you think about any career or business, it’s made out of a number of ingredients or elements. 


Pull out some of those individual ingredients that are most important to you and then start test driving them, instead of insisting on test driving the entire freaking career or business, which is impossible!


An element could be something like a client group or a company culture or a subject. 


And remember, some elements are probably more important for you to get clarity on than others. 


It’s literally the equivalent of dating, right? You date before you become a couple. 

There are certain things that are important to you to find out and that’s why you date. 

You want to find out how this person make you feel, their values etc (and you’ve likely also got a No-Go List and/or a Tick List). 


It’s exactly the same thing that you can apply with figuring out whether something is right for you career-wise. 


And no, you will never find out everything. I have been married for over 20 years. I am still figuring out things about my husband, for better or for worse, but I’m still here. You get my point.


But really what it’s about is isolating the elements that matter the most.


So let me give you a couple of client examples, because this is obviously something I do a lot, especially with my private clients, but I also teach it inside of my online programmes. 


Client Example 1 – Test-Driving A New Company Culture / Colleagues (Element = Where?)


But one of my great examples of this is one of my clients from a couple of years ago, he was in his late 30s and he’d been an IT consultant for banks and prestigious retail and fashion clients ever since he moved to the UK from Africa in his youth.
And through working with me, we realised that actually IT, the subject itself. There was no point in throwing that away. 

This is something that often happens when I work with clients. People have this idea they hate everything. That they’re going to throw everything away. But through the process I’ve developed, we identify what is the career capital you still want to capitalise on?


And for him, we realised actually the issue was not IT. The issue was everything else.

He did not enjoy working in a corporate environment and he was tired of using IT to just make more money for rich people and rich companies.

What we figured out through this process, what he really wanted to do now was to use technology to solve real problems in the real world. Then with a view to going back to his own country in Africa later on and solve much bigger issues. 


But how do you start figuring out whether you’re going to like any of that if you’ve never done anything like it? 

Especially also, if you’ve only ever worked in a corporate environment with super smart, highly driven people like yourself.


Now, one of the things he was thinking about doing was starting working for a charity or government organisation, but he was obviously wary because how does he know if he’s going to like that before he jumps in? 


So the question we looked at and that you definitely want to ask yourself, how can you start test driving X? ( With X being that element you want to find out!)


How Can You Start Test-Driving Element X? 


So in this case, the element was the culture of these companies and the calibre of the people in there – How to explore if you are going to hate it, or if you’re going to like it. 


So here’s what he did:


He reached out on Twitter to a couple of people, one charity, one government organisation. 

And he offered some very quick pro bono work, using his current skillset, to solve some of the issues they had. 


He did a couple of mock up products, things like that, to see if he would actually like working with people from a charity background. 

To explore what it would be like to work with people from a government organisation. 


That’s the way he can test drive the element that is: 

What would it be like working with people in a very different company culture, working with very different people?


Right now is a very good time to reach out to companies and offer assistance. Reach out to people and offer assistance. Just think about right now, how much time do you spend on Netflix? How much time do you spend gorging social media? You probably have at least an hour or two a week where you can do that and offer that and try to experience what you are like in unfamiliar situation. Start dating, start test driving it. 


For a lot of corporate professionals, I would say a lot of my clients are corporate professionals, and they often have this idea that they want to experience a very different work environment. That’s definitely something you want to test drive before you start jumping. 


So look at how can you volunteer or how can you do some pro bono work to get a feel for that culture.

 How can you expand your circle of friends or become part of online groups?


Some people are like “Oh, but I can’t go out. I can’t do this. I can’t do that.” 
No worries – There’s so much stuff that you can do online!


And even if you’re like, “Oh, but I haven’t qualified in this new thing or I haven’t done this new thing before.” 
There’s no reason why you can’t test drive certain elements using your current profession to do it, right?
So don’t try to complicate it. Don’t try to find excuses. 


Look at how you can offer something in exchange for something. That’s something that’s super valuable. 


You should want to test drive things, test drive elements before you jump in, so it’s not just a guessing game.



Client Example 2 – Test-Driving A New Client Group (Element = Who?)


And another great example of that and of how you can test drive, it is another client I had. She came to me and she was like:


“Rikke, I think I want to start this massive wellness centre in central London for corporate professionals where we take them through all kinds of therapies and approaches and really sort them out.” 


But her entire career had been in finance and technology. She’d never run her own business. She had no background in wellness. She just had this massive idea that was going to take a lot of funding. 


And how do you start test driving or knowing whether you’re going to like something like that, just because you might have liked being the client of something like that somewhere else?


So again, we broke the elements apart, because I already knew having worked with her, that she was going to hate the operations aspects of running a centre. But hey, let’s make her experience that for herself. So we broke it apart. 


And one of the things I asked her were:


“Who’s your ideal client for this centre?”


Who’s your who?” 


And this is one thing if you’re starting your own business, a lot of what I do with my own clients is helping them nail down who the ideal client type is. 

Because if right now you are somewhere where you’re stuck because you do not like the people you work with, you want to make sure you don’t replicate that in the next business or career. Right? 


So I suggested to her:


 “What if you started doing a much smaller version of the centre and you started initially doing it as an online business?”


 “Let’s say a three months programme where you take people through a variety of things, just to assess whether you like that clientele.

And even if you don’t have all the expertise yourself, maybe you will hire a couple of people to run a couple of the programmes or you literally pay people by hour to give masterclasses in certain things.”


And guess what? She needed to stop being so bloody self-sufficient. A lot of people are bloody self-sufficient. They think they have to do everything and because they haven’t done certain things or haven’t yet done certain courses on some of this stuff. You can hire in to test drive with the help of other people. Don’t be so self-sufficient. 


And it was actually in the process of going through and offering that programme entirely online with a very specific group of people that she realised she did NOT want a big massive centre in the middle of London, or it could have also be New York or Sydney or wherever, with all of the operational issues.


She just loved the ease of having an online business, where she just needed to rock up and give some masterclasses and have some Skype calls, while she was taking care of her little boy, you know.


So she was like, “Oh, I’m so glad I test drove this,” because she realised who her ideal client group were – She loved working with the client group we identified for her!

She also realised, why would you want to risk something like a massive centre like that?

And guess what? Then COVID hit!


She would not have realised that if she hadn’t started test driving.

She’s a very smart woman. She could have gotten investment for that centre if she wanted to. She’s very well connected, incredible woman. 


But instead by just test driving one element, she realised she did not want to deal with all those operational aspects. She wanted an online business.


Over to you.


I am hoping you’re finding this helpful already, right? 


You probably now realise why we want to test drive elements. There are so many different ways – Over to you. 


Is there a piece or an element, just start at one, that you can pull out right now and you can start test driving?


What are the one or two elements that you most want clarity on?


 Can you start offering a mini programme to test your ideal clients? 


Is there something you can start writing, podcasting, interviewing people about? 


What can you start test driving, volunteering for? 


Can you learn a skill, do a programme? 


I mean, there are so many ways to test drive. Inside of one of my programmes I usually have a list of tonnes of ways to do it. 


But what’s really, really important is this:


That you get out of your head and you do something that allows you to create something or to experience something that’s tangible and that gives you real life feedback.


So the real litmus test for whether you are truly getting out of your head or not is really that. 


Are you creating something concrete that wasn’t there before? 


Are you experiencing something that’s tangible? 


And it’s likely also involving other people. 


And it’s something that’s either being published in the real world, which is also online, or you’re having real life interaction. 


That my friend is how you are going to allow yourself to fall in love with this new thing or not. 


That is how you’re going to have the full contact sport experience, and either fall in love with it or realise it wasn’t the right thing. 


Either way, you will be much closer to knowing if you like it or not. You will have even more ammunition. 


And most importantly, you would have taken something that you were stuck with because you treated it like an intellectual exercise and turned it into a real, full contact experimentation, a test driving project.


And you know what’s so amazing, and I see this every time that my clients do an experimentation project, they start test driving. One of the most beautiful things that actually come out of it is they realise and experience sides of themselves that their past or current career might allow them to experience or being exposed to. And then you get hungry. That’s what’s so incredible. 


Right now you might be worried because you haven’t test driven or experimented. 

But I’ll tell you, once you start doing it and you’ve also fallen in love with the parts of yourself that you experience through those test driving experiences, you get curious about who else you are and who else you could be and what rocks your boat and what lights your fire.

And once you tap into that, you will become unstoppable and you will be able to get a level of self knowledge that you might not have right now. And that’s absolutely a vital piece of the career transition puzzle.

Be curious about who you are and who you also could be.
Get out there. Get out of your head and start allowing yourself to fall in love. Okay?

It’s out there for you. It’s in there for you. You just need to start test driving it. All right? 

Get excited my friend, that’s the driver here. 



Leave A Review On Apple Podcast + Tell Your Friends About The Career Change Podcast. 

If you like this podcast episode, which I hope you found really practical, please do leave a review for the Career Change Podcast over on Apple Podcast and tell your friends about this.
I really want you and the people you care about to create work, to create businesses that allows you to be you and to really experience what you’re truly capable off. 

If you want more help, you can check out my programmes HERE. 

Thank you so much for listening. 

What you might want to do is get a little post-it note that says, “How can I get out of my head today?” 

And put it on your computer, or maybe even get a tattoo. 


So get used to get out of your head. That’s where all of the answers are.


 Thank you so much. I’ll see you over at







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