How To Move Into A New Career Without Starting From The Bottom

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Image: Yusuf Evli

You've put so much time and effort into your career so far. You're respected, you know what you do inside and out – you'd hate to have to start from scratch again. Natasha shares how becoming an 'insider' can help you bypass the bottom of the ladder and be taken seriously in a new industry.

One of the scariest things about considering a move into a totally new field is the thought of being a beginner again.

The newbie. The 'less-than'.

And it doesn't just affect you once you've landed an opportunity in your new career. The challenges and uncomfortable feelings begin right at the start.

You know what you want to do next (or at least, you're pretty sure you do), and the feeling of being 'an outsider' to the industry makes you tentative and nervous about applying for jobs. It infiltrates the way you network with people in the field; you find yourself feeling not-good-enough, useless, unimpressive and lonely.

The challenge, then, is to find a way to rid yourself of that 'outsider' feeling. To become an 'insider' while you're still on the 'outside'. To equip yourself with the knowledge, confidence, and behaviours of an insider, before you've even got a sniff of a pay cheque.

Sounds like a nice idea, right? But is it really possible? What if you're pressed for time, working a full-time job? Won't it take years?

In short, yes, it's possible. And no, it doesn't have to take years.

And the beauty of this approach is that it's twofold. It doesn't just leave you feeling more confident and capable; it also changes the way you're able to connect with the people who can help you make a shift. It alters the way people see you, the opportunities you can bring to fruition, and the speed, effectiveness, and fun-factor of your entire career change.

To start becoming an 'insider' in your chosen field, even from the outside, there are two games to play: The 'do' game and the 'connect' game.

'Do' like an insider

"The trouble with the rat race is that even if you win, you're still a rat" – Lily Tomlin

"You are what you do" – a hugely controversial statement. Of course, what you do for a living doesn't define you as a person (at least, it doesn't if what you do isn't aligned with who you are. The people who argue most strongly against the above statement are usually the ones who are doing work that doesn't mean anything to them).

But you can start 'being' what you want to be without getting paid for it.

I'd invite you to consider the idea that getting paid for something isn't what makes you a credible member of that group of people.

Is a writer only a writer if they get paid to write, even if they write the most incredible fiction and poetry at a rate of knots?

Is a natural salesperson only a salesperson if they get paid to sell? Or would you describe them as a salesperson based on the fact that every time they see you, you're left dying to try out the restaurant they told you about, or to get the same kitchen blender as they've just bought?

This process is about detaching the idea of work (and the status that doing that work gives you) from the idea of money. It's about becoming an industry insider without the payslips.

If you're worried about having to start from the bottom in your new industry, it's probably because you feel under-qualified, under-experienced, and as though you're an outsider to the field.

So what do you need to do to change that?

I'd argue you need to start behaving as though you're already what you want to be.

For the next month, even if you're working a full-time day job, I invite you to play a game of 'Let's Pretend'.

In your time off from work, pretend your day job doesn't exist. Instead, pretend your day job is your dream job.

  • How would you spend your leisure time?

  • What events would you go to?

  • Where would you hang out?

  • Who would you choose to be your friends?

  • What professional development classes, courses, or workshops would you attend, to further your expertise in your field?

As mantras go, it's a bit of a mouthful, but I invite you to keep this sentence in mind: "Do what you would do if you were what you want to be."

Serena (name changed) attended one of our career change workshops last year, and got in touch with me recently to share an update on her shift. She was an Executive Team Leader for a major insurance company. But, in her spare time, she chose to start acting as though she were already the Events Organiser she dreamed of being.

She went to industry events; joined professional discussion groups online; organised a few small events for friends and family; took short courses and signed up for one-day workshops at weekends… essentially, she started living a double life.

She started to make friends within the industry – and was blown away by how alive she felt when she was around them.

"It was great – it was like we all understood each other on a different level than my day-job colleagues and me. We ended up with shared jokes about how neurotically organised we are… nobody in my 'previous life' understood how happy Tupperware boxes made me, but these guys totally got it! It sounds so trivial, but being around people who saw the world the way I did was an amazing revelation."

And she was building up experience, knowledge and connections that now meant she was no longer an 'outsider' to the industry. She didn't need anyone to give her 'a chance'. She was already in.

'Connect' like an insider

At Careershifters, we encourage career changers to focus their time on looking for ways to make meaningful connections with people who work in their dream industries, rather than spending hours scouring job sites.

Why? Because of three things we've discovered from working with thousands of career changers:

  1. What you're looking for when you're looking for a job is an opportunity.

  2. Opportunities only exist where there are people.

  3. As a career changer who's likely lacking in CV-worthy experience, it's much easier to interest, inspire, and motivate people to get to know you (and offer you an opportunity) in person than it is using the standard CV-and-cover-letter-sent-via-email-to-a-nameless-faceless-address approach.

To most of the people we work with, this makes a lot of sense. But often, when people start doing this, we watch them take on a deferential, almost apologetic way of being.

"I feel like I'm bothering them"

"Why would they want to talk to me?"

"It’s not like they're just going to hand me a job."

Here's another thing we've discovered:

People will always relate to you in the same way as you show up.

What this means is that if you show up with thoughts like the above in the back of your mind, it's pretty likely they'll wonder at some point why you're acting so guilty and shifty around them. You'll be apologetic, deferential. You won't offer them value (becuase you don't think you have any value to offer). They'll lose interest pretty quick.

But if you show up as an insider, they'll relate to you as an insider – and insiders don't have to start from the bottom.

So what is there to do?

  1. Start getting to know people who work in that industry
  2. Show up for them as an insider

You're likely to create a much more meaningful, two-way connection, and be taken more seriously, if you approach them as an insider.

And (here's the really cool part): now that you've started 'being what you want to be', you are an insider.

Now let's just slam the brakes on for a second, because this next part is important:

This does not in any way mean you should lie about your experience, your day job, or your ultimate desires.

Remember, we're not talking about creating a false identity here. We're not talking about tricking people into thinking you're more experienced than you are. We're talking about becoming an insider through action in your spare time rather than a pay cheque, relating to yourself as an insider, and showing up as someone who's both interested and interesting.

We're talking about approaching people like an insider would – with the confidence and authentic, human-to-human approach of pretty much anyone other than someone who belongs at the bottom of the ladder.

So what does an insider connection actually look like, in practice?

1. It looks like seeking connection and information, not seeking a job.

If you approach someone with the intention of getting them to offer you a job, you're automatically swaying the balance of equality between you. And that power balance (even though it's entirely fictional) will affect the way you behave, and the way they relate to you.

Put the entire idea of getting a job on the back burner for a while. Instead, get interested in everything else about the industry. Get interested in building a relationship with the people who are connected with that industry – a relationship that will last, rather than a transactional interaction that leaves everyone feeling a bit cold. 

Imagine that landing your dream job is inevitable – a genie has granted you a wish and your ideal role in that field is 100% coming to you. What questions would you ask your new connection then?

2. It looks like giving (and then getting in return)

The other thing an insider does is offer value to others.

Maybe you've just had a conversation with someone who could help you move forward in your career change. Since you're already 'being what you want to be', chances are you'll come across an article related to their industry, or an event that might interest them. Send it their way.

Maybe they mentioned feeling really stretched with the amount of work that's coming their way. Offer to give them a hand with some of it, free of charge.

Become an asset to the people around you, even if only in the very smallest of ways.

Offer value, however small and however low-effort, wherever you can.

People who are only getting to know people to get a foot in the door don't offer value. They demand it. Insiders play a different game.

Doesn't this make me a fake?

No, it doesn't.

Sure, there's a game of 'Let's Pretend' involved. But all this is there to do is to get you out of your head and into action. Out of familiar, boring, comfortable, dissatisfying environments and into new ones, full of potential. Out of fear and limiting beliefs and into exciting, mutually beneficial relationships with the people who do what you want to do.

And you may well discover along the way that you're already more of an insider than you realised. 

So, in short, no. It doesn't make you a fraud. It makes you proactive. And, in fact, it actually works better if you're as straight and as honest with the people you're around as possible.

Because, at some point, one of your new connections is bound to ask: "So why on earth aren't you working in this field? You're clearly passionate about it, and you obviously know your stuff…"

And within that question lie endless possibilities…

This week, I'm challenging you to find one way to 'be' or 'connect' like an insider. Forget about the fact that you're not getting paid to do your dream job (yet).

Instead, take one action that's consistent with the way an insider in your chosen field would 'be' or 'connect'.

Watch how it changes your perspective on what's possible, how people relate to you, and what you learn about how to make your shift faster, smoother, and from a space that's way, way beyond the bottom of the ladder.

What 'insider action' are you going to take this week? Let us know in the comments below!

Natasha Stanley's picture

Natasha Stanley is head coach, writer, and experience designer for Careershifters. When she's not working, you'll find her listening to neuroscience podcasts, learning pottery, and dreaming up her next adventure.