How to successfully make a mid-life career change (no matter the milestone)

How to successfully make a mid-life career change (no matter the milestone) 

Making a change at any point in your life can be a scary and unknown prospect. Making a change when you already have a successful career behind you can feel even more daunting. There are many opportunities for doubt and hesitation - the feeling that your peers have committed to their career path and you should be doing the same, or the concern that no longer being a 20-something, you've missed the boat to switch careers. Fear not! We're here to show you that there are options aplenty (whatever milestone you're nearing - whether that be 40, 50, 60, or beyond), and to help you discover what will work best for you.

It’s no secret that the pandemic has fundamentally shifted how we live, how we work, and our expectations of what work can look like. It presented many people with extended periods of reflection and exploration, whilst also exposing them to the fragility of daily life. You too may have joined countless individuals who reassessed their goals and what it meant to spend their time meaningfully. For many, questioning their purpose and coming to the realisation that they no longer want to settle for a career that didn’t excite or serve them. 

In a recent survey conducted by Escape The City, where we asked our job-seeker community how they were feeling about their jobs, over 53% said they wanted to change their careers entirely, with 79% wanting to work in a new field and 43% looking to retrain as a new profession. 

So the first thing to acknowledge is that you are most certainly not alone in your desire to make a change, with thousands of people in a similar situation to you, feeling similar uncertainties and battling similar internal questions. So let’s start by looking at what these are and how you can start to address them. 

1. Consider what is holding you back 

It’s important to think about why you are feeling this way. This will help you get to the root of what it is you do want to do and how to go about getting there. So start by taking a notepad and pen, and note down your thoughts about the below pointers. Remember the purpose of this is for you only (and you don’t even need to read it again if you don't want!) the idea is to get you thinking and get you to the route cause of what is holding you back.  

• Name the fear. Try and be as specific as possible, what is it that is stopping you? Is it financial responsibility? Are you worried about what others think? Or scared of failing? Write down your apprehensions and by doing so, try to acknowledge them. This will help you to accept and move towards solutions. 
• Now replace the fear with the truth. If it’s finances that worry you, take the time to do some research about the average salary of the career path you’d like to go down. Would you be able to cover your financial commitments? How much do you need each month to live comfortably and support any dependants? Go through this process for each of your fears and replace them with the truth. 

And finally, accept that discomfort is the journey. Making a mid-life career change and doing something different is hard. Know that action is the antidote to uncertainty. Remind yourself that you can do all of this without taking big risks. Accept that this is a process and that the fun is in the journey, not the destination.



2. Identify your transferable skills

Although it may not initially feel like it, by coming to a career change at age 40 or 50, you can be at an advantage, versus looking to do something different in your mid-late 20s. The reason for this is that you are already armed with the tools and skills needed for many different career paths. Yes, depending on what you want to change to, there may be a specific set of skills or qualifications that you need, but in terms of transferable skills, it’s merely a case of reminding yourself what you’ve got in your armoury. 

Work through the quick exercise below to help you identify your transferable skills:

• Take two pieces of paper.  On one piece, list out the skills you enjoy using and that you would be very happy to use daily.
• On the second piece, list the skills you don’t enjoy as much, but that are available to you in your ‘bag of tricks’. Be sure to think about skills from all parts of your life, those that you could legitimately charge a fee for. Here’s an example:

If you’re looking to apply your existing skills to a new role or career direction: take a look at each skill that you’ve listed and ask yourself ‘what does this say about me?’

In this way, your skills can reveal your traits. If you’re skilled at photography, this might tell you that you’re creative and have an eye for detail. If you’re skilled at organising events, this would suggest that you’re proactive and a great multi-tasker. How might these traits apply to your new field? Use your listed skills as examples of your innate strengths.

3. Accept that there is no one ‘right’ path 

In the same way, as there isn’t just one potential partner for each of us, there is no such thing as your one calling. You could certainly turn an activity into your calling by following your interests, doing it enough, eventually mastering it, and dedicating your life to it so that it becomes your “thing”.

However, the belief that you have a single path is extremely dangerous because it will stop you from taking even the first step in a new direction if you have even the slightest doubt that it might be the wrong direction.

Here’s a thought: thousands of companies and tens of thousands of roles didn’t even exist twenty or even ten years ago (i.e. Google, Airbnb, Etsy, etc). How inconvenient would it be if your One True Job hasn’t even been invented yet?

If callings are grown through taking actions (not discovered), and if you aren’t taking any new actions because you’re waiting till you “just know” – then you will never create a new life for yourself. This brings us to the next point. 

4. Experiment and explore new possibilities 

You don’t need to know what you are going to end up doing at the end of this process of transition in order to just start. If you don’t know what you want to do with your life and your career, the best way to figure it out is to start trying new things. Take the pressure off: don’t even think about quitting your job or making any kind of decision that feels risky, just start doing.

Test the water. Not everything has to make a huge splash. And that doesn’t need to mean quitting your job straight away. What’s more valuable is interacting with the world so that you have the chance to create new possibilities for yourself. Here are some ideas, all of which you can do without resigning or risking your financial security…

• Shadow someone – Ask a friend or a contact for a half-day following them around their place of work to see a new walk of life
• Ask for a sabbatical – What’s the worst that can happen? They can only say no. If they say yes you’re on a new path.
• Ask for a change of role – What’s the worst that can happen? They can only say no. If they say yes you’re on a new path.
• Attend a group – There are groups for all manner of interests. Join one, and meet people who could be on the same page as you.
• Create space – Take a day off work and explore your town or city, watch how other people are leading their lives and filling their days.
• Ask for help – reach out to someone who you admire and articulate the beginnings of your plans to them, see if they can help you.
• Do free work – So you want to test the waters? Offer to do them a fixed piece of work for free or volunteer to help out. 
• Try new things – They don’t have to be anything to do with your career or work, just go and do something new in your time off.
• Give a talk ­– Find a topic that you know enough about and care enough about to give a talk on it, and talk in front of ten people.
• Volunteer – Find a group whose work you admire and give them three hours of your time a week. See what you learn by committing.
• Reach out – Don’t be afraid to connect directly with those at organisations you admire – even if they aren’t publicising new job roles: reach out to them to see how you can help (see ‘do free work’ above!)

5 . Don’t be afraid to try again

If at first, you don’t succeed… Try, try, try again. It’s common to experience setbacks in life, but they do not define you. As cliché as it sounds, you’re on a journey. Thanks to books, films, and fairytales we’re made to believe there’s an endpoint to strive for in our careers/lives: the happy ending. However, in reality, there isn’t really an endpoint - most people have careers that move and change regularly. There’s nothing to say you can’t get up and try again when something doesn’t quite work out the way you hoped. 

There are many famous stories of people who faced setbacks in their careers. At the age of 65, Harland Sanders (more commonly known as Colonel Sanders) was retired and penniless. After coming up with his famous fried chicken recipe, he was rejected 1009 times before someone agreed to sell his chicken. At the age of 73, he sold KFC for $2 million. 

Arianna Huffington was rejected by 36 publishers at the start of her career. Then in 2005, she founded Huffington Post as a ‘last act’, now it’s one of the world's largest blogging platforms. She’s since written 13 books and has been named in Forbes list of most powerful women.

So the lesson here? No matter your age, career path, or area of expertise, if you’re feeling stuck in your career, we urge you to give it a shot and take those first few steps to do something different. Because there's nothing worse than regretting the things you didn't do. 

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