After being rejected from 500 jobs, I’ve finally found a great role at 60. This is how I did it – as well as the experts’ top tricks to land that dream job whatever your age

Losing her job was a blow for 60-year-old Caroline Madden two years ago but she felt confident in picking up another role within weeks.

A couple of years on, after applying for about 20 jobs a month on average, she had totted up 500 rejections.

Having never had problems getting employment before – even during economic downturns – Caroline suspected she had become a victim of ageism. But rather than feel sorry for herself, the divorced mother from Hull decided she had to face this perceived bias against employing older workers.

And following guidance from experts she landed herself a personal assistant job for a local entrepreneur starting this month.

We share her experience and offer top expert tips to help land that job whatever your age…

Beating the AI job bots

After a major restructure at the engineering firm where she worked as a PA, Caroline lost her previous job in September 2024.

She fears an increased reliance on AI filtering of application forms might have something to do with problems landing that next job.

Caroline says: ‘Although it is tricky to pin the blame on age there have been too many instances when an initial application was rejected despite showing the right qualifications, ability and experience. Age should be seen as a benefit with proven experience an asset. We don’t all just want to retire.’

She adds: ‘I eventually adapted my CV and applications by not putting down my date of birth and changed my qualifications from O-level to GCSE – because these older exams revealed I was at least in my mid-50s.

‘I am sure this CV change helped me get a job.’

GCSEs replaced O-levels and CSE qualifications in 1986, with students starting to take GCSE exams from 1988.

Under the Equality Act 2010 gender, disability, sexual orientation and ethnicity should not be discriminated against when applying for a job – and neither should age.

Caroline says: ‘One time when I got through the initial application stage, I was interviewed by AI. It was a realistic image of a woman asking questions – but the lips were not quite in sync with the words coming out. I still failed the test.’

Technology is also increasingly being used for interviews conducted over video links, which older people who are more used to one-to-one conversations might struggle with. Preparation is key and you need to master this skill. Download the software on to your laptop or smartphone and practise until you feel comfortable with the technology.

Caroline says: ‘These video calls seem particularly popular for public sector roles, where civil servants often work from home.’

Turn experience to your advantage

Caroline, who has two grown-up daughters aged 24 and 27, left school aged 16 to clean and wash dishes in a nightclub owned by her parents.

She later served behind the bar and by her early twenties was running a pub with a friend in York.

By her mid-twenties she wanted a more settled life – and found a job working as a PA for a local firm. In her late 30s, with a young family, she decided to retrain and took a course at the University of Hull to provide pastoral care and career advice at a nearby school.

She also found time to write a lifestyle column for the Hull Daily Mail. Caroline says: ‘The irony of being a career adviser is not lost on me. I know how to write a CV.’

Due to cancer Caroline decided to leave her school job in 2018. After that, having been successfully treated, she returned to PA roles.

Four years ago, she was a production team assistant at music events, hosting Liam Gallagher at Knebworth Park.

Caroline says: ‘It was particularly frustrating when “the computer said no” by seeming to put my age above the skills picked up from years of experience.

‘I started to focus on achievements rather than work dates and used the same buzz words as the job adverts, such as mentored, collaborated and resolved.’

Recruitment experts believe it is all about how you turn a lifetime of experience into terms that will attract potential employers – ideally with specific examples, as provided by Caroline helping to run a Knebworth concert.

Hannah Cornish, recruitment expert for job finding website CV-Library, says: ‘For older workers concerns about ageism can present a major hurdle. But they can turn this into a positive as experience matters – it is just a question of how you are going to sell this to land a job.’

She adds: ‘It is vital to stay confident and focused on what you offer – so practising your approach is important. Rather than listing years of experience on a CV, focus on achievements, with details of measurable results and transferrable skills.’

A CV should provide a single-page summary of skills and career achievements in a visually appealing way.

Ask for feedback from rejections to help fine tune a CV that should be tailored to individual job demands.

Get your foot in the door

Personal and business life coach Dr Sally Ann Law believes you should explore tricks to get your foot in the door that bypasses the AI application form barrier.

She says: ‘Get yourself in front of an actual person rather than just filling in application forms. Contact organisations and arrange to meet representatives in person. 

‘There are often trade events and local talks to attend where you can introduce yourself. Visit the library and enquire about events coming up. It all helps build a personal rapport.’

Cornish believes it is also worth trawling through contacts books and speaking to former work colleagues. Word-of-mouth vacancies can help set you apart from others with a personal recommendation.

Law understands dealing with rejection is challenging but is a key part of the process. She says: ‘Your task is to use all the tools available to get that job. Ask yourself – is there anything else I can do? Rejection is just part of the job – just ask a Hollywood actor. They can expect rejection for most roles.’

But actors can also offer inspiration. Law says interview role-playing gives you the edge and helps to prepare for unexpected scenarios.

Focus on the jobs market

Explore where there might be shortages in the workforce where you could find that demand outstrips supply for jobs.

The Government has an Annual Skills Report available through its website gov.uk – which also includes details on training for chosen professions.

Right now there are shortages of bricklayers in the building profession, NHS social care helpers and cyber security-skilled scientists.

Law says: ‘Avoid a scattergun approach and focus on the job you want and skills that prove your suitability. The problem with application rejections is you do not get a chance to represent yourself – show the human side that the AI formulas struggle to understand. Try not to allow this to knock your confidence.’

Law adds: ‘Try to impress with your transferable skills. For example, if going for a job as a PA you can beef up your abilities as a people person by linking them with practical experiences – such as how you have proved successful at handling extreme situations, ambiguous challenges and defused potential problems by using your quick-thinking skills.’

Cornish says: ‘Consider taking refresher courses. Details of these can be found from careers advisers at your local job centre. Employers are increasingly focusing on a skills-based approach to hiring.

‘Taking a course shows initiative and that you are keen to adapt to an evolving workplace.

‘Putting such small additions to a CV also show you are not out-of-date but comfortable with new technology, tools and modern ways of working.’

Keep active and alert

Caroline admits maintaining a positive mindset can be a challenge when job hunting.

She says: ‘There are a few strict rules I followed. Get up early and never watch television during the day. I go to my local gym up to three times a day paying a special membership rate.

‘Having a close network of friends living nearby has been vital. I visit them for a change of scenery and positive conversation.’