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Overcoming Doubt and Embracing Change: A Guide for Career Transitions After 50

A real life story from 55/Redefined’s Simon Long, who offers nine valuable workplace lessons he’s learned, as he embarks on the second half of his life

Simon Long
Simon Long
Growth Director at 55/Redefined

Meet Simon Long, 55/Redefined's Growth Director

Simon has held a number of C-level positions throughout his career in the media, beverage and sports sectors. But as he entered his 50s, he realised he wanted (and needed) something different, facing some significant and confronting challenges along the way (learn more about his powerful and inspiring story by watching the video).

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Simon is now delighted to be championing age diversity as 55/Redefined’s Growth Director. Here's what he's learnt so far:

1. Know What You’re Good At

“Try to be open with others and have conversations about your strengths. Understanding your motivations is crucially important. Sometimes we don’t recognise what they are. Knowing what you are good at is a pretty decent place to be. Also, understand your weaknesses. From my experience, pretending to be something you aren’t isn't good for your wellbeing or your career.”

2. Know What Makes You Happy

“It sounds a cliché,” says Simon, “but I encourage everyone to sit down with people close to you and critique what matters to you. Happiness is an elusive quality, so aim for contented and fulfilled. I knew I wanted to pay things back, for having been so fortunate with so many great things in my life. At 55/Redefined, I am surrounded by people that I admire. I am more excited than ever.”

3. LinkedIn Is Your Friend

“According to 55/Redefined’s research,” says Simon, “just 16% of over-50s actively use LinkedIn.” That’s a huge, missed opportunity. LinkedIn is where recruiters search for candidates and it’s where you can talk with your work community. Simon recommends building your profile and engaging with other LinkedIn users. He has seen the success of this strategy for himself: “Lyndsey Simpson, CEO of 55/Redefined, saw a post I had written, reached out and we had a chat. And here I am working with her a year later!” Get seen with a great LinkedIn profile.

4. That Growing Sense of Purpose

“Getting to 50 and feeling a need for ‘purpose’, but not knowing what to do about it is a conundrum,” says Simon. Over a period of two years, Simon worked for several organisations, looking for something that answered his need. He found it at 55/Redefined, fighting ageism: “I am now working for a cause that resonates deeply with me and I have a sense that I can do something really valuable in the second half of my life.”

5. Network, Network, Network!

“The reality for us over-50s is that it’s extremely unlikely that we are going to find a job by signing up to a mass-market recruitment website. It’s just the way it is. But brushing down your contacts and reaching out can make a real difference. I always say, ‘Can I pick your brains? I would really value your opinion.’” There’s a useful article on the benefits of networking for the over-50s here.

6. Your Experience Matters

There is a whole world of experience and knowledge that comes with having spent decades in the workplace. It can add enormous value to any organisation. “So, stick at it and stick to your message,” says Simon. The world is slowly realising what the over-50s can bring to the workplace and the value they can add.

7. Don’t Take Things for Granted

“There are some extraordinary opportunities out there – for all of us. It is possible to pivot and change direction in the second halves of our lives. And remember, there are people a lot less fortunate than you are. So, for me, not taking things for granted and making the most of opportunities is a big, big lesson.”

8. There’s Nothing Wrong With Being a Follower

“It’s okay to admit you don’t want to be a CEO or the leader,” says Simon, in a message that will chime with many burnt-out managers and directors. “There is no harm in saying you no longer want that, even if you have experienced the heady heights of leadership. Supporters and followers are a hugely important part of any successful organisation.”

9. Ignore the Cynics!

“There are a lot of people who will not believe in your new career plan,” reveals Simon. “They won’t trust your motivation. That is about them, not you. Remember, there are people and organisations who understand where you are, who have walked in your shoes and would love to help – but you’ll only get that help if you ask for it. I found Brave Starts advice and support for older workers to be incredibly helpful.”

Just Start!

Looking for a new job at any age can be daunting, but when you're over 50, things can become more complex. Putting yourself out there and being proactive is the best way to find the kind of role you're looking for. Head over to Jobs/Redefined to browse our job listings, where age-inclusive employers are looking to hire people like you.

You can get a head start on your job search with a FREE CV review from our partner, TopCV.

Picture credit: Snowdonia, Simon Long