Guess what, freelancing is not simply a young person’s game or something you can only do in your 20s (yes, seriously!). More now than ever, we’re seeing the rise of the older, more mature and experienced freelancer, and as we’ve seen within our own community — they’re absolutely crushing it.

Creatives over 35, over 40 and even in their 50s (the “silver self-employed”) are embracing this lifestyle with enthusiasm and proving that age doesn’t matter. In traditional business, we often hear about issue of ageism and that age (and the experience it brings) can be at times not recognised or supported. Well, the opposite seems to be true in the freelancing world!

Older freelancers can be a benefit to your business. The beauty of remote work is that digital communication makes ageism difficult and that ultimately, it’s simply about delivering quality work — regardless of age, location or background. 

So why are so many taking their leap later in their career? At CloudPeeps, we have a diverse global community across various skillsets and ages, and everyone has a story to share. We asked some Peeps in this (slightly) older age bracket to share why they made this decision to freelancing, rather than stay in a somewhat more stable “normal” job. Here’s what they had to say:

1) Independence

Freelancing provides the opportunity to break free from the traditional office workspace and break out on your own, with the aim of greater freedom and independence. It’s an exciting step to take later in life, when you have a career behind you and extensive experience of all the pressures or restrictions felt within the workplace. It’s a chance to rediscover yourself, as Peep Anca says she’s now experiencing, “doing some exciting work I never knew I was capable of doing, constantly reinventing myself.”

Several Peeps commented on how they were made to feel stuck within the corporate world, where they were supposed to “feel “lucky” to have a job”, and “not grimace at all the extra work you were doing for no extra money”, like Peep Dorie shared:

“Now I’m able to take on the work I want to – in a few different fields instead of one, and balance it with enjoying life more, taking big trips and such without worrying if I have the vacation time built up or if it’s going to put too much stress on others.”

2) Fulfillment

The toll of the corporate world and the need to adapt to open plan offices if you’re an introvert, or play “the game” to get ahead, or adapt to the office politics to survive, are often reasons for taking the leap. For many freelancers, it stems from seeking greater fulfilment in both their professional, and personal, life. A deeper work/life balance. A desire to take control of your career and go after more meaningful work, on your own level. Peep Erin explains why:

“I was sick of the politics and the roadblocks along with the stagnant attitude. People figured everything should stay the same. It was boring. I love setting my own agenda and searching for work. I love the fact that it’s in my hands. If I do a good job, I get more work. It pushes me to be my best rather than a “safer” career where you just punch the clock daily.”

Peep Paige agrees:  “As I get older, I’m much less inclined to put up with the stress that full-time employees often have to endure, just to take home their twice-monthly paycheck.” Paige’s desire to focus on the work, rather than the office politics, is not unique. 

3) Flexibility

As our need to balance our work with our lives increases, the option of becoming a solopreneur or digital nomad has become extremely attractive. With your career already developed, it can be much easier to take those skills and apply them to your own business or use this background to review your values for a fresh new direction (or chapter) in your life.

Peep Naomi shares: “I decided that volunteer work was more important to me than my career, but obviously didn’t pay the bills so decided to start freelancing. This allows me to travel to different locations to volunteer and work at the same time. I love the flexibility that freelancing allows!”

Freelancing can also be an option for those seeking to raise their kids with a more flexible schedule, or deal with personal issues on your own schedule. For Peep Christina, it was when her daughter was born, as “we needed a way for me to stay home but still make money.”

Peep Monica said a death in her family was the catalyst for her freelancing start:

“I knew there was no way I could work in a 9-5 office environment with zero consideration for my grief. So I launched my business full-time and here I am three years later, living abroad, and leading a lifestyle that is free of the demands and stress that people deal with back home in the states. I have plans to move to Colombia next year or sooner!”

4) Circumstances

Unfortunately, not all freelancers start by choice, it can be triggered by circumstances beyond their control, such as being laid off. Several Peeps highlighted that they were forced to take control of their futures, after being made redundant or realising their industry was dying.

“My motivation was due to layoffs. I rode the rollercoaster of tech company mergers and acquisitions too many times and decided to strike out on my own”, shared Peep Mark. For Peep Elizabeth, change came when she realised she was working in a dying industry and needed to ”make a change and build a life I enjoyed.” But there were direct benefits to not rushing into this decision, she says:

“The benefit of waiting [to take the leap] is knowing yourself better and having a strong network of people you’ve built in your corporate career to tap into for freelance jobs.”

Peep Donna sums it up perfectly why we’re seeing such a rise in the older freelancer: “I enjoy helping other biz build their dreams while I save time and money. Add on – why does age matter? We still contribute and help at all ages.” Exactly!

No matter what age you’re at, these are all great (and common) reasons to take the leap. Going freelance later in life may feel more risky and less secure, but remember you’re also older and wiser, as our Peeps attest. You bring a wealth of knowledge from your career so far, plus a keener eye to seeing through the challenges of running a business you will possibly encounter. Combine this with your passion to do high quality work and desire for greater freedom in your life, we’re sure you will have no regrets for forging ahead on your own path. If in doubt, just chat with our community 🙂

So if you’re considering taking the leap but thought you were “too old”, we hope this gives you the motivation (and inspiration) you need. Just go for it!

Want to take the leap? Sign up to CloudPeeps and join our community! Update your subscription plan to Pro — you’ll have unlimited proposals per month, additional curated job leads, a promoted Peep profile, phone/email assistance from the CloudPeeps team, and more.

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Kat Loughrey
Kat is a digital consultant who specialises in digital strategy, social media and community management. Based in Berlin, she can be found talking social media at meetups, running her upcoming workshops and organizing the next Freelance Friday.
Kat Loughrey

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