Have you heard the phrase “Freedom 55”? It was an advertising slogan for the London Life Insurance Company, popularizing the notion of retiring at the age of 55. In one Canadian commercial, a young man travels through time and jogs beside his older self on a tropical beach. As the two converse, he’s stunned to discover that he’s already fully retired at that age.

But if he looked off into the sunset, I think he’d see three boats on the horizon, full of people who are still working. And they consider it a type of freedom as well — freelancing over 55 and loving every minute of it!

A Tale of Three Boats

Let’s turn our eyes to that gorgeous sunset and sparkling ocean. There’s a world of possibilities out there. Now zoom in on those three boats, and let’s see who’s on them:

1. The Cruise Ship

You’ve retired from your full-time job and are ready to enjoy travel and recreation. In this case, choosing to freelance over 55 is a way of funding your retirement so you can pursue more activities in your spare time.

2. The Lifeboat

You’re starting a second career to keep yourself afloat and thriving. Maybe your previous employment unexpectedly ended, or maybe you’ve had to change careers for health reasons. In either case, freelancing offers a welcome option to continue working and supporting yourself and your family.

3. The Fishing Boat

Maybe you don’t need to work, but you’re driven to seek retirement with a purpose. Although your financial needs are met, you’re interested in pursuing meaningful work to impact the world around you and contribute to a particular industry or cause.

The Growth in Freelancing over 55

Far from being a whimsical view, statistics show that many are choosing to board one of those vessels in the freelancing world. For example, in an article titled “The Facts About Older Freelancers May Surprise You,” Jon Younger shares the following survey results:

“The Freelancers who were 50+ in our global survey comprised 31% (n=580) of our total survey population. And, we know from Upwork’s recent survey and Digital Information World that Freelancing is by no means only a young person’s game. According to their data, 30% of Gen X and 20% of Baby Boomers are freelancing part- or full-time.”

Furthermore, Nancy Shenker says “the number of older freelancers is on the upswing” in her article, “Freelancing After 50: How to Succeed at Any Age.” Specifically, she notes that as the number of freelancers in the U.S. has grown from 53 million in 2014 to 57 million, the number of freelancers between the ages of 55 and 64 reached 22.9 percent in 2017, compared to 18.8 percent in 2005. Remarkably, it continues to grow:

“More people are turning to freelance work as a second-act career, and close to 40 percent (37 percent) of freelance workers are over 55, according to the Economic Policy Institute (EPI), as reported by AARP.”

The Value of Transferable Skills

While many of you may be new to freelancing, many certainly aren’t new to working. When freelancing over 55, you bring a wealth of wisdom and experience from your previous career or multiple careers. Indeed, as the article above suggests, some older freelancers bring skills such as “varied expertise,” “research superpowers,” and “speed and calm under pressure.”

In addition, you may have transferable skills like the ones outlined in Freelance University’s “Entrepreneur’s Mindset” course:

• Technology skills
• Project management skills
• Social media skills
• Writing skills
• Financial management skills
• Media and graphic design skills
• Administrative skills
• Marketing skills
• Event planning skills
• Teaching skills
• Coaching skills

These skills can be directly applied to many of the services we’ve identified in our list of “22 Popular Freelance Niches in 2022.” Here are a few interesting examples:

Content

• Content Management and Marketing
• Content Writing / Copywriting
• Copy Editing
• Course Design and Management

Digital Marketing

• Email Marketing and Automation
• Social Media / Community Management
• Digital Advertising (Facebook / Google Ads)
• Digital Product Launches

Digital Media and Events

• Podcast Production
• Video Production and Marketing

Business Management and Support

• Virtual Project Management
• Customer and Client Support
• Virtual Bookkeeping and Financial Management
• Online Research

Design and Development

• Graphic Design
• Website Maintenance

Some services you may already be equipped to perform, and others may require upgraded technology skills and processes. But the choice is yours, and embracing a lifestyle of continuous learning makes freelancing over 55 an exciting adventure. There are many resources, tools, and educational opportunities available to sustain you as you pursue your niche now and in the future.

Embracing the Freedoms Offered by Freelancing over 55

As you think about those three boats on the horizon, you may be wondering who’s captaining them. Well, you are! Depending on your previous work experience, entrepreneurship may be a new concept to you, or it may be a familiar role. But the main point is that freelancing over 55 allows you to design a lifestyle that works for you.

If you used to dread Monday mornings and long commutes, you can say good-bye to that feeling. If you used to have to wait until the weekend to book a hair appointment, wait no longer. When you design your own freelance work schedule, you can go out during the day. And most importantly, you can prioritize the people and activities that matter most to you. Simply grab the wheel or paddles in your boat and steer it the way you want to by creating healthy boundaries with your clients.

Sometimes it’s hard to get used to that idea. But, believe me, once you embrace it, you’ll never look back. The time flexibility offered by freelancing lets you enjoy the things you’re looking forward to in retirement while still working and contributing to the industry of your choice.

Employee versus Entrepreneur

In a previous FreeU blog post, “Five Ways to Think Like a Boss,” we summed up the difference between employees and entrepreneurs this way:

“The good news is, as a freelancer or virtual assistant, YOU are the boss. And most importantly, you get to choose what kind of boss you want to be.”

That being said, adjusting to this new mindset can be challenging if you’ve worked as an employee for many years. For instance, some people may retire from their original position and then do a similar type of work as a freelancer. In these cases, it’s important to know the difference between the employee and entrepreneurial mindset. That way, you’re embracing all the freedoms you’re entitled to and developing healthy relationships with your clients.

The course mentioned above provides key perspectives. Here are a few to keep in mind:

• An employee follows a job description while an entrepreneur delivers a service.
• An employee’s schedule is directed by others, while an entrepreneur directs their own schedule.
• A company invests in its employees, while entrepreneurs invest in themselves.
• An employee markets during the job interview, while an entrepreneur must always market to achieve long-term success.

For some of you, this might be a shift in thinking. For others, maybe it’s something you’ve been longing for. All the experiences you’ve had until now contribute to the way you approach freelancing over 55. And along with that, you’ll have an opportunity to cultivate characteristics like thinking outside the box, setting your own goals, directing your own business activities, and leading others.

Final Thoughts and Encouragement

I’ll tell you a secret — I’m on the same shore, ready to board one of those three boats too. In a few short years, I’ll be 55. Years ago, when I first saw the Freedom 55 commercial, I envisioned myself being fully retired too. But now, I fully intend to continue freelancing well over the age of 55. Not just for financial reasons but because I feel I still have skills and knowledge to share. I’m not ready to stop contributing to the industry I’ve gained experience in.

So, which boat do you see yourself boarding? I’m leaning toward the lifeboat right now, but someday I’d like to board the cruise ship. And I’d also like to spend time in the fishing boat. In reality, we can try all three, as long as we keep moving forward and boarding each one at the right time for our businesses and lives.

As you explore your options, an article titled “The Rise Of Greypreneurs: Freelancing After 50 (infographic)” provides this wise advice:

“Keep yourself and your knowledge base fresh, take advantage of online courses and other resources to solidify your professional know-how. For older professionals who plan on working past retirement age, looking forward and growing up from a current position if possible can keep a career strong. Showcase your age as a positive attribute, as with it comes experience and wisdom while at the same time emphasize that you are willing and capable of learning new things to supplement tried and true skills.”

Then, like the man in the Freedom 55 commercial, you can look forward to a future where you’re happy and fulfilled. Except in this case, you’re enjoying both life and work.

And now we’d love to hear your thoughts! Which part of freelancing over 55 appeals most to you? Do you see yourself boarding one of those boats in the future? Please share your thoughts in the comments below.