Flexible, Portable, Lucrative: Why Boomers Freelance

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Posted by The Savvy Retiree on October 30, 2019 in Online Income Opportunities

I have a story that will sound very familiar to many baby boomers…but it ends a little differently than you might expect.

For many years, I held a career job I really liked. But, as happens when one gets too comfortable, I got promoted. This brought with it more responsibilities and expectations of greater performance. Suddenly, the aspects of the job I really enjoyed started to dwindle away.

As I approached my 50s, my hair started to thin, and my job satisfaction waned. I didn’t get the assignments I wanted. I didn’t get the travel I wanted. I didn’t get the responsibility I wanted… but I did get volunteered to attend more meetings.

For many baby boomers, that’s where the story ends—until they find the sweet relief of retirement. But in 2001, I made the decision to leave my corporate job behind.

My strategy was relatively simple—do the same kind of work I’d been doing for decades as an employee but do it as an independent freelancer. With freelancing I could choose the level of work I wanted to do at any given time. I could create my own schedule and work the times of day when I was most productive. And perhaps best of all, I could do it from any part of the world I wanted to be in.

Back in those early days of the internet, the road to online freelancing wasn’t clearly marked, and the kind of work I wanted to do wasn’t very much in demand online. It took me time to find strategies for nabbing clients that guaranteed a steady income.

But a lot has changed since. Fast forward nearly 17 years, and the online freelancing landscape looks a lot different. The wild west space I entered in 2001 has given way to an intuitive user-friendly experience designed to attract even the most staunch Luddites to the world of online freelancing. In fact, over the past few years I’ve noticed three distinct trends that are converging to create the perfect storm of opportunity for anyone entering the freelancer market today.

After successfully transitioning to freelance 17 years ago, Winton has helped hundreds of boomers do the same.

Firstly, there has been an enormous shift in the U.S. economy. Today, 34% of jobs in the U.S. are freelance. And according to some experts, this number will rise to 50% by the year 2020. As a baby boomer you’re positioned perfectly for this shift. With years of experience behind you, you have highly developed problem-solving capabilities, extensive experience communicating verbally and through writing, and a wide-ranging skill-set derived from years of shifting between different roles.

Secondly, the number of online networks that give you access to the freelancing market has exploded. You simply post a digital profile on an international network of buyers of freelancing services, and you have immediate access to hundreds of thousands of jobs every month.

Thirdly, the ability to communicate remotely has never been easier. You can sit virtually any place on the planet and exchange emails, send documents, and even have live video conversations with your paying clients.

Taking the First Step Into Freelancing

When Sharyn Nilsen retired in her 40s from her government job as a planning and quality manager, it was with a mind to spend more time traveling with her husband, Tim.

“I didn’t start out thinking this was the path I’d take,” says Sharyn. “Originally, we planned to teach English one year on and travel for the alternate years for as long as we could. And, it was a pretty successful strategy that we implemented for three 12-month stints in Ho Chi Minh City, Vietnam. While we enjoyed living there, the fact that we were tied to one spot didn’t fit in with our desire to rove full-time.”

In 2016, Sharyn stumbled onto the concept of freelance writing and the freelance platform Upwork. “There were thousands of jobs, but most seemed low paying. So I started reading blogs about how to position myself in a niche and earn some decent money,” she says.

“When I opened an account I set my rate at $22 an hour, around the same I was earning teaching English. I started applying for jobs I thought I could handle and soon found a fixed price assignment to create vocabulary sets for teaching English. I was pretty chuffed at earning my first $80, but it took me longer than I would have liked.”

Soon Sharyn had earned two 5-star reviews, so she raised her rates to $30 an hour. She understood that her experience as an English teacher made her a sought-after freelancer within that niche.

“Interestingly that’s when things started to take off,” she says. “It seemed the more I raised my prices, the better the clients I got. They seemed to value my opinion more and respect me as a professional. I even started writing outside my niche. I created copy for various websites, including carpet cleaners, shed suppliers, outsourcing companies, and a car rental agency. The car rental client is still with me. The topics are easy to research and write, and I’m making around $40 per hour. I’ve earned over $3,200 from him alone. I’m at the stage where I’m subcontracting out some of the work because I have other higher paid projects to complete.”

Dan Carpenter moved to Spain with his family just over two months ago, renting an apartment just outside Barcelona. Like Sharyn, Dan’s first venture into remote working was through English teaching. However, after giving freelancing a try he quickly found success.

Prior to Dan’s move overseas, he was living in suburban Salt Lake City. “I worked in SEO and internet marketing. I helped to increase companies’ traffic and sales through better exposure in Google results. While I had good jobs that taught me a lot and paid decently, I never loved the company structure. I hated having a boss, and I hated being a boss. For me, the best type of work is just me and a project.”

Dan decided to move to Panama with his wife and kids and shortly after started teaching English online. Then one day a friend asked him if he could revamp his professional bio so he could use it on his social media. He did such a good job that his friend referred him to another acquaintance, and this time he got paid $50 for an hour’s work.

“Something changed in my head when I realized I could charge people $50 an hour, and they would actually be happy about it,” says Dan. “At this point, I had just returned from a year of living with my family in Panama, and I was getting ready to leave for another chapter in Spain. I can remember thinking about the added pay leverage that I could have as a skilled freelancer, and I decided that I would actively start seeking out freelance jobs.”

Dan figured that at the pay scale he could demand, he would only have to work 15 or 20 hours a week to live comfortably in many places around the world. And, if he wanted to, he could increase his number of clients and work full-time.

Freelancing gave Sharyn Nilsen and her husband, Tim, the opportunity to take an extended bike trip across North America.

“The next pivotal moment for me was finding the freelancer platform Upwork. I could browse actual job requests of clients who were actively looking to pay somebody for help,” he says.

“Since that time, I have created websites, done SEO work, and done a fair amount of writing as a freelancer. Nowadays, the bulk of the work that I do is higher leverage content strategy, for clients who are trying to get traffic from Google. I earn great money on flexible terms. And best of all, I can do it from anywhere in the world.”

For Daria Hilton, freelancing was a way to kick start a new life with her partner, Chuy. They had been living in the San Francisco Bay area, working crazy hours and yearning for a change of pace and place. Physically demanding warehouse work had taken its toll.

The couple decided to move to Chapala in 2016, a town close to the area where Chuy grew up. “When I was living in California,” says Daria, “I would work on and off as a writer, but never full-time. I was able to nab some grant writing jobs for non-profits. I also dabbled in technical writing while still in college, where I got my B.A. degree in English.”

While in her early 50s, and just before leaving for Chapala, she discovered Textbroker, a freelance platform specifically for pairing writers with clients. “I set up my Textbroker account, took my entrance exam, passed, and got my rating. Most applicants get four stars, which is what I got. This means I can pick any assignment of four stars or less. The higher the star rating, the higher the pay,” says Daria.

“I saw how working for Textbroker would allow me to get out of working long hours in a warehouse and into writing. Having moved to Mexico, I needed a job. I’m a good writer, and with Textbroker I can get steady work and I can work from anywhere.”

She started off working around 20 to 30 hours per week, Monday through Friday. “But I quickly figured out which stories I could bang out and, at the same time, bring in a wage that would allow me to live comfortably in Mexico.”

Daria Hilton uses the freelance network Textbroker to find paying writing assignments to fund her life in Mexico.

Daria’s dream is to get paid writing about her passions, such as historical ecology and her family history. “Having the option to work for Textbroker allows me to make an income, practice writing to deadlines, and learn how to get my commas in the right place. All of this is ultimately helping me to reach my goal and, as a writer, all those things count.”

Building a Winning Freelance Profile

Whatever type of online freelancing you wish to pursue—whether it’s data entry, writing, website design, legal work, social media management, programming, sales prospecting, or consulting—the pay rate you demand will directly correlate to how engaging your professional profile is on the freelance network you use.

Your profile is very different from a standard resume in three distinct ways. Firstly, it is skills focused. Most resumes are chronologically oriented, but a good profile should emphasize the skills you have relevant to the type of freelancing you want to do. Secondly, you should focus on brevity over narrative. Online freelance buyers have a very different reading style than the human resources manager of yesteryear. They scan your profile looking for key words that tell them about who you are and what you can do. Bullet points and short sentences win over the narrative style. And finally, it’s important to keep your profile conversational rather than formal. A big part of freelancing is creating a relationship between buyer and freelancer. Because there’s no face-to-face interview, the buyer needs to know if you’ll be easy to work with. The best way to show this is to make your profile conversational and maintain an approachable attitude.

Your next consideration will be the photograph you use. I’ve interviewed hundreds of freelance buyers, and over 50% of them say that if they don’t connect with the person in the photograph they won’t go as far as reading their profile.

It’s important to have a simple, in focus, and well-lit headshot, free of distraction. You want to be seen as friendly, somebody that a freelance buyer would want to do business with. You should have a slight smile, and not a cheesy grin. Think of this as how you would show up dressed to a job interview. This is how you’re representing yourself to your potential client.

If you want to go one step further, you can take Dan’s approach and add a brief video to any proposal you submit.

“This goes a long way to convey authenticity and build trust. Almost nobody does this because it requires extra effort, and for that reason, having a video in your proposal causes you to stand out big time,” he says.

When writing the body of your profile, keep in mind that freelance buyers want to hire people who are more than one-dimensional. Even if you want to focus on just one kind of freelancing task, you’ll still need to show that you have skills in other areas. The assignments you choose will still be up to you, but you want to be evaluated as the well-rounded candidate you are.

Remember, if a buyer says they need a writer, what they’re really asking for is a writer who understands their world. For example, if the buyer owns a website that specializes in organic gardening, do you think they’re going to choose the writer who can “write about any topic,” or the one who has been an organic gardener for 12 years and knows their niche inside out? Advertising your unique skills is the quickest way to finding an assignment designed for you.

In the same vein, when you’re creating your profile you should avoid your natural inclination to use the pronoun “I” where possible. From the freelance buyer’s point of view, overusing “I’ sounds like boasting. They don’t want to hear you brag about how good you are; they want to know what you can do for them.

Most importantly, your profile should include keywords and phrases relevant to your area of freelancing. The right words and phase act like laser beams that guide you to your best assignments, especially those with long-term potential.

This is how you take 100,000 jobs on a network and boil them down to half a dozen to two dozen that are just right for you. You should come up with 10 to 20 keywords or phrases that reliably produce jobs that fit you well. These keywords will help buyers find you and help you search each network’s database more effectively.

Once Sharyn had taken a few courses to help her learn some these strategies she was able to earn higher rates as a freelancer. “I learned how to jazz up my Upwork profile and put in better proposals. Underpinning my approach is to let the prospective client know what I can offer them rather than talk about myself and my skills,” she says.

“Once I got good at it, I decided to increase my rate to $42 and shortly after that to $62. The beauty was, by this time I didn’t have to pitch. Most of my new jobs were from personal invitations, attracted by my profile and excellent client feedback. I received several invitations for projects at this price level, and quite a few were for quality management and business improvement topics which tapped into my experience. One of these has just turned into a lucrative retainer of around $1,700 for approximately 25 hours a month.”

“The thing I love about these long-term clients is that the job takes less effort as you learn more about their business, and once they trust you they’re more than happy when you suggest an expanded role. They’re also more understanding when I tell them I’ll be in transit for a week or more, and I can plan to keep things rolling while I’m off on another adventure.”

Sharyn says that being an expert wasn’t necessary to finding success as a freelance writer. “You don’t even have to have fantastic spelling and grammar; there are tools you can use to help you correct that. I run every one of my articles through Grammarly and ProWritingAid before I submit. Eventually, all that correction rubs off, and you make fewer and fewer errors.

“Eventually, I’m aiming to charge between $150 and $200. At that point, I’ll wind back the hours to around 10 a week and focus on the most enjoyable projects, like my travel writing and a couple of books I have in the pipeline.”

Dan, on the other hand, is continuing to ramp up his freelance output. More recently he’s begun creating “bundles” or package deals he can offer to his clients. “It’s a way to transform your skills into more concrete, higher-priced offerings. Instead of listing yourself as an editor that works for $20 an hour, create a package for editing complete manuscripts. For instance, you might charge $975 for non-fiction manuscripts of less than 300 pages. Creating packages like this helps people to visualize the tangible positive outcome of hiring you. It seems more concrete, and it conveys previous experience and knowledge of the industry.”

Once you’ve armed yourself with a profile that captures your skills, knowledge, and the services you offer clients, you’ll be well-positioned to attract high-paying assignments within just a short time. What you do with your newfound freedom after that is up to you.

5 Platforms to Find Freelance Jobs Today

There are lots of great freelancer marketplaces on the internet today. Here is a selection to help you get started:

Upwork: This is by far the largest freelancer network, offering something for every type of freelancer, whether you’re just getting started or you’re a seasoned pro. With its easy to use platform, this is a great starting point.

Freelancer: What makes it unique is that you can compete with other freelancers in contests. This network might appeal to you if you’re particularly competitive and want to showcase your skills.

Toptal: This network pitches itself as having the “top 3% of freelance talent.” They’re screening process is strict. But, if you qualify, you can gain access to massive clients such as JPMorgan, Zendesk, Airbnb, and more.

Guru: If you’re looking for nifty features, Guru stands out. It lets you showcase your past work and provides you with daily job-matching so that you don’t miss out on a good opportunity.

iFreelance: Most freelancer networks will take a small commission on each project you do. With iFreelance you keep 100% of what you make. This will add up over time.

Written by Winton Churchill