How To Succeed At Starting A Freelance Business In 2023 If You’re Over 50

Written By Mike Allison  |  Blog  |  0 Comments

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Have you given up on your dream of starting a freelance business because you believe you're "too old" or it's "too late?"

You've likely heard from well-meaning relatives, colleagues and friends that you should be happy that you've got a job - assuming that's still the case during COVID-19 - to count your blessings and remember that the grass isn't greener on the other side of the fence. 

Think you're too old to start your freelance business? Watch the video below about Julia Hawkins, who at 102 broke a world record for the 100 meters by female competitors over 100.

Maybe you've heard that being a freelancer sounds great, but it's not all it's cracked up to be because you've got to go out and find your own customers and no one's going to be there to catch you if you fail. 

Am I right? 

how to succeed at starting a freelance business

How To Start a Freelance Business When You're Over Fifty

Well, know this, I've heard all of those things in the past, too. But, I wouldn't trade being a freelancer for taking a so-called "secure" job from anyone. 

Here are some of the places my freelance work has taken me: Moscow, Rome, Madrid, Prague, Berlin, London, Stockholm, Singapore, Seoul, Taipei. 

Each city has a unique culture and vibe.

They are world-renowned, with long histories, great food, and amazing people. I would never have traveled to most of those cities if I hadn't been a freelancer. 

Under Armour, Johnson & Johnson, Bayer, Maersk, HSBC, Mattel, Hasbro, VF Corporation. 

Each company has a unique workplace culture and atmosphere, and I've worked with talented and energetic people in all of them. When I started freelancing in 2006 at 46 years young, I didn't know I'd have the chance to work inside some of the world's largest organizations in 15 countries.

When I decided to freelance, I made a great choice. I gained valuable experience, developed new skills, met interesting people, and worked in cities many people dream about visiting.

Why You Should Start A Blog In 2023 - 16 Reasons To Start Blogging In 2023

I don't travel for work anymore, but I still freelance as a digital content creator, copywriter, and blogger. 

Freelancing lets me work for myself. I have the freedom to decide what type of work I do and how much time I spend doing it.

I'm aware freelancing isn't for everyone, but since you're reading this post, I'm assuming you're doing it already, or you're giving serious thought to starting.  

A lot of people lost their jobs because of COVID-19, and if you're in the 50+ age group, you're facing a particularly challenging situation. It may not be easy for you to find a new job, and this fact has made the idea of freelancing more appealing to many.

If you're considering using your years of experience, skills, expertise, and knowledge to start freelancing, then I say, "good for you," and I want to give you some pointers on how to start your freelance business in 2021 and succeed at it. 

To start, let's look at the pros and cons of freelancing.

The Pros Of Being A Freelancer

  • As a freelancer, you have the freedom to decide what to do and the amount of time to spend doing it. You also get to choose your customers, something you can never do if you're working for someone else. 
  • You decide on the strategy and tactics you're going to use to achieve your business goals. 
  • You can earn more per hour as a freelancer than as an employee of a company. 
  • Depending on what you choose to do, you can work from anywhere; you only need a laptop and an Internet connection. I work from home, so I never have to deal with traffic jams.
  • You don't have to sit through the bi-annual performance review because you are the only person reviewing your performance. 
  • You have a lot more time to spend with your family, especially if you're working from home. 

The Cons Of Being A Freelancer

  • Freelancers lack a guaranteed income.
  • You won't be reporting to anyone else, which can be a problem if you lack good habits.
  • Many freelancers are easily distracted by things that don't contribute to their business goals.
  • When you freelance, you're the boss, so you're responsible for everything that happens in your business.
  • Some freelancers miss working in an office and being part of a team.
  • You may face a lot of pressure from family members and peers to stay with your job and a guaranteed income.

These are some of the pros and cons that freelancers deal with daily, and as Miguel de Cervantes said: "Forewarned, forearmed; to be prepared is half the victory."  

In the rest of this post, I'm going to share the most important things you're going to need to start your freelance business in 2021 if you're over 50 and succeed at it.

How To Start a Freelance Business Starts With Success Thinking

This is about how you're going to measure success. 

I'm starting with this because the way you think about success is going to make or break you.

We need a reality check to put everything into perspective and ensure that you prepare yourself mentally before you start on this journey.

If you're on Linkedin, you'll notice that there are hundreds of thousands of freelancers, and some of them have tens of thousands of followers and connections. Many are coaches and consultants of various stripes.  

What if I told you that a large percentage of them, with all of those connections and followers, barely earn enough money to live? 

I've talked to dozens of freelancers before I completely deleted my LinkedIn profile and left the platform for good, and most of their businesses are feast or famine.

You don't need LinkedIn to start a freelance business

Now, I'm not suggesting that you need to be earning X amount of dollars to be successful. The way you measure success and the way I measure success is not going to be the same, and that's fine. 

With that said, there are two things I strongly recommend you decide before you launch your freelance business.

  1. How much you need to earn annually to be happy, satisfied, and left with a clear conscience. 
  2. How much time you're able to commit to your freelance business.

Think carefully about the first point. You might be dreaming of building a freelancing empire by starting small and scaling your business until you're earning a seven or eight-figure income. 

If that sounds familiar, it's because YouTube and other social media platforms are full of ads with self-proclaimed gurus claiming they've gone from zero to seven figures in one year, and they're going to show you how to do the same thing if you sign up for their webinar.

FACT:  Most of the men and women who've created those ads haven't built anything other than the training program they're selling. They show faked screenshots of their income, film themselves inside the mansions they've rented for the day, and drive around in their rented Ferraris and Lambos. 

Pipe dreams of starting a freelance business

Don't get sucked into their pipe dreams and false promises. I don't know any ethical multi-millionaires who were able to achieve their levels of income in just a few months. 

That's why you need to decide ahead of time how much money you need to make each month to feel happy, satisfied, and left with a clear conscience. But here's a tip. 

Research has shown that once a person exceeds an annual income of about $95,000.00, their levels of happiness and life satisfaction do not go up, and as income increased, levels of happiness dropped.

If your measure of success includes feeling happy and satisfied, you can see why I've included this as the first point. It's because I want you to be a happy and satisfied freelancer, not an unhappy, stressed-out one. 

If your goal is to earn seven figures, but doing so means you've got to spend half of your time away from your family and home, how happy do you think you're going to be?  

That takes us to the second point, which is the amount of time you're able to commit to your freelance business.

Notice how I've worded that: "able to commit" instead of "willing to commit?" You might be willing to commit everything to your freelance business.

But are you able to do that and still have a great family life? Are you able to do that and maintain great friendships? Are you able to do that and stay physically, emotionally, and mentally healthy?

how to succeed at starting a freelance business

It's important. Be honest with yourself when answering the second question. Remember: I want you to be a happy, healthy, and satisfied freelancer. Not a stressed out, burnt out, lonely one. 

Let's move on to:

Do a Personal Audit Before You Start a Freelance Business

 Knowing how to start a freelance business if you're over fifty starts with making a great big, long list of the knowledge, experience, natural abilities, skills, and talents you've developed that you could teach to others to help them solve problems they're facing or for making personal/ business improvement.  

KEY POINT: Write down everything that comes to mind. Additionally, ask the people you're closest to what they would say your most outstanding skills, natural abilities, and talents are. 

If they were going to choose one thing that you should help others learn to do, what would they choose?

Get as many ideas as possible. Once you've completed your list, it's time to decide what you're going to focus on doing as a freelancer. 

Now that you've got a list of ideas, you need to know if there's a market. As long as other freelancers are selling the type of service or product you've come up with, you know you've got an opportunity. 

Below is a list of services that freelancers are already making money selling. 

Graphics & Design

  • Logo Design
  • Brand Style Guides
  • Game Art
  • Business Cards & Stationery
  • Illustration
  • Brochure Design
  • Poster Design
  • Flyer Design
  • Book Design
  • Album Cover Design
  • Packaging Design
  • Web & Mobile Design
  • Social Media Design
  • Catalog Design
  • Portraits & Caricatures
  • Cartoons & Comics
  • Photoshop Editing
  • Architecture & Interior Design
  • Building Information Modeling
  • Character Modeling
  • Industrial & Product Design
  • T-Shirts & Merchandise
  • Presentation Design
  • Infographic Design

Digital Marketing

  • Social Media Advertising
  • Social Media Marketing
  • SEO
  • Public Relations
  • Email Marketing
  • SEM
  • Marketing Strategy
  • Web Analytics
  • Mobile Marketing & Advertising

Writing & Translation

  • Articles & Blog Posts
  • Proofreading & Editing
  • Translation
  • Website Content
  • Product Descriptions
  • Book & eBook Writing
  • Resume Writing
  • Brand Voice & Tone
  • Email Copy
  • Technical Writing
  • Sales Copy
  • Press Releases
  • Scriptwriting

Video & Animation

  • Whiteboard & Animated Explainers
  • Video Editing
  • Short Video Ads
  • Animated GIFs
  • Logo Animation
  • Intros & Outros
  • Character Animation
  • 3D Product Animation
  • Lyric & Music Videos
  • Live-Action Explainers
  • Visual Effects
  • Product Photography
  • Local Photography

Music & Audio

  • Voice Over
  • Mixing & Mastering
  • Producers & Composers
  • Singers & Vocalists
  • Session Musicians

Programming & Tech

  • WordPress
  • Website Builders & CMS
  • Game Development
  • Web Programming
  • E-Commerce Development
  • Mobile Apps
  • Cybersecurity & Data Protection
  • Chatbots
  • Data Analysis & Reports


  • Market Research
  • Business Plans
  • Presentations
  • Sales Training
  • Sales Coaching
  • Business Coaching
  • Soft Skills Training

That's a long list, and it isn't exhaustive by any means. Now, don't be scared off by the fact that your idea may have a lot of competitors. Competition equals opportunity because a competitive market gives you a chance to differentiate yourself from everyone else. 

You're going to learn more about that in the next section on Target Market, but there's one last thing you need to do. 

DO NOT omit this!

Let's imagine you have six marketable ideas on your list that you could sell as a service or product. Are you going to do all of them? The short answer is no. Why not do all of them? 

Because it's a good bet that you don't enjoy doing each of those things, right? Remember, one of the pros of freelancing is you have the freedom to decide what to do and how much time you're going to spend doing it. 

So, ask yourself this simple question: "Which of these ideas will give me the most joy, satisfaction, and contentment from teaching others to do it?"

succeed at starting a freelance business

Photo by Natasha Fernandez from Pexels

Think carefully about the answer and then choose one, and one only, of the ideas on your list. That's it. Now you have your marketable idea. But, we still have some narrowing down to do in our next step. 

Niche Down To Start A Freelance Business

A niche is a specialized segment (a group of people or businesses) of the market for a particular product or service, as in: "We believe we have found a niche in the market." 

You'll have an advantage by finding a niche in the market for your product or service. Why?

Because if you try to target everyone, you'll end up attracting no one. Niching creates focus, which makes your life as a freelancer a lot easier. You're only creating products or services to serve a specific part of the bigger market. 

And trust me when I say that having focus is crucial when you're in business, and more so when you're getting started.  

Niching also positions you as an expert within a specific area of the market, something that is vital to your business success. People want to work with an expert. 

Let's look at some real-life examples of individuals who have had business success by focusing on a niche in the market. 

Nerd Fitness

freelance business success

Steve Kamb started the company in 2009 as a simple blog. The front page of the website states: "We help nerds, misfits, and mutants lose weight, get strong, and get healthy permanently!"

It's is a brilliant example of niching down to serve a specialized segment of the health and fitness market.

Here's another one.  


Shirts Designed To Be Worn Untucked

The company sells shirts that look good untucked. It's a niche inside of a massive market, men's shirts. Chris Riccobono had the idea and started in 2010 when he created the Original Untucked Shirt. He then brought on a classmate from Columbia University, and there are now 80 stores in the U.S. 


She Writes

She Writes

"It's the largest online community for women writers at every stage of their writing lives, working in every genre and representing every generation-all around the world."

Kamy Wicoff created the content site in 2009. In 2012, Wicoff and Brooke Warner founded She Writes Press, the hybrid publishing arm of She Writes. 

The "She Writes" community includes more than 32,000 members and more than 350 groups. 

These are just three examples of niches. Does this mean you can never reach out to serve a larger part of your market? No, but when getting started, it's best to focus on a specific segment. Most freelancers find that once they have established themselves in their niche, their market tends to expand all on its own.

Will Your Freelance Business Be A Product, Service, Or Both?

Are you going to be selling a product, service, or a combination of both?


Yep, both. Software is both a product and a service. For example, I use Grammarly to write my blog posts. It's an AI software that is scanning the text in real-time and informs me when I need to make corrections or adjustments to voice, grammar, and so on.

The SaaS (software as a service) market is massive and growing. You might have an idea for a service that could also become a software product you could sell to help solve a problem in the niche you've chosen. 

Adobe, Microsoft, Oracle, Intuit, Salesforce - each of these are well-known SaaS companies. Besides these large companies, there are thousands of smaller SaaS companies that serve small businesses and freelancers.

In the Personal Audit section of this post, I listed some of the services freelancers are providing. You'd be hard-pressed to find freelancers in any of those niches who aren't using some form of SaaS. 

My point here is that creating a SaaS could be a great idea to pursue. But, what if you have an idea but absolutely no coding skills to write the software? 

You can find people who will do everything for you, assuming that you can fund such a project. Check out this post for an example.

start a freelance business

You might also have an idea for a physical product which you plan to sell online or door-to-door. If you want ideas on how to do this, check out this post: Find a Product to Sell Online: 12 Strategies for Finding Your First Profitable Product on Shopify's site. 

Here's another high-value source on this topic: What To Sell Online: 21 Product Ideas That Drive Ecommerce Sales

As I mentioned at the beginning of this post, as a freelancer, I was selling a service. There was no software or any physical products.

My services included customized soft skills training design and conducting workshops. Our clients could also purchase one-on-one and group coaching programs for their employees.  

We conducted all of our training workshops in person, on or off-site, depending on the customer's request. That required traveling, often long distances, and through several time zones. 

If you're going to be selling a service, you should decide ahead of time if you're going to stick to working 

  • online only
  • online and face-to-face in your local area
  • online and face-to-face in your local area, as well as country-wide or even internationally. 

Making these decisions before you begin freelancing will help you to know what projects and customers you can say yes to and those you're going to turn down.

For instance, if you've made a firm decision to work online only, you've got focus. You know what you can and cannot do online. If a prospect requests you travel to them for a project, you don't need to hem and haw, because you only provide your service online. 

Decision-making is easy when you're clear on your product, service, and method of delivery.

Marketing Your Freelance Business

The fastest, most powerful way to market your new freelance business is word-of-mouth, especially when you've been working for 20 or more years in a specific industry or field. So let your former colleagues and employers know what you're doing. They may even become your first customers. 

We had this experience when we started our consulting and training company in China. Our first customer was New Balance. I knew the HR Director from the company that had laid me off. Once we started our own company, I informed her that we were in business, and she agreed to meet with me to discuss their training needs, and that meeting resulted in our first contract. 

Attending local conferences and networking events where you can meet people in your target market is also an effective way to market yourself and your freelance business. Check out Eventbrite for events in your local area.

marketing with eventbrite

And since I've referenced Eventbrite above, you could run an event yourself, either online or live, and advertise it on a platform like Eventbrite.  

We used this method in China to showcase a part of one of our training workshops. We would rent a conference room, invite 50 - 60 training managers and HR directors, and do a three-hour demo of one of our two-day workshops. 

Events like these were an opportunity for people in our target market to network while experiencing our training content and methods. 

Content marketing is also a powerful strategy. One of the easiest ways to use content marketing is by starting a blog

Remember Steve Kamb, the founder of Nerd Fitness? On his website, he wrote: "I started Nerd Fitness in 2009 as a simple blog and have been publishing 1-2 articles per week ever since."

start a freelance business

Nathan Barry, the founder of ConvertKit, wrote that all of the good things that have happened to him in his career came from writing 1,000 words every day. That habit revolutionized his career.

start a successful freelance business

Nathan Barry

If you get into the habit of writing about what you know and provide high-quality and valuable content for your readers, you'll establish your authority and expertise. You'll build an audience that likes you and trusts you. That audience will be willing to pay you to help them solve their problems and achieve their goals.  

I've written a post on the subject of habits for content marketers which you can read here: 5 Habits Every Content Marketer Should Develop.

Once you get into the habit of blogging, it's not a stretch to extend that into writing a book on the subject you're an expert in, and publishing a book is easier today than ever before. Authoring a book establishes your expertise and is a great marketing tool.

Email marketing works side-by-side with your blog to help you grow a list of subscribers. Many freelancers will tell you that "the money is in the list." An email list is like a valuable piece of real estate. Through email you can build a relationship with your audience by giving them the exact help they're looking for to solve their problems and find success. 

Starting a YouTube Channel is another great marketing strategy. People love to watch videos. 

Research by Forbes Insights reveals that video is becoming a critical information source for senior executives. 

YouTube is the 2nd most popular social media platform in the world. 1.2bn people use YouTube. It's also the world's 2nd most popular search engine behind Google. The best thing about YouTube is that you can start marketing your business there without spending a cent.

I don't know of any successful freelancers who are not using YouTube for marketing themselves and their businesses.

If you do have an advertising budget, paid ads on YouTube and Facebook can be an effective way to market yourself, and for as little as five dollars per day. 

If you decide to do some paid advertising, the first step should be educating yourself about the platforms that are going to work best for you and how to create and test your ads. 

I've learned a lot from Jason Whaling's videos on YouTube. He's got a lot of relevant and valuable content about $5 YouTube Ads for accelerating your YouTube channel's growth. 

freelance business successful start

I'm confident that starting with a couple or even all of these marketing methods - word-of-mouth, content marketing, a YouTube channel, free online or live events, writing a book, and paid advertisements - your audience and reach will quickly grow.

Finally, let's consider how to keep yourself sane and having fun while you also keep your business running. 


If you want to keep your business going, you need to pay attention to the things that are going to help you sustain it. 

Boundaries - right from the start, I recommend you set boundaries between your work and personal life. 

If you're working from home like I am, you've got to have limits. If you don't, you're going to find yourself working when you should be doing more important stuff, like spending time with your family.

start a successful freelance business

Photo by fauxels from Pexels

So, set strict work hours and stick to them. When it's time to stop working, stop working, and do something else. The last thing I want you to experience is burnout. Too many freelancers end up stressed to the limits and, in the end, lose the joy, excitement, and happiness they had when they started. 

You don't need to be one of them.  

Continue learning, so you become more knowledgeable and skilled in your area. Whether you're teaching others a hard skill or a soft skill, you need to be a lifelong learner first. Continuous improvement should be one of your main goals. 

We have access to unlimited learning at the touch of a button or click of a mouse. There is so much information at our fingertips today that there's no excuse for not becoming better at what you're doing.

Integrity is non-negotiable, so always conduct your business in complete transparency. Never lie to your audience and customers. 

It can take years to build the trust of your audience, but you can destroy that trust in an instant with one lie. People might still do business with you, but they will never forget that you lied to them. 

Never promise people things that you know you can't deliver. Don't exaggerate the results you can help people to achieve. Under promise and over deliver is a recipe for success. 

a successful freelance business is based on integrity

Serve people first, sell to them second. If you approach your business and your customers with a service-first attitude, you'll find that you have an audience that loves what you do, sticks with you, and tells others about you. And they will also buy from you.  

Inspire your audience by what you do. Actions speak louder than words. Let the people you're helping see you applying what you're teaching and the positive results it's having in your life and business. That will inspire them to do the same and lead to more sales because people will want you to work with them. 

Impact your audience by giving them practical advice to help them quickly solve a problem they're facing. Help move from the current situation to the desired state. That's impact.

How would you answer?

  • What is success thinking and why is it important?
  • Why should you niche down inside your market?
  • What are some of the ways you can use to market your business and which ones are you going to start with first?
  • What are 6 aspects of sustainability referenced in this post?
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