F50 Issue #25: Seven Roadblocks to Your Freelance Success


F50 Issue #25: June 25, 2024


Seven Roadblocks to Avoid on Your Journey to Freelance Success

Years ago, the freelance journey seemed like uncharted territory. If you told people you worked from home, you might have faced quizzical looks: “What do you mean you work from home? How do you get anything done?”

Others might have said you’re lucky. It takes courage to pursue a freelance career, but the rewards are invaluable. One of our favorite quotes comes from a poem by Robert Frost called “The Road Not Taken”

“Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.”

These days, you’ll discover the road to freelancing is more frequently traveled. In fact, 64 million Americans worked as freelancers in 2023, according to a survey released by Upwork, the online work marketplace. This adds up to 38% of the total workforce in the United States.

And among those U.S. freelancers, 8.3 million (13% of them) were 59 years old or above.

According to Margaret Lilani, VP of talent solutions at Upwork,

“An increasing number of Americans are seeking greater flexibility, autonomy and earning power when it comes to their work, and they are finding it with freelancing.”

But how do you get there and achieve the success you’re looking for? As the journey begins, it’s easy to get caught up in roadblocks that prevent you from reaching the flexibility, fulfillment, and financial opportunities that await.

You might feel like Neal Page, the marketing executive played by Steve Martin in the 1987 movie Planes, Trains and Automobiles. All he wants to do is get home for Thanksgiving, and he faces stolen cabs, flight delays, and all kinds of obstacles.

When all you want to do is start freelancing after 50, seven common roadblocks can get in your way. As we unpack them, note which ones you most relate to.

Seven Roadblocks on Your Journey to Freelance Success

1. Unclear vision in your midlife

What would you like to achieve at this stage of life? Years ago, you might have wondered, “What do I want to be when I grow up?” And now that you’ve grown up, it’s hard to imagine what else you can do.

Or maybe you’ve conditioned yourself to accept the idea that you need to retire after 50. The phrase “Freedom 55” conjures up images of endless days on the golf course or the beach. But sometimes that doesn’t sound appealing either, and you’re stuck.

Without a clear vision of the options you have in your midlife, you don’t know how to move forward with a freelance career.

2. Uncertainty about your best skills and abilities

After developing a wealth of experience and skills in another profession, you wonder how they could possibly translate to a viable freelance business. Can you continue a similar kind of work as a freelancer? Do you need to start from scratch and learn a whole new set of skills?

And what about your unique personality traits? Which ones are best leveraged to create a successful freelance career? Sometimes it’s hard to know how to assess yourself so you can pack the essentials and head out on your journey.

3. Confusion over which freelance career or niche to choose

Sometimes you’re staring at the map, confused over which destination to head to. With the growth of freelancing, the number of choices can seem overwhelming. There are so many interesting paths, and you don’t know which one to pursue.

Maybe you’ve explored some already and feel like you’re going in circles. You’re eager to know which services are in demand for people over 50 and which ones would suit your skills and interests.

4. Inability to create a clear freelance offer

In your current or previous career, maybe you received a salary, and the company you worked for defined your job description. When you become a freelancer, however, all of a sudden you get to design your own job description and set your own rates.

This freedom can be a breath of fresh air. But success remains out of your grasp when you’re not sure how to package, price, and present your services. It’s like you’re excited to board the train, but you can’t quite reach the step and journey toward a solid freelance income.

5. Confusion over how to build your digital footprint

Some of us who are over 50 didn’t grow up with computers, and we’re still learning how to best use the internet. Others are adept with technology, but the idea of an online presence is new. When you journey down the freelance road, you need to build a digital footprint that will lead people to you and your freelance services.

This can seem daunting if you’re struggling to understand how to build a strong online presence that stands out in your chosen market. And not only that — you may also feel discouraged, wondering how you can stand out among younger freelancers.

6. Difficulty knowing how to find clients and build a freelance income

Sometimes a paralyzing doubt sets in. Maybe you’ve assessed your skills, figured out your niche, created your freelance offer and online presence … but you’re at a standstill. Clients are elusive, and you wonder if you’re cut out to keep traveling down the freelance path.

Now is the time to pack some proven strategies into your suitcase to help you promote your services. That way, you can find ideal clients and start generating an income.

7. No clear goals or action steps

Here you are, with the road stretching out before you. Are you going to take your first step? You may be thinking, “What is the first step?” And that’s the seventh and sometimes biggest roadblock — knowing where to begin.

Without clear goals or action steps, it’s impossible to know how to launch and grow your freelance business. You need an actionable, step-by-step plan to help you chart your course.

To avoid these roadblocks, join us for an exclusive LIVE workshop on June 26th at 5 pm PT (8 pm ET). We’ll provide a seven-step roadmap to starting a successful freelance business so you can overcome uncertainty and gain confidence in your decision to start the journey!

If you’d like personalized support, you can also stay for the Q&A session, where we’ll give you tailored advice to any pressing questions. To guide your journey, you’ll receive a “Freelance After 50 Roadmap” workbook and lifetime access to the workshop replay so you can review the material anytime.

We’re here for you, and we’re excited to help you thrive in a rewarding freelance career at any age!


A Bit of Nostalgia

Screenshot via https://computerhistory.org/exhibits/hello-the-mac-at-40/

Does that computer screen look familiar? Well, the Macintosh computer turned 40 this year! It was born on January 24, 1984, and shows no signs of retiring yet.

Earlier this year, the Computer History Museum hosted a mini pop-up exhibit in Mountainview, California, and is still displaying artifacts on its website.

And if you enjoy tech and would like a more detailed walk down memory lane, check out this article from PC Mag: “40 Years of Macs: A Look Back.”


Words to Live By

“Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover." — often attributed to Mark Twain

Here’s to clear sailing and the courage to begin a journey of discovery. Hope to see you on June 26th, so we can help you take those first steps together!

Until next time,

Craig & Kelly

P.S. Remember to secure your seat in tomorrow's exclusive workshop and get a 7-step roadmap to launching a thriving freelance career after 50!

Co-founders of Freelance University

431B 41st Avenue NE - Unit 94, Calgary, AB T2E 2N4
Unsubscribe · Preferences

Freelance After 50 Newsletter

Ready for an exciting new chapter in your life? Join 8000 subscribers who are pursuing a second-act freelancing career to gain the income, flexibility and freedom they desire!

Read more from Freelance After 50 Newsletter

F50 Issue #26: July 9, 2024 What Do You Want to Be When You Grow Up? “What do you want to be when you grow up?” It’s a question many of us were asked when we were kids. Maybe you asked yourself this question. You may even remember school assignments where you wrote about or drew a picture of what you’d like to be when you grew up — childlike descriptions of common professions and some entirely made-up ones. And you had to have this question figured out by when? High school graduation?...

F50 Issue #24: June 11, 2024 Be Your Own Biggest Fan: Lessons from Unretiring Athletes Imagine you’re competing for the championship trophy in a popular sport. As the clock ticks down, you’re poised to score the winning goal. During the last few seconds, you look up at the stands for support. Scanning the crowd, you see a row of people cheering you on — friends, family, whoever is nearest and dearest to you. And … wait a minute. Who’s that? Are your eyes deceiving you? You see YOURSELF...

brown dried leaves on sand

F50 Issue #23: May 28, 2024 Mindset Matters: How to Build Healthy Habits After 50 In the 2002 movie About a Boy, Hugh Grant plays a character named Will Freeman. If you’ve seen the movie, you may remember that Will saw himself as an “island” — a free man with no responsibilities and obligations to other people. Because he inherited royalties from his father’s hit Christmas song, he didn’t have to work. Instead, he carefully carved out a lifestyle with daily habits that enabled his brand of...