The road to launching a successful freelance writing business can be long and arduous. But you can take some comfort in knowing that others have blazed a path before you.
True, everyone’s journey will be different. But many of us will face (and have faced!) the same challenges and misconceptions.
I walked that path myself when I launched my own freelance business many years ago. And as a coach, I’ve been fortunate to witness and share in the journey of hundreds of other freelance writing professionals. And I can say, without hesitation, that every single one of them has valuable lessons to share.
Learning from their experiences can save you a lot of time and misplaced effort. It might also assuage some of your doubts and fears.
So take a moment to learn from those who’ve gone before you. Below, 10 writers and copywriters share big lessons learned from launching their freelance business.
Leverage your background and relationships
Of the many things you can do to help ensure the success of your freelance business, leveraging your background and relationships is one of the most powerful. And this is especially true if you left a high-level position in an established industry to go solo.
This was the case with Ted Goldwyn. Ted left his position as a senior executive at a credit union in 2014, after spending almost 20 years in the banking industry. He recognized that his experience as a financial services provider uniquely positioned him to market to similar providers.
So Ted quickly set up his business and reached out to his contacts.
“I had the outline of a business plan,” says Ted. “I had a makeshift website that I put up in a matter of days, and I had some income goals and projections for my first year. I also started leveraging prior contacts and utilizing social media, particularly LinkedIn.”
Thanks to that initial outreach, Ted landed three clients within his first two or three months.
Of course, not everyone has an executive background they can leverage. But that doesn’t mean you don’t have other assets you can work with.
Daniela Llanos, for example, is a mechanical engineer with 10 years of experience. When she decided to launch her B2B copywriting 
business, she quickly realized that this venture was going to be a different kind of challenge.
“I had a company name. I had a website. I had spoken to a few people,” she says. “But I hadn’t gotten a paid client—or an unpaid client, for that matter. I was buying as many educational programs as I could and not getting anywhere. I had no direction.”
Daniela and I started working together about a year ago. We used her background experience to strategically position her and to highlight her credentials in the HVAC (heating, ventilation and air-conditioning) industry.
Within a few weeks, she landed her first paid client—a critical milestone that propelled her business forward.
But what if your background is in an industry that’s notoriously short on funds? Then you might have to get a bit more creative with your positioning.
For example, Joseph Cole’s background is with nonprofit organizations. Most nonprofits are highly budget conscious, which can make marketing to them a challenge.
But after working with me in my B2B Biz Launcher coaching program, Joseph repositioned his business not to target nonprofits but to target other companies that sell to nonprofits. Turns out these companies highly value Joseph’s insider perspective and have the budget to pay for it!
This new angle was a game changer. Joseph was able to quit his day job last year to freelance full time—a longtime dream of his. We talked a few weeks ago, and he’s booked solid with client work for the next few months!
No recent work experience? That’s OK!
What if you don’t have any recent work experience? What if you’ve been out of the workforce for years? Or even decades?
Lack of recent workplace experience might mean that you have to work a little harder to find your first few opportunities. But once you land your first couple of clients, you can develop momentum quickly.
Take Jeanne Noorman, for example. Jeanne is a freelance copywriter from Michigan. She was out of the workforce for 24 years, 17 of 
which she spent homeschooling her kids. When she decided to launch her freelance business in 2013, she worried that her lack of recent work experience and professional contacts would dampen her success.
But Jeanne decided to go for it anyway. She and I worked together to leverage what she did have—writing skills and teaching experience. And by taking small steps, she made progress.
“My first projects were writing the web copy for a friend’s new business and a bio for another friend who was changing jobs. I did both projects for free,” she explains. “Since then I’ve capitalized on small wins, I network both online and in person, and I continually ask for referrals.”
Today, Jeanne’s business is thriving. She recently told me that she’s on track to have one of her best months yet. She’s adamant about the importance of taking consistent action, especially when you don’t have a long career or a professional network to leverage.
“You have to get out of your comfort zone and act!”
Age is not a factor
I’ve had hundreds of conversations with new and aspiring freelancers who are over the age of 55. And the most common concern I hear is “I’m afraid that my age will prevent me from getting clients.”
I understand this fear. Especially if you’ve experienced age discrimination in the workplace or have been laid off or downsized because of your age. (Something an employer would never admit to!)
But age comes with certain benefits. In fact, your experience, wisdom and perspective can give you a competitive edge over younger freelancers.
And that’s not just my opinion. I’ve heard this from several freelancers who launched their solo business later in life.
For example, Katherine Andes is a California–based web content developer and SEO writer who went solo 12 years ago at the age of 54. And she feels that her age gives her a real advantage.
Most of her clients are seasoned business owners who appreciate her maturity. They trust her. She’s not a budding SEO hotshot who overpromises. And she attracts clients who specifically don’t want a “young and cool” vibe.
Similarly, Steve Brockwell turned to freelancing after a long and varied career in magazine journalism and communications, having worked in insurance health care and nonprofits. As an employee, he’d done a lot of B2B writing and content marketing. And all those years gave him time to hone his craft.
“It became evident to me that B2B [writing] was the best place for me,” he says. “It’s the world I was used to being in.”
In addition, those years spent in the corporate world kept him motivated.
“I thought [about it and decided that I just didn’t] want to go back to that kind of corporate life. I had to keep going.”
You have to HUSTLE!
Success is always right around the corner. The problem is, you don’t know which corner. It could be the next one. Or it could be corner number 224!
In the meantime, you have to hustle. You have to take consistent, massive action to stay in the game and get results.
Adria Schmedthorst is a great example of this. When I first met Adria, she felt stuck. She’d been trying to launch her freelance copywriting
business but just couldn’t get it off the ground.
But Adria persisted. She started by sending warm emails. Lots of warm emails. In fact, she sent out 171 emails before she landed her first client. Then it took another 100 or 120 emails or so before she landed her second client.
What kept her going?
“I was scared to rest,” she admits. “I wanted to keep going. I didn’t want to be back in the same position with no clients again.”
So she persevered. And her consistent action paid off—big-time.
I ran into Adria two months ago at a copywriting conference. She reported that she has plenty of interesting assignments and an impressive number of referrals from happy clients. And she has some serious momentum going into the upcoming year.
Her advice: “It’s the law of averages. Just keep pushing, and eventually it’s going to work.”
I can identify with Adria’s experience. When I started my freelance business in September 2003, I spent five months throwing spaghetti at the wall with almost zero results to show for it.
I then worked with a business coach and revamped everything I was doing. But even then it took nearly six months of serious work to land my first client.
What kept me going? As with Adria, I felt I had no choice. Staying in my current job and my current career path wasn’t an option. So I kept going. And I kept hustling.
Eric Lynch also knows how to hustle. He has 22 years’ experience as a software developer, programmer and sales engineer. In March 2015, he left his position as CIO so he could combine his technical expertise and writing chops as a freelancer.
To land clients, he followed my Warm Email Prospecting program. Initially, the results were slow. But then a no from a prospect caught his attention.
“In my warm emails, I wrote that I know how to write for CIOs,” he notes. “This prospect stated that they weren’t interested because they don’t target CIOs. This made no sense to me.”
So Eric decided to give them a call.
“The prospect clarified that while they don’t target CIOs, they do target technical architects. Did I know how to write for technical architects? Well, yes, I do!”
Once Eric made this small change in his marketing, the floodgates opened.
Even with this success, Eric hasn’t stopped hustling. Every morning, without fail, he sends out five to ten warm emails. And that adds up over a period of weeks and months.
As a result, Eric’s pipeline is full, and he’s even farming work out to other writers!
Les Worley also had to hustle to get to where he is today. Les’ background is in software development and IT, and he worked as a IT director for many years.
For him, writing was easy. Building a book of business, however, was not. When he first launched his business, he had specific ideas about the kind of writing he wanted to do and the kinds of clients he wanted to serve. But he soon learned the benefits of staying open to other opportunities.
“I worked with Ed in 2014, and he encouraged me to step out of my comfort zone. I decided to submit a spec copy assignment to a AWAI contest to stretch myself. I ended up winning that contest—which opened a lot of doors.”
Les also decided to give agency work a try, even though some freelancers frown on it.
“I really had to prove myself to get that initial agency work,” he says. “When the agency lost one of its writers, I was able to step in and help them retain a valuable client. As a result, they offered me a large monthly retainer to continue with them.” Today, that large retainer makes up the bulk of Les’ income.
But landing that large retainer doesn’t mean Les has stopped hustling.
“You can’t get too comfortable,” he warns. “Clients leave. Retainers get cancelled. You need to keep up with your warm email prospecting—even when you’re fully booked.”
A roadmap and guidance
When you’re launching your freelance business, it’s all too easy to make costly mistakes and get off track. So for many freelancers, a proven roadmap and ongoing mentoring are critical to their success.
This is something Steve Brockwell realized very early on.
“I had no idea how to pull this off,” he admits. “Where do I start? How do I do this? I had zero experience with people who’d actually made a living at this kind of thing. I needed to connect with real people with real experience.”
To get the kind of guidance he was looking for, Steve and I worked together through my B2B Biz Launcher 2.0 coaching program.
“I realized I needed a mentor type of relationship,” he states. The mentoring and support gave Steve the confidence to build a successful and growing business.
“Right out of the gate, it gave me more confidence to get going,” he notes. “At every juncture, the resources I needed were there.”
Even if you have the first steps figured out, a roadmap and mentoring can help keep you on course, as Jennifer Alwood found out.
“I need structure,” she says. “I need to know what my next step should be.”
That was a key deciding factor in Jennifer’s decision to enroll in my B2B Biz Launcher 2.0 coaching program.
Having a roadmap gave her the confidence to reach out to new clients and respond to client requests. She adds, “It was a framework I could follow with confidence, knowing that it was going to work.”
Daniela Llanos already understood the value of having a roadmap and mentoring, thanks to her engineering background, where mentoring is a common practice.
She explains, “Starting as a junior engineer, you work under a senior engineer. You learn how everything works. And not just the technical stuff but also project management and how to deal with people.”
And while Daniela acknowledges that many new freelancers are keen to take courses to get started, courses aren’t always enough.
“When you’re doing a course, you’re not getting feedback per se,” she notes. “You’re getting information, but you’re not always sure how to apply it.” Mentoring helped fill this gap.
“You need somebody,” she says. “You need a coach or a mentor. You need somebody to give you feedback—that’s a big thing.”
Motivation was Adria Schmedthorst’s primary reason for seeking out a roadmap and a mentor. She had tried coursework but wasn’t fully implementing what she learned.
She explains, “No matter how much you spend on copywriting programs and seminars, you still have to apply what you’ve learned. You have to motivate yourself. And for me, the motivation is often gone the next day.”
Having a roadmap and a mentor helped keep Adria accountable and her motivation high.
“In Ed’s program, we were held accountable every week,” she states. “Everything was guided. I wouldn’t have started without it, honestly. Unless you have perfect discipline, doing it by yourself is so hard.”
None of this to suggest that you can’t build a successful freelance business without a roadmap and a mentor. People do, of course. But it’s likely to take longer. And maybe you’re fine with that.
But consider the opportunity costs. How many frustrating, low-income years could you potentially leapfrog with a roadmap and a mentor?
In addition, the longer you take to achieve your goals, the higher the probability that you’ll lose hope and quit altogether.
Without a roadmap and a mentor, you’ll need more resolve, more determination and more strength to persevere.
In other words, having a proven roadmap and a mentor is a way to improve your odds.
And when it comes to your dreams of a freelance writing career, why not give yourself the best possible odds?
Need help?
Tired of doing this all on your own?
Want me to help you break through that $1,000-per-month income ceiling as a freelance B2B writer or copywriter?
Here’s how we could work together starting next month.
