Veteran Freelancers: Lessons and Insights From WordPress Pros

We recently did a series talking to freelance rookies who are at the beginning of the careers. So we also wanted to talk to veteran freelancers and learn some insights from the years of experience.

A lot of wisdom comes with age (usually), and veteran freelancers have vastly different experiences and lessons to share.

What’s Changed

A lot of things change from when you start to when you “arrive” at veteran status (however you want to define that). So we explored how things have changed for these veteran freelancers:

  • Think bigger picture: “I no longer think of myself just ‘making a website,’” says Tracy Apps, “But instead I spend extra energy to think bigger picture, and develop a much more holistic solution for my clients to achieve their goals both now and in the future.”
  • Find your niche: “When I first started my freelance business in 2008, I was primarily a visual designer, working on digital layouts, templates, and mockups—my work was very broad,” says Michelle Schulp. “I greatly narrowed down the type of projects I’ll take on. My primary work is now in web design/development (mostly WordPress) and presentation design.”
  • Shift from visuals to a site’s message: “It doesn’t matter how great a website looks or how many bells and whistles it has,” says Dana James Mwangi. “If the site’s messaging isn’t clear or telling a great story then it still won’t work as well.”
  • Process: “This includes the types of tools I use to the approach I use when communicating with customers,” says Tom McFarlin. “I spend a lot of time on things related to quality such as using PSR2 standards, third-party tools to enforce modern PHP development practices, unit testing, and so on.”
  • Confidence: Tracy Apps started with a ‘the customer is always right’ mindset. But “clients very regularly ask for things that were not in their best interests,” Apps says. “Now instead of listening to what the client asks for, I listen (and question) for why the client asks. Then I pull from my expertise to solve the real issue at hand. The result was much happier clients, even when I had to challenge their requests.”

For Jared Atchison, change has been more wholesale. He’s completely moved out of freelance work and launched a product.

“After successfully freelancing for over half a decade, it got to a point where growth was getting stagnate,” says Atchison. “I started to get bored. … New projects started to feel like a ‘grind’ instead of exciting. I started to gravitate to side projects where I could do and learn new fun things.”

For some developers, that kind of success would have been great. But Atchison learned he needs something different: “I need to keep learning and taking on new challenges to feel productive. So after much self-reflecting and realizing this, I knew it was time to consider a change.”

How Do You Break Through to Success?

Perhaps the biggest question for veteran freelancers is how do you get to be a veteran freelancer? What does it take to break through and be successful?

  • Networking: “Getting out from behind my computer to attend community events, to learn, teach, and connect with others,” says Apps. “Not only does this help build my network, but also continually improves my skill set and my mental health.”
  • Consistency: “The most important thing I did to establish myself was consistently showing up,” says Schulp. “I firmly believe there is no better path to success: show up, help out, be genuine, be knowledgeable, and be honest.”
  • Systems and process: “My projects became more successful and seamless when I set up systems and workflows on how my company delivers websites from start to finish,” says Mwangi. “Now I have automated almost all the steps on what happens from the time I get an email inquiry about my services to the date I publish a client’s project. My team and I now have more time to be creative because we’re not lost in a sea of unorganized client emails or performing redundant tasks.”
  • Explaining your why: “Storytelling is the number one tool that increased awareness of my company,” says Mwangi. “In today’s digital space, people literally have millions of choices when deciding who to hire for web design. I realized quickly that doing great design work isn’t enough.”
  • Find the right people: “Surrounding yourself with people who can help you formulate clear ideas around your business helps,” says McFarlin. For him, that’s been a mastermind group—something he was initially hesitant to join.
  • Don’t go it alone: “Hands down the best and most important decision was not going down this journey alone,” says Atchison about finding success with a product. “Specifically, choosing a business partner that compliments your own skill set.”

Of course, success is relative.

“There are many places I still want to grow and improve,” says Schulp. “I’m sure my business in 10 years will be very different than my business now, just like my business now is very different than when I started out 10 years ago.”

“There’s always another hill to climb,” McFarlin adds. “No one I know who is ‘successful’ would consider themselves ‘there.’ Instead, they look back to see what they’ve achieved and then look forward to what they want to do.”

Everybody Makes Mistakes

We all make mistakes. But the key is to learn from them (“Isn’t progress just learning to fail in new and different ways?” asks Schulp).

Here are some of the common mistakes our veteran freelancers ran into:

  • Low prices: “That just didn’t fit me, and it just would burn me out with too much unfulfilling work,” says Apps. It’s a common issue—Mwangi voiced the same concern: “When you underprice you, you can’t invest in the best tools and the best people to get a project done and you can’t offer great value.”
  • Poor communication: Schulp used to think clients always needed answers, so if there was a problem, she tried to solve it before communicating with the client. But that just led to radio silence and made clients nervous. “I learned that people are more interested in feeling informed and being heard than believing you have all the answers,” says Schulp. “Sometimes just getting back to someone immediately, saying you don’t have an answer but are aware of their concerns and are actively working on a next step, is all they need to continue to have confidence in you.”
  • Owning it: McFarlin said he had made too many mistakes to count, but the key was owning up to them: “I’ve found being upfront and honest in the face of such problems can go a long way in building a relationship and trust with a customer.”

Needs Improvement

Even veteran freelancers have areas where they need to improve. That’s part of what makes them veterans—they’re always working and getting better.

  • Keep learning:
    • “Technology keeps changing, so as soon as I stop learning, I stop providing the best solutions for my clients,” says Apps.
    • Schulp agress: “I’m pretty sure I’ll never keep up with all of that, but I feel if I make my best effort and try to at least be aware of what I don’t know, I’m doing OK.”
    • “It’s hard for me to embrace the term ‘veteran’ when it comes to WordPress because it and the experience on the web keeps evolving,” says Mwangi. “As with any significant change, I’ll be rolling up my sleeves again and excited to learn something new. I know now to embrace change early.”
  • Process: “There are plenty of ways I can better automate, streamline, segment, market, and otherwise remove bottlenecks and barriers to my time and energy,” says Schulp.
  • Planning ahead: “Right now, the big thing that weighs on me is what the business may look like, say, a quarter or six months from now,” says McFarlin.
  • Managing: “At this point I spend less than half my days writing code,” says Atchison. “Instead I spend time executing marketing plans, helping our support team, doing peer reviews for our developers, and things of that nature. … So my top priority is putting in time to be the best manager and team player I can be.”

More Insights

To learn more from our veteran freelancers, check out the complete interviews:

Veteran Freelancers: Lessons and Insights From WordPress Pros

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