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6 Struggles WordPress Entrepreneurs Face

6 Struggles WordPress Entrepreneurs Face

Maybe one of the reasons I like the stories of entrepreneurs so much is that they do, indeed, read like a story. I’m sure that writers and screenwriters (for movies) use a little “literary license” to make it more entertaining and thereby forcing the story format to make it more interesting. Nevertheless, if you look at common story frameworks, you see it laid out when you watch a movie such as The Founder starring Michael Keaton as Ray Kroc.

Entrepreneurs and freelancers struggle. I recently watched a video by Sujan Patel who is one of the most well known digital marketers. Sujan laid out 12 struggles, or challenges, of being an entrepreneur.

See video here

Entrepreneurs such as WordPress professionals experience some of the same challenges as other entrepreneurs. The rewards, we often think, are worth the challenge.

Let me make this caveat before we start. For the sake of this article, I am using the term entrepreneur a little more generally to include both solopreneurs and freelancers. I know some see a difference between freelancers and solopreneurs, but for this article, we are all in the same camp.

I see an entrepreneur, in this article, as one who is self-employed and who may or may not have a team now or in the future. In many cases, a more traditional entrepreneur will build a company.

Six Struggles

Today, we will look at six struggles that WordPress entrepreneurs overcome to be successful. Obviously, these aren’t the only struggles. Far from it, but they are important issues we wrestle with each day.

Let’s begin, shall we?

Sustaining Energy

When we launch into our entrepreneurship careers, we feel a swell of energy and motivation. We are excited and ready to take the world by storm. However, we know it is hard to maintain that kind of excitement.

As Han-Gwon Lung explains,

When a business is new, it’s easy to feel optimistic and excited, but once you’ve been at it for a while, it can sometimes feel just like any other job. Jan Roos, founder of Expert Engines, a lead-generation company, related how he had to adjust to fading enthusiasm while still keeping up his energy levels.

Roos says,

“When you start out in a new business, you have all the optimism about how well things are going to work. But as I started to hear more and more objections, I started losing motivation and thinking that what I was doing wasn’t unique or valuable.

Sustaining Energy
Sustaining Energy


Have you heard of the Iceberg Theory of Success?  Steve Mueller explains,

. . . I’m the opinion that an iceberg can be an excellent metaphor for a successful person. Everyone of us can see the outcome of this persons actions and most of his accomplishments (= the visible part of the iceberg)1, whereas the efforts that were necessary to achieve such an outcome remain hidden, unnoticed (like the invisible part of an iceberg that is beneath the water line).

You see, we don’t see the hard work when we look at successful people. We don’t see the struggles, the adversity, and the persistence.

Remaining persistent is hard. Warren Webster says,

There will be times you will think to yourself, “This isn’t working.” You’re chasing that first big sale and hearing a lot of no’s. Investors aren’t signing on. The product is on its fourth iteration and still needs work.

These are the moments of truth. Every successful entrepreneur I’ve ever met has said, without question, that pushing through these times—sometimes for years—is what ultimately led them to a big win.


One of the most significant drawbacks of freelancing is the loneliness that is easy to feel when working alone. Often, introverts are freelancers magnifying the issue. Freelancers and entrepreneurs have to fight to overcome working alone or feeling as if they are alone because others do not understand the vision in which they have.

Sandra Haurant highlights this and the issues for freelancers in an article at The Guardian

Isolation, financial pressures, irregular hours and an inability to switch off can have a real impact when not managed properly, says Cary Cooper, professor of organisational psychology and health at MBS Manchester University. “For self-employed people, it’s a real problem. It can lead to the common mental health disorders – stress, depression and anxiety.”

It is up to us to take care of ourselves and manage our own personal self-care. As Jack Dempsey says in an article on Double Your Freelancing,

Just as managing the business is your responsibility, so is managing your happiness. If you can mitigate the tough times, grow in the good times, and remember to take a moment now and then to enjoy yourself, you can create the right blend of stability and security that leads to a happy freelancing life.

Generating Leads

Talk to any entrepreneur or freelancer, and one of the top issues of struggle is generating leads. If you are going to stay in business, you have to generate and convert leads into customers.

Getting clients, and leads is such a big issue that James Rose penned a post on the topic at the Content Snare blog.

There are as many ways to finding clients as there are answers. Each person may use a different way that works for them. As Ben Burns says on Medium, there is no silver bullet,

There isn’t any ONE proven way to find bigger clients. Finding high-paying design clients, as in any other sale, is all about people. Brainstorm and follow a customer/consumer journey, and make every effort to genuinely connect with other humans who are positioned to help you grow.

It is, ultimately about relationships. How you do that is up to you, but in this day and time, there are more efficient ways using digital marketing efforts.

Setting prices

Setting Prices
Setting Prices

Probably a close second to finding leads for freelancers is pricing. We regularly walk the line of pricing enough to survive, and low enough to get business. It takes a tremendous amount of courage to charge more.

You will have to decide how you set your rates. Are you charging per hour, or per project? Do you use value based-pricing?  On what do you base your rates?

These are all questions we ask when we get started.  This is where you have to dig in and study what others do and understand the market in which you are pitching your services. It’s not easy, and you will tweak regularly. Don’t give up. Remember, persistence.

Resources for setting rates:

Pricing 101 – How To Price Yourself As A Freelancer

Calculating Your Freelance Hourly Rate [infographic]

Not Sure What To Charge? How To Calculate Your Rate As A Freelance Web Designer

The Challenges Of Pricing And Selling With WordPress – Part 1

The Challenges Of Pricing And Selling With WordPress – Part 2


Discouragement comes in different forms, and we all struggle with that feeling. Frankly, you can look at the previous five points and see where discouragement comes. It is good to know that discouragement is not unique to your or me.

The key is to find a way beyond discouragement.

Freelance artist Meera Lee Patel said in an interview with Freelance Wisdom,

. . . The path was rocky, and I wouldn’t have been able to make it this far without stubborn determination, tunnel vision, and the support of my friends and family, who always (always!) encouraged me, even when I felt the discouragement deep in my bones. . .

Wow, “. . . discouragement deep in my bones. . .” Does that sound like you? Connecting with other WordPress solopreneurs can go a long way in alleviating discouragement.

Over to You

Sustaining energy, discouragement, setting our prices, generating leads and, ultimately, clients, loneliness, and persistence are six important struggles that WordPress entrepreneurs struggle with on a regular basis. We have to work hard to overcome these challenges.

What are some of the ways you overcome these struggles?

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Todd Jones
Along with being the resident writer for MainWP and content hacker at Copyflight, I specialize in writing about startups, entrepreneurs, social media, WordPress and inbound marketing topics.
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