Taking a hammer out of a tool box

Demo this! Business tools and resources for entrepreneurs to run their freelance business like a real business

14 min read
Mike Demo

The imposter syndrome is strong among WordPress freelancers. We get it, but keep repeating to yourself: “Freelancing is a real business. Freelancing is a real business.” Being a real business is a mindset. So, to feel like your freelance business is a real business and not just a hobby, you have to operate like a real business.

Do you have clients? Do they pay you money for the services you provide? Are you paying taxes? That sounds like a real business! In 2023, the idea that you need a storefront to be a business is yesterday’s thinking. With your laptop, good Wi-Fi, and your ideas, you’re a business that can move mountains.

It’s pretty cool working from your living room, an airport, or a client’s office. And it’s great to be your own boss! Since the COVID-19 pandemic, even large companies have seen how practical it is to have a workforce of agile self-starters who can work from anywhere.

There are currently almost 60 million freelancers in the U.S. alone, poised to become the largest workforce by 2027. Even Google currently employs more freelancers than it does full-time staff.

Solo entrepreneurs, this is your time!

Freelancers: Dress for the job you want to have

You’ve heard the expression, “Dress for the job you want.” Many freelancers enjoy working in a — shall we say — less formal business environment. But if you want to improve your image as a freelancer to a small business owner, then dress for the job you want: the account.

Changing into your work uniform affects your mindset, which affects how you run your business.

Sure, there are flaws to the idea that you should focus on where you want to be rather than where you are. But there’s something to be said for not managing your business in your pajamas like a front-yard lemonade stand on movie night.

Are you a business, though? You pay yourself a salary, so you have employees. You pay bills for internet, electricity, and probably a workspace, so you have overhead expenses. You probably even have a logo and corporate colors. It sounds more and more like you’re a business and not just a freelancer.

So how are you running your freelance business?

Managing your freelance business means managing yourself

Businesses are run by people. In many countries, corporations have the same rights as people. They might not be flesh and blood, but companies are viewed much like people are. Think about the last time you went into a new store for the first time. Now think about when you went on a blind date.

First impressions, trust, expectations, obsessions — everything we experience with other people, we experience with companies and their brands.

Time, work, communication, money, productivity, and accountability are integral to a successful business. Managing your business isn’t complicated – just manage it the same way you manage yourself. You do manage yourself, right?

Managing your freelance business means managing your time

Time management is self-management. Most of us don’t use our time properly. Another way of looking at this is it’s not that we have too little time, we have too much we don’t use! The problem isn’t about managing time but our work method.

Managing your freelance business means managing your way of working

Good self-organization helps us structure our daily work routine. If you want to end the day with a clean slate, you need to be productive. The hardest thing we do as freelancers is try to get everything done alone, as opposed to outsourcing some of the work; some even neglect important business tasks like invoicing and taxes. We must learn to dare to say “no” and focus on what we’re good at. That’s often hard. Ask for help. Outsource tasks.

Managing your freelance business means managing your communication skills

Communication skills are one of the first things we learn as a child. Body language, speaking in complete sentences, and looking at people when we talk to them all show respect in communication. Today we’re communicating less in person and more over screens and our phones, so look at the camera. That’s the closest thing to eye contact many of us have with our clients. Our verbal skills, post-meeting follow-up, and mindfulness of context are other layers of successful communication.

Managing your freelance business means managing your finances

It’s exciting being your own boss. All the money that comes in is yours – well, you think it is anyway. No more bosses, no more accounts department. But are you charging enough? At the end of the day, your $120 website development hourly fee shrinks quite a bit after you factor in bills and taxes.

“In the WordPress Community, we talk about value — quite a lot. And that’s awesome. We should charge for our value. The problem comes when we don’t understand our cost — both in financial, physical, and branding terms.”
Bridget Willard

Is there enough for a daily coffee to go? What about the upgrade to your laptop? Are cat toys a tax deduction?

Managing your freelance business means managing your productivity

Productivity is measured by dividing results through effort. And today, our generation has it so good! We can work around the globe and use the tools in the cloud to work while doing something else.

The temptation is to use all the latest tools, but is that the best idea? Remember, each tool must be managed. Do you have the time? The tool that works the best is the one you use. Commit to a business tool stack, and you’ll find your flow in no time.

Tools and resources to help run your freelance business

Think of your freelance business stack like a capsule wardrobe. With the right six items, you can create thirteen outfits for the office. Mix and match to make your stack. Think of reliable and timeless pieces (free tools), and use your extra budget for accessories (paid tools).

The corner bookstore had more than 70,000 “help for businesses” titles in its catalog – and that’s just the books. Add to that the countless online tools, courses, coaching whitepapers, and advice from your Uncle Larry, who spent 30 years selling raincoats.

Support – because solopreneurs can’t do it all alone

With the number of tools and resources available to freelancers, the first thing you’ll need to focus on is your time management skills! The following list is by no means exhaustive, but we think it will get you going in the right direction.

Freelancers Union

Freelancers Union represents and advocates for the interests of independent workers in the U.S., promoting fair treatment of freelancers to foster a more supportive environment for independent work. The organization offer a variety of services and benefits:

  • Discounts
  • Freelance toolbox
  • Financial tools
  • Insurance
  • Contract creator

Membership is open to anyone who is self-employed, including gig workers, independent contractors, and of course, freelancers. Membership is free but applies only to those working in the US.


IndeCollective is a community and platform for independent professionals, freelancers, and solopreneurs. It offers a range of services and benefits, including access to educational content, business tools, and a community of like-minded professionals.

Members can participate in events, workshops, and other networking opportunities. Membership is open to independent professionals of all types.

The regular annual membership fee is $6,995, but IndeCollective offers scholarship discounts for its members.

Cockerell Academy

Lee Cockerell, retired executive vice president of Walt Disney World, is the creator of the Cockerell Academy. This online school offers courses in leadership, management, and business culture. The skills you learn here will help you manage your business and customer service. Courses are based on case studies from Hilton, Marriott, and Disney.

The annual subscription fee, which includes all courses, is $400, but the school offers a free planner on its home page.

Project and time management tools


Don’t like Mondays? This is a better kind of Monday! Monday.com is a project management and team collaboration platform. It helps you plan, organize, and track your work. Its range of features include task management, project planning, time tracking, and team communication tools like the following:

  • Work Management Tool
  • Sales CRM Software
  • Product Management Software
  • Marketing and Creative Manager
  • PMO Collaboration Tool

The platform is customizable, so you can use it as works best for you. It’s cloud-based, so you can access it anywhere. Access is free for individuals. If you need to work in a team, the monthly fee ranges from $24 to $48 depending on the software features you require.


Trello is one of the best-known project management and team collaboration tools. It uses a system of boards, lists, and cards to help teams manage tasks, projects, and ideas.

Trello is known for its intuitive and simple UI. You can plan, organize, and track your work in the cloud from anywhere. Access is free for individuals. The monthly fees for teamwork range from $5 to $17.50, depending on your required features.


Trello’s best-known competitor is Asana. Asana is famous for its powerful features and integrations with other tools, making it a popular choice for teams looking to streamline their workflows and increase productivity.

Access is free for individuals. There are two monthly rates, depending on your needs: $10.99 or $24.99. The Premium fee includes integration with Salesforce, Adobe Creative Cloud, Tableau, and Power BI.

Tools to keep more money in your pocket


This is not the well-known birdwatching board game. Wingspan is an online payroll platform for independent contractors. This tool can make instant payments, saving you time and money.

You can invite contractors to join your network, requiring them to complete onboarding questions. You can upload W-9 forms and enable secure payments domestically and internationally. Isn’t that a relief?

Wingspan is free for contractors – which is pretty amazing. The monthly flat fee of $500 for teams or $1,000 for companies makes it a highly affordable payroll solution. For contractors, the service offers a free Wingspan debit card and free business banking. Where else can you get that? And your contractors don’t have to be shut out from health benefits since Wingspan offers significant discounts on those plans as well as free invoicing for its clients and more.


Eventually, all that money you make needs to be taxed. That can be a major headache, but Keeper makes it easier. In addition to regular business expenses, this tool will help you find deductions just for freelancers.

Keeper’s platform uses AI to help you accurately and efficiently file your taxes. The platform has a great UI, offers a mobile app, and has a range of services, including tax preparation, planning, and resolution. There is a flat rate of $99 for a simple tax return or $168 for a return with business income.


The problem with many contracts can be the legalese. You just want a contract written in simple English that each person signing can understand, right? Enter MonsterContracts.

This contract creation service was written specifically to cover “normal” website creation and management; however, the template can be tweaked. The MonsterContracts website states, “If you offer SEO and Social Media services, you can easily add your existing terms to the MonsterContracts™ template.”

MonsterContracts is accessible at an annual membership fee of $39. The fee for the first year is $199.


Let’s say a client balks on your contract. What do you do? Right, you’ll need legal help. LegalShield offers “legal advice and representation for pretty much anything” at attractive prices.

With a LegalShield plan, you can receive legal advice and representation for a wide range of personal and business legal issues, including reviewing contracts and representation in court. LegalShield operates in the U.S. and Canada. Rocket Lawyer supports the U.K., Spain, France, the Netherlands, and Brazil.

LegalShield’s fee structure begins at $24.95 a month for individuals and goes to $149 monthly for businesses. Additional services are also available.

Books for Downtime

Freelancers are busy people. You’re juggling a dozen things. So, what should you read each day, and more importantly, when?!

Daily reading has a positive impact on the content that you publish on your blog, podcast, YouTube, or social media channels, just as an example.

Reading for even 30 minutes a day empowers you. This isn’t a tip because it will strengthen your expertise or broaden your range of topics either. Reading allows you to inspire others with the knowledge you obtain, and it forms new connections in your brain. Neuroplasticity for the win!

Dealing with Problem Clients: Fencing in the Friendly Monsters by Nathan Ingram

This book is for web developers working with clients. As we all know, a single bad client can wreak emotional havoc on the rest of our day. The first part of this book is fiction, a series of four stories about relatable WordPress freelancers who encounter clients who cause trouble in their lives and businesses. The second part explains the essential systems and structures your business must have to keep problem clients contained.

Time Management Magic by Lee Cockerell

During Lee Cockerell's career as the Senior Operating Executive of Walt Disney World Resort, he operated 20 resort hotels, four theme parks, two water parks, and the ESPN Sports Complex. The time management secrets he developed there have become one of his most requested corporate training lectures and are now available to you in this book.

Smart Brevity by Axios

Stop wasting your reader’s time. This book Smart Brevity: The Power of Saying More with Less, can help. The founders of Axios and Politico share their methods for punching through the noise to get people to pay attention to what matters most in this book.

Run your freelance business – don’t let it run you

Meet Alex. They’re your average Freelancer. Running a business, just like you. Time is their most valuable commodity, followed by a balanced budget. The tools they use help them be more productive and efficient. After all, time is money, but it’s the one thing we can’t purchase. Alex needs a good collection of tools at a reasonable price.

Alex chooses Trello for project management. It helps them inexpensively organize tasks and projects, communicate with clients and team members, and track project progress.

It also helps track the time spent on projects, which can be useful for billing purposes and identifying areas where they can improve efficiency.

Alex works with clients and team members remotely, so communication and collaboration are gold. Trello helps Alex stay connected and collaborate effectively, too.

Wingspan’s invoicing and payment software helps Alex prepay their team and ensure they are paid on time. It assists with creating and sending invoices, as well as managing Alex’s finances and payment processes. Keeper takes care of the boys and girls at the tax office, and LegalShield reviews any contracts before they go out for signing.

Alex’s website attracts the next round of clients even while busy with current projects. Creating an online portfolio can help Alex showcase their work. Many platforms are available, but WordPress is one of the easiest content management systems to learn – and it’s free.

Alex doesn't have the time to create a professional-looking portfolio but is interested in managing the site when it’s ready. WordPress is pretty easy in that regard. Thank goodness for the folks at Codeable. Codeable helps freelancers of all shapes and sizes grow their freelance business without the pain of growing their solo team.

How will you kick your freelance business up a notch this year?

As a freelancer, it often might seem that you’re alone, but that’s last year’s thinking. Remember, if you ever get stuck, all the great folks of the GoDaddy Pro community have your back! Simply resolve to use all the free tools that save you time managing your website, clients, and projects. That’s a lot of resolutions already checked!

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