Freelancing 101

I’ve worked remotely in some capacity since 2014, and I love it. There are many reasons why remote work is the best choice for the coaching life. When our kids were younger, it allowed me to contribute to our family’s household income without hiring a babysitter. Most of the time, I flexed my work hours around school and coaching. Now that our kids are older and more independent commuting to an office and working until 4 or 5 pm every Friday feels unnecessary and constricting. Remote work doesn’t always require that you work as an independent contractor. However, freelancing is the most common way to ensure you remain remote. I’m offering my perspective on remote work and what to consider before taking the leap in today’s freelancing 101 blog post.

Freelancers are Entrepreneurs

My venture into remote work was freelance writing. I quickly learned that I would need to figure out a few ways to get my work to stand out among the noise, or I’d spend more time hustling for work rather than writing. Even though I hadn’t started working for SMA Marketing yet, I realized that a basic understanding of marketing would improve my ROI and increase my writing opportunities.

In addition to marketing my skills and talents, I was also expected to negotiate deadlines, track payments, advocate for myself, and report my earnings to the IRS. Since most of my articles were purchased through a writing hub that paid per word, any time spent focused on freelancing other than writing was time I was not officially earning an income.

The second lesson I learned when freelancing is how true the phrase “you need to spend money to make money” can be when starting a business.

Freelancing is a great opportunity for entrepreneurs to design custom careers that align with their passions and skills. However, it’s also a lot of work, especially when someone first establishes themselves. Today we’re exploring why freelancing is a lot of work and a few ways to improve work and life balance.

Freelancing Looks Different by Industry

Not all freelancing is equal. Some employers prefer to reduce overhead costs by hiring remote staff for specialty areas. You may find that a company hires third-party workers for IT services, customer service, or website SEO. Third-party workers are independent contractors, even if they work strictly for one company.

Other companies hire specialists on a project-by-project basis. In these situations, you may have a great relationship with a business and find that work comes sporadically based on their ability to close deals that require your services. This second group of freelancers tends to find themselves balancing more individual clients.

Yes, Freelancing is Hard Work

When you launch a freelancing career in any field, you have a few challenges:

  1. You need to ethically market your business so people understand the products or services you provide, and you also need to ensure people can find you.
  2. You need to establish a competitive price point.
  3. You must ensure you have the proper tools, certifications, licenses, and/or training.
  4. You need to have a good system in place to provide proper estimates of time to complete work.

And this entire list is so that you can obtain work. Once you reach an agreement to complete a project, you’ll need to ensure you have a proper workspace to complete the project within the agreed upon timeline and a way to accept payment.

Traits of Great Freelancers


The best freelancers understand the importance of multitasking. To have a steady flow of work, you’ll need to continue marketing yourself while completing projects. Additionally, it’s helpful to look for new income streams. For example, sites like UpWork and Fiverr and becoming oversaturated, with over 12 million registered users on Upwork alone. This also means any way you can get your profile to stand out is helpful.

Establishing Boundaries

Freelancers need to hold regular office hours and know their limits. Taking every job that comes along is tempting, but when too many contracts overlap, a freelancer risks falling behind on deadlines or producing subpar work. It’s important to remember that customer reviews are the most important recommendations for companies. Additionally, you should offer your best work with every project.

Strong Communication

Freelancers are responsible for communicating for themselves, advocating on their behalf, and marketing for themselves. Clear communication is vital both with clients and business communications.


Freelancers will gain work through word of mouth. It’s important to network industry-wide to form business partnerships and expand your network of potential clients. Great partnerships will also help you gain credibility.

Strategies to Improve Freelancing Productivity

Even though freelancing is hard, that doesn’t mean it’s something to avoid. For some, it’s the only way to pursue their dream career. For example, if you’re married and your spouse’s career requires you to live in a specific location, your own opportunities for job advancement may be limited. Freelancing allows everyone to work in their preferred job field.

Working remotely requires discipline, which the tech world and office supply companies have spent a lot of money designing. There are even people who have built their entire careers around helping other people stay organized and improve productivity.

Task Management

Choose a system to track your tasks. This should have an option for collaboration. Asana, Trello, ClickUp, and Airtable are common systems people use. My system of choice is Airtable. It has both App and Desktop features, it syncs with Google Drive, free training is available, and it offers collaboration options.

I use Airtable and a paper task system to give me a broad week-by-week overview of all my clients.

Setting Goals and Staying Organized

Time Tracking and Invoicing

Many people choose to use a combination of free systems such as Toggl and PDF invoices. There’s nothing wrong with this; however, I’ve recently switched to My Hours, and it’s a really helpful system that keeps everything in one hub. Regardless of your choice for invoicing, you’ll need a consistent system that keeps a record so you have receipts come tax time.

Establishing Work Hours

I’ve already mentioned this, but creating work hours is important. It’s tempting when your office is down the hall to work late at night or over the weekend. While this may be necessary from time to time, it’s not the habit you want to establish for a healthy work/life balance. Consider a block calendar strategy.

Consider Hiring Help

Eventually, as your business grows, you’ll need additional support. Something to keep in mind is that you’ll want to hire someone whose strengths are in areas that are different than yours. Additionally, if there are things you can’t delegate, you should hire someone who can handle the things you can reassign.

Whether you’re a writer, web designer, bookkeeper, or consultant, freelancing is an excellent way to build a business and thrive in your sweet spot. It’s important to remember that freelancing is work, and every job has challenges.

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