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Want To Get Started Freelancing? This Guide Is All You Need

The modern work environment has never been in a bigger state of flux than it is right now. The COVID-19 pandemic pulled back the proverbial curtain on a huge societal myth. This myth was that employees need to spend 5 days a week from 9am to 5pm sitting in an office. As it turns out, the majority of corporate roles can be performed at least partially remotely. Moving forward, companies will likely continue to adopt a style of remote (or at least hybrid) work. In other words, it’s a great time to consider freelancing.

This guide will break down the following topics:

Section 1: The Pros And Cons Of Freelancing

Section 2: How To Get Started

Section 3: Landing Your First Gig

Section 4: Expanding Your Business

About the author:

Teddy Stavetski got started freelance writing in 2019 just before the COVID-19 pandemic. He started writing about personal finance (a personal passion) on and received 175+ 5-star reviews in his first year. Since then, he has worked with dozens of companies including InvestmentU, Academic Partnerships,, Advertisemint, Concreit, Treasure Financial, SelectFew, and more. His articles have been picked up by outlets like,, and Stock Trend Alerts. Teddy has now been freelance writing about business and finance for 4 years while living in San Diego, CA. 

Keep in mind that the tips and strategies below will not be a foolproof strategy that’s guaranteed to work for everyone. These are just the strategies that worked successfully for me.  

Section 1: The Pros And Cons Of Freelancing

Do you really want to be a freelancer? Let’s talk pros and cons

The life of a freelancer can often get romanticized. Self-Improvement Twitter Gurus love posting threads about how they earned $10K in their first month freelancing while sipping margaritas on a beach in Thailand. That’s not what this guide is. Like most things in life, it’s rarely ever that easy.

A career as a freelancer definitely has plenty of perks. But, it also offers a range of challenges that full-time employees don’t have to deal with. 

Here are the main pros of freelancing:

  1. Control over your time – This is the biggest selling point. As a freelancer, you can almost always work wherever and whenever you want. Want to cram everything on Monday to get ahead? Go for it. Want to fly to Europe and work from a coffee shop in Italy? No one can tell you that you can’t! 
  1. Control over your income – As a freelancer, you will likely end up working with several different clients (instead of just one main employer). In this sense, it’s up to you to decide how much you want to earn. Want to make more money? Just land more clients. Want more free time? Just drop clients. You also have the freedom to set your own rates as well as income diversification. In other words, your income is spread out over a few different clients, which is objectively safer than relying on one source of income.
  1. Control over where you work – Unless a client has an office close by then you’re most likely going to be working remotely the bulk of the time. You can work from home, in a co-working space, with friends, or wherever you want.

Of course, all this freedom and control comes at a cost.

Here are the main cons of freelancing:

  1. Income risk – When you jump into freelancing, you’ll have to say goodbye to the steady, reliable, bi-weekly paycheck. Freelancing roles are usually much more casual than full-time roles. You could be let go at any point with little warning. It also means that you have to be on top of invoicing clients, collecting payments, and chasing down anyone who doesn’t pay. In other words, your income will be fairly irregular.
  1. Sales – To be a successful freelancer you’ll need to get comfortable with sales. This is because you’ll constantly be selling yourself and your skills. Part of this process includes reaching out to clients, interviewing, negotiating a working agreement, and negotiating your rate.
  1. There’s no instruction manual: With the exception of self-help blog posts like this one, nobody is going to tell you what to do. You don’t have a manager to get advice from and every decision is yours to make. For some personality types, this is a breath of fresh air. But, for others, this can be overwhelmingly stressful. 
  1. There are no company benefits: Since you’re no longer a full-time employee you can kiss healthcare benefits, 401(k) match, an office, consistent coworkers, PTO, on-tap office kombucha, and other benefits goodbye.

If you’re still certain that this is the life for you then let’s examine the best ways to get started.

Find your lance

The origins of the word “freelance” date back to medieval times. In the middle ages, most knights would pledge their sword (or lance) to a specific king or nobleman. However, some knights chose to wander from kingdom to kingdom and sell their services to the highest bidder. These knights came to be known as “free lances” since they weren’t committed to any one kingdom. 

Today, freelancers sell services to different companies instead of their swords.

There are usually two types of people who want to get into freelancing. 

  • Person #1 – Someone who already knows what their lance is (AKA, the type of work they want to do. This person has probably been working in a specific industry for years. Now, it’s just a matter of making the jump. A good example is a Big 4 accountant who wants to open their own practice.
  • Person #2 – Someone who wants to start freelancing but has no idea where to start. This person wants to transition to freelancing but doesn’t know what services they’d offer or what their options are.

If you’re Person #1 then feel free to skip the next section. For Person #2 then let’s examine a few ways to generate freelance ideas.

Section 2: How To Get Started

Generating freelance ideas

Let’s start by saying that you’d be shocked at all of the different things that people will pay money for. Prior to getting started, I had no idea that companies paid people to write blog articles. I didn’t know what content marketing was and had never even thought about how writing on the internet had gotten there. 

I quickly learned that, in addition to blog articles, companies are eager and willing to pay for other forms of writing like:

  1. Website content
  2. Social media posts
  3. Social media captions
  4. Scripts for YouTube videos
  5. Advertising copy
  6. Newsletters
  7. Product reviews
  8. Presentations

This created dozens of different ways to monetize one skill: writing. The same holds true for any number of skills like graphic design, digital advertising, video production, programming, etc. 

The best way to brainstorm ideas that might be a good fit is to visit Fiverr’s main web page (Fiverr is one of two popular freelancing sites). On Fiverr, you can see all of the different services that freelancers are offering:

Be prepared because there are over 100 subcategories:

Like I said earlier…you’d be surprised at the number of different things people will pay you for. 

Spend a few hours (or even days) going through these categories searching for skills that might be a good fit. Ideally, you want to pick a skill that you’re

A.) Interested in

B.) Experienced in

C.) Talented in

You should pick a skill that checks off at least two of these boxes. 

But I don’t have any experience!

As mentioned, some people might have years of experience working in a specific industry before making the jump to freelancing. For them, they’re experts at what they do and know how the industry works. But, for newbies, jumping into a freelance gig can be intimidating, especially if you don’t have any experience.

One way to think of it is that you’re jumping into an Entry Level Freelance role. You expect to learn on the job and are willing to accept a smaller salary. In this sense, it’s not that much different than a corporate entry-level job.

One of the best ways to overcome this feeling that “you don’t have any experience” is to create your own experience. This is what my journey looked like step-by-step:

  1. I discovered that I could make $30+ for writing blog articles about personal finance. Personal finance was a passion of mine and I had already spent several years self-educating on the topic. I was fairly confident that I had what it takes. But, I had no experience…
  1. So, I created my own blog. I used WordPress and started just churning out blog articles on topics I was interested in. Then, I listed my blog on my Fiverr profile.
  1. Lots of interested clients would read my blog and reach out to hire me. Many of them even requested similar articles to what I was writing on my blog. The ironic part was that, at the time, my blog probably only got about 5 hits a day (and most of these hits were just me from my phone). But clients didn’t know that. They just saw my blog and liked my writing. 

Creating your own online portfolio is a great idea for most services. It puts your work out there and lets people know what you’re offering. Here are a few more ways you can create your own experience:

  • Education – List relevant degrees, majors, or courses that you’ve taken. If you don’t already have relevant education then you can always take an online course in your preferred subject.
  • Licenses – Some services might require certain accreditations, licenses, or certifications. Getting these will present you as an expert in that topic.
  • Clubs: Join relevant groups, clubs, or organizations related to your service. Facebook Groups is a good place to start. This helps you network with others in your industry.
  • Do work for free – Reach out to friends, family, coworkers, or other connections and offer to do freelance work for free. Then, list this work experience on your LinkedIn, Fiverr/Upwork, and personal website.

Remember that it’s all about building up your resume over time. Unless you have previous experience, it’s going to take time to get the ball rolling.

So, once you’ve settled on a service that you want to offer, what do you do next?

Section 3: Landing Your First Gig

Freelancing sites like Fiverr and Upwork are the easiest place to land your first gig. In general, these sites have bad reputations for being full of scams, lowballers, and low-quality work. However, that hasn’t been my experience at all. Here’s my breakdown of both sites…


Fiverr is a good place to meet a lot of potential clients. There are also low barriers to getting started. You just need to create a seller account, build your profile, and create a “Gig” around the service you are offering. Once your gig is live, Fiverr’s visitors can see it and hire you. 

I’m not going to go in-depth on building a Fiverr profile since that would easily require its own guide. 

There are two just main problems with starting on Fiverr:

  1. It’s reactive – You create a gig and then have to wait for people to reach out. If no one reaches out then you don’t make any money. For newer accounts with no reviews, it can be very slow to gain traction.
  1. It’s crowded – There is a lot of competition for most categories which can make it difficult to get started. My best advice if you are just getting started is to pick a specific niche that’s less crowded than general topics. For example, when I started I created a gig for “Personal Finance Blogs” as opposed to just “Blog Writing”. Another idea is to create a gig in one of Fiverr’s New categories.


Upwork is very similar to Fiverr but with one big difference. On Fiverr, you create a gig and then let employers reach out to you. On Upwork, employers create a job posting, and then you can apply to work with them. Since you can actively apply to jobs on Upwork, it is a better platform to get started on. You can also tailor each application to make it more personable.

Again, I won’t go in-depth here on creating the perfect Upwork profile.

Freelancing sites: Final takeaways

It’s definitely worth creating a profile on both sites. Although it may be slow to get started, both sites are great for introducing you to a number of different clients. At my peak, I would get 4-5 new requests per day for different projects. 

Some of these were one-off projects but many of them turned into long-term gigs. This allowed me to get a lot of experience in a short period of time. 

Additionally, both platforms have a rating system that allows you to get valuable feedback from clients. If your ratings are good then you know you’re on the right track. If your ratings are generally bad then you’ll learn how you can improve your service.

Creating a profile on these sites is a little bit like small business owners listing their products on Amazon. Doing this instantly gives the small business owner access to Amazon’s massive audience. But, with that said, being 100% reliant on Amazon to sell your product is risky. The second that Amazon decides to delist your product, your income is cut off. 

The same goes for Fiverr/Upwork. Creating a profile instantly gives you access to a large marketplace of employers looking for freelancers. But, building a long-term career on either platform is a little risky. Let’s take a closer look at that and discuss expanding beyond Upwork/Fiverr.

Section 4: Expanding Your Business

As great as Fiverr/Upwork are, building a career on either platform is unsustainable. To start, it’s risky to base all of your income on these platforms because they can delist your profile at any moment if they want to. Additionally, they both take about 20% of all your earnings. This takes a serious dent out of your take-home pay. The more you earn, the more your pay.

So, once you’ve landed a few clients and have the wheels turning, what are some ways that you can expand your business?

1.) DON’T move off Fiverr/Upwork – Chatting with customers outside of either platform is not allowed by Fiverr/Upwork’s regulations. That’s why I would NEVER recommend that you ask clients to email you separately in order to save money on platform fees.

2.) Work upriver – In the beginning, you’ll probably be forced to work for less-than-ideal pay. But, assuming you do good work, you should be able to build up a consistent client base. Once you’ve reached your bandwidth limit then you can start to raise your prices.

I personally hate raising prices on existing clients (unless we’ve been working together for over a year in which case I feel justified in making a slight price increase). Instead, I just quote new customers with a higher price. Then, as time goes on, you can slowly swap out lower-paying clients for higher-paying ones.

NOTE: Price is not the only factor to consider when accepting a new client. You also want clients that are easy to work with, pay on time, and offer exciting work. I’ll definitely consider working for a lower rate if I know that a client is easy to work with and pays on time. On the other hand, sometimes a higher rate isn’t worth the headache that accompanies working with certain clients. 

Other strategies to expand your business

Focus on existing relationships. After you’ve worked with a client for a while, do some research to see if there are any ways that you could offer additional value. If you can accept more responsibilities then you’ll be justified in asking for a higher rate.

Referrals, referrals, referrals. Collect referrals from clients early and often. This is by far the best (and easiest) way to grow your business.

Cold outreach. Find companies that would benefit from your services, find the person in charge of what you’re offering, and send them a personalized email. Offer advice, ideas, and any strategies you can think of.

Create a website. If you don’t have one already, post a website that highlights your skills. This makes it easy for clients to find you and review your work.

There you have it! I hope that you’ve enjoyed this guide to starting a career as a freelancer. Keep in mind that everyone’s journey will look a little bit different. The most important thing is to keep working and making consistent forward progress.

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