How To Start A Successful Freelance Business And Actually Get Your First Paying Client [Part 1 of 6]

If you have been messing around trying to start a freelance business, thinking of leaving your unhappy corporate job or looking for an avenue to bring in a thousand extra dollars per month (or even tens of thousands per month) then this guide is everything you need and have been looking for.

Your freelance “precious.”

It’s my best attempt at a NO B.S. action plan to create something epic for yourself from ZERO. Nada. Scratch.

…….A plan to actually learn how to start a successful freelancing business.

I have wanted to share my honest thoughts on how you can start a successful freelance business for some time now.  This post has been in the works for a while and I hope it is a great resource for the journey you’re about to embark on.

I call this the “Freelance Hustler Process”

A simple process that I personally used to launch a multiple 6 figure+ business (Gingerbread Marketing) in less than 18 months alongside my business partner Tommy.  You can read more about our origin story here.

$300,000+ later…..we have learned a few things.

This process is something I have swiped from the most successful minds in my circle of influence.  Something that is continually being improved upon.

Learn. Apply. Teach. Do.  Repeat.

Freelance Hustler Learn, Do and Teach

I have broken this guide into 6 parts that are set to be released over the next few weeks.  My goal is to pass as much wisdom to you as possible from my journey to yours and to help you skip past some of the mistakes that I have already made for you 🙂

Like Charlie Munger said, “Everyone learns from mistakes. But that doesn’t mean they have to be your mistakes.”

Warren Buffett and Charlie Munger credit their success to learning how to mitigate risk.  A powerful skill.  The best way to do that is learn from others who are years ahead of you.  Mentors, Coaches and Mastermind groups are the key here.  This is something that is lacking within the world of freelancing.

Click Here to Start your Freelance Journey Today: Learn about the 5 freelancing tasks that even beginners can have success with on Upwork.

Simulating successful people is rarely talked about.  Instead you your hear, “Get out there and fail, that is how you learn.”

I think that’s horrible advice and I’ll fill you in more on why I think so later…

The past two years of my journey have been incredible.  I have felt like Kurt Douglas in the classic movie; Romancing the Stone.  I have embarked in danger, romance and adventure throughout the jungles of Colombia.  I haven’t swung from jungle vines or discovered rare valuable diamonds yet, but I have come across something I would deem more valuable…

A process on re-defining and selling yourself as a freelancer.

Romancing the Stone sparked my Freelance Travels to ColombiaRomancing the Stone (mentioned above) was the film that originally inspired me to travel to Colombia back in 2012.

I have a deep love for the country of Colombia now.  My journey of getting uncomfortable started there.

Traveling to a foreign land.

Learning to speak spanish.

Salsa dancing with Miss Colombia.

Picking coffee beans from local farms deep in the jungles and mountains of Colombia.

It is amazing how rewarding getting uncomfortable can be.  This is now my challenge to you.  To succeed as a freelancer you have to overcome many obstacles and being “uncomfortable” is one of them.

It is fitting because Colombia is actually the birthplace of my freelance business.  Just myself, a cafe americano, a laptop and a whole lot of hustle.  This is where it all started, 2 short years ago…

…multiple six figures later, here we are.

Throughout this series I will share more of my story.  But first I want to kick this off with some questions that I continue to receive as I work with more and more freelancers within our mastermind group.

First, why do so many freelancers fail?

Why do so many freelancers struggle to properly sell themselves?

Why do so many freelancers fail to value their offerings?

As a freelancer, rarely do you have a “skill” problem but rather a “sales and marketing” problem.

This is what I want to empower and help freelancers with.

Starting a freelance business has a perceived feeling of being extremely hard and or challenging.  To be honest, it definitely can be without the right framework.  Over the past two years, I have not only started a successful freelance business but I have helped lots of others do the same.

This website (Freelance Hustler) and our recently released 3 Day Make Money on Upwork Mini-Course, Freelance Challenge & Inner Circle Community are here to empower and support freelancers on their individual journeys.  These are just some of the resources we are creating and will release in the upcoming months. For now the best place to start is our Upwork Starter Kit.

Click Here to Start your Freelance Journey Today: Learn about the 5 freelancing tasks that even beginners can have success with on Upwork.

We are in the process of creating the #1 resource for freelancers in the world.  A truly elite community.

I have been speaking with freelancers from all industries.  Web design, consultants, graphic designers, copywriters, admins, assistants, programmers, etc.  I have noticed a lot of sticking points that resonated with me when I first started.

As well, I have been able to identify and match a ton of common limiting beliefs that are holding most freelancers back.  More than likely these are holding you back as well right now.  Getting past these are huge and a lot of our resources will focus on helping you overcome these hurdles.

Freelancing, consulting and or a “service” type of value offering is one of the easiest and quickest ways to start an online business.  If you are new or transitioning into freelancing this is great news.

One of the quickest way from an unhappy life ————> to living somewhere amazing and working from your laptop = Freelancing.  You have the ability to leverage skills, learn new skills, and create a lifestyle business from your laptop starting today.

Freelancing here in Medellin Colombia Views from my Balcony by Freelance Hustler
Freelancing here in Medellin, Colombia –views from my Balcony 🙂

On the flip side, freelancing can be a very challenging type of business to sustain for a long period of time if you fail to adjust correctly.

But let’s not focus on future problems until they arise.

In this article I want to show you a framework that you can use starting today to either start a new freelance business or launch a new service offering successfully to your clients.  This for me is a NO B.S guide that I hope will motivate you to stop kicking tires and take action- TODAY!

Move your freelance business forward!

Burn the damn ships.  Let’s do this thing!

For me it was moving to a foreign country.  Put yourself in a position where your only option is to succeed as a freelancer.  Otherwise, you will undoubtedly fall back to plan B.  Listen…plan B sucks.

Right now, I’m sitting here in the beautiful city of Barcelona, Spain.  I have been here the past month running one of our-yearly marketing retreats where we work with new online freelancers directly to get their businesses off the ground.

Barcelona is a truly incredible city!  Surrounded by art, spanish guitar and tapas.  Can you really go wrong?  All this fueling, in my best hopes some great content that will help make you smile and kick some freelance ass.

First what truly defines a freelance business?

I would argue that it is uber simple.  The answer…a paying customer.  A simple metric that defines any business.

So let’s get your freelance business cranking and get you a paying customer.

Below I have put together an outline of our personal “Freelance Hustler Process.”  I will breakdown each of the sections below in detail during the upcoming weeks.


Section 1:  Unveiling your strengths and picking the sharp sword- defining your industry and skill sets.

Section 2:  Exposing your mind hurdles and removing all limiting beliefs.

Section 3:  The long lost business superpower – idea discovery within your marketplace and Identifying client problems.

Section 4:  The power of solving problems – how to create solutions around real problems.

Section 5:  Offering that solution to your marketplace and validating by selling, collecting money and getting clients.

Section 6:  Finding who has your needle- identifying where your ideal customers are or who has access to them.  Your “Freelance Dream 100.”

Unveiling your Super Strengths and picking the sharp sword

Section 1:  Unveiling Your Super Strengths and Picking the Sharp Sword- (Defining your Industry and Skill Sets)

We are all incredible at something.

If you don’t think so you can do the “stranger exercise.”

Simply ask your friends and strangers (new acquaintances) what they think you are great at.  Acquaintances often offer the most beneficial feedback.

A skillset will arise from the darkness I assure you.  Take that and grab it.  More than likely you have something in mind or have been trying to get traction with some type of freelance service offering already.

My goal here is to just really help you outline your core skillsets so we can anchor to it moving forward to an actual offering.

Here I want to define what your strengths are and what direction you could go with your service offerings. This starting point is a really fun exercise to revisit your skill sets and circle back to your core strengths.

Let’s get it going.

Step A:  Discovering your Skills

Let’s start with writing down your skillsets. Below is a great list of questions to get some ideas flowing:

What are your core strengths?

What do you think you are really great at?

What do people say you are good at?

Are you an exceptional writer?

Can you build incredible websites?

Are you amazing at selling?

Do you have a knack for managing people?

Can you build amazing sand castles?

Really think what is easy for you but is challenging and difficult for others?

Action: Less is more. This may be challenging and you may have many things but really narrow it down and pick that number one thing that trumps all others.

Maybe this looks like: writing copy, designing landing pages, managing teams, selling, etc. (Pick one and Continue to Step B)

Click Here to Start your Freelance Journey Today: Learn about the 5 freelancing tasks that even beginners can have success with on Upwork.

Step B: Idea Mapping Your Service Offerings

What could you potentially offer to clients?

What have you been paid for in the past?

If you haven’t yet been paid don’t worry.  Step C (below) will unveil the curtains of what you could potentially offer to your niche client base.  Here I just want you to list out as many ideas of what you could offer.  Think of things that are top of mind that fit with your main skill you have listed in Step A.


If you are a copywriter you could offer VSL’s (video sales scripts), blog posts, reviews on products, sales letters, landing pages, email copy, ebooks, guides, etc.

If you are a web designer you could offer membership websites, wordpress sites, landing pages, sales page design, tech support, etc.

Action: What are 10 things you could sell around your main skill set?

Step C: How to Listen Online

Look at what people need right now to draft your own service offerings

This is the first step in really seeing what is possible online.

Above you have defined your core strengths and have listed out some ideas of what you could actually offer. Next, is to do some recon and actually look online to see what people are needing within your industry.

What problems are they posting?

What job ads are currently being ran by people within your niche market looking to hire people like you?

This will be a great indicator of what you could offer.


Start by looking on freelance websites like:

Upwork, Elance, Fiverr, Freelancer,, Craigslist, etc. Anywhere where people are actively posting and looking to hire Freelancers online.

Type in your main Industry like “Copywriting” and see what jobs people currently need help with right now.

Freelance Hustler looking for jobs online with

Just from this example on just one freelance website ( image above) I’m able to see within the “writing” category there are currently 5,928 active jobs available.

Idea wise I have the following from just the first page:

  • Writing Landing page Copy
  • Ghosting writing articles
  • Writing Ebooks
  • Social Media Copywriting
  • Email Copywriting

Again these are things people need help with right now and are willing to pay for someone to do them, immediately.


The goal here is to list or bookmark in your browser 30 jobs that would require your main skill-set.  Take a sampling from a few different websites to see what people are looking for.

Do you see patterns of what people need help with?  Where are the pain points?

Are there multiple requests for the same type of job request?

How do these match up with your skill offerings?

Step D: Honing your Initial offering

You now should have a good idea of your “sharp sword” and a list of what the market needs from live job ads that you researched in the previous step. Now it is time to really hone in what your offering will be.

You want to take into account these 4 main things:

  • What do people want and need right now the most?
  • What are you most interested in?
  • What you are great at? Biggest skill that separates you.
  • Out of the options listed which one do you have the most experience with or know people in your circle who have experience with?


If your main skill set is copywriting and you discovered online through your research that Video Sales Letters were in high demand, mentioned often, posted multiple times and you love video production, then writing and telling stories via this medium would be not only a great fit within your skill sets, but also have demand within the market.

In the comments below please let me know what your sharp sword is and if this process was helpful or not. In the next post I’m going to go over exposing your mind hurdles and removing all limiting beliefs around moving forward with your sharp sword.

This is something that literally took me from low 5 to multiple 6 figures in less than a year.

Looking forward to hearing from you 😀


Click Here to Start your Freelance Journey Today: Learn about the 5 freelancing tasks that even beginners can have success with on Upwork.

I help talented Freelancers use Upwork to leverage explode their online careers, add a serious boost to their sales and develop their ideal dream lifestyle. All of the strategies and techniques that I teach to others are ones that I have used myself and things that I have learned from building my very own multiple six figure content marketing agency. Gingerbread Marketing.

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