My Roadmap To Start Freelancing

Last March I quit my traditional marketing job to become a full-time freelancer. Ever since I’ve fielded questions from people looking to embark on a similar path. It is by no means a career move for everyone; it takes a lot of ambition and grit to go it alone. But for anyone looking to make the jump, here are some applicable principles and concepts that have become the cornerstones of growing and sustaining my freelancing business. Though my experience is primarily in the field of digital marketing, these concepts can be applied to almost any freelancing business.

If you’re more of a video learner, here’s a link to the full chat.

I recommend the following roadmap:

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I started experimenting with various online platforms to build out the foundation of my freelancing business. There are a lot of platforms out there, however, for the sake of this article I’ll narrow them down to two major platforms: Upwork and Fiverr. They have easy to use built-in features that help you get started attracting potential clients immediately. Below I break down the major differences between the two.


  • You bid on job postings (you can also get invited to jobs by clients)
  • Every month you can bid to work on a limited number of job postings

Has a varied pay scale

  • 20% for the first $500 you earn with a client
  • 10% for total billings with a client between $500 — $10,000
  • 5% for total billings with a client that exceed $10,000

Choose UpWork if… you want to take a more active approach and bid for jobs that suit your preferences


  • You create your own job postings
  • Clients view your job postings and respond if they’re interested

Has a set pay scale

  • Charges 20% regardless of how much the client pays you

Choose Fiverr if… you want to take a more passive approach and let potential clients find you

In my experience, UpWork yields better results than Fiverr. Typically on Fiverr, potential clients are looking to cut costs and thus will offer lower prices for freelancing services. Additionally, clients tend to be much less established and experienced in hiring contract workers.

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Once you’ve selected a platform, it is important to narrow in on the unique skill set that you can offer potential clients. Position yourself as a thought leader on those refined skills. To build a strong profile, ask yourself the following questions:

  • Do I have intimate knowledge in a certain industry or field?
  • What are other freelancers in my field showcasing and highlighting as their ‘unique’ skill sets?
  • What are clients seeking out? Is there a pattern in their asks? Are there specific platforms or skills that keep appearing in their projects?
  • What keywords are they using/asking for? How can I incorporate those keywords into my profile?

A great way to start building your profile is to look at what other freelancers include in their profiles. Here’s my UpWork page for example:

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Once you’ve narrowed in on your unique skill set, be sure to include it in your tagline. Your summary should then fully explain what you are good at and how you have come to acquire that skill. Using my profile as an example: I emphasize in my tagline that I am an expert in digital marketing and advertising management. In my summary, I identify the exact skills that fall under that skill set and identify my unique experience that supports those qualifications.

> Action Item: To help you get the ball rolling, think about your past job experiences. Identify the technical skills you used, job responsibilities that fell solely on you and the areas in which you have in-depth knowledge.

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When you’re just starting out, it is important to identify how much time every week you can devote to freelance work. Some clients will have quick timelines that require a lot of work over a small period of time; others will be looking for you to sign on for a more long-term gig. Before you start applying to every job you see, think about how you will incorporate the project into your current workload. Here’s how I identified appropriate projects and balanced my time.

  • Create job filters that suit your specific preferences (i.e. project length, client hiring rate, reviews, etc.).
  • Spend time every day applying to a few contracts. It is good to get in the habit of reviewing and responding to contracts every day.
  • Set time aside for each client (Google Calendar is your new best friend if it hasn’t been already).
  • Always slightly overestimate the amount of time it will take to complete the project. Give yourself a buffer for consultation time and any unforeseen changes and updates.

What I didn’t think about when I first started freelancing was the fact that I would not be getting paid for time spent finding new business, answering clients’ unforeseen questions (sometimes outside scope of work), sending emails, scheduling calls, and all of the other administrative undertakings. These time management and customer retention tasks are essential in doing your job well but because you are not technically getting paid for them make sure to build these into your rate. It’s tough to make a judgment call when you’ve only spoken once but try to choose clients who you think will be easy to work with so you can spend more time doing the actual work they hired you for.

Starting to Pitch Potential Clients

When you’re bidding on and interviewing for contracts, it is vital to listen to the clients’ needs and tailor your pitch to suit them. There is no one-size-fits-all approach to gaining clients, but these approaches will help you get started:

  • Don’t overload your pitch. Focus on selecting specific skills and offer concrete advice on how you will solve their problem or add value to their project/business.
  • If they provide a detailed description of what they need, remember to include how you would approach the project and some solutions you might offer.
  • Include a few times to chat and a means of contact (I recommend Calendly to schedule and for video calling).

Though each cover letter should be uniquely tailored to each potential client, it is helpful to draft a couple of templates based on jobs you foresee applying to often. Here is one of my B2B/Lead Generation focused cover letters:

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> Action item: Draft a few basic cover letters that will be relevant for jobs you will be applying for often.

Once you start getting responses to your pitches, it’s time to prove why you are the right person for the job. Set up a call with the potential client to discuss the project and how you plan to work with them.

These tips will help you seal the deal:

  • Be confident in your abilities. Clearly state your qualifications and how you can help. Clients want to work with freelancers that are experts and can provide them guidance.
  • Listen to the clients’ needs. Clients want to know that you are able to listen and focus on their unique needs.
  • Restate their business goals and clearly identify how you are going to help them succeed in reaching them.
  • Start with a lower rate to gain new clients quicker. With each new client, raise your rate a bit.

> Action Item: Start taking as many interviews (calls with potential clients) as possible and you will start getting more comfortable. This will help perfect your pitch and value proposition.

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  • Don’t be afraid to ask for reviews. This will be the lifeblood of your future business. Reviews on LinkedIn are a great way for potential new clients to gauge whether you are a good fit or not.
  • Create your own website or portfolio ( to show off your work. This will give clients a reference point for why they should hire you.
  • UpWork has a portfolio section where you can showcase the work you did for each client/project. You can take this one step further by creating case studies that include metrics on performance so you can share it with potential clients.
  • Start networking and performing growth hacking strategies to get off-platform clients so you can keep the percentage that UpWork and Fiverr takes. I’ve gotten most of my off-platform clients either from referrals, email marketing campaigns, and LinkedIn messaging outreach.

What’d I miss? Share what you think is important when embarking on a full-time freelancing career in the comments.

Connect with me on LinkedIn, check out my website, or send me an email with questions, thoughts, and/or suggestions you have —

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