Yesterday, I had the pleasure of getting to know Samantha Novak, an impressive freelance sales writer based out of Canada.

A self-described “indoor cat, story addict, and total geek,” Samantha specializes in sales writing and doesn’t even have a personal website that I can find—yet, somehow, she’s managed to create a full-time freelance practice that makes her happy and pays her bills.

When I first sit down to start virtual meetings like this one, I never know quite to expect. Sometimes, the conversation requires a conscious effort and feels forced. Not with Samantha. She speaks quickly and clearly: she’s a fan of efficiency, she tells me.

During our introductions, she gracefully apologizes for the lighting conditions in her office, indicating a self-awareness common in the most successful people. In return, I joke that my fiancée’s office is the same way. Aware of our limited window of time, and driven by my eternal curiosity, I decide to jump right in.

Our interview lasted 25 minutes and uncovered many truths and insights about freelancing. Below is my rendition of Samantha’s words, which I did not record but instead took detailed notes on.

How did you break into freelance?

Samantha started on the classic university track, encouraged by parents who wanted the best for her and believed that was the right path. After uni, she entered the corporate job life as a workforce management analyst for PepsiCo.

About a year later, she transitioned to a similar job, considering the path of freelance along the way, but dealt with the difficulty of busy marketplaces like Fiverr, the hustle and grind, writing all the time and for meager wages. In her gut, Samantha didn’t feel that this was a viable path for what she was trying to do.

She considered process optimization as a service, but found that this type of work was mostly in demand by corporations, which felt like the same thing she’d been doing before—only as a consultant.

As a result, Samantha ended up back in writing, and found a mentor teaching a freelance course online. This was ultimately the influence she needed to successfully break into freelance full-time. She tells me,

If I didn’t have a mentor, even as a great writer, I probably wouldn’t have gotten to where I am today.

What was your biggest challenge getting started?

Without hesitation, Samantha explains that client-getting was her biggest challenge by far. She shares her belief in the importance of “putting yourself out there” no matter what:

Even when you know people, even when you’re doing well, the imposter syndrome is real—a lack of confidence, not knowing your own value.
You have to go to people. Sure, you will bother some people, but don’t try to be right for everyone, or avoid offending anyone.

As a startup founder, I resonate with this. One of the core tenets of startup innovation is putting your minimum viable product (MVP) into the hands of your users.

Samantha tells me how, in her experience, clients trade money for results and outcomes—not “stuff,” meaning the deliverables themselves, like a blog post. And I’ve found this to be quite true myself: clients almost always want the results that deliverables can get them, like new leads and engaged customers. Within reason, they tend to care less about what will be produced in order to achieve those results.

Validating your offer to potential clients

Regardless of industry, Samantha explains, freelancers must validate what their potential clients want. Like startup doctrine dictates, we must get direct feedback that confirms what our customers/clients care most about. Then, our job is to turn that into an attractive offer them. Samantha then drops her three steps to success:

  1. Validate your offer.
  2. Find a way to present it to new clients consistently.
  3. Scale that.

What are your best sources for new clients?

Again, Samantha doesn’t hesitate with this:

Relationships over everything.

She admits that cold emails and cold messaging has worked for her, but that it’s a much bigger numbers game—meaning reaching out to lots and lots of potential clients, just to get a few.

Instead, she suggests that beginner freelancers spend time networking online on platforms—like LinkedIn and Facebook—and that we find people who have questions, and help them out.

Indeed, building our online networks and providing value—real value, with no strings attached—are two of GigLoft’s core teachings. Clearly we’re onto something, right?

What worked well for you in the beginning?

One thing that made a big difference in Samantha’s early days was her understanding of business as it relates to people. She explains:

When you start thinking about business, it’s easy to divorce yourself from thinking about people as people—but you need to stay focused on the people, the audience, the psychology that drives decisions and behaviors. You can learn these things and use them to become better at what you do.

Her point is simple: while it’s crucial to understand how business works in order to add value to our clients’ businesses, we must always stay grounded in the reality that human beings are at the core of everything. We all have human egos, habits, reactions, needs….

When we start putting too much focus on the quantitative metrics, on the numbers, at the expense of the qualitative, immeasurable facets, our business (and our clients’ businesses) can suffer as a result.

By keeping human psychology at the center of everything we do, we can be better freelancers for our clients, and we can help our clients be better for their customers.

How did you discover your niche service offering?

Samantha shares that her mentor started by teaching her the skill of blog post writing, which led into the wider landscape of content marketing. From there, she followed a natural progression into email marketing and sales letters by listening to and anticipating her clients’ needs.

I mean, just look at this LinkedIn headline:

samantha novak freelance sales writer linkedin profile by-line

Is that speaking the right language, or what? It shows that she understands exactly what businesses care about, and how writing achieves those results.

What is your biggest challenge now?

Samantha admits that her current challenge involves staying consistent about putting herself out there. When we’re busy doing work for clients, it’s easy to lose track of the activities that lead to new clients and opportunities.

Even if you don’t have space for new clients, you should still be putting yourself out there.

That way, if work suddenly dries up, we’re not playing catch-up.

What advice do you have for beginner freelancers?

Samantha shares several bits of useful advice during our conversation, which I’ve aggregated here into one section.

Always vet your offers.

Talk to people to see if your offer is going to work. Strive to understand whether the offers you’re making to clients are actually valuable to them. And, once you’re doing the work, ask yourself: is it getting the results it’s supposed to be getting?

Charge per project, not per hour or per word.

Samantha mentions that, while she has some basic packages and benchmarks from which to quote, she still creates a detailed scope of work for each new project. From there, she quotes a fair rate that matches the number of hours she estimates it will take her, but also the value that it will deliver to the client.

Avoid working on retainer just yet.

With each new client, Samantha likes to start with a one-off project to feel things out. If it works well, and the client is open to a retainer, then she’s happy to switch to an ongoing basis. To incentivize ongoing retainers, she offers clients a slightly reduced rate compared to what she would charge if split into individual projects.


During our call, Samantha recommends two books that are top-of-mind for her these days:

How to Write a Good Advertisement
How to Write a Good Advertisement is a short course in writing powerful, hard-hitting copy that can help you make your products and servi...
Predictably Irrational
Why do our headaches persist after taking a one-cent aspirin but disappear when we take a 50-cent aspirin? Why does recalling the Ten Co...

Why this great conversation happened

I’d like our readers to know that this insightful conversation started with a simple, well-written, friendly connection request from Samantha on LinkedIn:

I checked out her profile and thought it would be a great idea to connect, then engaged her in conversation, asking how long she’d been freelancing. When Samantha expressed her appreciation for what we’re doing at GigLoft, I offered to have a short video call to get to know each other, ask her about her experiences freelancing, and tell her more about the GigLoft mentorship program.

Some lessons here:

  1. When our LinkedIn profiles (and elsewhere online) are eye-catching, accurate representations of what we do, we increase our chances of receiving connection requests from people we want to connect with.
  2. When we send personalized, thoughtful connection requests, we increase the likelihood that the recipient will want to connect with us—and start a conversation.
  3. When we capitalize on a great conversation, and offer to move it to a video or in-person meeting, we can maximize the results of relationship-building efforts.

I highly recommend connecting with Samantha on LinkedIn. She regularly shares insightful content, including the square graphics in this article. She’s clearly someone who will continue to do great things for herself and others in her life, and I look forward to her continued success.

Cheers, Samantha!