Freelancers: The downside of pitching to prospects

November 17, 2023

With parts of Robert Vlach’s latest editorial from our newsletter being shared online, thanks to Sarah Duran and others, here’s the full text in case you’d like to read it. If you find it interesting, you can share the LinkedIn version, subscribe to our newsletter or get your copy of The Freelance Way.

Let me be clear: Pitching to prospects (i.e. reaching out to new, potential customers) is a valid business practice.

However, as I read through articles and guides on the subject, I often find that the downside of this technique is rarely mentioned. Quite the contrary, pitching is often pitched as a singular way to generate new business.

Before delving into details, it’s important to note that pitching is more integral to some fields and business cultures than others. For example, it is far more common among writers than among programmers, and more prevalent among freelancers in the U.S. than, say, in Germany or Central Europe. It usually makes more sense in fields where it is a widely used practice.

Nevertheless, the downsides of pitching are universal and if you decide to employ the method on a regular basis, you should be aware of its serious limitations, especially for more established freelancers.

The problem is that the more experienced and booked you are, the more you want to pick the work you do under your own terms. Indeed, with the most sought-after professionals, new clients have almost no negotiating space to speak of, because there is such a great demand for their services.

In contrast, pitching often involves reaching out to potential clients and trying to sell them something they may not need. This requires, among other things, attractive pricing and a willingness to adapt to less-than-ideal conditions that nonetheless allow for a deal.

Consequently, adopting pitching as a primary selling strategy can create an illusion of control—the illusion that you're in charge of choosing your clients and setting work conditions, while in reality you may be digging a pricing and negotiating hole for yourself.

I know this, because I am often on the purchasing side, hiring some of these “always-be-pitching” freelancers for my clients. The hard truth is that it is far too easy to extract value from them, while not committing to anything substantial. And it is not even an unfair game, because they sell themselves so hard, we don’t even need to push. I can’t recall a single occasion when we thought, “Well, that was really expensive.“

It’s a different story, however, when we send an inquiry to an established freelance expert. We’re on the demand side, so there is no preconditioning for getting a good deal out of it. If it is someone in high demand, we may be lucky to get at least an expensive offer (still better than none). The deal flies, because there is a real need and demand.

A common counter-argument is that pitching keeps all options open for the negotiation phase. But it isn’t entirely true, as being on the selling side has its rules, and the seller often must take several extra steps or concessions for the deal to happen. This creates a sort of precedent in the relationship—and trust me, it is then quite complicated to start playing hard-to-get later, if you want to create leverage for, say, a much higher price.

I’ve observed that habitual pitchers (“send at least 3 pitches a week”) are busy but ultimately undermine their business in the long run. Their value is often being extracted, raw and clean, by the clients, while there is less space for them to upsell that value, given the original conditions of the deals they made.

They also receive positive “sell” signals more often, which makes them less likely to abandon the practice and more likely to praise it to other freelancers. The condition is similar to underpricing and selling your services on the cheap. There, signals from clients are also “positive”—because they buy so cheap in the first place!

Real-world adoption is low. Freelance surveys rarely highlight pitching as a prime strategy for getting new clients. For instance, in a recent survey conducted by Freelance Business (referenced below), only 16.8% of freelancers identified pitching as a source of new customers, while the top spots were dominated by recommendations, social media, and inquiries via website. All of these offer a far more advantageous starting point in negotiations.

To conclude, I find the pitching strategy workable and legit, but somehow misrepresented in the public discourse. It puts freelancers in a slightly disadvantageous starting position, and unless there is a very strong compensating strategy, its accumulated long-term results are far from impressive. Sending out a carefully crafted pitch from time to time is fine. I would just be very cautious about making it a primary marketing strategy.

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