Building Confidence Through Accumulating Evidence: Niche Finding in the Marketplace

Over the past decade, tech freelancers have experienced a relatively smooth ride. Instead of actively seeking out clients, opportunities seemed to present themselves effortlessly. With the ability to command high daily rates, many of us grew accustomed to this flow without realizing that we were merely riding a wave, not actively steering our course.

However, navigating through challenging periods in life unveils a harsh truth: confidence often wanes when faced with financial struggles, health issues, or strained relationships. What once felt like unwavering self-assurance suddenly dissipates. Recognizing this vulnerability prompted us to initiate a sales master class within our community, tailored for digital entrepreneurs and freelancers. The realization dawned upon us that most of us had never honed our selling skills because we never had to. We had taken our market position and the influx of business for granted, fostering a sense of false confidence.

Upon closer examination, it became evident that many members of our community identified as generalists rather than specialists. While there's no inherent fault in being a generalist—I count myself among them— the critical question arises: "What is the primary challenge confronting your client?" More often than not, it's not a lack of generalist skills; founders typically fulfill that role. This realization led me to reconsider the wisdom of advertising oneself as a generalist, echoing the sentiment of "Never outshine the master" from Robert Greene's "48 Laws of Power." Signaling to founders that their approach is inadequate can be counterproductive.

Furthermore, considering the stage of the company is paramount. While generalists are indispensable in the early stages due to their versatility, as companies mature, they gravitate towards specialists to fulfill specific functions. This doesn't discredit the value of being a generalist, but it underscores the importance of strategic positioning in a competitive market.

Novelty seeking is a trait often associated with generalists, who thrive on the excitement of new challenges and experiences. Pete Davis, in his book "Dedicated," explores the idea that novelty seekers find pleasure in exploring various interests rather than committing to one thing. Neuroscience suggests that novelty-seeking behavior is linked to dopamine release in the brain, which reinforces the pursuit of new experiences.

However, building the habit of doubling down on a specific skill or area of expertise can be challenging for novelty seekers. It requires discipline, focus, and a willingness to forego immediate gratification for long-term growth. Yet, as Davis argues, dedication to a singular pursuit can lead to mastery and fulfillment beyond what fleeting novelty can offer.

To stand out amidst a sea of service providers, leveraging warm introductions and emphasizing confidence and energy are crucial. Identifying the aspects of work that bring genuine satisfaction and where one excels enables one to carve a distinctive niche. Confidence, far from being an innate trait, is a skill honed through a deliberate process of accumulating evidence of one's capabilities. Harnessing this confidence empowers fruitful conversations with clients, capitalizing on one's expertise to solve their problems effectively.

I've tried to sell myself as a generalist many times. While I was hired as an interim CPO, I had many conversations with founders, pointing out areas of the business that were far from optimal and detailing how I would improve them. Those conversations never ended in me working as a generalist or selling more projects to other freelancers; quite the opposite. The more I talked about it, the less they listened, even if they knew I was right. As a founder, you have a lot of balls to juggle, and having a know-it-all generalist by your side doesn't really help solve these problems. Most founders are pretty aware of the problems they're facing; it's just a question of prioritizing tasks with their limited resources.

By all means, be a generalist. Know how to do many things. Be like 80% amazing at them, but don't tell anyone. Then excel at the ones that combine confidence and high energy and position yourself in a way that you're the top dog in the game. For example: If you are an engineer and you know a lot about machine learning and AI, but the client is looking for somebody who has experience in Google Document AI, and you have none. Do you think they would hire you over somebody who does, just because "it's not hard to get into it?"

Imagine you want to climb Everest and you have never done that before. You can choose between a guide who's been on other tall mountains before and a guy who's been to the top of Everest 20 times before. That doesn't mean the Everest guy is not good at climbing other mountains; he's just one of the best to climb this specific mountain. Now do you know which mountains your clients want to climb?