Over the years, I have tried harder to become a generalist and not allow myself to be trapped into technical specializations and list of skills. My resume has gone from being something most recruiters could recognize and properly categorize to something that does not lend itself to such tagging.
Finding the next thing to do now takes months of concerted effort where two weeks was plenty of time in the past. Yet, I know I am generally on the right track with my avoidance of specialization. It was interesting to read this advice from the investor Chris Sacca in the book Tools of Titans which is a great explainer of why I want to stay out of the specific, hard and tangible and focus on being able to explain why something matters:
"Whether you are raising money, pitching your product to customers, selling the company, or recruiting employees, never forget that underneath all the math and the MBA bullshit talk, we are all still emotionally driven human beings. We want to attach ourselves to narratives. We don’t act because of equations. We follow our beliefs. We get behind leaders who stir our feelings. In the early days of your venture, if you find someone diving too deep into the numbers, that means they are struggling to find a reason to deeply care about you.”
What is true is venture happens to be fairly true of software sales too. In the end, there is only so much that will differentiate you for your closest competition. If we had to compare two worthy products quantitatively, it would be close to impossible to pick a winner. The customer then asks the two vendors to participate in a bake-off to make a decision. That is the hard and painful way. But if the buyer finds something about Vendor A that stirs their feelings positively and make them want to care deeply about what Vendor A brings to the party, then the deep dive into numbers is often an after-thought. I have seen this to be true in many a deal cycle that I have been a part of.
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