At the start of 2019, 7 million U.S. jobs remained unfilled, and American employers consistently cite trouble finding qualified workers. While some liberals insist a "skills gap" doesn't exist, all evidence points to the contrary. These gaps are moreover made worse by a higher education system that ill-equips graduates for the workforce. America's economy has digitized over the past decade and the nation's legacy infrastructure -- postsecondary education institutions and workforce development boards -- have not come close to keeping up. Moreover, the digitization of the economy has also changed hiring practices, with real implications for the workforce. In this whitepaper, Ryan Craig explains that employers are leaving middle and high-skill positions unfilled for two reasons: (1) They are failing to find enough candidates with the requisite digital skills; and (2) They are dissatisfied with the "soft skills" (such as teamwork, communication, organization, creativity, adaptability, and punctuality) presented by candidates, even those with digital skills. None of these missing skills are surprising to candidates or employers. So why does the skills gap persist? Craig indicates there are two reasons: (1) "Education Friction"--because of the time, the cost and -- most important -- the uncertainty of a positive employment outcome, many individuals fail to upskill themselves; and (2) "Hiring Friction"--a growing reluctance of employers to hire candidates who haven't already proven they can do the job. In this paper, he explains how the skills gap is real, why it has not been close, and why it matters.