In the past, deep expertise in one specific area or topic would lead to increased credibility, faster climbing of the career ladder, and growing income. 'Specialization', 'deep skills', 'core competencies',… buzz words that we have all heard thousands times, were synonymous with a successful career.  However, the current pace of change and technological advancements, as well as the additional uncertainty that Covid-19 has brought to the business landscape, is making the past career and skill beliefs counterproductive. The increase in speed and complexity demands an ability to thrive in ambiguous and poorly defined situations, a context that generates anxiety for most because it has always felt safer to generalize. Researchers, including me, believe, that the future will be very different: Breadth of perspective and the ability to connect the legendary dots (the domain of generalists) is as likely to be as important as depth of expertise and the ability to generate dots (the domain of specialists, to date). This represents a unique opportunity for generalist managers (in particular project management and agile experts), but under one prerequisite - they need to grow and develop their strategic competencies to be able to connect the dots from a holistic point of view, as well as their strategy implementation skills to become those that drive organizations into the future.