\u00a0[Disclosure: Many of the companies mentioned in this article \u2013 OutSystems, AgilePoint, Compuware, CA, SkyTap and WaveMaker \u2013 are current or past clients of the author.]\nThe scene opens with the blue-grey drabness and cold columns typical of an old-school bank.\nA man walks through the scene lamenting fees and minimums as he grabs one of the columns and topples them with one hard push. They tumble down to reveal the colorful and modern inside of a new Capital One Cafe (complete with coffee bar and comfy chairs) where, he explains, \u201cthis isn\u2019t a typical bank. This is banking reimagined.\u201d\nIt\u2019s a great ad and an unmistakable break from the way most banks approach retail banking, even as most of them attempt to adapt to modern sensibilities.\nA crucial part of realizing this new banking vision, according to the company's CIO for retail and direct banking, is going all-in on the cloud. "Our main focus is\u2026to provide the best experience for our customers," explained Gill Haus, Senior Vice President, Retail and Direct Bank CIO & Technology Delivery Transformation for Capital One. "We want our customers to live the life they've imagined\u2026and in order to do that we have to spend as much time as possible on the user experience."\nAnd, as Haus and Capital One see it, that means committing to moving everything to the cloud.\nAs I sat down with Haus at last year\u2019s Amazon Web Services (AWS) re:Invent customer conference, I wanted to understand the bet they were making, if it was even possible to go all-in on the cloud, and, in the end, if it was worth the trouble.\nThe allure of going all-in\nThe World Series of Poker and its tournaments of mostly Texas hold \u2018em poker games has become a phenomenon, broadcast on live TV and attracting millions of viewers around the globe. And the most exciting moment, the moment that viewers anticipate with great delight, is when a player goes \u201call-in\u201d and pushes all of their chips into the pot placing a make-or-break bet.\nGoing all-in on the cloud shares much of the same allure as this riveting moment in a poker game.\nIt feels bold and daring. It communicates to the world that you are confident and that you will move decisively to win the game.\nAnd as we speed into the digital era, perception is reality (at least, in part) as organizations jockey to have their customers, investors, and prospective employees see them as a trailblazer marching confidently into the future, rather than seeing them as an artifact of a by-gone era.\nFrom its earliest days, those marketing \u201cthe cloud\u201d and cloud-based solutions have been masterful at creating this imagery. If you\u2019re in the cloud, you\u2019re modern and hip. If you\u2019re not, well, you can figure it out.\nMoving to the cloud has always been about investing in this promise. And, thankfully, companies like Amazon (via its AWS arm) and Microsoft (via its Azure offerings) have been working hard on making all of those promises a reality.\nAt some point a few years back, we reached the tipping point. Up until that time, it was acceptable to question whether or not the cloud made sense for your organizations or to take a measured approach to adopting it.\nToday, it\u2019s the opposite. If you are not a \u201ccloud first\u201d organization or preparing to go \u201call in,\u201d you must be prepared to explain yourself.\nAnd the storylines about moving aggressively to the cloud are compelling. \u201cWhen we looked at going all-in with the cloud and AWS, the rationale was that in order for us to deliver those [exceptional customer] experiences we were going to have to spend a lot of time on the infrastructure and components we would need to run the foundation to then build the experience on top of it,\u201d shared Haus. \u201c[The cloud] means we\u2026can do [things] faster than we could previously on-premises. Things that used to take months or weeks are now done in days and hours. This allows us to focus.\u201d\nAs companies like Capital One see it, there is no other option. From their perspective, the stakes are just too high, the demands too significant, and the technology is changing too quickly to do this any other way.\n\u201cThere\u2019s an experience we know our customers want,\u201d Haus explained. \u201cBy not just taking applications that exist and lift-and-shift them to the cloud, but by re-architecting them and thinking about them differently, we can provide those experiences\u2026and open up entire new worlds for us [and our customers].\u201d\nThat\u2019s the case for going all-in. And it\u2019s captivating. But beyond the rosy-cheeked optimism, the question remains: is this even possible?\nA pipe dream or real-world strategy?\nHave you ever had one of those moments where you got all excited about doing something big, how important it is, how great it would feel at the end \u2014 and then had that sobering moment of reality when, as you began the undertaking, you came face-to-face with the enormity and complexity of the task?\nWell, that\u2019s a moment that many enterprise leaders will be experiencing repeatedly as they attempt to go down the all-in road.\nAdopting the cloud, along with many other modern technologies, makes a ton of sense when an organization is executing a net-new, so-called greenfield project. There is no technical debt, no preconceived perceptions, nor any political baggage with which to deal.\nBut as organizations attempt to scale their efforts into their legacy domains \u2014 precisely what is required if you are to go all-in on the cloud \u2014 they run into all manners of challenges.\n\u201cIn an ideal world, the IT landscape would be a greenfield, where every organization could start with a blank slate and build out their optimum infrastructure,\u201d shares Sirish Raghuram, co-founder and CEO of Platform9. \u201cBut for most businesses, it is often more of a brownfield\u2014muddied with old systems and stodgy practices\u2014and it\u2019s not always clear the best way to build on top of it.\u201d\nThis muddy, messy world is where most enterprises leaders find themselves and the pathway to an all-cloud approach seems anything but clear. As a result, Raghuram explains, many organizations settle on a less dramatic path, \u201cAs more and more organizations look to a hybrid cloud approach as the infrastructure mode of the future, the need for a way to migrate legacy systems more easily is becoming an increasing necessity.\u201d\nThis need to bring legacy systems into the modern fold, in fact, has given new life to an old idea: modernization.\nThe new incarnation of legacy modernization, however, bears little resemblance to the multi-year, ridiculously expensive, and all-but-guaranteed-to-fail efforts of the past. Today\u2019s modernization efforts are all about making legacy environments relevant without necessarily throwing everything out and starting over.\nA whole host of vendors from across the technology spectrum are now stepping in to help enterprises modernize their legacy stack with these new approaches. This collection includes a vast range of technology solutions such as low-code development platforms (e.g., OutSystems, Mendix, AgilePoint), hybrid service providers that combine proprietary technology with professional services (e.g., WaveMaker, Synchrony Systems), and solutions that help organizations bridge the gap between legacy environments and the cloud (e.g., SkyTap).\u00a0\nWhile taking wildly different approaches, each of these companies is trying to help enterprise organizations ease the transition as they attempt to modernize (which is becoming increasingly synonymous with moving to the cloud) and overcome legacy baggage. The focus they are putting on modernization speaks to both the need to modernize and the challenge of doing so.\nAnd it begs a second question: is it even necessary?\nThe revitalization of the legacy stack\nWhile all this talk about modernization and moving to the cloud has been happening, there\u2019s another, related movement that has been gaining steam: the revitalization of these ostensibly outdated legacy platforms.\nThe poster-child for this movement is Compuware with its mission to "mainstream the mainframe."\nThe company\u2019s stated objective is to transform the perception of the mainframe as a legacy boat anchor and instead integrate it into modern DevOps toolchains. But in the broad context of legacy revitalization, they are hardly alone in this resurgence in perceived viability.\nTech companies as varied as IBM, VMware, CA\u2019s mainframe division (now part of Broadcom), and Mulesoft (now part of Salesforce), all have stories to tell about how they can help organizations revitalize their legacy investments and pull them into the modern age.\nEach of their stories shares a common theme: it's not the legacy stack that's the problem as much as how you're approaching it.\n\u201cCloud might be sexy, but mainframes aren\u2019t going anywhere anytime soon,\u201d claims Chris O\u2019Malley, CEO of Compuware. \u201cThe cloud and the mainframe are wonderful partners\u2026In truth, they do two different things well. When it comes to agile and DevOps initiatives, the mainframe should be first on the list for modernization. The mainframe has to go as fast as any other project you\u2019re going to work on. You\u2019re only as fast as your slowest digital asset.\u201d\nThe case O\u2019Malley and every vendor on the revitalization bandwagon is making is that these legacy systems are not nearly as outdated and obsolete as you may think.\nIn fact, the story goes, these systems are so vital and central to core operational business processes, that there is more significant upside to revitalizing and modernizing them in place, and more potential downside by taking on the costs, risks, and heartache of moving them wholesale to the cloud as part of an all-in effort.\nGoing all-in on value\nCynics and cloud diehards will claim that all of this is a red herring \u2014 the last-gasp attempt of vendors with a vested interest in the legacy infrastructure to remain relevant. But I don\u2019t think so.\nI am an ardent believer that we are not headed toward an all-cloud future, but rather towards an enterprise IT future defined by hybrid IT environments. These environments will bring together a broad mix of modern and legacy stacks, all reimagined and reorchestrated around the workload and the business value those workloads generate.\nAnd there should be only one answer to that question: because that's the most effective way of delivering competitive business value.\nI believe that Haus and Capital One are getting that right. He and the company are laser-focused on the competitive business value they must create for their customers. They believe that going all-in on the cloud is their best path to achieving that value.\nYou or I may disagree with that calculation, but the basis for their strategy is dead-on.\nFor most organizations, however, I believe the path to competitive value will lead to a hybrid IT model in which they rearchitect and move to the cloud where it makes sense and optimize the rest.\nBut as you survey your world, assess the competitive threats and market opportunities, and prepare your strategy to take your organization into the future, don't get sucked in by the allure of going all-in on the cloud.\nInstead, go all-in on delivering business value for your customers and let that lead the way.\nDo so, and you\u2019ll be sure to have the winning hand.