A blog by Josh Berman, Executive Director, Catapult Chicago2021 has become a business destination for most. No more so than within our early-stage startup Catapult community. The need to plan is, of course, as critical as ever. As a business leader, nothing is as challenging or critical as strategic planning. But how to build a plan based on and in an environment that is as intensely fluid as what the COVID-19 global pandemic has created? “In preparing for battle I have always found that plans are useless, but planning is indispensable.” -Dwight D. EisenhowerFor many founders across Catapult, this is not your first rodeo. Like me, many of you have experience creating and implementing business plans. Recognizing our Catapult founders lead very different businesses, as we plan for 2021 we have a unique opportunity to leverage this comprehensive community IP. But how to design a plan in a pandemic? In an environment that is certain to change? Dramatically. Frequently. Without notice."Everyone has a plan 'til they get punched in the mouth." -Mike Tyson1. My very first planning step is to, well, procrastinate. That might seem like an odd step to incorporate; however, it’s a step that I highly recommend. I build in time to let my mind wander because I know it will. And it should. I guide myself. I listen to podcasts. I read. I set up Zoom meetings to discuss ideas with diverse business leaders. Quick tip. One spot I find myself these days is scouring Chicago tech listens and reads. Additionally, LinkedIn is another go-to source for inspiration (you might have noticed how much I “Like” all of you and your companies!).2. In my role leading the operations of our Community business, I write three working drafts. The drafts are directionally unique with very different operational plans. With this approach, I force myself to pick up my head and envision mission-based outcomes, camel-like survival tactics, and time tested perspectives. 3. Test-and-validate. At this point, I share what might appear to be a scattershot approach with trusted and divergent stakeholders. I discuss my thinking and my approach. I seek feedback— critical feedback. Here is an overview of the framework that works for me: 2021...I never knew you. I put on blinders and I build on and out from the plan I first envisioned.2020...part II. I focus only on what took place in 2020 and assess how best to keep the lights on to survive until business conditions recover.Back to the future. I am old enough to leverage what I experienced in 2000 and 2008. I go back in time and leverage the most similar conditions, mapping out plans that mirrored steps taken and how we performed.In this way, I force myself to triangulate my thinking and planning. It works for me. I find myself with a more rigorous plan. I also find myself mentally prepared (at least, more at ease) for the change I know is coming to me and the business. In summary, some well-worn truths I am holding to as I look to lead Catapult Chicago into 2021. “If you don't know where you are going, you'll end up someplace else.” -Yogi BerraWhat works for me:Find coopetition and read about each. Discover been-there-done-that leaders, and learn from their experiences. Surround myself with a talented team of generalists. Establish a team of anything but yes management and doting head advisors.Actively listen. Test and validate. Repeat step five as often as necessary.That’s my approach. How do you approach strategic planning? What actions are you taking as you develop your 2021 plans? Please share what works for you by emailing me at josh@catapultchicago.com.