Originally published March 19, 2020 on Medium. Revised March 14, 2022

A Baby Boomer and a Millennial walk into a bar…ok, it wasn’t a bar but my Zoom screen on two separate occasions. Despite the 30+ year difference in their ages, they shared a number of similarities: They’re both White, hetero men. Each, in his own way, was fascinatingly intelligent and meticulously self-educated on a wide range of topics from economics to politics, history, financial markets, permaculture, cryptocurrency, and more. Both spoke passionately and articulately — and probably could have gone on ad infinitum if I hadn’t crow-barred my way in every now and then with a question or comment. And in both cases, they described a highly ambitious, intricately detailed, and multi-faceted vision for how each proposed to bring positive social change to the world.

 These two aspiring entrepreneurs had found me through different channels. The Boomer heard me speak on a webinar about Community Investment Funds and contacted me afterward for a meeting; the Millennial found me through LinkedIn and YouTube. The Millennial requested a meeting specifically to provide advice and guidance on how to seek capital for his venture. The Boomer…well, to this day I’m not exactly sure what he wanted of me. And here is where we start to see some key differences between the two.

In my Zoom meetings with each entrepreneur, I discovered two very different approaches to self-regulation and openness to two-way discourse, which is not only interesting from a generational comparison but, I believe, also an indication of their potential success as entrepreneurs. As an entrepreneur myself, I have been in these guys’ shoes many times before, having to communicate my vision to potential investors, grant-makers, partners, employees, or customers in order to get a business up and running. It takes more than a polished, ambitious, and passionate pitch. It also requires clarity, focus, and a solid strategic plan. 

From my two Zoom-mates, who unraveled their respective ideas during calls that went way over the scheduled time limit, I discovered two visions that were so complex, multi-layered, and lacking in structure that I felt like I was trapped in a kaleidoscope. There were so many moving parts in each of their plans that one tiny shift changed the whole picture. As a result, the whole collection of concepts became increasingly unstable as more pieces continued to be added. 

There is nothing inherently wrong with having a big audacious vision for broad systemic change — as long as you have a well thought out, rational, and fundable strategic plan to implement that vision.

Unfortunately, what happens with many entrepreneurs, and certainly in the case of my two new friends, is something I call the ”Ooh Shiny” syndrome. It refers to the entrepreneur who, in the midst of developing their vision, discovers something tangentially related to their original idea and, like a magpie, chases after this new shiny object before fully implementing their original concept. It’s pretty common among entrepreneurs, almost part of our nature, and in its positive application is what makes successful entrepreneurs able to pivot toward a modified solution when their original vision hits a snag. But if allowed to run unchecked, the Ooh Shiny syndrome can keep many a good idea from ever seeing the light of day. When a would-be entrepreneur loses sight of what is “good enough to launch” and keeps tinkering away with add-ons and nuances, their idea becomes too cumbersome to launch and dies on the vine. 

Ooh Shiny syndrome was clearly having its way with the Boomer and the Millennial. Their original visions — and even some of the add-ons — had merit and I could see a potential market need in both their cases. But after listening to them describe their ponderous plans in a delivery akin to an infomercial (but wait, there’s more!) I finally had to jump in and ask, “So what’s the next step? What’s your strategic plan for rolling this out? What’s the revenue model? Where will you find the money to launch and grow?” 

The different reactions to this line of questioning from the two entrepreneurs was intriguing and foreshadowed their future potential, in my opinion. With the Millennial, my questions gave him pause. They stopped him in his tracks and made him think, question, and consider that maybe he was indeed losing his way in the labyrinth of ideas he’d constructed. My advice to him was to focus, prioritize, and simplify. This advice was not only acknowledged, but, I believe, even appreciated. We talked about boiling down his plan to a one-page business model canvas, a framework with which he was already familiar. By the end of the call, I distinctly sensed his excitement to channel his considerable energy toward this last-but-crucial stage of work that would prepare his vision for launch.

The Boomer was an entirely different story. As I pursued my line of questions that politely challenged some assumptions while also trying to discover anything that might resemble a strategic plan for launch, I was met with increasing pushback and frustration. Despite my assertion that my questions were posed in the spirit of helping to make his plan focused and stronger, I got the sense that my input was unwelcome. I can only guess that what he really wanted was my tacit agreement with the plan and a request to jump on board with his team. I may never know the answer because the call ended rather abruptly and I don’t anticipate ever hearing from him again.

So, what’s going on here? Is it purely a generational thing? I’m Gen X and thus younger than the guy who dismissed my feedback, and older than the one who appreciated it, so there certainly could be some kind of “age thing” happening. There could also be some gender bias issues wrapped up in the generational stereotypes. I’m actually quite interested in intergenerational dynamics but not expert enough to give cogent analysis here, and besides, that’s not my point.

My point is about entrepreneurs and their ability to get an idea out of their heads and into action. In fact, unless you have taken concrete steps to bring your vision into reality, you are not yet an entrepreneur. You’re not even really a visionary. You’re a dreamer. There’s nothing wrong with having a dream — therein lie the seeds of innovation, after all — but at some point, you have to recognize that you’ve got something viable and GO TRY IT. Set some goals and metrics, define the steps that will take you toward your goal, identify the resources you need, and then take the leap.  

Some find this part scary — whether they admit it or not — and stay happily spinning in the kaleidoscope, further refining their plan and piling on ever more bells and whistles. These are the terminal cases of Ooh Shiny syndrome. One thing that can save them is a committed, action-oriented partner who takes over the helm to bring the vision into being. This can be a very powerful combination, by the way. A balanced partnership of vision and action is the dynamic duo of the entrepreneurial world.

For genuine entrepreneurs, the implementation phase is just as exciting as the ideation. They take an idea, put it into action, learn from it, adapt, and keep innovating toward success. It takes courage. It requires acceptance that an idea — and its corresponding plan — will never be perfect, but can be good enough to get started. It takes faith that you have the creativity, agility, stamina, and strength to deal with setbacks when they arise. And it takes humility and self-awareness to accept support, guidance, and perspective from others because that’s how good ideas are made great.

So…a Boomer and a Millennial walk into a bar. They sit at opposite ends of the bar, order a beer, and start telling the stranger next to them about their great idea. A group of Gen X-ers sitting nearby overhears both conversations, talks among themselves, and then calls the Boomer and Millennial over to their table. They’ve pooled together $100,000 and offer it to the aspiring entrepreneur who can convincingly deliver his pitch in two minutes or less. One entrepreneur immediately goes into bargaining mode to try to get a separate, longer meeting. The group of investors just looks at him with blank stares. Then the other entrepreneur takes a step forward and says, “Start the clock.” At the end of two minutes, he is invited to sit down at the table, a round of beers is ordered, and a new partnership has begun. Which generation was the winner? Doesn’t matter. It was the one who took the leap.