Life and Marketing - Iterating Your Way to Success

I was just 16 years old when I got my first job in tech. Well, kind of in tech. I had stumbled into a strange world one afternoon while shopping in a strip mall in the Crossroads neighborhood of Bellevue, Washington, circa 1999. I was lured into the dark storefront by a towering mural of bright blue aliens fighting what I now know to be Zerg in a larger-than-life depiction of a game called Starcraft. Women were a rarity in that environment it seemed, because upon entry, I was offered a job as a “counter girl.”


I’d spend the next couple of years catering to (exclusively male) LAN center customers who paid by the hour to play games like Starcraft, Quake, and especially Half-Life: Counter-Strike on our high-powered, hand-built gaming machines, private servers, and dedicated T1 high-speed connection. (This was back before we all had supercomputers in our pockets and lightning- quick internet at home.)


Considering my professional experience to that point had included selling my mother’s watercolor paintings at the seasonal art fairs, delivering newspapers, and sorting mail at the local private mailbox retailer, it was quite the change of pace. What I didn’t know was that it was going to fundamentally alter the trajectory of my life.


Image a road surrounded by fall trees

I always knew I would pursue a life of writing, editing, and communication. It’s been the heart of me for as far back as I have memory. But when I enrolled in college classes for the first time in 2001, that job’s influence t led me to pursue a certificate program in iterative design. I was driven by curiosity, desire for productivity, and a vague motivation to bridge the worlds of writing and video game development. What I got was a new, and long-enduring pivot on my perspective about how to move through life.


Wikipedia defines iterative design as a cyclic process of prototyping, testing, analyzing, and refining a product or process. It is essentially a rapid, repeating, and purposeful trial-and-error process. Typically used in early prototyping for websites, apps, and user interfaces of every kind, to me, the discipline was immediately and obviously applicable far more broadly. The way I saw it, the process could be applied to literally anything:

  • Imagine the desired outcome

  • Identify the variables interacted with along the way

  • Adjust one of them, move forward

  • Record results in regard to the desired outcome (but also anything else that noticeably shifted)

  • Adjust the path forward based on learnings

To me, this was a path of freedom, possibility, and endless learning. There were suddenly no wrong turns, only more and less effective ones, and everything could be changed based on the results of experimentation I could embark on at any time.


I could iterate my way to anything, I thought. And, in a way - whether it’s my ongoing quest to build the perfect camper van, to find the most personally favorable region in which to live, or to accumulate the exact right combination of thoughts, beliefs, and ways of thinking to ensure a peaceful experience of the rest of my life - I’ve been iterating just about everything since.

It won’t surprise you to hear, then, that I think about marketing in the same way. Whether it’s a task as finite as writing a subject line, as comprehensive as refining a product for an opportunistic vertical, or as multi-pronged as driving a customer down a conversion funnel, iteration is at the heart of everything. And at Wheels Up Collective, that shows.


At Wheels Up, we think of every piece of content we create for clients as a prototype, every campaign we run a test, every outcome a learning, and every cycle of an ongoing engagement an iteration. Depending on client appetite, we sometimes get even more directed in our iterative learning process with defined KPIs, established performance goals, specific measurement plans, campaigns designed with test-and-learn optimization outcomes in mind, and decks cataloged with learnings over time.


Whether it’s in a marketing plan, or in life, it’s remained in my experience to be salient and true: When you approach your efforts with intentionality and curiosity, when you review outcomes with detachment and interest in learnings that can move you forward, when you’re committed to iterating your way to the outcomes you most desire, there really is no way to go wrong. At least, that’s what the path that began with the bright blue alien-vs-Zerg mural and the opportunistic hiring practices of that LAN center would have me believe.


Want to take a test-and-learn approach with a subject line, marketing campaign, or content strategy? Drop us a line. We’d love to help guide you along the way.