For Startups It’s Always January

January is when identity gets renegotiated. Individuals do it through habits—eating better, procrastinating less, finally working out—all ways of embodying who they aspire to become. Even if they don’t talk about it that way, organizations do something similar. The block for individuals and organizations alike is not to simply change your actions, but to actually change the thinking that leads to your actions. The challenge is to find your reset moment, your January, to make that shift.

Over the past five years, I’ve worked with hundreds of startups. In my classroom, I look for startups that need help on strategic projects as a way of creating learning experiences for students. These projects often revolve around helping startups consider new directions, new products, and new identities. In the past year, my students worked with Terra, a YC-backed manufacturing company exploring different industries as customers; PlotTwist, as they changed their positioning within the dating app market; and Fulton, a D2C orthotics brand exploring a new product. For students, these projects offer a white space to practice entrepreneurial skills. For the startups, they offer a fresh outside perspective.

Students are increasingly comfortable and excited about engaging with customers directly. In my classroom, students learn the art and science of what is often called customer discovery, which can require a bit of cringe as you get out of your comfort zone to identify meaningful pain points. In a digital world where so much is done online, there is a novelty to talking to customers in real life. But what I’ve found to be a harder lesson is slowing down to represent and capture what they are noticing and hearing.

In design, this shows up as artifacting. In a modern business classroom, it looks like putting together a slide before it feels like it fully says something. Artifacting turns private thoughts and early insights into shared engagement. It facilitates our thinking and ultimately forces us to make a claim that a particular fact or idea might be important. The problem is that the faster teams move, the more students begin to believe that action equals learning, so updating a slide feels like standing still. This tension isn’t theoretical. It shows up in real startup decisions.

That resistance showed up clearly in our work with Fulton. In one of our early projects, students were asked to explore adjacent markets, including the sandal category. Teams talked to customers, visited shoe stores, and reviewed existing products. Much of the work looked similar across teams. But one team paused a bit longer between steps.

On a single slide, almost as a throwaway observation, they noted an indoor house shoe as an opportunity. At first, it seemed counterintuitive. People do not typically think of shoes as something you wear indoors. That may not matter if shoes are only about protection. But it matters a great deal if the product is about alignment, support, and long-term joint health. That pause and the willingness to put the idea down shifted the conversation.

Fulton took that insight seriously. The house shoe launched in October (pictured below) and has since become their best-selling product. More importantly, it helped clarify how the company saw itself. Not as an indoor shoe brand, but as a health-focused footwear company delivering quality, affordability, and style. Indoor was not a limitation. It was the place where their identity became visible.

Early-stage startups are constantly shifting what they build and who they build it for as they search for product–market fit. Looking for new pastures, trying new tactics, and even exploring new identities are all part of what it means to be a startup. In a world accelerated by AI, where movement is cheap and iteration is fast, the pressure to keep evolving can be overwhelming. Constant motion, a defining feature of hustle culture, risks causing founders to miss the value of pause and reflection. This is why January matters.

January isn’t really about changing what you do; it’s about changing how you think about what you do. Someone can go to the gym because they feel they should, but that rarely forms a habit. When they start going because they see themselves as someone who works out, the same action produces a very different outcome. The same is true in startups. Even companies with only two co-founders can get stuck inside a particular belief about how learning happens. You can hear it in the language they use. Seeking to “validate” signals a belief that only data and evidence can provide direction, while cultures obsessed with “shipping” reflect a stance where output matters more than hitting the target. Each becomes limiting when treated as universal.

Nothing magical happens when the clock strikes midnight. But each year, individuals and companies use the calendar as an excuse to reset—to reexamine how they think, how they decide, and how they act. For startups, it’s always January. The real question isn’t whether you’ll keep moving forward. It’s whether you’re willing to change how you understand what your movement means and whether it’s still the right one for the moment. This is the kind of entrepreneurial intelligence I try to develop in the classroom: being fluent in different ways of learning, and willing to switch when the situation calls for it.