Are You Underthinking Your Startup?

August 19, 2013

11:22 am

We’ve all heard the advice, “Don’t overthink it.” In particular for startup founders, the perils of overthinking have been well-documented – to the extent that we are constantly looking for ways to simplify our mission as we build our companies to avoid “death by overthought.”

As both a founder and a recovering overthinker, I try to ensure that everything from product to messaging to strategy is clean and simple. During a recent relapse, however, I got to thinking about the ramifications of this plight. Can you oversimplify things to the point where you’re underthinking your startup?

In some ways, I believe the answer is YES.

Take, for example, the lean startup methodology. Build-Measure-Learn, repeat. Pretty simple. I’m a big fan of this approach, and we utilize lean as a roadmap at my company, seedRef. That said – and despite the fact that one-third of the process is dedicated to thinking (Learn) – it’s easy to fall into a pattern of behavior that largely ignores the type of reflective thinking that drives us through this grinding process.

The same goes with being “data-driven.” Currently, I have responsibilities to lead and execute on nearly every facet of my company. There is, of course, a risk of spreading myself too thin and losing focus. I recognize this happening when numbers and data – absent the type of context provided by reflective thought – become shortcuts to rash decision-making.

To avoid falling into the mindless oversimplification trap, I’ve worked to incorporate reflective thinking into my daily routine – to both prioritize my efforts at seedRef and maintain a big-picture outlook. During these dedicated 10-20 minutes each day, I try to answer the following questions as honestly as possible about my company (these also work great on a personal level):

  • Where have we been?
  • Where are we now?
  • Where do we want to be?
  • Is what I’m doing today going to help us get there faster?

The first three questions speak to the big-picture goals of what we’re trying to achieve as a company. This is my motivation. My passion. My energy. Without these things, my work at seedRef is merely a job (and one that pays quite horribly, at that). The last question is something I use to filter new ideas. Being able to effectively prioritize is perhaps the single most important skill to master within a resource-strapped startup.

Another critical skill to master is perseverance. When I founded seedRef, I knew how hard it was going to be to achieve what we set out to do. Now, just four months in, I know that it’s about 10x harder than that. Paul Graham appropriately calls this place the Trough of Sorrow. The good news is that each day I know that I have a choice to make about the mindset I’m going to have. At our stage, there are really only 2 options:

  1. My company is going to change the world!
  2. Will my company even exist in 3 months?

After a few weeks of dedicated reflective thought, I’ve found myself in the first category far more often than not. Is this self-delusional? Some might think so. But the effect has been better, easier, more targeted focus and overall clarity of vision/strategy. After all, I know where we’ve been, where we are, and (most importantly) where we’re headed.

Of course, completely ignoring the second train of thought probably isn’t healthy (or possible) either. But harnessing a positive outlook certainly makes being in the trough of sorrow feel more manageable.

I suppose time will tell if I’m just overthinking the notion of underthinking, or if a simple daily exercise can have a lasting impact on achieving balanced thought.

Either way, I leave you with this.

“Simple can be harder than complex. You have to work hard to get your thinking clean to make it simple. But it’s worth it in the end because once you get there, you can move mountains.”

-Steve Jobs

Eddie Earnest is Founder and CEO of seedRef, a web-based platform dedicated to improving recruitment processes through automated, character-based reference checking.

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