Keith B. Nowak

Being an entrepreneur is a constant struggle between deep focus on a single task that is crucial to your company’s growth and broad awareness of opportunities, risks, and movement in an ever changing environment. 

To walk this line, I’ve found it useful to ask myself a simple question: What are you not thinking about, that you currently should be? 

As an entrepreneur, and now as an investor, I’ve found this question to be incredibly helpful in pulling your head of the sand to consider what else is going on outside of your laser beam focus. I’ve started asking this question when talking to my portfolio companies to help them think about carving out time daily or weekly to look around for a bit and see what else is going on that they are not currently considering. 

Asking yourself this question, or having an investor or advisor pose a similar question, can help you take notice of changes happening around you. Is there movement in the market that could affect what you’re doing? Have new opportunities popped up that should be reviewed? You should be occasionally examining of the world outside your daily to-do list. 

This question also is a check to make sure you are not avoiding addressing any tough questions. At any point in a company’s growth there are a few incredibly important questions that need to be answered. Can this thing be built? Will people pay for it? Can we scale? Etc. The most important questions at a given time should be just about the sole focus of the company. However, this is way easier said than done. Since there are so many unknowns it can become daunting to address them all. Sometimes is becomes easier to focus on what you have or can prove and fixate on these points. Or sometimes one of the hundred problems falls through the cracks. It is imperative that you frequently check your work to make sure you are not missing or avoiding other important questions or hurdles that you should be thinking about. 

I’ve found that asking yourself this question is also a great way to identify where you need help. If there is an answer to this question then maybe you should consider delegating the solution. Is there someone in the office or an investor that could help pick up the task? Or maybe you need to hire to fill this hole. If there is something you should be thinking about but can’t get to then find help with it as soon as you can. This is why you have investors, advisors, co-founders, and employees. 

Lastly, there doesn’t have to be an answer to make this exercise useful. Just pausing for a moment to consider all the other moving parts is crucial and an important habit to get in. A quick soccer related analogy…When dribbling a soccer ball the obvious tendency is to look down at the ball. However to become a top player you need to be able to dribble the ball while also looking around the field for your next pass. You essentially have to be completely focused on the ball at your feet while being aware of a constantly changing environment. There might not always be a pass when you look up but if you don’t get in the habit of playing like this then you will miss the passes when they are on. Entrepreneurs must be able to do the same thing. They need to be entirely engrossed by the day-to-day tasks of building their companies but they also must be able to pick their heads up frequently to survey the world around them. There might not be an answer to my question each time I ask myself it, but I need to get in this habit to make sure I don’t realize too late that there was something important I should have been thinking about.  

During Easter dinner a couple weeks ago I was talking to my 16 year old cousin about the apps she’s using lately. It’s always really interesting to talk with people who are not completely engrossed with technology, especially younger generations.

What I found most interesting is that my cousin and her friends do not use Facebook at all anymore. Facebook has such a strangle hold on social networking yet that dominance seems to be slipping. My cousin’s apps of choice are Twitter, Snapchat, Vine, and Instagram. I was really surprised to hear Vine has jumped so quickly from early adopters to high school halls. Looking at my cousin’s iPhone home screen, it’s as if all of Facebook’s components were pulled out and replaced by standalone apps. She couldn’t give a reason as to why Facebook’s no longer used by her generation. Just seems it’s not cool anymore. I don’t think this is enough to call an end to the Facebook era but I’d say it’s a nail in its coffin. The first bit of investment advice I pulled from Easter dinner is to not take Facebook as a given.

Based on the social networking habits of my cousin and her generation, there is clearly a shift going on to more public, more immediate and more sharing. This is old news. I wonder though if this is sustainable. I believe that the pendulum will shift back towards more privacy pretty soon. The history of social is a push towards more open. Each new product provides a bit of a better high. More information, more exposure, more frequent updates, etc., etc. I think everyone will eventually burn out and long for a time of more privacy and more peace and quiet. That’s not to say social networking will cease but I don’t believe it will forever be so deeply engrained in our daily lives as it is now. 

Indirectly my cousin also prompted me to think about the change in how the internet is perceived. This change is being driven entirely by mobile. For me, being online is using a browser or apps to access information on the internet. My cousin and her friends don’t think like this. It’s not there they are always online and don’t consider a state of offline. It’s that they see no need to go “online”. To them online is a browser on a computer. It’s what they use to do research for school projects. There is no other use for being online. Everything they want to do socially or personally is accessible from apps on their phone. Connectivity through apps has just become the norm and they don’t really think about this as using the internet. 

This change in perception of the internet is incredibly fascinating and I think it goes farther than the trite conclusion that mobile is the future. I think the broader and more interesting point is that we are moving back to a state where the internet is seen as a closed system. When AOL first brought the internet into peoples’ homes it was done through the AOL portal. Being online meant accessing the world of AOL - their content, their email program, their social tools. Companies even began promoting their AOL keywords in commercials. We’ve since moved far from that perspective of the internet and now we use browsers to access any site in the world. It’s a completely open experience. With mobile though, at least for younger generations, we are moving back to a state where the internet is accessed through a fixed  portal so to speak. And I don’t just mean Apple vs. Android. Apps in general have changed how the internet is accessed and perceived. The internet is now accessed in piecemeal through a variety of apps instead of with a browser. 

I think this is a relatively obvious trend but what stood out to me is that this is the internet for a younger generation. It’s not that the internet is powering the information and communication in the apps. The apps are the internet. The second bit of investment advice is that “mobile first” isn’t just a design theory but is a comment on how users are now perceiving where information lives, how they communicate with friends, and how to access products and services. “Mobile first” is not about making a site look good on an iPhone or building a slick app. It’s about understanding that users and customers think of an app like an old school AOL keyword. The app store is the internet.    

On March 17th, I ran the New York City Half Marathon. It was my second time running this race and this time I wasn’t in it just for the experience. I trained incredibly hard and was shooting for a specific time. Thankfully, on race day I had a very good day and was able to set a personal record with a time of 1:31:41.

Everything came together that morning and I felt like I could have run forever. That’s not always the case though. For every on day, there are plenty of off days. Days when you feel tired from the start and the last thing you want to do is keep running. Last weekend I went out for my first long run since the half. It was a simple 8 miles at a slow, easy pace. However, just after a few miles in I knew it was going to be an off day. Everything hurt, I couldn’t get focused, and all I wanted to do was stop. It’s incredible how much an off day can make an easy run seem so difficult and how much an on day can take away all your pain and exhaustion. 

During these miserable 8 miles, I got to thinking about on vs. off days. Two ideas came to mind about on vs. off days in life. 

First, can you optimize for on days? After months of training you don’t leave race day up to chance. The few days before the event you get lots of rest, hydrate, eat well, and stretch. Race day requires feeling great, going fast, and not getting tired. You need to control the inputs that will produce these outputs. Can this be replicated in the rest of life? There are on days when you feel creative, productive, and full of energy. And there are days when nothing seems to get done no matter how long you sit at your desk. It would be interesting to track all the inputs that make up a day - what you eat, who you spend time with, things you discuss, thoughts, exercise (type and frequency), mental state, relationship status, etc. Looking back from an on day, how did all these inputs play out for the previous few days? Can this be replicated every day to ensure, or at least try for, never having an off day? 

Second, it is incredibly important to not back down from off days. In training for a race there will always be off days. If with every bad run you gave up then you’d never get in the milage needed for the race. Sometimes it’s just about putting your head down and getting through the miles no matter how they come. Same with life. Some days are just shit. You cannot back down on these days. You need to push through. Get up, get moving, and do your best. During off days you probably won’t accomplish anything of importance but you have to still put in the effort. Head down, get in the milage. It will add up in the end.