The Founder’s Paradox: How to Make Time for Strategy in an “Agile” World

“To get off the treadmill.” I once asked a friend why he moved from Silicon Valley a few years ago and this is what he said. But I am not sure there are many places you can go these days to avoid it. Unless you make a conscious decision to slow down. And many of us do not want to — we all have our reasons.

I have a deep sense of purpose and an appreciation that life is short — I find meaning in individual and team achievement.

That achievement is not limited to professional work either. As another friend ribbed yesterday teasing, “You just volunteered to manage the soccer team to use up the extra five free minutes in your day and stay out of trouble.” I laughed, but there is truth there. Because despite trying not to think of myself as constantly on-the-go, I am.

Aha! is one of the fastest-growing software companies, with nearly 100 teammates. I have a lovely wife and three industrious, active sons. There are friendships to tend and community service to do. We like to travel. And I strive to be present and committed to everything I take on. To do so, there are trade-offs and other activities that I just cannot attend.

It also means that I must go fast. And I bet you feel the same — the details of my life are unique (as are yours) but the general feeling is not. We run from one activity to another and are consumed by data, updates, and news on our screens all the while. We focus on what is next, which makes it easy to miss out on the now.

The defining theme of this era might very well be that we are all moving fast. Very fast. 

And for those of us who build companies and products, the indoctrination is to move even faster. We are “agile.” We do it in the name of creating more value for our company and ourselves and to reduce the risk of building the wrong thing along the way. We can rapidly iterate. And for the most part, speed wins — when you know exactly where you are going.

But without strategic focus, speed becomes both the vision and the result. But it does not mean that anything of value will be created. You need another grounding principle beyond rapid iteration — you need deep thought and strategy. And for your mind to think beyond today, you need to carve out dedicated time.

Physical, mental, emotional, and spiritual space — you will need it all. And you will need time for meaningful inspection and planning. Here is what I do to ensure that I can think bigger and ensure that even though I go fast I go with purpose:

Physical

Whether you work remotely like we do at Aha! or are co-located in an office, you need to set aside dedicated time to focus. Block it off on your calendar. I do my best to set aside a day each week for this, which I call “Wonder Wednesday.” I know I need to be focused and not jumping between meetings. Then, I choose a physical space where I know I can do my best work — for me, that is in my home office.

Mental

Strategy requires that you are able to process information at a high level. You want to clear out any mental clutter. I try to complete any outstanding to-dos, calls, emails, or other work that I know will be lingering in the back of my mind before “Wonder Wednesday.” I ask the team not to give me new to-dos to complete that day. It also helps to let folks know you are going to be semi-unreachable. Our team at Aha! generally does not schedule meetings with me on Wednesdays, for example. Just try to free your mind from distractions as best you can.

Emotional

I am not referring to sadness or anger. (Although those types of emotions should be considered because it is difficult to make sound decisions if you are feeling unbalanced.) I think it is critical to understand where you are and try hard to not carry emotional baggage. Think about the “why” behind negative feelings in the past and how you can move forward with clarity.

Spiritual

Some hear the word “spiritual” and think of religion. But that is not what is intended here. Thinking strategically requires you to enter a frame of mind that is bigger than yourself — where actions have a meaningful purpose. First, you need to know your values and be open to other points of view. Cultivate curiosity. Build resilience. Some people meditate or do centering breathwork, which can help with all of the above.

Knowing what you need in these four areas will help you find inner reserve where you thought you had none.

Distractions and demands on your time will not cease. But it is possible to move extremely fast and also think deeply. This is another paradox — one that we all must face every day, no matter what achievement we choose to pursue.

Those who perform at a very high level are able to live with this tension. You grapple with it, understanding that it is not something to be solved. Instead, it is a continuous process of self-evaluation, reframing, and growth.

Read more of The Founder’s Paradox.