Mon Apr 05 2021

Work intently, not relentlessly

There are two competing schools of thought in the world of entrepreneurship: one that defends that the entrepreneur should never sleep, never take a break, never be off. The other school of thought says that entrepreneurship isn’t everything, that your startup is not your life, and that you should never put it in front of other things.

These feel like two sides of a coin that leave no room for subtlety. If you are a card-carrying member of the first school, everyone else is a slacker who isn’t working hard enough. And if you’re on the opposite end, members of the school of never-ending hustle are senseless people looking for success at all costs.

I’m here to defend a third school of thought — the school of intentionality. It lies somewhere in the middle of the other two. The school of intentionality understands that entrepreneurship (and knowledge work in general) is a creative business. And creativity can’t really be controlled. There is no on/off switch for it. Sometimes you are all about solutions — sometimes, all you see are problems.

I’ve gone through both periods of intense flow and exclusive focus on the work (for years on end, even), and periods where the work took a back seat to other things (personal projects, real life events, nothing at all). I find I do my best work in the ebb and flow between the two — and based on recent conversations with friends and peers, I’m not alone. So, why then does this industry force us to be miserable?

A balanced approach to work seems like a solid way to avoid burnout, frustration and perhaps more importantly, regret down the road about the life not lived.

There is only one rule in the dusty, barely ever opened rulebook of the school of intentionality: do what feels right in the moment, but whatever that is, do it with intent. When you sit down to get work done, know why you’re sitting down. When something is not working, look inward to find out why that is — and ideally, take a break. Learn about what works for you, rather than trying to model the way you work off others — because learning from their past success is no guarantee of your future results.

Truth is there is no guarantee of success at either end of the “how to live entrepreneurship” spectrum. Ask around, and you’ll find that if anything, this industry is far from fair, too. Right place, right time, straight-up luck, or a combination of these, end up dictating where you and your business end up — more so than how many hours you put in this week. So, simply work with intent. When you are working, work to produce your best output. But understand when that isn’t possible and pause.

Some days I find myself putting in more hours than some might find healthy. And some days, I find my creativity just isn’t quite there, and I take things slowly. And you know what? I found that to work quite alright.


For some book-shaped explorations of this topic, I recommend Steven Pressfield’s “The War of Art”, Cal Newport’s “Deep Work” and “Rework” from the folks at Basecamp. Some of these lean heavily on either side of the aforementioned spectrum, so read critically. Speaking of Cal Newport, I found his most recent book “A World Without Email” to be quite interesting — and its scope goes beyond what the title implies. More on that subject soon.