How to do good work (Part 2): “Staying upwind”
If we cannot look too far into the future, what should we do?
In Paul Graham’s “How To Do Great Work”, he talks about the idea of “staying upwind”. Staying upwind means that at each stage of your work, you do whatever seems the most interesting and gives you the best options for the future.
In reality, oftentimes we cannot plan too far ahead, or our plan won’t be the same as we want it to be, or our inspirations might shift in the future.
Thus, the key to doing good work is to find something that you are genuinely curious about right now and start working on it. You start trying projects, meeting people, reading books, and asking lots of questions.
The key is that you start building something, finish this ‘something’, and evaluate how or where you should keep going.
Staying upwind doesn’t guarantee a clear plan and direction yet. Working on something you are excited about doesn't mean the journey will be straightforward. Ideas might not turn out the way you imagine them to be. There might be obstacles that stand in your way. New ideas might pop up that contradict your old or current ideas.
Inspiration is one thing. How it actually looks like in reality is another thing.
The key to staying upwind is not to let your inspiration blindly take the driver's seat of your work but to stay curious at every stage of the work to figure out how you can progress.
The key to staying upwind is to admit that you were mistaken when things didn’t go as planned or that you don't know enough and be willing to shift your plan and direction so that you continue to stay upwind, to follow what seems most interesting to you.
Along the way, you might need to redo an entire product. You might need to scale down. You might need to change your target customers.
Early this year at MỞ, it was painful to admit that we might not realistically get the number of students that we aimed for. We had to admit that our original plan to scale 3 courses at once was not feasible. We decided to just focus on one and try increasing the number of students in this one course.
Three years ago, we wanted to host so many courses with so many creators and we pitched about the idea of unconventional topics. Now, we build one course with two creators and we pitch about the value of community in learning. Where we are now is different from where we thought we would be three years ago. Similarly, where we are in three years will probably be different from what we are imagining now.
We cannot look too far into the future. What we can do right now, however, is to do what we are most curious about and what seems to be the best option for the future.
