It hurts to think about how much of the business I want to improve. I want to learn to code, so I can open my eyes to what is possible. I want a delightful user experience and a new training platform. I want to run customer interviews, to better manage our partnerships, analyse our subscriptions and interpret our data. I want to be more present to the team, to delegate more tasks and deliver more feedback.
This is the challenge of the bootstrapped business. With limited resources, each week I determine the small number of things to work on that have the capacity to produce the greatest results. I carve out time to work on those tasks alongside internal and external meetings, urgent tasks…and living a life. But it never feels enough1.
Recently, I have fallen into analysis paralysis, spending a disproportionate amount of time trying to find the right answer in a world of incomplete information. Every decision had to be reconciled with my worldview. Every decision had to be perfect. My thought process was a far cry from the lean startup methodology which involves building small experiments, measuring the outcome, and iterating based on my findings.
This paralysis has extended from hiring and launching our new community to writing this newsletter. With expectations, the mental load becomes disproportionate to the task, and it becomes too difficult to start. The bar is set so high that nothing is ever good enough.
I want to go back to executing with speed, to ask myself, as Dave Girouard suggests, ‘Why can’t this be done sooner?’.
A lot of people spend a whole lot of time refining their productivity systems and to-do lists. But within the context of a team and a business, executing a plan as quickly as possible is an entirely different concept. Here’s how I’ve learned to execute with momentum.
Challenge the when.
I’m always shocked by how many plans and action items come out of meetings without being assigned due dates. Even when dates are assigned, they’re often based on half-baked intuition about how long the task should take. Completion dates and times follow a tribal notion of the sun setting and rising, and too often “tomorrow” is the default answer.
It’s not that everything needs to be done NOW, but for items on your critical path, it’s always useful to challenge the due date. All it takes is asking the simplest question: “Why can't this be done sooner?” Asking it methodically, reliably and habitually can have a profound impact on the speed of your organization.
If I’m doing this right, expect shorter articles with less polish.
And now I’m going to press send.
As I write this, I am mindful of how much I am striving for more. Clearly, I need to re-read my last article.