Strategy Should Hurt

“A strategy should hurt.” The trade-offs—where you invest time and resources and where you don’t—should be painful and disappointing, either internally or to your customers. There’s no such thing as a strong strategy that prioritizes everything at once.
—Scaling People: Tactics for Management and Company Building by Claire Hughes Johnson, former Google and Stripe executive

A well-articulated strategy must have a single point of leverage to exploit. Then, you can line up your organization behind that point of leverage. The more time and money you can put behind it, the more leverage you can create.

To align time and money behind the strategy, you'll need to take it from somewhere else in the business. This is when your strategy starts to hurt.

You don't have infinite resources. You can't maintain everything you're doing and add more work every quarter. The new work either won't get done or won't create real leverage. You'll just be half-assing more things.

In Tortuga's end-of-year planning, we create a list of new "big bets" and areas where we want to "double down" next year.

More importantly, we make a "no list" of things to stop doing (or not start doing) so that we have the resources to execute our strategy.

Time and money are pulled from the "no list" and reallocated to the "big bets" and "double downs."

If you don't cut or divert resources from other parts of the business to your strategy, you won't create any leverage.

Strategy should hurt.

Accept the sacrifices. Say no. Kill your darlings.