Swimming instructors warn us not to venture too far into deep waters. The risks get higher and higher the farther we swim away from shore. The fears of disabling fatigue, loss of direction, and overpowering currents all serve to give us pause before jumping headlong into the waves. Is the joy of adventure worth a bad outcome that we can’t undo? Knowing that I’m by no means an Olympic swimmer (and I would never encourage risky behavior), I prefer to keep closer to where my feet can touch bottom. But when we are tasked to take our organizations on a strategic pivot, how do we muster the courage to swim away from the comfort of our existing business model?

Digital transformation can be a gut-wrenching endeavor. Many times the goals are unclear, except perhaps in the broadest terms, and the path toward them even less so. Where do we start? How do we prioritize? How do we know when we are straying? My advice is to think more about progress over perfection: set our eyes on the horizon—to start with the end in mind—and then create our high-level plan or pathway.

As we counsel in Respect the Weeds, an informed point of view and an empathetic understanding of the unmet or unspoken needs of our customers are our best guides. Our North Star will be whether our steps move us closer to serving up value to our customers in the most efficient manner possible. Market and organizational storms will blow us off course, as will the false pride that every strategic path charted is set in stone, but know that we are not in this alone. An organization that truly believes that it must change in order to survive or thrive will push past the steady-state, overcome the inevitable setbacks and retrenchments, and swim collectively toward our desired outcomes.