Planning for Success Can Be a Mistake—Hope Offers a Better Strategy You May Be Missing.

I know how that sounds—like a naïve hippie-grown recipe for the tears of failure. We aren’t typically wooed by the thought of magical thinking over the direct sex appeal of hustle culture. Not when our livelihood and egos are on the line. We like to at least *feel* like we have answers. This is especially the case if you’ve grown up in Western culture, where the “rise and grind” gurus and grifters of the social media blitz era are dying to sell you e-books and online courses about “life maxing”, and other reminders about how your existence has likely become one big disappointment.

It’s clever marketing to be sure. Targeting our fear of failure works. Through a carefully concerted campaign of competence shaming, beautiful people who seem to have it all figured out can convince the rest of us that we lack the skills needed to succeed on our own. In this model of living, success is some obscure riddle of exact science to be solved, where the right answer always seems to exist somewhere outside of you, just beyond one more paywall. And so we buy into it–both literally with our wallets, and culturally in our thoughts and actions.

But this messaging goes beyond the tangible products of a billion-dollar personal improvement market that can then sell you a formulaic solution to stress. Inherent in the message of “get your sh*t together with this program” is a deeply ingrained philosophy that any and all failure is the sole responsibility of the person. And it isn’t just marketing. It’s a deeply ingrained feature of how we live now. There’s something systemic about how we engage with an unknown future that perpetuates myths around the efficacy of planning for it.

Technology itself may be the greatest culprit here. At a time where communication is instantaneous and information ubiquitous, it seems only logical to conclude that, with enough effort, we can and should plan for absolutely everything, that all possible outcomes are within our relative control.

But like anyone who’s ever had a “bad day” can tell you: the future doesn’t care about our plans. Even the most meticulous planning can be easily derailed the moment life decides to throw us a curveball. And if we’re someone hellbent on having the right plan, when that curveball does hit, our anticipated pathway to success is broken along with our confidence to traverse it. This is precisely how “planning for success” can become counterproductive, even when, intuitively, it makes sense.

Let me preface this next part for clarity:

There’s nothing wrong with planning. Planning is sometimes a necessary and vital part of preparedness.

However, despite the two experiences being related, having a plan is not the same as being prepared. We can appreciate this distinction when, despite having toiled over a specific plan for success, we can still feel unprepared. That’s because preparedness isn’t achieved by any number of externalized actions that attempt to assume control—it’s an internal state of calm acceptance of an unknown future.

And while planning can certainly help us feel like we have a degree of control and preparedness, therein lies the catch: planning can become a detriment when it’s *mistaken for preparedness. When the plan itself becomes the focus and measurement of success, any unanticipated detour becomes a failure that erodes our confidence.

This is where hope might have more to offer.

Hope itself requires an acceptance of the unknown; it does not obsess over objective measures of personal control, but rather, relegates a portion of them to where they belong: into the nebulous void of the universe and its powers outside of our control. Hoping for any favorable outcome requires us to concede to the idea that the means by which an outcome comes into being is inherently unknowable.

It’s an uncomfortable premise–I get it. Hope goes against everything we’ve been taught to believe about how success happens, about how much control we really have. But this isn’t a clever nihilism wrapped up in a bow. Hope isn’t promoting success by chance in the prescriptive abandonment of careful planning. This isn’t advocating for a future by lottery—it’s much more nuanced than that.

Hope is a conscious and deliberate act. It is a genuine acceptance of our limitations in knowing how the future will unfold, and by way of that acceptance, allows us to engage fully in the process of striving. It is this striving—the very output of our will and control—that is easily stifled by the focus of planning and obsession with personal responsibility as it pertains to future outcomes.

This is the secret and hidden benefit to hope as a strategy that makes it superior to planning. For those that would mistake planning for preparedness, there is a trading of illusion for reality that saps our attention, will, and energy to engage fully with striving. Hope is different; it allows us to do what is within our power, and by unaccepting the rest, brings us into a true state of calm acceptance that, ultimately, improves our chances of success.