By Andrew McConnell, co-founder and CEO of Rented.
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Since my company went fully remote at the beginning of 2020, I have been working remotely more and more from #bermudaful Bermuda. As a lifelong swimmer, one of the great appeals of the island is the ability to hop into the ocean year-round and swim (275 days consecutively at one point). The swimming has also helped me build my social connections on the island, and each weekend I join a group of similarly insane open-water swimmers for some incredible adventures.
On a recent Saturday morning, however, our group was much smaller than usual. At the last minute, more than half of the regulars dropped out because of the weather that morning. Specifically, it was raining. As I read the WhatsApp messages canceling, I could not help but think back to the statement by Seneca, the Stoic philosopher, that “We suffer more in imagination than in reality.” The reality is we were all going to get wet anyway. Some might say that is the entire point of swimming for an hour or more in the ocean! That being the case, why would the rain deter anyone from swimming in the first place?
The First Step
As a former competitive swimmer, in some ways, I can relate. The dread of first jumping in the pool, especially at the start of a winter morning practice, is something shared by virtually every swimmer, Olympians included. But just because such a mindset is common does not make it right, nor does it make it helpful. In both cases, the imagined “suffering” is far greater than the reality. Getting wet may be tough at first, but you are planning to be in the water for quite a while anyway. The suffering you imagine fails to live up to the reality you experience.
The more I thought about this reluctance to “dive” into things and how it stems from a fear driven more by our own imagination than reality, I began to see many parallels in business that hold us back as individuals, and as companies.
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Take cold calling, for example. This is something I got to practice in at my very first job, and it was also a core part of how I launched my first business. It is an invaluable skill, but one that irrationally terrifies many. Just like the dread of staring at that cold water in the pool, staring at a yet-to-be-dialed phone is a recipe for paralysis. And yet, what is the worst that can happen? The person you call hangs up on you? Or maybe they yell at you? Even then, all you have to do is push a button and you instead hang up on them. The fear and “suffering” you experience before picking up the phone and making the call is all in your imagination, and it has little if any basis in reality.
The same is true for those difficult feedback conversations. How much easier it seems to focus on what is going well or, barring that, to just gloss over uncomfortable topics entirely. But that ease is nothing more than a mirage. What feels easy at the moment creates far more friction and difficulty in the long run. The imagined suffering of the awkwardness of a single conversation causes too many of us to experience a far more prolonged reality of suffering because we deny our company, and the person in question, the gift of constructive feedback that would set them on a path to improvement.
At an even more fundamental level in the professional world at least, the same idea holds true in making the leap and starting your own business. There are so many great ideas out there. There are far fewer people making that terrifying leap into the cold water of the competitive marketplace to turn those ideas into something real. More times than not the thing holding a person back is staring at them in the mirror. They play out all of the things that could go wrong, all of the reasons not to pursue their dreams and all the reasons the safer and better answer is to stick with the status quo. They imagine all sorts of suffering, and by allowing their imagined suffering to dictate what they do or don’t do in reality, they don’t get to tap into the full positive potential of their imagination in pursuit of those great ideas.
The Giant Leap
If this tendency to imagine suffering is so common and so unhelpful, what is the answer? Perhaps we can’t ever stop our imagination from running ahead of us entirely, but we can be better in how and where we steer it. A perfect illustration of this comes from Amazon’s founder, Jeff Bezos. When trying to decide if he should stay in his cushy and lucrative job or instead “participate in this thing called the Internet,” he decided to think through what would make him suffer more: acting or failing to act.
With this lens, Bezos determined that “if I failed I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried.” It wasn’t that he failed to imagine suffering at all; perhaps we can’t completely stop our minds from doing that. What he did instead was he imagined the suffering of acting as well as of failing to act.
Forging Your Own Path
This two-way imagining of suffering helped Bezos pursue his dream and to his building the most valuable brand in the world. There is no guarantee your own leap will lead to the same result, but the truth is you will never know until you try.
