Staring into the Void
We recently wrapped up our last Third South Capital Offsite for 2025. Harrison wrote his reflections on this, and I recommend you read it for more insights on how the offsite went, what we did on a day-to-day basis, and what a good outcome looks like.
In his article, he mentioned staring into the void…a concept I wanted to expand on here. Where the best time for an offsite is when the team needs to get together, and stare into the void:
"Staring into the void" sounds incredibly profound when Justin and Myles say it. While the phrase traditionally evokes confronting deep meaninglessness or existential despair, I've come to interpret it as: we must allow everyone to reside in discomfort, surface the true points of decision and disagreement, and do our best to come to focused answers.
The phrase comes from Nietzsche: if you gaze for long into an abyss, the abyss gazes also into you." " The void is the uncomfortable and unspoken truths. It’s the nagging feeling that your strategy is failing, the quiet dread that you don’t trust the numbers, or the deep-seated fear that your team isn’t truly aligned. Staring into the void means looking at these questions head on and solving them.
You know the feeling. You're in a meeting and everyone is talking around the same central, unspoken fear. The team projects an image of competence, but underneath, those questions haunt you. You can try to address them in a normal meeting, but it's like trying to have a serious conversation at a noisy party. The daily distractions and the pressure to maintain the status quo make it nearly impossible.
This is why offsites are necessary. It’s the deliberate choice to stop averting your gaze from the abyss. You sit in a quiet room, with no distractions, and you give the void your undivided attention. In that space, you feel the collective unease, and for the first time, you can acknowledge the problems together. This is a time to reflect on what you want, why, and how you should go about getting it.
This is the moment when the void “gazes back.” You realize the very thing you were avoiding has been quietly shaping your work and your team all along. An offsite provides the courage to face that void, and in that shared act, you find a new sense of purpose built on honesty and true alignment.