A personal journey through the modern workplace

A story about how great talent gets buried under endless administrative tasks.
Jason Walkow
January 20, 2025

We've been chatting with professionals across a few different industries lately to (hopefully) knock loose some of the common pain points and frustrations they experience on a day-to-day basis.

Last week, we chatted with a seasoned financial advisor – someone who shapes the legacies of wealthy families – and we left the call surprised (but not totally surprised) about their workflow. They often spend 3-4 hours every weekend updating client records in their CRM. The irony was palpable as they mentioned a brilliant insight about structuring a multi-generational foundation, one that would likely be forgotten by the time they finished their administrative tasks.

This is the reality for millions of professionals: brilliant minds trapped in the amber of administrative tasks.

According to recent reports like The State of Organizations, the average knowledge worker spends 28% of their time on administrative tasks. A Salesforce study revealed that sales representatives typically update the same information across 4-5 different systems daily. Perhaps most striking, Harvard Business Review's research on peak performance found that high-performing professionals lose up to 40% of their prime creative hours to digital maintenance tasks.

"The future is already here – it's just not evenly distributed."

- William Gibson

We're standing at a crossroads. The technologies that promised to liberate us have, in many ways, become our digital taskmasters. Yet change is possible. We're exploring new paths forward, but more on that another time.

The question isn't whether we can break free from this cycle - it's whether we're ready to imagine a different way of working entirely.

Thanks for reading!

Jason Walkow

Jason Walkow is Head of Design at Plain Sight Ventures. In his free time, Jason enjoys running, eating at the newest spots, and anything coffee-related.

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