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The Dark Side of Solopreneurship: 7 Habits That Drive Success

Marshall Hargrave
8 min readDec 27, 2024

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The solopreneur dream is alluring: complete autonomy, unlimited income potential, and the freedom to work from anywhere.

No bosses, no office politics, just pure entrepreneurial independence.

But beneath the polished surface of Instagram-worthy workspaces and “laptop lifestyle” marketing lies a darker truth: successful solopreneurship demands a set of unglamorous habits that few discuss openly.

Successful solopreneurship isn’t about:

  • Working from exotic beaches
  • Rolling out of bed at noon
  • Building passive income overnight
  • Achieving instant work-life balance

Instead, it’s about developing rigid disciplines and unsexy habits that separate sustainable success from short-lived experiments.

1. Treat Yourself Like an Employee From 9 to 5

The transition from structured employment to solopreneurship creates an immediate paradox: complete freedom often leads to complete chaos. While the ability to work anytime might seem liberating, it frequently results in diminished productivity and scattered focus.

The Productivity Death Spiral

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Marshall Hargrave
Marshall Hargrave

Written by Marshall Hargrave

Serial entrepreneur. Finance, startups, investing. Catalyst-focused, event-driven. Hip-hop vigilante. On the quest for the best hot chicken.

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