The Bottom Line

Decisions That Made Me: Dana Denis-Smith (Obelisk Support, CEO)

Jan 6, 2025
Dana Denis-Smith, CEO of Obelisk Support, shares her inspiring journey from an unfulfilling legal career to entrepreneurial success. A transformative trek through the Himalayas ignited her passion to support freelance lawyers, particularly mothers seeking flexible work. She discusses balancing career ambitions with family life, the emotional toll of employment law, and her mission to empower women in the workforce. Join her as she unveils the complexities of the wellness industry and the drive for justice in a changing professional landscape.
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ANECDOTE

From Journalism to Law

  • Dana Denis-Smith's first career was journalism before she transitioned into law, influenced by her husband's legal studies.
  • She found the long, unpredictable hours of corporate law overbearing and felt like a cog in a machine, prompting her to seek a more purposeful career.
ANECDOTE

Himalayan Epiphany

  • A trip to the Himalayas provided Denis-Smith with clarity about her career dissatisfaction.
  • The experience inspired her to leave her law firm job, prioritizing purpose over financial stability.
ANECDOTE

Entrepreneurial Journey

  • After leaving law, Denis-Smith started a political risk company focused on emerging markets, leveraging her diverse background.
  • Another trip to India inspired her to create Obelisk Support, a platform connecting businesses with freelance lawyers, many of whom are mothers seeking flexible work arrangements.
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