Stress Evolves With Success

Sam Parr and Andrew Wilkinson discuss how entrepreneurial stress evolves through different stages of success, revealing that financial achievement doesn't eliminate stress but rather transforms it.

Key Points:

• Post-Exit Experience (Sam):

  • Significant reduction in stress after selling company to HubSpot
  • Still works long hours but without the weight of payroll responsibility
  • Describes it as "putting on glasses" and seeing a different world
  • Appreciates not having to worry about basic business survival

• Ongoing Entrepreneurial Stress (Andrew):

  • Manages 30+ companies with 600-700 employees
  • Experiences constant stress despite financial security
  • Never felt stress relief due to managing multiple businesses
  • When one company sells, problems in neglected ventures surface
  • Has been "going from stress to stress" for 7-8 years

• Stress Evolution Patterns:

  • Financial security doesn't eliminate stress, just changes its nature
  • Larger operations bring different types of responsibility
  • People problems replace financial problems
  • Control and empire-building come with persistent worry

• COVID Impact on Stress Management:

  • Lost natural stress relief from social interactions
  • Previous routine included cafe work and friend interactions
  • Current remote work environment intensifies stress
  • Lacks "automatic breaks" that helped manage stress levels

• Perspective on Success-Related Stress:

  • Acknowledge these are "great problems" to have
  • But "great problems are still problems"
  • First-world problems remain legitimate concerns
  • Success often means trading one type of stress for another