In this engaging discussion, Sarah Douglass, founder of Wise Owl Outfitters, shares her journey of intentional living after selling her successful e-commerce business. She opens up about the emotional void that followed her financial success and her struggle to resist the urge to find immediate productivity. Sarah emphasizes the importance of rediscovering her identity beyond entrepreneurship and explores the delicate balance of motherhood and ambition. Her insights on personal growth and the search for authentic fulfillment are both inspiring and relatable.
Achieving financial freedom can lead to an unexpected void, prompting a deep search for personal fulfillment beyond external success.
Sarah Douglass's journey highlights the importance of self-discovery and mindfulness in defining true happiness after significant life changes.
Navigating motherhood while maintaining entrepreneurial ambitions emphasizes the need for community support during personal growth and transitions.
Deep dives
The Pursuit of Contentment
Achieving financial freedom through the sale of a successful business can lead to unexpected challenges, such as the search for personal contentment. After selling her e-commerce brand, Sarah Douglas found herself struggling with the desire to create impact while also seeking happiness in her current state. This internal conflict prompted her to reflect on the concept of fulfillment, questioning the societal notion of success and the external milestones she once chased. Ultimately, her journey illustrates the complexity of balancing ambition with the need for personal satisfaction.
Transitioning from Entrepreneurship
The experience of selling a business can leave a profound void, as entrepreneurs often tie their identity to their work. Sarah initially found herself overwhelmed after her exit, grappling with feelings of exhaustion and a lack of direction. The shift from being consumed by her startup to having more freedom led to a subtle yet significant change in her priorities and motivations. Instead of simply continuing to work for financial gain, she desired to engage in a more meaningful way that aligned with her values and sense of purpose.
Redefining Success Post-Exit
Sarah's story emphasizes the importance of self-discovery after significant life changes, particularly in understanding what truly brings happiness. Post-exit, she experienced burnout and had to confront the perceived emptiness that can accompany the completion of long-sought goals. Despite achieving everything she had once thought would fulfill her, she realized that external success did not automatically equate to internal satisfaction. Through exploration and reflection, she began to recognize that fulfillment may stem from personal growth and mindfulness, rather than merely pursuing societal definitions of success.
The Role of Relationships in Personal Growth
Navigating motherhood while running a business added another layer of complexity to Sarah's journey, as she sought to provide for her children while maintaining her ambitions. Balancing responsibilities proved challenging, but it also catalyzed her growth as a person and a mother. Sarah acknowledges the importance of surrounding oneself with supportive individuals who share similar experiences, highlighting the impact of community on personal development. This emphasis on relationships speaks to the value of shared understanding and encouragement in overcoming life’s transitions and challenges.
Embracing a New Chapter
As Sarah contemplates her future, she grapples with the notion of 'what's next' while focusing on the importance of intentional living. Rather than rushing into a new venture out of a sense of obligation, she recognizes the need to assess her motivations and ensure they align with her values. Sarah also emphasizes the significance of finding purpose in future endeavors, rather than merely seeking financial success, acknowledging that true fulfillment arises from contributions that positively impact others. This shift in perspective reflects the transformative power of self-awareness and clarity in defining one's path after exiting a business.
My dear friend Sarah Douglass sold her incredibly successful e-commerce business three years ago, achieving the financial freedom she had always dreamed of.
But soon after, she found herself grappling with a new challenge: balancing her newfound success with an ever-deepening desire for contentment and a powerful drive to create impact.
In today’s conversation, Sarah shares her journey with disarming authenticity, opening up about her deepest struggles.
We explore the unexpected void left by success, the difficulty of resisting the urge to immediately start something new just to feel productive, and her shift from chasing external milestones to embracing intentional living—rediscovering who she is as a whole being, not just as an entrepreneur.
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TIME STAMPS:
00:00:00: Introduction and greetings
00:01:04: Sarah's business journey beginnings (Music school)
00:01:39: Transition to selling online (Discovery at dinner)
00:02:04: Starting with camping gear (Wise Owl Outfitters)
00:02:56: Challenges and operations (Traveling to China)
00:03:40: Balancing family and business (Moving and kids)
00:04:23: Working with her husband
00:05:21: Husband's role and career shift (Becoming a painter)
00:04:37: Decision to sell the business
00:05:00: Influences and reasons for selling
00:07:01: Financial freedom and exiting strategy
00:08:16: The selling process (Timeline and logistics)
00:09:56: Reflections on the buyer's bankruptcy
00:11:06: Emotional impact of selling
00:12:10: Post-sale challenges and burnout
00:13:23: Realizations and health impact
00:14:40: Personal and existential reflections
00:16:55: Seeking and understanding contentment
00:18:37: Advice on spirituality and life direction
00:19:06: Initial thoughts on spirituality and personal development
00:19:23: Exploring different avenues for growth
00:19:46: Impact of personal coaching and physical health
00:20:36: Reflection on life's purpose post-exit
00:21:32: Evaluating new opportunities and the allure of starting new businesses
00:25:00: Importance of being helpful to others
00:27:18: Finding balance in life and prioritizing oneself
00:27:50: Balancing motherhood and business
00:32:17: Handling wealth and teaching children about money
00:34:42: Shifts in business motivation without the need for money
00:38:17: Importance of having a supportive team
00:39:08: Pursuing new, exciting projects
00:40:02: Balancing current business with new ventures
00:40:26: Benefits of taking extended trips
00:42:04: Discovering oneself through new experiences
00:46:04: Reflections on legacy and impact on others
00:48:02: Interpretation of "Stay hungry, stay foolish"
00:51:03: Struggles of balancing business and family as a woman
00:56:06: Comparison of post-exit life to athletes' career transitions
00:56:38: Feeling lonely during the process
00:56:52: Searching for information online
00:57:15: Conclusion and thank you
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