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