Starting from nothing requires courage. But there is another kind of courage we discuss less often: Leaving something that works.
Failure can make a decision for us. When the money is gone, the customers are not coming or the opportunity has clearly closed, moving on may still be painful, but the evidence is visible.
Success is more complicated. It gives us reasons to remain. It gives us recognition, income, identity, familiarity and proof that we know what we are doing. Other people can see why we built it. They may not understand why we would loosen our grip on it.
Sara Blakely founded Spanx in 2000 with $5,000 in savings.
She retained complete ownership for more than two decades, building it into a global business without outside investment. In 2021, Blackstone acquired a majority stake at a valuation of $1.2 billion.
Blakely retained a significant stake and became executive chairwoman. She did not abandon Spanx, she gave up majority control of the company she had created and personally carried for 21 years.
From the outside, a transaction like that looks like an unqualified victory. Blakely has described the transition differently. She has spoken about mourning the loss of control and the emotional difficulty of separating herself from a company that had occupied so much of her life and mental space.
This is the part of success that receives less attention.
We celebrate the sale but we rarely discuss what it means for a founder to wake up and realize that the organization she created no longer belongs to her in quite the same way.
We ask, “What are you doing next?”
We do not always allow enough time for the founder to understand who she is without the role that previously answered that question.
Blakely also began again with Sneex, a footwear company attempting to combine the appearance of a high heel with the comfort of a sneaker.
She was no longer an unknown founder cutting the feet off a pair of tights in her apartment. She had money, relationships, experience and a recognizable name. But beginning again still required becoming a beginner.
She spent years trying to solve the product problem. Factories declined the work. Some stopped working with her. At one point, she considered abandoning the project because the result was better, but not sufficiently better to justify launching another company around it.
Experience did not remove uncertainty. Previous success did not guarantee that the new idea would work.
That may be one of the quieter challenges of a second act.
The first time, you have little reputation to protect. The next time, the world expects you to repeat yourself successfully.
But growth does not always ask us to repeat what worked. Sometimes it asks us to release it.
This does not mean every successful founder should sell a company or begin another one.
It does not mean discomfort is always evidence that it is time to leave.
There are seasons in which the courageous act is to remain, repair and continue building. But there are also seasons in which something can still be working while no longer requiring the same version of you.
That is harder to explain.
Nothing has collapsed. The opportunity has not disappeared. You may even be good at the work. But a persistent question begins to emerge:
What else could my life contain if this no longer occupied most of it?
Leaving something that works is not necessarily a rejection of what you built. It can be an acknowledgement that it has completed one of its assignments in your life. You can remain connected to what you created without remaining responsible for every part of it. You can be grateful for the identity it gave you while becoming curious about who you might be without it.
Starting Spanx required Blakely to believe in an idea before there was evidence that it would work. Releasing majority control required a different belief: that the success she had built did not have to remain the only proof of who she was.
Perhaps that is why leaving something successful can require more courage than leaving something that has failed. Failure asks you to accept that something is over. Success asks you to decide whether it should still define you.
Not all new chapters begin because the old one collapsed. Some begin when you accept that what you built can continue without occupying all of you, and that you are allowed to discover what else you can build.
The courage to start says, “I believe I can make this work.”
The courage to release it says, “I believe I can build again.”
Until the next note,
– STB
Notes with STB | A content series exploring mindset, money and business.
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