My dad encouraged us to fail. Growing up, he would ask us what we failed at that week. If we didn't have somet... — Sara Blakely

My dad encouraged us to fail. Growing up, he would ask us what we failed at that week. If we didn't have something, he would be disappointed. It changed my mindset at an early age that failure is not the outcome, failure is not trying. Don't be afraid to fail.

Author: Sara Blakely

Insight: Most of us grew up hearing the opposite: avoid failure, play it safe, don't embarrass yourself. So the idea of a parent being disappointed when you haven't failed that week sounds almost reckless. But there's something quietly powerful happening in that family dinner conversation. By normalizing failure as something to report and even celebrate, Sara Blakely's dad was doing something radical—he was separating the act of trying from the outcome of trying. The real insight here is that this reframes what failure actually means. It's not about bombing a test or striking out; it's about the safety of inaction. When you haven't tried anything new, haven't taken a swing, haven't risked looking foolish, you've actually failed at the thing that matters most. This distinction changes everything. Suddenly a failed business idea or a botched attempt becomes proof you're living, not proof you're incapable. In our risk-averse world, we often mistake caution for wisdom. We're terrified of visible failure but completely comfortable with the invisible failure of never attempting. The message that stays with you isn't "failure is good"—it's simpler and harder: trying matters more than succeeding. That weekly question, "What did you fail at?" is really asking, "What did you risk this week?"

Trying Matters More Than Succeeding

My dad encouraged us to fail. Growing up, he would ask us what we failed at that week. If we didn't have something, he would be disappointed. It changed my mindset at an early age that failure is not the outcome, failure is not trying. Don't be afraid to fail.

Most of us grew up hearing the opposite: avoid failure, play it safe, don't embarrass yourself. So the idea of a parent being disappointed when you haven't failed that week sounds almost reckless. But there's something quietly powerful happening in that family dinner conversation. By normalizing failure as something to report and even celebrate, Sara Blakely's dad was doing something radical—he was separating the act of trying from the outcome of trying.

The real insight here is that this reframes what failure actually means. It's not about bombing a test or striking out; it's about the safety of inaction. When you haven't tried anything new, haven't taken a swing, haven't risked looking foolish, you've actually failed at the thing that matters most. This distinction changes everything. Suddenly a failed business idea or a botched attempt becomes proof you're living, not proof you're incapable.

In our risk-averse world, we often mistake caution for wisdom. We're terrified of visible failure but completely comfortable with the invisible failure of never attempting. The message that stays with you isn't "failure is good"—it's simpler and harder: trying matters more than succeeding. That weekly question, "What did you fail at?" is really asking, "What did you risk this week?"

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Sara Blakely

Sara Blakely is an American entrepreneur and philanthropist, best known as the founder of Spanx, a revolutionary hosiery and undergarment company she started in 2000. Blakely turned a $5,000 investment into a billion-dollar business, becoming the youngest self-made female billionaire in 2012. She is also known for her commitment to empowering women through various initiatives and her philanthropic efforts.

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