Failure, Comparison, and The Bitter B Trap

EPISODE 250 OF THE HINT OF HUSTLE PODCAST

You’re not failing. But I’d bet good money you walk around feeling like you are.

I’m not talking about the obvious kind of failure… a flopped launch, a missed goal, a pitch that got rejected… but rather the quieter kind of failure. The low-grade hum of “I should be further along by now.” The spiral that starts the second something doesn’t go the way you planned. The way you measure your right-now self against the highlight reel of your past self AND the fantasy version of your future self, simultaneously, which means no matter what you do, present-tense you is always losing. That’s the Bitter B trap. And in this episode, I’m going deep on it.

I get into why driven, high-achieving leaders are the most susceptible to this pattern, how the questions you ask yourself after something goes wrong are either pulling you up or drowning you, and the one question I’ve used for fifteen years to get out of any hard season, in business, in health, in parenting.

I also get personal about my dad’s health and what it’s teaching me about how I want to show up in my own body. And toward the end, there’s a mirror I’m going to ask you to hold up around the clients you keep complaining about. Heads up on that one!

By the end of this episode, you’ll know exactly what’s keeping you stuck in the feeling of failure, and have a simple shift to start moving out of it today.

3 BIG IDEAS FROM THIS EPISODE:

1. The Feeling of Failure Stems from Comparison: You’re measuring your present self against a romanticized memory of your past performance AND an idealized vision of your future self, at the same time. That gap is the thief, not the circumstances, not the market, not the people around you. Until you see the comparison for what it is, you’ll keep sinking into it

2. The Way You Talk To Yourself Accelerates or Suffocates Success: When something goes wrong, most of us default to “I should have done X” or “why did I even try this again?” Those aren’t just unpleasant thoughts, they actively stifle your ability to move forward. There is no productive answer at the end of “I should have.” What you need instead are expansive questions, the kind that force your brain to look upward. The one I’ve used for fifteen years is simple: what opportunity does this create? Write it down and use it.

3. The Bitter B Version of You Will Never Get You to Your Goals: We all have a version of ourselves that comes out when we’re stuck, behind, or disappointed. She blames the past, the market, the bad investment, the difficult client. She might even be right about some of it. But being right doesn’t move you forward. The ones killing it in business (and in the gym) are not spending their energy in that place. Even when they find themselves in the same situation, they have a different experience because of their internal conversation. You get to choose which one you operate from.

EPISODE LINKS & RESOURCES:

📚 Failing Forward by John Maxwell, available wherever books are sold

🎧 Hint of Hustle episode # on asking better questions: 152: Make this Shift With Your Language to Operate Like 7 Figure CEO

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