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The F’n Dream Killers Featured

The F’n Dream Killers "Shark diving in South Florida"

Fear and failure—they’re not the same thing, but they certainly swing in the same circles. Fear is a primal emotion triggered by the thought that someone or something is risky or dangerous and could likely cause us harm or pain. While our fears can be healthy, they’re often not proportionate to the threats we face. As an example:

            Your odds of being attacked by a shark are 1 in 3.75 million.4 Your odds of dying in a car crash are 1 in 103.5 We want to know: What are you more afraid of?

            (We’re more afraid of sharks, too.)

            Our fears can, clearly, also be irrational, yet they’re there to inform us that the possibility of failure is certain. Failure is, after all, our shared number one fear.

            When we talk about failure, we often think of catastrophic loss, though there are many shades of failure. It can be felt when we’re embarrassed, make mistakes or missteps, or when we experience disappointments or setbacks. For example:           

  • Your family makes the final rounds of an adoption process and isn’t selected.
  • You poured hours into a proposal, and it didn’t win the bid.
  • You spent a weekend working to organize your house, and you didn’t make it past the garage.
  • You “replied all” to an email meant for just one reader (and what you wrote should never have been expressed in an email).

            The dictionary defines failure broadly as the “lack of success.” In this case, there are probably failure moments we encounter every day. What’s key, though, is how you think about fears and failures, which comes down to how you choose to experience them. This will inevitably determine your relationship with them and, more important, the outcome.


Our fears are, most definitely, real. So is the power of our attention in the moments when we feel them. When you’re experiencing the sensations that signal you’re afraid, don’t let them hijack your focus and consume you. Rather, employ strategies to allow you to manage them, rationalize them, and rightsize them. This will allow you to work through them on your Bet on You journey, so you experience the success that awaits you on the other side of what scares you.

Strategy 1: Save Your “Perfect” for Never

The fear of imperfection can invoke procrastination at best, and stop a dream in its track at worst. We’ve met self-proclaimed perfectionists who:

  • Were afraid to apply for a role because they needed just one more experience.
  • Didn’t buy their first home because they couldn’t find the exact, right one.
  • Never launched their Etsy business because their work still wasn’t good enough.

            We’ve talked about goal attainment throughout this book as a series of steps that involve missteps, mistakes, experiments and tries, starts and stops, and step backs to step forward. Betting on you isn’t a neat, straightforward, perfect process. If you’re a perfectionist, you may fear risk-taking, because doing nothing could seem like a better idea than doing something that may not turn out right—by “right,” we mean by your often-too-high, and sometimes impossible-to-meet, standards.

            When it comes to betting on you, abandon your perfectionist goals. They’re futile and unrealistic. Instead, plan and prepare for the goals you’ve identified for yourself in your kaleidoscope with reality in mind. Strive for good enough. We have a saying here at Lead Star: Our good enough is pretty damn great. This forces us to take action when we feel that we’re applying a perfectionist standard to something that just can’t be perfected. And if we feel there’s a chance that we’ll learn more in our journey and further perfect the idea along the way? Then, hey, great, we’ll apply an iterative development mindset. Good enough is a reliable gateway to the path to greatness.

            There will be things you’re afraid of on your journey. There will be areas and activities that you won’t be good at. Uncertainty can be maddening. Be aware, but don’t fear imperfection.

If you still feel the need to try to perfect something, perfect your response to managing your perfectionist tendencies—the effort you invest in knowing how to squelch them will give you the courage to move through them.

Strategy 2: War-Game Your Fears

We’re Sun Tzu devotees. If you’re not familiar with The Art of War, it’s never too late to pick up a copy and absorb the wisdom and philosophies of this ancient Chinese general whose guidance is applicable to warfighting, business, and everything in between. His work reminds us that: “If you know the enemy and know yourself, you need not fear the result of a hundred battles.”

            We talked about self-awareness in chapter two, the “know yourself” aspect of this quote. But what about your fears? How well do you know those enemies?

            It’s near impossible to conquer the unknown. On your Bet on You journey, get to the brass tacks of it, make a list of what scares you, what you’re nervous about, and how the emotion of uncertainty makes you feel. Know that it’s common to feel everything that you’ve identified; we’ve yet to meet any warrior who doesn’t fight scared.

            Fear is healthy; familiarity with fears allows you to rightsize them to ensure you’re not overblowing them. Your fears also are an indicator that you respect the challenge that you’re up against, aren’t too cocky or confident in the face of it, and that your direct action is needed to move through them.

            Unchecked fears, though, aren’t healthy, especially when they run rampant. What’s usually behind these are complex feelings of worry, insecurity, lack of worthiness, or long-held doubts (often planted by someone else, but long accepted by you without question).

            If you don’t sort and confront what you’re afraid of, your fears can amplify and easily rule your life since the feelings build on how often you experience them. This is called potentiation and can manifest in many unproductive, unhelpful ways. For example, if you’re worried about losing your job, even the most uneventful meeting with your boss can trigger a fear response. Or if you’re nervous about the new selling method you’re using in your sales role, one lukewarm comment from a customer about your product—not your method—can send you sideways.

            Once you’ve got your fears named, war-game them. Like Billie Jean King did, imagine how you’ll handle them when you meet them, all of them. See yourself navigating them, stepping beyond them, and experiencing success despite them. The mental war games make you feel rehearsed and prepared. Businesses do this all the time in the continuity of operations planning. We need to do this in our life.

            Beyond the benefit of planning how to step through your fears, war-gaming allows you to set your boundaries, the lines you won’t cross on your journey, because you’ve had a chance to visualize what your fears and potential fails can look like. Some fails you’ll be fine with absorbing. Then there will be times in your thought experiments when you’ll realize other fails you just can’t accept.

            In the military, we call this establishing go-no-go criteria. In other words, if we can push beyond our fears and find ourselves on our journey, our go-no-go criteria is there to govern whether we should persist (go!), or relent (no go!).

            When we started our business, having go-no-go criteria allowed us to test both the viability and sustainability of our business. In the early years, if we didn’t meet certain revenue targets, we knew we’d need to close up shop because we wouldn’t last. Later, when we were exceeding targets and working around the clock to meet client demands, we established new go-no-go criteria to meet is-it-worth-it? goals, which were more related to the idea that if we lost our life to our business, then what’s the point of it all?

            Your go-no-go criteria helps you understand when you need to evoke courage, informs you of when you need to heighten and sustain effort, and often indicates when you need to yield

because success, at least the way you envisioned, isn’t going to be achieved.

            And when the latter happens, success can’t be achieved, you need to employ the next strategy because fails hurt. There’s no way around it. And, paradoxically, fails can be the greatest gifts we receive in life because of all the learning and growth they offer that gives us an opportunity to build resiliency. The hard thing, though, when you’re failing, is believing in the value of the experience so much so that you lean into it by telling yourself, “My future self is going to be so grateful for all the suffering I’m enduring right now.”

Strategy 3: Plan for Fails

We celebrate fails when we’re exercising. Broken down, torn muscles are the typical precursor to stronger, more durable ones. We can value this notion as it relates to life in the gym, but it’s a concept really difficult to put into practice in the rest of our lives. In other words, push our life to failure points so we can grow.

            No one likes to fail. Yet, there’s so much good that can come from a bad situation. It’s like the Japanese art of Kintsugi. It’s the process in which broken pottery is restored by mending the pieces together with lacquer that’s mixed with powdered gold, silver, or any other fine element. It’s a beautiful art form born from imperfection. In fact, it’s the near-perfect symbol of resilience.

            We want you to prepare for fails, plan for them to happen. Not plan for specific events to fail, like “I’m going to blow this client meeting on Tuesday.” That’d be defeatist. You should approach your client meeting prepared, rehearsed, and confident that you can crush it. If it doesn’t work out your way, though, you need to have a plan of attack on what you’ll do so that fails don’t influence future successes.

            A simple fail plan is to learn, adapt, and apply.

            Simply stated, that is. Like anything in life, it’s easier said than done.

            Failure that’s repeated is foolish; that means learning didn’t happen. You had the experience but didn’t get the benefit from the mistake. Next, learning without changing is pointless; what’s the point of knowing better and not adapting? Changing without application means you miss out on the opportunity to express growth from the experience.

            One fail shouldn’t influence another. If you had a bad meeting, you had a bad meeting—learn, adapt, apply and make the next meeting better. There’s no need to create and carry your baggage around with you. Also, don’t be tempted to associate unconnected fails. One bad meeting followed by a flat tire the next day doesn’t mean that the world is conspiring against you. These are two separate, unrelated situations.

            Yet, in the same breath, if you’re noticing repeated mistakes, missteps, and small warning signs related to a specific area of your life, like your past several meetings haven’t gone as planned, then perhaps it’s time to pay attention. The rare, catastrophic, unrecoverable failure usually comes with plenty of warning signs. When you see them, you have options—you can:

  • Accelerate your learning, adapting, and applying.
  • Pivot with or without grace.
  • Do nothing and risk going down with the ship.

            Notice that none of these options include placing blame. That’s not leadership behavior and, besides, excuses only satisfy those who give them.

            It’s a delicate walk, we know, to understand when to persist and when to relent. Yet, the more attuned and accountable you are to your missteps, the better presence and judgment you can exercise in those moments when a good, solid decision is needed. Like, the decision to quit.


Adaptation from BET ON YOU: How to Win with Risk (2022) by Angie Morgan Witkowski is an executive, leadership, and life coach and NY Times best-selling author of business books like SPARK: How to Lead Yourself and Others to Greater (2017), and Leading from the Front: No-Excuse Leadership Tactics For Women (2006).

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