Five Core Fears That Warp Ambition

Last year, I was chatting with a struggling founder who said something that stuck out to me:

“If this startup fails, I’m going to keep working on some variation of the idea for as long as I live until I make it work.” 

At first glance, this may appear laudable. In startup culture, we mythologize founders who were rejected by investors and then went on to build significant companies. Yet while perseverance is important, this felt different.

I got the sense that this founder was hanging on to his idea like a life preserver. If he kept working on the idea and one day it worked, then the project wouldn’t really have failed. More importantly, he wouldn’t feel like a failure.

This is a pattern that many of us fall into at times. We start a project because we’re excited by our dream of what it might become, and then fall into a rut where we become more motivated by fear than by vision. We stop playing to win, and start playing not-to-lose.

This happens when we contact a fear that feels so big it overwhelms us. When small worries arise, we may be able to experience them while staying connected to meaning. However, when something touches a core fear, our lives and work can become about managing that fear.

As a coach and former founder, there are five archetypal fears that I often see underlying people’s work:

• Unworthiness - the fear of not being good enough
• Death - the fear of insignificance and disappearance
• Uncertainty - the fear of not knowing who one is or where one’s life is going
• Insecurity - the fear of not having enough resources
• Rejection - the fear of isolation or letting people down

If you can learn to recognize and work with these fears when they arise, you’ll be able to stay connected to your dreams, even in the face of perceived threat.

Recognizing Fear

The more psychologically salient a fear, the more likely we are to avoid or suppress it. As a result, we may not be aware how much fear is driving our work.

One way to catch core fears is to notice where in your life you are overly-attached to a dream. Dreams can serve as a metaphorical shield, buffering us from thoughts and feelings that we find difficult to tolerate (fear, shame, etc.). 

If you pay attention to your most tightly held ambitions, that can point you toward what you’re most afraid of.

Each of the core fears above leads to a different type of stuck dream:

• Unworthiness → Worthiness Projects
• Death → Immortality Projects
• Uncertainty → Coherence Projects
• Scarcity → Security Projects
• Rejection → Pliance Projects

When you recognize that you’re caught in one of these fear-based dreams, it’s an invitation to drop below the surface and work directly with the underlying fear, so you can move beyond it and refocus your energy on what really matters.

Let’s explore each of these archetypes individually so we can better recognize them when they show up:

Worthiness Projects

Our first archetype is the worthiness project, which is driven by the fear of being “not enough.” When caught in this fear, our projects and goals become about trying to prove our worth by achieving more.

This fear often leads to dreams associated with status, such as becoming the CEO of a major company, getting into YC, or becoming famous. On the surface, these dreams appear to be about success, but underneath they are about managing a deep-seated fear of being “unworthy.”

One issue with worthiness projects is that they can lead us to prioritize short-term gains over long-term goals. We may focus our efforts on short-term status signals—like getting press coverage, speaking at conferences, or networking with VCs—and not on actually building a sustainable business.