Five Core Fears That Warp Ambition

How to recognize when you’re playing not-to-lose, instead of to win

Midjourney prompt: Create a watercolor illustration about fear and dreams

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.

Another issue with worthiness projects is that they’re never-ending. As we achieve more, we tend to compare ourselves to more successful people. So even if we achieve a dream, it doesn’t necessarily lead to lasting satisfaction. What we consider “enough” keeps changing, and we end up chasing a destination that’s always just out of reach.

Immortality Projects

Our second archetype is the immortality project, which is driven by the fear of death and insignificance. This term was originally coined by Ernest Becker in his 1973 book, The Denial of Death, and points toward the ways we attempt to cheat death by achieving something so meaningful that we’re remembered long after we’re gone. 

I often see the quest for immortality come up around milestone birthdays. When we turn 30, 40, 50, or 60, it reminds us that time only moves in one direction and that our days are ultimately numbered. This raised awareness of mortality often leads to the feeling that we need to make an impact—or else risk disappearing completely when we take our last breath.

While it’s natural to want to create a legacy, when we use our work to try and overcome our fear of death, setbacks feel existentially threatening. Moreover, no project is ultimately durable enough to carry the weight of our dreams of immortality. Projects change and often fail. Either we let go of this illusion of immortality, or reality breaks through and eventually pierces it.

Coherence Projects

Our third archetype is the coherence project, which is driven by the fear of uncertainty and the need for meaning. A coherence project helps us make sense of our life in some way, and without it, we’re unsure of who we are or where we’re going.

Sometimes, coherence projects are about making sense of the past. As an example, someone who left the partner track at McKinsey to start a company might hold tightly to their startup dream, because it makes sense of the risk they’ve taken and what they’ve given up. Similarly, I often see founders in the mental health space create companies as a way to find meaning in their own struggles. While this can be highly motivating, it can also blind them to ways their ideas may not be working.

Coherence projects can also be about making sense of the future. I often see this when people are navigating a career transition. They grab onto the first pragmatic idea they come across, because being without a clear sense of direction feels too unbearable

This is problematic, because the most interesting paths are often only discovered through open-ended exploration. In the words of the author André Gide:

“Man cannot discover new oceans unless he has the courage to lose sight of the shore.” 

When we’re caught in the need for coherence, we end up living small—unwilling to expand our horizon beyond what is already known or what logically makes sense.

Security Projects

Our fourth archetype is the security project, which is driven by the fear of scarcity—of not having enough. To deal with this fear, our projects become primarily about the accumulation of capital: money, status, or power.

When this happens, we tend to lose touch with the day-to-day meaning in our work. Instead, our projects begin to feel instrumental, like a means to an end. We become hyper-focused on the destination and fail to notice the vitality draining out of the journey itself.

Don’t get me wrong—in the modern world, we need money to live and to bring our projects to life. However, capital accumulation is not typically a meaningful end in itself. 

In the words of Tim O’Reilly: 

“Money is like gasoline during a road trip. You don’t want to run out of gas on your trip, but you’re not doing a tour of gas stations.”

Moreover, if your primary motivation is security, then that’s also what you’ll get from your team. It’s hard to connect others to a larger mission if you aren’t connected to it yourself. As a result, you end up with a band of mercenaries, instead of a team with a deeper sense of organizational purpose.

Pliance Projects

Our fifth and final archetype is the pliance project, which is driven by the fear of rejection. The term “pliance” comes from behavioral psychology, and describes behavior that is primarily motivated by social consequences. 

When this fear shows up, our projects become about not wanting to let people down. This is a common issue for first-time founders, who often overly worry about failing and disappointing their team and investors. I’m not necessarily advocating callousness, but being overly concerned with the relational impact of failure is rarely helpful.

This fear can also lead CEOs to avoid making needed changes during times of transition. A business line may clearly not be working, but the CEO hesitates on setting a new direction, as it would mean letting go of that division’s customers and employees.

If we spend our days trying to avoid disapproval, we won’t grow or take the risks necessary to build something remarkable. Even worse, if we’re too focused on pleasing others, we may forget to ask, “Is this what I actually want?” Ultimately, we may end up with a company that looks like nothing like our original vision and that we don’t really enjoy running.

Kissing the Dragon: Working With Fear

So how can we reconnect with vision when our projects have become driven by fear?

From an ACT perspective, fear itself is not the problem. It’s perfectly normal and valid to experience fears around death, unworthiness, uncertainty, scarcity, and rejection in the course of one’s work. Rather, the problem is that when these fears get big, our focus shifts toward managing the fear and we lose touch with what we ultimately care about. 

The answer, then, is to learn to hold our fears in a more flexible way, rather than putting them in the driver’s seat and letting them run our projects. We don’t want to try and suppress our fears—that just gives them more power. Instead, if we can make space for fear when it arises, over time we can learn to experience it without needing to manage or control it.

One metaphor I like for this process is “kissing the dragon.” We’re taught to run away from dragons, but when we’re brave enough to kiss them—to turn toward our fears and meet them with kindness—something magical happens. 

In the words of the German poet Rilke:

“Perhaps all the dragons in our lives are princesses who are only waiting to see us act, just once, with beauty and courage. Perhaps everything that frightens us is, in its deepest essence, something helpless that wants our love.”

Kissing the dragon won’t necessarily make the fear go away. However, when we stop running from our fears and instead turn toward them with compassion, they no longer have the power to control us.

So if you’re feeling caught in a tightly-held dream, here’s the invitation: Take a few moments to drop down and notice any fear that’s lurking beneath the surface. 

What does it feel like when you contact it? Do you notice the urge to pull away? What might this fear have to tell you about what you find important? This kind of inquiry is the first step in beginning to open up fully to the fear that’s driving you. 

When we’re able to do this, our projects no longer need to be shields against our fear. They can become a source of meaning, creativity, and purpose—and thus a source of real fulfillment. 

Author bio: Casey Rosengren is a founder and executive coach based in New York. If you’d like to learn more about ACT and values-oriented coaching, drop him a note.

Like this?
Become a subscriber.

Subscribe →

Or, learn more.

Read this next:

No Small Plans

How to Find Freedom Under Pressure

A founder’s guide to liberation amid stress and uncertainty

1 Sep 5, 2023 by Casey Rosengren

No Small Plans

The Art of Subtle Influence

How to lead when you don’t have control

Aug 1, 2023 by Casey Rosengren

No Small Plans

No Margin, No Mission

The ethical imperative to make a profit

1 Nov 8, 2023 by Casey Rosengren

The Sunday Digest

How AI Works, Crypto’s Prophet Speaks, ChatGPT for Radical Self-betterment, and More

Everything we published this week

Feb 4, 2024

Napkin Math

Profit, Power, and the Vision Pro

Will Apple’s new headset change everything?

5 Feb 6, 2024 by Evan Armstrong

Thanks for rating this post—join the conversation by commenting below.


You need to login before you can comment.
Don't have an account? Sign up!
@Haberjr 12 months ago

The essence of these fears is that they are thoughts. The five labels make it unnecessarily complicated. Labels take you further away from what is really happening. Psychological fears are movements of thoughts. See clearly that these are thoughts and you have stepped out of the thoughts.

@alex.m.beaulieu 12 months ago

I can agree with the last comment, but it's okay to engage with them as constructs if that's where you are! I loved this because it clearly illustrates for us what really drives our motivations as people. Thank you for it :)

Tintin 12 months ago

Good points of view here.

Every smart person you know is reading this newsletter

Get one actionable essay a day on AI, tech, and personal development


Already a subscriber? Login