
Man cannot discover new oceans unless he has the courage to lose sight of the shore
— Andre Gide
The most significant principle of writing is that it is hard, no matter who you are. Writing exposes your self-belief. When you boil it down, it’s your way of saying out loud, “My words matter”. And almost nothing is as powerful as the ability to articulate a story in your world and open up about how it shapes you.
Writing well is like any successful career: You need to recognise when you are playing to win, and you cannot afford to be playing not to lose. Sadly, many people fall into this trap because our lives and our work are treated like pedestals; everyone wants theirs to be the highest.
In an essay about fear and ambition, the author shared a story about a founder struggling to let go of their startup idea. “If this startup fails, I’m going to keep working on some variation for as long as I live until I make it work”, they explained. It’s pretty striking because generally, it is quite a respectable thing to say. But this was different.
Rather than being genuinely admirable determination, it instead seemed as if the founder was holding onto their dreams with a thin and nimble thread, without knowing who was in control of the other end. The founder thought that if he kept working on the idea until one day when it finally worked, his project wouldn’t be a failure—and, importantly, he wouldn’t feel like one.
All of us fall into this pattern at some point. We begin a project, excited by our dream of success and legacy, only to fall into a rut of always thinking it is unpolished and not enough. Ignoring the root cause and being “motivated by fear than vision”.
Put another way: people often make decisions based on the need to avoid pain over their determination to succeed. We encounter fear so great that it controls our thoughts. Small worries escalate quickly and latch onto experiences like a virus. When this happens, our lives become about managing fear.
There are five archetypal fears often underlying people’s work:
Unworthiness - the fear of not being good enough
Death - the fear of eventual insignificance
Uncertainty - the fear of not knowing yourself or where your life is going
Insecurity - the fear of not having enough resources
Rejection - the fear of disapproval, isolation, or letting people down
Playing to win, to live and work satisfactorily is about learning to work with your fears when they come. We don’t often know how much of our work is driven by fear, as our dreams are metaphorical shields acting as a buffer between us and our more difficult thoughts and emotions.
One way to notice your core fears is to see what dreams and thoughts you are overly attached to; once you learn when you’re caught in a dream based on fear, you’ll understand when you need to drop below the surface and work with the rooted down fear.
That way, you can stay connected to your dreams, keep them clean, and know how to move beyond fears and refocus your energy.
Unworthiness
This fear causes our thoughts and ambitions to be about proving ourselves, often to people who care very little, if at all.
Dreams about being worthy are usually about status, such as being a high-ranking employee in a big company, going to a prestigious university, or becoming famous. The issue is things are never as they seem; you are led to prioritise short-term gains and status-signalling over living sustainably. It can also be never-ending because as we achieve more, we compare more. And in most cases, we won’t even notice when we reach our dream, because it will never be enough.
Death
Immortality is the key idea here. The fear of death and insignificance. It centres around how we create immortality projects, having something meaningful that can be remembered long after we’re gone.
Birthday milestones are the usual reminder that time moves in one direction, and this reminder of mortality tends to leave us feeling like we must make an impact—or else we will be forgotten about.
It’s perfectly natural to want to create a legacy, but setbacks can feel threatening and overbearing as a result. Our ambitions are not about trying to carry ourselves through immorality. Either we abandon this desire to be immortal or let reality eventually break through and pierce it.
Uncertainty
This fear is about our need for meaning. We live to make sense of our lives and the future, to have a clear direction and to venture the safest paths.
While creating things as a way of finding meaning can be very motivating, it can make us averse to travelling through important paths and blind to the ways our ideas may not be working. Often, the most interesting paths are the ones discovered through open-ended exploration. But the need for certainty and coherence creates a small box for us to live in, where we’re unwilling to expand our horizons beyond what we already know or can make sense of.
Insecurity
While unworthiness is about not being enough, insecurity is about not having enough. To deal with scarcity, our life becomes about accumulating capital such as money, status, power—or all three.
Insecurities make it easy to lose touch with ourselves and the beauty of the day-to-day meaning in our lives. Things feel like a means to an end, and we become too focused on our destination. As Tim O’Reilly once said:
“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.”
Rejection
Also known as “pliance”, which comes from the field of behavioural psychology as behaviour that is motivated by social consequences.
This fear is about people being successful as a way of not disappointing or letting people down. You become overly concerned with the relational impact of your actions, which is rarely helpful.
The fear of avoiding disapproval is one of the strongest out there. But if we let it control us, we will rarely take risks to be as remarkable as we are capable of. In being too focused on pleasing others, we forget to ask, “Is this what I actually want?” and ultimately live a life that looks nothing like our vision.
In essence, we’re taught to run away from danger, but running will never make them go away. Instead, when you stop running from your fears and turn at them with compassion and kindness, magic happens. They no longer have the power to control you.
The next time you feel caught up, take a moment to dive deeper into your dreams and find the fear that’s lurking under the surface. Notice your urges to pull away and stop to listen to what the fear is telling you. It can never physically hurt you. And who knows, perhaps it is something helplessly calling out for love.
Always what I need to hear. Thank you