What If... ?

What If... ?

Interesting start to a question, isn’t it?

How one goes on to complete it can, to state the obvious, lead a person into an optimistic, hopeful, expansive reverie or more commonly down the slippery slope to feeling badly about oneself and one’s prospects.

Consider this scenario. An experienced professional trader, with pedigree, track record and a robust strategy decides to take the leap to make their own mark.

Emboldened with years of experience, contacts, momentum and at the same time acutely aware of the ticking clock (we’re not going to live forever), the inner question If not now, then when? rings louder than the conventional path of an investment professional.

And so one takes the leap. Not so much into the “unknown” as this type of individual has likely taken time to create a plan, “a controlled exit” with mentors, advisors and resources in place.

And then at some point in time, whether right away or a few weeks or months thereafter, comes the lived experience. A visceral, unsettled feeling that initially shows up as mild doubt, but over time grows into a constant underlying hum that chips away at one’s steadfastness.

I had a conversation with such an individual recently who shared with me the following “I wake up at 3am and wonder if I’m really cut out for this.”

In the dead of night, the mind and the body restless. Plagued with the question of what if… What if I let people down? What if I let myself down?

What’s Really Going On

Sleepless nights in circumstances such as these are rarely about lack of knowledge. We are in the information age after all.

They are in fact about deeply held fears and beliefs, some of which have lain dormant for years. Only now triggered by ‘reality’ do they find their way to the surface in the form of restlessness and anxiety.

The weight of carrying it alone, the fear of failure, the need to control the outcome. All of these intensify the cycle. And no matter how one rationalises, the body doesn’t believe the hype. And so, it keeps you awake.

In finance, and especially fund management this can surface at any point in a career, but most often at transitions:

• Getting a promotion

• Starting a fund

• Leaving a firm to go solo

• Scaling up risk

• … even retiring

Moments where you step outside the safety net.

The more qualified you are, the more experience you have, the more exposed you can feel. Particularly when starting out, because every decision now has your name on it. Every outcome is yours to bear.

Under the Hood

So what is going on?

If you strip it back, these “what if” moments aren’t really about markets. They are about us.

Our deeply held thoughts and beliefs about ourselves. Beliefs that go to the heart of the matter. Simply put. Am I good enough?

They strike at our sense of security and our place in the world. Trying to address needs that emanate from childhood, which to this day drive our thoughts, actions and reactions unconsciously.

Their footprints show up as:

• Replaying decisions and conversations

• Second guessing ourselves

• Pushing hard, overworking, not trusting

And at the base of it all, the primal fears of failure and rejection and the consequences that flow:

If I don’t pull this off what will it mean for me, my family? What will they think of me, my credibility, my reputation? Will I be loved…? What if…?

The older we get, the less we consciously entertain these questions. Why? Perhaps we are too busy. Perhaps it feels indulgent. Or perhaps it is simply too scary to contemplate.

Instead we rely on logic, we build skills, we march forward.

And yet the body and the subconscious mind keep us awake at night.

As Gabor Maté has written, anxiety is rarely a flaw to be eliminated. More often it is a signal of an old wound surfacing, an unmet need for safety, acceptance, belonging. The adult trader is no longer facing the parent, teacher or peer who once withheld that need, but the nervous system has not caught up. It is still scanning for rejection, exclusion, failure.

When recognised in this way, the 3am wake up call is less an enemy to be silenced and more a messenger asking to be heard.

The Hidden Cost

But when that messenger is ignored, the toll mounts quietly.

Sleep becomes fractured. Confidence frays. Conviction wavers when it is most needed. Decisions get forced when restraint is the better move.

And the real risk? The very qualities that propelled you to succeed: discipline, preparation, analysis don’t protect against this erosion.

So What Can Be Done?

The way through isn’t found in doubling down on industry knowledge or grinding harder.

It begins with noticing. Recognising the tells. Understanding what is at play beneath the surface.

From there, the work is to:

• Find the root cause of the fear

• See it clearly without judgment

• Address it at the level where it lives, often in the subconscious

• Replace it with patterns and beliefs that support rather than sabotage

Some will do this work alone. Others find it faster with the right help. Both paths are valid.

Practical Shifts

• Notice the tells 3am wake ups, looping thoughts of a restless mind. These aren’t weakness - they’re signals.  Treat them like data points that reveal where your attention is being pulled.

• Separate skill from state You can be highly capable and still anxious. The anxiety reflects your inner state, not necessarily your level of ability.  Naming this distinction helps stop self doubt from bleeding into performance.

• Flip the question “What if I fail” can become “what if this shows me what I value most?.” Same start, different ending.  Reframing reshapes the energy of the question, moving it from fear to curiosity.

• Build trust Confidence doesn’t appear out of thin air.  It’s built by keeping small promises to yourself.  Honour them. Record them.  Review them. Over time this compounds into resilience you can draw on.

The Path of Least Resistance

The 3am wake up is a signal, not a verdict. It is a sign that something deeper is asking to be seen.

What matters is not silencing the signal, but hearing what it has to say. Meeting it with awareness brings a steadiness and calm that allows you to proceed in alignment.

Always happy to have a conversation in confidence if you recognise yourself in any of this and are looking for some support to help guide you through.