Conviction with a side of humility: The real edge in investing

After years of working with top investors, I’ve seen firsthand that conviction paired with humility is what fuels success. Yet most investors learn these traits the hard way - and have the battle scars, sleepless nights and strained marriages to prove it! 

While nothing beats on-the-job experience and time in the market, some profound insights and learnings can be fast-tracked. This is particularly the case for non-technical traits, like conviction and humility, that depend on self-awareness, self-management and emotional intelligence. 

Developing these traits is a classic adaptive challenge, meaning to fast-track the development of conviction and humility you must:  

1. Shift how you see yourself (your identity, influenced by your purpose and values)  
2. Recognise how you get in your own way (usually tied to ego, fear and insecurity)
3. Commit to a development plan to overcome these maladaptive behaviours. 

Let me step out each of these. 

The power of identity

Your identity is how you see yourself. Much of what you do stems from your identity, and in turn, your actions reinforce it. 

If you see yourself as someone who values the input of others, you’ll effortlessly test your thinking and analysis with colleagues to build conviction in your ideas. You’ll also be more comfortable providing your input and constructively challenging others. Seeking out and contributing to robust debate then reinforces your self-image as someone who thrives in the contest of ideas. As best-selling author of Atomic Habits, James Clear says: "Every action you take is a vote for the type of person you wish to become.”  

How does this help you be a better investor? 

Investors who align their investment style to who they are more easefully play to their strengths, building self-belief and conviction over time. Knowing this also helps you find a team who values your approach. Trying to mimic your senior investors, on the other hand, creates an internal friction that undermines performance and wastes huge amounts of energy. 

Connecting with who you are, what and who shaped your identity, and how it fuels your passion for markets and investing, will allow you to define an investment style that aligns to your strengths and purpose, which you can then refine over time.  

A practice of holding this identity lightly is key, for two reasons.  

When you’re fixated on being a certain thing (eg I’m a great fund manager who needs to be right and win), you will unravel when you inevitably make the wrong call. If you can evolve your identity to be anchored to intense curiosity and self-compassion, for example, you’ll develop that mindset and habits that drive performance and manage fear and anxiety, which leads to the second reason. 

For you to change and grow over time, you need to evolve how you see yourself. To the extend your current identity impairs your professional impact, you’ll need to unpack and upgrade it to shift. 

In other words, continuously refining your identity is key to achieving your big development goals, stepping into more senior roles and enjoying work more. Becoming crystal clear on those development goals comes next. 

Determine your development priorities

Once you’ve developed your core technical skills (your outer game), your greatest growth edge comes from addressing behaviours that are fuelled by ego and insecurity (your inner game).  

Our ego and insecurities are running us all the time – either a little or a lot. How they show up as maladaptive behaviours will likely be the shadow or flip side of your strengths. 

If your strength is deep analysis, you’ll struggle bouncing around ideas, and asking for help and speaking up until you’ve got all the answers. People with extraordinarily high standards (ie perfectionists) tend to dislike receiving feedback and don’t like being challenged. If you’re a confident and compelling presenter, you’re possibly not a great listener. Highly competitive people find it harder to make sell calls when the market is moving against them. People pleasers and peacemakers find it hard to challenge others. 

Knowing how you self-sabotage to undermine your conviction and humility is the precursor to rewiring these reactive tendencies and more fully expressing your skills and talents.  

Plan and commit

Change depends on an emotional, whole-body commitment to the endgame, and a clear process to support it. We use the Immunity to Change process in our development programs, and it looks like this: 

1. Define the one change that would most enhance your conviction and humility.
2. Identify the benefits of achieving that change. 
3. Pinpoint behaviours that work against you and recognise their cost (maladaptive behaviours). 
4. Examine why you hold onto those behaviours—usually for self-protection. 
5. Challenge the underlying assumptions that keep you stuck. 
6. Distinguish between facts and self-created narratives.
7. Take steps outside your comfort zone to align with your goal. 
8. Lean into discomfort and notice how your mindset shifts. 
9. Acknowledge progress and the rewards of change. 
10. Repeat. 

Want to fast-track your investing career?

Mastering conviction with humility isn’t just about self-awareness—it’s about continuous practice and the right support. That’s where our Keystone Analyst Program comes in. Designed for investment analysts, this program helps you build the self-belief, emotional intelligence, and decision-making skills that set top investors apart.

If you’re ready to refine your edge, be a better investor and step confidently into senior roles, Keystone gives you the tools to get there. Find out more>