How to Lead Yourself Well: 4 Proven Fundamentals

I once heard that the hardest person to lead is yourself. I’d never seen leadership in that way. However, since that day, I have proven the concept to be true. I am my toughest leadership challenge. Others have said you must first lead yourself before you can lead others. So, are you leading yourself well? Where do you start?

An Enduring Precedent

A few weeks ago my father-in-law introduced me to a book he thought I’d find interesting, Heroic Leadership by Chris Lowney. It outlines the rigorous and lengthy training process which has guided the great success of Jesuits for more than 450 years.

The legacy and enduring excellence of Jesuits is alone impressive. But what struck me most was their emphasis on coaching their recruits to lead themselves.

Leadership Begins With Leading Yourself

Jesuits cultivate their leaders through 30 days of exercises to “order one’s life.” This is the foundation upon which leaders are built.

In order to lead yourself well, you must become the expert on the topic of you.

The Challenge of Leading Yourself

I coach myself everyday to focus on the task at hand and do the hard things (like exercise and get up early). I set expectations, establish timelines, and do my best to maintain self-accountability. That’s leading myself, and I certainly don’t make it easy. How about you? Are you easy to lead?

If leading ourselves starts with self-awareness, then where do we begin? Where do we shine the light? What questions must we ask?

Leading Yourself Well Requires A Strong Foundation 

Lowney wrote, “A leader’s most compelling leadership tool is who he or she is: a person who understands what he or she values, wants, who is anchored by certain principles, and who faces the world with a consistent outlook.”

Isn’t this true? Aren’t the most effective leaders people who are grounded in a set of consistent values, which drive consistent attitudes, which guide their decisions, and direct their every actions?

Know Thyself

You can deepen your self-awareness and lead yourself well by inspecting 4 fundamental areas within yourself.

Know Your Strengths

As I’ve coached others to develop greater self-awareness over the years, I’ve found that people struggle with this. They don’t want to brag. They are their own worst critics. They are blinded by the negativity bias, the propensity to focus on the downside.

We need to know what we’re good at, what comes natural to us, our gifts. Knowing and applying them helps us fulfill our individual potentials. A flower garden without weeds (weaknesses) isn’t a flower garden at all without the flowers (strengths).

The power of knowing our strengths is no longer a secret. I recommend you take a strengths assessment to help you know your strengths.

When we know our strengths we can intentionally leverage them to bring our best selves to bear every single day.

Know Your Weaknesses

For many of you this won’t be difficult at all. The difficulty will be limiting your list (thanks to that nasty negativity bias again). However, to lead ourselves well, we must know where we fall short.

Once we identify our weaknesses, we can decide where to go from there. We can try to overcome a weakness or we may choose to compensate for it by surrounding ourselves with others who have our weaknesses as strengths. However, we can do neither without self-awareness.

By knowing our weaknesses, we are positioned to be on the lookout for how they may be undercutting our leadership. When we know our weaknesses we can choose how best to address them.

Know Your Values

Your values are your guiding compass. They are the deep-seated roots that make you tick. These are deeply held beliefs that guide your thoughts, emotions, and day-to-day behavior. They impact everything.

Think of the principles your parents instilled in you. Respect is earned not given. You will always be loved. You have what it takes. If you work hard enough you can accomplish anything. 

These values shape your worldview. They impact how you view yourself, other people, and the world around you.

When you know your values, you know what motivates you, what fuels your every action. What a powerful key to leading yourself.

Know Your Desires

Some of us grew up dreaming of making millions. Others of us dreamed of making a difference in the world. Some of us dreamed of being astronauts, while others dreamed of raising a family, or working in the family business. We all have dreams. Sadly, too many people give their’s up far too easily.

These dreams can shape our goals and desires. What is it you truly want in a family, a job, a home? What do you truly want in life? Money or power? Influence, love, or peace? Adventure or to make a difference?

When we know the desires of our hearts we can see where we’re going, the path we are on. When you know where you are going, you lead yourself in getting there.

Lead Yourself Well

To grow as leaders we must begin by learning to lead ourselves well. Leading ourselves well starts with building a strong foundation of self-awareness. As we discover our strengths, weaknesses, values, and desires we gain clarity in who we are. This is a life-long pursuit of self-discovery, learning, growth, and maturing.

Knowing yourself is what allows you to lead yourself well. As you lead yourself, so too, will you lead others – well.

Question: What makes leading yourself so hard? I’d love to hear your thoughts on this in the comments below, or on Facebook or Twitter.



Please note: I encourage reader discussion, however, I reserve the right to delete comments that are offensive or off-topic.

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