A witty column about the genuine, emotional, and humorous exploits of coaching elite executives.


Are You Happy? Become A Student Of Yourself

clarity leadership self understanding

There are only two types of executives that I work with. Those that have clarity on what makes them happy and those that don’t. And I’ll tell ya, the latter is far more common. 

I’d argue that even those that say they have crystal clear clarity on happiness secretly don’t know what they want to be when they grow up. Right when you think you have it figured out, BAM. 

New factors to calculate: a shift in the wind, a folly in the market, or an unexpected family emergency. A grip of factors, some in our control and others not, influence our career and too often the happiness that we let our careers dictate.

To get clarity on what makes you happiest in your career, you must first recognize that you’re optimizing a moving target. The only constant is change.

It’s okay to question your future and think about ways to be more intentional, even if the changes you’re considering aren’t jiving with a ‘perfect linear’ career. We’ll cross that bridge in another article.

You Are Not Your Career

Highly successful executives are often best known for their work. Sometimes to a fault. 

When they stammer around another 4th of July backyard BBQ, they introduce themselves as Janet McLegend, Vice President of Operations. Not necessarily as the mother of Tommy, the little shit who blasted Aunt Charlotte with mosquito pond water from a Super Soaker

Janet is a shark in the boardroom but just another Karen at the barbeque.

Can we blame Janet? Becoming a Vice President of anything is no small task. It’s ruthlessly difficult and impressive AF in most cases. You should be proud! But I’ve found that too often we put too much stock in our careers and forget who we are in our life. Has this happened to you?


You Are Always Changing

You are constantly changing, growing, and evolving. This isn’t only true of your career and the speed of innovation these days. The change that you experience is happening faster than you think. In just a few months, you can be a completely different person, even if your title at work remains the same. 

I’ve found this change especially pertinent when navigating major life events, such as the kids going to college, an estranged relationship with your spouse, parents in failing health, or starting a new executive role. And sometimes all of these things happen at the same time.

Major life events don’t wait for opportune timing. You need to embrace the process of rolling with the punches and take a moment to study yourself for signs of happiness (or lack thereof). 


Become A Student of You

Take a moment to acknowledge all that you are responsible for keeping in order.

A marriage, a mortgage, a gaggle of children, a 4-figure Costco bill, an ever-growing list of subscription services you don’t need…  And compare that list with your executive priorities. A 9-figure P&L, staff of 100, high-priority clientele, investors, shareholders… 

Where did you put yourself on that list? After all, these responsibilities start with you.

Many clients that I work with forget themselves as a priority. They’re quick to tackle a nearly impossible laundry list of responsibilities for others—but hesitant to take a breath, invest in themselves, or dive deep into their own happiness. They make sacrifices for others to be happy.


Considerations For The Week

Become a student of yourself this week. Does getting up each day fill you with joy or compound stress and anxiety? Do you know why that is?

If you’re unsure, let me annoy you by asking you to start a running tally. Study what you feel and when you feel it. Categorize your emotionally tallied list by time of day or focal point. 

For example pre-work, early day, mid-day, late day, and post-work or go broader with career, parenting, love, character, health, emotions, etc.

Now grade how you feel in each category. For the sake of sanity, I recommend keeping this exercise simple with a 3-emotion limit: good, bad, and neutral. (You can also get really deep by mapping how your 27 emotions trigger each category you’ve listed, but that’s a tall order when starting out). When you document a feeling, simply ask yourself, “Why do I feel this way?”


A Really Important List (Honestly)

Your list may look something like this:

Pre-Work: I feel bad. Why? I continue to get poor sleep with multiple interruptions. I felt stressed about my morning routine and ate unhealthily. I’m not looking forward to leading a challenging meeting at work later. 

Early Day: I feel neutral. Why? Nothing stands out as good or bad. My day improved after a cup of coffee. I took some time to prepare for the tough meeting later.

Mid-Day: I feel good. Why? I am energized and find myself focused this afternoon. I overcame the tough meeting and I didn’t schedule too many calls. I feel productive.

Late Day: I feel neutral. Why? I feel impatient about ending my work today. I don’t want to get started on another monster project until tomorrow. I am eager to get more time with my family this evening.

Post-Work: I feel good. Why? I was proud of the work that I got done today. I had enough energy to make dinner for my family and conquer a family game night without touching my phone.

This is a simple exercise that you should try for 21 days straight—or the mythical time it takes to form a new habit. The idea is to get familiar with what is directly influencing your happiness.

You’ll learn more about your warning signs such as feeling emotionally drained, losing concentration, or realizing the point where diminishing returns start. Perhaps more importantly, you’ll recognize the moments that trigger happiness and joy in your life.

Want to speak directly with me about your career? Contact me below.

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