Find Out What’s Missing When Success Isn’t Enough For You

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I had a recent conversation with a highly successful and respected entrepreneur regarding a Chief Executive Officer role they were offered.

The executive is in their early 50s. Makes several hundred thousand a year. Lives in the country with their spouse and children. Works a flexible 4-to-6 hour day. And everyone I’ve spoken with speaks very highly of them.

The CEO role in question leads thousands of staff across dozens of geographically distributed locations. It also requires a radical uprooting of their lifestyle. Full relocation, 50%+ travel—a major orientation period. The compensation is by-and-by a wash when you account for W2 taxes.

Professionally this appears to be a slam dunk—but personally this could be a high risk maneuver.

For many, that sounds damn nice. Sign me up, Jacob. We’ll worry about satisfaction later. I’ll buy that with my sweet CEO Centurion Black Card.

For others, it’s not enough. Sign me up, Jacob. But not for this job—help guide my ass into something better.

It appears they have it all—already.

Why is such an esteemed leader seeking an objective assessment on their career? What can’t we see what’s missing? What does satisfaction really look like?

If It Ain’t Broke—Do Fix It

For many type A executives, work is a mountain to be conquered. Success is never final—it’s always penultimate. Then the next success is penultimate. And round and round we go.

That mountain climb is greater the more complex the problem, aggressive the expectation, esteemed the title, or larger the number of revenues, employees, or customers. We conquer the new summit and we’ve leveled up again. (I’m not finger waving—remember I write what I need to hear too. I’m just as broken as you.)

However, if we’re being truly honest with ourselves, there is a tipping point when highly demanding roles are simply shit. Being an executive isn’t sunshine and rainbows. It actually mostly sucks. Even if we are the only ones that can weave golden strands out of crap—does that mean that we really have to fix it?

I’m talking about the roles that suck the goodness out of my fellow Type A’s.

The self-control, motivation, and competitiveness we’ve tapped for greatness in our past devolves into chronic competition, impatience, aggression, and hostility. We know we can conquer the negative traits, because we convince ourselves that we can always rely on ourselves to slay any big hairy monster.

But oftentimes we force ourselves into crappy situations at the detriment of our satisfaction—and most certainly at the spoiling of our spouse, children, friends, and community relationships.

I’m stumped. If we truly have been a success and we can live a more rewarding life today—why do we reach for more? Who do we need to impress? Why do we need to fix it?

Do You Even Know What You Want?

Set a goal. Win.

A programmed mantra beat into society from the first grammar school science fair to the SATs to the Summa Cum Laude to the great battle of the coffee-running interns to the annual performance reviews to your first P & L and the depression of a major corporate layoff.

Now, you are at the existential top of Everest. Few have joined the summit and 99% don’t make it this far through the entirety of their lives. And hey, you still have a wick to burn.

When you come to the realization that you can do anything with a goal—but the goals that society told you to dominate are barren—where do you turn? A harder challenge? Why must we do this to ourselves?

Perhaps it’s easier to accomplish someone else’s goals instead of taking the time to figure out our own.

If you find yourself here, you need to defy every ounce of what you’ve been told.

Don’t quickly jump into the next opportunity (though I agree, it feels damn good to be wanted for other things).

Rather, you need to pause. You need to say no to everything. Just because you can doesn’t mean you should. It may be time to question yourself and what you really want from life.

Does a sabbatical make your eyes roll? Perhaps.

What about 3 weeks on a beach in the Caribbean with your family? Except… rather than planning every detail, you simply wing it? Is that crazy talk?

In order to figure out what you really want, you need to remove yourself from familiarity and put yourself in a new environment. You need a new perspective.

Homework Time, You Lucky Try-Hard You

I am starting to see why so many executive coaches go to school. Or study psychology. That isn’t me. I’m working through it as a dilettante, similar to most of you.

However, I have found the following self-assessment to be rewarding for myself and my clients for a period of self reflection.

We need to reverse-engineer the outcome that we want by assessing what is either helping us move forward or careening us off-track. For example, if we’re eating healthy, a choice to eat kale is a +1 whereas every choice to eat the delicious goodness of an entire rack of Oreos would be a -10.

Our professional lives are comparable. A choice to hold firm on our lunch boundaries or turn down a bad fit role is a +1 whereas a choice to close an out-of-scope deal is a -1.

At the end of the day, if your score is increasingly above zero, you’ll be progressing toward the future you want.

As you rank things compulsively, also think about those who most influence you. In a positive way, of course. What kinds of traits do they show you every day? And how can you be more like that and still feel genuine?

Start at a high level and work backward.

Download a printable worksheet here.

Part 1: Vision

  • Where do you see yourself in 10 years?
  • Where do you see yourself in 5 years?
  • Where do you see yourself in 2 years?
  • Where do you see yourself next year?
  • Where do you see yourself in 6 months?
  • Where do you see yourself in 3 months?

Part 2: Assessment

  • What do you need to stop doing?
  • What do you need to do less of?
  • What do you need to keep doing?
  • What do you need to do more of?
  • What do you need to start doing?

Part 3: Action

What are your 3 priorities today?

  • Ensure these are +1 actions
  • Set recurring reminders and put them on your calendar

What are your 3 stressors today?

  • What habits could be causing this?
  • Do these encourage more -1 actions?

Part 4: Be Accountable

Whether you print this homework and scribble down notes with a ball point, write it out in your notebook or on a whiteboard—or grab some chalk and write it in your driveway. I want to see what you come up with. Email me at – I’ll write back!

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