One Piece of Career Advice More Valuable than Title, Salary, or Status

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Making the move

I sat in a board room across from our new Marketing executive and my now direct report, I knew it was time for me to play big. Ever since hitting a glass ceiling of accelerated growth and learning I had felt uninspired and unmotivated. Work had become comfortable. Lacking challenge, complexity, and adversity – work had become boring and monotonous. Worst of all, work had become a daily energy suck.

“I need to be thrown back in the deep-end. I need a challenge that involves leading a team towards a massive and nearly unachievable goal. I need to feel like I’m in way over my head.”

My heart was pounding as I said the words as I realized that a statement like this paints a very clear picture and one of two major events would likely take place: 1) My Marketing exec would see me as overly ambitious, possibly a threat and work to sideline and silence me which would quickly lead to my resignment, or 2) my VP would believe in me and give me exactly what I was asking for… In my mind, both outcomes were equally frightening.


The next time I thought of this early conversation was less than 2 months later. It was 11PM on a Wednesday evening and I was frantically rehearsing pages and pages of facilitated dialogue to my wife on the couch – my most faithful audience of one. As I worked through my notes over and over again I was nearly overwhelmed with nerves and anxiety. I felt like I had a world of pressure was on my shoulders, I could sense that somewhere in my brain there was a locomotive engine manufacturing clean raw energy from the intense stress I was stimulating.

I paused for a moment and realized something – I freaking loved it! This was a Flow state on steroids.

Then a beautiful realization put a grin on my face.

I was back in the Deep End. Fully struggling to keep my head above water, about to embark on a journey leading a team to do something no one in the company had done before.

I silently thanked my VP for believing in me and launching me head over heels into this uncomfortable zone.

Over the next two days and coming months I would be stretched to my limits over and over again as I led an incredibly complex product and acquisition management process.

A New Way of Evaluating Opportunity

This wasn’t the first time I have been thrown head over heels into the deep end and it certainly won’t be the last. But a profound learning came with this experience…

The most valuable career advice I could ever give someone is to seek out and chase these “deep end environments” with reckless abandon. Become an expert at identifying these paths in every aspect of your life. More than salary, title, organization, department, or network – this will be the greatest driving factor and catalyst for your long term success, in business and in life.

I can guarantee you this.

‘What’s so Special about The Deep End?’

These environments enable us to align our most core intrinsic drivers with meaningful work and impact in the world. The increased risk and heightened awareness of working outside our comfort zone enables us to access ‘Flow’ or in other words a dramatically increased level of performance. Working and operating in Flow states give us backdoor access to exponential personal growth and learning – we are actively hacking our mind, soul, and spirit – expanding the neuro-pathways and sensory receptors as if being hooked up to a super computer and downloading rivers of information – normally consumed at a rate 5, 10, and even 100 times slower.

‘Seek Out Your Deep End’

Here are some questions that have helped me identify the types of factors that lead to my best ‘deep end’ experiences and respective Flow states:

  • When you look at a new opportunity are there aspects of the role or environment that excite you and scare the hell out of you at the same time?
    • What are these aspects? Take note of the specifics.
  • When talking to others about the opportunity do you notice yourself getting excited, running out of breath, getting nervous, butterflies, goosebumps, sweats?
    • No joke, these are all great leading indicators of Flow and the Deep End.
  • When you look back to some of your greatest accomplishments in life, what are the first memories that come to mind? What are you incredibly proud about these experiences? What would you love to do again?
  • When exploring the opportunity with a key stakeholder or decision maker do you get nervous or anxious? Does the fear of failure come racing into your mind?
    • Perfect – you’re on the right track.
  • When was the last time you were engaged in an activity where time absolutely flew by?
  • When was the last time you walked out of the meeting or engagement and were literally shaking or buzzing with energy.
  • When was the last time you were running non-stop for 12, 14, 16 hours straight only to realize your energy tank is still full.
    • Is it overflowing?

The Deep End Paradox

All too often we enter the business world looking for a great salary, a well known and established company, a role that massages our ego, the list goes on. While these are all important things to consider they will always fall short of your expectations if you do not include the opportunity to thrive in your ‘deep end’. The former attributes check the right boxes but when compared to the individual who checks the ‘swimming in the deep end’ box the outcomes of these two careers will be drastically different...

One path is a slow and steady gradual increase over a long period of time, the other creates a hockey stick growth curve, exponentially expanding with every new day where Flow is accessed readily – this growth is compounded and cumulative in nature. The paradox, of course, is through seeking your Deep End as a primary driver to access this compounded growth comes all of the extrinsic incentives which you can see in this model are actually lagging indicators.

What Next?

My encouragement and challenge to you is to identify the paths in your life that force you outside of your comfort zone and into the rich deep end of learning and growth. Make this trajectory your reality. Do whatever it takes. However counter intuitive or backwards it seems at first – I encourage you to choose this path.

It’s a steep and gruelling climb to the top, but the views and sense of accomplishment is worth it time and time again.

Best of all, by reaching the summit of this mountain you’ll get a glimpse of a few more peaks on the horizon. 100 times higher and more daunting than where you are today.

You’ll be scared to death, and excited as hell.

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