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Secretly Wishing for a Different Career? How To Turn Your Passion Into Reality

Managing Your Own Value Polarities Can Make That Dream Job Possible

close-up of dandelion seeds

In the fall of 2011, I’d been CFO at Microsoft North America for nearly five years. I was the financial leader of a major division of a global tech powerhouse, with stewardship for many billions of dollars. 

My team and I had grown operating income faster than revenue every year, consistently hitting our corporate targets. Year after year, the company named my organization the best finance geography. Our customer satisfaction numbers soared. Employee satisfaction improved by double digits. And my team became a career destination within Microsoft finance. By all accounts I was enjoying significant career success.

Yet I had a profound sense I was in the wrong career.

In truth, I’d never considered myself a “finance guy.” I had ended up in finance mostly through a series of coincidences. I excelled in my career not because I was a genius at managing income statements and balance sheets but because I was an effective leader who delivered results.

As the years went by, I “geeked out” more and more on the study and practice of leadership. Building, inspiring and leading high-performing teams became my passion. That passion led to increasingly larger roles, culminating in my CFO stint at Microsoft. It was the secret sauce of whatever success I eventually attained. 

But I was becoming increasingly restless. I itched to ditch corporate finance and pursue my leadership passion full time, perhaps as a leadership consultant or executive coach.

“Am I right? Am I wrong? What have I done?!”

I tried to console myself with the idea that there was no better place to apply my leadership skills than in the very heart of the business world. But I was growing ever more uninterested with the profession of finance itself.

The problem, of course, was money. I was a husband and a father of four kids – two in high school and two in college – with associated expenses. And there were other financial obligations, including a hefty mortgage. 

In short, I had important responsibilities as a provider. I took these responsibilities seriously and felt a strong sense of duty toward them. Fulfilling those responsibilities was very important to me, as well as gratifying. At the same time, my passion for devoting myself 100% to leadership work was becoming a clarion call I couldn’t seem to ignore. 

I felt caught between two contending values – both honorable, yet mutually exclusive. 

Why would you give up a good thing?

With these polarities rattling around in my head, I hopped on a flight from Seattle to the Bay Area to attend an intimate leadership retreat at the Stillheart Institute, a tranquil sanctuary nestled in the Santa Cruz Mountains. 

The event was hosted by Fred Kofman, then co-founder and president of Axialent, and an executive coach and advisor on leadership and culture who’s been called the "high priest of capitalism" by Reid Hoffman. Fred has authored such seminal business culture books as Conscious Business and The Meaning Revolution. 

The half-dozen attendees were CEOs and division presidents – a veritable Who’s Who of corporate America. I was the most junior of the group and appreciated the opportunity to join these industry captains for two days of Fred’s tutelage. 

Of those two days of mostly intimate conversations, there were two brief interactions I’ve never forgotten.

The first was during a one-on-one coaching session with Fred. I took advantage of that opportunity to seek his support in thinking through my career dilemma. I laid out the situation as best I could. He listened attentively. In the back of my mind, I was hoping he would offer some creative, courageous idea to simultaneously honor both of my competing values. 

Instead, he asked me why I would ever give up a successful high-income career for a risk-laden entrepreneurial venture I was ill-prepared to pursue, especially since it was likely to upset the family apple cart. 

At the time, I took his response as a clear condemnation of the consulting/coaching option for me. I left that conversation believing someone I admired had just advised me to stay my professional course. (In retrospect, I suspect he was pressure-testing my conviction.)

I felt disappointed but resigned to pragmatism.

Managing priorities and stubborn siren songs.

My second enduring memory of that retreat happened when we were all parting ways. 

After our one-on-one coaching sessions, each of us shared our coaching topic with the group for additional feedback. When I shared mine, the group nodded their assent to the outcome of my conversation with Fred and I began to feel more comfortable with the idea of sticking with my finance career.

But later, as we were saying our goodbyes, John Mackey, CEO and co-founder of Whole Foods Market, and co-founder of the nonprofit Conscious Capitalism, Inc., looked me in the eye as he shook my hand and quietly but firmly said, “Don’t give up on your dream.”

I flew back to Seattle that day oddly content. Though I didn’t fully appreciate it at the time, I’d just learned an invaluable lesson: It’s possible to hold competing values with grace. 

What I understand even better today is that sometimes it’s important to manage (in this case, sequence) seemingly competing values or priorities. 

For the next five years, I continued my work as a CFO. That work enabled me to honor one of my core values – family. I strove to embody that value in many ways, not the least of which was continuing as a reliable provider at a time when that was especially needed. 

But by the time 2016 rolled around, circumstances had changed. With our kids now out of college, my wife and I were empty-nesters – and our nest egg was in pretty good shape. We had entered a phase of life when we could bear more risk. 

Still, despite my dream’s stubborn siren song, I had a hard time mustering the courage to leave a successful finance profession and start my own business. After 27 years in the corporate world, becoming an entrepreneur was a daunting proposition. 

Getting off the fence and on the road.

Mother Nature kicked me off the fence. As I’ve written before, I nearly died that year due to massive bilateral pulmonary embolism. That got my attention. As I lay in the ICU holding my wife’s hand, I realized more than ever how fragile and short life is – and how little money and material things really matter. 

As soon as I got out of the hospital, I spent the next year retraining myself. I got certified as an executive coach and facilitator. I also got certifications in personality and leadership assessments. I started spreading the word that I was about to make a major career change. I put up my website and interviewed successful executive coaches to learn the keys to their success.

Then I had to learn how to market myself. For the first six months, I worked nights and weekends to rebrand myself from CFO to executive coach. I let everyone in my network know about my new business, getting a lot of encouraging words – but very little income. We were fortunate to have rainy-day savings to get us through the transition.

Little by little, though, my fledgling business began to gain traction.

Today, I get to help others build the muscle to achieve their aspirations, four days a week. For me, it doesn’t get better than that. My wife says she can tell I’m happier with my work than I’ve ever been. As a bonus, I earn enough income to sustain our lifestyle. 

Positive/positive polarities.

I recently came upon John Mackey’s explanation of polarity theory in his latest book, Conscious Leadership. He writes, “...while some polarities are positive/negative (war/peace, profit/loss, wealth/poverty), others are actually positive/positive. Which means both sides are actually desirable.”

As I pondered those words, I realized that for many years I had unwittingly set up my career choices (corporate finance or freelance executive coaching) as either/or propositions; I believed I could do one or the other, but not both. 

It turns out I was wrong. 

In fact, these two career options had a high degree of interdependence. For instance, the real-world business experience I gained as a senior finance executive prepared me to be a better coach. The money I earned (and saved) as a CFO enabled me to finance the income gap while I got my new business off the ground.

Likewise, the leadership principles I teach and coach executives on today, and which I “geeked out on” for many years while I was CFO-ing, enabled me to be a more effective corporate leader and deliver high-impact results for the companies and people I served. 

When looked at systemically, my ostensibly mutually exclusive career options weren’t that at all. Each was linked to and supported the other. They were interdependent.

My good friend Bert Parlee, a clinical psychologist and leadership coach, explains, “A fundamental question to ask when encountering a difficulty is: Is this a problem we can ‘solve,’ or is it an ongoing polarity we must manage well?”

Using core values to harmonize your life’s polarities

Over the course of my 27-year career in business and in my executive coaching practice, I’ve often come across executives who struggle with seemingly contradictory priorities or competing values. Frequently, their challenge appears to be choosing between putting career first or putting family first. 

What I like to help them see is that these apparent trade-offs are not usually quite so binary. More often, they’re an opportunity to craft a harmonious life structure based on core values. 

Here’s how to do it in three powerful steps:

  1. Define your core values. Your core values are those ideals that are enduringly important to you – for example, integrity, family time, teamwork, winning, and so on. Adherence to your core values determines the choices you make in virtually any situation – from what you think about, to how you spend your time, to how you treat others. Ponder your core values. Then memorialize them by writing them down. 

  2. Lay out your operating principles. Operating principles are the embodiment of your values. In other words, they explain how you intend to live your values. For example, your operating principle for the value of humility might be, “I seek differing viewpoints and strive to learn from others.” Your operating principles describe how you and others will know you’re living congruently with your values. Write down an operating principle for each of your core values. 

  3. Routinely assess your gaps and course correct. The gaps between your actual behavior and your expressed values are opportunities for course correction. Sit down on a regular basis, write the name of one of your core values, note an important instance when you didn’t honor that value, then write your course correction commitment. Pro tip: Doing this weekly is most effective.

As noted earlier, your core values and operating principles will inform how you make virtually all your decisions, including how to manage polarities like giving time to family or to your career. Keep in mind that your values may change somewhat over time, and that’s OK. Continuing to hone your values will help you make better choices.

The rank order of your values and priorities will likely shift with time. What’s at the top of your list in your 30’s may fall a few notches by the time you’re in your 50’s. It’s important to pay attention to these shifts to make the best choices at any point in time. In my case, building additional financial resources moved down my list once my fundamental goals had been met.

What’s your secret sauce? What’s your secret career passion? Do you find yourself pushing away an inner yearning for a different career path simply because you believe it’s impossible?

If so, I encourage you to stop and take the three steps above. You may find that, in fact, there’s no problem to solve – only a positive/positive polarity to be managed. And that’s your opportunity to implement a life structure balanced on your own values and passions. 


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