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Loving What You Do

By Seth Streeter, a YPO member since 2008

As a top chief executive, you answer countless questions with poise and mastery, but can you answer the most important question of all: Do you love what you do?

Have you become so caught up in your dutiful responsibilities, packed daily calendar and travel schedule that you forgot to check in and ask yourself, “Am I still having fun?”

The reality is that not all of you still love what you are doing. But you hesitate to make a change. You may find yourself saying:

  • But … I’ve worked so hard to get here I can’t back out now.
  • But … I have so many people who depend on me I can’t let them down.
  • But … if I can hang in there for just five more years, I’ll have enough money to support my family and our needs.
  • But … what the heck else would I do?

Why is this? And how can you move bravely toward what you love?

I interviewed Jody Miller, CEO of C2C Executive Search & Strategic Management, a bestselling author and keynote speaker, on how leaders can find meaning and happiness in their demanding careers, and even learning some approaches from the new generations in the workplace.

Redefining work and happiness: Generational perspectives

Seth Streeter: Jody, why do so many company leaders not love what they do?

Jody Miller: I spend every day interviewing and helping chief executives, graduates from Ivy League colleges and large universities and many who haven’t even gone to college, to understand why they are not happy with their work. This phenomenon cuts across all industries and educational backgrounds.

Based on more than 30 years in corporate America — including the last 13 as a career-life coach and strategic consultant to job seekers and companies — I have discovered some reasons why successful executives feel unhappy and need to go through a career shift, regardless of the level of wealth or success they have achieved.

Also, I’ve come to realize that different generations filling today’s workforce have completely different approaches to work. This can teach us a lot about how to find meaning and happiness in our own work.

Millennials have surpassed baby boomers as America’s largest living generation, and they have eclipsed Generation X as the largest group in the workforce. Baby boomers, those born between 1946 and 1964, have created some of the most profitable companies in the world. Microsoft, Apple and AOL, to name a few. They have obtained status, wealth and power, and all the stuff that comes with it. But along the way many began asking themselves questions like, “Is this all there is?” or “What is my purpose in life?”

Feeling stuck? Don’t wait to find your joy

Streeter: What happens when someone feels stuck but can’t seem to make the shift due to all they have taken on?

Miller: Unfortunately, many leaders in this position decide to put off play until retirement.

Streeter: That doesn’t sound so bad.

Miller: Maybe. Maybe not. If we wait to be free from the shackles of work that we no longer love (or maybe never did in the first place), there are consequences:

  • We have to face the fact that, when we retire, we may not be in the same physical or mental shape we are now.
  • The cost of health care keeps skyrocketing, and the chances of developing debilitating conditions increases with age.

If you are staying in your present position even if it is not making happy, it gets to the point where you must ask yourself, is joy worth waiting for?

Streeter: If chief executives are unhappy with their current work because they have let everything in their life come second, what should they do?

Miller: They should make a shift. And many do. Among baby boomers who chose to start a business of their own, Gallup has found their motivation breaks down this way:

  • 32 percent to be independent
  • 27 percent to pursue a passion
  • 24 percent to increase income
  • 10 percent because they have an idea for a product or service that meets an unfulfilled need

Those top two reasons tell me most boomers want to play again, before retirement. Without even realizing it, they are taking lessons from the largest cohort of today’s workforce — millennials.

Work as play: What we can learn from millennials

Streeter: What is your perspective on millennials and what can we learn from them?

Miller: This starts with understanding the differences in how these generations were raised. As I mentioned, baby boomers (and Gen Xers close to the tail end of the baby boomer scale: 45-50) had a lot of freedom as kids. They figured out what they loved because they had lots of free time to just be. They dreamed and invented and created amazing companies, but some, when it came time to focus only on responsibility, became dissatisfied and needed to make a shift.

Millennials have taken an entirely different path. Their childhood was scheduled — a lot. Structured play dates. Structured activities.

Technology is also a huge factor. With the explosion of the internet, information became available at the click of a mouse. We found out what diseases our kids might have, we learned about criminals in our towns and we became scared. We locked our doors and drove our kids everywhere, eliminating the opportunity for free play and creative discovery.

Streeter: What about school?

Miller: For baby boomers, school was there, but — after school — play was the focus. Homework was minimal. But for millennials, B’s were not good enough anymore. Everything we read said that getting into college was next to impossible, so our kids had to be exceptional at something. Lacrosse, tennis, violin, chess, school. Practice, practice, practice. All supervised.

Streeter: What happened?

Miller: They rebelled. Just like every generation does based on their time. They decided that they wanted to play too, and they were going to finally live the life they wanted. As soon as they got old enough to go into the workforce, they started calling their own shots. They sought meaning in their work from the start. And if that meant that they hopped jobs to get it, they didn’t care.

Streeter: So, you’re telling me that millennials are getting a bad rap.

Miller: Precisely. Remember, this is the largest workforce yet, and we need to learn from them.

Building bridges through mentoring

Streeter: We’ve talked about what older generations can learn from millennials. Can millennials learn from baby boomers and Gen Xers?

Miller: Sure, particularly if there is a structure in place to pass that learning along. One thing I tell companies when I consult with them about creating happy cultures is to have the older generation mentor someone from the younger generation. You don’t have to create a playground for the millennials to work at, but you can learn from their passion for meaning and purpose and happiness in their work.

They aren’t going to wait until retirement to enjoy their life. They want work to be like play. I doubt we’ll see a lot of shifting going on with them, unless it’s to create the next set of great companies, like the baby boomers did.

I want to emphasize there is great value in connecting these generations. They can learn from one another and, I believe, collaborate in new ways that we can’t even imagine yet.

Streeter: Getting back to those chief executives who no longer love what they do. What’s your parting message for them?

Miller: Embrace change. Don’t be afraid to make a shift. Your contributions are valuable, regardless of when you were born. Try to connect with members of another generation, especially if you have stereotypes attached to them, and be open to learn. You just may find collaboration, meaning, purpose and happiness in your work along the way.

YPO member Seth Streeter is CEO and Founder of Mission Wealth, a leading U.S. wealth management company. Streeter was recognized by “Real Leaders” magazine in 2015 as one of the Top 100 visionary leaders who strive to create a better world. Watch Streeter’s 2016 TEDx talk The Untethered Life: Wealth Redefined.

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