Meaningful and Happy Work: Lessons for Different Generations of CEOs

In Wealth Management by Seth Streeter


An Interview by Seth Streeter, the Founder and CEO of Mission Wealth,
with Jody B. Miller, the CEO of C2C Executive Search & Strategic Management and a Bestselling Author

Most top CEOs around the globe have learned how to tackle virtually any challenge that comes their way. They have acquired skills through training and experience that allow them to handle decision-trees like ninjas, quickly assessing, positioning and executing their organizations with a calm and calculated efficiency.

And it’s a good thing these leaders have mastered these quick-on-their-feet talents, because the required pace of dealing with such issues seems to be accelerating in this age of technology disruption.

While leaders answer the swell of external questions that come their way with poise and mastery, they often neglect to answer the one most important question:

Do you love what you are doing?

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

The reality is – and this may be a shock to many who see your life as being nothing but a lottery-ticket opportunity – that not all of you still love what you are doing. But you hesitate when it comes to making 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 that depend on me I can’t let them down.
  • But if I can hang in there for just 5 more years I’ll have enough money to support my family and our needs.

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

I interviewed Jody Miller, the CEO of C2C Executive Search & Strategic Management, who is a bestselling author and keynote speaker on how leaders can find meaning and happiness in their demanding career positions.

Redefining Work and Happiness: Generational Perspectives

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

Jody Miller: It’s a very intriguing question. I spend every day interviewing and helping CEOs, COOs, graduates from Ivy League colleges, 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 over 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? Some, such as Bill Gates (Microsoft) and Steve Case (AOL) have shifted into lives of philanthropy and found new purpose in giving back. But for those who continue to slug it out regardless of a lack of satisfaction, it’s all work. Just work. Play is something they put off for when they are retired.

Doing the C-Suite Shift

SS: In your book From Drift to Shift: How Change Can Bring True Meaning and Happiness to Your Work and Life, you share stories about executives who have gone through a shift in their careers.

JM: Yes. I have stories about amazing leaders – such as the private equity executive from a bulge bracket investment bank who was impossible to get an appointment with, was at the top of his game and made a ton of money. But he was miserable. Why? He hated what he was doing. It wasn’t fun and it didn’t hold meaning and purpose for him.

SS: What happened?

JM: He quit.

SS: Just quit?

JM: At the peak of his career. He wanted to find something more. He wanted that feeling of exhilaration, like when we were kids. He wanted to jump out of bed in the morning and get the day started as opposed to wanting to pull the covers up over his head and go back to sleep.

SS: How did he find what he was meant to do?

JM: It took some time. He started out a little lost. Put on a suit and went into Manhattan, wondering why he was doing it. Had coffee meetings. Explored. And then he traveled around the world until he found inspiration. He studied philosophies and simpler ways of life and gained a deeper understanding of who he was. He went back to his memories of creative play and started to rediscover who he was and what he wanted in life. We can learn a lot from remembering what we loved as a child.

SS: So what does he do now?

JM: It’s amazing. He takes start-up management teams on retreats where they dig deep into who they are as people and leaders, as well as learning how to build their start-ups structurally. His retreats are intense and revealing. Leaders find out what they are made of – and what they are meant to do. Some make huge shifts, like he did.

Feeling Stuck? Don’t Wait to Find Your Joy

SS: What happens when someone feels this way but can’t seem to make the shift due to all they have taken on? They may not want to abandon their company, even if they are at the top of their game.

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

SS: That doesn’t sound so bad.

JM: 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 healthcare keeps skyrocketing, and the chances of developing debilitating conditions increases with age.

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

SS: So, if CEOs are unhappy with their current work because they have let everything in their life come second, including taking care of their bodies, relationships and interests, what should they do?

JM: They should make a shift. And many do. Among Boomers who chose to start a business of their own, Gallup has found:

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

Those top two reasons tell me that a majority of 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

SS: So what are some of those generational differences you mentioned? Aren’t Millennials often stereotyped as lazy, entitled, spoiled job-hoppers who live off their parents?

JM: I have a different perspective than the stereotypes that the media feeds us, because I deal with Millennials as much as I do Gen X and Boomers. And I have three Millennials of my own.

SS: What is your perspective on Millennials and what can we learn from them?

JM: This starts with understanding the differences in how these generations were raised. As I mentioned, Boomers (and Gen Xers close to the tail end of the 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.

So the Boomers (and early Gen Xers) have a formula that looks like this:

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.

SS: What about school?

JM: For 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.

SS: I’m exhausted.

JM: So were the Millennials.

SS: So what happened?

JM: 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.

SS: So you’re telling me that Millennials are getting a bad rap.

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

Building Bridges through Mentoring

SS: We’ve talked about what older generations can learn from Millennials. Can Millennials learn from Boomers and Gen Xers?

JM: 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 Boomers did.

SS: Can you give me some examples of those great Millennial companies?

JM: Facebook, Pinterest, Instagram, DropBox, AirBnb.

SS: And what about great companies for the Gen X generation (1965-1984)?

JM: PayPal, Tesla, one of Twitter’s founders, William Sonoma.

There are great companies in every generation. But some of the greatest ever are from Boomers and Millennials, the two largest work forces in history. We need to pay more attention to connecting these generations. They can learn from one another and, I believe, collaborate in new ways that we can’t even imagine yet.

SS: So getting back to those CEOs who no longer love what they do. What’s your parting message for them?

JM: 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.

Seth Streeter is Founder and Chief Executive Officer of Mission Wealth, a leading wealth management company that specializes in comprehensive financial planning and investment advisory services for high-net-worth clients across the country. A thought-leader on the subject of conscious wealth, Seth helps others reframe their perspective of wealth beyond finances so that they can enjoy more balanced, fulfilled and impactful lives.

Career and Life Coach Jody B. Miller is author of the new book “From DRIFT to SHIFT: How Change Can Bring True Meaning and Happiness to Your Work and Life." Jody is known as the “The Work Happiness Expert.” As CEO of C2C Executive Search & Strategic Management, Jody has helped thousands of people find true meaning in their work and in their lives and has helped companies create engaging corporate cultures.

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Founder and CEO

About the Author
Seth brings vision, passion and deep interpersonal connections to the Mission Wealth team and client families. He considers it a privilege to serve by helping people live more fulfilled lives.



Founder and CEO

About the Author
Seth brings vision, passion and deep interpersonal connections to the Mission Wealth team and client families. He considers it a privilege to serve by helping people live more fulfilled lives.