Does Your Career Feel Like a Pair of Old Worn Out Pants?

In the beautiful Boston suburb of Winchester, Senator Jason Lewis was giving a fiery presentation to a roomful of concerned parents, teachers and citizens.  The topic was educational finance reform.  Funding for education had been dramatically cut back in Massachusetts (and across the country for that matter) and something had to be done to stop the bleeding.  Having intensely studied the challenges around the educational funding gap for years, he was well equipped to speak to this topic. He was resolute in his delivery.  “I am committed to making sure that our cities and towns receive adequate and equitable resources in order to provide a second-to-none public education for our young people,” Senator Lewis assured the crowd.  “And now I want you to feel empowered to have an impact on this critically important issue.”  You could sense from the tone of his voice that this wasn’t just empty rhetoric.  He cared deeply about the public school system and was committed to fixing the problem.  As he methodically dissected the issues one at a time and recommended solutions to each of them, he could see the heads nodding in agreement.  This was not an easy crowd to please but he had clearly done his homework.  From the positive energy he was feeling from this discerning crowd, he knew in his gut that all the hard work was going to pay off.  He was finally in a position to make a real difference.

Rabbi David Spinrad was in the midst of delivering the sermon of his life at The Temple, a 1,500 member synagogue in Atlanta named by Newsweek as one of the most vibrant and dynamic in the country.  This wasn’t any ordinary service.  This was Rosh Hashanah, one of the most important Holidays in the Jewish faith.   Hundreds of families from around Atlanta filled every last seat in the sanctuary, all of them anxiously awaiting to hear a spiritual message that might move them in some profound way. It was intense pressure but he wouldn’t let it throw him off balance. In fact, it actually elevated his game.  It was a powerful and moving speech focused on how to view God in light of misfortunes that happen in life.  “God is not all powerful.  God is not all knowing,” the Rabbi confessed.  “Saying her death was for the good to a man who just lost his wife or God works in mysterious ways to a family who just lost their home are insults to our intelligence.”  His words echoed throughout the building. His passion penetrated your bones.  “If God knew everything, then we wouldn’t have any freedom.  Our choices in life would just be an illusion.  But we do have choices.  We do have freedom. Ultimately, we are the authors of our own lives.”  His deeply held beliefs may be antithetical to traditional religious ideology but they were his and this was his moment to distill them upon his people.  This was his moment to challenge conventional wisdom and to make an impact.  And from the look of all the mesmerized faces in the crowd, mission accomplished.

In the small charming southern town of Hillsborough, NC, there was a fine wine auction taking place. Mark Solomon, the wine director at the auction house, stepped up to the microphone. “Next up we have a real treat.  It’s a case of 1989 Chateau Haut-Brion. This is an exceptional year for this wine.   It’s rated a perfect 100 points by Robert Parker.” With that, he hands off the microphone to the auctioneer and sits back to watch the show. “O.K. folks.  Let’s start the bidding at $800 a bottle.  Do I have $800?  Yes, I have $800 from the lovely lady in the front row.  How about $900? Do I hear $900? ” The atmosphere was electrifying.  Before you know it, hands were shooting up from across the room.  And the phones were lit up as well.  Bidders were calling in from all over the world – Vietnam, Hong Kong, The UK, France.  By the time the evening’s auction came to a close, every last bottle would be sold with the total value clearing just over $1 million.  But it wasn’t just about the money. It was validation that his intuition about what wines would move was proven correct.  He had correctly sized up global demand for the wines he had so meticulously researched and sourced.  He was in the zone and that felt good.

So here we have a Senator, a Rabbi and a fine wine director.  So what’s so special about these people you might be wondering?  There are plenty of other politicians, religious leaders and wine connoisseurs out there.  What makes their stories so unique isn’t so much what they do but rather, what they did.  Senator Lewis was a technology marketing executive at the top of his game before he decided to run for office.  Rabbi Spinrad had previously built a thriving practice as a personal trainer, helping hundreds of clients get in shape. And as for Mark, our wine aficionado, he used to be a well-known neuropsychologist, working in a hospital with patients who had suffered from major brain trauma.  They each were in the midst of thriving careers when they decided to completely walk away and start anew.  They were all extremely successful by any measure but yet something was still missing.

After earning his MBA from Harvard Business School and spending a few years advising Fortune 500 firms while at the prestigious McKinsey & Co., Jason entered the glamorous world of high tech.  Next to Silicon Valley, Boston was one of the top U.S. epicenters for technology innovation.  There was no shortage of brilliant entrepreneurs or venture capital to fund them during the late 90’s but there was a dearth of seasoned management talent.  As such, Jason had no trouble landing a role in the marketing department at the high flying security software firm RSA Security. He quickly ascended the ranks and became a Vice President, overseeing all product management.  He was able to leverage that success into his next role as Chief Marketing Officer at Endeca, a well-funded company in the hot enterprise search space.  He had become a highly sought after marketing executive at the top of any tech recruiter’s target list.  He had earned his rightful place amongst the who’s who of the Boston tech scene.  He was a “player”.  Yet, despite all his success, he wasn’t really all that happy.

He just didn’t feel passionate about being in high tech. He didn’t feel passionate about being in marketing. Heck, he didn’t even feel passionate about being in business.  He realized he was an accomplished business executive.  While he clearly had a knack for business, he didn’t seem to really care about business anymore.  He felt himself becoming more and more withdrawn from the company and from the industry. As a software marketing executive, he just didn’t feel like he was making a real difference in the world and for that he felt empty.  On top of that, he was working crazy hours.  Being an officer in a venture-backed tech company wasn’t just a job, it was your life.  He loved his family, yet the demands of the job wouldn’t allow him to spend any quality time with them.  His health suffered as well, as his once routine visits to the gym became a rare occurrence.  Was this what he really wanted to do for the rest of his life?  Was this it?  For what purpose?

He knew he needed to find something away from the corporate world that would give him more meaning.  He knew he needed something more mission-driven.  And if he didn’t change course now, he probably never would. Inertia is a very powerful force.  So he quit his job and for the first time in his life, he found himself unemployed.

With the 70 hour workweeks behind him, he was finally able to spend a lot more time with his family and in other areas important to him which he had neglected for many years.  One of those was his children’s public school system.  He was becoming increasingly concerned about the educational budget cuts and when the school had to lay off its librarian and threaten to shut down the library, that was the last straw.  Jason knew what he had to do.  It was time to run for office. As an involved parent, his influence on such matters were limited.  But as a State Representative, he could have a much greater impact.  He had never run for office before and didn’t know the first thing about it but he wouldn’t allow his lack of experience deter him from his pursuit.  He was on a mission. He consulted with advisors, assembled a team of volunteers, pieced together his campaign and started knocking door to door.  He fought a very tough campaign focused on educational finance reform, civil rights issues and environmental policy and with all the momentum moving in his direction, the incumbent decided to step down.  Jason Lewis was now Congressman Lewis.

He knew deep inside that he had made the right career move but that didn’t mean it was an easy one.  His compensation as a local representative would be a fraction of what he had earned as a tech executive and without any upside (there are no stock options in the government).  There would be no second house. There would be no fancy car. There would be no exotic trips to remote parts of the world.  They would live a very simple life.  And whatever ego had been built up from having been a rising star in the enterprise technology world would be quickly shattered.  Let’s face it – not many people know who their local politicians are. All of those fancy educational degrees and corporate titles he had accumulated up until this point would mean nothing. He was essentially starting over.  But starting over in an area he actually cared about – local public policy.  And with job flexibility that would allow him to spend more time taking care of his family and taking care of himself.  For the first time in a really long time, Jason was happy.

David Spinrad was the proud owner of Good Life Personal Training, a personal fitness training business in the Bay Area he built from scratch.  He worked with a range of clients, from competitive athletes to everyday fitness enthusiasts.  He prided himself on getting to intimately know his clients and customizing training programs around their individual needs.  He was not the tough drill sergeant type. He was rather caring and empathetic, knowing the daily struggles many clients faced while chasing their health goals.  His client-centric approach was formally acknowledged when he was honored by the San Francisco Chronicle as the best personal trainer one year.  And in a fitness-crazed city with thousands of personal trainers, that was quite an accolade.  David had known he wanted to do something entrepreneurial coming out of college. He had wanted to be in control.  He had craved freedom and flexibility.  And he had achieved all of this with his personal training business. He was living the exact lifestyle he had designed for himself.  He should have been fulfilled.  But he was not.  He didn’t feel he was reaching his full potential.  He knew he had more to give to the world.  He knew that being a personal trainer was not his final calling card.

He took stock of his skills and interests.  He enjoyed interacting with people.  He enjoyed helping people become better versions of themselves.  He enjoyed inspiring people.  But inspiring people to improve their bodies just wasn’t enough anymore.  He needed something bigger. He wanted to inspire people to change their lives.  But how could he be in a position to accomplish that?  What new career might help him bridge this gap?  He wasn’t sure of the answer right away.  He simply had to have faith that the right thing would reveal itself at some point.  He just had to be patient.

He wouldn’t have to wait too long. That revelation would manifest itself during a trip to Israel, his first ever visit to the Holy Land.  David had grown up Jewish but not religious.  He was a “secular Jew”, observing the major Jewish holidays a couple times a year but not honoring the weekly Sabbath or keeping kosher or being a student of the Torah.  But that trip to Israel in his 30’s would change everything.  Reading about the Jewish homeland and actually being there were worlds apart.  Climbing Masada and touching the holy Western Wall and watching the sun set over the Old City of Jerusalem had all touched him in a very profound way that he couldn’t quite articulate.  He felt a greater interconnectedness with God.  He felt a greater connection to his people.  It’s like, for the first time in his life, he felt like he was finally home.  The next chapter in his life would be a mystery no longer. He could feel it deep within his soul.  He finally realized what he was put on this Earth to do.  He would leave the world of personal training and embark upon his new enlightened path to become a Rabbi.

The transition wouldn’t happen overnight.  It would take a few years of studying the different branches of Judaism, consulting with Rabbis, scraping enough funds to finance this endeavor and soul searching to be 100% sure this was the right path for him.   Rabbinical school is a five year commitment and over $100,000 in fees.  And going back to school after so many years removed from textbooks and lectures was a daunting task.  This would be a very intellectually challenging and time consuming program and David had never been a stellar student to begin with.  The typical Rabbi curriculum is a multi-disciplinary one and includes the study of Torah, Jewish history and the Hebrew language along with classes in psychology, community outreach and public speaking, just to name a few.  It was demanding work but he was prepared for it.

What he wasn’t prepared for was that in the midst of his studies, while he was making great strides, a terrible, unthinkable tragedy had befallen him and his wife.  They lost their child to a rare disease. A parent’s worst nightmare had come true. He would take a two year leave of absence from school to grieve and be with his family.  It wasn’t easy.  These were very trying times.  Here he was planning to devote his life to God and yet God had taken away something so precious and dear to him.  Meanwhile, their finances were in a shambles and they were down to their last penny.  He had to search deep from within.  These emotional and financial hardships would push him and challenge him but never break him.  His resolve was way too strong.  After his long hiatus, he somehow managed to muster up the courage and strength to continue on his journey.  And after a decade of first having his heart set on being a leader of the Jewish people, David Spinrad was ordained as a Rabbi.

Practicing as a Rabbi is no cakewalk.  It’s a very demanding job. With weekly Shabbat and Mitzvah services, you never have weekends to yourself.  And you are always “on call”, as births and deaths are never planned in advance.  Since you’re always in the public eye, you pretty much gave up your privacy.  You also have to be extra cautious in your daily life about every action, every statement, and every interaction since you are expected to continually practice the values and virtues that you preach.  In other words, you’re always “on”.  While perhaps a bit inconvenient at times, these tradeoffs were more than acceptable.  He knew what he was getting into.  Rabbi Spinrad could live happily with all of them, knowing full well that he was finally practicing what he was put on this Earth to do.

Dr. Solomon, as Mark had been known in the hospital where he worked, certainly wasn’t unhappy in his role as a neuropsychologist.  He enjoyed the interaction with his patients.  He relished making significant breakthroughs with patients and observing their progress.  And he felt proud to be a highly regarded psychologist in such as specialized field.  But it’s not to say it didn’t have its challenges.  It can get depressing working with patients suffering from traumatic brain injuries.  They can gradually improve but they’ll never fully recover.  And that’s hard to witness day in and day out.  But while the emotional challenges had its ebbs and flows, the administrative burden of working in a healthcare setting was constant.  After years of postgraduate education and specialized training, here he was spending half his time in a sea of endless paperwork.  It was mind numbing. But what other options did he have?  This was the life he had chosen.  This was his destiny.  That is, until that cool fall evening at his neighbor’s house when he took a sip of a 1955 Graham’s Vintage Port which would open his eyes to a world he never knew existed.

Sure, Mark had tasted wine before.  But we’re talking cheap $5 bottles. Perhaps he’d splurge on an occasional $10 bottle.  That was about it.  He liked it but wasn’t in love with it.  But that glass of aged port would awaken his gustatory and olfactory senses for the first time.  This was no longer just about drinking wine; this was about an all-consuming, full-sensory experience.  He was hooked.  He had been searching for a new hobby for some time but the hobby had apparently found him. He threw himself into the study of fine wine as if he were pursuing another doctorate.  Every extra hour of free time went into educating himself and every extra dollar to spare went into collecting another bottle.  Wine was oozing through his veins.

On a whim, driving home from work one day, he pulled off the road into a shopping center and strolled into a nondescript building with just three words atop the door: Leland Little Auctions.  Leland Little, the owner, greeted mark and asked how he could help.  “What do you auction off here?” Mark inquired.  “Mostly art and antiques,” Leland replied.  “How about fine wine?” Mark countered.  “I’d love to but I don’t know the first thing about wine,” Leland responded.  Mark smiled back, “Well, perhaps I can help.” That little conversation turned into a one-time experiment which turned into a trial run which eventually turned into a business partnership of selling fine wines on a regular basis through Leland’s auction house to customers all over the world.  Mark never envisioned wine as a money making hobby. That certainly wasn’t what had initially sparked his interest.  Far from it.  The money was simply the icing on the cake.  But as he sourced better wines, the customer base grew. And as the customer base grew, so did the revenue.  Little did Mark know when he first embarked upon this journey that he would eventually find a way to monetize his newfound passion to such a degree that he could eventually afford to quit his work at the hospital.  Mark Solomon was no longer a practicing neuropsychologist. He was now the Fine Wine Director at Leland Little Auctions.

While it may sound fairy-talish on the surface, Mark’s journey from psychologist to wine director was by no means an easy journey. Quite to the contrary.  Sourcing fine wine from around the country while building a global customer base of wine enthusiasts was a herculean task.  There was no how-to book to review.  There was no “Fine Wine Auctioneering for Dummies” on Amazon.  He would have to figure it out himself.  It was also a big hit financially at first.  As Leland’s wine director, Mark would initially only be earning roughly 1/3 the income he made at the hospital.  And it’s not like he was ever getting rich off that hospital salary.  Finally, there was the emotional hurdles to overcome.  He did not have the support of his parents. They couldn’t understand why he would want to throw away all those years of hard work and sacrifice, his advanced degree and his professional reputation to pursue some seemingly fleeting side interest.  This felt whimsical to them. Even Mark himself had doubts and would question his own judgment about whether he was making the best decision.  But he knew in his heart of hearts that this was the right move.  You only have one time around in this lifetime and he didn’t want to ever have any regrets.  He’d rather try and fail than die never having tried.  It’s a good thing he did.  He couldn’t be any happier.

These three ordinary people did something quite extraordinary.  It wasn’t so much that they had the insight that there was a more suitable career for them. We’ve all had those moments of inspiration. Rather, it’s that they had the courage to make the change and see it through.  And to do so later in life after they had built up solid reputations and income and respect in their original chosen fields is all the more impressive.  None of them were miserable in their former jobs.  In fact, they were all pretty content.  But content wasn’t good enough.  Content was a compromise they were no longer prepared to make.  There would be significant financial, emotional and social sacrifices but the potential payoff of a more fulfilled life was well worth it.  Make no mistake – it was still scary jumping off the cliff with uncertainty and doubt and fear hanging over their heads.  They didn’t quit their jobs at the top of their games and head into the unknown because they had no fear.  Rather, they took the plunge in spite of their fear.  They simply learned to live with that fear.  And they’re all in a much better place today.