Doing the Deep Work

When Mark Silverman arrived in DC on September 1, 1989, he was a 130-pound vagabond battling addiction and homelessness. He had driven across the country with no money, sleeping in his truck and living off of Diet Cokes and cookies he bought with a gas station card. “Before that, I had been living with a group of people that practiced a very strict lifestyle and morality together,” he says today. “It was somewhat like a cult, with good things and bad things about it. But I was ready to say goodbye to that life for good, so I left. On my own for the first time in my life, I was shell shocked and had no idea how I was going to live in the real world. All I knew was that if I didn’t drink, it was going to be okay.”

Mark had always been good at starting over, and he was ready to do the deep work it would take to pull himself out.

Mark had always been good at starting over, and he was ready to do the deep work it would take to pull himself out. He moved in with his brother, who had three requirements for Mark: he was to join AA, enroll in college classes, and go to the gym. And with those basic building blocks, Mark set to work creating a new life.

Mark had no life skills to speak of, but through his work living with the group for the previous nine years, he had established a core of strength and a strong ethical foundation. And through his experience with homelessness, he gained an impermeable humility that eroded any inclination toward self-centeredness, opening him up to truly caring about others. “That changed everything,” he affirms.

Over the next decades, Mark embarked on a whirlwind journey of discovery that led him to a career in the high-tech startup industry selling multi-million-dollar hardware and software solutions. The success and affluence was dizzying, but the pressure and pace became maniacal. Each year, he was expected to blow last year’s achievements out of the water. In 2007, he overachieved his goal by 200 percent, landing a $380,000 commission check and the honor of top sales rep in the region. “For me, that was the bar that meant I had finally achieved success,” he remembers. “It was the finish line that told me I was good at what I do. But then the clock struck midnight on New Year’s Eve, and the counter reverted back to zero, and the treadmill started all over again. It was a defining moment where I realized that there is no finish line, no moment of arrival in that kind of life. It just goes on and on.”

That year, the company doubled his goal again, but Mark’s focus was elsewhere. In search of ways to cope and thrive in the grind, he began a journey of self-discovery and deep introspection. He attended workshops, read books, took courses, and learned to meditate. He began training with some of the world’s top coaches in 2012, and in 2013, he formally launched his own transformational executive coaching business, Mark J. Silverman and Associates. “I work with CEOs, VPs, and high-level executives because I’ve been in business and I understand it, but I go a lot deeper,” he says. “If I do my job right, it changes a client’s life with their kids, spouse, and colleagues, and completely transforms how they show up in the world. It’s about helping them access their own core strength and wisdom, so circumstance does not influence well-being.”

Through speaking, writing, and direct coaching, Mark’s deep work helps people thrive in the world when it asks the most of them.

Through speaking, writing, and direct coaching, Mark’s deep work helps people thrive in the world when it asks the most of them. He gives them tools and strategies to be able to get past the presenting problem, like wanting to make more profit or wanting to do more sales. Five layers beneath that, he unleashes what’s really in the way of them doing what they need to do. “At the beginning of their careers, it all seems to work no matter the hours or demands. But as time wears on, as good and put-together as everyone looks on the outside, with their Hugo Boss suits and nice houses and BMWs, it becomes unsustainable. They’re actually fraying on the edges,” Mark observes. “Inwardly, they’re just hanging on. They let off steam through smoking or drinking or other destructive habits. Then, as people get older and take on more responsibility with spouses and kids, they have less energy, and success becomes even more difficult.”

Looking around, Mark saw his contemporaries choose one of three coping mechanisms, all equally caustic. Some put themselves on the backburner, neglecting their health and well-being to the point that they were a heart attack waiting to happen. Some ignored their relationships with their spouses or kids, often breaking up homes. And those who prioritized their families and their health had no choice but to sabotage their careers, because there simply wasn’t time for all three and the pressure was too great. “These are good men and women, and there’s no reason it has to be this way,” Mark affirms. “Success shouldn’t come at such a dark cost.”

For the high-powered, strung-out, but eternally earnest executive just trying to do what life expects of them, Mark is the perfect portal to a better way, because he himself used to be that person. Even as a troubled kid, he was drawn to the peace and perspective of a higher power and thought he might one day be a rabbi or a teacher. Mark was born in Brooklyn and raised on Long Island in a lower middle-class neighborhood of predominantly Irish and Italian families. His father ran a Burger King, while his mother worked in a furniture store. His brother was a full seven years older than him, and his sister a full eleven, with both engrossed in their own lives. “I was the traditional latchkey kid,” he says. “Nobody was home to raise me. I was on my own, free to get in trouble—and I did.”

“My brother teaches hand-to-hand combat and shooting, and says I’m still the toughest person he’s ever met in his life,” Mark says.

Left to his own devices, Mark and the other neighborhood kids stole bicycles, started fires, and beat each other up. As the only Jewish kid in his neighborhood, he was scrappy and tough, and though he was small for his age, he never lost a fight. “My brother teaches hand-to-hand combat and shooting, and says I’m still the toughest person he’s ever met in his life,” Mark says.

By the time he was thirteen, Mark was drinking and doing drugs. He stole alcohol from people’s houses and drugs from his brother, which he sold for spending money. His parents were clueless, and assumed that anytime he got into serious trouble, it was someone else’s doing. “They did the best they could, but were just really out of touch,” he remembers. “I had no role models for a successful life.”

Despite this disruptive lifestyle, and though he rarely did homework or studied, he always did well in school. His report cards always took note of his potential, lamenting his refusal to apply himself. “Sales guys know how to get stuff done,” he remarks. “They see the shortest distance between Point A and Point B. I knew that as long as I went to class and listened, I could do well on tests.” He also always had a job, whether it was working in fast food restaurants, a supermarket, or later as a waiter and bartender.

When Mark graduated from high school in 1980, he enrolled at Central Connecticut Community College and got a bartending job in nearby Hartford. Spending all his time at the bar, he flunked out after the first couple weeks— something he didn’t tell his parents until he was supposed to come home for Christmas vacation. Instead, he leaned into the hedonistic frenzy of his current lifestyle. “I would bartend from 10:00 AM to 6:00 PM, eat dinner, drink, go home, shower, work at the bar all night, and then take speed so I could do it all over again,” he recounts. “Everyone working in that world was like that, addicted to alcohol and drugs.”

Everything changed in 1983, however, when Mark happened to cross paths with Rosa, a 65-year-old Italian woman. “She practiced the Erhard Sensitivity Training, or EST, which transforms the way people experience life, such that the very process of living fixes the things a person is struggling with,” he explains. “She had garnered a small following, and when she met me, she confronted me for the first time in my life and said, ‘On a scale from 1 to 10 as far as functioning human beings are concerned, you are a negative two. You’re a mess, and you need help.’”

“It really set the foundation for me to know what integrity was, what God might be, and what relationships are all about,” he remembers.

Mark signed up for her workshop, and when he saw it was work he wanted to embrace, he moved into her farmhouse with the group. Together, they focused on changing the world to improve quality of life—a goal that would become a cornerstone of Mark’s character. As a community, they sifted through their memories from childhood to better understand themselves, and as a community, they exercised the demons  that weighed them down. “It really set the foundation for me to know what integrity was, what God might be, and what relationships are all about,” he remembers. “We committed to be drug and alcohol-free, and we held each other accountable. There were bad things about it, but ultimately, it saved my life.”

Through the five years that followed, Mark never spoke to his family. The group moved to San Diego, and then to Colorado, where he got married. He was thrown out several times through that period for drinking, and when his marriage ended after several years, he was thrown out for the last time. “I had no money and no place to go, but I was good at starting over,” he says. “I’d get a P.O. box and a job as a waiter, and then Rosa would magically know where I was and call me up, and I’d go back to the group. But not this time.”

Mark drove to Seattle, but opportunities weren’t presenting themselves. So he drove to Portland, but found another dead end. Destitute, he called his brother, who convinced Mark to come join him in DC. The day of his arrival marks the first day of 28-years-and-still-counting sobriety, and he got a job at the Four Seasons Hotel as a waiter. The following January, he enrolled in college classes at Northern Virginia Community College, and the following year, he moved out on his own. A few years later, he got married.

Through his six years at the Four Seasons, and with the support of mentor and hotel VP Stan Bromley, Mark was the first employee permitted to transition from the restaurant into a professional position when he applied to become an accounts receivable clerk. “I had never seen a fax machine, and I didn’t know what a copier was,” he laughs. “I just wanted to get out of the restaurant business and do something different. At age 34, it was my first white collar job.”

The following year, Mark landed a job as the Assistant Night Manager at the hotel—a gig he largely enjoyed, except for the stress of having to figure out within 120 seconds of having a fire alarm pulled whether there was actually a fire. “We had celebrities, royalty, and foreign dignitaries staying at the hotel, so they only wanted to evacuate if absolutely necessary,” he recalls. “It was up to me to make that call, which was incredibly nerve-racking.”

Mark quickly realized that the long hours and challenging schedule put him on a fast track to a career of limited earning potential, so he decided to leave the hotel business in 1998 to take his first sales job. “I took a career test and it said I should either be a writer, a lawyer, or a sales guy,” he says. “It wasn’t going to be either of the first two, so I decided to try sales. But when I went in to interview for a copy sales position and shadowed a sales rep while he knocked on doors, the manager told me I was a nice young man, but I’d fail miserably in sales. Later on, when I made my first million, I went back to kindly let him know he was wrong about that.”

“Most importantly, I realized that when I had the opportunity to develop relationships with people, they trusted me and wanted to buy from me,” he says.

Mark landed a position selling computer training—a grueling challenge that led most hires to quit before the end of the first month. Each sales person had to make sixty phone calls a day, and at first, Mark found it miserable. The company did offer free classes, however, and he soon discovered that people were much more receptive to buying additional training when they came in for those sessions. With that, he shifted his approach to the phone call quotas, instead focusing on the free classes. Within two months, he was the top sales guy at the company. “Most importantly, I realized that when I had the opportunity to develop relationships with people, they trusted me and wanted to buy from me,” he says. “That became the cornerstone of my success from then on.”

The following year, Mark went to a technology show in DC, where a company was selling a SmartBoard that translated handwritten notes onto a computer. “It was the coolest thing I had ever seen in my life, so I walked up and told them I wanted a job selling it,” he recounts. There, he also sold the first projector with a digital camera, and orchestrated several sales to the Marine Corps that marked the two biggest sales Toshiba had that year in the entire world. He was promoted to VP of Sales, and his salary doubled annually over the next several years.

Then, in 1999, Mark was offered a job at Data General by a friend that promised ample training opportunities to transform his raw talent into a seasoned professional sales executive. Shortly after he took the job, the company was bought by EMC, who promptly fired everyone but Mark. “I was their top sales guy in the MidAtlantic because I was the only one left,” he laughs. “In 2000, I decided to talk my way into a job at their biggest competitor, Network Appliance (NetApp), even though I had no business getting that job.”

Now at the fastest-growing startup in Silicon Valley history, Mark was terrified, but he embraced the challenge. That first year, he was named runner up to Rookie of the Year, and he quickly made President’s Club. He finished his bachelor’s degree in 2002 after transferring to George Mason University and then to National Louis University, a phenomenal experience taught by committed business professors. By that time, Mark and his wife had two young sons, and his career was soaring. “By that point, the company was my identity, along with the money, the cars, and the status,” he says. “The momentum was taking care of itself. On the treadmill, I was just enjoying success and not really questioning things.”

In 2007, feeling burnt out and ready for a change, Mark took a job at VMWare, a software startup where he realized that his real talent was more in hardware. “Software sales don’t allow for relationship building,” he explains. “You can’t be looking in the rearview mirror thinking about customer service when you have to focus on the next deal. So in 2007, I switched back to hardware with a data storage company that, again, was acquired by EMC.”

“I thought I was going to die,” he says. “I wanted to die. My only reason to live was my two little kids.

Then, in 2009, Mark faced the darkest trial of his life when he separated from his wife and entered a downward spiral. Sick, depressed, and suicidal, he watched decades of work and progress erode to nothing. “I thought I was going to die,” he says. “I wanted to die. My only reason to live was my two little kids. So I resolved to accomplish three things before I died. First, I wanted to make a million dollars to leave to my sons. Second, I wanted to donate $60,000 to charity to help atone for the mistakes I had made in life. And third, I wanted to run the Marine Corps marathon, even though I couldn’t run at all at that point.”

Mark still vividly remembers sitting outside his doctor’s office, when Stan Middleman, an ultramarathon runner, came on the radio and claimed he could train anyone to run because humans are bipedal and meant to do it. Intrigued, Mark began running and then called up Stan to ask him to be his coach. Under Stan’s guidance, Mark spent eight months training for the Marine Corps marathon, drinking the green drinks Stan swore by. Then, on race day, Mark cramped up at mile 15 and felt he couldn’t go on anymore. “My ex-wife, who I’m still very close with, and kids met me around that mile marker, and when they heard I couldn’t go on, they pulled out sustenance: an ice cold Mountain Dew, some dark chocolate, and a bag of Cheezits,” Mark laughs. “Stan would have killed me if he saw me eating that stuff, but I couldn’t disappoint my kids! And it gave me the fuel I needed to finish the marathon a full hour faster than expected.”

That year, Mark did earn the million dollars, and donated $60,000 to charity. And in the end, he didn’t die after all. “Instead, I found out that when you are maniacally focused on just a few important goals, and when your why is as strong as leaving a legacy for your kids, you can accomplish even the most impossible things,” he affirms. With his new lease on life, as he continued his sales career, he did his own deep work to understand himself, through and through. In the process, he signed up for retreat in Hawaii with a renowned teacher, Allen Cohen. “I was surprised when he called me up and told me I should do his coaching program instead of the retreat,” Mark says. “He told me that ‘Spirit’ told him that, so he offered me my money back if I didn’t like it. I didn’t even know what coaching was, but he convinced me to give it a shot.”

By the third week of the course, Mark was furious with Allen, but he didn’t know why. It soon dawned on him that coaching was the thing he had been looking for his whole life, and exactly what he was meant to do. “My ex-wife and I had always known it; we just didn’t know the word for it,” he says. “I didn’t know how I was going to pull off making the career switch, but I knew I needed to be an executive coach.”

Mark began practicing coaching, putting in the 10,000 hours it takes to truly master a craft. He worked on stillness, presence, and the ability to monitor the physiological clues of his clients. He learned how to be bold, deliberately setting people off to uncover long-hidden blocks. “My goal is to open people up like a can opener, and you have to be prepared for whatever comes out,” he says. “I have watched some of the world’s top coaches do that deep work with their clients, and they’ve helped me do my own deep work.”

All through his career, every time he went to a new startup, Mark’s customers were eager to support him. And true to form, when he launched his coaching practice, his first six clients were former customers who didn’t know what coaching was all about, but believed in him so much that they jumped right in. “In sales, I never succeeded  by being cutthroat competitive,” he says. “I succeeded because I cared about my customers more than anything else and took care of their needs. I think people have been able to recognize that, and they trust me because of it. I’ve always been focused on helping people get where they wanted to go. That’s what being a coach is all about.”

“Humility beats self-importance any day,” he affirms. “I always felt a little less than, so I always worked twice as hard. It’s one of the reasons I’ve been successful.”

Today, as a leader, Mark is sometimes referred to as the reluctant shaman, a bridge between two worlds meant to change people’s lives. “I’ve almost died many times, yet I’ve always sprung back, ready to start over,” he says. “So I’m embracing my purpose and figuring it out as I go.” Part of that purpose is to give back, and Mark donates five percent of his fees to charity, primarily split between veterans organizations and a wolf sanctuary that brings inner city kids to see the animals and learn valuable life skills in the process. A man of iron integrity, he has always kept his obligations and his promises, even when he didn’t have to. And he has managed to turn any disadvantage in life into fuel for his unyielding work ethic. “Humility beats self-importance any day,” he affirms. “I always felt a little less than, so I always worked twice as hard. It’s one of the reasons I’ve been successful.”

In advising young people entering the working world today, Mark urges us to be authentic and vulnerable, because only in this state of honesty can people truly connect to your mission and purpose. “You can lead through fear, but that’s false power,” he observes. “True power is in being able to move people, and that requires authenticity and vulnerability. That’s where true strength is. When you’re vulnerable, you’re invulnerable.”

Deep work begins with finding your core and your center— the foundation from which all else flows.

Beyond that, he underscores the importance of finding your ground. “Figure out who you are and what your foundation is before you go out into the world,” he says. “Deep work begins with finding your core and your center— the foundation from which all else flows. Whether it’s business, relationships, family, or just love of life, that’s where it all starts. Everything else is superfluous. You can improve things in life, but you can’t transform things until you do the real deep work and get down to the core.”

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