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CREATE YOUR OWN SERENDIPITY

“Difficult to see. Always in motion is the future.”

—YODA

FOR AS LONG AS I’VE known Michael Salort, nearly twenty years now, he has been one of those lucky guys, professionally speaking. I’m not talking about the winning-the-IPO-lottery kind of luck. It’s more like amazing things are constantly happening to him. His career cosmos always aligns, which by the way has benefitted me too—he has hired me three times.

Michael, who favors baseball hats and T-shirts and still has the boyish looks and helmet of hair of the TV news reporter he once was, has pivoted more times in his career than even he can remember. He also has an enviable network of contacts who inevitably seem to resurface years later, leading him to new opportunities. Since first working with Michael as an associate producer nearly two decades ago at the tabloid pseudo-news show A New Current Affair on FOX, I’ve always imagined Michael as the king of serendipity.

Michael’s career began as a local TV reporter while he was still in college in Binghamton, New York. He moved through the local news circuit until he landed a bigger on-air gig at CNBC and later at FOX. He then switched to the producing side for ABC’s 20/20. Those jobs fit the trajectory of a journalist. But then in 2000, Michael pivoted into technology, working for Oracle CEO Larry Ellison’s start-up, the New Internet Computer Company (NIC). Michael landed this gig through his colleague Gina Smith, ABC News’s technology correspondent who was leaving ABC to run NIC and hired Michael to lead its business development and media. Michael hired me too.

Michael, who also had a side passion for writing, wrote a screenplay while working at NIC based on a story he had produced at 20/20. He entered the screenplay in a contest and won, which led him to introductions and ultimately relationships with Hollywood producers. NIC imploded about two years after it launched, but Michael had now positioned himself as a technology executive who understood business development, fundraising, sales, and the start-up world. I, on the other hand, collected unemployment and had a baby. But as colorful career tales go, Michael’s got even more surprising when he was recruited to run the digital arm of supermodel and TV host Tyra Banks’s entertainment company, Bankable Enterprises.

Michael had landed the perfect job for himself. It combined all that he loved, from production to technology. Things continued to get interesting for him. As Michael was evaluating different ideas to grow the Tyra empire, he found a folder in the office called Modelland—a young adult book concept that had been scribbled down on the back of some napkins. Unlike the other ideas Tyra’s team was considering, from branding candy to launching a talent management business, this was something that Michael was into. In fact, he was so into the concept that he offered to write the treatment for Modelland himself. Tyra was thrilled. The idea had been percolating for years, but no one was pushing it through. Within a week of finishing the book proposal, the idea was sold to Random House with Michael ultimately signing on to write the young adult fantasy novel about girls, friendships, and a wacky school where beautiful girls do crazy things. Modelland was published in 2011 and became a New York Times best seller.

Five years and a dozen projects later, Michael is currently writing a fictional memoir about a transgender married man, told from the wife’s perspective. He was paid a six-figure advance from the man’s wife, whom he had met through Gina Smith, the former ABC tech reporter who had hired Michael at NIC seventeen years earlier. Talk about coming full circle. And that’s Michael’s secret sauce. He nurtures his networks and stays top of mind. People remember him because he makes sure he’s not forgotten.

As Michael’s friend, I’ve been impressed, inspired, and even envious of his extraordinary career pivots. I’ve marveled at his ability to seamlessly expand his professional identity and get paid well for what he loves to do. There’s no question that Michael is incredibly talented, charming, and agile. Married and the father of three, he has a full personal life too. So how does he do it? Is this a gender thing? Or is there a recipe for making this happen?

ENGINEERING SERENDIPITY

It turns out that Michael may be the king of serendipity but not in the way I had always thought. To understand what seems like Michael’s magnificent good fortune, we need to take a closer look at what serendipity is all about.

As trends go, serendipity has become fashionable in Silicon Valley. At the annual South by Southwest (SXSW) Interactive Conference in Austin in 2013, thirty thousand techies, designers, creators, investors, and entrepreneurs met to discuss tech trends and best-in-class philosophies for start-ups and innovation. Several panels focused on serendipity and the importance of unexpected connections. While most of us think about serendipity as a “happy accident,” the word’s origin is more nuanced. It comes from a Persian fairy tale where three princes of Serendip “were always making discoveries, by accidents and sagacity, of things which they were not in quest of.” This fairy tale, discussed in a now much quoted letter written in 1754 by British aristocrat Horace Walpole, has suddenly become legend in Silicon Valley.¹

The entrepreneurial and creative classes are particularly enamored with this concept because of their understanding that the history of innovation and discovery can be traced to certain predictable situations. Steven Johnson, TED speaker and best-selling author of Where Good Ideas Come From: The Natural History of Innovation, has found systems in place that make it possible for great things to occur. Johnson says that it is almost never the lone researcher, scientist, coder, philosopher, artist, or academic who suddenly has that transformative lightbulb moment. Those are the stories that make for good tales. But the reality of an idea’s genesis nearly always runs deeper. Johnson argues that the image of a scientist in a lab having a eureka moment is simply a myth. It turns out that the mash-up of creative collisions mixed with a little chaos, good timing, and human networks can spark the perfect storm for amazing ideas to take off. Engineering that perfect ecosystem to make incredible things happen is the obsession of the tech world. Simply, everyone wants the recipe to serendipity.

Companies like Google, Zappos, and even advertising agencies are trying to engineer serendipity. From the architecture of their buildings to where they put the beer machines to designated time for employees to focus on their passion projects, everything is designed to enable these seemingly chance innovations. Substantial research supports the concept that the best ideas bubble up when people have the opportunity to mingle and bring different ideas and skillsets to the table. This isn’t just a zeitgeisty thing to do—it helps the bottom line.

All of this makes sense. Ideas build upon ideas. Anyone who has ever sat in a productive brainstorming session knows the concept well. There can be tons of bad ideas, but then something is triggered, sometimes from a random thought or idea that had been percolating in someone’s mind for a while. It mixes with other ideas and BOOM—a truly fantastic concept can take shape.

PUSHING BOUNDARIES AND CREATING OPPORTUNITIES

Years ago, Google famously created a 20 percent time program for its engineers, called “Innovation Time Off.” For every four hours that engineers spent working on a project for Google, they were required to spend one hour on their own passion project. Having the mental and physical space to let ideas brew is not only liberating, but it is also one of the fundamental pieces to creating the right atmosphere for innovation. This space to let creativity cook can also lead to the “adjacent possible,” a concept coined by theoretical biologist Stuart Kauffman to explain biodiversity, among other things. It’s a prescribed way in which biological progress happens. Kauffman describes this as the “untapped potential of what could be.” In his book, Steven Johnson takes this idea further and applies it to society: “The adjacent possible is a kind of shadow future, hovering on the edges of the present state of things, a map of all the ways in which the present can reinvent itself,” he writes.²

Johnson describes it as a house that magically expands with each door that you open—one room leading into more rooms. Those rooms are the adjacent possible. The idea is that the boundaries expand as you explore them. Successful engineers, scientists, entrepreneurs, academics, and artists all push boundaries, and it’s these discoveries that lead to things like penicillin, Post-its, and Gmail.

So how can we make the “adjacent possible” in our careers? How do we push boundaries so that doors will open and lead us to unexpected opportunities? How can we orchestrate those unexpected-yet-positive outcomes and drive our own serendipity? “The trick is to figure out ways to explore the edges of possibility that surround you,” writes Johnson. “This can be as simple as changing the physical environment you work in or cultivating a specific kind of social network, or maintaining certain habits in the way you seek and store information.”³

THE SERENDIPITY FORMULA

Serendipity relies on a social network too. If ideas live in a vacuum, they will rarely come to fruition. A combination of forces take an idea and make it real. Social and professional networks can help drive ideas forward, and on an individual level they can give you the emotional or professional support you need. “There’s the serendipity that takes place in your own head and then the serendipity from social,” says Greg Lindsay, author of the upcoming book Engineering Serendipity. “It’s really the mental state to put yourself into a situation where you might be surprised or you’ll have an unexpected goal. But you also have to have the mental preparedness to recognize both the moment as significant enough, and then be able to actually exploit that moment. It’s a process.”

This is where someone like Michael Salort thrives. He understands the process and sees the opportunity. He actively puts himself into situations where an unexpected moment of good fortune can occur. He doesn’t only go to events in the tech space, he also frequents entertainment functions. He attends screenings and book parties and makes sure to stay for the after-events. Whether it’s another job opportunity or just a good connection for his professional network, Michael is mentally prepared for these moments because of his experience, diverse skillset, and ability to read the room.

Michael even has his own formula for serendipity: = serendipity. In Michael’s formula, a is “availability,” c is “connections,” f is “fear factor,” L is “location,” and v is “vision.” He says that vision should be the number one because it needs to be singular and focused. If you have more than one vision, the focus gets diluted. “The key is to make yourself available and create connections, and then take out the fear factor,” Michael says. “You multiply this times location. If you want to work in Hollywood, you can’t live in Nebraska.”

Remain Open and Ready

Michael agrees that your mental state is critical to creating professional serendipity. It starts with being open to new ideas and pushing your own boundaries so you can drive those opportunities and be able to seize the moment if something presents itself. And don’t underestimate the ability to work the room. “You need to be skillful in social and professional settings and be incredibly charming,” Michael says. “Even if it’s not entirely natural, you have to push yourself to the highest possible charm level.”

Finding ways to marry what you do with others’ talents and push outside your own skillset is important. Michael can be at an entertainment event talking to someone about a script that he’s developing, and then segue to the fundraising he’s doing for a tech start-up that streams video. He plays matchmaker with people in the room and is always thinking about how what he does and who he knows could somehow benefit the person he’s talking to. He broadens his personal narrative so he can find more connections with people he meets—connections that at first may not seem so obvious.

There’s no doubt that this is an art. But it’s something that you can learn to do, even if it doesn’t come easily at first. It’s not just working the room, but understanding how what you do fits in and how you can take what you know and apply it in different directions. “Be receptive to playing with other ideas, and look for how they branch with what your real core skillset or industry is,” suggests Greg Lindsay. “Then once you find this weird hybrid, the final step is the ability to recognize how to use your personal network to amplify these ideas and figure out who can help you. The ability to discover people outside of your core network and develop them is really important.”

Networking is a strategic skill. Not everyone likes to do it. In fact, many people hate it. Michael abides by the give-and-take principle of networking reciprocity: I scratch your back, you scratch mine. “You have to approach an event or a dinner party like a barter system, even though you’re not saying it that way. It’s like you’re swapping eggs and milk,” Michael says. “You need to show your eggs first and see who is willing to offer something, and present your value quickly without looking needy. You want to be perceived like you have a surplus of goods, and you want to get something out of it too.”

Social Serendipity

For years, Michael would invite me to have drinks with him and other colleagues after work. I usually declined. I had young kids at home and didn’t want to miss bedtime. After working all day, an after-work event seemed like more work and something I was not really up for. But Michael always saw these events as an extension of his day—perhaps the most important part of his day. It was at these cocktail parties and meetups that his network developed and flourished.

As Michael was networking, he was creating what Steven Johnson would call “a liquid network.” Michael was maximizing the adjacent possible—opening doors for himself that would lead to all types of places. “Social serendipity requires getting out of your comfort spot and dabbling in other areas,” Lindsay says. “Go to these strange events that are outside of your comfort zone, which also goes along with the notion of taking time for yourself. Invest the time and energy, and focus on who is going to be at these events.”

Michael also gives himself the mental space to work on all kinds of projects—from purely creative to business-driven. He connects with his network to help drive those ideas through. He is always leveraging one project into something new. A script Michael wrote five years ago may be dormant until he meets a new producer and pitches the idea, and suddenly it has legs again.

Strategic Serendipity for Women

It turns out that Michael’s good fortune was not wild luck at all, but actually a proven strategy that can be analyzed and measured—one that historically works. But do these principles translate to women? Or to moms with children at home? Or is our reality just different? Aside from opting to go to the cocktail party after work rather than getting home for bedtime, most moms I know aren’t noodling with a host of creative projects. They just don’t have the mental bandwidth—or the time or support—at least not when their kids are young.

“I think women in general are penalized in American society by not being able to take time for themselves to explore and think and play, particularly working mothers who are forced to maximize efficiency and who are focused on checking off every task,” Lindsay says. “I think women need in general to carve out space for themselves to really be reflective and explore all of these things.”

And that, of course, is the rub. We need the time to take time to engineer our serendipity. I don’t love networking. I’ve never done enough of it—or enough of it all that well. When my kids were little and I was working at a PR agency, part of my job was to host and attend media events at night. I dreaded them, but made a conscious decision that if I had to miss bedtime and not see my kids, then I needed to double down and make sure I made the time worthwhile. At each event, I was determined to walk away with at a minimum two new media contacts. In the PR world, your relationships with editors, reporters, and TV producers are your career currency. If I had to miss out on my kids, I would maximize my career growth. I was strategic and intentional about it—spending time to figure out who was in the room and how I would connect with them.

I think most working moms try to become more efficient at work because we reprioritize what’s important. It can be hard to figure out the value of an optional after-hours networking event. We no longer have the luxury of time to get a few cocktails, mingle, and hope to meet someone who can (maybe, one day) help us. It’s too theoretical. A crapshoot. And if that event or conference costs money or requires travel, it may be even more difficult to justify. So we need to pick wisely, act strategically, and like Michael does, stay visible—even if it’s not as often as we would hope.

PASSION AND PIVOTS PAVE THE WAY

Fifteen years ago when Michael was first getting into the tech space, Aminatou Sow was first learning to speak English. Born in Guinea to parents who were diplomats, Amina grew up in West Africa and Europe and didn’t speak English until she was a sophomore in high school. She went to the University of Texas at Austin in 2004 where she immersed herself in everything American, from pop culture to politics. When she graduated, she moved to Washington, DC, not having a job or even knowing anyone. Amina got an offer to be a press intern in then Senator John Kerry’s office and was thrilled about the internship—only to be shocked to discover it was unpaid. After putting herself through college, there was no way she could work for free. “I had to go back to the drawing board about what I wanted to do,” Amina says.

It was 2008 and the recession was in full force and taking a toll on recent graduates. Many of Amina’s friends were unemployed. Amina took a job at a toy store in Georgetown.

“Nothing could crush your ego more than being in a status-driven town and not having a job in the industry that you want,” Amina says. But she was optimistic and took advantage of the flexibility that came with working at the toy store. It gave her time to research different jobs, and she sent out her résumé all over DC.

At the end of that winter, Amina interviewed at the think tank New America, then called the New America Foundation. The only opening was an admin position, but Amina took the gig at the front desk and within a year moved over to its communications department. Amina, who cared about policy issues, soon realized she had a real knack for translating wonky policy into civilian engagement and making it a fun experience. “I was one of the few people who knew how to do website stuff. So I decided that was going to be my talent,” Amina says.

Seeking New Challenges

The social media work she was doing took off, but Amina realized there wasn’t really a place for her in the think tank world. She knew she wanted to learn more about social media and social engagement, so she moved to a media strategy firm. From there, she was approached by the Iraq and Afghanistan Veterans of America (IAVA), a nonprofit organization that recruited her to lead its digital engagement. She didn’t know anything about the U.S. military culture, but as a child of diplomats Amina felt an instant affinity toward military families. She also embraced the challenge. “When I was interviewing, I said, ‘If you can get me to care, you can make anybody care.’ I think that’s how I got my job.” Amina says.

Amina helped get legislation supporting veterans passed through Congress. “It’s the job that I am most proud of,” she says.

In the meantime, Amina, like Michael Salort and the Google engineers with their 20 percent Innovation Time Off, always had a passion project on the side. For Amina, it started with blogging in 2009 about the hunky White House Office of Management and Budget Director, Peter Orszag. Orszag defined the nerdy cool of the Obama administration, had a devoted following in DC—a following that read Amina’s blog Orszagasm.com—and was profiled in The New York Times.

“One of my steadfast rules, no matter where you work: You need one project that’s just for you and that’s fun to do,” Amina says. “I always had a knack for doing one fun thing on the side. It keeps you sane and keeps you happy and helps you flex your muscles and learn about other things.”

“Don’t Tell Me What Women Can’t Do!”

In 2011, Amina was working at a digital firm with her friend Erie Mayer and launched Tech LadyMafia, a listserv to support and connect women in technology. This was a place to talk about salaries, jobs, or simply what they were doing in the tech world. Tired of hearing how unfriendly the tech space was to women and how few women worked in STEM, Amina wanted to do something about it.

“People kept telling us that there were no women in tech, and I thought that was crazy because I knew two women who were applying to be NASA astronauts,” Amina said. “So we sent an email to twenty people and now it’s grown to two thousand people around the world.”

In 2014, Amina was at a party with her friend, the writer Ann Friedman, when a man told them that women don’t podcast because they don’t have enough patience to create them. “Nothing makes me do something faster than telling me that women don’t know how to do something,” Amina says. So this conversation, sparked by a pseudo dare, galvanized Amina and Ann to launch and cohost what became the wildly popular Call Your Girlfriend—a weekly podcast where smart women chew on interesting, timely topics ranging from politics to pop culture. With nearly 150 thousand downloads, the podcast has become a sensation, spreading largely through word of mouth and the tremendous press it has received. What started as a labor of love has become one of the go-to podcasts for women.

“We’ve been really surprised by the response. It confirms people want more female voices and people care about things that are presented in a casual and fun tone,” Amina says.

Now thirty-two, Amina lives in San Francisco, and after leading political and social impact marketing for Google, has recently started her own consultancy. Google is now a client.

Perfect Timing for Serendipity

In Malcolm Gladwell’s best-selling book Outliers: The Story of Success, he describes how timing impacts success. For Canadian hockey players, being born between January and March is the magic window if you’re looking to turn pro because of the calendar cutoff for youth hockey league teams. The advantage goes to the older kids, who are usually the bigger kids, even in those early years of playing. And for tycoons of industry including the Rockefellers, Carnegies, and J.P. Morgan, Gladwell finds that simply being alive at the right time can greatly increase your odds of success. “Success is not a random act. It arises out of a predictable and powerful set of circumstances and opportunities . . .” writes Gladwell.⁴

In a very Outliers kind of way, Amina believes that she was born at just the right time—and she’s probably right. Her timing for entering the world of social media was perfect. “If I were born even a year later, I don’t think I would be where I am,” Amina says. “I’m really cognizant of that. I think it was the right moment at the right time combined with not having too much fear.”

But as we’ve seen from serendipity, Amina engineered her own “happy accidents” by maximizing good timing with the opportunities that came her way and nurturing relationships and networks. She sees the “adjacent possible” and pushes her own boundaries, which ultimately open up still more opportunities for her. “I’m such a proponent that you can do any job, aside from flying a rocket, with proper training and proper curiosity and just applying yourself. It always surprises me how many times people say, I could never do that. And I’m like, actually, you probably can.”

Without realizing it, Amina is also applying Michael Salort’s formula for serendipity. She makes herself open to new experiences and will take on projects outside of her skillset. She doesn’t let fear prevent her from exploring something new. In fact, she loves the challenge. And Amina’s approach to her career is exactly what experts say is the new way to think about our jobs.

“For me, it’s more important to stay relevant than it is to worry about a career arc,” Amina says. “I think about what are the skills that people will still need and what are the things that are useful? Even in the work that I do at Google or the work I do in consulting on the side, I’m finding that people come to me about things that are completely outside of my skillset. People will say, ‘You seem like a capable, connected person. What do you think about this?’ Thinking about your career in terms of what problems do I want to solve and what do I want to be at the heart of?—and then seeing, well, here are the skills that I have and here is what I want to build on, and how can I contribute to all of those places?—is probably a better way to look at your career.”

“When You Shine, I Shine”

People who know Amina agree that she defines badass. She moved to America on her own just three years after learning English. By the time she was twenty-eight years old, she was recognized as one of Forbes’s “30 Under 30” for technology. Her innovative work has supported US military veterans, and her eclectic group of interesting friends includes actress Lena Dunham. But what further defines Amina is that she loves encouraging women to take chances. One of her goals has been to create a stronger and more connected squad of women and to codify ways to help other women succeed. For Amina, it’s natural. She’s smart, social, and fierce. She is also incredibly generous.

The Tech LadyMafia’s operating principle is Shine Theory: “When you shine, I shine.” Forget about female competition where we loathe women who seem more together and accomplished than we are. This is about having the smartest and strongest women in your corner. Instead of feeling intimidated or threatened by an intelligent, witty, successful—and yes, even gorgeous—woman, befriend her. The idea is that when you look good, I look good.⁵ This flips the catfight concept on its head. Women are not competing against each other for a limited slice of the pie. Instead, the ethos of Tech LadyMafia is to support the sisterhood and pay it forward. If you turn something down, you should pass it along to someone in your network. “It’s an easy way to hook up other women with opportunities,” Amina says.

Ask, Offer, and Receive

They also have a rule called “ask and offer,” introduced by Tech LadyMafia member Natalia Oberti Noguera. Any time you go to a Tech LadyMafia event, you’re supposed to ask for one thing, whatever you may need help with, and then you give something in return. Amina says that women often don’t like to ask for help and appear needy. They can also be a little squeamish about offering something in return. “Even the act of saying it out loud to each other has been a huge game changer,” Amina says.

Amina wants to reform the way women approach networking. Instead of seeing it as something obnoxious and aggressive, she wants women to have the space to brag about themselves, talk about their work, and yes, be self-promotional.

“When men get together, all they do is talk about work and that’s how they know what’s going on and what they need help with,” Amina says. “When women get together, the talk is often about caretaking. When it comes to work, we never want to be seen as a burden or needing help, and I think professionally that attitude is a huge detriment. So I think that codifying asking and giving and talking about ourselves in a different way when we hang out with each other has been really important. And knowing that there is space to do that always helps to put people front of mind. When you feel that you are giving as much as you’re taking, then what’s the harm?”

In The New York Times best-seller Give and Take: Why Helping Others Drives Our Success, Adam Grant writes about giving as a new form of networking. This is not about the swapping eggs for milk reciprocity that Michael describes, but one in which the giver has a more long-term goal in mind. The approach: I’m here to help you because helping you may help me down the road. It may not, but it probably can.

“In traditional old-school reciprocity people operated like matchers, trading value back and forth with one another,” Grant writes. “We helped the people who helped us, and we gave to the people from whom we wanted something in return. But today, there are givers who are sparking a more powerful form of reciprocity. Instead of trading value, these types of givers are looking to add value.” And giving promotes giving. “Giving, especially when it’s distinctive and consistent, establishes a pattern that shifts other people’s reciprocity styles within a group.”⁶

Amina is the quintessential giver, and she has created a network that could be a way to add value for everyone, not just to claim it for herself. “That’s why I think the network is so important. Because if you’re doing it all by yourself, you’re doing it in a void—but if you have the power of a list or the power of other women driving you, there’s so much more that you can achieve,” she says.

Networks like Amina’s have tremendous long-term impact. They are redefining the rules of engagement for women. They are showing women how to brag and ask for help and share their resources. They are encouraging women to share opportunities and pass along projects they may be passing on. We shouldn’t hoard, we should give—because when you shine, I shine.

HACKING NETWORKING EVENTS AND GETTING VISIBLE

Amina’s model is a more female-friendly one than the traditional post-conference cocktail party events that Michael navigates so well. But nonetheless, those industry events are where serendipity can be created and new opportunities discovered. The rub is that women often don’t have the time to go to these events. We may even underestimate their importance. The key then is to be selective and strategic and sometimes even force ourselves to get out there, because visibility is the first step.

Conferences, many of us know, can be a time suck and a waste of money. Greg Lindsay recommends trying to get a visible role at a conference. Snag a speaking part if possible, or volunteer to help organize the conference and be involved in it. This is the perfect way to get connected and be introduced to some of the key players attending. Being a participant, rather than just an attendee, immediately elevates your profile and opens doors. The after-conference networking parties are also vastly more important than sitting in the sessions. Again, finding a conference organizer who can make some introductions for you is the perfect way to maximize these events without having to spend a day or more silently listening to speaker after speaker.

There are other places to create these connections too. Now, more than ever, there are opportunities to get out and mingle in settings that inspire fortuitous interactions that can lead to our own breakthroughs: new business ideas, projects, or other creative endeavors. Lindsay suggests joining a shared workspace like WeWork and really leaning on the community managers to introduce you to new people. These environments are designed for collaboration and cross-pollination of skillsets. You can discover the adjacent skills you want to learn and open your eyes to other possibilities. “As far as social serendipity is concerned, there’s a whole new thing that’s available to women now, which is real shared work environments with peer groups and meetups and all sorts of interesting networks,” Lindsay says.

Knowledge is power, and knowing that you can manage your own good fortune—at least to an extent—is empowering. By putting yourself in the right places and putting energy into making strategic contacts and opening yourself up to what’s out there, you can become the queen of your own serendipity.