by Jenny Blake
Look for Pilots with Asymmetric Upside
In Antifragile, Nassim Nicholas Taleb talks about the principle of “optionality,” asymmetric opportunities that provide much more to potentially gain than lose.
Look for career pilots that have high potential upside with limited downside. Taking out a second mortgage on your home to pursue a business idea is a very risky endeavor: it may expose you to a great deal of debt, high interest rates, or bankruptcy if your idea does not succeed. On the other hand, taking a small chunk of your savings to pilot a prototype—to see whether there is interest and whether you enjoy it—does not expose you to risk in such a vulnerable way.
Ryan White’s bondage course pilots had asymmetric upside. If he decided not to pursue it as a side business, he would lose only a small amount of money and time. Conversely, each pilot, if successful, would encourage him to move on to the next stage and take on incrementally greater risk, investing more money and time in proportion to any gains.
Conducting a series of small pilots paid off, though not in the way Ryan expected. He realized that this was an aspect of himself that he wanted to integrate more fully and share more publicly, but not as his full-time occupation. As Ryan put it, “It wasn’t the market’s no, it was my own.” He wanted to continue investing in his career as an agile business consultant, not become an Internet marketer for his bondage course.
Rather than stay behind the scenes, Ryan realized that his true value would be in owning his quirks and writing about this side of himself alongside his business acumen. Though nerve-racking at first, this authenticity would bring him an even greater sense of freedom, and could inspire others to share their stories and full personalities more publicly as well.
Ryan has since dropped the pseudonym. His real name is Bob Gower, and he continues running pilots in writing, by sharing his story more publicly, and in his main job as an agile organizational consultant.
Pivot Paradox: Embrace the Slow Build
Sometimes you will want to pilot quickly, acquiring information and feedback as soon as possible, in a lean and scrappy manner. At other times, you may take a more deliberate approach to piloting, aiming not to make change happen within the year, but rather as a long-term strategy for developing your career portfolio. In the former scenario, you may sacrifice quality by moving too quickly, trying to force ideas and income streams to ripen before they are ready.
Theodor Geisel was a cartoonist who earned a living during the Great Depression as a writer and illustrator for newspapers, magazines, and advertising agencies. He dabbled in comic strips, poetry, and propaganda films to pay the bills. In 1936, Geisel wrote his first book of poetry, inspired by his travels; however, publishers rejected the manuscript many times. On his way home to burn it, he ran into a friend who helped him get the book published. When he was forty-nine years old, his first and only feature film was released. It was said to be a critical and financial failure, discouraging him from attempting another movie and prompting his return to simpler, more humorous stories.
In 1954, in response to a children’s illiteracy report in Life magazine, Geisel’s publisher asked him to produce a short book using just 250 of the report’s words. Geisel complied and, at fifty, wrote and published the short poetry-like book. The title is one you might be familiar with: The Cat in the Hat, published under his college pen name, Dr. Seuss.
Dr. Seuss, like most professionals, was not an overnight success. He worked hard at his creative projects and always had several irons in the fire. He piloted by working across a variety of genres, investing more time into what was working and dropping what wasn’t. From his days at the college newspaper drawing comics, to his poetry, to his interest in cartoons and humor, Dr. Seuss evolved his voice and found his audience over time. He worked in advertising to pay the bills while keeping his creative spark alive.
No matter what his day job, Geisel took time to explore projects that were interesting to him. He took smart risks. He continued exploring meaningful work long before he hit commercial success, and long after. I see this story not as encouragement to aim for one tiny peak at the top of a pyramid of success, but rather to enjoy the process of winding around the insides of the pyramid, appreciating every corridor and hidden room.
My late grandfather Harold had a similar but different form of slow-build piloting. His career pivot spanned thirty carefully planned years. He started at the ABC television network in 1949 doing hand-drawn lettering, including those for Batman (Pow! Shazam!) and titles for the Oscars and the Emmy Awards shows. Meanwhile, on the side, he set his sights on building a more sustainable income source that would support his family in later years. His first move was to buy and rehab a house—making him one of the early house flippers, before it became a trendy reality TV genre.
He parlayed the house into a six-unit apartment building that he moved his family into. Then he sold it and applied the profits to a larger building, until at one point he was managing a building with twenty-four units. At fifty-eight, when he was ready to leave his job as ABC’s creative director after thirty-five years at the company, he had a second income stream ready and waiting. Once his second income surpassed his steady income, he had the freedom and confidence to leave ABC at any time.
My grandpa worked until his last days, far beyond retirement, even though he changed the risk profile over time, transitioning into second mortgages instead of buying and rehabbing buildings. His side hustles also allowed him to travel freely with my grandmother for many years, from China to India to Africa to Alaska and to many interesting places in between. He lived frugally and worked thoughtfully, never leaving one income source until the next was ready to take its place.
INCREMENTAL PILOTS WITHIN ORGANIZATIONS
Seth Marbin started at Google in 2006 doing search quality evaluation, which meant reviewing several hundred of the worst-quality websites every day to make sure they did not show up in search results. Needless to say, the job was not a direct connection to what Seth felt was his higher calling.
In 2007, Stacy Sullivan, Google’s chief culture officer, put out a call for team-building ideas, as Google had just doubled in size from 7,000 to 14,000 employees. Seth proposed a companywide service day to help employees connect to each other and their local communities. He had experienced the power of volunteering to break down social barriers during his time in AmeriCorps, and was inspired by Timberland’s Serve-a-palooza, in which the company shut down all operations for one day to perform service projects.
In his spare time Seth recruited a small team (not yet officially sanctioned as one of Google’s well-known 20 percent projects), and together they launched a companywide initiative called GoogleServe. Under this program, all employees could take one day off to volunteer over the course of a designated week. In their first year, the GoogleServe team engaged 3,000 participants across forty-five offices. Over two years, they doubled that number to 6,000 in seventy offices, and the program became recognized as a cornerstone of Google’s community involvement. By 2015, GoogleServe had ballooned to 14,000 participants.
Though it would have been a massive pilot success at that, this was not the end of Seth’s pivot. After three years of leading GoogleServe as a side project, Seth pitched then moved into a full-time role focused on Google’s philanthropy efforts, an internal pivot encouraged by his manager at the time. He is now a program manager on the GooglersGive team, working with a group of ten people focused on year-round employee volunteering and giving programs.
Seth’s trajectory demonstrates several important piloting principles:
Starting with a small test to determine viability and interest.
Piloting without any attachment to this being his full-time job, though he had the vision that one day that might be possible.
Demonstrating increasing adoption and success each year; integrating GoogleServe with his core role after proving its value to the organizat
ion.
Not waiting until an official role opened up to begin, though he did get agreement from his manager that he could work on this initiative as a part-time project.
Creating a shared vision for the company, for employees, and for himself about what would be possible by doing projects in this area.
Seth chose a pilot—then repeated it each year in a bigger way—that led to a fourfold win for the parties involved: Seth got to spend time doing work in line with his values, strengths, and vision; Googlers were thrilled to take time off to volunteer and serve their communities; on a company level, Google advanced its social impact efforts; and thousands of community projects around the world received much needed hands-on resources and support.
REDUCE RISK WITH REDUNDANCY
In engineering, redundancy is defined as the inclusion of extra components that are not strictly necessary for normal functioning, but are included in case of component failure. Although it is not always possible to have complete career redundancy in terms of timing a move, it can help to aim for at least some overlap.
By piloting new ideas simultaneously, in addition to your current source of career stability, you gain important information before betting big on a new direction. Best to avoid panic about your next paycheck in the midst of major change, whether transitioning to a new client base if working for yourself, or to finding a new job if working for someone else.
Pilots can help you build backup systems and test ideas in a low-risk manner so that you are positioned to make your change when you need to. Marisol Dahl, communications director for my business, built her business slowly, learning and piloting little by little. She created career redundancy while in college to maximize available opportunities after graduation.
I met Marisol when she was a junior at Yale. She and her friend Davis Nguyen invited me to speak on campus for Yale’s Master’s Tea series. During my visit I mentioned that I was looking for a community manager for my Life After College platform. We piloted by setting up an internship at first. That worked so well that the following quarter Marisol moved to a paid position, in which I continued to increase her responsibility over time. She was a quick study, detail oriented, and completed every task on time with high quality. In six months, she helped me completely transform my business. In turn, I taught her all the systems and tools I used to run my operations. Within a year, we were in lockstep, each enriching the other’s career ecosystem.
During Marisol’s senior year, I started referring her to friends as a content and community manager. As her schoolwork lightened in her final semester, Marisol took on clients one at a time, raising her rates a little bit each time, piloting her strategy and systems for bringing on additional work. As she developed trust with each client, they also expanded her responsibilities, increasing her hours and project complexity.
By the time Marisol graduated, she had full-time job offers lined up and more potential clients than she could handle. By building redundancy and piloting self-employment while she was in school—each new client a pilot in itself—the choice of what to do after graduation was completely in her hands. She was in a win-win situation: because her résumé was already so stacked with interesting work in social media and online marketing, she could either take a great job with a company or go full time with her own. After taking a few months to explore, she chose the latter.
While many graduates were lamenting their lack of opportunities, Marisol had become a magnet for them by expanding her expertise and existing network, and doing an outstanding job generating results for her clients. She knew that even if she did take a full-time job after graduation, she could have income and fulfillment redundancy by continuing to run her own business on the side.
After getting passed over for promotion on that fateful day in Iraq, Kyle Durand, from the introduction, spent the next ten years building a portfolio of businesses related to his strengths in law and accounting, while still working for the military part time in the reserves as an international human rights lawyer in combat zones. It was this redundancy that smoothed his definitive transition from the armed forces when he fully retired from the military after twenty-seven years of service. Kyle noted that the second major shift felt much easier than the first. “This one doesn’t feel like a big deal because I already went through the really tough work ten years ago,” he said.
On the redundancy of the last ten years, Kyle also pointed out how his diversified portfolio approach has also served him well within his current business activities. “It has been a damn good thing, because other businesses that I have started have fallen off-line,” he said. “The redundant tracks have kept me going. At various times in the last ten years, one of my businesses has been on life support. If that was my only source of livelihood, I would have been dying, too.”
Even in the military, Kyle made a point to gain skills, experience, and education that would transfer into the civilian sector. “When I was young I saw people who were getting out and had no idea what they were going to do, and not many transferrable skills. I never wanted to be in that position,” he said. “That’s why I kept changing course in the military and pursuing advanced degrees in law and accounting. Unlike most people who go into the military and do one career path, I had several.”
Pivot Paradox: The Fauxspiration Foe
Got a tornado of great ideas and good intentions swirling around in your mind, but having a little trouble translating them to the real world? You might be afflicted with fauxspiration if:
You read dozens of articles and blog posts to get inspired! . . . but feel too drained or discouraged to take action afterward.
You read dozens of books to learn a new craft . . . without practicing the craft.
You browse the websites of people you admire to figure out how to do what they are doing . . . only to be accosted by the comparison monster, who tells you that you are an unoriginal hack and everything worth doing has already been done.
You get stuck in analysis paralysis in the name of research or draft mode, which might just be the big bad wolves of procrastination.
Impacters all fall into this trap from time to time, because it comes from a good place—the part of us hungry to learn, grow, share, and make a difference; the part of us that thrives on human interaction and community and wants to live vicariously at times through others’ creativity and courage. It also originates from the part of us tempted to seek endless information to avoid the sting of regret that might come from making a wrong move.
But piloting is not reading, thinking, curating, organizing, outlining, filing, shuffling, e-mailing, hoping, making coffee, drinking coffee, or drinking another cup of coffee. Some of these may very well be part of the creative process, but they do not count for output.
During her pivot from nonprofit work to a career in public speaking, Gigi Bisong pulled herself back from information-seeking mode when she realized that, although her scanning seemed helpful, it was making her feel more stuck and it did not equate to real-world insight.
“I was signing up for every online conference I could find and realized I was even more confused after all the researching,” she said. Her mentor compared this to reading about how to ride a bike, instead of hopping on the bike, falling down, and repeating until she could ride smoothly. Gigi shifted from scanning to piloting by volunteering to speak at smaller events to get real-time feedback, and started trusting her own wisdom for answers about next steps.
TRAVEL PILOTS TO SHAKE UP STAGNANT THINKING
If you are not generating the traction you seek from piloting, travel can be a tremendous way to spice things up.
Immersing ourselves in new cultures allows us to break free from current routines and obligations as we open up to the unknown. Travel teaches us to push past our fears, find courage to explore our inner and outer world, and forces us to turn off autopilot. As a result, we naturally become more present as we navigat
e unknown roads, meet new people, sample exotic foods, and awkwardly fumble through foreign languages.
The adventure and spontaneity of being away from home can foster creativity and a surge of new ideas. The solitude and quiet time provides space for introspection and direction setting. If you choose a destination with a lower cost of living, these trips can create financial breathing room and a longer pivot runway. Meeting others around the world injects friendship and fun. Travel can bring us back to a sense of gratitude and appreciation, opening our eyes to the larger global community by observing cultures vastly different from our own.
I hear the saying “It is about the journey not the destination” ringing in my mind, but sometimes during major changes, it is about the destination. A fresh location can provide exactly the creative catalyst we need.
Many people say they want to travel, even long term, but the accompanying uncertainty can be overwhelming, as can the costs. There are logistical elements of travel: get or renew a passport, save money for the trip, buy a flight, book accommodations.
Other considerations are more subjective: Where should I go? For how long? Who should I go with? How will I take time off work? Or will this be a working trip?
Sometimes we also face a litany of fears: Can I do this by myself? What if something bad happens? What if I don’t enjoy where I end up? How will I find my way around? How will I communicate with others who speak a different language?
The Pilot process works just as well for travel as it does for career change.
Elisa Doucette had never been outside of the United States when she accepted a job with a company of expats, Tropical MBA, as communications director. She got her first passport and a one-way ticket to Bali, and started consulting for them as she traveled throughout Southeast Asia. Her pilot was the length of her first contract, six months, but she quickly proved herself indispensable and loved the lifestyle, so she extended her stay at each six-month checkpoint. Elisa worked with Tropical MBA for three years in this manner before diving back into her writing and editing business, Craft Your Content, full time.