Lessons from Flight School that Helped Me Become a Better Entrepreneur
I never imagined that the best business strategies would come to me inside an airplane cockpit.
April of 2020 found me living in Manhattan — suddenly made a ghost town — where I was trying to salvage my import business. It was the peak of the first Covid-19 wave, my primary investor had just declared bankruptcy and my key employee had quit and fled what was then the pandemic's epicenter. As if that wasn't enough, Bhutan — a point of origin for colorfully handwoven scarves for my company Anna in Bhutan — was suddenly, abruptly and seemingly irretrievably closed to all visitors and trade.
Still, there was a bit of luck, because I'd found a needle in a haystack: a seamstress. The only person to answer a frantic stream of emails, calls and voicemails, Paulina helped me turn a small but immovable inventory into (what else?) face masks. For a couple of weeks, I allowed myself to bask in the euphoria that these products, unique and captivating, would generate cash flow and help me stay afloat. My masks were even nominated as an act of local heroism by the local news and information site Patch.
Fast forward two years, and Anna In Bhutan, unable to restock, is temporarily shuttered. But there's a flip side to everything, and a determined entrepreneur can nearly always find it. Pressing "pause" on the company gave me the wherewithal to turn to other goals, and there was one in particular I was eager to devote time to: pilot training.
I'd begun flying after experiencing what is widely regarded as one of the world's most difficult landings. Bhutan's Paro Airport, which sits a cool 7,300 feet above sea level, features a 1.25-mile runway entirely hemmed in by 18,000-foot peaks and plunging valleys. To add to the heart-stopping setting, pilots must dispense with their navigational tech (radar cannot reach the planes) and use the naked eye to land. Across the world, fewer than 20 are certified to attempt this. And, irrationally but indubitably, I knew I was going to join their ranks.
So, I got my pilot's license, scheduled as many flight hours as I could, and commenced my pursuit of the impossible.
What I have found: soloing at 7,500 feet offers peerless mental clarity. I also discovered that a pilot's culture of discipline, proactivity, partnership and communication holds valuable life and business lessons. Here are just a few.
1. Plan ahead
Every year, just under 40 million commercial aircraft take off and land safely. As the global flight total has skyrocketed, airborne accidents have strangely plummeted. In 2020, there was about a 0.000027% chance of fatalities, or one fatal crash per every 3.7 million flights. That's a remarkable survival rate, and it all comes down to planning and learning.
When you have billions of lives and trillions of dollars in equipment at stake, you need to be scrupulously prepared, so even before setting foot in a cockpit, pilots undergo rigorous training. In addition to learning how to fly, they grow accustomed a set of stringent safety regulations that informs their every move.
And that's only the beginning. Throughout their career, pilots must be meticulous, whether they're preparing for their first flight or thousandth. They map their own routes, analyzing weather, terrain and other critical elements. They participate in mandatory annual training programs. Mistakes are closely scrutinized, not just to identify causes but also to develop training and operating procedures that will prevent future missteps.
In entrepreneurship, by contrast, founders are encouraged to move fast and break things. Failures are daily events: After all, they trigger learning, which produces advancement, but then failures in business are rarely fatal.
Aviation's emphasis on premeditated and calculated action gave me a welcome change of pace. Nothing confronts you with the importance of planning quite like the possibility of making an avoidable mistake at 7,500 feet.
While most entrepreneurs will never have to work through engine failure or a crash landing, a good plan can be the difference between the life or death of their ventures. Some of the most common causes of such failure (poor market fit, lack of value, funds running dry) are knock-on effects of poor planning before launch.
It's tempting to fall into the urgency trap when you're in command, but effective planning pays off for business leaders — separating high-impact accomplishments from underwhelming results and spurring enduring success over short-lived wins.
Related: Plan Your Business Plan
2. Set priorities
Before I became a pilot, prioritizing had never been my strong suit. I'd frequently ignore difficult and urgent tasks and spend my days on easy, non-urgent agenda items. A few pages into my flight manual, though, I realized such a strategy wouldn't work in the air — that I would be risking my life by not mastering the emergency checklist or the proper procedure for a crosswind landing.
Shortly after I started flying, I set a new business rule for myself: do the difficult but important things first. I copied the airwork/groundwork model from aviation and used it to divide my day into two blocks:
• Block one consisted of five to six hours of "airwork" — important and urgent tasks that would help me "fly the plane" that day.
• Block two comprised one to two hours of "groundwork" — chores that were not particularly urgent, like answering emails or addressing last-minute requests.
Whenever I was faced with a new task, I'd ask myself: will solving this task help me fly the plane right now or can it wait until I'm on the ground?
3. Remain nimble, adaptable and flexible
Plans are essential, but blindly sticking to them without pivoting when conditions change can quickly become a liability. Pilots know this all too well, as it's a well-documented cause of hundreds of aviation accidents.
Plan continuation bias (or "get-there-itis" as it's known in aviation) is a cognitive bias that compels us to carry out original plans despite changing conditions. Essentially, it's a failure to observe and adapt, can rapidly become a liability.
The pandemic was a global lesson in adaptation. For me, this meant doing so not just once but many times to keep my business afloat. Pivoting to selling masks was easy, but realizing that it was time to stop was a lot harder. It took a heavy dose of humility and self-reflection to understand that there simply wasn't much I could do for my business during Covid, and that my efforts would be better invested elsewhere.
In retrospect, though, turning away from the venture that had been my singular focus opened up richly rewarding avenues. Aside from being an entrepreneur and a professional contemporary dancer, I can now add pilot and podcaster to my resume. I'm also working on a book: Surviving Your Startup—Why Airplanes Crash and Startups Fail. One day I might even find myself touching down on the famous Paro Airport runway. I wouldn't have any of this if I'd decided to stick it out, crashing and burning alongside my business.
I've always known that being goal-driven is vital for success, but the past two years have been a lesson in the importance of pairing that mentality with enough sense to see when it's time to change course or when pulling the plug is the wiser choice. Failures, losses and changes in conditions are all opportunities to pause, review our path and bounce back with a strategy that's rooted in reality and not wishful thinking.
There's no shame in changing yours, and you'll be rewarded for it in the long run with a safe and steady landing.
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