These 3 Words Made Me More Resilient at Work

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Kenna Barrett, PhD35

Early in my career, I had the opportunity to work with influential alumni at Yale University. I was a fundraiser at Yale Law School, and my job was to ask for large donations. 

Some of these philanthropists were in the stratosphere of the one percent. They sent their children to private school, joined exclusive club, and took overseas vacations. One even lived on a yacht. I was often asked: how do you deal with people so out of the ordinary? How do you ask them for million-dollar gifts? 

By and large, the people I met achieved their success by challenging the status quo. So no matter how hard my team and I prepared for our meetings, things were bound to not go as planned.

One single piece of advice has gotten me through countless work-related dumpster fires: “expect the unexpected.” 

 This three-word advice was offered by my boss, every time any of us got ready to hit the road. No matter your seniority or industry, you can succeed in your job by expecting the unexpected. Why is this advice so crucial?

The answer comes from the field of aviation studies. Dr. Annemarie Landman researches aviation emergencies. Her work has shown that when pilots on flight simulators are presented with a surprise aerodynamic stall, they have more trouble recovering than when they are given advance warning.

But when we drill challenging situations at work, we usually practice on autopilot. Rarely do we game out responses from the other side of the table, let alone ask a friend to play devil’s advocate, expanding our capacity to respond to unforeseen circumstances.

Here are three steps I’ve since adopted to handle any work surprise and help me expect the unexpected. 

1. Anticipate the unexpected.

Map things out in advance. Think carefully about what questions your interlocutor might pose. When I prepare for a high-stakes conversation, I not only practice my side of the conversation, I practice responding to tough questions from my imagined audience. 

At Yale, we trained on the following objection: “Yale is so rich, why do you need my money?” Our fundraising team brainstormed a response: while large gifts may create new programs, small gifts combine to support the everyday needs of the school. It worked — most of the time.

 Despite how many scenarios you train for, some circumstances cannot be foreseen. This leads to the second step.

2. Accept you can’t plan for everything.

Women tend to over-prepare for stressful work situations, but at some point, your rehearsal must come to an end. Tell yourself, “I’ll handle everything else in the moment.”

Here’s one example. An alum at a high-rise law firm asked me why Yale needed his money. I was about to provide my stock response, but before I drew a breath, he said most of his philanthropy went toward building wells in developing countries. Given that he helped poor people meet their basic needs, I could hardly insist that the second-richest university in the world needed his gift more.

I quickly decided that validating his passion would go farther than pivoting to Yale. So, I asked about the project. I said Yale was proud of alums like him, striving to solve big problems. In the end, the donor recognized it wasn’t a zero-sum game, and made a generous gift to Yale.

But what when something goes really off the rails? Researchers such as Landman are exploring interventions to circumvent our startle response. And that brings us to point three. 

3. Welcome the unexpected when it happens.

Suppose you’re giving a talk to your department’s disruptive thinker – the one who loves picking apart presentations. You know he’s going to throw out questions (no surprise), but when he starts in, it’s still unsettling (you feel startled).

Here’s the crux about the unexpected: even if you’re not particularly surprised that something’s gone wrong, you’ll still be physiologically startled, and you may freeze up, which can spiral into more mistakes. My tactic to prevent succumbing to panic is to tell myself, “Ok, there’s the unexpected!” That little moment enables me to re-frame. 

For example, a few years ago, I was in Mexico City for a series of work meetings. I had to present some material in English. But when I arrived at the engagement, it was obvious that most everyone was more comfortable speaking Spanish. I felt panic coming on, but I mentally reviewed my options: present in English and risk people not participating, or present in Spanish and risk a little embarrassment over my rusty language skills. I decided to present in Spanish. I can’t tell you my grammar was flawless, but my attempt was warmly-received and brought me closer to the people in the room. 

Whatever your profession, you’ll need to navigate change and drama. Following the three-step process above will help you disengage your autopilot, and switch to a problem-solving mindset. The sooner you make that frame-change, the sooner you can start confronting the unexpected. Good luck and enjoy the flight!


This article reflects the views of the author and not necessarily those of Fairygodboss.

Dr. Kenna Barrett is a communications and fundraising coach based in Silver Spring, MD. Kenna has raised millions of dollars in a variety of organizations, from start-ups to world-class universities such as Yale and Johns Hopkins. Kenna teaches fundraising at Sacred Heart University. Coaching and educating are her passions. She loves to work with introverts who seek a seasoned guide to help them navigate the world of philanthropy and persuasive communications. Visit her website at and be sure to join her mailing list!

What’s your no. 1 piece of advice for dealing with the unexpected at work? Share your answer in the comments to help other Fairygodboss members!