When I was in business school, we regularly examined case studies that began with some version of the same sentence: “The founder was losing sleep.”
It happened so often that it almost became a cliché. The point, of course, was to signal that the business had reached a pivotal moment. It could be that sales were declining, cash was running out, or a competitor had entered the market. A difficult decision had to be made.
Even though the stories were based on real people and real companies, they still felt hypothetical. They belonged to someone else. And as students, we had the luxury of distance and objectivity.
We could debate strategy over pizza and snacks because we weren’t the ones wondering whether payroll would clear or whether our next decision might determine the future of the business.
Then, for many of us, business school ended and real life began. We became the business leaders we had been reading about. And suddenly those case studies don’t feel so hypothetical anymore.
Over the past few weeks, I’ve had several conversations with business leaders who are navigating their own difficult transitions.
One colleague described leaving a successful corporate leadership career to start his own consulting practice. His business is thriving today, but he admitted something that immediately caught my attention. “For the first year and a half, I would wake up in a cold sweat. I kept thinking, ‘When is this business finally going to come together? Did I make the wrong decision?’”
Another colleague shared a different story. After unexpectedly losing a position where he had become comfortable, he found himself rebuilding his career later in life. “It has taken more than a year,” he told me, “but only now are things starting to come together.”
As they talked, I realized I wasn’t just listening to their stories. I was remembering my own.
When I left the predictable comfort of a weekly paycheck to launch Adams Learning, I often described those early months with a bit of exaggeration. I used to say that “for eighteen months, I didn’t sleep.”
Of course, I slept. Just not very well.
Whenever one project ended, I found myself wondering where the next opportunity would come from. Would the phone ring? Had I made a terrible mistake? Those were the nights when my mind refused to turn off.
Eventually, the phone would ring, and I would get busy again. Then that project would end, and I would be anticipating a repeat of the anxiety. But after about eighteen months, something interesting happened. The anxiety was not nearly as bad as it had been before. It didn’t disappear because my business had become perfectly predictable. Rather, it disappeared because I had lived through enough uncertainty to trust that I could figure out how to survive it.
The adversity hadn’t gone away, but my relationship with adversity had changed.
Starting a business, accepting a promotion, changing careers, relocating your family, taking on an executive role … these moments often make you feel like you are sitting at a poker table in Las Vegas. At some point, you push your chips into the middle and make a big bet. After that, there is little you can do except watch the cards play out.
I think all of us can agree that the feeling is uncomfortable. It always has been, and it always will be.
During my doctoral research on trust in organizational leaders, I discovered something that helped explain why some leaders inspire confidence during difficult times while others create anxiety.
Participants consistently described trusting leaders who remained calm under pressure. They valued leaders who were steady. They used words like calm, cool, and level-headed. Even when the situation itself was uncertain, the leader wasn’t – or didn’t appear to be.
On the other hand, distrust grew when leaders responded to adversity in ways that were impulsive, emotional, or reactionary. Employees described these leaders as rushing to judgment, overreacting, or allowing emotion to replace thoughtful decision-making.
Another pattern emerged around optimism. Trusted leaders didn’t pretend problems didn’t exist. They simply communicated confidence that the team could work through them.
Distrusted leaders, by contrast, seemed to focus almost exclusively on what might go wrong. They magnified obstacles while overlooking possibilities.
That difference mattered to those employees. Not because optimism magically solved the problems. It was because people are looking to follow someone who can help them believe there is a path forward.
This lesson about facing adversity applies just as much when we look at ourselves in the mirror. When we’re facing uncertainty, we become our own leader. The voice in our own head can either become reactionary and pessimistic … or steady and hopeful.
The circumstances may not change overnight, but the way we walk through them can.
If you’re in one of those difficult seasons right now, remember this: The discomfort you’re experiencing doesn’t necessarily mean you’ve made the wrong decision. It may simply mean you’re living through the same kind of chapter that countless leaders have experienced before you.
You are not alone. Stay steady, and choose optimism. Keep moving forward.
Eventually, you’ll discover that what has changed isn’t the uncertainty around you. What has changed is you. And one night, almost without noticing it, you will be sure to get a good night’s sleep.