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I started my legal career at one of the world’s largest law firms on September 17, 2001.
I was supposed to be an M&A lawyer, but after 9/11 everything changed. Planes were grounded, markets closed, and the economy—still reeling from the dot-com crash—was teetering. Companies were preparing for Chapter 11, and I was shifted into the corporate restructuring group.
It was intense, and I was unprepared. This was my first real job. I hadn’t taken a single bankruptcy class in law school, and everyone around me was too busy to teach. It was trial by fire.
The next four months were a blur of all-nighters and overwhelm. I had too much work and too little confidence. I kept telling myself—and my wife, whom I hardly saw—that things would get better, but I didn’t know that to be true.
Eventually, they did. The world steadied. Work became manageable. I learned to think through problems, stay organized, and take pride in progress. I became a better lawyer.
But I also made plenty of mistakes. The biggest was not stopping occasionally to recognize how far I’d come. Each new level became my new normal. I was moving ahead, but it didn’t feel that way.
The point is: in the moment, it’s easy to fixate on your struggles if you never look back. When you do, you realize the good things didn’t happen despite the bad—they happened because of them. Failure isn’t the opposite of success; it’s the path to it.
Discomfort Is the Signal of Progress
In 1923, Babe Ruth set records for both the most home runs and the most strikeouts in a season. If you want to hit the ball, you have to swing—and sometimes you’ll miss.
The same principle applies to law. The only way to take a good deposition is to take a bad one first. The only way to win new clients is to hear “no” many times along the way.
“Failure,” then, is simply feedback. It’s learning in motion. As Robert F. Kennedy said, “Only those who dare to fail greatly can ever achieve greatly.”
But even when you do your best, the outcome isn’t always in your control. As Judge Raymond Kethledge once put it: “You shouldn’t get too focused on outcomes. Focus on doing your best—writing the best brief you can, preparing as best you can—and then step back emotionally. Don’t let your highs get too high, or your lows get too low. After doing your best, you can’t control what the court does.”
That mindset—focusing on process, not outcome—is at the core of growth. It allows you to keep showing up, even when the result is uncertain.
A Bit of Fear Means You’re on the Right Path
What makes failure so uncomfortable is fear—fear of judgment, rejection, or simply not being good enough. But fear isn’t a sign you’re on the wrong path. It’s usually a sign you’re on the right one.
Fear stops many lawyers from stepping up for tough assignments, sharing their ideas publicly, or pursuing business development opportunities. They tell themselves they’ll act “when the time is right.” But the time is never right. Years pass, and nothing changes.
The truth is that the only time that’s ever right is right now. The steps that lead to growth—pitching work, writing thought leadership, taking the lead in a meeting—always come with discomfort. Waiting for the fear to fade is a losing strategy.
At some point, you have to be more afraid of staying stuck than of trying and failing.
A Simple Framework for Moving Through Fear
Identify what you’re avoiding
Name the fear or belief that stands in the way
Do the thing you’re avoiding
Learn that your fears were exaggerated
Update what you believe you’re capable of
Simple, not easy. But every time you face fear, it gets a little easier. You learn that taking the plunge isn’t as scary as you thought, so you do it again. Eventually, courage becomes habit—and habit becomes growth.
The Other Side of Fear
Every meaningful step in my career began with fear. But I’ve learned that fear is rarely a stop sign—it’s a green light. It means you’re heading somewhere new.
As Tim Ferriss once quoted Samuel Beckett: “Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”
You won’t believe what you can accomplish when you have the courage to fail better.
Jay Harrington is president of our agency, a published author, and nationally-recognized expert in thought-leadership marketing.
From strategic planning to writing, podcasting, video marketing, and design, Jay and his team help lawyers and law firms turn expertise into thought leadership, and thought leadership into new business. Get in touch to learn more about the consulting and coaching services we provide. You can reach Jay at jay@hcommunications.biz.