June 2, 2025
Five Lessons You Don’t Learn in School
BY: Sharif L. Gray
When I finished law school 11 years ago, I thought I had a plan. I thought I knew what kind of lawyer I wanted to be, what kinds of cases I would work on—even what my career would look like a decade down the road.
I was wrong.
Nothing unfolded the way I expected.
I’ve won cases I thought I’d lose. Lost cases I was sure I’d win. Changed jobs. Switched practice areas. Took turns I never saw coming—and somehow built a life and a practice I never could’ve imagined.
If you’re just starting out—or in the middle of figuring out what’s next—here are five lessons I learned that might help you along the way.
1. Life Is About Change. Be Open to It.
Years ago, my wife and I spent a long weekend in Richmond. At the end of it, we looked at each other and said, “We’ll never live here.”
Today, I live in Richmond. I co-host a podcast called RVA Trial Lawyers. And I’m beyond grateful to call this city home.
The lesson? Don’t cling too tightly to the plan. Careers evolve. Cities grow on you. You grow, too.
2. The Universe Is Always Conspiring in Your Favor.
I know how that sounds. But hear me out.
Some of the best times in my life began right after the hardest ones. It didn’t make the difficult moments easier—but it gave them purpose and perspective.
In the middle of the hardest challenges, you can choose to say to yourself "I can't wait to see what is going to be great about this."
That mindset doesn’t fix everything. But trust that something good will come from the struggle—because it always does.
3. Be Bold. Everyone’s Faking It—So You Should Too.
Here’s a secret: nobody knows exactly what they’re doing. At least not at first.
The truth is that confidence doesn’t come from knowing. It comes from doing. From showing up, stumbling a little, learning, and showing up again.
So take the chance. Pitch the idea. Ask the question. Stand up and speak—even if your voice shakes a little.
Some of the most meaningful moments in my life didn’t happen because I was ready. They happened because I said yes before I felt ready—and figured it out along the way.
4. Authenticity Is Your Superpower.
The world doesn’t need more polish. It needs more real.
We’re surrounded by curated versions of success—highlight reels, filtered photos, and carefully crafted personas. But the people who truly make an impact are the ones who dare to show up as themselves.
Connection doesn’t come from perfection. It comes from honesty. From the courage to be vulnerable, imperfect, and human.
Gerry Spence once said that the lawyer who connects with jurors on a human level is the one who wins. That’s not just true in the courtroom—it’s true everywhere.
Choose authenticity. It’s your superpower.
5. Your Tribe Matters Most.
You can achieve every goal, hit every milestone, and still miss what matters most if you don’t make time for your family and friends.
Be intentional with your time. Eat dinner with your family. Call your friends. Put it on the calendar—and protect it.
As Clayton Christensen wrote in How Will You Measure Your Life?:
The relationships you have with family and close friends are going to be the most important sources of happiness in your life. But you have to be careful. When it seems like everything at home is going well, you will be lulled into believing that you can put your investments in these relationships on the back burner. That would be an enormous mistake. By the time serious problems arise in those relationships, it often is too late to repair them.
This is the important stuff.