Deep Dive

Changing Your Perspective on “Intimidating” People

This newsletter might contain the most important message I’ve shared so far.  Especially if feeling intimidated or unworthy is standing between you and the legal career (or life) you want.

Here’s the one message. It’s simple, but it can be a game changer if you let yourself believe it:

That experienced professional you think of as an absolute rockstar — the one who seems to succeed effortlessly, who’s been practicing law since you were learning to spell your own name, and who somehow makes everything look easy — they were once exactly where you are. And even today, they are still just a person.

We’ve all been intimidated by someone (or maybe even everyone!) who seems to have what we don’t. The senior partner who exudes confidence. The CEO of a nine-figure company who always looks perfectly put together. The general counsel who walks into the boardroom like she owns it.

And when we feel that way — small, uncertain, maybe even invisible — our instinct is often to shrink.

We may feel that we should keep our mouth shut in meetings. Soften our recommendations. Re-draft the email for a fourth time, because the first three didn’t feel polished enough. We assume we’re not ready yet. Not impressive enough. Not ‘that kind’ of lawyer.  

We write ourselves off before we ever raise our hand for the project that excites us or ask for the opportunity we truly want.

But here’s the truth: that person who intimidates you? They’re not superhuman. They’re not perfect. And they have insecurities and flaws, just like the rest of us.

I’ve known this longer than most, because I got to see it up close from a young age. 

Both of my parents were Big Law partners. They met at the office, so it’s no surprise that many of their closest friends — people I grew up around at dinner tables, on family trips, and at holiday parties — were also high-powered lawyers and judges. These were people who made big decisions, held real influence, and earned the kind of professional respect most lawyers aspire to.

Even as a young adult, when I had the opportunity to join casual summer dinner parties with my parents and their friends, I wondered aloud to my husband: will our lives be as exciting, and will our friends have made the kind of positive difference in the world that the people around this table have?

It’s still too soon to say, but I sure as heck know we’ll try. 

I looked up to them. I also knew them; not just as professionals.

I saw them at home, with messy morning hair. Not functioning before coffee. Telling jokes that fell flat over dinner. Looking completely ordinary, occasionally even a little sloppy, after shoveling the walkway following yet another Boston Nor’easter, or on a sweaty, sandy, Saturday afternoon at the beach.

They were brilliant, yes. But they were also human.

That early window into “impressive” people being real people stuck with me. And it’s come back to me again and again in my career.

Early in my legal career, I worked with a woman who, from the outside, seemed like she had it all together. She was polished and smart, articulate, confident, and widely respected. She walked into meetings with quiet authority, always prepared and poised. I was intimidated. Really, truly intimidated.

But over time, as we worked more closely, I started to see another side. She was awkward in casual conversations, and the confidence she projected so effortlessly in front of a room full of executives seemed to vanish in smaller, more personal settings. She clearly worried about small talk and often looked drained by the effort it took to appear perfectly composed.

That experience was a powerful reminder that people are complicated. The same person who intimidates you might be the one silently wrestling with their own discomfort. With their own insecurity. With their own version of “not enough.”

Understanding this isn’t just about confidence.  It’s about clarity. 

Because when you stop putting someone else on a pedestal, you create space to show up as their peer. To speak with authority. To disagree respectfully. To own your judgment. And to be taken seriously, which happens most naturally once you’ve finally decided to take yourself seriously.

This shift is especially important in-house, where the dynamics can feel exaggerated. You're often the only lawyer in the room. You’re surrounded by brilliant, accomplished people who know their business inside and out. Your job is to add value, not just by spotting risks, but by helping the business move forward with clarity and conviction.

To do that, you have to believe that your voice matters just as much as anyone else’s.

Not because you have all the answers. But because you have a point of view worth hearing.

Every day, I work alongside people who’ve operated at the highest levels of business and government. People who are, by any definition, intimidating.

And I am able to share my opinions, give my advice, and be effective at my job because I know that however impressive these people may be, my views matter too. And they respect what I have to say.

You have to believe in your capacity to reach the milestones you want and to create the kind of impact you’re capable of. Because if you don’t believe it, those goals will always feel just out of reach.

Next time you feel small across the table from someone who seems larger than life, remember:

They were once exactly where you are. They didn't get here by magic. And they are still, underneath it all, just a person doing their best.  Just like you.

You don’t need to be perfect. Or the most ‘impressive’ person in the room. And you definitely don’t need to be fearless. Just brave enough to feel the fear and speak up anyway.

That’s how you do your job well.

That’s how they got there — and it’s how you will too.