Overcoming personal branding’s biggest challenges: 148 ideas and insights to take control of how people think about you

Building ‘The Brand Called You’ comes with pitfalls. CEOs, consultants, investors, and others share their hard-won advice for keeping your personal brand growing.

[Source images: Adobe Stock]

Ryan DiLazio was a rock star at his job. On paper.

It was 2022, and DiLazio was a manager of social marketing and strategy at a global advertising agency, where he was working with such brands as Sour Patch Kids, Chicken in a Biskit, and Nutter Butter, all subsidiaries of the food giant Mondelēz International. Technically, DiLazio’s role only encompassed ideating social media concepts and scheduling them, but he was regularly taking on more creative work, too—including designing Instagram posts and recording TikToks. 

Soon, DiLazio’s creative work was taking off: His wacky, deep-fried TikTok strategy for Nutter Butter was regularly generating millions of views, while an activation based on the hit show The Summer I Turned Pretty was garnering major praise from higher-ups. “The president of Mondelēz is on an email thread going, ‘This is the best work I have ever seen from our brands in years,’” DiLazio recalls. 

Behind the scenes, though, DiLazio received a different message. “I got put on a PIP,” he says, using the HR acronym for “performance improvement plan,” the first step on the road to potentially being fired.

For DiLazio, who’s built a personal brand around identifying and playing off of the weirdest trends on social media, it was a moment of whiplash. He’d been hired for his personal brand, only for it to be called into question. 

“I can no longer count the number of times I’ve been both hired and punished by agencies for having the ‘fresh perspective’ they’re looking for and my ‘fingers on the pulse of culture,’” he says. “I have been plucked from the internet for my tone of voice, for noticing things others don’t, and for a willingness to try new things. Each factor can so easily become a double-edged sword.”

I interviewed DiLazio for a special report on how people are building their personal brands in 2026, featuring more than 200 insights (you can read that here).

Personal Brand Special Report: 207 insights and ideas to grow your brand and career

When we spoke, DiLazio had moved on to become a partner at his own creative agency, Loudmouth, and managing editor of the digital culture newsletter and creative advocacy agency Silence, Brand! Although his quirks may have been a double-edged sword in a corporate environment, they’re now a key marketing tool for his own businesses. 

Still, DiLazio’s experience epitomizes the often unspoken reality for those developing personal brands: While almost everyone I spoke with believes that building their personal brand has resulted in major career gains, the majority also told me they’ve experienced some meaningful challenges along the way. 

Personal branding can be a divisive topic, and critics often focus only on the negatives. Conversely, evangelists tend to ignore the inevitable setbacks in the process. Our take—grounded in the reality that you have a personal brand and are being judged by it no matter what—offers a frank look at the obstacles and how to overcome them.

In this dispatch from the world of personal branding, you’ll learn: 

The biggest problems people encounter as their personal brand takes shape

What they do to evolve their brands

How to balance a personal brand with a full-time job 

When and where to draw boundaries to protect yourself

Where systems and structures can be transformative, including one leader’s vibe-coded “Personal Brand Command Centre”

Why women and underrepresented groups face greater scrutiny in their brand building—and what they do to take back power

The pigeonhole: When your personal brand becomes a reputational limitation

“I was taught to be creative, to ask questions that make people think, to push forward into uncharted territory, but the reality is all of these things make some uncomfortable. Some are even threatened by any or all of those things in combination. Where I may see a wide-open opportunity, some see a threat to their title, internal agency politics, or a dynamic I will never be involved in.

“I’ve seen this manifest as meetings I wasn’t invited to, chats about me that I hear about later . . . odd questions [asked] of me such as ‘Are you sure you’re a strategist . . . not a creative?’ and more. (I’m BOTH!)” —Ryan DiLazio, partner, Loudmouth; senior managing editor, Silence, Brand!

DiLazio’s hard-earned advice: “Turn your spite and frustration into more creativity. Nobody can tell the ending of a story you haven’t finished writing, especially your creative career. Your employer doesn’t own your creativity the way they’d like to. Give it somewhere to live outside of work: Post a daily photo to a Tumblr. Start a blog. Build a hobby project. Freelance on the side. And if it comes to it, quit the toxic job. Never let someone else’s lack of confidence become the roadblock to your creativity.”

“When you are seen on social media as a personal brand, they don’t necessarily expect you to execute, too. Some treat you like a talking head instead of an operator. They expect you to want to be a brand evangelist instead of doing other work within the brand.” —Christina Garnett, chief customer and communications officer (fractional), Neuemotion

Garnett’s hard-earned advice: “Most of what people see from me online is the thinking. The execution happens in rooms they’ll never see. So I started posting about that side, too: what we built, what broke, what the numbers did. Once people see you shipping, they stop assuming the posts are the job.

“If you have a visible profile, people will fill in your job description for you. I’ve learned to define what I own at the start of any role or engagement, in writing, before anyone else does. When requests to be the face of something come in later, there’s already a document that says what I was brought in to deliver.”

“In the first three years transitioning back from a paid employee to a brand that has its own product out in the marketplace, what I didn’t want to do is be seen as a consultant. I knew that there are only so many consultants who are going to succeed, especially within one segment. Go look at any McKinsey PowerPoint presentation, BCG PowerPoint presentation, or any consultancy presentation: They all look the fuck the same. They use the same bullet points, the same color backgrounds. You have to break those digital lock-ins. You have to break the rules. You can’t stand out if you’re fitting in.” —Evan Shapiro, chaos cartographer, ESHAP 

Shapiro’s hard-earned advice: “As an independent agent in the business world, a superpower combined with passion can be reframed as ‘compelling expertise.’ And that kind of expertise can be valued in the marketplace.  

“Twenty-five years ago, at the urging of a great coach, I set out to find and define my superpower. I studied the things I did well—and the........

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