The Art of the Humblebrag

Let’s talk about something most of us wrestle with whether we admit it or not—when is it okay to talk about our wins? When do you share the awards, the bonuses, the crushing months? And more importantly—when should you shut up about them?

We’ve all seen it done wrong. The guy with the "Another $100K month, just being of service" post that somehow manages to look both insecure and obnoxious. The woman posting her latest leaderboard screenshot in a mom’s group that couldn’t care less. And yet, we’ve also seen people do it right—subtle, strategic, and magnetic. They share wins that create conversations, build curiosity, and pull leads without coming across as tone-deaf or thirsty.

So let’s break it down: when it’s okay to flex a little, when it’s not, and how to share your accomplishments in a way that makes people want to work with you, not mute you.

1. Bragging Is for Buyers, Not Bystanders

Here’s a rule I live by: brag around buyers, not bystanders. If the people seeing your post, hearing your story, or watching your video could become clients, sharing your success makes sense. It shows proof. It builds credibility. It establishes that you’re not just in the business—you’re crushing the business.

But if the only people seeing it are your old high school friends, your Aunt Carol, and 400 other insurance agents who are not in your downline? Congratulations, you just earned a virtual eye-roll.

Here’s what to do instead: if you’re going to talk about numbers or awards, aim the message at people it can actually influence—referral partners, potential clients, or prospects watching from the sidelines.

2. Don’t Just Say You Win—Say Why That Win Matters to the Client

Let’s say you hit the top 5 in your company. Great—do your clients care? Not unless you make them care.

Instead of:

“Just hit the Top Producer list again for the 4th year running!”

Try:

“Hitting Top Producer status means more than just a plaque—it means I’m navigating tough markets and still getting families properly protected and saving businesses thousands. That’s my job, and I take it seriously.”

Subtle shift. Same accomplishment. But now it’s about the people you serve, not your own ego.

3. There’s a Time and a Place for Everything (Even Leaderboards)

Listen, I love a good leaderboard as much as the next competitive psycho. But posting it in a general consumer-facing Facebook group? Bad move. Posting it inside a private coaching group you’re part of where everyone is tracking metrics together? Totally appropriate.

Don’t confuse your personal wins with public content unless it adds value.

Here are a few good places to share wins:

In a professional referral group (like BNI or Chamber of Commerce)

In your own agency page or private client Facebook group

On your LinkedIn, especially when framed as a business milestone

In your email signature or bio (“Over $50M in coverage placed” hits harder than “SuperStar Trophy Winner Q3”)

Places to avoid:

Mom groups. (They don’t care. And it’s weird.)

Your personal page with no context. (Feels like attention-seeking.)

Other agents' posts. (Don’t hijack their win.)

4. Tacky vs. Tactical

Let’s be blunt: there’s a thin line between confidence and cringe.

Tacky:

“Just sold a $10M policy. Stay broke, haters.”

“Another 40 apps this week. Y’all lazy.”

“People keep asking how I keep winning. Sorry, that’s proprietary.”

Tactical:

“Helped a local business save $14K this year by restructuring their policies. These are the conversations I live for.”

“I’ve written more policies in the last 60 days than I did in my first year. What changed? I stopped pitching and started listening.”

“One of my clients sent me 3 referrals this week. Grateful for this community and the trust you place in me.”

The difference? One is all about you. The other is about what you do for others. Even if the numbers are the same, the tone makes all the difference.

5. When Sharing Your Wins Attracts Sales

There are times where sharing your success can directly drive sales. Here’s how:

Scarcity/Volume Proof:

“I’ve already helped 15 families this month and only have room for 5 more this quarter. If you’ve been meaning to get coverage in place, let’s talk.”

Client-Centric Brag:

“Just helped a couple get $750K of life insurance each for less than the cost of Netflix. If that sounds crazy, it’s because most people overestimate the cost of coverage.”

Subtle Social Proof:

“Another shout-out from a client who thought she couldn’t qualify. (She did!) If you’ve ever been told no before, get a second opinion.”

These work because they showcase results and invite others to imagine themselves experiencing similar wins.

6. Be Proud. Be Strategic. Be Self-Aware.

Look, you work hard. You bust your tail for your clients. You solve problems, build relationships, close deals, and lose sleep during underwriting hold-ups. You deserve to celebrate that.

But like anything in sales—it’s not about you. It’s about how you position yourself as the guide, not the hero. Clients want a trusted professional, not a braggadocious insurance bro doing TikToks with money guns.

So share the wins—but tie them to service. Show the scoreboard—but let it highlight what your clients are getting, not just what you’re earning. And when in doubt, ask yourself:

“Will this make my ideal client trust me more… or just think I need attention?”

If it’s the former, post away. If it’s the latter, draft it, read it, then delete it.

Final Thought:

Celebrate your wins, but never forget that the right people are watching. Give them a reason to lean in, ask a question, or send a message. That’s not bragging—that’s marketing with class.

And in this game, class converts at levels boisterous never could.