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The Real Reason You're Not Getting Ahead
The SIGNAL framework to brag right
Howie Chan
August 24, 2025
Dear Legend,
I want to drop a truth bomb right at the start:
the world is NOT a meritocracy.
If it was, the brightest and smartest people would be ahead. And you would be further along. Companies would line up to hire you, refer you, and cheer for you, just based on the quality of your work.
But you and I know, down inside that this is simply NOT how it works.
Time and time again, you see people less accomplished, less smart, less experienced gain success.
The people getting ahead and getting attention aren’t always the best.
They’re the ones who know how to show up.
And if that sentence makes you cringe a little inside? If a part of you whispers “yeah, but I don’t want to be that person…”
Then this letter is especially for you 🫵🏽
Recently I sat down with Lisa Bragg. She is a former award-winning journalist turned executive advisor, keynote speaker, and author of Bragging Rights. She’s helped leaders at companies like Microsoft, Deloitte, and PwC step into the spotlight without losing their soul and she’s on a mission to make self-promotion feel like leadership, not ego.
❤️ Heartset: If you don’t brag, you have nothing to brag about.
“If you don't talk about your work, people assume you haven't done anything worth talking about.”
This quote hits doesn’t it? Maybe you’ll flinch at first, but it’s the truth. If no one hears about your successes, they’ll assume you have no success. Let that sink in…
So, Let’s talk about bragging.
But not the chest-thumping, humblebrag, LinkedIn-thirst-trap kind.
This is about intentional, strategic self-expression so that the right people know what you’re capable of and how you can help them.
I’m going to teach you the SIGNAL Framework. I put it together by stringing together Lisa’s teachings from our deep conversation.
🧠 Mindset Shift: Bragging is not ego. Bragging is leadership.
You’re not showing off.
You’re sending out signals that show people how you can help them.
You’re not hogging the mic.
You’re showing people how to find you.
And if you're not doing that?
You're getting passed over by people with half your skill and double your visibility.
Time to flip the script. (And if you don’t like the word bragging? Fine, call it whatever you want, but you need to talk about your wins.)
🧰 Skillset: The S.I.G.N.A.L. framework
This is your 6-step system to brag without feeling like a douche (or a diva). At the end of this, I’ll share how to apply it for corporate leaders and business owners.
S – Start with the Audience
“Who do you want to talk to to make the future you want to have?”
Identify your primary audience (not everyone).
If you're speaking to future clients, talk in terms of results.
If you're speaking to execs, talk in terms of impact.
The rest? Don’t worry about them. They’re not your target, they don’t help you get to your future self.
I – Identify Your Wins
“So many of us don’t brag to ourselves. We wait for external validation…If somebody doesn’t give you kudos, write it yourself.”
Start your “brag book” or “smile file”
Drop in testimonials, kind DMs, revenue wins, “OMG” client moments, or any memory that reminds you: I’m damn good at what I do.
Before you share it with others, you have to believe it yourself. Do it on Notion, Apple notes, anywhere, just have a log of all the kudos in one place.
G – Get Visible in Their Sun
“We want to get in their sun… Just that they can see you.”
Visibility precedes opportunity.
Engage before you ask. This is exactly what Brian Ahearn talks about in our episode.
If you’re reaching out to podcast guests, investors, or execs, don’t cold pitch. Show up where they are. Comment. DM with value. Mention their work. Jab before you punch, warm them up before you ask.
Lisa even told a story about a guy who bought a billboard just to get one billionaire’s attention. Extreme? Yes. But damn, it worked.
N – Name the Value (with Braggitude)
“Braggitude is bragging plus gratitude.”
Don’t just say what you did, say what it meant. And who helped make it happen.
Instead of:
🚫 “I won this award.”
Try:
✅ “I’m proud to have received this award, and grateful to the mentors, friends, and team who helped me get here. This work helped us X, Y, and Z.”
This is Braggitude: pride with service. It draws people in instead of pushing them away.
A – Amplify After the Moment
“You win something, you do something… and then you don’t tell anyone…Amplification should be your part-time job.”
Schedule it. Repost it. Reframe it and Post it again.
Don’t assume people saw it the first time.
They didn’t. They’re busy being the CEOs of their own lives. (Know that people are not thinking about you, they are thinking about themselves)
You don’t need more content. You need more repetition.
L – Link It to Impact
“Bragging means talking about your success with pride. And pride means justified self-love.”
Bragging is not about “me, me, me.”
It’s about: “This is what I’ve done. Here’s how it helps you. Let me show you what’s possible.”
When you link your work to results, meaning, or transformation, people pay attention. And you stand out not as a show-off, but as a guide.
Now that you know the general framework, here’s how to apply it.
SIGNAL for Corporate Leaders
S – Start with the Audience
Who are you influencing? Senior stakeholders? Future mentors? Team members?
Start by understanding what they care about: revenue, retention, innovation, culture?
I – Identify Your Wins
What have you led, fixed, solved, improved?
Write these down in a “brag book” so you have stories ready for performance reviews or hallway conversations.
G – Get Visible in Their Sun
Speak up in meetings. Share ideas proactively.
Present in all-hands meetings. Write a post in the company Slack, intranet, or send an email to all stakeholders after a major team win. (Don’t forget about LinkedIn.)
N – Name the Value (with Braggitude)
“Proud to have led the Q3 turnaround initiative and so thankful to my team for making it possible. We increased retention by 23% in 6 weeks.”
(Not just results, recognize others.)
A – Amplify After the Moment
Don’t assume everyone saw the email. Bring it up in 1:1s, retros, or mentoring moments.
Repackage learnings into a short internal newsletter or slide for future onboarding. (Don’t forget to do it with Braggitude)
L – Link It to Impact
“This work helped us improve our customer NPS and reduced churn. That means more stability for the whole org.”
Frame wins in terms of business or cultural impact.
SIGNAL for Business Owners
S – Start with Audience
Who do you want to impress or attract: clients, investors, podcast hosts, media?
Get clear on the people who make decisions (and what problems they’re trying to solve).
I – Identify Your Wins
“Helped a client increase sales by 47%”
“Launched our new offer and hit $10k MRR”
“Got featured on a top industry podcast”
Store these in your brag book. You’ll need them often.
G – Get Visible in Their Sun
Show up on the platforms they are on (not just where you feel safe).
Start conversations on LinkedIn. Comment on their posts. Mention them in yours. Join the podcast they listen to. Make sure they see you!
N – Name the Value (with Braggitude)
“We just helped a SaaS founder cut their CAC by 41%. A massive shoutout to the team and our amazing client for being open to a bold strategy.”
Brag + Gratitude = Braggitude.
No ego. Just results and love.
A – Amplify After the Moment
Schedule wins to be shared 3–4 times across weeks.
Turn case studies into Reels, posts, carousels, email stories.
L – Link It to Impact
“This system helps our clients scale with less burnout and more joy.”
Don’t just drop numbers, show how it changes lives.
REAL TALK
So why don’t we all do this already? It’s because we care about what other people think. We don’t want to seem self-centered, “braggy”.
This is the Spotlight effect at play (I wrote about it in this issue, in the last section.)
You think the whole world’s watching your every move.
They’re not. They are busy watching themselves.
So what’s really holding you back?
Fear of being misunderstood? Judged?
Cool. That’s totally normal.
But let me offer you this instead:
Speak to the people who need you.
Let them judge.
Show up anyway.
That’s what legends do.
Want more?
Lisa drops so many gems in our episode: strategic self-promotion, the practice of Braggitude (bragging + gratitude), and the powerful idea of getting “in their sun” to attract high-value opportunities. We also unpack the history of bragging, the danger of humblebrags, and how to stop waiting for your work to speak for itself. (I also dropped 10 of the best quotes on LinkedIn.)
🎧 Listen to the full episode with Lisa on Apple, Spotify, the web, or wherever you get your podcasts.
Make your mark, live your legend 🤘🏽
See you next Sunday!
Howie Chan
Creator of Legend Letters
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