The Art of the Humblebrag

An unapologetic look at tooting one’s own horn and why I’m compelled do it

Typically, the act of bragging about oneself, especially when done under the guise of humility, is frowned upon in polite society. Such an offense is commonly known as a “humblebrag.” Merriam-Webster defines the humblebrag as “a seemingly modest, self-critical, or casual statement or reference meant to draw attention to one's admirable or impressive qualities or achievements.”

But despite conventional wisdom, even high-powered celebrities engage in faux humility when it suits their aims. For example, when Grantland’s Harris Whittels compiled a power list of the greatest humblebraggers of all time more than a decade ago, Oprah ranked near the top of his list.

I know words. I have the best words.

~Donald Trump

Since I spend most of my time on a North Carolina island with a population that barely registers, there are few people around for me to brag about my accomplishments. As a result, almost no one who knows me is aware that I once had a career on Wall Street. Upon reflection, my piece from last year, which mentioned my role in a Death of a Salesman production, could be construed as a humblebrag. But in my defense, how could I have known the only play I’ve ever been in would be nominated for nine theater awards?

On the serious side, I couldn’t resist patting myself on the back on Notes the other day. At the risk of repeating my prior offenses, I thought I’d expand on my comments. In November, I wrote about how a cadre of poker-playing billionaire donors seemed to surround the Trump campaign. I pointed out Nate Silver’s oddly timed op-ed predicting a Trump win, in which The New York Times conveniently failed to disclose his connection to JD Vance patron Peter Thiel.

More to the point, I pointed out that Jeff Yass, who owns one of the world’s largest investment firms, was behind Trump’s about-face on TikTok. A few days ago, I noticed that a high-profile commentator drew a similar conclusion. I’m not suggesting this individual lifted the idea from my piece, although this happens to nobodies like me all the time. My point is that almost two months went by before anyone connected the dots.

It’s not bragging if you can back it up.

~ Muhammad Ali

A few Fridays ago, I did a live walkthrough of a GOP reconciliation wishlist that dropped as an end-of-the-week news dump. The fifty-page document is the sequel to the 2017 Tax Cuts and Jobs Act (TCJA), which expires at year-end. But Republicans have a problem.

According to estimates, extending the TCJA will cost over $4 trillion over ten years. Even worse, eliminating taxes on tips, overtime, and Social Security benefits, all campaign promises could add $1.8 trillion.

The House Budget Committee circulated the document, which contains a laundry list of potential “pay-fors” Republicans are considering to offset massive tax cuts they want to force down our throats. Everything from taxing college scholarships to removing the mortgage interest deduction is on the table.

Since about half the proposed cuts came from the Ways and Means Committee, it seems logical that Democrats on that committee would mount a strong response. Nope. Days passed with no significant pushback. As one subscriber pointed out, the NYT didn’t cover this story until six days after my livestream. Go figure.

The point of my horn-tooting is this: the people you should hear this kind of analysis from—the media writ large or Democratic politicians—are either asleep at the switch (most Democrats), or bending the knee in hopes that Trump will be nice to them (the list of offenders too long to enumerate). No matter how you slice it, they think the rest of us are powerless.

But here’s the thing: we may not be billionaires, but we are many. We don’t have to lie back and take it. I won’t, and neither should you. That said, we must do more than shout at our televisions or go into a panic every time we get a “breaking news” message on our phones.

That’s how this newsletter came into existence. In the years since, it has grown from an idea tossed around my family’s kitchen table to a publication with thousands of subscribers. But let’s not get it twisted. Unlike some of the top newsletters on this platform, The Journeyman isn’t supported by outside investors or a staff. Substack is unlikely to award me a $25,000 deal like they just did with a popular TikTok influencer. There is no six-figure deal to help me gather steam; Substack has no $20 million accelerator fund to help me grow my business.

This platform’s management seems more concerned with enticing folks to move here than nurturing struggling creators who have been here all along.

But you know what? I don’t care.

While a big financial boost would be a game-changer, I get a certain amount of satisfaction from knowing those who subscribe to The Journeyman do so, not because it’s some shiny object, but because something clicked organically.

Maybe it’s because of my stories of growing up in the Jim Crow era, or my fly-on-the-wall stories of finance. Perhaps it’s my quirky “Moments of Zen” on Notes. It could be that folks don’t run across a Black ex-Wall Street trader-turned-capital markets analyst-turned-social justice warrior every day of the week.

Whatever it is, thank you. I’m glad we found each other.

One more thing

If we’ve learned nothing in the past few days, it is that we’re in for a ride. Understand that this isn’t accidental. The chaos and confusion are a part of an age-old strategy, meant to keep us off balance. They do it because it works. My role, however, is not to chase every breaking news notification, but to step back and analyze the bigger picture. While I don’t have half a dozen flat screens in front of me anymore, my approach is still the same.

Sift through the nonsense. Disregard the distractions. Focus on what is important. Doing this right takes a bit of work. It also requires a certain amount of luck. But I wouldn’t have it any other way. It also requires the support of paid subscribers. If you can, please consider becoming one. Think about becoming a founding member. I’ll do my best to make things worth it.

Whatever you decide, I appreciate you. We’ll get through this.

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