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When JPMorgan Chase CEO Jamie Dimon releases his annual letter to shareholders, the business world takes notice. This year, the banking titan’s 58-page missive spanned everything from a stark warning about the economic repercussions of President Donald Trump’s newly announced tariffs to a set of guiding principles for modern leadership. His central message to executives: embrace discomfort, stay curious, and, above all, get out of the office and into the real world.

His core message to executives: embrace discomfort, stay curious, and get out of the office.

“Leadership should always be about learning and questioning,” Dimon wrote, recounting a recent master class he led for 400 JPMorgan executives. “Our company needs to nurture innovation, ambition, and discipline while discouraging complacency, arrogance, and bureaucracy.”

In an environment where market disruption is constant, Dimon urged leaders to expand their perspective and build a more comprehensive view of their business. That means actively seeking diverse perspectives, confronting uncomfortable truths, and regularly reassessing internal assumptions. “Get out of your own echo chamber,” he advised.

For Dimon, that process begins with discipline: closely tracking industry trends, studying competitors, engaging with people who possess more advanced technical or managerial expertise, and holding oneself and others to account. 

“We can learn so much from our competitors, customers, and employees if we only open our eyes and ears,” he explained. 

He shared his own experience. A decade ago, Dimon assembled a senior leadership delegation to travel to China and observe companies like Alibaba, Ping An, and Tencent. Though initially met with hesitation, the trip proved transformational, ultimately broadening the team’s understanding of digital banking, biometrics, and emerging technologies like super apps—insights that helped shape JPMorgan’s digital evolution.

But learning from competitors, Dimon argued, is just the beginning. The real imperative is anticipating their next move and responding proactively. “You’ve got to say, ‘What are the competitors going to do next?’ because that shows when you’re getting to the puck and where the puck is going to be – not where things currently stand,” he explained.

Dimon also emphasized the importance of looking outside one’s industry for inspiration. Citing Chick-fil-A’s use of drones to optimize drive-thru operations, Dimon pointed to the fast-food chain as an example of sector-specific problem-solving that offers universal lessons. While not directly applicable to banking, it reflects a mindset he values: pragmatic, creative thinking in the face of evolving customer needs.

Equally vital, Dimon emphasized, is the ability to examine one’s own decisions with honesty and humility. He stressed that effective leadership requires a willingness to acknowledge mistakes and reflect meaningfully on how to do better—a level of self-awareness he considers essential to credibility and long-term impact.

He pointed to the 2012 London Whale trading scandal, which resulted in billions in losses and securities fraud charges against two JPMorgan traders, as a pivotal moment that demanded both accountability and deep introspection. In retrospect, Dimon admitted the incident lacked adequate oversight, including by the bank’s risk committees, and served as a stark reminder of what he called the “disease” of hoarding information within large organizations.

“I also recognize that I don’t always get everything right and that I have made plenty of mistakes myself,” he acknowledged.

JPMorgan Chase declined to comment.

This story was originally featured on Fortune.com

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Michael Saylor’s Strategy said it will register an unrealized $5.9 billion loss in the first quarter after adopting an accounting change that requires valuing the digital asset at market prices. 

Shares of the dot-com-era software maker turned leveraged Bitcoin proxy formerly known as MicroStrategy fell as much as 14% on Monday. Earlier, Bitcoin wiped out almost all of its gains since Donald Trump’s U.S. presidential election win in early November.

Strategy and fellow corporate buyers of Bitcoin are being made to recognize the unrealized changes that often produce big swings in earnings or, in the case of Strategy last quarter, losses. Strategy waited until the first quarter to adopt the accounting change that was approved last year. 

Prior to the accounting change, the Tysons Corner, Virginia-based company has been classifying its Bitcoin holdings as intangible assets—similar to brand recognition or trademarks. That designation forced Strategy to permanently mark down the value of its holdings when the price of Bitcoin dropped. Gains could only be recognized when tokens are sold, which Saylor has vowed not to do, even saying his digital wallet keys should be burned when he dies.   

Part of the first-quarter loss will actually result from Saylor’s recent spending binge, which has produced roughly $1 billion of paper losses on the $7.79 billion the company spent on Bitcoin in 2025, according to Bloomberg calculations. The company owned $41.8 billion of Bitcoin coming into the year, an amount that fell by nearly $5 billion in the first quarter with the 12% drop in the price of the tokens. That equates to about $6 billion of “mark-to-market” losses, according to Bloomberg calculations as of March 31, before taxes.

At the same time, the company’s retained earnings will whipsaw into positive territory, courtesy of a nearly $13 billion boost from the new accounting, according to Bloomberg calculations. 

Strategy became the first public company to buy Bitcoin as a capital allocation strategy in 2020, with co-founder and chairman Saylor saying the enterprise software firm needed to embrace the policy to survive. It grabbed the attention of Wall Street as the shares took off with speculators using it as a proxy for the digital currency. 

Saylor took advantage of the surging demand to sell more shares to purchase additional Bitcoin, eventually expanding to convertible debt and preferred shares offerings to fuel the buying spree. The stock is up more than 2,200% since the start of August 2020. 

Hedge funds have been driving some of the demand for the convertible debt, as they seek out Strategy for trades that incorporate buying the bonds and selling the shares short, essentially betting on the underlying stock’s volatility.

With the price of Bitcoin faltering along with other risky asset this year, the meteoric appreciation in the value of Strategy’s shares has also slowed. And last week, Strategy’s shares got their only sell rating after boutique equity research firm Monness, Crespi, Hardt & Co. cut its view on the firm, saying the market for the securities used to fund the Bitcoin purchases is increasingly saturated.

This story was originally featured on Fortune.com

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