How to Stop Reacting and Start Winning with Difficult People | Ryan Leak

Ryan Leak shares an unconventional perspective on success, generosity, and faith, demonstrating how radical giving, wise boundaries, and daily surrender to God shape his approach to business and life.

Success Should Be Measured by how Much Is Given, Not Earned, Fostering a Unique Business Growth Approach

Ryan and his wife intentionally measure the success of their business by the amount they are able to give, not what they earn. They set annual giving goals, strategically increasing the distributions from their Donor Advised Fund (DAF) every year. Their approach is fueled by a vision of abundance: they aim to give away as much as possible, with the giving goal rising dramatically each year.

Ryan credits his perspective to generous mentors. His first boss and wife gave away her entire salary one year to missions. Another mentor lives on just 49% of his income regardless of whether a good year means millions or only several hundred thousand dollars, while yet another mentor lives on just 9% and used to give away 63% before achieving bestseller status—demonstrating extreme giving wasn’t a result of new wealth, but a discipline built when it was hard. For Ryan and his wife, the percentage varies, but they never stop pushing to give more.

Generosity Linked To Increased Income Opportunities

Ryan notes a repeated, remarkable pattern: after giving big, he often receives unexpected contracts—even four or five in a day—that are disconnected from any direct association with his acts of generosity. He and his family joke about the phenomenon in group chats, as they consistently observe new opportunities emerging shortly after significant giving. While he doesn’t subscribe to a prosperity gospel mindset or suggest giving as a get-rich strategy, their experience confirms for them a link between open-handedness and open doors. Ryan believes candidly that his own business and income would not be what they are today if he and his family hadn’t prioritized generosity so radically.

Generosity Should Be Pure and Without Attachments

Ryan distinguishes between true generosity and conditional giving. True generosity, he emphasizes, is pure—gifts without expectation or control. He’s experienced both sides: on the receiving end of gifts with strings attached, and as a giver striving for detachment. When someone brings up past generosity or expects something in return, Ryan believes, that is no longer a gift but a loan.

He references the eight levels of generosity, derived from Jewish tradition, each corresponding to a different involvement of ego. At the lowest, grudging gifts are given reluctantly, while higher levels include giving enough, giving with grace, or enabling recipients anonymously. One example is rabbis placing coins on their robes for the poor to take, without knowing their benefactor. At the highest level, generosity is empowering others to make a living themselves—teaching someone to fish, not giving a fish. Ryan and his wife often prefer anonymous giving to keep their own egos out of the process, and to ensure that spiritual purity is maintained.

Trusting God In Business: Surrendering Control and Seeking Divine Wisdom For Purpose-Aligned Opportunities

For Ryan, trusting God is the guiding principle in every area—business, marriage, parenting. He surrenders these matters daily, asking God for wisdom, provision, and clarity. Ryan seeks what he calls “peace or pause” in all decisions, a prayerful check before moving forward. Even when offered prestigious speaking opportunities or lucrative gigs, he discerns carefully, aligning choices with a deeper commitment to family and purpose. If he lacks peace—such as flying to Hawaii twice in one month at ...

Ryan Leak advocates for living with intention, setting boundaries, and being true to oneself rather than conforming to the expectations of others.

Setting Relationship Standards Requires Rejecting the Need to Match Others' Energy and Clearly Communicating Acquaintance Status Versus Friendship

Ryan Leak uses the mantra, "don't match the energy, set the standard," explaining that his expectations for others are realistic—not low—and he maintains his own standard regardless of the energy he's given. As he approaches his 40s, Ryan has prioritized honesty about the status of his relationships. He recounts telling people directly, "we're not friends," not out of animosity, but to clarify that the relationship is merely an acquaintance, not a close friendship. There is no ill will; the goal is to avoid pretending there is a deeper connection than what really exists. Ryan emphasizes that this clarity avoids the burden of maintaining superficial relationships, like group chats with those he doesn't truly know.

Questions such as "what are my kids' names?" or "tell me something that's going on in my life that you don't see on social media," reveal true relationship depth and challenge the false intimacy that social media often creates. Ryan notes that when people are hurt by hearing they aren’t actually friends, asking these questions highlights the lack of genuine connection. He admits that the directness is mutual: he often doesn’t know intimate details about them either, underscoring the absence of real friendship.

By setting realistic expectations, Ryan prevents disappointment and resentment. He explains that when others don't meet his standards, he isn’t disappointed because his expectations are grounded and not based on unspoken, mismatched assumptions. For example, he didn’t get upset over delays with his book’s publication because he only holds himself accountable for his own actions, which allows him to respond with grace rather than bitterness or frustration.

Proving Yourself Undermines Authenticity and Impressions

Ryan Leak describes a gradual shift towards authenticity that began when he was about 38. He realized that the constant need to impress others—trying to build a brand and prove himself—was exhausting and unnecessary. Around 38 or 39, he decided to stop striving for approval, instead choosing to simply share the value he offers. This shift liberated him; he no longer worries about being everything to everyone or tailoring himself to every potential speaking client. Now, Ryan projects calm and confidence, recognizing that he makes a better impression when he’s authentically himself instead of anxiously striving.

Lewis Howes relates to Ryan’s journey, recalling his own exhaustion from trying to please everyone and expressing the newfound peace that comes with accepting that he only needs approval from his core friends and family. Ryan agrees that true potential cannot be reached while people-pleasing, urging others to do the hard (or sometimes easy) work of being themselves. This authenticity attracts respect and honest connections, eliminating the need for the emotional labor of constant adaptation.

Ryan further explains that ...

Ryan Leak emphasizes that leadership effectiveness hinges on proactive decision-making and anticipating challenges, especially when dealing with difficult people. Acting reactively, he argues, rarely leads to desired outcomes, while preparation and empathy support both composure and genuine connection.

Reacting To Difficult People Worsens Outcomes; Proactive Preparation Maintains Integrity and Composure

Leak points out that many individuals find themselves constantly surprised by the predictable behavior of difficult people. Despite extensive experience with someone’s patterns—such as disruptive comments in meetings or uncomfortable family gatherings—people still react as if the behavior were unforeseen. Phrases like "Can you believe they said this?" are common refrains, highlighting a cycle of surprise and reactive frustration.

Being proactive, Leak says, means shedding this surprise and preparing for likely scenarios. He suggests that knowing someone’s tendencies allows for anticipation—and even kindness—before conflict arises. For instance, if he expects a colleague to arrive at work disgruntled on Monday, instead of matching their negative energy, he prepares by perhaps offering them coffee or deciding beforehand not to let their attitudes dictate his own. In situations like traveling or working in high-stress environments (e.g., airports), where delays and angry passengers are common, Leak pre-decides to have a good attitude, regardless of the chaos around him.

This kind of preparation fundamentally changes the energy with which he enters a room, replacing nervous system-triggered reactions with deliberate, integrity-based responses. By planning how to approach challenging meetings, gatherings, or even unexpected run-ins, he maintains composure and authenticity, rather than letting external disruptions determine his actions.

Difficult People's Hidden Pain Shifts Your Response to Compassion

Leak also urges leaders to view difficult people through a compassionate lens. He believes that every difficult person carries unseen pain, stress, or backstory that often explains their behavior and typically isn’t personal. When confronted with hostile or hurtful remarks, instead of reacting, Leak consciously tries to consider what invisible struggles might underlie these words. He reflects on how, if people knew the behind-the-scenes challenges others face, their responses would naturally shift from irritation to empathy.

Rather than simply managing the symptoms of difficult interactions, Leak advocates for addressing root causes through genuine conversation. When something feels off with a person, he suggests dialing things down with an honest check-in, seek ...

Ryan Leak argues that every person has a unique life purpose, a specific "God assignment" that brings meaning to their existence. He insists that until individuals start living out this assignment, life will remain confusing and unfulfilling, no matter their external measures of success. This divine calling doesn't have to be grand, like singing a song, writing a book, directing a movie, or raising a family—it could manifest in the simple, everyday tasks. Leak says, "There is a reason you are on this planet," and finding that reason is key to a purposeful life.

Leak encourages listeners to confront limiting beliefs, particularly the refrain of "I can't." He notes, "They have more I can'ts than I cans," and these beliefs can shape the trajectory of people's lives, convincing them they cannot reach their true potential. Leak shares that even he struggles with the lie that his only value is as a speaker on a stage or a face on social media, and he must daily remind himself that his worth goes beyond visible achievements.

He challenges listeners to ask, "What would you do if you knew you couldn't fail?" For Leak, this question led him to try new ventures and to consider possibilities outside perceived limitations. He warns that having a backup plan can kill dreams, comparing it to a character in "The Dark Knight Rises" who must make a leap without a rope—a lack of safety net compels full commitment and greater effort. Leak asserts that true progress requires such unreserved dedication.

Finding one's God assignment, according to Leak, requires distinguishing between merely good opportunities and those that are divinely aligned. This discernment is a spiritual process, as everyone around you may have a plan for your life, but only through spiritual listening can you discover your true calling. Divine assignments come in varied forms, from public achievements to personal growth and service, but each has its unique purpose.

Racial Narratives and Cultural Beliefs Can Constrain Ambition and Possibilities if Unexamined

Leak discusses how racial narratives shaped his self-image growing up as a Black person in America. He recalls absorbing many limiting messages about what being Black meant, both from broader culture and personal experience. He notes, for example, that he doesn’t sign his emails as "Ryan Leak, the black guy," highlighting how easy it is to internalize false limitations.

As the first Black executive speaker for a Fortune 100 company's retreat, Leak faced significant pressure. A Black executive from the company's board told him, "Don't be the last," underscoring the responsibility that comes with breaking barriers. Leak recognizes that his success opens doors for others, refusing to let others' limited vantage points confine his own potential.

Leak also refutes the belief that if something has never been done before, it cannot be done. He urges people to challenge the status quo ...

True Wealth Is Contentment: When "Enough" Replaces "More."

Lewis Howes and Ryan Leak begin by addressing a common theme: when people are asked what would make them happy, most answer with “more”—more followers, more money, more houses. This endless pursuit puts people on a treadmill of wanting and insufficiency. Leak notes that even those who seem to have it all frequently lack a sense of “enough.” He emphasizes that when someone’s number is “enough,” they move differently and experience a richness that many with more tangible assets never attain. Finding “enough” anywhere in life, Leak says, is the sign of genuine wealth.

Leak insists that the feeling of enough brings true peace, not complacency. It isn’t about quitting or ceasing to strive, but about operating from a place of sufficiency rather than scarcity. Howes agrees, linking inner peace to true abundance, and Leak reaffirms that contentment is what marks real richness. With enough, Leak says, “peace enters the chat.” This shift from scarcity-driven anxiety to abundance-driven peace sets the stage for a more fulfilled life, even as one continues to work or strive.

Living Uniquely Requires Extraordinary Generosity, a Principle Extending Into Generational Values and Family Culture

Ryan Leak shares that he and his wife focus on creating generational giving, not just generational wealth. They structure their finances so that their children will inherit charitable funds, ensuring that giving remains central to their family legacy. He describes the Donor Advised Fund (DAF) mechanism: their kids will inherit money meant to be given away rather than merely spent or saved for personal use. Leak is indifferent about whether his sons will buy luxury goods or choose a particular lifestyle, but he is determined they will be givers.

To instill generosity, Leak and his wife use practical exercises with their children. Over dinner, Leak asked his sons what they would do if given $100,000. His first son chose to give $20,000 to God, save another $20,000, and spend the remainder on Pokémon cards. His second son opted to give $40,000 to God. Leak highlights that while money is part of the exercise, the true purpose is to nurture a spirit of giving.

This atmosphere of generosity, Leak notes, is felt by others. A genuine giver creates an energy distinct from that of a taker—people feel safer, more comfortable, and trust more deepl ...