How to Stop Delaying Happiness While Pursuing Big Goals with Jess Ekstrom

Jess Ekstrom and Heather Monahan discuss how the concept of success evolves over time and why it's more fulfilling to define your own "success fingerprint" rather than chasing generic milestones. Their conversation offers insight and practical tools for reframing and auditing your definition of what it means to succeed.

Success Evolves From Personal Values and Circumstances

Jess Redefines Success: From Fame to Flexibility and Family Time

A decade ago, Jess Ekstrom viewed success as fame—dreaming that people would recognize her on the street or that she’d have a Netflix special, a vision she described in her previous book. Now, those aspirations have shifted. Jess couldn’t think of anything worse than being constantly trailed by a camera crew. Her present-day success centers on flexibility: finishing work by three o’clock to play with her kids, enjoying time at her lake house, and sometimes working at half capacity in the summer.

Success Fingerprint: A Personal Framework to Identify Genuine Achievement

Jess introduces the concept of a “success fingerprint,” emphasizing that everyone’s version of success is different. Rather than following a one-size-fits-all approach, she encourages people to explore their authentic desires and circumstances. Through her book “making it without losing it” and an accompanying “success fingerprint GPT” tool (available via pre-order at jessekstrom.com/making it), Jess provides prompts and questions to help readers define their unique framework for achievement before even delving into the book’s chapters. Jess underscores the importance of realizing early on that "no one knows what they're doing," and that success is individually redefined throughout life’s seasons. She advises regular audits of what you are chasing and why, reminding us that comparison to others’ paths is unhelpful since everyone has a different fingerprint.

"Using the 'Purpose Test' to Reveal Intrinsic Satisfaction vs. External Validation"

Jess recommends the “purpose test” as a method to audit your goals and ambitions. She instructs listeners to imagine accomplishing their aims but remaining entirely anonymous—achieving the result without anyone knowing it was them. If the answer is yes, that goal is likely part of one’s true “success fingerprint,” driven by internal fulfillment. If anonymity makes the goal unappealing, it may signal that external validation is the real motivator—prompting an audit of either the goal itself or one’s approach.

Singular Focus Delays Gratification and Happiness

Post-Achievement Letdown Is the Emotional Crash After Reaching Milestones Due to High Energy Investment In a Specific Result

Jess shares her experience with the bittersweet emotions following the sale of her company, Headbands of Hope, during the pandemic. Recording her audiobook, she unexpectedly became emotional about this moment, realizing how profound the act of handing over the keys was. This illustrates a common phenomenon: the “post-achievement letdown,” a concept validated by research on Olympic athletes like Michael Phelps and Simone Biles. After pouring intense energy into one pursuit—be it the Olympics, a wedding, or a major business deal—people often experience a sharp emotional drop when it’s over, as the anticipated moment passes and daily life resumes unchanged.

Athletes and High Achievers Often Face Depression Post-Achievement Due to Loss of Organizing Framework

The sudden emptiness many feel after reaching a major life milestone is not limited to athletes. Jess and Heather both acknowledge feeling a similar letdown after major speaking engagements, moving from the exhilaration of public accolades to the quiet of everyday life. This gap highlights the danger of channeling all energy into impressing strangers while returning home “on E,” depleted for the people who matter most.

Reframe Success As a Continuous Mission to Maintain Motivation and Avoid Collapse After Achieving Targets

Jess notes that tying happiness to external finish lines leads to an endless cycle of disappointment, observing there are no thresholds that banish problems or transform daily life. Instead, she advocates focusing on whether you enjoy the work, the people, and the lifestyle you’re building. She cites research on company performance: organizations with singular, outcome-driven missio ...

Requesting help or opportunities effectively requires more than just stating what you want. Heather Monahan and Jess Ekstrom emphasize that leading with value, understanding others' priorities, and respecting social capital fundamentally shift the dynamic and increase the likelihood of a favorable response.

Effective Requests Need an Investment In Understanding Others' Situations and Priorities

Most people approach requests from their own perspective, prioritizing their convenience rather than considering how their ask impacts the other person. Monahan points out that “90% of people do not do their homework. 90% of people are just coming in thinking about it through the lens of themselves.” This self-centered approach often leads to disappointment, as Monahan experienced when someone she hadn’t spoken to in months requested an introduction to a coveted contact without any recognition of her position or offering reciprocal value.

Researching the projects, challenges, and goals of the person you’re asking goes a long way, especially in a fast-paced environment. Ekstrom shares that before making an ask, she would investigate what someone was working on—such as an upcoming book or foundation work. By referencing these projects in her outreach and offering ways she could contribute in return, Ekstrom demonstrated respect for the other person's situation and effort, which people notice and appreciate.

When Ekstrom wanted an introduction to a podcast, she explained her fit for the show, showing that she had carefully considered why her request would benefit the host. Monahan reinforces this, advising, “Before you ask someone for something, do the homework.” Demonstrating that you understand and respect the other person’s context sets you apart and increases your chances of getting help.

Transforming Asks Into Offers Changes Dynamics

Framing your requests as offers fundamentally changes the dynamic. Instead of simply asking, “Can I speak at your event?” Ekstrom suggests saying, “I see that you are hosting a women’s leadership summit, and I offer professional development services for women. Would that be helpful for your event?” This approach focuses on the benefits to the recipient rather than on your own need.

Offers, rather than asks, show you as a peer. Asking, “Would it be helpful for you?” shifts the power dynamic and frames the conversation as a partnership. Monahan notes that demonstrating how you add value causes others to see you as valuable. When you see and present yourself as worthy, and clearly state the value you bring, people are more likely to respond favorably and view you as a peer, not a supplicant.

Motivation to help increases when people perceive benefits or alignment with their own goals. By addressing how your contribution is useful to the recipient or their audience, you foster stronger connections and improve your odds of a positive response.

Simplifying By Offering Ready-Made Options Boosts Response Rates and Eases Helping You

A powerful way to respect people’s time and increase your response rate is by providing ready-made options. Monahan shares that whenever she asks for testimonials or endorsements, she prewrites three different options for the recipient. This allows busy people to simply pick one and respond immediately, reducing their task from a potential 30 ...

Jess Ekstrom and Heather Monahan explore the struggle high achievers face between chasing future ambitions and finding fulfillment in the present. Their conversations reveal how growth-minded individuals frequently postpone joy, grapple with uncertainty, and encounter anxiety, but also how reframing experiences and breaking routines can lead to presence and personal insight.

Future Ambitions Create Present Psychological Deficit

High achievers like Ekstrom and Monahan often experience a sense of incompleteness, mentally existing in a future shaped by their goals rather than in their present reality. Ekstrom observes, “there's always going to be another dream…another goal,” and warns that if someone waits until achieving a future milestone to start enjoying life or feeling successful, they risk entering a cycle of perpetual dissatisfaction. Both host and guest agree that while it isn't necessary to abandon dreams, it’s crucial to appreciate the process and moments of striving themselves, making “friends with the process of getting there.”

Monahan recalls that enjoying the journey felt unrealistic early on, especially during the difficult "come up" phase in her entrepreneurial path. True enjoyment of the journey only resonated after she reached “the top” in her corporate career and acquired external measures of success—title, wealth, expertise. She notes the challenge in finding joy amid ongoing reinvention, especially during disruptive times like the COVID-induced shift in the marketplace, emphasizing the need to value the ongoing journey rather than always waiting for the next achievement.

They both recognize that reaching a long-sought goal can bring temporary satisfaction, but often new targets quickly emerge, restarting the cycle. The key, they suggest, lies in embracing current challenges and the learning that comes with them, thereby transforming the journey—and even its difficulties—into a meaningful and valuable experience.

Uncertainty Fuels Anxiety; Knowing When Something Will Happen Eases the Present

Monahan discusses the anxiety created by the uncertainty in not knowing when desired outcomes—like finding a relationship—will occur. She admits that if she could simply know the timeline, it would be easier to enjoy singlehood, but “the not knowing is what kills me.” This sentiment extends beyond relationship status to any ambiguous life goal: uncertainty itself, more than the state of lacking, drives distress.

Ekstrom amplifies this idea, recalling a month when her husband, while unemployed, had another job lined up. The certainty of when the next step would arrive turned the period into a time she could enjoy, illustrating how peace often comes from knowing the endpoint.

To counteract the tendency to become preoccupied with the future, Monahan deliberately practices returning to the present moment, especially when her mind spirals into “what if” scenarios. She centers herself by focusing on gratitude for “what I’m grateful for right now” and reminds herself of her personal growth patterns—that each stage and challenge historically led to improvements and better-fitting opportunities. This process doesn't erase anxiety but reframes the unknown into a chance for hope and positive expectation, requiring persistent effort but showing the value in present-moment peace and gratitude.

Protecting Your Energy: Focus On What Matters, Release the Need For Approval

As someone often in the spotlight, Ekstrom notes how she previously attached her sense of value to audience responses. The shift to caring less about others’ approval—without abandoning the purpose or people involved—helped her become a better and more energetically sustainable speaker. “My life will go on if someone doesn’t laugh at my joke,” she realizes, noting that relinquishing the anxiety of external validation enables her to perform and connect more authentically.

Both Ekstrom and Monahan highlight the risk of depletion among energetic speakers and performers who continually strive for intima ...

Meaningful Work Is Created by Linking Tasks To Larger Human Outcomes, Not Assigned by a Job Title

Jess Ekstrom emphasizes that any work can become meaningful when it is connected to the benefit of another person, even if you never meet them. Meaning is not tied to a job title, but to how one links their responsibilities to those who benefit. She observes that at her local Y, employees whose jobs include cleaning equipment also find meaning by counting members' reps and encouraging people on the treadmill, actively contributing to the members’ health journeys. In contrast, in other gyms, some employees focus only on when they can clock out, highlighting the difference between drudgery and fulfillment. Ekstrom asserts that this difference isn’t about the role itself but about how one relates their work to its impact on others.

Purposeful Work: Effort Needed to Link Tasks and Meaningful Outcomes

Ekstrom cautions against the simplistic idea of “do what you love” as the sole path to meaningful work. Instead, she believes meaningful work is created by personal effort to connect tasks to meaningful outcomes for others. This effort transforms ordinary responsibilities into purposeful service. She shares that articulating how your work impacts others—seeing the real value in what you do—boosts engagement and intrinsic joy. For Heather Monahan, purpose can call to you unexpectedly, as when a sign reminded her of her time serving on the City Year board, demonstrating how rediscovering the purpose behind your work brings a tangible sense of fulfillment.

Genuine Care and Investment in Service Creates Joy and Magnetism ...

Meditation and Visualization For Observing Patterns and Identifying Misalignments

Jess recounts a guided meditation at the end of her silent retreat where participants are invited to visualize waking up in their own beds and to play out their daily routines from the perspective of a bird looking down. During this exercise, Jess imagines herself moving through everyday actions, like brushing her teeth and making coffee.

While visualizing her daily activities from a detached viewpoint, Jess notices patterns she had not seen before—such as frequently being distracted by her phone or thinking about work during moments that could be spent with her family. For example, she realizes during her children’s bath time, she often scrolls on her phone instead of being present.

This observational distance makes the gap between her values and actions impossible to ignore. Jess recognizes a clear disconnect: she deeply values being present with her family, but her behaviors—such as being on her phone during important family moments—do not align with this priority. Confronted with these hidden habits, she identifies specific misalignments and feels compelled to adjust her phone boundaries, catalyzing meaningful change in her day-to-day life.

Assessing Your Trajectory and Choices Allows For Timely Course Correction

The process of observing herself leads Jess to closely evaluate whether she likes the general direction her choices are taking her. She describes asking herself if she enjoys the "dots" she is putting on the canvas of her life, and realizes that she does not—especially regarding her ability to be present with family.

This visualization exercise exposes how, without conscious reflection, years can slip by while living out of default and momentum, rather than intention. Spotting contradictions between actions and core values—such as valuing famil ...