Lan Nguyen Chaplin: Most Leaders Don’t Celebrate Their Wins—But They Should
Celebrating success is a silent challenge many senior executives face. Real progress—and lasting resilience—requires recognizing what’s going well. Yet, business and leadership literature has long emphasized learning from failure: how to recover, adapt, and grow after setbacks. Less has been written about what it takes to acknowledge and build on success, particularly among senior executives navigating today’s high-pressure and often unforgiving business environment.
In conversations with leaders across industries and in my coaching work, I’ve seen that self-celebration is not only rare—it’s genuinely uncomfortable. Many leaders admit that slowing down to acknowledge their accomplishments feels unnatural, even embarrassing.
This discomfort comes at a cost. When leaders constantly push forward without stopping to mark their progress, they risk more than burnout. They deprive themselves of a buffer against stress (self‑affirmation), a source of ongoing motivation (self‑reward), and the mood lift that fuels creativity and good judgment (the progress principle). Over time, this can compound into lower resilience, waning drive, and poorer decision quality—undercutting the very effectiveness they’re chasing.
Why does this happen? On the surface, the reasons seem straightforward: when you’re at the top, calling attention to your achievements can feel awkward, risky, or self-important. But that reluctance often runs deeper than ego or optics. To better understand the root causes and how to address them, I interviewed 10 executives in various sectors, including education, communications, consulting, public relations, and talent management. I intentionally sought people outside my own academic field—from a former CMO of Deloitte to a construction entrepreneur and a longtime executive turned consultant—to capture a range of experiences that a broad cross-section of leaders could relate to.
Drawing on those discussions, as well as existing research and firsthand experience, I’ve identified three core barriers that prevent leaders from celebrating wins and concrete actions you can use to overcome them.
Barrier 1: The Worthiness Gap
Several executives admitted they don’t feel entitled to celebrate, even when they’ve objectively done well. This self-doubt, combined with the near-constant pressure and crisis-mode pace many leaders operate under today, makes it difficult to pause and acknowledge what’s going right. As Mike Chisholm, the former CEO of multiple mid-sized service companies and now CEO of Chisholm Consulting Group put it, “During bleak times, the focus naturally shifts to solving immediate problems—protecting the business, supporting employees, and keeping operations afloat. That constant state of crisis leaves little room to celebrate progress. You’re just trying to put out too many fires to feel like you can pause to recognize what’s going right.”
Kris Safarova, CEO of StrategyTraining.com, described a similar struggle from a different angle. “I’ve immigrated three times in my life” she said. “It’s hard for me to recognize how far I’ve come because I’m too used to having no capacity for rest and working much harder than what is probably healthy. Pausing to celebrate feels unfamiliar—and not something I can afford to do.”
Action: Make your progress visible to yourself.
When challenges pile up, stakes are high, and self-doubt starts to creeps in, it can feel undeserved or irresponsible to draw attention to your wins. But celebration isn’t about pretending everything’s solved—it’s about staying anchored in what’s working and reinforcing the truth of your impact. That grounding fuels the confidence and resilience you need to navigate what’s ahead.
Frank Koo, a former senior executive at LinkedIn and now Founder and CEO of Nextplay, told me he overcomes imposter feelings by tracking his accomplishments in a personal calendar and marking tasks as complete to acknowledge progress. Seeing a visible record of what he and his team have achieved helps counter the internal narrative that he “hasn’t done enough,” gives him a grounded sense of momentum during difficult stretches, and reinforces a culture of self-reflection and growth for everyone.
You can do the same. Start by listing a few of the biggest challenges or expectations you’re carrying—whether they’re board priorities, growth goals, or team needs. Then, next to each one, jot down a concrete step you took this week to move it forward. Maybe you navigated a tough investor call, hired a critical leader, or helped your team pivot under pressure. Keep the list somewhere visible: in your notes app, on a sticky note, or in your planner.
Schedule five minutes each week to revisit and update your list. It’s a simple but powerful way to train yourself to treat progress as something worth pausing for.
Barrier 2: External Pressure
Many executives described a mindset of constant forward motion—where milestones are viewed as steps on an endless path instead of meaningful “small wins.” This was compounded by the relentless demands of stakeholders, customers, and boards, leaving them little time or space for self-reflection. As a result, the leaders I spoke with often overlooked or dismissed their own achievements.
Rory Rubin, the CEO of S.I. Container Builds, told me that she’s been conditioned to constantly ask, “What needs to be done next? How can I keep improving and growing to keep others content?” In always looking ahead, she rarely has the chance to look back and honor her wins along the way.
Action: Distinguish real vs. self-imposed pressure.
Not all urgency comes from others. If you’re a leader at the top, you’ve likely been relentlessly driven to get where you are. But that same drive can turn inward and become counterproductive. Many high performers set unnecessary deadlines, feel guilty for taking breaks, or assume they need to be “always on.” Clarifying what’s actually being asked of you—and letting go of imagined demands—creates space to recognize progress, reflect, and set more sustainable boundaries around your time, energy, and expectations.
Start by auditing your obligations through two lenses: external expectations and internal standards. Chisholm told me he treats every demand—real or imagined—as part of a bigger project. Doing so forces him to zoom out, weigh priorities, and avoid reacting to every request with equal urgency. Before committing energy, he clarifies expectations with boards, clients, or teams. This step often reveals a surprising truth: many of his “deadlines” are self-imposed. By naming the source of the pressure he feels, Mike not only reduces unnecessary stress but also creates the mental space to pause and recognize what’s working across his team. He can then use those insights to lead more intentionally when new challenges arise.
Rubin experienced a similar shift. Working in a high-pressure industry where demands never stop, she assumed stakeholders expected her to be constantly available and in motion. She admitted that working at such an intense pace left her drained and caused her to miss out on meaningful moments in her personal life. Once Rory recognized how much pressure she was creating for herself, she set firmer boundaries—protecting weekends, respecting her team’s time off, and deprioritizing low-stakes work. Her new rule is: if urgency isn’t explicit, don’t treat it as urgent.
In short, your workload doesn’t have to change, but your mindset does. Reflection should be a part of the job, and not a reward for finishing it.
Barrier 3: Fear of Violating Cultural Norms
Some of the leaders I spoke with described workplace environments where overt celebration from people at the top feels culturally inappropriate, boastful, or politically risky. For leaders who want to model humility and spotlight their teams, acknowledging their own accomplishments can feel like overshadowing others rather than elevating them.
Action: Redefine what celebration looks like.
You don’t need a spotlight to acknowledge success. Small, personal rituals—like journaling, savoring feedback, or sharing a private moment with a mentor—can be just as powerful. As Deborah Roedder John, a senior leader in the education sector, put it: “When you’re very successful, you start competing more with yourself than others. Those wins feel more personal—and deserve to be celebrated in a personal way.”
Jennifer Maloney Adab, the CEO of Triple A Media, a PR and executive communications firm, learned this firsthand. “Celebrations often take the shape of formal announcements and publicity—effective for optics and audience reach,” she said. “But when it comes to my own personal growth, I’ve learned that the most meaningful milestones are best honored quietly.” After selling her first company, she skipped the immediate press release and took a solo walk, giving her space to reflect on the milestone and what it meant.
Jonathan Copulsky, the former CMO of Deloitte and now an adjunct at Northwestern University, takes a more reflective approach. Each year, he writes a short letter to close friends and family summarizing what he accomplished and what he learned. The ritual helps him zoom out from daily highs and lows and see the big picture. When he was an executive at Deloitte, he also made a point of celebrating his colleagues—hosting dinners or organizing shared experiences and outings. For him, celebrating his team was also a way to honor his growth as a leader. Their progress reflected the culture and direction he helped shape.
. . .
Celebrating your own achievements isn’t self-indulgence—it’s a stabilizing force in a business climate defined by uncertainty, scrutiny, and nonstop demands. When leaders are expected to deliver more, faster, with fewer missteps, acknowledging even the smallest wins can help you stay anchored, energized, and clear-minded for what comes next. Don’t let those moments slip by. Noticing them will help you build the confidence you need to keep moving forward.
This article first appeared in the Harvard Business Review.
Lan Nguyen Chaplin is professor of marketing at Northwestern University, Medill School of Journalism, Media, Integrated Marketing Communications. She is also the founder of QuanTâm, a nonprofit that creates opportunities for young professionals to expand their networks and sharpen their professional skills while serving their community.