When Work Looks Good on Paper but Feels Draining: How Values Realign Energy and Fulfillment
Many people assume that work is supposed to feel hard. Dreading Monday is joked about so often that it’s practically cultural shorthand. But according to experieced executive coach Leigha May, former HR executive at companies including SpaceX and Nike, normalizing that dread comes at a cost. “If we normalize it,” Leigha explains, “we find ourselves in areas like burnout pretty quickly.” In her work with clients, she often sees resentment, numbness, or quiet exhaustion show up long before people realize something is misaligned internally.
Instead of perceiving these feelings as flaws, it may serve us better to see them for what they are, which is signals.
The Early Signs of Misalignment Are Easy to Miss
Leigha works with people whose lives often look successful from the outside. The right job. The right title. The right company name. Yet something feels off.
One of the earliest signs is resentment. Another is dread where there used to be motivation. Sometimes it shows up as going through the motions, checking the boxes, and telling everyone that things are “fine” without actually feeling fulfilled.
Because success is so narrowly defined for us, many people assume the discomfort means something is wrong with them. Leigha challenges that assumption. More often, it’s a sign that someone is living by expectations they inherited rather than values they chose.
The Quiet Role of “Should” in Burnout
Much of this misalignment starts early. We’re taught to work hard, achieve, and climb. We internalize a set of rules about what success looks like and then follow them faithfully. The trouble begins when effort and achievement are no longer connected to enjoyment or meaning.
Leigha encourages people to listen closely to their internal language. Phrases like I need to, I must, or I should are often clues. When choices are driven by obligation rather than alignment, resentment tends to follow. Even gratitude can become a silencing force when it’s used to override dissatisfaction.
“What I’m really curious about,” Leigha says, “is what you tell your best friend when you’re having coffee.” That private truth usually sounds very different from the polished version shared at a dinner party.
Redefining Success on Your Own Terms
A recurring theme in Leigha’s work is helping people separate their own definition of success from the one they absorbed along the way. When people reach milestones that were supposed to feel fulfilling and don’t, they often turn that disappointment inward. Leigha invites a different question. Was that goal ever truly yours?
There’s no faster path to dissatisfaction than chasing someone else’s version of success. Real fulfillment begins when people pause long enough to ask what actually matters to them, outside of salary, status, or external validation.
Values as a Practical Decision Filter
For Leigha, values aren’t abstract concepts or inspirational words pulled from a list. They’re practical tools for decision-making.
She encourages clients to clearly define the values they want their lives to be built around, both professionally and personally. When values are named and understood, decisions become simpler. Instead of weighing endless pros and cons or worrying about others’ opinions, the question becomes straightforward: Is this aligned with my values or not?
Sometimes that clarity leads to small adjustments. Sometimes it prompts larger changes. Either way, values provide a steady filter that prevents people from drifting into resentment over time.
A Simple Practice to Restore Energy and Focus
One of Leigha’s favorite daily practices is deceptively simple: celebrating wins. A win, she explains, isn’t just having a good day or a successful meeting. It’s identifying what you’re genuinely proud of yourself for. Something you did that was within your control. Something that reflects how you want to show up.
This practice matters because most people carry a strong negative bias. The mind naturally scans for mistakes and gaps. Pausing to ask What am I proud of myself for today? gently retrains attention. Over time, that shift does more than boost morale. It reinforces values. When people notice that the moments they’re proud of align with what matters to them, they’re more likely to repeat those behaviors. Energy follows attention.
Many clients keep a running list of wins in their phone or journal. Looking back over weeks or months often reveals growth that felt invisible in real time. Small moments compound.
Following the Nudges That Matter
When asked what advice she would give her younger self, Leigha doesn’t point to a specific career move or accomplishment. Instead, she emphasizes paying attention to curiosity.
Those small nudges. The interests that quietly pull at you. The people or ideas that spark something. Leigha sees those as expressions of internal wisdom, not distractions.
Following them doesn’t require radical change overnight. It starts with noticing and giving yourself permission to explore what feels meaningful before it becomes urgent.
Fulfillment Is Often Closer Than It Seems
The conversation comes full circle with a simple but powerful reminder. The gap between where you are and where you feel fulfilled is often smaller than it looks. Burnout and resentment don’t always require a total life overhaul. Sometimes they’re invitations to make a few intentional adjustments guided by values rather than expectations. Taking the time to name what matters is not indulgent. It’s foundational. And for many people, it’s the first step back toward energy, clarity, and a version of success that actually feels like their own.
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🎧 Time Billionaires, "Tips to Spot Early Burnout and Reverse It to Get More Done” with Leigha May
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