Tuesday Email: The People Pleasing Mentality

Read time: ~ 2.30 minutes

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

Most of us think people-pleasing is a virtue. It's not. It's a form of self-harm dressed up as kindness.

Warren Buffett once said, "The difference between successful people and really successful people is that really successful people say no to almost everything." I've always found this fascinating—not because it's counterintuitive, but because it's so hard to implement.

Saying yes feels good in the moment. Saying no feels like a missed opportunity. But this equation reverses with time: today's yes becomes tomorrow's regret, while today's no creates tomorrow's freedom.

When you commit to one thing, you automatically say no to another. This is the inescapable math of having only 24 hours in a day.

The modern world runs faster every day. Demands accelerate. Notifications multiply. "Urgent" becomes the default setting for everything. Yet our capacity remains stubbornly finite.

What's curious is that we understand this in financial terms but ignore it in our personal accounting. We'd never agree to pay someone $100 when we only have $50 in our account. Yet we routinely commit future time we don't actually have.

When the bill comes due, we pay with our well-being, our relationships, and our sense of control.

I see myself as a recovering people-pleaser. I say "recovering" because, like many addictions, the tendency never entirely disappears—you just get better at managing it.

Four years into building our technology business, I still believed I needed to be both founder and CEO. That's what tech companies did, right? I studied the playbooks of successful entrepreneurs, learning about making hard decisions and occasionally prioritizing business over people.

But something wasn't working. Our company had troubling turnover. Projects stalled. I felt constantly drained.

Then came my five-second moment.

I was interviewing another CEO for my podcast. The studio lights hummed overhead, casting harsh shadows as he described his near-exit from his startup. "I was drowning," he said, "doing what I thought a CEO should do instead of what I was actually good at."

My pen froze mid-note. The room seemed to tilt slightly.

"What changed?" I managed to ask, my voice steadier than my hands.

"I hired a real COO," he said. "Someone who could have those difficult conversations I was avoiding. Someone who could handle the operational fallout while I focused on vision—where I belonged."

In that moment, I wasn't a podcast host. I was a mirror reflecting my own unacknowledged truth: I was doing a job I thought others expected of me, not the job I was built for.

The next day, I drafted a job description for a COO.

Three months later, we hired one.

The company's trajectory changed within weeks—not because I left—but because I finally occupied the right role. The person I hired handled the difficult conversations I'd been avoiding. I stopped dreading Monday mornings and rediscovered why I started the company.

What I learned wasn't just about business structure—it was about the unbearable weight of pleasing others at the expense of acknowledging who you are.

Our relationship with approval has deeper roots than we realize.

Many people-pleasers had childhoods marked by inconsistent feedback. When parental love or attention feels conditional or unpredictable, children develop sophisticated systems to monitor and maximize approval. They become emotional meteorologists, constantly checking which way the wind is blowing.

This creates a particular kind of anxiety—not knowing where you stand at any given moment. It's similar to how volatile markets make even seasoned investors uneasy. We crave certainty, even if it's negative certainty.

Herein lies the crucial distinction: kindness and people-pleasing both involve doing things for others, but they run on different currencies.

Kindness operates on a gift economy—you give without expectation of return. People-pleasing runs on a barter system—you give to get, even if what you hope to get is just approval.

Being kind is leaving an anonymous note of encouragement. People-pleasing is signing your name and checking back to see if they liked it.

When we consistently override our needs to meet others' expectations, we create a deficit that compounds over time.

People-pleasers are yes-machines. They commit regardless of their capacity or desire. They do it for others, not for themselves. Deep down, they expect reciprocity or recognition. When it doesn't materialize, resentment follows.

This pattern is exhausting because you're essentially running two operating systems simultaneously: what you do versus what you feel. The gap between them drains your energy faster than any task could.

It's like trying to fill someone else's car with gas while your own tank reads empty, then feeling resentful when they don't offer you a ride.

Here's what I've learned about breaking the pattern:

1. Leverage the pause. In our hyperconnected world, instant response feels mandatory. But that first impulse almost always aligns with pleasing others, not serving yourself. When asked to commit to something, I now say, "Let me check my schedule and get back to you." This creates space to feel my genuine response.

Responding immediately to requests is like grocery shopping while hungry—you'll end up with items you don't need and regret later.

2. Require a "hell yes." If it's not an enthusiastic yes today, it won't magically become one later. A reluctant "yes" is like packing winter clothes for a summer vacation—it takes up valuable space but serves no purpose except weighing you down.

3. Practice disappointing people. This sounds terrible, but it's essential medicine. Start with small nos where the stakes are low. You'll discover most people respect boundaries more than you expect. The few who respond with anger or manipulation are showing you exactly why boundaries with them are necessary.

The effort we invest in prioritization techniques and time management systems often misses the underlying problem: our inability to trust ourselves more than we trust others' expectations.

The greatest productivity hack isn't a new app or morning routine—it's aligning your commitments with your desires and capacity.

When you begin saying no to things that drain you, you create space for work that energizes you. When you stop trying to be everything to everyone, you can become something meaningful to yourself.

Paradoxically, by prioritizing your own needs, you become more genuinely available to others—not out of obligation but out of authentic desire.

That's when the balance we're all searching for finally comes into focus.

Not because we've learned to juggle more demands, but because we've learned to drop the ones that were never ours to carry.

The best is ahead!

-Matt