3 Things That Make Me Uncomfortable—And Why I Lean Into Them

Comfort zones are great places to rest—but terrible places to lead from.

As a SaaS CEO, I’ve realized that discomfort isn’t just part of the job—it’s where most of the real growth happens. Every major breakthrough in our company came after a period of tension. Hiring before it felt “safe.” Shipping before it felt “perfect.” Saying no to what looked like opportunity but felt off in my gut.

Discomfort is the signal. It tells you where something important is happening—either in your company, your team, or yourself.

In this edition, I’m unpacking three situations that still make me uncomfortable, and why I’ve learned to lean into them—rather than avoid them.

Because growth, clarity, and stronger leadership often live on the other side of discomfort.

1. Being the Least Smart Person in the Room

There was a time when I thought my job was to have the answers. Now, I know my job is to build a team that doesn’t need me to have them.

Hiring people who are better than me in their domain—especially in engineering, finance, or product design—was intimidating at first. I worried I’d be exposed, or lose control. But it’s turned out to be one of the smartest decisions I’ve made.

The people I trust the most now are the ones who challenge my ideas—not those who simply agree.

When I find myself the least technical, least experienced, or least skilled in the room—it’s actually a win. It means I’ve hired well. It means we’re building depth. And it means I can do what I’m actually here to do: set the vision, remove roadblocks, and create a culture of high performance.

Why I lean into it:
If I’m the smartest in the room, I’m in the wrong room—or I’ve built the wrong room. That discomfort is a sign I’m scaling in the right direction.

2. Shipping Before It’s Perfect

This one still stings.

Every time we ship a feature that has rough edges, I feel the pull to delay. Just one more QA run. One more polish. One more internal debate.

But here’s what I’ve learned: no amount of internal iteration beats real-world feedback.

Some of our best improvements came after pushing something imperfect out the door and listening—really listening—to what our users had to say. Not just the bugs, but the “I wish it could do this” or “this part makes no sense.” That feedback became the fuel for fast, focused iteration.

We still aim for excellence, of course. But excellence through iteration beats perfection in isolation.

Why I lean into it:
Perfection is a myth—and waiting for it slows your momentum. Shipping early is uncomfortable, but it’s honest. And the faster you get feedback, the faster your product becomes something people actually want to use.

3. Saying No to Easy Revenue

Revenue is oxygen for any startup. But not all revenue is created equal.

We’ve had opportunities—big ones—that looked amazing on paper. Large logos. Healthy budgets. Strong usage projections. But deep down, we knew they didn’t align with our product roadmap. They’d require custom builds, manual support, or workflow exceptions that didn’t scale.

Saying no felt wrong at first. After all, cash flow is king.

But in hindsight, those "no’s" protected our product, our brand, and our team’s energy. Saying yes to the wrong kind of customer could have pulled us away from our core, slowed down our speed, and blurred our value proposition.

Now, when a potential deal feels like it would force us to bend too far, we pause. And often, we pass.

Why I lean into it:
Saying no is uncomfortable—but strategic clarity often demands it. Long-term sustainability beats short-term wins.4. It sets the tone across the company.

When your team sees that you’re in the inbox—not to micromanage, but to engage—it creates a ripple effect.

They start to lean in more too.
Support becomes more thoughtful.
Product teams start asking better questions.
Everyone is reminded that what we build is only half the story.

How it lands is the other half.

Culture trickles down. Whether we’re intentional about it or not.

What I’ve Learned

Discomfort isn’t a signal to retreat. It’s a signal to reflect.

And more often than not, it’s a signal to advance—thoughtfully.

Here’s how I’ve reframed discomfort in my journey as a SaaS founder:

• Discomfort = Exposure
  It shows me what I don’t know and where I need to grow.

• Discomfort = Speed
  It forces me to move forward, iterate fast, and learn in real time.

• Discomfort = Clarity
  It pushes me to ask hard questions about priorities, customers, and product direction.

If you want to build something real—whether it’s a company, a team, or even just yourself—discomfort is the door you have to walk through.

And on the other side? Growth. Insight. Alignment.

Let’s Talk

I’d love to hear from you:

What’s one thing that makes you uncomfortable as a founder, leader, or operator—and how are you handling it?

Drop a comment below or send a DM. I read every one.

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