The Uncomfortable Truth About Comfort: Why Entrepreneurs Must Learn to Get Comfortable Being Uncomfortable
“A ship in harbor is safe, but that is not what ships are built for.” — John A. Shedd
There’s a strange irony in how most people approach entrepreneurship.
They dream of leaving the 9-to-5 so they can finally feel free. They imagine working in cozy cafés, taking vacations when they want, and living on their own terms. That dream, while inspiring, often hides a hard truth: comfort is the enemy of growth.
If you got into entrepreneurship to be “comfortable,” you might be walking straight into a trap.
Let’s talk about that.
The Comfort Conundrum
You don’t become a better athlete by sitting on the couch. You don’t become a better entrepreneur by staying in your comfort zone.
But here’s what happens all too often:
- You get an idea.
- You start small.
- You make a bit of progress.
- Then… you find a groove. You stay in that groove.
- And slowly, without realizing it, your ambition shrinks to the size of your routine.
You’ve stopped building and started maintaining. You’re playing it safe.
And if you’re honest? You’re not uncomfortable—you’re just bored.
Growth Lives on the Edge
Author and psychologist Scott Peck said, “The truth is that our finest moments are most likely to occur when we are feeling deeply uncomfortable, unhappy, or unfulfilled.”
Think about it.
Your first pitch? Scary.
Your first sale? Nerve-wracking.
Your first team hire? Total leap of faith.
Every level of progress in your business likely came at a cost of emotional, mental, or financial discomfort.
Real entrepreneurs don’t chase comfort. They pursue meaning—and meaning often hides in the places we’d rather avoid.
Let Me Show You What Discomfort Looks Like
Case 1: Sandra, the Freelance Designer
Sandra had clients who praised her work but underpaid her. She stayed quiet because she didn’t want to “rock the boat.” One day, after months of frustration, she sent a message:
“I’ve restructured my pricing to better reflect the value I provide. Here’s the updated rate card.”
Heart pounding, palms sweaty, she sent it out to all her clients.
One dropped her.
Two agreed instantly.
One said, “Finally. I was waiting for you to do this.”
She didn’t get comfortable. She got bold.
And her income jumped by 40% that quarter.
Case 2: Tunde, the Boutique Owner in Lagos
Tunde had been running a successful boutique in Lekki but sales were stagnating. His friends kept saying, “You need to take your store online.” But he hated tech. Avoided it like the plague.
One night, frustrated by low foot traffic, he stayed up watching Shopify tutorials. He launched a simple e-commerce site within two weeks.
Sales picked up.
Not because he had it all figured out, but because he chose to get uncomfortable long enough to try.
Now 60% of his revenue comes from online orders.
The Discomfort Formula
So how do you strategically shift into discomfort without burning out or becoming reckless?
Here’s a proven 3-step approach:
1. Identify Your Avoidance Zones
Discomfort often shows up as procrastination, excuses, or delegation overload. Ask yourself:
- What have I been avoiding for over a month?
- What task gives me anxiety just thinking about it?
- What feedback am I scared to hear?
Entrepreneur and investor Naval Ravikant put it plainly:
“If you can’t decide, the answer is no. If you’re waiting for more information, the answer is no. If you’re still afraid, the answer is yes.”
Your growth lives inside that “yes.”
2. Start With Micro-Stretches
You don’t need to jump into a lion’s den. Just start small.
- Afraid of sales calls? Start by leaving one voice message a day.
- Hate rejection? Pitch one stranger on LinkedIn every week.
- Terrified of video? Record a 30-second clip and post it anyway.
Each micro-stretch is like a mental push-up. The more you do, the stronger you get.
3. Ritualize the Uncomfortable
High-performance coach Brendon Burchard once said, “Ambition fails without routine.”
Make discomfort part of your routine.
- Block out an hour each week for “scary stuff.”
- Build a checklist of things you normally avoid and tackle one per day.
- Create an “Uncomfortable Wins” journal—track the times you leaned in and what happened.
Over time, what once felt scary becomes normal. That’s how you evolve.
Quoting the Greats
To ground this message, consider the wisdom of Steve Jobs:
“I’m convinced that about half of what separates successful entrepreneurs from the non-successful ones is pure perseverance.”
Perseverance through what, exactly?
Disappointment. Uncertainty. Criticism. Long nights. Hard choices.
These aren’t obstacles to avoid—they’re the curriculum of entrepreneurship.
Still Not Convinced? Picture the Alternative
Imagine a year from now.
You kept doing what’s comfortable.
You stayed in the same pricing bracket.
You avoided that strategic partnership.
You didn’t start the podcast, launch the product, or attend the conference.
You played it safe.
Now compare that to another version of you—the one who stepped into fear, chose growth over ease, and embraced awkward beginnings.
Which version wins?
Which one actually becomes the entrepreneur you admire?
Action Challenge: Get Uncomfortable This Week
Here’s your assignment:
- Write down 3 uncomfortable tasks you’ve been avoiding in your business.
- Rank them by impact—what moves the needle most?
- Schedule the top one for this week. Put it on your calendar.
- Do it before you’re ready.
Because readiness is a myth. Action creates readiness.
Final Word: Make Discomfort Your Strategy, Not Your Struggle
The best entrepreneurs don’t just survive discomfort. They design it into their lives.
They know that uncomfortable conversations lead to clarity. Uncomfortable decisions lead to innovation. Uncomfortable moments lead to breakthroughs.
So, the next time your stomach tightens before a pitch, or your mind spirals before hitting “publish,” don’t retreat.
Recognize it.
Embrace it.
Because that feeling?
That’s not failure.
That’s growth knocking.
Will you answer?
