A recent piece in Entrepreneur magazine by Sheldon Yellen, CEO of BELFOR, offers five candid lessons he wished someone had shared before he stepped into the corner office: embrace the pressure, focus on the journey, lead by doing, build trust, and — perhaps most powerfully — vulnerability isn't weakness, it's strength (https://www.entrepreneur.com/leadership/5-things-i-wish-someone-had-told-me-before-i-became-a-ceo/493874).
Every one of these resonates. But that fifth tip, as wise as it is, only tells half the story. And the half it leaves out is the one most entrepreneurs know intimately — but almost never talk about.
The Tips Are Right
Yellen's core message is that pressure signals meaning, that leading by doing matters more than titles, and that a culture built on trust creates a ripple effect of engagement and ownership. All true. All hard-won wisdom worth absorbing. But it's the vulnerability lesson that deserves a deeper conversation.
The Smile That Hides Everything
There is an unspoken pressure that comes with entrepreneurship that no one puts in the brochure — the pressure to always appear confident. To walk into every room wearing a smile that says everything is going great, the risks are paying off, I am completely in control.
The reality looks quite different on the inside.
It's lying awake wondering if payroll will clear on Friday. It's a major client who has gone quiet. It's the constant chase for new business while keeping existing clients happy, managing staff, and building a benefits package competitive enough to attract and retain great people — all while being the person in the room who projects calm.
This is the pressure point that almost never gets discussed. Not because entrepreneurs are dishonest — but because the culture of entrepreneurship quietly demands the performance of confidence, even when the performer is exhausted.
Why the Fifth Lesson Matters Most
Yellen writes that the most powerful moments in his career came when he let down the walls, asked for help, and showed up as his full, imperfect self — because vulnerability doesn't make you soft, it makes you human.
The entrepreneurs who thrive long-term are often the ones who find trusted advisors and partners with whom they don't have to perform. People with whom the smile can come down. People who help them build the right plan so that eventually — the smile becomes something real.
That conversation is worth having. And it starts with being willing to have it. Let us know if we can help you get it started.