In my keynotes, I talk about how the things that hold us back individually are the same things that hold us back collectively inside our organizations. It’s not complicated. When we’re not thriving as human beings, we don’t suddenly become our best selves when we swipe a badge or open a laptop. We carry our fear, resentment, exhaustion, and unfulfilled lives right through the front door with us.
People love to say they keep their personal life and professional life separate. That’s a lie we tell ourselves to feel more in control than we actually are. Unless you happen to be severed—where your “innie” and your “outie” are two separate consciousnesses—your life comes with you to work.
And if that sentence made you wonder whether I’ve lost my mind, that’s the premise of the TV Show, Severance: employees are surgically split so they have no awareness of who they are outside of work and no memory of their job once they leave it.
I understand the appeal. The idea of setting down the weight of your life for eight hours a day sounds seductive. But at this point in human history, it’s still science fiction. Believing we can separate our identities from our work isn’t aspirational—it’s a fallacy.
One of the biggest things holding people back in life is the relentless pressure to meet the expectations of others. I don’t mean healthy expectations like showing up for your team, honoring commitments, and doing your job well. I’m talking about the kind of expectations that quietly hijack an entire life. The kind where you reach the end (hopefully after a long one) and realize you spent most of it making choices that kept everyone else comfortable while you slowly disappeared.
“I wish I had lived a life that made me happy.”
“I wish I had been true to myself.”
Those are not rare regrets. They are common.
This is where people accuse me of advocating selfishness. They’re wrong, but I understand why it sounds that way. Much of adult life is obligation. We show up because we have to. We provide because people depend on us. But when you add up years of choices made solely to avoid disappointing others, what you end up with is a life that isn’t actually yours.
And yes, let’s address the obvious rebuttal.
“I hate my job, but I have bills to pay.”
Of course you do. Survival matters. I’m not naïve. But my response is still uncomfortable: there are other jobs. Maybe they don’t come with the same salary, title, or status—but that’s the trade you’re making. Not between work and no work. Between comfort and happiness. Between identity and freedom. And if you never interrogate that trade, you’ll arrive at the end of your one wild and precious life wondering why you cared so much about appearances instead of peace. And then you die.
I was listening to Claire Danes being interviewed by Amy Poehler on her podcast. Early in her career, when she was a struggling actor, she was sitting at the kitchen table with her parents. They wanted what good parents want: stability. A “real” job. Something dependable. Something safe.
And Claire said she’d rather be poor doing what she loves than take a nine-to-five that offered security but no joy.
Yes, she eventually found enormous success. That’s the version of the story people like to tell. But that’s not the part that matters.
Because for every person who “makes it” in a visible way, there are thousands who never do—and they are still deeply content. Struggling actors. Artists. Writers. Musicians. People living paycheck to paycheck who wake up aligned with what fills their soul. They are not miserable. They are not lost. They are not waiting for permission to be happy. They’ve already decided what matters.
This isn’t toxic “follow your dreams” nonsense. It’s not an argument for recklessness or abandoning responsibility. It’s about agency. About examining the choices you’re making only to satisfy expectations you never consciously agreed to. Security without joy still has a cost. Pretending otherwise doesn’t make it free.
The most extreme version of this is living a lie. People denying their sexuality. Their beliefs. Their identity. Living as a performance for the world.
But the more common and more dangerous version is quieter. It’s the slow erosion of agency. The incremental surrender of your own wants to someone else’s needs.
A friend of mine is ready to leave his job. Financially, mentally, emotionally—he’s done. He’s given decades of exemplary service. He’s earned the right to choose his next chapter. But he hasn’t left. Why? Because his boss keeps fighting to keep him.
That’s a compliment. Being needed feels good. Being wanted feels validating.
But my friend is the fixer. The closer. The reliable one. If he leaves, someone else has to step up—or the boss does. I don’t blame the boss for trying to keep him exactly where he is. I would too.
What worries me is that my friend might stay long enough to wake up one day and realize he gave away years of freedom he can never get back. Time does not negotiate.
I know people staying in relationships where they are deeply unhappy—because of kids, finances, family pressure, faith, or fear. I don’t have to convince you this is real. Most of us have stayed somewhere too long because leaving felt harder than enduring. Maybe you’re there right now. Maybe you’ve convinced yourself everything is “fine” because rocking the boat feels dangerous—even though the boat has a slow leak and you are quietly drowning.
It’s always easier to see this clearly in other people’s lives. We’re excellent at diagnosing everyone else. We’re terrible at auditing our own.
So here’s the reckoning.
Not tomorrow. Not when things slow down. Now.
Where are you settling?
Where are you complying instead of choosing?
Where have you confused being responsible with being alive?
Look at your job. Your relationships. Your calendar. Your bank account. Your silence. Every one of them is telling the truth about what you value—even the parts you’d rather explain away.
You don’t need to burn your life down. But you do need to stop pretending that staying put is neutral. It isn’t. Every day you conform to expectations you no longer believe in, you are actively choosing a version of your life.
So choose it consciously—or disrupt it.
Because time will make this decision for you if you don’t.
And when it does, it won’t ask what you were afraid of losing. It will only reveal what you gave away.
