Leaving the Life You Built on “Shoulds”
Michelle Obama left a prestigious law career not because she failed, but because it never really fit. This is what it looks like to walk away from the life you thought you were supposed to want.
We don’t build an unfulfilling life on purpose. Most of us start with good intentions. We follow the rules, check every box, and do what’s expected. We chase stability, and the “right” kind of success.
And still, we can end up in a life that looks right, but feels all wrong.
Michelle Obama had that moment. What she did about it wasn’t flashy, but it was brave as hell.
Right On Time is our weekly series of lessons in courage, clarity, and change for those rewriting their story — in two minutes or less.
Michelle Obama was a rising star in corporate law in her early 30s. She’d gone to Princeton, then Harvard Law. Landed a job at Sidley Austin, one of the top firms in Chicago.
On paper, she was everything she was supposed to be. Smart. Polished. Successful. Impressive.
And quietly… she was miserable.
She’s talked about it in interviews and in Becoming — how she would sit in her office wondering, Why am I doing this?
She’d built a life full of “shoulds.” And it was working… until it wasn’t.
So she walked away.
Michelle took a job in public service — one with less money and prestige, but more meaning.
She moved closer to herself, one shift at a time, through nonprofits, university work, and community leadership.
None of it looked as impressive as “law firm partner” on LinkedIn. But it gave her something way better: alignment. Integrity. Joy.
Leaving a life built on “shoulds” doesn’t always look dramatic. It doesn’t have to start with a bang, or blowing up your old life.
Sometimes it’s just a quiet refusal to keep playing a game you no longer believe in.
Take a few minutes today and mull this over:
What part of your life still runs on rules you never agreed to, or a dream that never really fit?
Remember, you get to rewrite the rules, even if you’re the only one who understands them. It’s never too late to want something truer to you.
✌🏻 Miranda
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