The Life You Wanted vs. The Life You’re Living
“I did dream of my wedding growing up and that’s not to say that I didn’t dream of the bigness of my life. But I could have spent more time dreaming of my life. And as much as grief does surface for me around not having children and not having a partner, I still wouldn’t want the wrong partner… at all”
Recently, I was listening to an episode of IMO with Michelle Obama and Craig Robinson. Tracee Ellis Ross was the guest, and she said something that caught my attention:
“I did dream of my wedding growing up and that’s not to say that I didn't dream of the bigness of my life. But I could have spent more time dreaming of my life. And as much as grief does surface for me around not having children and not having a partner, I still wouldn't want the wrong partner… at all”.
There’s a kind of grief people don’t talk about enough: the grief of a life that didn’t happen. A dream deferred or that may not even happen. A version of success that no longer fits where you are now.
I know that grief.
Though Tracee was talking about dating, I’m talking about identity and the life I thought I’d have. But grief is grief — whether it’s over a relationship, a job, a timeline, or the dream you imagined.
After my father passed, I took time off work. It was my first time being unemployed. I had my first part-time job at 16 and I never had an employment gap until that point. With my father no longer walking this Earth, my life looked different. And in that space, a different kind of clarity came through.
In addition to grieving him, I was also grieving the life I thought I would have built: the straight path of good grades, grad school, professional growth, certifications, and climbing a corporate ladder I didn’t even want anymore.
I realized that no job title, salary, or role made me valuable. At the time, it felt unsettling to even think about living a life different from what I was conditioned to want. What was all that hustle in my 20s even for?
What I now understand is that transitions sometimes carry invisible grief — and not just around death or loss.
I’ve grieved the life I thought I’d have when I moved from my hometown, Chicago, to New York City.
I’ve grieved not moving to Los Angeles (yet), even though it’s been something I’ve truly wanted since college.
I’ve grieved what 2020 was supposed to be – it was supposed to be “my year”. A comeback after a very challenging 2019.
We don’t get time back. And I don’t feel the need to “make up for lost time.” But I had to accept it.
Sometimes we think that if we grieve something, that means we’re ungrateful for what we do have. But that’s not true. You can honor what’s gone or what never was — and still be thankful for where you are.
Today, I grieve the loss of a steady, predictable income. And I’m still grateful to be building something on my own terms. Something impactful.
The termination I experienced wasn’t a “blessing in disguise.” It was wrongful. Unfair. I didn’t deserve it.
Yes, I chose to turn it into purpose. But to be clear: I didn’t need to suffer in order to find purpose. The grief doesn’t give the work meaning. I do.
And what we can learn from Tracee is this: it’s okay to still want what you want. Even if it hasn’t come within the timeline you wanted.
But it’s also okay to be so rooted in who you are that you know you’ll be good either way. That the thing you want is a bonus. Not having it doesn’t make you any less worthy. And once you get it – if you get it – it won’t make you more worthy.
Being a business owner can be lonely. People don’t always get the vision. They’ll project their fears and doubts onto you. And it’s easy to internalize that if you’re not grounded in self-trust.
But self-trust isn’t about having all the answers. It’s about knowing your own limits. That you’ll recognize when it’s time to recalculate. That you’ll allow yourself to grieve, and then — in your own time — release it.
“You are modeling… how to build the life you want. Not the life that somebody told you [that] you were supposed to have”
Sometimes the hardest grief to sit with is the loss of what could’ve been. It takes courage to admit that the reality you’re living isn’t what you always wanted. What you dreamed.
And it takes even more courage to stay open anyway. To still hope. To still move forward.
If we let it, that grief can teach us. It can soften us. It can open us up to joy. It can open us up to new or different possibilities.
Transitions aren’t just about what’s next. They’re also about making peace with what never was. That’s where your next chapter begins.
Every shift isn’t loud. Sometimes it starts with quiet questions. My free guide — 5 Major Questions to Ask Before Making a Shift — is designed to help you pause, reflect, and move forward with intention. Download it here.