The Grief of Letting Go
And the joy that accompanies realizing that even though it isn't what you wanted, it's exactly what you needed.
There is this trend going around on social media that’s like
Plan A:
Career by 25. Married by 27. Kids by 30.
Plan B:
They are showing what they are actually doing with their life.
The purpose is to express that even though things didn’t work out how they planned, they love their life and are embracing the plan B.
It has sparked many thoughts for me, but there is one in particular that I want to share because I think it needs to be talked about. As happy as we may be for how our lives have unfolded thus far, I think there is a part of us that grieves for what we thought it would be. And I think it is important that we hold space for that grief.
Growing up I was constantly told that if you work hard in school and go to college, you’ll get a good job and be able to build a good life for yourself. My fellow millennials understand that for a lot of us it did not work out this way. And honestly, I’m not mad about it because it allowed us to create alternative paths and build whole careers that previously did not exist, it allowed us to take part in shaping the world in new ways.
But it also meant we would drown in student loan debt, struggle with loneliness in a way we hadn’t before and grapple with how to build a life with no blueprint. And for me this is where grief enters the chat.
"I'm grieving the life I thought I would have, letting go of the expectations I once held for myself, and accepting that although my life is not what I thought it would be, it is beautiful and real.” ~JD Lynn.
The earliest career dream I can remember, I wanted to be a lawyer. To be honest, I’m not sure why exactly but that was my mission up until middle school/high school. It was around that time that I discovered creative arts. I started dabbling in playing instruments, doing theatre and writing. In the back of my mind I started to wonder what it’d be like to have a career doing something creative, but when I tried to talk to someone about it I would get discouraged. The conversations would always end the same, those are not careers they are hobbies. You need to pursue a “real” job.
My first semester in college I took a psychology class and my interest was peaked. I have always been a person who wants to understand why people are the way they are so I was like alright psychology could work. I declared a major and continued down the path. For a whole bunch of reasons the college thing didn’t pan out. A lot of life happened. In 2013 I move to Dallas and in 2015 I started my first corporate job working as an admin assistant. 2015-2020 was the period of my life that brought many blessings and an insane amount of lessons. And from that my first blog was born, my freelance career came to life and eventually my business too.
It was also during this time that I realized the life I envisioned wasn’t going to happen and in order to move forward I had to make peace with that and let it go. My 17 year old self said I wanted to become writer, have partially a window walled apartment in New York City as my home base and travel the world. Somewhere between there and about 21, I lost that version of me to the version of women that the world demands…a wife who eventually becomes a mom that puts her life on pause in the pursuit of helping everyone else reach their goals. I got married at 26 and committed to climbing the corporate ladder in pursuit of the house, 2.5 kids and the dog. I moved up the ladder and at year 4 I realized I hit a ceiling because I was overworked, underpaid and extremely unfulfilled. I had a conversation with my then manager who said, your unwillingness to conform is going to keep you stuck where you are. And in that moment I knew a shift was in order.
I was still determined to get the house, the 2.5 kids and the dog, but I was going to do it by betting on me. I was going to become a full-time entrepreneur. And that’s exactly what I did. A year to the date of that conversation with my manager, I left the corporate world to do my own thing. January 30th, 2020 was my official last day. A few months later covid enters the chat and everything changes yet again. I have no choice but to sit with myself and figure out how to pivot.
The stillness of 2020 gifted me with the clarity to see that 17 year old me indeed had it right. I have always been a writer - a truth teller - a person who shares their experience with the hope that it helps someone else. What I didn’t know then, that I’m keenly aware of now is that this looks different in different seasons. Every experience that I have, every version of my life that I grieve serves a purpose in my own journey and often time someone else’s. My greatest lessons and blessings.
A very good friend of mine said something to me that really focused my perspective and in ways inspired the words you’re reading now.
I believe everything happens for a reason, and I think this level of enlightenment that you have is meant to be a beacon to those stuck in dark places.
Those simple words released something in me that I didn’t even realize was stuck.
Grief.
I’ve been carrying grief for what I thought my business would look like, who I thought I would be, how I thought my life would look, even the size of my bank account.
At one point if you would have told me that my life would be as it currently stands at 34, turning 35, I would have said I have failed. Me currently, as of April 2025, understands deeply that I am right where I’m meant to be.
Even though I don’t have the friend group that’s grown through different phases of life, I have a handful of the best friends I couldn’t begin to even know to ask for. Even though I don’t have the college degree my business has allowed me to do some of the most meaningful and impactful work. It brought me experiences I didn’t know were possible. Even without that degree, I have a 9 to 5 job that would be most people’s dream, and I am quite literally the right hand to the CEO. I may not be a writer as a career (yet), but I’m blessed to get kind messages from folks who resonate with my writing and find freedom, hope and courage in it.
My point is this…if you are currently in a dark place, holding a lot of grief or just don’t know what - trust that your seasons are what you need them to be. And if you’re walking through and need a hand, lean to the people who love you. I know it’s hard and you don’t want to feel like a burden, but for the people who are your people such wording doesn’t even exist. Share the weight. Let them love you.
We hold all that we need, to be all that we are called to be. It just starts with belief and processing the grief.
All my love,
Britt