I work with a teenager who dreams of becoming a pilot. It’s his why for getting out of bed in the morning.
But he also has other options: he could be a lawyer like his grandfather or maybe a firefighter.
In the midst of challenges, he holds on to these visions. The future is limitless.
Talking to him connects me with my own teenage self: the girl who didn’t know what she didn’t know (and the bliss that came with not knowing), the girl who believed wholeheartedly that if you worked hard enough, there was nothing you couldn’t do, the girl who believed in the magic of the universe.
I have a collection of journals commemorating this time in my life kept in my parents’ basement, and I told myself I was going to read them when I turned 26 (10 years from the beginning of the first journal). By then, I surely would have gotten over any second-hand embarrassment from my teenage naiveté. But I haven’t been able to do it yet.
I’m beginning to realize I can’t put it off any longer. Those journals are a window to a more unfiltered version of me, the version of me that believed she was an exception to any discouraging statistic, the version of me that allowed herself to dream. Even if she was cringy, she was passionate, and I love her for that.
While I haven’t been able to bring myself to read the journals yet, I did recently come across something I wrote in high school about the Occupy Wall Street protests. I went to Zuccotti Park for an English class assignment and after willing myself to talk to a protestor wrote the following:
“Though I’m not a real reporter and this ‘interview’ wasn’t going to be published anywhere, I felt really good afterwards. The whole ordeal was virtually painless and yet it did make me feel liberated to go out there and survey what exactly is going on. On my way back to the train, I spotted a sign in the park that said, ‘Become your dream,’ and however trite this may sound, I felt inspired. I definitely never want to be a person that takes the backseat in life.”
(Little did 16-year-old Gwen know that she would go on to have many interviews with many strangers that would be published! But I digress).

I was always a dreamer, as the excerpt shows. I always believed things would get better personally and globally, and I still believe these things. But as we get older, we start making plans based on the realm of possibility. We start postponing the things we want to do to some elusive “someday.” We talk ourselves out of our dreams.
“There’s so many writers out there, who cares what I have to say?”, “I’d love to switch careers, but I already put in too much time into this one,” “I would try rollerblading, but I need to prioritize things that are more ‘useful’,” and so on and so forth.
Sometimes this realism is necessary, i.e. sticking with a job because of health insurance, even if it’s not fulfilling, or acknowledging that we probably can’t make it as a professional athlete in our golden years. But sometimes, we just simply don’t give ourselves the permission to dream anymore — whether that be because of real obstacles or because we’ve been disappointed so many times, we don’t want to risk getting hurt again.
It’s natural for dreams to evolve, but what’s not okay is giving up on dreaming altogether.
I recently watched a movie on Netflix called “The Life List” about this very topic. There’s a girl named Alex (Sofia Carson) who has settled into a life of malaise and aimlessness. She’s dating someone who she doesn’t connect with on any real level, she’s working a job she’s not really passionate about, she’s going through the motions.
When her mom (Connie Britton) dies, one of the conditions for Alex getting her inheritance is checking off all the items on “The Life List” she wrote when she was 13 years old. The list includes learning how to drive, getting a tattoo, learning how to play the piano, becoming an amazing teacher, and finding true love. Alex doesn’t really care about the inheritance, but every time she crosses an item off the list, she gets a DVD of her mom sharing a message.
In one of the DVDs her mom tells her the reason behind the project, “You have to get yourself out of this hole that you're in. I'm not going to be around to dig you out, but I can sure as hell leave you a shovel.”
As Alex tries to complete the list before the New Year’s deadline, she realizes the ways in which she’s been settling and she discovers a drive for life again.
Don’t roll your eyes.
Obviously it’s a movie, but it can also be true for you too.
If you feel like you’ve been stuck in a hole, if you feel aimless, if you feel like you’re settling and not truly living, give yourself permission to dream again. And I mean, really, truly dream. Dream as if there weren’t limits, because very often there aren’t. Very often these limits are in our mind.
It’s natural for dreams to evolve, but what’s not okay is giving up on dreaming altogether.
I was recently speaking to someone who asked me what I would want to do if I could do anything and even though I had an idea of what I wanted, I felt reluctant to say it out loud. I was talking myself out of my dreams because they seemed logistically improbable, and I don’t want to do that anymore.
So how do we get back to dreaming after a long time of not allowing ourselves to do so?
You’re not as far removed from the younger version of yourself as you think you are. There’s still that kid inside of you that has the capability of dreaming. Honor them and honor this present day version of yourself by acknowledging you are worthy of your wildest dreams and that those dreams are only “wild” until they happen.
How to make your own “life list”
Here’s my challenge for you: write your own UNFILTERED life list including everything from the most outlandish bucket list items to reasonable aspirations. (And by the way, the dreams don’t just have to be relegated to your professional or working life. In fact, they shouldn’t. They can be about anything from the places you want to see to the hobbies you want to try).
If you’re looking for some inspiration for your life list, reflect on the following questions:
What is something you’ve always wanted to do but kept postponing?
If failure wasn’t an option, what would you try?
What places have you always dreamed of visiting?
What is a skill or hobby you’ve wanted to learn but never made time for?
What’s something that would make your younger self proud?
If money and time weren’t factors, how would you spend your days?
What’s an experience you’ve always envied in others and wished for yourself
What’s something that scares you but excites you at the same time?
What kind of impact do you want to leave on the world?
Somewhere within the creation and execution of this list you will find yourself. You will remember your hunger for living. You will remember that not everything is written in stone, that the possibilities and the magic of this world are not only accessible to you, they are yours for the taking.
And like the teen I work with – the future pilot-lawyer-firefighter – you will know that there’s an abundance of possibility for you and your life if you only dare to dream.