Welcome to Startup Diaries by Jenny Na—a newsletter about what no one tells you about working at startups: the ups and downs and everything in between.
In my first post of 2024, I wanted to share something a bit more personal. I hope you can use it as a reference to clarify your intentions for your career & life this year.
Until you make the unconscious conscious, it will rule your life and you will call it fate. — C.G. Young
to upend all plans, I had just finished a grueling 12-hour shift at the hospital when seemingly out of nowhere, I was struck with irrefutable clarity that this wasn’t my path.
I could either cash in four years of investment and progress to the next level (in this case, med school) or hit restart and play an entirely different game.
I decided to start over.
During this period of peak existential angst, I remember wondering:
Why didn’t I realize this sooner?
I mean, a heads-up would’ve been nice. But in reality, any nudges from my intuition would’ve been ignored by me anyway. I was too busy going through the motions, completely disconnected from my gut instinct.
Even though I hadn’t listened before the day I chose to start over, the whisperings of my heart grew into an unsettling bellow as a final warning call that day.
So in my attempts to be a better listener, I discovered journaling.
Journaling is the cathartic process of weaving together narratives to construct your reality. When paired with deliberate reflection, you create a healthier version of that reality that’s better aligned with your values.
Now once a year, I read a year’s worth of journal entries and write an essay about them. I analyze the inner dwellings of my mind and surface with insights that rivaled the revelations gained from therapy.
This yearly retroactive has single-handedly been responsible for some of the biggest growth spurts in my adulthood — and I can confidently say that I’ll do it for the rest of my life.
As you define your career and personal goals for 2024, rather than anchoring hope onto a manifested version of yourself, I suggest an alternative: look back and within.
My process
Imagine being an archeologist but instead of surfacing the ruins of an ancient world, you uncover the ruins of your mind.
You dig up backlogged dreams, sieve through streams of consciousness, and chip away at negative self-talk.
Eventually, you uncover a handful of truths like opening presents on Christmas morning. Some presents are a delight, others are more practical reminders. But the most valuable presents tend to be painful, hard-to-swallow truths because they become powerful agents of change.
I don’t think there’s a “best” way to do this but here’s my approach:
Step 1: Curate an experience that energizes you
When you think about the words peace and rejuvenation, what imagery comes up for you?
Maybe it’s the bold brilliance of sunsets or the rhythmic calm of the ocean.
For me, it’s the stillness of the forest. I spend a few days alone in a remote cabin. I unplug and fill my time with things I enjoy, with the ultimate goal of doing this yearly retroactive exercise.
Over the years, I found myself looking forward to this experience as if it were a gift to myself — a pat on the back for another year well lived.
My only firm recommendation is that you go alone so you’re free from obligation and distraction and that you go somewhere new to shake you out of your normal rhythm.
Here’s a list of my favorite cabins if that’s your thing!
Step 2: Catalog a year’s worth of journal entries
This step is simple but can take a while, so I recommend breaking it up into a few sessions.
Start reading by month and jot down interesting tidbits along the way — memorable quotes, highs and lows, emotions felt, and so on. You’ll need to shift through piles of debris to find those few nuggets of gold.
Tangentially, I find it helpful to keep a list of patterns you notice whether that’s the subject matter, the tone of your writing, or the emotions and perspectives experienced.
Often, we hold various voices in our heads that represent different sides of ourselves. Notice who often takes center stage.
This can be a fascinating process to shed light on blind spots and behavior patterns that previously went undetected.
Step 3: Capture key takeaways and observations
Step away and let everything you just read marinate in your brain.
Get out of your head — I like getting lost in a thriller novel, trying a new recipe while playing a movie, or taking a dip in the hot tub with a cup of black coffee.
After a few hours or the next day, open a blank screen or paper and just start writing. Chances are, you already noticed a few big themes so allow them to the surface.
Write without judgment. You are ultimately your audience.
As an example, here are my yearly takeaways from 2023:
I have everything I need.
Power isn’t something to be earned or bestowed upon. It’s my birthright.
Courage disarms fear.
There’s something about crafting these narratives that gives me such fulfillment. The great benefit of writing is that it clears your mind. Despite how murky and messy any given year was for me, topping off the year with this reflection exercise helps me face the new year with utmost clarity and stillness.
Afterward, I like to share my essay with a few close friends and send hand-written letters to the people who made the biggest impact on me that year.
Here’s a Notion template you can use to format your yearly reviews.
How this exercise benefited my life
I think the best way to show you the impact is to share real examples of what I wrote in years past.
Example 1: How painful truths become catalysts for change
I learned that the weight of shame is incredibly heavy. Over time, the faces of people I ghosted became the bookends of my days as I spent my nights dreaming of painful confrontations.
This is an example of one of those painful, hard-to-swallow truths.
Experiencing shame on a day-to-day was hard, but tolerable. I would journal about it, push through the day, and repeat. But digesting a year’s worth of shame was both shocking and overwhelming; It became the activation energy I didn’t know I needed to eradicate shame from my internal dialogue.
In the following year, I experienced a flourishing of connection. Eradicating the shame narrative created space for me to accept the love and support that was available to me all along — I just failed to recognize or acknowledge it.
Example 2: How identifying patterns can reveal blind spots
A dominant voice in my journal entries was one like a scared and helpless child who didn’t have the agency to solve or alleviate a situation, even though she knew exactly what to do and had the means to do it.
I remember this being a shocking discovery, especially for someone who highly regards her independence and competency. Helpless? Who, me?
In disbelief, I dug deeper into this subconscious helplessness and discovered the root cause: my upbringing as a parentified child. I learned that this is quite common for first-generation immigrants such as myself, who experience growing up too quickly before being developmentally “ready” for it.
By identifying this pattern of helplessness, I was able to better catch myself in moments of self-sabotage.
Example 3: How memory is a powerful resource
The most important things in life, I have. So what do I have to fear? What do I have to worry about? What do I have to lose? Despite the potential missteps and failures ahead, I am loved by the people who matter.
When I read back on this journal entry, I was facing a mountain of doubt about my recent career decisions. I had just left my job without a backup plan. Grappling with this newfound uncertainty was harder than I thought.
It was during moments like this when I discovered this moving statement that I had written six months prior.
This is the power of memory.
Realizing how much is at your disposal in the underappreciated corners of your psyche. Instead of some podcast or New York Times bestseller, look within.
You probably already know exactly what you need to hear.
Note to readers
Thanks for reading! A takeaway from my retroactive last year was to write more—so you can expect more essays about the startup experience every other week. Do you have your own version of a yearly retroactive? Message me and let me know!
wow, this idea is so simple yet so promising. i'm really excited to try this out.
historically, i have a tendency to never read past journal entries, because i treat them like a time capsule surprise for the future. but that's not very useful! i should re-read them often and become an expert on my past entries and my psyche.