This quote from Steve Jobs to the 2005 Stanford graduates is my all-time favorite. It has always given me the courage to move forward, if only by a little, even in my darkest times.
This post is a slight tangent from my norm, but as this blog is my medium for self-expression, I want to document what is perhaps to date, the most monumental decision in my life. It’s also quite long, so be warned.
You can also listen to the audio recording of this post here:
Three years, two companies, and a promotion later, I’m saying goodbye to the corporate world. I’m finally taking the leap of faith to run my own tutoring business and pursue my passions in life. Some may argue that three years is too short to make such a drastic decision, but this path is not one I chose overnight. My decision was, for lack of a better word, calculated (I hate the negative connotations associated with that word).
To provide some context, I’m going to tell my story in three parts: The Seed, The Turning Point, and The Leap.
I’ve gone through periods where I’ve pursued teaching with full force, and others where I’ve tried to back away completely. Yet like a boomerang, it always found its way back into my life. In retrospect, this push-pull relationship extends as far back as my high school days.
During that time, helping my friends with their math homework was just a hobby. I enjoyed learning something to a point where I could teach it. But tutoring as a career was the furthest thing from my mind. Little did I know that by having all of those library sessions and phone calls, I was sowing the seeds that would grow into my own future business.
Fast forward a few years, I was now a second year in college. The pressure of finding a summer internship had set in. Then, as if on cue, I learned of an opportunity to become a SAT tutor for a California-based test prep company.
That summer was a doozy.
What the company failed to make clear was how the position placed less emphasis on teaching and more on the sales aspect. I was essentially expected to build a branch of the company from the ground up. How was a timid introvert supposed to take on such an overwhelming task, especially one that required extensive human interaction? I knew I could shine in front of a class, but I wasn’t sure about the rest.
Not one to back down from a challenge, I went all in. Through gritted teeth, I made countless cold calls. I reached out to local news stations, schools, and businesses. I drove all over town to meet potential leads, sometimes speaking with them for over an hour, only to learn that they had already committed their child to another summer program.
Slowly but surely, I found my rhythm. With each rejection, I became stronger. I didn’t see myself as a shameless salesperson making empty promises, but rather as someone offering a service that I genuinely believed in and knew I could deliver on.
The laughable pay aside, the lessons I learned that summer were invaluable. I learned to push my limits. I learned I already possessed the confidence I yearned for. Above all, I learned that when it came to my passions, nothing could stand in my way.
At this point you may be wondering, if I loved teaching so much, why didn’t I get a degree in education or start my own business right after graduation?
I’ll start with the easier question of the two. I didn’t pursue an education degree simply because I attended a school that was renowned for its commerce program. I didn’t grow up around business-minded parents. In fact, I didn’t even consider business school when I applied to college. However, the program ranked in the top three nationally, and that was all that mattered to me.
As a quick aside, misguided motivations is a common theme in my life. I’ve always gone after prestige and society’s definition of success, never stopping for a second to think about what made me happy.
Sure enough, almost from the moment I entered commerce school, I was confronted with the harsh reality that I was not a good fit. The emphasis on active participation, the endless group work, the expectation to network relentlessly all shoved me out of my comfort zone. Everyday was sink or swim, and at times, I felt as though I could barely stay afloat.
As for why I didn’t start my own business upon graduation, the short answer is I’m as traditional as they come, a rule follower to the bone. The norm out of commerce school was to get a “real” job, usually in Investment Banking or Consulting. Since I had ruled out I-Banking very early on, my options appeared limited. Again, this was just my perception of the opportunities available to me, but my 21-year-old self was in no way mature enough to have the necessary foresight.
Over my three years in the traditional work force, I’ve interned at a small company, worked for a large corporation, and experienced life as a traveling consultant at a Big Four. What I’ve seen has been eye opening.
I should also mention that I had no intentions of tutoring anymore. But as luck would have it, that path came looking for me. Someone had kept my contact from one of my marketing efforts two years prior and reached out. The timing worked because my job at the time was relaxed and provided great work-life balance, so I took on that student.
The next thing I knew, one became a dozen. Through word of mouth, my student base grew steadily. It became harder to keep up with the schedule, as I was working full-time during the week and devoting a lot of my weekends and even weeknights to teaching. Still, I loved it. I was once again reminded of the sense of accomplishment I could only get from teaching.
This next part is somewhat inexplicable. Even though my business was growing, I wasn’t quite ready to devote my all to it. I had been at my job for over a year at this point, and many of my friends had already jumped ship. They had transitioned to big-name companies that offered more challenging work and higher pay. That little girl with a skewed sense of success came back to haunt me; the nagging voice deep inside convinced me I wanted the same.
So, after nearly two years, I left my first job for what I claimed to be my dream company since the latter part of undergrad. I was elated to get this opportunity, one that I fought tooth and nail for. I finally felt validated, like I could stand by my business degree. In exchange, I made a conscious decision to step away from tutoring so I could focus on my professional career.
But a short year later, I found myself once again in a desolate state. Only this time, I didn’t have a direction. Sure, there were still more reputable companies out there, many in fact, but I knew deep down that’s not what I was searching for. I had been looking for fulfillment in all the wrong places. That’s why any sense of contentment was temporary at best.
I had to break the cycle.
The Turning Point
As is often the case, my turning point happened unexpectedly, and in two parts. It was so subtle that I was only able to make the connection months after the fact.
It was a Thursday afternoon in late September, 2015. Those who have traveled for work may be familiar with the 3-4-5 schedule. For me, it was to get on a train first thing Monday morning, arrive at client site, stay until Thursday afternoon, then catch a crowded and often delayed train home.
Like a robot, I hopped on train #85 after a particularly trying day. After the usual conundrum of finding a seat, I plopped down in what appeared to be the last available space. I looked at my phone to find a missed call and voicemail from a number I didn’t recognize.
In an attempt to hear the message over the rumbling train, I maxed out the volume on my phone and was able to make out just enough of the words to get the gist. It was from a new parent who had heard about my tutoring and wanted help for her son. This was not news to me; I had received many similar calls and emails in the past, but what surprised me was my reaction.
The moment I started to comprehend the message, I subconsciously shook my head, muttering to myself, “I can’t… I don’t have time.” I had already taken a few months hiatus from teaching, and had reluctantly decided to give it up for good.
Then, a chill ran through me as I caught myself. I thought, “Why the heck not?! Why was I so willing to give up the one thing I took the most pride in, for something that simply wasn’t my calling?”
That was my first moment of clarity.
Fully aware of how my thoughts could quickly spiral out of control, I decided to text my friend and then colleague (we called her Moose), who was one car away. She made me sit with her so we could talk it out. And right there, in the middle of a crowded train, I broke down.
I struggled to get the words out, but Moose understood. I’ll never forget what she said in her effort to comfort me.
“Get it together! It’s not that big of a deal. You should quit.”
Three short sentences that at the time were anything but what I wanted to hear. I couldn’t get it together. It was a big deal. And should I really quit?
It didn’t stop there. I made Moose promise not to tell others at work until I had more clarity on the situation. But a week later, our friend Roxy confronted me during a group “work” session. In a tone she had never used with me before, one that was both stern and caring, Roxy said, “Jen. We need to talk. I hear you want to start your own business?”
Completely caught off guard, I glanced over to find Moose smiling sheepishly before stammering out a hesitant “well… maybe…” and proceeded to share some of my thoughts. I then learned that Roxy had co-founded an event planning business while working full time. Over the next hour, she shared her insights on starting and maintaining a business and gave me ideas on how I can do the same while I was still traveling. Roxy’s confidence was contagious; our conversation left me feeling overwhelmed, but inspired.
That night, I came up with a list of to-dos. In the weekend that followed, I methodically began checking them off. Over the fleeting two days, I bought a domain, set up a website, registered “Prep with Jen” as a sole proprietorship, and mapped out a game plan for how to build my business. My progress gave me a renewed sense of purpose, and along with it, my second moment of clarity. I can do this!
Thank you, Moose and Roxy, for not letting me wallow alone in my misery. You snapped me out of my state of self-pity and helped me channel that into productive energy. Your kick in the butt was the very thing I needed to light the fire within.
Whew, if you’re still with me, thanks for making it this far! Now onto the last stretch of the marathon…The end of the story is rather anticlimactic. I wish I had some grand finale complete with fireworks. But as I stated in the beginning, I didn’t choose this path overnight. There wasn’t a major event that caused me to throw in the towel. Instead, it took a lot of wear and tear for me to arrive at my decision.
The truth is, we’re all creatures of habit. Even as someone who loathed traveling for work, after a year of living out of a suitcase, I became accustomed to it. Sure, I would have preferred to sleep in my own bed, but the commute wasn’t terrible and the per diem was definitely a nice perk.
In the months that followed my initial jumpstart, I fell into a sort of limbo. I continually wavered between accepting my life of mediocrity at work and leaving it all behind, but I just couldn’t make up my mind.
So I stalled.
And stalled some more.
The good news is during this time, I was making active changes. For one, I began to live more deliberately.
The game of politics continued at work. Only now, I let myself be fueled by my frustrations. Every disagreeable action prepared me that much more for the leap.
I also gave myself full permission to feel: anger, fear, and the many other emotions I had kept deeply suppressed in an attempt to be at peace. I welcomed all of them with open arms.
That’s when something miraculous began to happen. Bit by bit, I felt my entire mindset shift. It was gradual, but as real as could be. I started to view the world and my place in it differently. Instead of anger in my current state, I felt passion for the future. Instead of fear in the unknown, I saw opportunity. Without trying to sound too dramatic, for the first time, I felt empowered and in control of my own destiny.
So I’ve made up my mind to go for it, but when?
Risk averse by nature, I was that toddler who refused to walk until she was certain she wouldn’t fall. According to my parents, I was a late walker, but the first time I tried, I was steady, like I had been doing it my whole life.
When it came to my business, I wanted the same smooth transition. I told myself I’d leave my job when I reached X number of students. This was exactly the wrong mindset. I was already home only 3 days a week. In that time, I had to run errands, cook, and clean.
I was after all, a grown-up now.
In the blink of an eye, it was again time to pack for an early start on Monday morning. I still had some regard for my sanity and health, so this schedule simply didn’t allow me to take on the number of students I wanted to.
Along with that uncertainty, there also remained the biggest puzzle piece and the question any reasonable person would ask: “what about money?”
If I got a penny for every time that question crossed my mind, I would be free of financial woes.
I don’t consider myself a very materialistic person. Even if I had a lot of money, I’d still choose to rummage through the clearance section looking for treasure. However, if I’m being completely honest, having a consistent income and the freedom to buy what I wanted was addicting. I relished my financial independence and couldn’t fathom living any other way.
In preparation to leave my job for good, I began to hoard money the way a hamster hoards food. But I knew no realistic sum I could make would feel like a big enough safety blanket. I needed a final push, and it came in the most unexpected way.
If I had to identify the one event that tipped the scale, it would be the passing of someone very dear to me. She was my piano teacher when I lived in California, and for the 16 years that I had known her, she was like family. She passed away suddenly, a month before my planned visit to surprise her. I took an emergency trip out west to attend her service, and spent a good part of the day with her family in her house (calling it a home without her just doesn’t feel right). Her house was the first I had lived in upon coming to the U.S. From the moment I set foot into the neighborhood, countless memories, ones that I didn’t even know I had, began flooding back.
The conversations that day were bittersweet. We exchanged happy stories that celebrated her life. She hadn’t always been dealt the best cards, from failed marriages to chronic illnesses. Others in her situation might have struggled, but not Anita.
Famous for her big smile and fighting spirit, she defied the well-worn path, choosing instead to follow her heart. Anita filled her days with the two things that delighted her most: music and gardening. Even in her last days, she would cling onto her two true loves.
Returning home after that event, I knew what I had to do. As someone who wholeheartedly believed in pursuing her dreams, Anita would be saddened by the way I was living. Life is too short to be stagnant, too fleeting to be boring, too precious to have regrets. If I weren’t brave enough to take the leap for myself, I owed it to Anita to at least try.
Here I am, on my first day of self-employment. A part of me wonders if I’m out of my mind. Still, a much bigger part of me feels pride. I couldn’t find this elusive feeling when I got into college, when I graduated, or when I locked down a job that put me on my perceived path to success.I was supposed to do all of those things.
Yet sitting in my room, with no promise of a steady income and no idea what the future holds, I’m genuinely proud – of my strength, of my will to fight for the life I want, the life I know I deserve.
I’ll end here with a snippet. I really took to writing during my low points. There is something about capturing raw emotion in times of vulnerability that I find both powerful and therapeutic. This one is part of a letter I wrote just months after joining my travel project. It was intended for my boyfriend, but I never got the courage to send it. A true realist who isn’t always great with words, he has consistently displayed love and support through his actions, and for that I am eternally grateful.
I’m telling you this because I want you to hold me accountable for taking control of my future. These are not just words. This is not another one of those “big plans” that I obsess over for a few weeks and forget about. It’s a dream that only I can make happen. No matter if things at work get better, I want you to remind me what my true passions are in life. Never let me get complacent. Never let me settle.”