Balancing Hard Decisions in My Career
Note: This blog post was originally written around April 2023.
Lately, I’ve been bogged down with deciding what to do for the summer.
I was presented with four great options:
Next36 —> an entrepreneurship program co-founded by a Harvard professor and a Rotman professor, both of which have and/or currently run innovative startups.
AWS (Amazon Web Services) —> touches on one of the main tech innovations of the future: cloud. And of course, a big brand name.
Sezzle —> to continue with my current internship at a great startup. Though, I’ve already crossed out this option after realizing I’ve already learned quite a bit from the job.
A Korean Generative AI startup —> a cool startup and opportunity that I crossed out due to their vanity metrics and questionable decision-making (e.g. why would they try to hire me, a student, to lead their Japanese expansion?).
Of course, I know in my head that there are benefits and cons to each:
Next36 would provide me with a great network of peers, mentors, venture capitalists, teachers, and successful entrepreneurs. I could pitch for money, fail fast before building later startups, and feel not-as-lonely in the entrepreneurship journey by surrounding myself with people who were also trying to build something larger than themselves.
AWS would give me credibility when I try to raise capital for my startup in the future. It would give me leverage and leeway in opening many doors, whether I want to work at a big tech, fast-growing startup, or international company in the future (e.g. in Korea for a bit). It would also be a great opportunity to learn from the mindsets of CEOs and senior executives to whom I would try to pitch in the future.
Continuing at my current internship would allow me to continue learning about user interviewing and experimentation to improve user experience.
The Korean generative AI startup would be a cool way to take ownership of a large business project, get my name out there, and open up the door to possibly working in Korea full-time after graduation in a non-teaching job.
I’m blessed and thankful to even have a choice — let alone all these great choices (especially in this market).
However, after consulting with multiple trusted friends, professional mentors, and my gut, I realized there were four main options based on the first two).
What My Gut Says About Each Option
I’ll go into each option — but rather than the logic of each, I’ll delve into how they make me feel (aka what my gut says).
1) Next36
I felt like this would be a chance to prove myself — to myself, of course. To prove myself that I believe in myself enough to forego a summer’s worth of salary (mind you, the long-touted “most important summer of undergrad”) and the opportunity cost of not doing an internship in order to bet on my abilities to build a company and produce results that surpass what I could do in a corporate company.
At the same time, I felt like this aligned with my 2023 mission to fail harder but also succeed at higher levels. I would really put my iteration and design skills to the test because there was lots of room for error in product development.
I was scared that, if I don’t accept Next36, it would virtue signal to myself that I don’t believe in my abilities to start and run a successful business.
2) AWS
Honestly, I fully expect this experience to be mid. It’s a corporate role, meaning you’re likely to work on unimportant and/or not urgent projects (god forbid pet projects), but I knew that the brand name was such incredible leverage in opening multiple doors at once. It felt like that stamp of quality control / standard of excellence that I lacked from my education (because no one knows Western in America or Korea) that I could finally receive now.
I also knew that, despite learning being more important than salary to me at this stage of life, the income it provided me will give me greater freedom to re-invest in myself.
Most importantly, this felt like a once-in-a-lifetime chance to prove myself — both to others and to myself. For the longest time, despite interviewing at companies such as Microsoft, Meta, and Linkedin, I kept getting stuck at the first stage: the phone screen interview. Normally, these calls ranged from 15 to 30 minutes, and I was always baffled at how poorly I must perform on interviews to be failing at these simple behavioural calls. Therefore, when I got notified that I got off the AWS waitlist (meaning I passed their bar of excellence but wasn’t immediately a preferred candidate), I knew to some degree that I got lucky enough for someone to pass up this opportunity and for me to receive it.
I felt unsure about my abilities to land another big tech internship if not now. After all, I’ve heard that the chances of getting into FAANG are lower than that of getting into Harvard.
At the same time, I was also concerned that I might be leaning too much into other people’s opinions and validations by playing it with this — the “safe option.”
3) Both
Although I had some close friends and mentors recommend that I try to do both (and tell neither of them about the other), it just didn’t sit right with me deep down.
I know I value honesty, and it would feel off to me to lie to both parties while living out the summer with the anxiety that they may find out and burn some bridges if so.
Even though it would provide me with the maximum benefits on paper — the entrepreneurship network from Next36 and the professional credibility from AWS — I knew deep down that it wasn’t ideal because my focus would be so all over the place that I would be able to do neither well. I’ve half-assed enough things in the past to know it doesn’t end well.
“Daniel Kahneman once said an important part of becoming a good investor is having a well-calibrated sense of your future regret. You need to accurately understand how you’ll feel if things turn out differently than you hoped.” - here
4) Neither
This is what my gut was initially leaning towards. I wanted some head space for the summer to feel like I actually have time to study, catch up with friends, and breathe. To re-center myself after always being on the go and looking forward to what’s next.
However, I knew that logically, this wouldn’t make sense.
It would just be some ideal to strive towards — like a white room away from the world where I could enjoy my own peace free from the pressures.
Yet, I knew deep down I would get bored of it after 2 months and that the lack of structure would make it even harder for me to learn in my free time.
What I Realized From Chatting with My Therapist
My therapist actually serves as the perfect mirror for me.
Despite being only 3 sessions in, she is skilled at knowing when to listen and let me ramble vs. when to slow me down and bounce back patterns in what I have said.
Through chatting with her, I realized that going forward with only AWS would serve my needs best at the moment.
In the process, I also realized three main things:
The greatest thing holding me back from letting go of Next36 was fearing how the program coordinators would react.
In particular, I did not want to disappoint the Director, President, and Co-Founder of the program as they each personally interviewed and selected me into the cohort from amongst a pool of competitive applicants. I didn’t want them to perceive me as being a “cop-out” who sold herself out to golden handcuffs.
Moreover, I wanted validation from the Harvard lecturer and serial entrepreneur Co-Founder that I wasn’t just a “false positive” selection into the program but that I indeed could produce and sell a great product. My therapist helped me realize how I will just need to let go of these opinions and stick to following what feels right for me.
Not only was I operating from a bit of a scarcity mindset, but I was also seeing things as if they were black and white.
I didn’t realize this until she pointed it out, but I was assuming that if I did AWS, it would mean that I’m “bad” at Next36 (and entrepreneurship in general). I thought it was an “either-or” scenario when in reality, I can be good at both but simply find that one opportunity has better timing than the other.
Just because I don’t feel ready to start my own business now, doesn’t mean I won’t be ready in the future. Sometimes, it’s okay to take a step back to learn more (especially to learn on other people’s dime first) before diving head-deep into building your own solution.
The greatest barrier I wanted to tackle mentally was convincing myself that I can take a project beyond the prototype phase.
In the past, I kept getting stuck on the prototype stage, where we would have a great idea and have a close-to-perfect mockup on Figma, but we would never deploy the solution enough through code to use it as a fully-fledged product. As a result, I had a limiting belief of myself that I was “someone who cannot finish her projects” and “someone who struggles with commitment and discipline.”
An additional part of this is that, as a natural creator, I don’t want to create under the timelines of others. While I think it’s great that Next36 helps accelerate the product development lifecycle by conducting progress check-ins and lecturing about things such as incorporation strategy, I don’t want to create for the sake of creating. Instead, I want to plunge full force into a product I am genuinely passionate about, can see a problem in, and for which I am the right person to solve. I want to be intentional with my time, space, and energy.
My Priorities
Being the last summer I have before I go full-time in 2024, I had two main priorities on my mind:
1) Create a mental space for myself where I can genuinely relax, reconnect with myself, and learn what I want to learn
2) Expedite my growth by doing things that will catalyze my learnings and skills exponentially (not just linearly)
The Decision
I ultimately decided to call up my program director at Next36 and tell him that I can no longer do the program because I don’t want to half-ass a program in which I get what I put in.
So, how does AWS align with your priorities?
1) Mental Space to Learn (and Breathe):
Instead of taking on too many things at once, I can finally focus on doing an internship for the end of May to mid-August while taking most of May and the end of August to read about topics of interest (e.g. entrepreneurship, leadership, team building, EQ), study product management frameworks, and practice my interviewing skills. Although there will definitely be some roadblocks along the way, it feels more reassuring to incorporate some of that mental space I sought in option #4.
Next36 would also ramp up immediately from part-time (since February) to full-time in May, which means no downtime to catch up with my learnings and re-connect with who I am before I jump into “the next thing".”
2) Exponential Learnings:
At AWS, I could network with people who may become my future co-founders, colleagues, and/or investor. Learning how these big tech employees think is valuable systems input for when I foster my own company’s culture in the future.
Declining Next36 would also give me more freedom to fail (and succeed) at my own rate while testing my ideas here and there. I could always take my venture full-time in the future should/when I build enough traction and runway.
I could max out on reasonable free time (a sweet spot between too much free time and too little free time) by using the non-internship parts of summer to study up on topics I was curious about. These learnings will compound and help me reach even higher heights in the future.
The Takeaway
Hard decisions are, of course, hard to make.
However, what makes them easier is having the right person to soundboard off of where they don’t have a stake in your situation and can listen (and reflect back at you) from a neutral point of view.
While it’s great to collect the opinions of people you trust, at the end of the day, trust your own judgment and intuition. Ever since I finally made a decision between the two, I have felt lighter in the way I carry myself and more authentically aligned with who I am. Although I will never know if this was 100% the right choice, I hope to move forward by doing my best in the role, side project, and self-learning. At the same time, it’s okay if this decision doesn’t pan out like how I expected it to, and I should show myself enough grace and acceptance to love myself regardless.
It’s tempting to take on more (especially as it’s always how I’ve done things), but I’m learning to differentiate the trivial many from the vital few.
After all, focus is the name of the game.
"Focus starts with elimination, improves with concentration, and compounds with continuation."
- from James Clear’s email newsletter
Update: I was struggling to find a problem space that feels in alignment with my passion and skills for the longest time, but after doing some deep work this morning regarding my “Deathbed Regret List” (more about this later), I think I’ve finally found one that really lights me up: I want to help upskill the workers'/tourism economy in South East Asia (especially Vietnam, Phillippines, and Thailand). I still need to research into how I would do so (e.g. through a mentorship/networking program, funding injections, online coding classes subsidizing, etc.) but I am SO EXCITED to potentially explore and tap into this space.