Leaving Shimmer & how I figured out what was next
An update on my career journey and some advice on making early career decisions in startups
Welcome to my first Substack post! I’ll be using my blog for two purposes: 1) updating friends on my life and 2) occasional posts around topics I find interesting, especially in career, health, and technology—please subscribe if you’d like to stay updated!
In mid-May, I made a really difficult decision to leave my company, Shimmer. We were going through a big pivot, and I found myself interested in a different set of problems to work on then my co-founders Chris and Vik—it made sense for me to leave and for them to continue working on it.
Afterwards, I had to figure out what was next for me. Should I go back to medical school? Should I build another company? Should I join a company? Work at a venture studio?
After two months and a half of searching and recruiting, I’ve decided to join Yury at his venture fund, Cold Start, as Chief of Staff. I am super excited to be learning directly from a successful serial entrepreneur and continuing to help founders build in the earliest stages of company creation.
A lot of thought went into my decision-making process, and I realized many of my friends were going through similar transitions themselves (what we’ve been dramatically calling the “quarter life crisis”). Over time, I think I’ve come up with a pretty solid framework to go about making these big decisions—so I documented some of these notes and learnings below.
Special thank you to all of the amazing mentors and friends who helped me along the way (Andrew Trister, Sherman Leung, Justin Norden, Sebastian Caliri, John Waldeisen, Allen Cheng, Annie Ye, Galym Imanbayev, Daniel Ha, Shiv Gaglani—y’all were immensely helpful in getting me here, I appreciate you all so much).
I’ve broken this post down into two sections: 1) my process 2) learnings along the way.
Separately—I get a lot of questions from people thinking about medical school so I thought it deserved a separate blog with more depth. In the next couple months, I’ll be working on a deeper dive on leaving medical school and alternative career paths & considerations. Otherwise, check out my previous posts on my reasons for leaving medical school & reflections on startups vs. medical school as a career path.
Ultimately my process can be broken down into six steps:
1) Sketch out a timeline
2) Take a break
3) Revisit what I want fundamentally
4) Identify characteristics of high-growth career opportunnities
5) Identify the roles I wanted to pursue
6) Iteratively gather information, recruit, & adjust roles of interest
1. Sketch out a timeline.
I first spent time figuring out an ideal and worst case scenario timeline for my job search. This deadline was helpful to motivate me to get things done in a reasonable amount of time and keep me from decision paralysis. I gave myself 2.5 months as my ideal case deadline (including a solid break). I had 4.5 months as my worst case deadline—once I ran over 2.5 months, I’d start worrying about my prospects and start considering alternatives.
2. Take a break.
I took my next job very seriously, I knew I’d dedicate at least 2 years of hard work to something, and it was important for me think clearly. I was still burnt out from the grind and I needed time to process leaving my company. I decided to go on a no-tech solo trip to the Adirondack mountains, spending the first half in complete silent mediation (some helpful resources here & here I followed, shout out to Ebenezer for some advice here), and the latter half spending time with myself reading (Time is a Mother, The Year of Magical Thinking, Interior Chinatown—all excellent reads), journaling, and hiking.
I found that this experience helped me think more clearly and detach my ego from past narratives or experiences that were a sunk cost (e.g. feeling like I needed to be a founder again just because I was one before, finishing medical school just because I was almost done, or working on things that I thought were hype rather than what I genuinely found intuitively interesting).
I still have a long career ahead of me, so I wanted to reset and be able to think clearly when selecting what I’d want to do without any bias from ego or sunk cost experiences.
3. Revisit what I wanted fundamentally.
The next thing I did was go back to the drawing board to understand what I wanted fundamentally in my career. I took this approach by examining both what I valued and what things I was energized by.
To revisit my values I took a look and made adjustments to my value statements (for those who haven’t done so before, highly recommend checking out the Brené Brown values exercises I found it immensely helpful). Currently, mine are:
1) Longlasting & meaningful work that touches the lives of many people in ways that empower and help them that I contributed significantly towards.
2) Being a whole, loving, kind, & intellectual presence in this world.
To revisit what I was energized by, I wrote down what I liked and what I disliked about the experiences I’ve had in my early career (thanks Annie Ye for encouraging me to go through this exercise, so helpful). I then went back and made a summary about what I found I enjoyed more and what I didn’t.
I used what my values are and what I was energized by as guiding points as I looked forward towards what I wanted to do.
4. Identify characteristics of a high-growth career opportunity
The next thing I did was try to figure out what made sense to optimize for in the next 2-5 years of my career to accelerate my growth.
I did two things to help me figure this out: 1) talk to mentors and 2) read a ton (hard thing about hard things, superfounders, were particularly helpful).
Ultimately I came up with the following four things (in priority order): people, mentorship, ownership, and learning specific, niche knowledge.
For me, the most important thing was finding stellar people to work with. Specifically, I view this as people I’d like to work with across my entire career. These could come in the form of lifelong friends, mentors, or future co-workers. I wanted to work with people I felt were competent, empathetic, curious, and ambitious.
Another reason people are important is because they may be people you sell to in the future. For example, if you’re in a client-facing role, you might develop a powerful network to sell into in the future (one good example is when you’re an insurance broker or consultant).
One heuristic is to visualize the room you’ll be sitting in (thanks Daniel Ha for this piece of advice!). Who will you be interfacing regularly with? What types of interactions will be had in the room? What are you learning?
I believe mentorship is one of the most efficient ways for me to learn and grow into a better company builder. I wanted to make sure whoever I worked under believed in me and wanted to help me reach my fullest potential. I also had to feel like they were someone who’s work I respected and aspired to learn from.
Having ownership and accountability over my work would help me learn to do things on my own, and also help me establish a reputation for excellence amongst the people I work with.
Learning specific, niche knowledge
Knowledge around specific, niche topics or industries make you uniquely valuable. For me I thought of these as the following:
intuition around people you’d sell to
the under-belly of healthcare as a business
intellectually interesting topics that I wanted to keep learning about
I also spent some time thinking about the things I tended to over-index or bias towards. A lot of my thoughts here were shaped by these essays   by Erik Torenberg, how to do what you love by Paul Graham, and the almanack of naval ravikant. I also thought through a lot of my own personal experiences growing in an immigrant household and how it influenced my perspectives.
For example, two of these were:
Paul Graham talks about this in detail, to summarize:
Prestige is essentially just the opinion of many others— when what matters most is the opinion of those you respect and are surrounded by.
Prestige warps what you truly desire to fit a specific mold of what others believe. For this reason, if deciding between two options where one is prestigious and one is not— you’re likely interested in the non-prestigious option for reasons more intrinsic to the work.
If you pursue what you’re uniquely interested & talented in, you’ll make it prestigious (think about the genesis of most art forms or any sort of innovation).
There are exceptions of course. I grew up with parents that were highly educated immigrants to America. For them to succeed and be trusted, degrees and education were the best way to do this. However, because of this, they impressed the importance of prestige upon me, and I grew up with a deep bias towards prestige.
Status, Hype, Money.
This follows a similar logic as above. For me, I wanted to avoid things like status or money which would pull me away from working on stuff I felt I was uniquely interested or good at. I believe success and happiness (as well as status & money) followed working on something I loved and could excel in delivering to the world. Unfortunately, not everyone has the ability to make this choice; it’s very dependent on your personal situation. For example, I know people who have to financially and emotionally support a family member with a costly medical condition.
5. Identify the roles I wanted to pursue
With all of this thinking done I was ready to come up with a couple of roles to shoot for.
Ultimately, I realized I wanted to stay in the startup ecosystem. The potential for large impact & upside, rational & fast-paced culture, and ownership were all things I loved about startups. I narrowed it down to three things:
I was interested in incubating/investing roles at funds. Investing would allow me to learn the larger picture of healthcare, while I’d still get to spend most of my time building companies internally with oversight from other partners. My main concern with these roles was that most healthcare venture studios are newer without many proven exits yet. Some examples that I looked at: 25Madison, Alleycorp, and Atomix.
Product management at early stage startups
As a PM I’d get to hands on own a product and ship it off in a structured environment. I’d get to work closely with people with experience doing this many times, and learn a lot about the users that we served. It wasn’t easy figuring out which startups were an ideal fit to join, so it required a bit more digging and leveraging connections to understand how they were doing. Some examples here: Medallion, Ribbon Health, and Headway.
Chief of staff under “Super-founders”
As the chief of staff to a second-time founder of a successful venture, I’d get hands on training for company building, with opportunities to move to VP, founder, or investing roles later.
6. Iteratively gather information, recruit, & adjust roles of interest
The next thing I did was recruit aggressively, and during the process continue to adjust things related to steps 3-5.
While recruiting I was constantly gathering information to help understand what types of companies I wanted to work for while also moving further along in their pipeline.
Some information I found useful:
talk to employees in similar roles & investors in the space/company
talk to the person you’d work directly under for a coffee chat
use the values and the things that energize you from step 3 as a guide (e.g. what it’s like on the day-day, what types of people are you going to be surrounded by, etc.)
ask about things that’ll help you see if the role aligns with career goals
read and do some research! Some things I found helpful: Crunchbase, the All-In Podcast, SuperFounders, and I also read a bunch of articles on health tech and product management.
I maintained a CRM on Notion and spoke with over 40 companies in the process. I also had a small rating on how I felt “intuitively” about the company (did the problems interest me or not)—this helped me learn more about what types of problem areas interested me intuitively.
After about 5 weeks of this process, I was able to make a decision I was really excited about that matched my 1) values 2) things that energized me and 3) career goals. This all came together when I met Yury and decided to join him at Cold Start!
Things I learned along the way
Figuring out what you want
Patience! Your whole career lies in front of you. Take your time between each job switch, you don’t get many of them, and if done properly, you’ll be much happier and move more quickly toward a position you desire.
Focus first on what values you care about (check out the Brené Brown exercises) and the things that give you energy. Afterwards, use this to help you think through career goals. You’ll be in a better position at that point to look at what specific roles might make most sense to pursue for you in the next 2-3 years.
Remember your journey & approach is really your own. Wandering a path different from others may seem scary, but it also can be your advantage. Leveraging your own unique set of skills, experiences, and talents are what makes you scarce and invaluable.
Consider spending time in the early phases of career going in orthogonal directions (thanks Jessica Ji for this piece of advice!), that way you have data to work with that’ll help you hone your values and intuition on what you like, and fully dedicate to something more specific over time.
For me, I found that searching for a high-growth early career opportunity often meant looking for awesome people, mentorship, ownership, and niche/specific learnings.
Thinking through trade-offs
Where do you sit on the optionality vs specificity tradeoff right now? Going for optionality allows you to stay nimble and flexible, but not really have any expertise, while going for specificity narrows your options in the near-term, but you become an expert in a specific function. I used to go more for optionality (e.g. get degrees and figure it out from there), however, over time, I found something I enjoy much more (building startups). One perspective is that specializing often opens up more doors to have options in the future. Once you can produce excellent value in some sort of way, you often can then move to other areas that interest you much more easily (eg. founder → VC, doctor → CMO, SWE → Product). A somewhat paradoxical tip I learned: there are lots of ways you can specialize in something while also explore in orthogonal directions (e.g. specializing in product but exploring different industries or specializing in one industry but exploring different roles).
Spend some time thinking about the things you tend to over-index on. For example—prestige, status, hype, money, vanity metrics (valuation, top-tier investors) were all examples of things I felt I had an inclination to over-index on (partially due to how I was raised, partially due to the social environments I was surrounded by).
Read as much as you can while you have the time. Try rating things you consume (or companies you interact with) to get an understanding of what things you like or dislike. This knowledge compounds over time.
Make a decision, and dedicate yourself to excellence for 1-2 years if you can (thanks Justin Norden for this tip). This ensures you develop real skills and experiences you can take with you to the next chapter, and also become known for excellence amongst the people you work with. There are exceptions to this (e.g. you realize within the first 3 months this is absolutely a horrible fit).
Provide value back to the people who helped you (thanks Sherman for this one)! These are long-term relationships and people are taking the time to help you. Did you discover anything interesting about diff companies along the way? How did the intro go?
Follow-up! A lot of these startups are swamped and only pushed me to the next round after I followed up.
VC are your best friends when looking for startup jobs, they usually understand which companies are doing well and will help you evaluate prospective companies you’re interested in.
Shameless plug: We’re hiring founders and product leaders to build new businesses and products at Cold Start (with competitive compensation), reach out if you know anyone interested in a unique opportunity to build in a truly entrepreneurial & high-growth environment.
Thanks for reading! More to come soon on my thoughts around leaving medical school and alternative careers to consider.
Congrats Jon - so exciting to follow along your journey and looking forward to cheering you on in this exciting next chapter :) a warm welcome to the world of venture studios!
Great story, I spent 17 minutes in my life, try to understand the message you want to give us,
Sharing is the Caring, you are a good person, I wish you have more greatful power than now,
you always think out of the box, you are too familiar than I see you.
Looking forward to hearing from you more, hopefully soon I might reach you