How I Decided Between a Startup and Management Associate Position for My 1st Full-Time Job
And Some Strategies and Considerations for Those Faced with a Similar Decision
Two Roads Diverged…
I recently had to make a decision between taking a management associate position at a large healthcare organization and a first-employee role in an early-stage tech social enterprise.
While the two seem, and likely are, worlds apart (I always thought I would have narrowed down my interests and aspirations by the end of college, but here we are), both fit my job search priorities of building career capital and having social impact. Additionally, the various pros and cons of taking each offer seemed to balance out evenly.
Agonizing over which to take over a week and a half was definitely not an unfamiliar experience for me. I remember losing sleep over whether to go to the liberal arts program at Yale-NUS or attend a pre-professional program elsewhere.
Deciding whether to declare a psychology or environmental studies major (I still tell people I have a degree in psychology and environmental studies). Whether to do an internship in Singapore to get more contextually relevant experience or in the US for a more unique and eye-opening one. Coco Crunch or Honey Stars for breakfast.
You get the picture.
Some would say I like to have my cake and eat it too. And I really do! The feeling of missing out over the road not traveled sucks because of all the what-ifs and could-have-beens.
On the flip side, the toughness of these decisions often reflect how solid both choices are, and that we would stand to gain a lot regardless whichever one we end up taking.
Heuristics & biases
As a psychology (and environmental studies) student, I am also aware of the heuristics that make decisionmaking unnecessarily difficult or problematic.
Granted, with the exception of breakfast cereals, these choices do have moderately significant consequences, opening some doors and closing others.
While it is the journey that matters and not the destination, it does feel like a lot of the journey is determined by which destinations we select.
However, understanding and being aware of these heuristics did help in making a better decision.
The main heuristic at play here was obviously loss aversion, as I was focusing a lot on the things I was losing out on. While I do think this is helpful as it highlights the areas I would be negatively impacted by, it can also make the choice feel like a lose-lose situation.
Since the choices were so evenly matched, it is likely the case either one would work out, and choosing to focus on what is potentially gained instead of lost can be what makes the decision feel like a good instead of a bad one (or at the very least a future-creating instead of a future-ending one).
I also realized I was potentially falling prey to an anchoring effect created by the management associate offer, which came first and made the starting salary of the startup offer seem lower than what I might have perceived it in isolation. This could have further triggered loss aversion, framing the startup choice as a loss of the salary difference.
On the flip side, my experiences so far at the startup also anchored the level of autonomy and flexibility as the ground level and could have made me overly focus on their potential loss. However, it is worthwhile to note that these anchoring effects were the result of both organizations extending to me a vote of confidence (by giving me an early offer or by spending precious time and energy to trial me).
Still, identifying these mechanics were important, as it grounded me back to my priorities in the career search, which were career capital and social impact, meaning I was giving salary and organizational culture more weight than I would want to.
Mere exposure effect & sunk cost fallacy
Lastly, I was cautious about how the the mere exposure effect and sunk cost fallacy could be impacting my decision. Because I was already working with the startup as part of a trial period, I had definitely come to develop some attachment to the people and the work and would weigh it more positively.
Additionally, this also placed me in a position where I had some investment in various projects that I had taken on or initiated and wanted to see through. Recognizing these two things helped me compare both options more objectively.
Making an informed choice
Now that I was aware of the heuristics that were likely underpinning my considerations, it was time to make a more informed choice based on more information.
Asking for advice
The first step was to talk to other people to get their advice and opinions. There were three groups of people whose brains I picked.
First, I found it important to talk to mentors who have had to make a similar choice in the past, and/or had more domain knowledge regarding my considerations. (Some useful tips here on how to best engage with mentors.) This also includes resources that are out there which can serve a similar function, such as this pair of articles.
Obviously, with these resources, it is important to understand what might not be contextually relevant or applicable. This group also included those from the startup, whose advice were especially insightful and I greatly appreciated despite the potential conflict of interest.
Second, I talked to people who know me and what I would like well, and could offer me a more objective perspective outside of my heuristics. This group also included mentors (but of a different kind), as well as friends and family members. When talking to this group, it was important to recognize that they likely had different perspectives and notions of success (especially family), which could influence their advice.
The last group of individuals I sought advice from included others who do not know as much about the decision factors or what I want. While this might seem somewhat counter-intuitive, I felt that their distance from both domains could give me a fresh perspective that might surface previously unconsidered factors.
Putting it to a number
Now that I had identified factors affecting my decisionmaking process as well as heard multiple perspectives on what others thought would be the best course of action, it was time to weigh both options and their various features side by side.
I constructed a table with four columns: job characteristics, importance to me, and a score for each position. These characteristics included items from growth opportunities and team culture to commute time and healthcare benefits. The advice that I had received also came in useful here for scoring these items, especially the ones I could not presently get a sense of.
Adding up these scores, which were weighted by their importance to me, gave me an objective manner by which to evaluate the two options, and the results pointed to the management associate role.
Imagining two futures
One final test I did was to see what my gut was saying at this point. While heuristics can lead to flawed decisionmaking, they can also be critical because they tap into drives and emotional responses that lie in the sub- or unconscious realm.
As such, I decided to do a one-minute freewrite for two imagined scenarios, in which I ended up choosing each option. This surfaced my considerations and priorities and allowed me to see which I was more enthusiastic about.
Freewrite for the startup role
Ultimately, I decided to go with the startup because while the learning environment was unstructured, I know I enjoy working and thrive in small teams and having autonomy and responsibility. The startup also allows me to potentially build towards product management in tech (which is something that I am interested in and is hard to get into), as while I would be doing more of a marketing role initially, the team has informed me that I would be able to work on product tasks as well and possibly head new products in future. While the base salary is substantially lower, it is not a priority and the equity I get will even it out in the long run as I believe the startup will continue to find success. The healthcare institution might further pigeonhole me into the health sector, and make it harder for me to get a similar opportunity in future, or have to start from the same point again. I also think the much shorter commute time and increased flexibility in working offsite and in dress code are significant quality of life benefits that come with the startup role.
Freewrite for the management associate role
Ultimately, I decided to go with the management associate role because I can afford to take the risk of leaving behind something that I am comfortable with to explore working in a bigger structure, which I am unfamiliar with. The structure of the program and inherent in a big organization also means that I will get to learn from established practices that work at scale, and not be as limited to what I can already do or understand. Additionally, the downside of being stuck in a specialized or routine role typical of large organizations is mitigated by the fact that it is a rotational program. I am okay even if I realize that the management associate program or the organization isn’t for me, as I would have a better idea or what I want as a career and then be able to reorient myself, be it back to the tech startup scene or elsewhere. I do not mind starting from ground zero again in terms of experience or seniority if it means I am clearer on what I want. While the commute is very long, I think I could make use of that time to do things like read or listen to podcasts, or find out more about the carpooling I heard about, which could let me meet more people as well. The significantly higher salary and health benefits are also good to have as it would give me more financial security and serve as a nest for my future endeavors.
The final decision
Armed with all these insights, I decided to go ahead with the management associate position. Would I be as happy or happier if I had taken the startup role? Possibly. But now I can set my thinking cap down till the next fork in the road — or till I sit down at the breakfast table tomorrow.