90 Day Letter to My Former Self: Tips and Tricks

Insights / leadership, management, development

90 Day Letter to My Former Self: Tips and Tricks


90 day letter to former self: Tips and tricks I wish I would have known when I started at August and for new Gustos

Hey Monique!

You finally moved to New York and found a job with a 20 minute (or 15 minute if you really move those legs of yours) walk to work! Wahoo! I would say “Yay, congrats you finally made it!” but that would imply the goal was simply to get a new job in New York; in reality, this is just the latest stop in your journey. Your next several months, and probably the rest of your time at August, will be a thought provoking, challenging, and wild ride. Buckle up.

It will be thought provoking because you will deeply question organizational systems. Broadly speaking, you’ll wonder if humans are attracted to hierarchical models from a biological standpoint or if these systems are simply the latest structures used to organize and produce products, ideas, etc and thus their popularity? You’ll wonder about how people function within these large and small organizational systems — what are the core human benefits (e.g., security and possibly good managerial support) and drawbacks (e.g., lack of autonomy and inability to explore new and different methods to develop products/ideas). What is the purpose of hierarchy implicitly and explicitly, both in terms of the work and how individuals are structured within an organization. How or should the system change? Where does the power and methods exist and persist to enact change? (Given your own pessimism and cynicism about when/if people and systems can change, this will be a fascinating idea you will continually explore). And, you’ll also have the usual suspects in terms of questions, such as are your abilities suited for this type of work? How does your gender, race, and upbringing interact with the August theory and philosophy on how people should work together? Oh yeah, and the world is constantly evolving so your perspective on these vague questions will definitely change too. Do these topics confuse and/or overwhelm you? Get used to that feeling.

The unifying red thread is that you will dissect why certain structures exist and persist in society, and how these structures, systems, teams, and leaders may evolve in tandem to navigate rapidly shifting societal, cultural, and economic norms. You will want to unpack those larger questions, understand why hierarchical models have endured, and, more interestingly, how these organizational systems have seeped into American society, the individual psyche, and yourself. An overarching anthropological question (I studied Anthropology in college, FYI) is: Does society, or any specific culture within that society (think of culture broadly as a set of beliefs, mindsets, practices, values, and social structure- any organization technically has a culture) sculpt what and how an individual perceives and acts? Or, is the culture born out of individual action? You will ask yourself these questions regularly in relation to the self organizing company you work within and the organizations for which you work. Regardless of how confused and overwhelmed you may feel, you will also like the intellectual rigor. In the best way possible, it will remind you of your college days. Because at August everyone is a learner, always reading, discussing, and grappling with new concepts. This will suit your need to question and tease ideas apart.

It will be challenging because, aside from confronting demanding intellectual questions, you are early in your career and still trying to find your voice. Working at a self organizing company with technically no boss, switching careers, and surrounding yourself with intelligent experienced people will intimidate the shit out of you. But growth comes when you find your “edge”. In yoga your “edge” is the point of discomfort when you push yourself a little bit deeper in a posture or pose — even when you feel like you literally cannot budge any further (embarrassed I’m making a yoga reference here, but roll with it). It is when you feel your “edge” that you become more flexible and stronger; and more aware of your actual and perceived limits. Part of the reason an individual’s “edge” is hard to embrace is due to fear- fear of failure, pain, inability etc. But, instead of focusing on your fears, soak in all the ideas swimming around you, learn from the talented pals on your team, and feel your perceived “edge”. Because, that is where you will learn what your own voice sounds like. And, to be clear, understanding and hearing your own voice will always be a continual process, both on a personal and professional level.

It will be wild because you are shifting from living in a relatively small city and working at a large multinational corporation, where feelings are essentially banned from the office, to a small, self organizing company in a huge city with a passionate, kind, smart, energetic, opinionated crew of folks. This will take a little getting used- you will almost feel like you are not at work because you can actually say when you are frustrated with something, or that you stayed out too late last night. No one will judge you. They will listen, support, and maybe even have gone out late with you.

It will be wild at work but in life, too. You’ve also never lived in a big city before and you have an awful sense of direction; get ready to be lost most of the time in your first few months…or just in general because your poor sense of direction ain’t improvin’. You’ll have to deal with the drama that is New York City housing and cockroaches. You’ll realize that Sex and the City definitely didn’t include when Carrie was sweaty and lugging groceries up lots of stairs, or stepping in puddles of who knows what, or almost bumping into people who seem to be running, yet still look composed and confident (okay maybe the last part would be in Sex and the City). But really, where are they going?! You’ll also have more options for music, food, events, and conversations than you’ll know what to do with. You are going to have a lot of “Holy shit, this is pretty neat” moments followed by “Ugh, now I’m utterly lost on the subway and headed to deep brooklyn instead of Manhattan” moments. It happens. New York is going to give you a real education.

But most of all, it will be rewarding.



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