9 Month Letter to Self — Lessons from Life at August

Insights / future of work, self management, self organization, startup life

9 Month Letter to Self — Lessons from Life at August


Hello Justine of August 9 Months Past — it’s Justine of August Present (literally, its August 1st today). This was originally supposed to be written to you when you had reached 90 days at August (the company), as a way to share my hard-earned wisdom as an newbie Gusto…but clearly I’ve sailed way past that point. But better late than never!

Reflecting back over the nine months, a lot has happened.

You’ve joined a team of some of the smartest people you’ve ever known, who are relentlessly curious, continually thoughtful, nice as heck and fun to boot– not an easy combination to find. You feel like you fit in here more than you have at any other company or school you’ve been a part of, and it feels damn good.

You’ve learned a lot and grown a lot — but also have helped the company grow too. You’ve leaned into that consulting skillset, built your exposure and client chops across three major corporations, gotten to work with across all levels/functions of an organization ranging from HR, Marketing, Operations up the chain to the Executive team, embraced work travel (Paris was a highlight, but Plano, Texas was pretty fun too), and have brought your experience developing evaluation programs to help August grow its own ability to evaluate and assess the success of its work.

You’ve really felt the combination of your MBA + your previous work experience come into play, and that feels GREAT. In general, just by doing what comes naturally to you and what you love to do, you’ve generally been able to thrive and help the company get better too. It feels like luck but you also remind yourself that you went through 2.5 years prior(and arguably, all years of career transitions before that) of deep soul searching to get to this point and so, yeah, while luck played a role, a lot of it was the work put in along the way. It’s all very millennial — pursue your passions and it will work out!

Startup life doesn’t come naturally to you — but it’s what you needed.You’ve always worked in a weird hybrid of small startup division within big company — and there’s a reason the big company was always there. You thrive as an intrapreneur and like the complexity, the politics, the bureaucracy — its all a big, fascinating puzzle to piece together. And, let’s face it, you love the anonymity that comes with being one of many. You’re an only child, raised to be independent in all your ways, and being part of a small, closely knit organism is really tough at times — particularly, given August’s relentless focus on transparency and openness. Everything you do is in the open, and people know and are giving you feedback on what you’re doing, making, and delivering at all points in time. It’s not a comfortable feeling.

But it’s also good for you — it’s helped you to be less perfectionistic, build closer relationships, and learn how to communicate better, how to collaborate, how to be flexible and adapt. And, the beauty of the work at August is that you still get that big company fun. You’re embedded on client sites more than half the time, so ultimately you’ve gotten all the politics, bureaucratic maneuvers, and complex system interactions an intrapreneur could dream of…but at any point when it gets to be too much, you have the comfort of knowing that August, and its culture, are really what drives your day to day.

You like self-management…but don’t love it (yet). Self-management is a tough beast to grasp from the outside — what is it really like? What’s this world of no bosses all about? You can read a bit more about the logistics of it in my previous post, but I would say that overall, the world of self-management works for you. You have the most autonomy and control over your own destiny (and the work you do) than you have ever had before. For someone like yourself who thrives on personal responsibility and drive, it feels great.

But, what doesn’t feel great is that for all the processes, systems and governance structures that we construct, humans are still humans. They are flawed and bring their previous experiences and biases with them. As your coworker Sasha has said much more eloquently, until we really do the work to understand and address our own biases, blind spots, and privilege, the same power and hierarchy dynamics that affect every other work place do affect August, and hinder the legitimacy of our self-organizing system. Our intersectional identities, as informed by factors such as race, gender, experience, socioeconomic status, personality, and disabilities deeply inform who holds power and how it’s exercised within our organization. It’s become very clear, particularly during our conversations on privilege, power and oppression over the past trimester, that we have a lot of work to do here.

That feels heavy, but what makes the fight worthwhile is that at August is that we have the space to have these tough conversations, and an organizational commitment to change — and that’s more than you can say for 95% of other organizations. Because the truth is that we as a self-organizing system will be fundamentally challenged if we don’t.

So — you have a personal responsibility to grow in your own ability to advocate and drive forward diversity and inclusion internally and with our clients.

It’s a big topic at August right now, as it should be, mostly driven by the efforts of a passionate and qualified few. But it’s something that we are all responsible for — creating an organization that truly represents the world we live in today in terms of the diversity of who we are and who we work with, and the culture, systems and structures we create to enable each person, regardless of what identities they hold, thrive and do their best work. It’s something we need to do for ourselves, as a company, and its something we need to help our clients do, to create a better world.

And there’s a lot that you can, and should do here. Your own hesitant and complex relationship to your own set of identities is something that you have always punted down the road to deal with at that “perfect” later time and it’s time to stop doing that. It’s time to step up and own who you really are, so you can be an advocate and ally for others who are trying to do the same. You’re writing this here to make sure you stay accountable to yourself and others as well.

Still reading?

Kudos to those of you who have made it down here this far! Because, truthfully, this 90 Day (9 Month) Letter is for both August Past me and you. Yes, you, staring at this Medium page — that person who either recently started at August, or wants a job at August, or are just deeply curious about this little firm you keep hearing about — like, what the heck is going on over there?

Hopefully I’ve given you one more taste of all that’s amazing and challenging at August, from my personal POV (for others, check out my fellow Gustos’ Krys, Usha Gubbala, and Karina Mangu-Ward’s pages).

I’m excited to be at August because I’m convinced that how we work, what we believe, and what we help our clients to develop is the future — and coming your way sooner than you probably think. We’re creating the future of work, and it’s a heck of a rollercoaster getting there. If you’re down for the ride, feeling inspired by the thought of making work suck less, and energized by the change we are trying to be — join us (if you haven’t already!) Sign up for our newsletter, read our writing, and most importantly, try out some of the practices and structures we use. Because I, we and you certainly can’t do this alone — we’re creating a movement here, and it’s only going to work if we ride the coaster together.

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