What it's like to be an IC at Stripe 💳 (Startup Watching #250)

By Andrew Askins • Issue #250 • View online

Happy Thursday Watchers!

In talking with my therapist I realized one of the things I’ve been struggling with at work is identifying my role and adapting for different situations.

I often joke my job is to do whatever no one else wants to do. But as a founder at a small company, you’re always filling lots of roles.

Sometimes I get stuck wearing the wrong hat for a given situation. In a brainstorming meeting for instance, my get shit done hat is not nearly as useful as my creative thinking hat. In meetings with team members, I often get stuck in problem solver mode when I should be coaching and guiding.

If you’re in the same spot, how do you get unstuck?

First, take stock of all the roles you’re filling. Then, be mindful of what role is needed at a given time. Schedule transition time before meetings or in between tasks. Long term pay attention to the roles where you are at your best and/or your most fulfilled. Work yourself out of everything else.

To start, I’m using an exercise a friend recommended.

My partner and I spent an hour today creating an org chart for the future. We mapped out what our company would look like if we had 30 people (our goal for growth). What jobs would we have?

If you want to see what it looks like there’s a screenshot at the bottom of the email. It’s not perfect and I’m sure it will change as we get closer to that goal. But it’s helping me to picture the different roles I’m filling now, and how I should approach situations differently depending on the hat I’m wearing.

Cheers from Charleston ✌️

Andrew

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FEATURED

What working at Stripe is like 💳

I recently found myself wondering why Patio11 works for Stripe instead of running his own business these days. Turns out he wrote about. The post is a neat look into life at Stripe, how a brilliant blogger thinks about his role in life, and what it means to be an Individual Contributor at a large company.

www.kalzumeus.com • Share

WORK

The remote work setup of an engineering manager 👨‍💻

You know you love checking out someone else’s remote work setup. It’s always fun to dream about upgrading your gear if budget was no concern. Anjuan Simmons has an impressive setup, and broke it down in detail here.

anjuansimmons.com • Share

6 lessons from 6 years of freelancing 🤺

I dug these lessons from Kat Boogaard, especially the talk about setting boundaries. It’s easier said than done, but so important when working with clients.

katboogaard.com • Share

FUN

Beach Read by Emily Henry 🏖

I love Rom Coms. Always have. Love to watch them or read them. I really loved this one by Emily Henry about two rival authors who end up spending a summer living next door to each other and competing to write a better book. One of the reviews thinks they tried a bit too hard, “I think there was too much emotional depth and not enough fluffy romance??” 😂 But I thought it was just the right amount of emotional depth.

www.amazon.com • Share

Our rough attempt at an org chart if Krit had 30ish people

BONUS

Since we talked about Stripe up above, this thread was a good dive into why you shouldn’t just rip off Stripe’s new homepage design.

Corey Haines 💡

@coreyhainesco

Stripe published its new homepage.

SO BEFORE YOU COPY IT

...you might as well know what you're getting into? 😉

Here's why it's a great example in some ways, but ultimately a bad example in others because they can use their brand and renown like no one else can 👇 https://t.co/a2xSYDxtWu

2:16 PM - 7 Jul 2020

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By Andrew Askins

Curated knowledge, inspiration and background stories from the startup world. Delivered to your inbox every Thursday or Friday 📬 | Find me @andrewaskins.

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What it's like to be an IC at Stripe 💳 (Startup Watching #250)

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