8 things a founder does that don’t feel like “work” — but are

Sally Simms
3 min readOct 4, 2018

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One of the best and hardest things about entrepreneurship is realizing workdays that don’t look like “work” are often the most generative. Here are some things I do as a founder that I used to think weren’t “real work”. Turns out they are.

  1. Talk to people I just feel like talking to (over coffee, or whatever!). → Turns out this is actually getting well-curated context and advice from experts. People I’m interested in talking to usually end up having something to offer to the business. Intuitively, that’s why I’m curious about them.
  2. Read stuff on the internet that seems interesting. → Turns out this is absorbing a ton of relevant information that informs my understanding of How Things Work and helps me contextualize and design my business model and product, and understand my market. Domain expertise and novel insights that shape a business don’t come from nowhere — they come from interest.
  3. Read definitely irrelevant stuff for fun. → Oops! Turns out it applies to the work. I read a lot of fiction and unrelated nonfiction, and I end up using it in my work at least weekly. Making connections between currently un-linked things is what new companies do. And founders define their companies out of themselves at the start, so if you want to be generative, you need diverse intakes. Your interests are valid.
  4. Explore the same stuff I already know about my company a million different ways, a million different times. → Turns out it is my job as a founder to understand the big picture — dynamically, as it evolves — and translate it, and get it to connect with everyone who needs to understand it at each stage. That means I have to read a lot, talk to a lot of people, and constantly evolve my own image of my company and product. I say the same thing a thousand ways, and I’m always learning about my own company as I do it.
  5. Take advantage of my early-stage, solo-founder flexible schedule to exercise, take my time getting around, shop for groceries during the workday, etc. → Turns out every single time I do this, I end up clearing the fog in my brain and realizing new insights or steps forward for the company. I consistently write my best thoughts and plans on subway trains, treadmills, and while waiting in lines, while I’m “not working hard”. When you have the big, broad job of founder, sometimes you need big, broad expansive, undirected thinking time. Sometimes you need a big monitor and total focus, but a lot less often than you probably think. Too much of that, as it turns out, is just myopia.
  6. Spend time with my friends and family, not working at all. → Turns out spending quality time with people you love makes you a more confident, wise, and balanced person — especially when working really hard takes a lot out of you. When you’re a founder, you can never totally part yourself from the work — so you have to learn how your personal life helps the work.
  7. Pay people to do things you don’t feel like doing yourself. → Turns out this isn’t laziness… it’s hiring a team. Something all successful, growing companies do.
  8. Commiserate with/get inspired by other founders. → Turns out communities of founders have a ton in common, and everyone is learning a lot, really fast, and needs a lot of help constantly. That means you’ll end up realizing some of the great things you’ve already figured out, when other founders ask you for help. And you’ll end up having just the right person to help you, when you’re in need. Hanging around talking about how you both can’t figure out Quickbooks might actually be, in the end, really good for your business.

What work do you do that doesn’t feel like “work” but actually is? Respond down below this post, or tweet at me. See number 8 — I want to hear from you!

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Sally Simms

Founder of Group Project, Brooklynite from Virginia, ex-VP Product + Ops at Buster, ex-Googler, always experimenter / groupproject.co / sallysimms.com