Story

My Typical Week as a Founder

Apr 14, 2017

Most of this journal’s posts were written as the result of a random thought that was worth writing about. I’d like to continue this, but also focus on what others are curious about. One of the most common questions I get is what my day-to-day looks like running Cushion. Since I wear many hats as the founder, designer, developer, support person, and now manager, I try to fill a lot into the week. Writing this down will be a good exercise for me as well to recognize any areas where I can improve.

Monday

I’ve come to accept that Mondays are meant for catching up. If I go into a Monday thinking I’ll be productive from a design or development sense, I’m always left disappointed, feeling like I didn’t accomplish anything that day. If I could only convince myself to count emails responded to, planning for the week, and coordinating with others, I’d feel much better at the end of the day.

Intercom

Most mornings, I wake up between 7:30 and 8am, make coffee, and sit on the couch with my cat while catching up on email, support, or even working on an idea I let marinate the night before. Around 10 or 11am, which is when my wife wakes up (she’s a night owl), I’ll start to get ready to leave for the studio. I’ve come to realize that my less stressful days are when I take the morning slow and get ready with my wife rather than rushing to the studio before she’s awake.

Craft

Depending on the week, I’ll either work with Carly Ayres on a Talking Shop interview, Andy J. Miller on a Ask a Freelancer podcast episode, or I’ll write in this journal. Each of these are on 3-week intervals, with exception for the journal, which I’m trying to keep to at least once a week.

Talking Shop

For Talking Shop, Carly has already interviewed the guest, transcribed and edited the interview, and coordinated with Ping Zhu on the illustration. Once everything is ready, I’ll add it to the website and queue a tweet for the next day.

Ask a Freelancer

For Ask a Freelancer, we have a TypeForm survey that funnels questions into a Google spreadsheet that Andy can pick from. In the afternoon, he sends me draft audio and a sketch for the illustration to approve. I listen to the episode and we text back-and-forth about the sketch until Andy‘s ready to take it to final. Once I receive the audio and illustration, I’ll upload the audio to Soundcloud, which feeds the episode to our iTunes podcast. Then, I’ll add the illustration and Soundcloud embed to the website.

Clearly, the work involved with me adding Talking Shop posts and Ask a Freelance episodes to the website could be done by an assistant or content person, but we’re not there yet. Until then, more work for me!

Tuesday - Thursday

TeuxDeux

I try keep a fluid schedule rather than sticking to an exact routine, in case one area of Cushion needs more attention than another. It’s also easier to handle a lost afternoon because of a meeting, which can kill my productivity and throw off my entire day (I’m not a fan of meetings). I don’t use a traditional calendar, but instead keep a reflowing list of to-dos and scheduled events in my TeuxDeux.

Studio

Our studio is within walking distance of my apartment, so I’m able to avoid the subway commute completely and enjoy a nice walk. Along the way, I think about what I need to do that day, so I’m ready to hit the ground running as soon as I get into the studio. Larry, our backend dev, usually gets in earlier than me. On most days, we code independently until noon, then walk somewhere for lunch. Getting out of the studio for lunch and eating together is really important to me. It’s especially valuable for when one of us is stuck on a problem or decision. After talking about it over lunch, we usually return the studio with a solution.

Coffee Time

I typically get my best dev work done after lunch, which allows for a solid hour of uninterrupted time. Around 2:30pm, I make coffee for the studio and we talk about random, non-work things. Since we work out of a co-working space, it’s a good time to catch up with everyone else outside of Cushion.

From 3 to 5pm, I get a second wave of solid dev time. I try to keep any design work for moments when I’m taking it easy. It’s easier for me to iterate on a few ideas outside of vital 9-5 work time. Depending on whether my wife is working late at the studio or not, I’ll either work late, too, and eat at the studio, or we’ll walk home together and continue working on the couch.

When I’m home, I try not to work as much, or at the very least, only work on aspects of Cushion that aren’t too important. Sometimes this means one-liner bug fixes or book-length support tickets that I needed more time to answer. I also save any work on the marketing website for after-hours, so I can save the main workday for the app.

Cooking

Lately, I’ve been learning to cook more, which really helps me get away from the computer for an extended period of time and not think about work. I also feel better at the end of the day when I’ve “worked” with my hands and ate food from our own kitchen, instead of taking the lazy route by ordering delivery. Some days, however, all we want is food from our favorite Thai restaurant.

Friday

I’ve learned that it’s best to only work on low-hanging fruit on Fridays. This could mean bug fixes, small features, or any non-app work. Taking care of simple tasks makes it so much easier to call it day at a reasonable hour end get closure on the week. When I work on a feature that hooks me into multiple days, I’m always left thinking about it the rest of the day, completely distracted when we’re trying to relax. Big features also lead into working the weekend, which is common, but designated more for cleanup work.

Friday

Around 4 or 5pm on Friday, everyone in the studio starts to call it quits and hang out at the space. Most Fridays, I’ll end up walking to Fictive Kin’s studio for “Pizza Friday”, where we catch up over pizza and drinks. This time is especially precious for me because I get to see a few friends who used to work in our space. We’re also able to completely relax knowing that the week is over.

Saturday - Sunday

While I know I shouldn’t work on the weekend, I always end up spending time on a few ideas I wanted to dive deeper into or maintenance work I didn’t want to waste weekday time on. Some of my better weekends are spent walking around Brooklyn with my wife or playing basketball with a group of friends at our local courts. Since my wife freelances, we usually end up at the studio at some point, but it’s much more laid back. On Sunday, I’ll start to prepare for the week ahead, clear my inbox, and cross off any to-dos that were left. If I have an idea for a journal post, I’ll designate time for writing. Then, repeat.


Photography by Sara Kerens

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Archive

  1. Restructuring an Evolving App: Part 1
    Design
  2. My Typical Week as a Founder
    Story
  3. Building Components in a Sandbox
    Dev
  4. Reactive Time with Vue.js
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  5. Visualizing Daylight Saving Time
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  6. Recording Screencast GIFs
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  7. Writing a Job Listing
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  8. Using Feature Flags to Run Betas
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  9. Our First Company Lunch
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  10. How to embed Vue.js & Vuex inside an AngularJS app... wait what?
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  11. Funding Cushion
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  12. Hiring a Team of Freelancers
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  13. Taking a Real Break From Work
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  14. Slack as a Notification Center
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  15. Document Your Features
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  16. 300
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  17. Vacations
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  18. Offering Discounts
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  19. Waves of Traffic
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  20. Less Blogging, More Journaling
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  21. Retention Through Useful Features
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  22. The Onboarding Checklist
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  23. Spreading the Word
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  24. From Beta to Launch - The Subdomain
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  25. From Beta to Launch - Sign up
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  26. From Beta to Launch - Messaging
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  27. Launch
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  28. Authenticating with 3rd Party Services
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  29. Intro to Integrations
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  30. Inspiration vs Imitation
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  31. The Emotional Rollercoaster
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  32. Designing Project Blocks
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  33. Everything in Increments
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  34. Deleting Your Account
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  35. Designing the Subscription Page
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  36. Rewriting the Timeline
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  37. Restructuring the Individual Project Page
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  38. Project Blocks
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  39. Redesigning the Homepage
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  40. Multiple Timelines
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  41. Archiving and Estimate Differences
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  42. Multiple Financial Goals
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  43. Zooming in on the Timeline
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  44. Currency
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  45. Preferences, Accounts, and a Typeface Change
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  46. Sending Out the First Email
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  47. Currency Inputs, Notifications, and Invoice Nets
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  48. Dots and Lines
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  49. Calculating in the Database and Revealing Tendencies
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  50. Improved Form UX
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  51. Cushion is Online
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  52. Schedule Timeline Patterns
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  53. A Slimmer Schedule Timeline
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  54. The Schedule Timeline
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  55. Plugging in Real Data for the First Time
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  56. Transitions and Project Lists
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  57. Death to Modals
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  58. The Individual Project Page
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  59. Estimated Incomes and Talks with Other Freelancers
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  60. Statuses to Lists and the Paid Beta
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  61. The Timeline
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  62. Invoice Terminology
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  63. Modal Forms
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  64. Wiring the Backend to the Frontend
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  65. Balancing Design and Dev
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  66. Timecop, Monocle, and Vagrant
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  67. Going with Ruby and Sinatra
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  68. Ditching local-first and trying out Node.js
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  69. Switching to AngularJS
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  70. Building the Table with Vue.js
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  71. Clients, Projects, and Invoices
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  72. Introduction
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