Issue No. 23: Bankruptcy?

“But I needed to have both low risk and high returns, and by setting out on a mission to discover how I could, I learned to go slowly when faced with the choice between two things that you need that are seemingly at odds. That way you can figure out how to have as much of both as possible. There is almost always a good path that you just haven’t discovered yet, so look for it until you find it rather than settle for the choice that is apparent to you.”

- Ray Dalio, Principles

I was first introduced to the idea of declaring non-financial bankruptcy by a former co-worker named Matt. I didn’t know him all that well, but we were on an intense project together, he was full of energy and seemed pretty organized. But then one day he declared that he was claiming email bankruptcy. He was so behind, the number of unread messages so daunting, that he felt he would never catch up. 

According to Wikipedia, “Email bankruptcy is deleting or ignoring all emails older than a certain date, due to an overwhelming volume of messages.” At the time, even now, this was a radical idea to me as I’m meticulous about email in that I will never  just not respond. Adam Grant nicely sums up my approach in his NYT column: “Responding in a timely manner shows that you are conscientious — organized, dependable and hardworking.”

But lately, I’ve found myself returning to this idea of declaring “Enough!” and starting fresh. I’ve been playing around — just in my head and now here — with other applications for this “bankruptcy” beyond email:

  1. Could I declare to-do list bankruptcy and start from scratch based on what really matters to me today?

  2. Could I delete the pages and pages of unread articles on my Instapaper reading list, the oldest dating back to three years ago, many of which are no longer relevant or of interest?

  3. Could I hit “Trash” on the Excel spreadsheet that I use to track the books I think would be a good idea to read but — let’s be honest — will never get to?

  4. Could I scrap all the plans I have for what I could do with my business — documented in Google Docs, Milanote boards, and Asana — and build from a blank slate?

  5. Could I wipe clean where I think I should be in life and simply embrace where I am?

When I’m overwhelmed, I’ve always found it incredibly helpful to take a beat and get clear (or as clear as possible): What am I working with? What really matters? Where am I trying to get to? What do I need to do? What do I want to do? And if declaring some sort of bankruptcy, essentially bulk editing things out of your life, provides that much-needed clarity, why the hell not?

  1. If every time you look at your calendar you want to cry, how would you feel if you could really, truly start from scratch — if not for your whole calendar at least some core piece of it?

  2. If you’re struggling to keep up with your marketing and content strategy, how would you feel if you nixed it all and re-built based on what you can reasonably achieve and do well?

  3. If your career just isn’t working for you, even after investing years in it, how would it feel to walk away and do something completely new?

  4. If your Instagram feed is so crowded with stuff you don’t want to see, or that drains you, how would it feel to carefully curate who you follow from zero up?

We do this in relationships — any breakup or divorce is essentially relationship bankruptcy. Although there is beauty and power in commitment, there is also power and freedom in knowing when to walk away, in knowing that something isn’t working, and recognizing it may never work — whether your inbox, your calendar, your “to read” list, etc.

If you could start over, what would you do differently? (Really, I’d love to know.)

It’s all an adventure,



  1. Feeling very adult with my Floyd Bed, the first real bed frame I’ve had since college.

  2. Realizing what I’m missing with my Seattle yoga situation after just one of Tiffany Russo’s classes in Los Angeles. She’s an amazing teacher, her classes so smart, so challenging, and just so good.

  3. Getting my summer dinner party game in full swing and turning to “9 Reasons to Host a Dinner Party” for some motivation.

  4. Oohing and aahing over Pantone’s Color of the Year, Living Coral, a “life-affirming coral hue.” (Funny story, it was also one of my wedding colors — 8 years ago!) I realize I’m way late to this color party … or maybe way early?

  5. Supporting Miir (Seattle-based, social-impact minded) and its Pourigami Kickstarter campaign. A pour-over coffee device that folds flat? Of courseI signed up.

  6. Turning to Wild at Home to get in touch with my elusive green thumb.

  7. Restocking my underwear drawer with refreshingly simple, no frills, yet luxurious goods from Negative Underwear.

  8. Wondering why we hear so little about most of the items on this list of 100 solutions to reverse climate change.

  9. Getting my fiction fix with Sally Rooney’s near-perfect yet heartbreaking Normal People.