There are so many reasons not to do a thing. Fear, laziness, lack of skill or resources, and stubbornness all come to mind. But this year, I found a reason more dangerous than all of them, worse because its lackluster sound gives it the camouflage of dullness among a deluge of new shiny things.

The danger is in finding a great idea, but thinking it doesn’t matter and tossing it aside. “No, obviously we won’t do that,” is the catch phrase. Spoken with enough confidence, especially by someone powerful and respected who uses logic well, and that idea enters the Land of Never Was.

The Land of Never Was is the place where discarded ideas go to hang out. It’s the bottom of the backlog, the coldest corner of the icebox, the bottom right hand corner of the kanban board. It’s a mostly dull gray place; dusty, creased, redolent with the smell of crumpled and slowly disintegrating notebook pages and post-it notes that long ago lost their stick.

Around this time of year I like to take a vacation there, and walk along the shore of the Sea of Could Have Been with my little metal detector skimming the dunes for something shiny that I might have missed. Whenever I do this I keep my expectations low, so I’m not necessarily expecting to unearth any treasures, but it gives me an excuse to stare out at the horizon.

I’ve been working on my startup for nearly 5 years, and on startups overall for 10 years, so the sea has had a lot of time to break down and turn over the remnants. You’d think after all that time, walking the same stretch of beach, I’d find fewer and fewer items of interest, but it isn’t so. I keep finding new ways to circle back on old ideas, as my little detector beeps and I dig up some shiny scrap that I didn’t notice last time I wandered here.

“No, obviously we won’t do that.”

Self-help books are abuzz with find the life-changing magic of tidying up, saying ‘no’ more often, giving fewer fucks, and startup culture rewards being stubborn in a “Jobsian” ideal of the creative genius persona. For those of us who already drank all this Kool Aid and are tough stubborn self-directed intensely independent motherfuckers, I have a suggestion: take a walk on the shore of your own imagination, along your Sea of Could Have Been.

Find something you said “No” to that should have been a yes, and make it right.

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It took us awhile to find this particular treasure, but we’re so happy that Mattermark now offers the ability to look up contact email addresses!

Also posted on Medium

“Am I doing a good job?”

“Am I doing everything I should be doing?”

I ask my cofounders these questions from time to time.They say yes and give me a hug, and my ego is placated. But later on I still wonder am I really doing a good job? Am I leveraging every moment of time the way I should?

There are a lot of articles telling us what we should do to be good, often formulated to demonstrate how to be more like whoever the hero CEO is.Wake up early. Time block your calendar. Raise now. Get that big valuation so it will be easier to recruit. Everywhere I turn on Medium someone has advice for what I should do, and I tell myself to listen because I want to be open to feedback and I want to learn. But sometimes when I am able to quiet that story down, I catch myself listening because it is just so much easier to have someone else figure out what I should do.

“I’m tired. Could you bargain with fate for me please? Thanks.”

As we head into a more difficult funding climate, I expect there will be a lot of founders saying, â€œbut I did everything I should have done… why can’t I raise a round? It’s unfair.” Where did that should came from? How can you justify your sense of justice getting riled up with “it’s unfair” when you didn’t even do the dirty work of picking the should yourself?

Shortcuts I Took

Sometimes I needed an answer right now, and seemed like a good idea to short-circuit the hard work of sitting still and figuring out what actually works with the most recent piece of startup productivity porn. It was a quick way to alleviate my angst, it was a self-centered solution that was more about resolving my own cognitive dissonance than getting it right.

In a hurry I’d implement someone else’s should unexamined, but all borrowing shoulds second-hand got me was second rate results. The worst part was that among the ideas thrown at me, I didn’t consider most of the really crazy ones… I stuck with the plausible shit, without considering the source. Re-arranging my calendar when I could have hired 20 sales reps.Might as well be re-arranging the fucking deck chairs on the Titanic.

So about half-way into the year I said fuck it. FUCK. IT. I’m gonna do crazy shit. I’m sick of being plausible and how the hell did I get this way anyway.Real self over in the corner flagged down ideal self and said, â€œhey remember me, I’m the college dropout who took a ton of personal and professional risk to have the life we always wanted? Frankly, you’re letting me down lately.”

Waking Up

It’s harder to explain this part, and I suppose this is normally where you’d find a step-by-step walkthrough of what I did to change my approach. It would actually be a list of shoulds for you, but thinly veiled as my own story.

I sat still. I let my inner voice be louder and more trusted than the outside voices. I hung out with myself, wrote and read and drank wine and lit candles and looked at the view and stayed still thinking and stayed in as friends joked I was “getting old” and I didn’t care anymore because fuck you I’m 30. I didn’t assume the answers were anywhere else. I read my old diaries and imagined I was 15. I read books I loved in school and imagined I was 9. I remembered my life so far, and I wrote down things I’ve already learned from it and I didn’t publish them for anyone else to read. I made things just for me, like paintings and really good food.

None of these activities would necessarily have meaning for another person but I knew they were what I needed. I remembered myself, I apologized to myself, I forgave myself, and gave her permission to let go of should.

I bowed.

Bowing In

Writing this down this morning, I remembered at Founder Bootcamp they would bring us all back together with the pretty sound of the Buddhist singing bowl. Jerry invited us to bow in, and I remember the first time we did I looked around the circle like, â€œOh geez, what crazy hippy shit did I sign us up for?” But I did it anyway and got past the awkwardness, and as we did it over and over again for days it started to take on more meaning, and naturally I got curious about this ritual. There is a great essay from Sojun Mel Weitsman at the Berkeley Zen Center that does a good job explaining it. I pulled the relevant quote but if you have time I highly recommend reading the whole thing:

How do you bow to yourself? You can’t see your own eyes, you can’t see your own nose, we don’t see our own face. It’s pretty hard to bow in this direction [toward ourselves], we’re always bowing in that direction [away from ourselves]. If you bow in that direction, you meet yourself. So who is this self? That question begs the other. If I bow to myself, then who is this “myself” that I’m bowing to? Therein is the fundamental koan, who is myself, and how do I bow to myself?

You don’t have to be a Buddhist to appreciate this idea of bowing as a ritual, both to yourself for introspection and also as an offering to others. It’s just a simple acknowledgement. Actually, I’m learning you can bow to anything.

I wasn’t planning to put this essay into this post, it just kind of came to mind as I was writing and now I’ve re-read it and there is another part that is also very relevant to “the tyranny of should”:

If you think about all the things that you promised yourself you would do and didn’t do, and look back on that, you’d be amazed at all the intentions you had that you didn’t honor. Sometimes this holds us back. So that’s why we have such a thing as the Bodhisattva Ceremony. We avow all of our ancient karma and unrealized intentions, and renew and honor our intention to continue. This is one of the most important factors of practice, that you have an intention, and honor it. Everything else flows from there. Enlightenment, peace, it’s all there in our intention. We also fall off, but when we fall off, we come back. As a matter-of-fact, we’re always getting sidetracked. That’s the nature of our life: to have this intention, get sidetracked, and come back. One of the obstacles is, “Now that I’ve fallen off, I can’t come back.” Or, “I’ve been bad.” So the nature of practice is to make the effort, that no matter what happens, to keep renewing or returning to our intention.

With these thoughts, I’m bowing in to 2016 and renewing my intention.

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“Wait, I just read this entire post and you still haven’t come to the point… Intention to what? What are you going to do?” you ask. â€œWhat should I do?”

I don’t have an answer for you, I can only smile.