The Willingness to Throw it Out

A lot of my work days are about efficiency.

Tearing through my Inbox.

Having as few meetings as possible and making them as short as they need to be.

An overall feeling and attitude of moving fast and keeping an eye on the clock.

I’ve been in an overdrive version of this mode for the past few months, with an intensive focus on external sales and fundraising.

Then the other day, working on an important document, I had what I thought was a brilliant idea.

I started on it, made a terrible first draft, played around with the document, trying to make it resemble the original bolt of inspiration.

And then I had a paralyzing thought, “What if this is a waste of time? What if I work on this for the full two hours, give it my best shot, and then discover that it’s no good?”

And, if that’s a possibility, should I stop before I start—would that be the efficient thing to do?

Of course it would, and it would be a terrible idea.

The only way to create something truly worthwhile, something that only you can create, is if you walk along the This Might Not Work edge.

That means that you are actively aware that what you’re doing might not be good enough, that you’re dancing with that fear. You’re aware that even if it doesn’t work this time, the only way, in the long run, that you produce anything worth anything is if you consistently spend time doing things that might not work.

Which means that the point of all that efficiency is to create space that plays by a different set of rules.

It’s a space where you get to dance and make a fool of yourself and try daring things, many of which may end up in the trash, so that some of them can be amazing.

Looking When You Know It’s There

Entrepreneurs are famous for seeing the things others cannot. They believe in a truth that seems like fiction to everyone else.

For example, AirBnb founders Brian Chesky and Joe Gebbia failed to raise any outside money from late 2007 until early 2009. Maybe it makes sense: a business where strangers stay in each other’s homes doesn’t seem like a winner. In fact, they famously had to sell Obama O’s and Cap’n McCains Cereal to fund their startup, raising $30,000 in the process.

The big challenge, when we are attempting something new and difficult, is to know what to do with outside feedback:

Does what I’m hearing tell me a fundamental truth about the validity of my idea?

OR

Do I have so much conviction in my idea that I’m sure it’s right, despite not having found a customer for what I’m selling…yet.

Our level of conviction determines how we interpret outside feedback.

For example, consider the widespread phenomenon of “kitchen blindness:” the inability to find an item of food that is sitting right in front of you – milk, OJ, the salt or, famously, butter.

While “kitchen blindness” is often be the byproduct of laziness, it’s also true that there are two ways that we look for things:

  1. When we look without prior knowledge, we use the data that’s coming in (“I’m not finding the baking soda where it’s supposed to be”) as information to confirm or refute our hypothesis that we have baking soda.
  2. Whereas if we are sure we bought baking soda, and we simply are not finding it in the freezer, we take that to mean that we’ve got to look in the pantry, in the shopping bags, and in the trunk of the car.

One of the hardest lines to walk as an entrepreneur or creator is the daily choice between using outside feedback to adjust / refute our hypothesis vs. sticking to our guns. (for more on learning when to quit, there’s no better book than The Dip by Seth Godin.)

Are they telling me something true that they know and I need to learn?

Or is this my “naysayers be damned” moment, and do I believe, like Steve Jobs did in 2007, that I can design and sell a smartphone that doesn’t have a keypad?

Deep down, it’s a question of conviction:

How sure am I that what I’m looking for is there?

Because if I’m really, really sure, then it really is there, and all I have to do is find it.

 

 

 

 

Goodbye Notebook, Hello Notion

For years I carried around a nice, small Moleskin notebook to every meeting. I had various systems, each typically lasting about a year, to distinguish between note-taking content and next steps.

Moleskin Notebook
Photo by Stationary Nerd

My notebook was a sacred object which, if lost, set my productivity back by weeks or more. That said, the constant iterating on how to manage the space and my to do list, the inability to search for anything, and my crummy handwriting combined for a system that I knew needed improvement.

This last year, when Zoom meetings started, I stopped using my notebook almost immediately.

This wasn’t a conscious choice: it had more to do with the physical setup of my desk and where I was sitting around my house. For a while I wasn’t taking notes, and I used other systems to track to do’s. It felt like things were working well enough, though I was nervous about what was falling through the cracks.

Then, in March when I really ramped up my external sales and fundraising, I started taking notes in Notion.

Notion is a very powerful tool, and I use about 1% of its functionality (probably less). For me, it’s just Google Docs on steroids, but it’s so fabulous at what I’m using it for that I would miss it terribly if I couldn’t use it.

I like it much much more than Google Docs because:

  1. The interface is slicker, particularly the keystrokes (e.g. I type ‘/to do’ and a to do list appears; I type a dash and hit ‘tab’ and I’m making a bulleted list).
  2. I find file storage in Google Docs disorienting: it always feels like a jumble of searchable docs, instead of “here’s everything all in one place.” With Notion, I click on one URL and all my meeting notes are there, easily organized, and well-structured.
  3. Google tracking all my keystrokes and suggesting what I type next wigs me out.

I create one Notion page per meeting, with clear follow-ups, organized in a super-simple week-to-week structure. It looks like this.

Notion Sales Meeting Notes

This has transformed my work in two ways.

The more obvious point is that it’s so clean and organized. Everything is in one place, I know exactly where to find it, and the to-do’s are so black and white (and so fun to check off) that it makes staying on top of everything a breeze. Plus, because of the simple interface, I find myself using it consistently. At the end of a day with 8+ external meetings, I cannot remember what I promised anyone in the first half of the day…thankfully it’s all there in Notion.

The more subtle point is that taking notes during a meeting keeps me more focused. I listen harder and stay fully dialed in, something that can be difficult with hours of external calls every day.

I like this approach so much that I wonder what I’m going to do when in-person meetings come back, since I don’t think banging away on my keyboard with someone right in front of me is going to work.

Until then, I’m totally devoted to Notion, and I think you might like it too.

 

 

 

Getting Into Position

I play a lot of racquet sports, more so in the last year thanks to COVID-19. Not just squash, which was off limits for about 6 months, but tennis, platform tennis and, most recently, pickleball (which is becoming hugely popular because it’s so easy to learn).

In my forever quest for improvement, I pay a lot of attention to my technique. I even got an inexpensive tripod recently and took some videos of my squash matches…and quickly had an existential crisis when I saw that my strokes don’t look like the pros’. So I fussed a bunch over my backswing, my follow-through, the position of my racquet.

Then I discovered that all those things I’d been worrying about pale in comparison to how I move around the court: when I consistently focus on  just one thing – getting to the right spot with enough time to hit the ball – I play my best squash.

It’s not surprising. After 25 years of playing, I know the strokes well enough. I just need to put myself in a position to consistently do what I know how to do.

In the rest of our lives, “in position” isn’t about footwork, but the same principle applies about setting ourselves up to do our best work.

We do this by being grounded, calm, and focused on the person in front of us.

By centering ourselves with an intention of connection and generosity.

By taking a moment before we start to remind ourselves what we’re passionate about.

By letting go of the voices in our heads shouting about our impending failure before we’ve even begun.

And by, each day, allowing ourselves to be well-rested and centered, by taking care of our physical and emotional well-being outside of work so we can be our best selves at work and at home.

Sure, our skills can improve.

But most of the time what will help the most is setting ourselves up, consistently, to do the great work we already know how to do.

At our best, we are truly phenomenal.

The Zoom bcc

Remember how email introductions used to work?

You would introduce two people by email, and then find yourself on a 20-message back-and-forth as they worked to schedule their meeting. Then we all collectively learned how to do this: you have introduced Janet to Kareem, and Janet replies, “Thanks so much for the introduction Sasha. Moving you to bcc:”

Janet and Kareem can then get on with their (hopefully useful to both of them) conversation.

Two things are going on here:

  1. There is standard, expected language for how to handle this sort of introduction.
  2. It is culturally acceptable to bcc: someone in this situation, a shift from “is it rude to drop this person from the thread?” to “it would be rude to include this person on all the follow-up emails.”

While Zoom has been a lifesaver during this pandemic, we’re still in the early days of learning how to navigate it: sound, connectivity, breakout groups, who speaks when and how, backgrounds, etc…

Our Zoom cultural norms are in their infancy.

I propose we create the Zoom bcc.

It’s for situations in which it’s clear that a meeting has too many people. Two or three people are having the entire conversation, and everyone else is just listening in.

Right now, no one knows how to handle this.

The people listening in end up choosing between:

  1. Staying focused and really listening (rare); or
  2. Doing some other simultaneous activity while pretending to be present in the meeting.

These are both bad options. Most people struggle to stay focused in an hour-long Zoom meeting if they don’t need to be there. They end up multi-tasking, an ineffective use of their time and a distraction to everyone else.

Instead, it could become culturally acceptable to drop a short note into the chat that reads,

“Glad you guys are having a great conversation. I’m looking forward to hearing the update, and I’m going to drop off now.”

The people who need to talk get to talk, the people who are less active have a choice about how to manage the situation: stay, and be fully present; or leave in a way that is understood to be both appropriate and professional.

Everybody wins.

The Confidence to Cut

Jerry Seinfeld described the two personas we need to inhabit to be good writers.

The key to writing, to being a good writer, is to treat yourself like a baby, [to be] nurturing and loving, and then switch over to Lou Gossett in Officer and a Gentleman. and just be a harsh [expletive], a ball-busting son of a…When you’re writing, you want to treat your brain like a toddler. It’s just all nurturing and loving and supportiveness. And then when you look at it the next day, you want to be just a hard-ass. And you switch back and forth.

I love it: a gentle nurturer, treating my brain like a toddler, and then a hard-assed drill sergeant who is relentlessly reviewing, looking critically and, most important, cutting.

Most of the time, our writing has too many words. These extra words are a place to hide, an excuse for 80%-there thinking that’s directionally correct but still fuzzy.

The false safety of extra words and high-falutin language is how we avoid laying our ideas bare.

When we cut, our ideas stand naked and exposed to the world. They can be seen clearly, unadorned. The unadorned is bare, but it is also beautiful.

It’s an act of courage to cut away all the unnecessary bits, to stop burying our best thinking in extra blather.

We cut, we cut, we add a bit, and then we cut some more.

On and on until one of two things happens: either we learn that this idea isn’t good enough, or we discover the distilled essence of what we want to say.

Cutting is an act of confidence and bravery. When in doubt, cut.

AdAge is Wrong About The Lincoln Project

According to AdAge, the Lincoln Project, the anti-Trump PAC that ran ad after of scathing ad throughout 2020, was one of the best marketers of the year. In their words, “The conservative anti-Trump PAC made some of the most compelling and influential ads of the year.”

The purpose of the Lincoln Project was to get Republicans to defect from Trump. Disaffected Republicans created The Lincoln Project because they felt that Trump was destroying the country and the Republican Party. Their YouTube page has more than 350 videos, many viewed well over a million times, and they are some of the highest-quality political ads you’ll ever see.

The problem is, they weren’t influential.

In fact, 93% of registered Republicans voted for Trump in 2020, compared to 90% in 2016. Worse, according to a study by the Democratic super-PAC Priorities USA, the most popular ads had the least impact on voters in swing states,

The lesson is essential: we must always remember what marketing is.

Marketing is the act of persuading someone to take an action.

We consistently confuse who the “someone” is: it is not us, it is someone else.

The Lincoln Project convinced me of a lot of things; it also convinced Trump-haters of a lot of things. But I and they weren’t supposed to take a different action because of these ads.

As marketers, we struggle so much to create great content that, when we do, we’re quick to tell ourselves that we’ve done great work. And, we very well may have.

But our job as marketers isn’t to create great content. Our job is to persuade someone specific to take a particular action.

If you haven’t figured out who you’re trying to persuade, and if you haven’t figured out if they took the action, you’re not marketing. You’re just creating stuff and putting it out into the world.

Strategy and Conviction

Strategy is fundamentally about choices.

When we write down our (company, personal) strategy for the coming year, we are articulating the things we will prioritize differently, the things we will put more time and resources behind because we believe that doing so will lead to better results.

This means that all good strategy is about change. We implement our strategy by shifting from what we used to do—which was comfortable—to what we are going to do now—which is new, and therefore harder.

The bridge from here to there is conviction.

Conviction that the new path is right.

Conviction that we must give up some of the things that got us, even if that’s hard in the short term.

Conviction that even if we don’t see the yield of our new strategy immediately, we will give it time to play out before reverting to our old ways of doing things.

Conviction, of course, is itself a decision.

It’s a choice in the face of unknowns and uncertainties.

It’s a recognition that through the acts of believing and follow-through we shape reality, transforming something that could be into something that is.

Strategy without conviction is just words on a page.

 

My Call

The situation is messy, and it’s unclear who gets to decide.

I’m not sure that I know best – or even enough.

Nevertheless, I recognize that in this situation, a decision has to be made. So I’m using my judgment and I’m making the call. Because ultimately that’s my job: to make tough decisions and be responsible for the consequences.

The most important professional moments are defined by a willingness to step into uncertainty, to act, and hold oneself accountable for outcomes.

Not because we need more people to make good decisions. The answers themselves, whether right or wrong, are a dime a dozen.

What’s scarce is the willingness to take responsibility for success and for failure—to be on the hook for your customers and your team.

Privilege is

I’d written this blog post already, and then came across this TikTok from tWitch and Allison, which does a much better job at making my point on a visceral level.

If you didn’t click, here’s a paraphrase of what they’re counting down on their fingers. White Privilege is:

Never having been called a racial slur.

Never having been followed in a store unnecessarily.

Never having had people cross the street to avoid walking by you.

Never having had someone clench their purse in an elevator with you.

Never having had someone step off an elevator to avoid riding with you.

Never having been accused of not being able to afford something expensive.

Never having had fear in your heart when having been stopped by the police.

Never having been given a pass on a citation that you deserved.

Never having been stopped or detained by the police for no valid reason.

Never having been denied service solely because of the color of your skin.

Never having to teach your child how not to get killed by the police.

 

Here’s what I’d add to that list.

Privilege (white and otherwise) is also:

If you, or your kid, breaks something you love, you know you can get a new one.

If all your schools were always well-resourced, were not overcrowded, were filled with qualified teachers.

If you’ve ever had a private tutor of any sort.

Or private instrument lessons. Or private lessons of any kind.

If you expected, from the day you were born, that you would go to college.

If you’ve ever had an unpaid internship.

Or an informational interview with a powerful friend of your parents’ or their friends.

If you’ve never been truly afraid to walk down a dark street at night, or to your parked car in a garage, alone.

If you’ve rarely, if ever, been forced to be conscious on a daily basis of your race or another element of your identity—indeed, if you barely think about your race or other element of your identity if you don’t want to—because it almost never engenders an experience of outsider-ness or threat for you.

If you’ve never had to explain to someone else what it feels like to be a person like you—when “like you” is about a group you’re part of rather than “you” as an individual.

If, most of the time, especially in situations of consequence (classrooms, school and job interviews, sales meetings, industry conferences, fundraising pitches, board rooms), you are in groups made up of almost exclusively of people of the same race, gender, sexual orientation, and ethnicity as you.

If most of the people on TV shows, in ads, and in magazines look like you…

…and the same goes for the person who saves the day in nearly every movie.

If you don’t have a parent, uncle or aunt, grandparent or great-grandparent who was systematically persecuted, tortured or killed for some aspect of their identity.

And if you feel like you’ve had the choice of whether or not to pay attention, feel personally affected by, and act in response to the murders of George Floyd, Ahmaud Arbery, Michael Brown, Terence Crutcher, Eric Garner, Oscar Grant, Freddie Gray, Botham Jean, Atatiana Jefferson, Bettie Jones, Trayvon Martin, Oscar Grant, Laquan MacDonald, Tamir Rice, Breonna Taylor, and Dominique White.

 

What I appreciate at the end of the video of tWitch talking to Ellen is his saying that he and his wife, and he and his in-laws, are having much deeper conversations about race than they’ve ever had before.

And, as he rightly says, while it’s not enough, it’s a start.

Until white people fully see the privilege we have, until we can see what Peggy McIntosh called (in 1989!) our “invisible weightless knapsack of special provisions, maps, passports, codebooks, visas, clothes, tools and blank checks” then we are, honestly, in no position to contemplate the steps we need to take to be part of the solution.