I Get a Cookie

It turns out that Jerry Seinfeld has a 24 hour rule.

Whenever he writes any new material, his rule is not to show it to anyone for 24 hours.

The rationale is that writing is a brave, creative act. We humans need and deserve positive reinforcement every time we engage in that act of bravery.

Part of the way we preserve that is by shielding anything new we’ve created from others’ eyes. This allows us to experience the halo of “I did it” before experiencing the crush of “maybe it’s not any good.”

In fact, Jerry advises that when we do a brave act of creation, we should give ourselves a (metaphorical or actual) cookie.

Time and again, I find myself skipping this congratulatory step, the one in which I get to bask, for just a moment, in the knowledge that I was brave today, that I created something new.

Instead, I nearly always ship off that new thing to someone for their quick reaction and feedback (time’s a-wastin’). Or, just as bad, I finish my first draft, put down my pen, and notice how much time that took and all the other undone things on my to do list.

One solution that helps me is having time in my calendar for “brave work:” empty spaces that are only for creating new things. This way I know what that time is for, and I cannot beat myself up for other tasks that remain undone. This also helps me remember that brave acts of creation and efficient time management exist on different axes.

Finally, I remind myself of the advice of one of my favorite yoga teachers: we can leave our problems and our worries outside of the studio door, because we can be sure that they’ll be there waiting for us when our practice is done.

So, maybe it’s time to resolve that our best work should be free from prying, critical eyes for a day.

Without knowing there’s some psychic reward waiting for us on the other side, why will we ever dare to take the plunge?

The Paradox of Discipline, and Four Questions to Ask Ourselves

The more I listen to interviews with great creators, the more they echo the same themes. It goes something like this:

The act of creation is exceptionally hard and painful.

Writing, in particular, is torture.

It’s great to have talent, but without a disciplined process for creation, talent means nothing.

We human beings do everything we can to avoid the hard work of creating our art. To counteract this, we must create rituals and structures that make it impossible for us to hide: time every day in which the only thing we can do is produce. (For example, per Neil Gaiman, “I would go down to my lovely little gazebo at the bottom of the garden, sit down, and I’m absolutely allowed not to do anything. I’m allowed to sit at my desk, I’m allowed to stare out at the world, I’m allowed to do anything I like, as long as it isn’t anything. Not allowed to do a crossword, not allowed to read a book, not allowed to phone a friend, not allowed to make a clay model of something. All I’m allowed to do is absolutely nothing, or write.”)

We must be forgiving with ourselves when we are creating, and brutally tough on ourselves when we are editing and refining.

This isn’t going to be fun. But if we are to do our best work, if we are to give our gifts to the world, we have to be willing to grind out the effort each and every day, no matter how hard it feels and how little we feel like doing it on that particular day.

Now, I believe that these insights apply to everyone, not just to “creative” types. No one said that doing excellent, meaningful work was going to be easy, and I expect that writers and artists are just living the fully-distilled version of creating work that matters.

If these insights are to apply to all of us—and I believe they do—then we have four questions we need to answer honestly:

  1. Am I willing to care, at a personal level, about my work?
  2. Am I willing to take personal, emotional risk to put my best into my work?
  3. Will engaging in this kind of sustained, daily effort help me grow?
  4. Am I going to decide to learn how to put in sustained effort over time?

This framing feels fundamentally different from conversations about “work-life balance” and the perennial elevator small talk of “just three days until the weekend.”

In one view, work is something to be endured and minimized so we can refresh in our free time, and work being hard is an indication of something being wrong.

In another view, work being hard is the necessary precondition for it being meaningful, because there is nothing worth producing that doesn’t require risk and struggle.

While this doesn’t mean that all work we find hard is rewarding, it means that we cannot use “hard” as a barometer for something being wrong at work.

Somewhere, somehow, each of us has to find our own version of discipline.

For example, I don’t have access to Neil Gaiman’s gazebo, nor do I write fantastical fiction or comics. But both Neil and I need time alone, time to think, time with the proverbial blank page; time when we’re looking straight at a problem we don’t know the answer to; time when our job is to sit there until we produce one thing that is one small step in the right direction.

Discipline is often not fun. It is, at a minimum, the act of sitting with discomfort and delaying gratification because we know that this is what it feels like when we do real work.

Of course, most of us have not figured out what our art is, we don’t know what we are uniquely suited to do in the world.

That’s OK. We don’t need the full answer today. We need, instead, to decide to start doing meaningful, personal work as soon as possible.

And how do we start? Not with musing, reflection or pretending that if we wait long enough inspiration will touch us. That’s a great way of hiding.

Instead, we start with building a practice of creative discipline into our days, weeks and lives: we put ourselves in situations every day where we ask ourselves to make one small thing that we are proud of, one small thing that is over and above the exact thing we were asked to do.

With this mindset, our work becomes something we can take personally, and each thing we ship can be different and better for what we’ve put into it.

From the moment we decide to take our work personally, we start to show up like professionals, and, bit by bit, we watch the yield that comes from refusing to be swayed too quickly by the thoughts that all of us have: this is too hard; this might not be good enough; if I care a little less, then I won’t be hurt if I come up short.

Caring less and risking less are great ways to stay safe in the short term, and even better ways to ensure that we stay where we are in the long term.

Whereas if we shift our attitude towards our work and learn how to build discipline into our days, we set ourselves down the harder but much more rewarding path of sharing what only we have to offer through our work.

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.

Orwell on Un-slovenly Thoughts

In Politics and the English Language, written in 1946, George Orwell mused, “Most people who bother with the matter at all would admit that the English language is in a bad way.”  Imagine if Orwell had been able to see what unfolded over the next 70 years.

You may not consider yourself a ‘writer,’ and it’s possible that writing doesn’t feel integral to your work. Even so, consider this a nudge to invest in your writing—the yields are broader than you might imagine. Writing is not a narrow skill, like juggling or doing a cartwheel. It is a mirror into the mind: we cannot write clearly and persuasively if we are unable to think clearly and persuasively; and as we move the needle on our writing, we sharpen our powers of observation, analysis and storytelling.

Writing with the intention to change minds hones our abilities—to see what’s around us and develop insights about what we see, to understand the worldview of the people whose minds we aim to change, and to communicate in ways that shift thinking and actions.

Begin by choosing to write more. This is much more helpful than choosing to write well. Trying to write well is the best way to end up not writing a lot, and you cannot write well if you’re unwilling to write poorly. This means finding places to write: that could be investing in making your emails 50% better by making them shorter and more human; or you could sign up for a site like 750words.com, a private site where you commit to writing every day, just for you.

Imagine having this kind of transparency and accountability about your writing!

Then, stop writing the way we think we are “supposed to” write. It’s hard to pin down when, exactly, business-speak was created (though the Atlantic has a few theories), but the main function of so much passive tense and invented verbs (“downsize” “rationalize” “incentivize”) and catchphrases (“run up the flagpole”) is to obscure rather than to clarify, making your writing worse.

© Scott Adams

Your job isn’t to “increase the frequency of your articulation of stated arguments and objectives through engagement in writing- and writing-related activities,” your job is to “write more often and be more persuasive.” Please, please, write like you speak. We, your readers, want to read something written by another human being, and we experience human-ness when your voice comes across in the words you put down on paper.

To practice, before you hit the “publish” or “send” button, read what you’ve written, to yourself, out loud. Ask yourself: does this come out naturally? Is this how I speak? If not, cut, edit, and replace: remove words, replace words, say things in 5 words instead of 12. In the end, your writing will sound like your spoken voice: clear, simple, natural. Your goal is to express formed thoughts and emotions in as few and as precise words as possible.

Read more. Pick the kind of reading that speaks to you. The more you read the more good writing becomes part of your world. You may even inadvertently start mimicking authors you like, which is fine as a start: over time, your own voice will come out.

In the end, all of this is an investment not just in your writing but in your clarity of thought. It’s a chance to avoid the pessimistic concerns that Orwell describes as the self-reinforcing loop of poor language:

A man may take to drink because he feels himself to be a failure, and then fail all the more completely because he drinks. It is rather the same thing that is happening to the English language. It becomes ugly and inaccurate because our thoughts are foolish, but the slovenliness of our language makes it easier for us to have foolish thoughts.

As we give attention to our writing, we rescue ourselves from our own “foolish” thoughts. Over time, we clarify our own thinking, increase our capacity to persuade, and develop the skill of taking unstructured observations and turning them into clear, structured, persuasive words on the page.

Where do Blog Posts Come From?

I’m always curious how others come up with blog post, so I figured I’d share my approach after 11 years of blogging.

Being a writer of any sort means paying attention, and blogging has kept me on a constant, quiet lookout for moments of insight: a topic I find myself or my team struggling through, a conversation or article that touches on a bigger theme.

These sorts of moments happen unpredictably in all sorts of places. When they do, I jot them down. If I’m in front of my laptop, I’ll write a headline or a few sentences in Word. More likely, I use my phone to send myself a short email with the blog title in the subject line and a few notes. These emails are sketchy at best, and they’re occasionally frustratingly indecipherable. But they often are enough to go on as long as I get back to them quickly.

I go back to these sketches of ideas on the train to or from work. I dedicate 10-15 minutes to the first draft of each post. If things are going well, that’s enough time for a decent rough draft. Or, I discover that the idea isn’t a post after all, and I let it go.

I save these as drafts on my laptop, and at any given moment I have 10-20 drafts at various stages of doneness. I label them as drafts so they’re easy to find, and I’ll return to them from time to time. All of this happens in Microsoft Word.

The morning before my publish deadline, I read through near-finished drafts and find a post that feels right at that moment. This is a time of polishing. I cut as many unnecessary words as possible, especially qualifiers. I push for specificity in my language and try to breathe life into the points I’m making (not “trying to make,” which I just edited out) with specific examples. Ideally, I proofread, though I should do a better job of that by reading the whole post out loud.

Letting posts sit, as drafts, for a few days or weeks is the biggest change I’ve made to my approach since I started blogging. I made the shift when I shifted to fewer posts (1-2 / week) than I used to publish (3-4 /week). I’ve no doubt that posts are stronger thanks to this change, but ideally I wouldn’t have traded quantity for quality.

Nearly everything I’m describing happens on the train I take to and from work. I do my best writing first thing in the morning, usually at the beginning of the week when my head is clear. I mostly edit at night.

Having a place—the train—where I do the writing helps: whether it’s sitting in the same chair or the same train, putting yourself in the same location to write seems required for almost all writers. As Stephen King famously said, “This isn’t the Ouija board or the spirit-world we’re talking about here, but just another job like laying pipe or driving long-haul trucks. Your job is to make sure the muse knows where you’re going to be every day from nine ’til noon. Or seven ’til three. If he does know, I assure you that sooner or later he’ll start showing up.” Exactly.

My last step is to put the posts into WordPress, do a final reread and make last tweaks, and I hit the ‘Schedule’ button.

The best part is, eleven years and more than 1,100 posts in, when I hit that ‘Schedule’ button I still have absolutely no ideas which posts will have a big impact and which ones won’t. That’s all part of the process, one that’s equal parts faith and commitment.

(As a bonus, if you’re specifically interested in becoming a blogger, this post has helped a lot of people: What I Talk About When I Talk About Blogging.)

I have nothing to say

Most of the time, most ideas worth writing about don’t show up fully formed at the precise moment we stare at a blank sheet of paper.

Indeed, if we expect all of our useful, original ideas to show up only after we settle into the chair, we are setting ourselves up for a lot of frustration.

The ideas come at other moments.  Our job is to remain curious and attentive, so that we stop for long enough to notice our glimpses of passionate insight, of outraged exasperation or of simple, concise observation.

When these moments occur, we must hold on to them for long enough to write down the feelings we have, the core of the insight, and a few scratches about how the argument will flow.

Once that’s done, the writing boils down to the relatively simpler act of putting words around the thoughts so others can see them too.

Fundraisers in the Digital Age

One of the characteristics I don’t see people talk about as much when looking for successful, modern-day fundraisers are writing skills and digital proficiency.

It’s easy to think that the traditional job interview is a great way to find good fundraisers, and it is a good place to start. Fundraising meetings have a lot in common with job interviews: the potential funder is trying to figure out your story, your motivation for being there, and whether she connects enough with you and with what you’re saying to make a commitment to investing in a relationship with you and, over time, with your organization. A lot like hiring.

But it’s a mistake to stop there.

We know that today everyone lives on their devices. This means that a big part of the modern fundraiser’s job is to maintain and feed a web of relationships: a good fundraiser invests heavily in a core group of 20 relationships but is keeping a lower-touch pulse on as many as 100 relationships at various stages. This has gotten much easier thanks to technology – if you do it right.

The modern fundraiser’s secrets weapons are things like the ability to quickly craft a great email before or after a meeting; to sift through a lot of information online and find that one story that’s going to further the conversation you just had with a potential funder; to know when to call or to text or to write a handwritten note, and what tone and style to use in each medium.  If you can do this all fast and without breaking a sweat you can feed the network and be present and top of mind in many people’s lives.

This means that great fundraisers do more than just create connection in the room. Great fundraisers are a sense-makers, companions on the philanthropists’ journey to understand context and where their own philanthropic efforts fit in and can make a difference.

What I Talk About When I Talk About Blogging

I’ve had a lot of conversations in the past few months that start with people saying, “I really have been meaning to write or blog, but I just haven’t done it. Any advice on how to start and stick with it?”

Here are 12 things that I’ve learned since I started blogging in 2008:

  1. A structured time to write. Stephen King is famous for saying that step one in writing is to put your “butt in the chair.” Not glamorous, but true. 99% of my blog posts have been written on the train that I take home from work. And most of them come out very quickly – in 10-15 minutes. But I’ve discovered that when I don’t take the train, I don’t write blog posts. That’s when I write.
  2. Make a commitment. Commit to how much you’re going to publish / write / post. I’d suggest you aim high because you’ll probably do less than you intended (because that’s life). And “publish” because I think creating finished work (to your own standard) is important, because it lets you practice sharing complete thoughts that engage other people as readers.
  3. Set it up so someone is reading. I’ve been blogging for more than six years now and I’ve written nearly 1,000 posts. I absolutely, positively, would have given up after six months if I didn’t have readers. I’ve grown to feel that my readers and I have an unspoken contract: they commit to taking the time to read, think and (hopefully) act on the things I write that they find useful; I commit to keep on writing. And occasionally, they comment or reach out to say how a post has helped them or moved them or taught them something. That feels great. [If you’re writing for yourself or in a journal, this “someone” could be a colleague, a boss, a friend you respect, and you could commit to sharing 5 things you’ve written every month. My hunch is that if it’s just for you, you’re writing a personal journal, which is also important work but is something different.]
  4. Ignore your inner critic. We ALL think that everything we write isn’t good enough (not good enough for us, and definitely not good enough to have others read it). The irony is that the more you let yourself censor your own work, the less of your own work you’ll produce, and the less your work will improve.
  5. Remember that it’s much more important to write a lot than it is to write well. This is basically the same point as the prior point, written differently. When I was posting nearly every day, it helped me tremendously to know that if a post wasn’t good enough, I’d have another shot at it tomorrow. It’s helped me even more to go back to posts I’ve published and try to remember which ones I thought were the “good” and the “bad” ones.
  6. Remove the “am I saying something new?” filter. Because no, you’re not saying something completely new and that’s OK. The point is that it’s YOU saying it, and we care about what you think and how you make us feel when we interact with your idea and your emotions.
  7. Ignore the outer critic. Yes, sometime between here and there people you care a lot about will tell you to stop or to do things differently. Listen to them, contemplate what they say, but don’t commit to doing what they tell you to do. Any creative, self-expressive process is inherently delicate, a flame that’s easy to snuff out. Protect it.
  8. Keep it short. I’m highly partial to 200-500 word blog posts. Every time I write something longer than that it’s because I couldn’t make it shorter. Yes you might have a more technical or expository topic than I do, but by and large if you want people to interact with your ideas you need to present them as simply as possible, with as clear language as possible, in as few words as possible. Use this work to practice not hiding behind elaborate, obtuse language.
  9. Have a strong purpose, loosely held. Especially if you’re trying shift from being someone who doesn’t write to someone who does, I think it’s helpful to have a specific intention plus the freedom to write about what you want to write about. When I started this blog I thought it would just be about fundraising, but I didn’t have enough posts in me on that narrow topic, and the whole construct felt constraining. What I’ve found since then is that through the process of writing this blog I’ve figured out what this blog is about, and I think my readers get it too.
  10. Discomfort should happen. The reason you’re doing this is to grow. Growth comes through doing things you haven’t done before, aren’t comfortable doing, and aren’t good at today. If it feels hard, risky, or awkward, you’re doing the right things.
  11. Do it because it matters. There should be some deeper purpose, which isn’t the same as an external objective (as in, “this is how I’ll land a book deal” or “this will help me when I’m looking for my next job.”) I started blogging because I wanted to understand the job I was doing – fundraising – and what it meant, and could mean, to me and to the nonprofit sector. Over time that focus deepened into wanting to understand, in a much deeper way, people who give to charity, which led to an exploration of generosity, which in turn opened up a lot of avenues of further exploration. Ultimately, this blog has become a vehicle for understanding my own purpose and for sharing things that I’m learning or being challenged by along the way.
  12. Someday you won’t be able to live without it. My blogging continues to evolve, and its purpose and continues to shift. It changes as I do. But it is now part of who I am and what I do, and I hope never to lose that.

For all of you out there reading, thank you. I wouldn’t be here without you.

For all of you out there thinking about writing, I hope this helps.

[title apologies: Hakuri Murakami]

The Buy Read Paradox

I’m intrigued by the disconnect between the prestige and legitimacy afforded by being a “published author” and all the friction inherent in trying to spread your ideas by writing a book.

Think about the dropoff from:

The number of people who hear about a book → The number that buy the book → The number that read the book they’ve bought → The number that spread the word about that book

If you aren’t a known name or you don’t have an existing tribe whose permission you’ve earned (often over a number of years), simply getting the word out about your book is a herculean task.  And so, most books sell only a few thousand copies.

Nevertheless, being a “published author” still carries a real caché.  Especially if you write nonfiction, “published author” is a chalice of purported legitimacy and expertise (e.g. it’s a lot easier for a journalist or a TV producer to justify interviewing a published author).  What that means in reality is that the book gives you permission to talk about the ideas in the book, not the other way around.  It’s a pretty roundabout, lumpy way to spread an idea.

Which gets me thinking:

  1. 25 years from now, will the notion of being a “published author” be anachronistic, and, if that happens, what will replace it?
  2. Or, will the notion live on, because as a society we will always need a way to separate out “legitimate” idea merchants from the chaff.

If anything, it seems like we are going to see a proliferation of pathways to legitimacy, which gives people who want to spread ideas (but who don’t have access to the gatekeepers) more options.  That seems like a good thing, as the volume of ideas that will spread will likely go up.

The open question is whether, overall, more of the best ideas will get out.  My bet is: Yes.

What do you think?