The most important part of writing isn't the writing

I question everything I write.

Until I don’t.

That doesn’t mean I believe my drafts evolve into perfection.

Truth is I haven’t come close to writing the perfect piece, ever.

But what I’ve managed to learn over a few decades of writing is this:

The most important part of writing

is questioning and thinking about

what you just wrote.

This is the writer’s contemplative work that demands unmerciful scrutiny:

• Is this really what you mean?

• Will it resonate with the audience?

• Did you use a helpful example or accurate analogy?

• Did you allow jargon to slip in?

• Can you say this differently but better, quicker, more human and conversational?

• Is it reflective of the brand or individual you’re writing for?

• Would you want to read this?

• Does it educate or challenge what you think?

• Does it make you want to take action?

Here’s an accepted truth:

Anyone can write and putting words on paper or a screen is easy.

But not everyone is a writer – and that’s okay and also acceptable. Not everyone is an engineer either. Which is why it’s helpful for non-writers to understand how writers do what they do.  

Writing (the process) doesn’t look like

writing (the act) at all.

Writing is rooted in everything that is simmering before the first words are hammered out, after the first draft –  and second, third or seventh – or however many are required until you land on a draft worthy of being final.

Writing includes thinking, mulling, stewing, questioning, arguing with yourself, walking away and letting first words calcify, returning to test if they are strong or brittle, tearing elements down and rebuilding.

It looks more like sculpting than writing. That’s because it is art.

Writing also involves letting someone with zero subject matter expertise read your draft to find out if they can follow it, to see if it makes sense even if they don’t know the technical details. Because simplicity outperforms the bravado of expert posturing. Which is to say…

Good writing is hard.

It is never automatic, and never a given.

Writing something good, once, is in no way a guarantee that your next thing will be any good. It requires doing the hard work from scratch, all over again with no shortcuts, in hopes that it too might become good.

The myth of great ideas.

Great ideas (epiphanies!) rarely “just happen” in a first draft or any draft. It’s like the fleeing fireworks display in the sky – it’s looks pretty, briefly, followed by hazy residue once the twinkle fades as you await what comes next. Instead, great ideas are the tortoises in these races to the finish line, always plodding a bit slower than we’d like but worth it in the end.

In fact, epiphanies aren’t unexpected, out-of-the-blue thoughts or ideas at all. They emerge when you prune and edit everything that’s been taking up space – in your brain and on the page. In this sense, the epiphany becomes sudden, recognizable clarity as bloated language and jargon get removed.

The great idea emerges after carefully working and examining the entire landscape and finding it has been hiding in plain sight all along.

Good writing is never over.

However, at some point it needs to be ready or complete. Complete means as far as you can take it, as well as you possibly can, with what you know right now. Because a few weeks or months from now you’ll look at what you wrote and find yet another way, possibly a better way to say it.

For people who don’t do a lot of writing, this takes entirely too long.

For writers, there’s always a desire for more time to allow the best ideas and language to emerge and mature. And that’s because writers know what’s at stake, writers know what the right words can unlock.

These days a lot of written content feels disposable, unhelpful, noisy [add your descriptor here].

It feels like fast food: quick, convenient, seemingly necessary, but also lacking. And just like fast food, disposable content feels even less fulfilling after its consumed.

It doesn’t have to be this way.

Even the shortest post can have a powerful impact.

The deception is in how easy it appears (but now you know the truth).

Slow down.

Think it through (ask more Qs and then think some more).

And then write some really good sh*t.   

** For the record, I wrote and edited this piece across multiple days and sittings, challenging myself and what I believe about the process. Nothing comes easy.

*** The photo image is the cover of Steven Pressfield’s book of the same title and is a must read for writers.

Why every leader should be writing

photo credit: Israel Andrade

If you are the boss, the CEO, the president, the business owner, the executive director, the person the buck stops with, then you might want to heed this advice: you should be writing.

Arguably it could be the most important facet of your leadership. Here’s a bulleted list of why:

• Your people want to hear from you – not just at the quarterly meeting or when things are getting tense. They want insights based on your years of experience, miles on the odometer, your wins and losses, your relatable stories of what they are challenged with right now.

• Your people want to know what’s working and what’s not, what the plan is and what direction the company is headed. Don’t assume they know this or will remember it. Remind them regularly.

• If your company’s mission, vision, and values aren’t well known, or if they don’t sound like you, or reflect how you lead or where your organization is going, it’s your responsibility to consciously connect the dots or redraw the lines so people get it. This is foundational to your writing and messaging. 

• It is a way to crystalize your thinking before you start communicating. Bullet points have their purpose, at the right times and venues, but they are not a substitute for writing with intention or communicating specifics.  

• You will  have a record of your messaging and what was shared; a written reminder of what has – and hasn’t – been said.

• You will be sharing stories (making you more relatable) instead of regurgitating talking points (making you come across as unauthentic). 

• You provide important perspective to data, trends, successes, and where things fell short.

• It gets what is in your head onto paper or screen where you can refine your thinking. Because your first draft isn’t your final draft.

• You begin articulating what you believe about business, leadership and success based on real-life trial and error, not someone else’s that is captured in a book.

• By communicating, first in writing, and then finding additional ways to bring those stories to life, you are consciously setting and reinforcing the culture. 

• Because every business challenge is first a communication challenge, and open communication cures many ills.

• Because bad news never ages well, and the grapevine distorts reality.   

• You will cast a shadow of what good leadership looks like by sharing deeper insights, plans and priorities.

• You will be building the archive; leaving a legacy and a blueprint. And you will be more attuned to the passing of time and the inevitable passing of the baton when the time comes (and it always comes).

WHAT THIS FORM OF WRITING IS… AND ISN’T.

This isn’t thought leadership or convincing existing customers and prospects that you have the pulse or unique perspectives on business. That is an entirely different endeavor, and something you might consider as well.

This is internal communication, the most urgent of business communication.

It is a function that might not exist or is relegated to a communications team without your regular input.

This is culture building by the chief culture officer – you.

This is the priority you might never have considered your priority.

This should be happening already. If not, you can start now.

If you don’t know how to start, let’s talk, and then start writing.

If you are already writing, make sure you have a person you trust to challenge, question, push you and, perhaps most importantly, call your bluff when necessary.

Bounce ideas off them. Determine what sticks and what doesn’t. Decide what’s worth committing to type and then sharing with others in various formats.

Because writing isn’t as easy as it sounds, and can come across in ways you never intended without a good edit.  

Even if you don’t see yourself as the writing kind, there are ways to get your ideas to paper/screen. But you must convey them out. Look at them. Chew on them. Own them.

Your people will thank you. The next generation of the business will thank you.

And you will have zero regrets articulating what mattered most during your time leading the people who helped propel the business forward. It is what success looks like when your team believes in, and acts upon, what you’ve chosen to share.

Thoughtful leadership requires more of this overlooked habit

“I don't have time to read – I’m too busy.”

For years I’d hear that kind of a remark from a leader and assume I had no idea the kind of pressure they were under. Being none the wiser, I would give them a pass. After all, it is hard to make time for something that isn’t a priority.

Today I know better.

I get that some people don’t enjoy reading and that it feels like more work on top of the work they already must do. But keep reading (or stick with me through this post). It doesn’t have to be drudgery, and I believe it can become a priority if we focus less on the act of reading and instead look to outcomes reading presents.

Recently, James Clear shared this thought on the value of reading and it struck a chord:

"Reading is like a software update for your brain. 

Whenever you learn a new concept or idea, the "software" improves. You download new features and fix old bugs."

That should push us to think about how many “old bugs” we have that need fixing, as well as how many new ideas that could be of real benefit if we’re open and curious enough. 

Now imagine the leader of your organization working on Windows 98, using a decade-old Blackberry, and sending email from an AOL account. They’ve signaled that these tools are necessary if not important, but refused relevant updates for their tools, processes and practices to advance the business. 

Processing new information, and then applying that which is useful or helpful, is in part the art of remaining relevant — and we need our leaders to be relevant leaders who know where to guide us and our organizations. 

Looking back, I can pinpoint which leaders and mentors of mine were avid readers and curious thinkers, in part because we talked about books and new ideas. It shaped my thinking and encouraged me to dig in and dig deeper.

Conversely, I am also reminded of those whose leadership style was less about curiosity, innovation and new ideas. Instead they held fiercely to rigid views and a “this is how we (meaning you) do it” mentality.  

Still think you don't have time to read?

In the last three years I've nearly tripled the amount of books (ideas) I consume. Like you, I’m still the same busy human — running a business, raising a family, and being pulled and distracted in multiple directions. My consumption of deeper content (vs. social scanning and intermittent browsing) has grown by listening to books — in the car, while exercising or walking the dog. This is not a new idea, but I was slow to adopt it. But I’m choosing to steal back some of that lost time, reclaim bits and pieces of it, while also leaving enough margin to think and also unclutter the mind.

Last year, I completed 71 books. It wasn't a chore. Only a third of the titles were overtly about business. I track them not to “keep score” but simply to remind me of what I’ve read and what I might want to revisit. A log also reminds me if I’m active in my reading and if I’m getting derailed.

I'm continuing to gain perspective on things and people that I was previously ignorant about (software update). And no doubt I'm thinking differently and more broadly than I did just a handful of years ago. My curiosity quotient continues to rise.

Further, a diverse selection of reading material can open us up to becoming more empathetic and aware of those around us. But it requires us to humbly approach new ideas, different perspectives, and unique voices with an “I don’t know what I don’t know” attitude. Although this HBR article isn’t a recent one, it’s still relevant. And it’s comforting to know we’re in good company as we embrace this critical leadership habit.

We owe this kind of upgraded thinking and curiosity to our clients and colleagues, family and friends. We also owe it to ourselves. And it’s as easy as opening a book or pushing play on an audio version.  

So to all busy leaders and those who aspire to lead others: read to learn, read for enjoyment, but also read to lead. There’s no doubt that you, and those around you, will see the benefits of being not just well read, but more engaged and curious in contrast to that time when you didn’t have time to read.  

READING OLD NOTES: gaining insight through reflection

I keep a stack of moleskine notebooks and serviceable knock-offs on a bookshelf in my writing studio. They are filled with meeting notes, doodles, writing prompts, sketches, and lists of peculiar word pairings that I imagine using in future pieces. There’s also some wise advice I’ve picked up and scribbled into the margins during this work-and-life journey.

I admit that once these notebooks are filled, I rarely pick them up or thumb through them again.

That is until recently.

I had been feeling anxious about a writing assignment and a personal project. I was struggling to start, to finish, to find the right words. They weren’t coming. More than writer’s block, it was a questioning of my abilities to perform my core work.

So I began thumbing through old words. Past projects. Thing that at one time seemed daunting. Things that felt important to commit to paper.

I wasn’t looking for anything particular. I was simply revisiting and reflecting on past experiences and old ideas.

And it made me stop and think: why is it that we scan old photo albums (or file folders) with a sense of wonder and excitement? Why does Facebook send us anniversary milestones of friendships? Why do we painstakingly curate playlists in Spotify from the 80s or 90s when there’s so much new music across any genre for us to enjoy? Why do we show up and honor, in our own special way, those whom we’ve lost?

Because we need to be reminded.

Reminded of what’s important and what matters;

what we’re striving for and what keeps us in the game;

what gives us life and purpose, hope and joy.

Looking for the right words and answers continues to be an imperfect and ongoing search. If not now, then assuredly later. And you, I’m assuming, will have your own specific search that demands resolving – from the mundane to the monumental challenges.  

As I thumbed through some old notes, I found some words of advice and inspiration, and a few that served as a kick in the pants to keep going, to pick ourselves up, to get better, and to never stop.

In some cases it was as if I was reading these points for the first time. For others, I had a different perspective thanks to the experiences I’ve has since I first scrawled the words.

Maybe these words – forgotten and tucked away in a notebook on a shelf, from writers, creators and, more importantly, doers – are exactly what I need to reflect on when the load feels heavy. And maybe you, too. Maybe these words needed some light thrown back on them to push us forward. Perhaps new eyes on these once-written, spoken and acted-upon words can breathe new life into whatever it is we need to do but haven’t.

I hope they are helpful, encouraging, or a kick in the pants. If they are, then write them down. Put them in a notebook. Add to them. And consider revisiting them from time to time.

Traveler, there is no road;

you make your own path as you walk.

As you walk, you make your own road,

and when you look back you see the path

you will never travel again.

– Antonio Machado // poet

“How we spend our days is, of course, how we spend our lives.”

– Annie Dillard // writer

“When we are merely competent, the value of our work is diminished until it can eventually be outsourced to the lowest bidder – making us a dispensable commodity.” (Don’t be merely competent. Be unmistakable.)

– Srinivas Rao // business author, podcaster

CRITICIZING IS EASIER THAN CREATING.

(shut up and get to work.)

“The trouble with comparing yourself to others is that there are too many others. Using all others as your control group, all your worst fears and your fondest hopes are at once true. You are good; you are bad; you are abnormal; you are just like everyone else.”

– Sarah Manguso // poet

“Emotion before evidence. Otherwise data will kill a good story on contact.”

– Todd Henry // writer, creativity consultant

“Keep being curious. Keep being a student.

As soon as you stop doing that, as soon as you stop playing,

you stop creating great things.”

 – Matthew Luhn // writer, Pixar Animation Studios

At the end of my suffering, there was a door.

– Louise Glück // poet

“If you listen to everyone, you will lose yourself.

You were hired for your expertise. Deliver that.”

– Ruth Carter // costume designer for Black Panther

But what if I’m not a real writer/artist/entrepreneur/etc.? Just sit down and do it.

What if my idea isn’t any good? Just try. Do it anyway.

What if nobody sees it? It’s not about who sees it, it’s about why you did it.

What if I’m stuck? When you’re at an edge, push through it.

What if this was a gigantic waste of time? Trust that it won’t be.

 – Allison Fallon // writer, coach, adapted from perspectives on writing

DARE. MIGHTY. THINGS.

Then do the work to achieve those things.

Fear is opportunity in disguise

When the landscape is unfamiliar, fear can set in. It's also where opportunities to discover and grow kick in. (Illustration credit: Jon Klassen) 

Your work.

It’s probably something you're great at, some place where you shine bright.  

Which is to say – you do what you know and you do it well. 

With that kind of knowledge, chances are you tend to stay in your lane.

And you stay there in order to champion your expertise (that’s a much easier narrative).

The inverse of this is fear of the unknown.

Or, in a results-driven world, fear of failure.

But what if that so-called fear was just opportunity in disguise?

*  *  *  *  *

What if you hinted at the idea that among all of the things you could possibly deliver, discovery just might be the most important?

Instead of loading your pitches for clients and customers with buzzwords of the best-in-class variety you showed a bit of vulnerability, perhaps even came clean by revealing that you didn’t have a trademarked approach to guarantee predictable results from rote formulas.

Instead of issuing the next RFP (or responding to it) with restrictions that actually stymie creative solutions, what if it went like something like this:

Here’s our challenge. We’re ill-equipped to solve it alone. Admittedly, we don’t know what we don’t know. We’re asking for your insight and expertise based on a track record of solving similar challenges. Might we talk?

Confront what you’re really afraid of: is it being vulnerable? Being perceived somehow as less smart or running out-of-step with a crowded field of thought leaders? Are you content faking it until you make it – or, worse, get found out?

*  *  *  *  *

If you’re anything like me, you’ve been there and done that.

And so you’re veering outside of your lane, taking some calculated risks, and embracing a journey filled with insights that provide an interesting and highly viable set of outcomes that are all but impossible to predetermine in a plan. (Because plans change and course correction is necessary. Which is why you’re more interested in roadmaps that provide multiple avenues -- and unexpected detours too -- that help you get to your destination.)

Perhaps you’re finding out fear isn’t that scary after all.

Maybe fear is just another four-letter word.

You're considering it as a prompt that really means ‘get ready, this is going to stretch you.’

And by embracing fear for what it is, perhaps you’re starting to realize that your comfort zone is really your complacency zone.

Complacency: shouldn’t that be your fear?

*  *  *  *  *

If there is anything else to be afraid of, perhaps it is being average.

Or not realizing your potential.

Or intentionally foregoing meaningful experiences and new relationships because they are unfamiliar.

Or blending in to the point that you’re indistinguishable from the crowd.

If fear is your opportunity to grow, then you must equally consider what it means to play it safe.