Writing advice: what to do when you’re stuck

ideas that pop with passion icon[Updated] Anyone can be a writer, it’s true. But sometimes—whether you’re writing for the web, crafting an article, a direct marketing piece or a book—you’re going to get stuck and it can seem as if no amount of rewriting is going to fix your copy.

Don’t wait for that sinking feeling to set in.

Here’s the first thing you must do.

Keep writing.

Don’t give in to that feeling that says you need to walk away.

Giving in is easy. It’s what many people do.

There are cases where you need to shift gears for a bit (and I’ll come back to that). But unless you keep working at your craft and your ideas, you’re going to lose any momentum you started with.

There’s an even bigger danger.

Unless you’re in the deadlines business like I am, there is also a good chance that if you put that writing project away, you might not come back to it. Ever.

Stop with the Point-A-to-Point-B thinking. Be more abstract.

Ideas and the business of writing them down is not a linear practice. In fact, it’s rare to be struck by a fully formed thought that’s ready to share. That’s just the low-hanging fruit, my friends. The rest takes time to ripen. And often it’s going to take you in directions that may surprise you as much as your reader.

Here are a few methods I use when I get stuck. You can use any of these, too.

The tangential method

Find a good quote about the subject you are writing about. Don’t just slap that quote into your copy.

The writer’s first devotion is curiosity and you feed it by asking questions.

Who is the speaker behind the quote? Are there any articles posted online about this person? Book reviews?

How might what they have to say about one thing relate to another thing in an entirely unexpected way?

A few minutes of satisfied curiosity can provide you with an entirely new angle on what you’re writing about.

Here’s a secret: it’s one of my most reliable ways of coming up with new topics for my newsletter.

The switching gears method

I said earlier that you have to keep on writing when you’re stuck. But that doesn’t mean you have to keep bashing your head against the wall and wishing for a different result. Some ideas need to simmer. In the meantime, write something else.

Creativity is a weird visitor (click to tweet). It often walks into your house, puts its feet up on the sofa, grabs pen and paper and tells you it’s working on something. Let it do its job. Just don’t let it switch on the TV.

Switching gears means that you might not be working on the thing you started on in the first place, but you’re still producing.

Practice and discipline. These are your best teachers.

The backstory method

This one applies to fiction writing. Having trouble making a character believable? Invent a backstory and write it down. Need help asking the right questions? Go to one of those free online dating sites and look at the questions they ask of people when creating a dating profile. Fill it in. The answers you’re being asked are meant to help other people decide if you’re likeable and compatible. This is a good resource if you’re stumped.

With a fact-filled backstory (okay, made up facts, but I’m sure you get where I’m going with this), you have new ways to approach your subject and write convincingly. After all, you totally know this guy now.

The undoing method

Some ideas are just not ready for primetime. Some are just crappy ideas. A good way to test yours is to turn them inside out. Play devil’s advocate. Write a short piece arguing the opposing point of view.

One of my business lines is speechwriting. I sometimes use this method when I’m finding the copy isn’t as persuasive as I need it to be.

Undo your arguments.

You’ll quickly reveal the cut line that separates the facts you know are true from the rest of the points that you simply feel are true.

Belief, bias & rules

thinkit creative logo blackBack in 2001, when I first set up my writing business, here’s a small sample of what was common advice at the time.

You must have an office in an office park, otherwise you’re not a real business.

You must have a fax machine. And a separate land line. Otherwise people won’t take you seriously.

It’s okay if your website is nothing but static content on cheap hosting. You’re going to do most of your direct marketing in person, through mail or by phone anyway.

You must accept lengthy terms of payment well in excess of 30 days and always by cheque, otherwise you’ll seem difficult to work with.

You need to have in-house staff and have a wide range of services to offer, otherwise you’re just a freelancer.

Belief and bias about a “one right way” to structure and run a business comes from what people think is true, until it’s not.

More often, these notions are a by-product of habit and sometimes even of a self-insulating arrogance about the world. This is how rules (especially unwritten ones) propagate.

Rules are not facts. Rather, they are subject to change by deeper, rarer truths about what your market expects and wants and needs.

You can choose to buy in to the mythologies of others. Or you can make your own.

Either way, the rules that you choose to adopt are going to serve you and your customers best when they show the value of what you do, rather than just adhere to someone else’s idea about how the work needs to get done.

What I have learned in my first 10 years running a successful business

thinkit creative logo copywriterAlthough I find I am still pinching myself in disbelief, 2011 marks ten years since I first founded thinkit creative and took a bold step into this business as a writer, speaker and marketer. It’s been the best decade of my life so far and I’m really looking forward to what’s in store for the next ten years working with clients, friends and colleagues.

To mark this occasion, I’m sharing with you this list of things I’ve learned along the way…


You do have to be a little crazy to start a business.

The thing that keeps people from taking a risk in life is the same thing that fuels those who do take that risk: fear.

Fear is fire. Use it right and you can stay warm, eat well and find your way in the dark. Just manage it with great care.

If you’re not doing at least one thing that scares you once in a while, you’re not trying anywhere near hard enough.

You’ll be amazed at how generous people are in sharing with you what they know. All you have to do is ask.

It takes a long time to be great at what you do. More than just putting in the hours, you must practice your craft.

Only do what you like to do and what you are good at doing. For everything else, find someone else to do the job.

It’s not hard to spend too much time working, but you can’t ever spend too much time with your family.

Even when you’re new, it’s surprising how many people you know.

Use fewer words.

My best ideas come to me when I’m doing something other than work. This is why it’s important to have a hobby.

There’s a big difference between work and a job. Work is hard, but it’s also that way because you care a lot about it. A job is just a place you have to go to do something you have to do.

The fundamentals that go into making a business successful are time-honoured and time-intensive. Don’t be fooled by anyone who promises you a fast-track to fortune.

Build a great product or service, think always about how you can make things better for your customers, and put in the hours. Do these things and you’ll weather any economy.

Some people are just difficult. No matter what you do, they’ll just keep pushing the bar further. They’re not interested in anything other than making demands of others. Stop wasting your time on people like that.

Analogous to what Louis Armstrong once said about music, there’s only two kinds of writing: good and bad.

People often say you need to write every day to be a successful writer. I disagree. What you do need to exercise daily is your own sense of good taste.

Memories are faulty. Get it in writing.

Time is money, but don’t be stingy. It’s good to be helpful. It costs very little and the difference it can make can be substantial.

Always remember birthdays.

Networking is the oxygen of your business. Learn to do it so that it’s like an involuntary muscle that flexes on its own.

Good people with a positive outlook aren’t all that hard to find. Surround yourself with them.

There will be bad times. No matter how hard you work or how hard you plan.

Be practical.

No matter how deserving you might think you are of success as a direct result of how hard you work, be humble and acknowledge the role that luck has played in getting you where you are and in giving you what you have.

Forgive people personally, but don’t ever forget dishonesty in business.

No matter who is paying, your client is the reader, listener or audience.

Give an audience only as much as they need to understand what you have to say. Leave room for them to see themselves in your idea.

Keep a box of thank you cards on your desk at all times.

It’s not about the money.

Writing is a lonely job, but as Margaret Atwood reminds, “nobody is making you do this.”

You can learn almost everything you need to know about how to be successful in business and in sales by studying the habits of a great restaurant and a professional server.

If all you do is spend time listening to those who call themselves thought leaders, you’ll be nothing but a follower.

Don’t go cheap on things that have your name and phone number on them…business cards in particular.

Hire a great accountant.

Know a mean lawyer.

Don’t waste time with difficult people.

A cheap office chair might save you a few bucks, but it won’t save your back from misery.

No matter who you are, there’s always someone else out there who is smarter than you who can build a better product. So be good to people, always.

If you’re not worrying about looking after the little things, big things will get you.

Almost anyone can talk about how complicated something is. But only a few can teach how simple it can be.

If what you do matters to you, communicate with passion. Otherwise, what’s the point?

If you’re satisfying everyone, you’re not doing it right.

Don’t use so many semi-colons. Like Kurt Vonnegut once said, “all they do is show you’ve been to college.”

You can’t teach someone how to write. That’s a hustle. However, you can always learn how to be a better writer.

Be choosy about metrics. Just because you can measure something doesn’t mean it’s relevant.

Know the difference behind the motivations of someone who wants you to work for spec and someone who asks you for your professional advice.

If you haven’t heard from a client in a while, call and ask why.

Get over yourself. Others think about you far less than you realize.

Give a damn when no else is looking. Especially then.

Worrying about things is just something that business owners do. Accept that, and don’t let it consume you.

The more you listen and ask questions, the more you will be valued as someone who is great to talk to.

You only own the first draft. After that, it becomes a team effort. So put everything you can into that draft.

There’s something to be said about just showing up. I’ve found a lot of new business just by being somewhere at the right time and being approachable.

The things you worry about the most are the things that tend to be the least likely to come true. It’s the unexpected that jumps up and bites you the hardest.

It will piss you off how often you have to learn from your mistakes.

Don’t swear unless you really, really need to.

Be curious.

Spend far less time talking about you. Show how you can help others.

Exercise often.

Have goals, but don’t be one of those people who sticks rigidly to a five-year or ten-year plan. You’ll be amazed by how much there is to be gained by just letting things happen.

Don’t spend too much time alone, no matter how solitary you think your work is supposed to be.

If it’s a business tool that makes money for your or is mission-critical to your operation, buy the best.

Free comes with a price.

Even writers and editors have an editor. And you can’t pay a great one enough for what they can do for you.

Be generous with everyone. Make an extra effort for those who don’t have the resources or opportunities that you have had.

Always speak well of others. Even about those who have done you wrong.

Even if you live in a sprawling metropolis, everywhere is a small town when it comes to your personal reputation and that of your business.

You are what you post.

If your client is fun to work with, pays on time and values your advice, no job is too small or favour too great.

To launch a business and make it grow year after year is a bit like losing weight and keeping it off: there’s no magic pill that’s going to make it happen, but there are always plenty who will try to sell you otherwise.

When you love what you do, it doesn’t feel like work, but it’s still hard. The difference is that you don’t care how hard it is. You just want to do something great that you can be proud of.

Everyone underestimates how much luck there is in a recipe for success.

You know you love what you do when you willingly give up a lot to protect it.

In the service industry and in any economy, good people are always in demand.

Ten years goes by really quickly when you do what you love.

Business apps for iPad: a writer’s take

At the consumer level, it doesn’t take very long for the iPad to win people over. It’s easy to see its appeal for personal use (and I’m pretty sure I don’t need to rehash all the reasons why here).

But what about for business? That’s an area that’s still being explored in terms of finding ROI. So let me share what I know about that.

I’ve been using my iPad professionally since its US launch back in April, so I’ve had some time to really think about how I can best use this device. I’ve also spent a fair amount of time trying out a wide assortment of apps made exclusively for this iOS platform. Some apps surfaced with great promise and fanfare. Others have had to work hard to earn their keep.

So here’s my take as a professional writer on the apps that I consider must-haves:


To be clear, the iOS version of Apple’s slideware application is not a complete substitute for its much more powerful desktop counterpart. This version is considerably scaled-down. But that’s okay, because as I see it, Keynote for iPad works best for one-on-one presentations versus addressing large groups.

When I meet clients and prospects face to face, I like to share with them some samples of my work. I used to do this by maintaining a large portfolio book—something that’s not always practical for every meeting. With Keynote on my iPad, I create customized presentations with writing samples that the reader can flip through and zoom in as needed. It’s really handy…and it is by far my most effective presenting tool for generating new business.

I’ve blogged about this service before and I’m glad to do so again. I do a lot of research in my line of work, plus I’m a consummate reader. It can get tricky to try and keep track of everything I want to read, particularly when I’m pressed for time. With Instapaper, I just click “read later,” and it saves the link without all the hassles of bookmarks. Later on, with Instapaper’s iPad app, I can read those saved articles at my leisure, including in “dark mode” (black background against white text), which I find is much easier on the eyes. The good stuff gets added to my Yojimbo database and I toss out the rest.

Another long-time favourite tool of mine on the desktop. The developers just launched the iPad version a little more than a month ago, and in that short period of time it’s proven its worth to have a place on my springboard. It’s the simplest way that I know of to manage texts, PDFs and images (among other things) on multiple devices. At this stage, the iPad version doesn’t yet allow for generating new documents (the developers promise that’s coming soon). For now, it suits me fine as my one-stop reference for white papers, academic articles, favourite stories, and quotes.

IA Writer

There are two processes to my work as a writer. First, I generate raw ideas and write them down quickly. No editing on the fly. Just text in its most bare-bones form. This is an important part of my work and so I don’t want any distractions. On the desktop, I use either Yojimbo or TextEdit for that task. On the iPad, there’s Pages, which does have its place at the formatting stage (which is the second process in my work). But I want something that simply does text.

Enter IA’s Writer for iPad. Minimalist features. Just start writing. The app looks after saving your work and if you have Dropbox, it syncs your work to your shared folder so you can access your work later from other devices. But the best part of all is its enhanced keyboard. It adds just the right number of added functions that are otherwise either missing or hard to get to with iPad’s standard keyboard. Key among these: move forward/backward by word, apostrophes, quotation marks and hyphens.

As with its counterpart. Keynote, Pages for iPad is a scaled down version of the desktop word processor. It does a competent job at fine-tuning and formatting simpler documents, but I’d advise against trying to use this for performing any kind of detailed edit of a document. In my own workflow, it’s been largely eclipsed by IA Writer

As a writer who is also speaker and presenter, lifelong learning is part of my craft. TED Talks are a great learning tool both in terms of having great content and powerful presentations. I much prefer watching TED Talk videos on my iPad because it feels more personal. It also forces me to pay attention more carefully than on my desktop, where there are always distractions competing for my attention.

Jumsoft’s Money app makes the cut as the easiest way I’ve found to track expenses. And it does so without me having to deal with a lot of the needless nuisances that tend to plague apps in this category. To my knowledge, it’s also the only one that syncs entries between iOS devices and Mac desktops.


Having tried several sketching and handwriting apps, I settled on Penultimate because—like so many others on this list—it concentrates on doing one thing really, really well. In this case, it’s the ability to visualize my ideas quickly.

For me, Penultimate is the one app among so many that are out that that has the closest feel to working with a felt-tipped pen, making it a lot easier to start working with your fingertip on the screen without too much hassle. In meetings where I’m talking about an ad concept, for instance, I can sketch a rough idea quickly and email it to others if necessary. It’s also handy for writing out directions or anything else that I’d otherwise me sketching on paper.

Plenty of praise here for this app, which lives up to its claim as “your personal magazine.” True, Flipboard’s main purpose is to transform columns of social media into something that has the look and feel of a magazine. And it does this rather well. It also excels where most newspaper apps fail, it presents news articles in a way that encourages you to read more, but without resorting to the everything and the kitchen sink approach that tends to clutter so many apps (and I’m looking at you, Globe and Mail).

Honourable mentions…

Jumbo Calculator
It’s a mystery why Apple opted against porting to iPad their Calculator app for iPhone, but Jumbo closes that gap with a simple app with big buttons.

CBC Radio
Not directly a business tool, but sure comes in handy for checking the news when I’m on the go. Bonus points for sporting an intuitive design.

Kobo Reader
Better selection and better prices than iBooks, and none of the ridiculous kludginess of Amazon’s Kindle app.

I use this to post to this blog and revise my website from anywhere my business takes me. It’s simple and straightforward. And free. Which is rather nice.

This is my go-to app for brainstorming and mapping out my thinking when confronted with a problem. It’s simple with just the bare elements of what I need in a mindmapping application. I just wish it would support Dropbox syncing.

Yoga with Jamine
Taking a health break is an important part of any healthy enterprise. A few minutes of yoga can really hit the spot on a stressful day. I find this Yoga app so much more useful on the iPad…the videos are larger and easier to follow versus on the iPhone.

Easy to use twitter app, but doesn’t get updated as often as it should by the developer. Could go from being good to great with a little more TLC.

Kayak HD
Best of the breed for booking flights and hotels online.

Be nice to your back: buy a good office chair

This came up in a discussion I had the other day, and the advice I offered is important…the kind that’s based on “don’t make the same mistake as me, folks.”

If you spend a lot of time in your office, buy the absolute best, most comfortable, most adjustable office chair you can find. Put “low price” at the bottom of your list of must-haves.

You are going to spend more—maybe even a lot more—than you would by buying the chair featured in your local special-of-the-week flyer. But take it from me: don’t buy a cheap chair. I’ve gone through a legion of them over the years, and there are only two things you can count on: a cheap chair will kill your back and you’ll be back at the store again soon looking for a replacement.

Lots of folks have great things to say about Aeron chairs. I liked them too and nearly bought one until I discovered Steelcase’s chairs. Two models in particular: Leap and Think.

Better range of adjustments, solid parts that fit into a sensible sustainable development strategy, plus a good supply chain and service network. Those are all pluses…but the key benefit is that these chairs are really comfortable…even in cases where you’re sitting for extended periods.