5 Tips to Become a More Confident Writer

They say the best book to write is the one you wish you had and couldn’t find — and that’s exactly why I wrote Getting From College to Career, which was first published back in 2007. 


I really struggled to start my career in my 20s, and I wrote the book to help make that path easier for those who came after me. (Once an RA, always an RA!)

I’m thrilled to announce that HarperCollins will be publishing a fully updated third edition of Getting From College to Career that will be available in 2024. 

Not surprisingly, one of the biggest changes is including advice on how to use ChatGPT and other artificial intelligence tools while searching for jobs. 

I’m also scrubbing a surprising number of references — to fax machines, MySpace and quotes from celebrities who’ve been canceled).

Last month, I shared some of my tips on public speaking, so this month I thought I’d offer some advice on writing — including how I’m using AI tools in my own work.

1. Avoid a Blank Page

I’ve always been a fan of outlining, and AI can be helpful at this early stage. My friend Jeremy Schifeling, who I interviewed for the new edition of Getting From College to Career, is the head of marketing at Khan Academy and co-author of the book Linked: Conquer LinkedIn. Get Your Dream Job. Own Your Future (for which I had the pleasure of writing the forward). 

Jeremy said the wisest thing I’ve ever heard about AI: “AI solves the ‘blank sheet of paper’ problem.” 

One of the ways I’ve been using AI is to feed a topic I’m writing about into ChatGPT to see what it generates. Then I use that content to spark my own ideas. 

Outlining has been particularly helpful for developing LinkedIn Learning course scripts — a process I just completed for my third and fourth courses, both on internal mobility, coming soon!


2. Speaking Is Often Easier Than Writing

When I’m stuck, I take my hands off the keyboard, turn on my dictation app and just talk. (In fact, that’s how I produce these blog posts and newsletters — by talking through my ideas with the team at Rep Cap!) 

My favorite compliment is when people tell me that my writing sounds like my voice. I like my newsletters and blog posts to be conversational, and talking is a great way to achieve that. Plus, it’s often easier to talk through a roadblock or a paragraph that’s giving you trouble than to write it out. 

3. Produce a Sh*tty First Draft

In her book Bird by Bird, one of my all-time favorites, Anne Lamott famously wrote: 

“The only way I can get anything written at all is to write really, really sh*tty first drafts.” 

That’s advice that I follow religiously: No matter how bad something is, it’s always easier to edit than to start from scratch. 

And when I’m really stuck, I go back to the classic Julia Cameron practice of “morning pages”: Every morning, I get up and write three pages, just to get myself in the habit of moving forward.

As you can see, much of being a good, confident writer is just overcoming writer’s block and tricking yourself into getting things done!

4. Keep an Ideas File

There’s a reason so many of us have our best ideas in the shower — good topics don’t always come to mind when you’re sitting at your desk, fingers ready at the keyboard. That means you have to be ready to capture them wherever you are at that moment.

I keep ideas everywhere: in Evernote, in my email, on a notepad, on Post-It notes stuck to my computer screen, texted to myself.‌ And when I’m working on a particular project, I keep a Virgo-esque folder system where I store ideas for different chapters in different folders so I know where to go when I’m ready to start writing.

Whenever you have an idea for a blog post, a tweet or an article: Save it. You never know where your next big idea will come from!

5. Don’t Underestimate the Power of Stories

ChatGPT is an incredible tool for kick-starting and supporting the writing process, but what it can never do like you is give your personal opinion or tell your personal stories. Our job as writers is to figure out how to use AI to supplement what we do while staying in the driver’s seat.

AI can’t write about how I felt when my pants stopped fitting, or my nerves playing the lead in my musical debut, or how I coped with returning to a changed NYC during the pandemic

Sometimes I reveal things in my writing that I’m almost surprised that I’ve shared. But I’ve realized that those pieces — the really human ones — are what people like best.

What are your top tips for writing or questions about how to improve? Please share

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hi, i'm lindsey!

Lindsey is a globally recognized career and workplace expert and the leading voice on generational diversity. She has spoken for more than 300 audiences including Google, Goldman Sachs, Estee Lauder, Stanford and Wharton. Lindsey is the author of four career and workplace advice books, and her insights have appeared in media outlets including The TODAY Show, CNBC, NPR, the Harvard Business Review and the Wall Street Journal.


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