5 Things I Learned the Hard Way About Being a Writer

Real talk for anyone brave enough to put their words into the world.

I used to think that once I got published, everything would finally fall into place. That the self-doubt would disappear. That I’d finally feel like a real writer.

Spoiler alert: it doesn’t exactly work that way.

Over the years, I’ve made just about every writing mistake you can imagine. Some were small and mildly embarrassing. Others still make me wince when I think about them. I’ve written things I regretted. I’ve chased the wrong projects for all the wrong reasons. I’ve let rejection shake me to the point of paralysis, even though I’ve worked in publishing and know better.

But every misstep came with a lesson. Some of those lessons were painful, but they also gave me the insight and empathy I now use to help other writers move forward with more clarity, confidence, and compassion for themselves.

So, no, this isn’t going to be a “10 hacks to write your bestseller fast” kind of post. This is real talk. The kind I wish someone had sat me down and shared early on in my career.

If you’re just starting out, maybe this will save you a little pain.

If you’ve already made any or all of these mistakes, welcome to being a writer! At least we’re in this together.

Here are five things I learned the hard way about being a writer:

1. Writing about real people is riskier than you think.

I won’t argue with Anne Lamott, who said, “You own everything that happened to you. Tell your stories. If people wanted you to write warmly about them, they should have behaved better.”

She makes a great point, and you are definitely within your rights to tell your side of the story. Just make sure you’re okay with the consequences…and I don’t just mean the consequences for you.

Back when I was on staff at a local magazine, I wrote what I thought was a funny little personal essay about a Fleabag-level uncomfortable dinner with an ex-boyfriend’s family. I figured no one in his family would ever see it. It was a small local print publication, and they lived out of state. What could go wrong?

Turns out, they had ordered a subscription to be supportive.

Let me be very clear. While these people had said some pretty insensitive things to me—some of it likely because of cultural differences—they were good, private people. And they were humiliated.

When I heard how deeply hurt they were and how hard they were being on themselves, I felt sick with shame. I still cringe thinking about it. Maybe they should have behaved better, but my response was not proportional.

To this day, I wish I had thought harder about how it would land in their hands, not just on the page.

Lesson: As the saying goes: write hot, edit [and publish] cold. Looking back, where I went wrong was putting this into the world when I was still smarting from our breakup.

So write freely in your drafts. Let it all out. But before you publish, do a gut check. If someone in the story saw it, would you be okay with the consequences? Sometimes the story is worth the risk. Sometimes it’s not.

2. Pantsing your way through a draft can work, but it’s not always pretty.

I completely agree with the famous E.L. Doctorow quote about pantsing. You know the one: “Writing is like driving at night in the fog. You can only see as far as your headlights, but you can make the whole trip that way.”

Plenty of award-winning and internationally best-selling authors get there without a map.

I also know first-hand that you can reach The End that way because I pantsed my way through my first book and it worked. Sort of. I finished, and I even landed an agent, but without a plan and now too many cooks in the kitchen telling me where to go next, my year-long revision I got further and further off track. It was an experience of extraordinary frustration. 

I’m not suggesting you need to tightly plot and stick to an outline, but it can help dramatically if you at least know where you are headed. Otherwise, it’s like trying to drive at night in the fog without knowing which direction you’re pointed. You might end up somewhere good, but you’re more likely to drive right off a cliff.

Make your book, your revision, and your life easier, by knowing the following when you start: 

If you’re writing fiction or memoir, know where your character is at the beginning of the book, what they want, and how they’ve changed by the end.

Or for nonfiction, know where your reader is starting and how you want them to have changed by the time they close the book.

3. “Should” is a terrible reason to write a book.

“Should” might even be the worst reason to write a book. Trust me. I’ve read a lot still-unpublished manuscripts that start there. Also, I did that once, and I crashed and burned.

After my first book came out, I was speaking across country, signing my books in bookstores, and people kept asking, “When’s your next book coming out?” Author friends asked. Mentors asked. Actual fans asked. The pressure was real.

I had kind of an interesting idea, at least interesting enough in certain parts, but I didn’t have anything I was burning to say. I didn’t wake up wanting to share an idea or message or bigger movement with people. No, I woke up thinking – oh god it’s been too long since I’ve written a book, and my friends are getting new book deals, becoming international bestsellers, even my STUDENTS are getting their books published and winning awards.

But I did what I always do when I want something. I buckled down. I’m a hard-working, determined woman. I had two kids by then and very little writing time, so I wrote at 4 a.m., in gym locker rooms while the kids were in daycare, even in hotel bathrooms while my family slept during yet another military move.

I finished it. 🎉 But then my agent read it and... she hated it.

And she was right! It was okay. There were some good moments, and it was written professionally enough, but it didn’t have something fresh to say. It wasn’t gripping. Except for a few parts, it wasn’t moving, and it flat-out wasn’t going to sell.

I see this all the time with authors who really haven’t thought out their “why” but are pumping out the book they think they should write, just so they can say they can.

If you want to write a book because you can’t stop thinking about it or because your idea keeps you up at night or lights you up, you can take that energy all the way to the bookstore. But if your main inspiration feels like a “should,” stop and think about the book you really want to write.

In short, write the book that lights you up!

4. Rejection is not personal (even when it really feels that way), and it doesn’t mean you won’t get published.

I’m embarrassed to say that even though I’ve been on the other side of the desk, reviewing queries and deciding what to reject or request, sometimes it’s still hard not to take it personally when my own work gets rejected.

It has been years since my agent rejected that so-so book I mentioned a minute ago, and that rejection is part of why it’s taken me so long to finally finish a new one. Some of that was life getting in the way, but you’d better believe that a lot of it was self-doubt.

And I know better!

Think about it like this: If you walked into a bookstore with twenty bucks and bought one book, that doesn’t mean the others on the shelf weren’t worthy. Same thing applies for agents and publishers. Only instead of a few bucks and a few hours, you’re asking them to spend years working on your book and stake their livelihoods on its success.

I know you know this, but a “no” doesn’t mean your book isn’t good—it means you haven’t found the right match yet. And worst case, if your book isn’t good (read my story on that under #3), that doesn’t mean the next one won’t sell. MOST successful authors have been rejected before ultimately finding success.

So what should you do if you get rejected? Good question. Here’s a post I wrote about what to do when you do get rejected. It’s not what you think!

5. You’ll find out who your real friends are.

A lot of writers secretly believe that publication will be the moment everything changes. That the people who doubted you will finally take you seriously. That your ex will come crawling back. That your parents will apologize. That your kids will admit you were right about everything.

I hate to burst that bubble. But here’s what actually happens.

Some people won’t notice or care. Others will surprise you by cheering you on, even if you haven’t talked since middle school. Some will cozy up with new interest, and it’ll become glaringly obvious they were never real friends. And yes, some people you thought were solid will say something snarky or ghost you altogether out of jealousy.

But there’s also a beautiful clarity. The people who treat you just the same as always? The ones who were in your corner whether you were published or not? Those are your people. Cherish them.

Final thoughts I’m not proud of every mistake I’ve made, but I am proud that I kept going. As the saying goes, if you’re not a little embarrassed by your past self (and writing), you’re probably not growing.

Writing isn’t easy, but it’s worth it. And the truth is, the more you do it, the more you learn. So keep showing up. Keep learning. And know that you’re not alone.

You’ve got this. And I’m cheering for you.

 

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