The best work of your life might be behind you

Why embracing both craftsmanship and artistry in writing can help you thrive, even if your best work might already be behind you.

Hi,

This is a thought experiment.

I'm 42, and have been involved in about 100 projects of different types during my career. If I have 100 projects left in me, then there's about a 50% chance that the best thing I've ever made has already been written. Similarly, there's a 50% chance that my best project is ahead of me.

So, what if my best work really is behind me?

Well, for one, I should certainly make sure to fully exploit my best work. I’m not talking about just selling a book in its native language, either. Once you have a winning story, you can translate it into other languages and mediums. Great stories traditionally don’t expire. Hollywood stakes billions annually on this truth, mining old successes and reimagining them in new formats. You can do the same with your work.

My most popular book has only been read tens of thousands of times in a world with billions of people in it. Even if it had been read by millions, there are still billions of people out there who haven't heard of it.

Yes, it’s true that once you’ve made something that stands the test of time, it tends to keep working, even as time marches forward. But beyond that, creating something excellent raises the floor of your future work. Your "worst" creation today is exponentially better than when you started years ago.

We often think in terms of “best”, but I think it’s more instructive to think in terms of “worst”. If you’re worst work is still readable and enjoyable to your fanbase, that’s when you have a career. If you don’t know how to repeat your success, then things are going to be hard until it clicks for you.

I talk to editors all the time and you might be surprised how much consistent quality plays into who they hire for a project. Most editors don’t care so much about the upside of a writer’s potential as much as they care about whether the work will be high enough quality, on time, and that the writer is easy to work with regarding edits.

When they acquire a finished piece, this is obviously less true because they can read it, but most editors mostly work on slates of IP and articles that need to be staffed quickly and efficiently every week, month, or year. They just want to know that if they send out an assignment it will come back without muss or fuss, which is why the quality of your worst work is so important.

As I’ve improved the floor of my work, the quality of my assignments has increased exponentially to match it. While my best work might be behind me, my worst project almost certainly happened long ago. My taste is much better today, and so is my skill level.

It is certainly possible that you never write a hit again, or you never write a "good" book again, but the more books you write, the less likely that is true, because the practice of writing improves your craft. Acknowledging uncertainty isn’t pessimism, it’s honesty. That said, true honesty means looking at both sides of that argument.

Yes, a bad book could happen and a career could end after a string of duds. However, either are unlikely, and more unlikely with each project you successfully complete.

Still, we must acknowledge that possibility in ourselves if we want to trust our instincts. I often consult with authors who try to gaslight themselves into believing a bad book could never happen or that a career can never end after a string of bad books. There is a non-zero chance of that, just like there is a non-zero chance I get attacked by a bear when I go to the mall.

How can we ever trust ourselves about anything if we lie to ourselves about the uncertainty of doing this work?

We are all entrepreneurs. Nothing is certain in entrepreneurship, but we keep going anyway, because it’s worth the suffering and uncertainty. The question you should ask yourself is what is worth doing anyway, given all the struggle? It is all hard; having a job, building a business, having a family, buying a house, writing a book. There are no easy paths to a “good” life.

We all, each of us, must choose our hard, every day in every way. If we choose to build our writing career, then it will be hard and there will be struggle. You might, even with extreme effort, fail at any moment in catastrophic and ruinous ways.

Given those possibilities, what can we do to mitigate those outcomes? First, we must have a process. Trusting the process is about trusting your process; the one that produces consistent results for you.

For me, after a book is done it gets read by my long time editor, my long time proofreader, and my wife. If those three people sign off on it, and I feel good about it, then it probably means it’s not going to destroy my career.

I can’t say how successful it will be, but my process is not built for that. It’s built to avoid catastrophic results. I trust those three people to approximate the taste of my audience. So, if they like it, my audience will probably like it, too, or at least not hate it.

Writing is my craft, just like the craft a potter uses to make every bowl. Writers, at their core, are every bit the craftsman and artisans as blacksmiths and woodworkers and cheesemakers who all have a process they fall back on that delivers consistent results every time.

Do craftsmen and artisans make mistakes? Absolutely, but they’ve mastered the art of recovering and adapting, transforming errors into opportunities for improvement. True expertise lies in the ability to turn mistakes into happy accidents, and those accidents into remarkable successes, without anybody being the wiser.

Not every story will be great, but we can mold it into something great, or at least usable, using our skill and craft. Even if we can’t make it great, we can almost certainly salvage it into something that’s not embarrassing for people to read.

It is a beautiful thing to be a craftsman, but it is very different from being an artisan. A craftsman masters every step of the process. Then, they use that process to make the same things repeatedly without much deviation between them. I’ve visited craftsman on my travel that have made the same thing following the same process for 40+ years, and it is magical to watch.

This is wondrous and awe-inspiring, but is it the core of art? I certainly think it's a type of art, but it's different than the process of bespoke artisanship.

The older I get, the more I believe that art is the process of exploring the unknown. There is greatness in craft, practice, intention, and process, but the art of it is going into the depth of darkness and pulling something new that you’ve never seen before out of it, even when you don't know what is going to happen.

An artisan combines their mastery of familiar techniques with the boldness to explore uncharted methods, venturing beyond what they already know. While they draw on established skills, they also experiment with new, untested approaches, unsure of how they will blend. From this process of exploration and risk, something magical emerges that is greater than the sum of its parts.

How can this distinction help build your writing career? Because you get to choose your hard between these two difficult paths. If you want to increase the chances you will have the same level of success, then maybe you should spend some time as a craftsman, writing a series with the same structure every book with known outcomes you have already mastered. I spend a lot of time as a craftsman, and I love it.

There is great joy in focusing on making the best work I can given known constraints. You probably will never make a book much better than the first time you wrote a book in that series, but as long as you follow the rules you've set, your chance of failure is much smaller.

If you want to uplevel yourself, on the other hand, or are just itching to try something else, it might be time to embrace your inner artisan, use your existing skills to dive into the unknown, and to create something new that will uplevel you into something wholly unknown. The chance of making your "best" work is higher as an artisan, but your odds of making a mess are much higher, too.

Some writers spend their whole career as artisans, making new, weird things until that becomes their brand. Others spend all their career as a craftsman, folding and refolding the same tropes and stories in magically perfect new ways.

Most of us float between the two through a permeable, invisible membrane without even noticing it.

By simply taking the time to acknowledge what side of the divide we find ourselves on, and aligning it with which side we want to be on, we can create more intention in our process.

When I want to jump to the “next level”, I tend to embrace my inner artisan, but when I’m trying to establish myself as an expert in something, I usually embrace my inner craftsman.

Be aware, very few people are likely to follow you from one level to the next, and it’s scary to leave all you’ve ever known, but it will also lead to returns you can’t imagine.

Whether you have written the best work of your life or not, the true beauty of it all is the journey, and choosing to go back into the breach anyway, even if you don't know what's going to happen.

What do you think?

• How do you balance the roles of craftsman and artisan in your creative process, and which approach has been more rewarding for you?

• Do you believe the joy of creating lies in the outcome or the process, and how does that perspective shape your approach to uncertainty in your work?

Let us know in the comments.

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