It was 4:27 AM, and I woke up without an alarm.

Not because I’m some alpha warrior bro with an optimized morning routine for ultimate productivity.

It was because of anxiety – something I had been dealing with unknowingly for a large chunk of my life.

Eighteen months ago, I was struggling to find the throughline for the book I was writing. I kind of knew what I was trying to do with it:

I wanted to help people figure out what to do after failing at something.

I knew that amidst the 120,000 words of chaos, there were 75,000 words that would make for a great book. But I couldn’t decide what could be cut, what needed to be changed, and which order all of those things went in.

My anxiety had me spiraling. I felt overwhelmed and lost.

So I asked myself one question, and that question made all the difference.

Before we get to my question, we need to make a quick philosophical detour.

(This is what we in the biz call a “cliffhanger.”)

“What is your life task?”

I later learned my question accidentally and perfectly embodied psychologist Carl Jung’s advice for navigating difficult choices in life.

As author Oliver Burkeman explains in Meditations for Mortals, the concept of a “Life Task” is a different question that “What do I want to do?” or “What would make me happy?”

Those are questions we ask when we are probably avoid the hard questions that will actually help us live a life true to ourselves.

Burkeman explains there are two rules to a Jung’s “Life Task.”

RULE ONE: “A life task will be something you can do ‘only by effort and with difficulty,’ as Jung puts it – and specifically with that feeling of ‘good difficulty’ that comes from pushing back against your long-established preference for comfort and security.”

RULE TWO: “A life task, though it might be difficult, will be something you can do… This helps distinguish the idea of a life task from certain popular notions of ‘destiny’ or ‘calling,’ which can leave people feeling as though there’s something they’re meant to be doing with their lives, but that their life circumstances make it impossible.”

In other words, a life task is “what’s being asked of you, with your particular skills, resources and personality traits, in the place where you actually find yourself.”

When we feel overwhelmed, when we’re not sure what we should do next, asking “What’s my life task right now?” might reveal the deep-down answer, the clarifying answer, and the next step on our life’s path. One we’ve probably known all along, we just had to ask the right question to find it.

“Does this help the reader try again?”

Which brings me to my question I asked myself.

The working title for my book was “Restart,” but I didn’t think that fully conveyed how I was trying to help people.

It wasn’t just about restarting after a failure, or making a change.

It’s a book that teaches somebody HOW to try again so that they didn’t fail the same way again.

It’s a book about navigating a chaotic existence, and learning how to stay afloat when life doesn’t go according to plan.

(I had a pretty rough 2024, so I ended up writing the book I needed to read myself).

This is right around the time a more fitting title for my book popped into my head: “How to Try Again.”

So I grabbed an index card and wrote a clarifying question:

“Does this help the reader try again?”

I put this notecard next to my computer every day for the next year.

That became my Life Task: to finish a book that helps the reader try again.

A life task that was very difficult and something I could do.

Suddenly, the paralyzing decision of what to keep and cut got easier. I chopped out tens of thousands of words. Not because they weren’t great stories, but because they didn’t “help the reader try again.” If the story/lesson helped the reader try again, it stayed. If it didn’t, it had to go.

(I have a hunch some of these stories will make their way into future books).

Of course, this simple question didn’t solve ALL my problems.

Life is hard and writing a book is very challenging. It took another twelve months of hard work, guidance from friends and my editor, and another 10 drafts:

But that was the task life asked of me:

“Finish your book to help people try again.”

By accepting my life’s task, by asking the right question, I stopped existing in existential, anxious paralysis, and got to work each day on helping my future reader try again.

What is your life task right now?

Now that my book is turned in, I’ve embarked on a new Life Task.

I’ve lived a pretty absurd life up until now.

19 years ago, I said to my boss at my old company “We should have a podcast!” and two weeks later I found myself interviewing Zac Brown, Brandi Carlile, and Hanson while floating through the Caribbean.

15 years ago, I booked an absurd flight around the world for $419 and turned my life into a video game for 18 months:

10 years ago, I moved to NYC (here is my artist rendition of my move, no AI needed):

After a few years of hibernating and shrinking, and then a few years to get this boAfter moving back to Nashville, and spending a few years of hibernating and retreating, I dedicated the last 3 years to finish my book.

Life is now asking me a different task: to get back to living an interesting life.

As an quasi-introverted writer, hopelessly addicted to the internet even though it’s detrimental to my mental health, and a massive fan of epic video games, I have to challenge myself to get out into the world.

It’s why I’ve written recently about making stuff with my hands again, focusing on the “real-world” instead of diving deeper into algorithms and AI.

My writing (and my mental health) is better when I get out of my house and go do stuff.

My favorite stories in How to Try Again are the ones that came from boots-on-the-ground research, conversations with real people, and insights I noticed while doing interesting things.

It also means I’m starting to rev up my travel muscles again.

I attended a conference last week in Atlanta, I’m headed to Craft + Commerce in Boise in June, and I have a fun trip to the UK planned this summer.

There’s now a new index card that resides next to my computer and in my journal:

“Does this help me live an interesting life?”

This doesn’t mean I’m must shirk all responsibility and go full YOLO, nor does it mean I won’t allow myself to slow down or relax (rest is key!).

This card is a nudge to get off social media, put down my phone, not crazy hours, and go have a more adventures outside of my hobbit hole.

I can then come back and write about those things! Or not! But the task is to go live a life true to myself and this task.

Your turn: What is life tasking you with right now?

Is there a question you can ask yourself to help you make decisions?

RULE ONE: It’s something you can do “only by effort and with difficulty.”

RULE TWO: It’s something you can do now.

It doesn’t have to be grandiose, nor epic, nor adventurous. Maybe Life is tasking you with something different right now. I love that for us.

Feel free to ​comment on Substack​ with your current Life’s Task/Question, or hit reply, I read every email!

How to Try Again Corner – Goodreads and Libraries!

We’re less than 2 months away from How to Try Again hitting shelves.

For the 1000+ legends who have already preordered the book, you have my eternal gratitude.

(And last time I checked, “eternal” is a long time!)

If you haven’t pre-ordered yet, I promise this will be the best $25 you spend this year.

Now, you might be saying:

“Steve, you seem like a weird dude and I like the cut of your jib. But I can’t pre-order the book right now, how else can I support you?”

Great question, and thank you. I like the cut of your jib as well.

Here’s two things you can do:

1) On Goodreads, Add my book to your “Wishlist!” (or on StoryGraph!) This helps other readers, my publisher, Amazon, and other book stores know which books are worth checking out.

2) Request the book at your local library! Almost all libraries have a way of requesting books too! Visit your library’s website and let them know you’d love to read How to Try Again! This way, you get to read it, and then other people can read it after you. Everybody wins!

Thanks, now it’s time to get back to work on my life task!

Let’s see how we can do some interesting stuff today.

-Steve

PS: Feel free to comment on this post over Substack if you use that platform.