I think about failure a lot. But not in the way many of us have experienced that feeling before.

Sure, at one point (or even many points) in my life, the idea of failure was through the lens of the typical: work, money, family, creativity, etc.

I’m sure you have your own, maybe similar, list.

But over the years, and especially through this work, it’s been somewhat plain to see that most of the time when we’re afraid of failure, we’re actually afraid of something else entirely. Something deeper that we haven’t named yet.

For example, sure, I could lose clients. That’s a real possibility.

But what really keeps me up isn’t the money part. It’s the thought of becoming someone who goes through the motions, stops believing in the work, and ends up drawing for people I don’t respect just to pay the bills.

That’s not failure. That’s a fear of losing myself.

Once I started getting honest about what failure actually looks like for me, something interesting happened. The fear became less overwhelming and more, well, manageable.

Because there’s a chance many of us are thinking about failure all wrong. What if it’s not this big, scary thing we avoid talking about, but something we can actually plan for and then even prevent?

The Wrong Kind of Fear

Most people, when I ask them what failure looks like, give me the obvious stuff. “Getting replaced by AI.”

“Losing our biggest client.”

“Running out of cash.”

All valid concerns, but they’re surface-level. They’re the fears that feel safe to name because everyone has them.

The real failure, the kind that actually happens to people, is usually emotional or existential.

It’s becoming someone who’s tired of their own work, saying yes to clients you don’t believe in, slowly stopping to care about quality.

I’ve come to realize that its the fear beneath the surface that manifests in ways we don't expect. But getting honest with it, about what we’re actually afraid of, means we can do something useful with it.

Fronting Failure

That’s where pre-mortem comes in.What do I mean by this?

“Pre-mortem analysis” has become my favorite liberating structure, and honestly, it's been a game-changer for teams who are brave enough to try it.

Instead of starting with your goals and hoping for the best, you start with failure. You sit there and imagine it’s one year from now, and everything has gone wrong.

Your project flopped.

Your team is demoralized.

Your strategy completely and 100% backfired.

Now, reverse-engineer it. How did you get there? What decisions led to this potential outcome? What warning signs might you have ignored?

Working with teams and leaders, I’ve noticed these kinds of questions don’t get asked all that much.

Not "What are your growth goals?" but rather "What would it look like if you stopped believing in what you're selling?"

Instead of "How will you succeed?" it's "How will you know when you've lost your way?"

This is the power of a pre-mortem. It forces you to look those uncomfortable truths directly in the eye before they can even become problems. So many folks skip this step because it feels overly negative or pessimistic.

But pre-mortem analysis isn’t about being negative, it’s about reverse-engineering failure. Doing that means turning vague anxieties into specific, actionable warnings.

The Three-Question Framework

If you want to try this yourself, there are three questions I use. Fair warning: they’re not comfortable, but they work.

1. What would failure look like if your business crumbled this year? Not the obvious stuff like losing revenue. Dig deeper. Would it be that you compromised your values? That you became someone you don’t recognize?

2. What would failure look like if you gave up on your work entirely? This one hits differently. It’s not about business metrics. It’s about you as a person. Would failure be settling for work that bores you? Losing the spark that made you start?

3. What are you holding onto that needs to be let go? This is what I and others also call “murder your darlings.” The habits, clients, or strategies that feel safe but aren’t actually serving you.

I call the first question little "R" reflection, your business. The second is big "R" reflection, yourself. The third question is a combination of the two, little r big R. When you answer them honestly, the fear transforms into something actionable.

Instead of worrying about failure, you’re planning to prevent it.

From Fear to Clarity

Maybe failure isn’t this big, inevitable bogeyman we should dread. Maybe instead it’s just a state of mind looking to be conquered with the right tools.

Pre-mortem analysis turns anxiety into preparation. Instead of lying awake at 2 AM worried about the next thing that might go wrong, you’ve already thought it through. Or at minimum, you’ve thought through the act of thinking it through, preparing you for a wider range of outcomes.

You’ve named those real fears, planned around them (or with them in mind), and given yourself permission to let go of what’s not working.

It’s tough to do this kind of reflection alone. Sometimes you need someone from outside the circle to ask the questions you've been avoiding, to help you discover what’s maybe too close to notice. Who are the people who can help you figure this out?

The fears you're not naming are probably the ones worth facing. What are you worrying about?

And once you face those worries and prepare? They stop being fears and start being plans.

Grateful you are here,

Wade

PS - We've added a bunch of new quotes and images to our Draw for Hope store!

One of my favorites has to do with Joy and Gratitude. Check it out:

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