Failing Forward: What to Do When Things Don't Go as Planned

Kristen Ann
May 24
5 min read

There's a phrase I come back to often in my coaching work — with executives navigating career transitions, leaders sitting with a decision that didn't land the way they expected, professionals questioning whether a setback means something about who they are.

The phrase is failing forward.

It's not mine. It belongs to John C. Maxwell, who first introduced it in his book Sometimes You Win, Sometimes You Learn and expanded the idea in Failing Forward: Turning Mistakes Into Stepping Stones for Success — it gets at something most of us resist: that our losses often teach us more than our wins ever could.

The concept only works if you're willing to do something with it.

Why We Get Stuck

Most of us were taught — either explicitly or by example — that failure is something to avoid, hide, or overcome as quickly as possible. So when it happens, our natural response is one of three things: we freeze, we deflect, or we rush past it without really looking at it.

None of those responses get us anywhere useful.

Failing forward is a different posture entirely. It's the decision to stay in relationship with what happened long enough to understand it — and then use it. Not as a story you carry around, but as information that actually changes how you lead, decide, and show up next time.

The Framework: Four Moves Toward Failing Forward

1. Redefine What Failure Means

Maxwell's central argument is simple: the difference between people who achieve and people who stagnate isn't the number of failures they have — it's what they believe failure means.

If failure means I am not enough, you'll do everything possible to avoid it. If failure means I'm getting closer, you'll stay in the game.

The work here is honest and often uncomfortable. It means examining the story you've been telling yourself about what went wrong — and asking whether that story is actually true, or whether it's just the most convenient one.

"Fail early, fail often, but always fail forward." — John C. Maxwell

Watch: John Maxwell — Failing Forward (Inspirational Video)

2. Face It Without Flinching

This is the step most people skip.

When something doesn't go the way we planned, the temptation is to minimize it ("it wasn't that big of a deal"), catastrophize it ("this changes everything"), or intellectualize it ("here's what went wrong, moving on"). All of those responses have one thing in common — they keep you at a distance from the actual experience.

Facing failure honestly means sitting with what happened, naming it specifically, and resisting the urge to wrap it up in a bow before you've actually learned anything from it.

It also means acknowledging the emotional weight. Failure can bring up shame, grief, self-doubt. Those responses are human. The goal isn't to not have them — the goal is to not let them make all your decisions.

Watch: 5 Rules from Failing Forward — John Maxwell (Short)

3. Extract the Learning Deliberately

This is where failing forward separates from just failing.

Learning from failure doesn't happen automatically. Left unexamined, a setback just becomes part of your scar tissue — something you carry without knowing why. Deliberate learning requires intention: setting aside time, asking good questions, and being willing to hear uncomfortable answers.

Maxwell outlines this clearly in Sometimes You Win, Sometimes You Learn — the losses in our lives contain eleven specific elements of learning if we're willing to look for them. At the core of all of them is a single question: What does this teach me that I couldn't have learned any other way?

That's the question worth sitting with.

Watch: Failing Forward — 5 Key Points, Animated Audiobook Summary

4. Adjust and Move — With What You Now Know

The final move is the one that makes failing forward actual. It's not enough to reframe, face, and learn — you have to do something different as a result.

This doesn't have to be dramatic. Sometimes the adjustment is subtle: a different question you ask before making a decision, a conversation you now know not to avoid, a strength you learned you have under pressure. What matters is that the failure left you with something you didn't have before — and you're actually using it.

Actions to Try

These aren't exercises for their own sake — they're practices that help the framework actually land.

After a setback, write it down. Get specific about what happened, what your role in it was, and what surprised you. Writing slows down the rush to resolution and gives you something to return to.

Name the loss. Was it a lost opportunity? A relationship that shifted? A version of yourself you thought you were? Naming the actual loss matters — it's more honest than "it didn't work out."

Find one person to process it with. Not to vent, but to think out loud with someone who will ask good questions rather than offer quick reassurance. Maxwell says it directly: failing alone is hard enough — processing that failure alone makes it harder.

Ask: What did I assume that turned out to be wrong? Most setbacks reveal a gap between what we believed and what was actually true. Finding that gap is where the real learning lives.

Give yourself a 48-hour rule. Don't make any major decisions in the immediate wake of a significant failure. Give yourself 48 hours before you decide what it means and what to do next.

Reflection Questions

Use these on your own, with a coach, or as a journaling prompt in the days after something doesn't go as planned.

What story am I currently telling myself about what happened? Is that story helping me or keeping me stuck?
What did I do well — even in this setback? What does that tell me about my strengths?
What would I do differently, knowing what I know now?
What did I learn about myself under pressure?
What would I tell someone I care about if they were in this exact situation?
What's the next right step — not the whole plan, just the next step?
If this failure is trying to teach me something I needed to learn, what might that be?

A Word on Timing

One thing worth saying: failing forward is not a demand to move on quickly. Some setbacks need time. Some losses need to be grieved before they can be learned from.

The goal isn't to skip the hard part. It's to eventually — on your own timeline — turn toward the experience rather than away from it. That turn is the work. And it's worth doing.