The Purposeful Leader

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Marketable: the 3 Skills we Actually Need

Leadership, Management, Values

Have you heard of the Stockdale Paradox? It’s the idea that in order to succeed at achieving anything (in Stockdale’s case, living through being a prisoner of war), you have to simultaneously 1) 100% believe that you’ll succeed and 2) realistically look at the facts in front of you.

Or, to quote Stockdale directly, “You must never confuse faith that you will prevail in the end — which you can never afford to lose — with the discipline to confront the most brutal facts of your current reality, whatever they might be.”

Stockdale’s experience as a POW showed him that those who survived kept faith while also facing reality. He observed that those who kept faith without reality (“we’ll absolutely be out of here by Christmas” . . . “maybe Easter”) didn’t survive. Their faith wasn’t balanced, and it only served to set them up for disappointment, which in those particular circumstances, had devastating implications.

I would have died.

A previous version of me would have, anyway.

I love thinking about possibility, about the future. I love feeling excited about what’s to come. Dreaming big.

And so many times over my career, I can look back and see how this skill helped me immeasurably.

But what’s also true is that I’ve often been more excited about the vision than the full reality of execution. In for the inspiration, mixed about the perspiration.

I wasn’t aware this was happening. I worked very hard. But I was holding myself back, and holding my team back as a result.

There were different brutal facts in different circumstances, but the common denominator was that I wasn’t willing to look at the brutal facts because acting on them would have been uncomfortable.

We often think and act based on what “feels right.” Which means that if facing the facts puts us in uncomfortable territory . . . why not stay in fantasyland? It’s easy to stay in a place of hopeful optimism because it requires no discomfort.

A sign that you might be avoiding reality is that your plan of attack includes “hope” as a strategy. Saying that we’re “hoping for the best” isn’t a plan. It’s not a step toward a goal. It’s not even our best guess about how to get there.

When we think about what’s between us and a goal or a challenge, we tend to think in either fluffy, hopeful aspiration or concrete technical skill. But I think there are 3 mental shifts/practical skills that keep us facing reality, and change everything about our experience and our contribution.

If we invested in teaching these skills to every person, and if we as leaders did our level best demonstrating them every day, I can’t even imagine the possibilities.

A real, gritty commitment to growth.

Not in-theory growth. Commitment to growth over comfort. Seeing an opportunity for growth and heading straight for it. Making growth the highest priority.

Not growth generally — it’s not about attending conferences and learning more. Sometimes growth is about un-learning.

It’s about what feels hard for you, specifically.

If it’s impossible to imagine a week of committing to your calendar but you know that you’d learn something powerful by doing it, that’s your growth. I’ve worked with clients whose specific growth was not attending events and conferences, staying present with their teams for a full month. At the time, the very idea felt excruciating. And it what it taught them was immeasurable.

Where are you avoiding, confused, or telling yourself something “just isn’t going to be your forte”? That’s what’s going to teach you the most because that’s what’s limiting your sense of what’s possible right now.

Growth is about teaching yourself over and over and over again that impossible is temporary. It’s about ending your day knowing that you did hard things and not only survived but are more proud and satisfied than you can imagine.

Pushing ourselves outside our comfort zones — look, I know it’s a cliche, but it’s exactly what I mean — is what shows us that we always keep our comfort zones smaller than what we’re really capable of. That they grow every time we push their boundaries. Without much resistance, actually.

Embracing Failure + Rejection

I want you to imagine that your job is to fail 20 times each day. Not fake fail. Not try something safe but foolish on purpose because you know there won’t be a consequence. Not fail ahead of time by not trying. But fail. Try something, put your best work forward, and have it flop.

In this scenario, your salary + bonus are determined by how often you fail. 

And in fact, if you exceed 20 fails each day, you can retire early.

Now imagine how much more you’d know after a week in this reality than in a month of not failing.

We see phrases like “fail forward” everywhere. And I know, even when I worked in the world of innovation education, where there is more positive failure talk than perhaps anywhere, I didn’t get that it’s not just about failing well, it’s about failing on purpose. It’s about trying enough, trying big enough, that you will inevitably fail.

Because only when we’re committed to that can we transform our mindset about failure in a way that serves our growth. Only when failure is welcome can you think about it not as “something to bounce back from” but as an inevitable part of the path. You don’t take a dip when you fail, it’s not a step back. It’s a step forward.

Decision Making

Similar to the failure reality above, imagine how much you would learn if, after you had all the data needed to make a decision, you only had 30 seconds to make it. Every time. Imagine that you couldn’t sleep on it, deliberate, phone a friend. You just had to determine how you were going to make it, and then decide.

At the end of a year, here’s what you’d have:

  • Exponentially more decisions made.
  • Unquantifiable growth and learning.
  • Much more trust in your ability to make decisions, and a solid belief in your ability to make “right” decisions through committing to the work you’ve done to support the decisions you’ve made.

And here’s what you wouldn’t have:

  • Hemming and hawing and wondering.
  • Wasted time.
  • A vocabulary that included the phrase “I don’t know” for anything other than Trivial Pursuit.

Our brains are negativity factories. When we leave them with a decision, they will give us fear, encourage doing what is “safe” and tell us we don’t know over and over and over again. If we want to move forward, we have to stop handing decisions over to the possibility-dismantling-line. When we “sleep on it” we’re so much more likely to make overly cautious decisions that keep us in the same place we already are. Making quick decisions often is what takes us to a different future.


To pull all of these skills together, let’s use the example of an executive director who wants to raise $10MM for her organization. She’s never raised that kind of money before.

Following the growth, failure, quick decision model, if she heads straight for the goal, she’s going to feel uncomfortable, fail a lot, and make decisions before she feels “ready.”

But she’ll design a plan aimed at securing the goal, not avoiding failure. She’ll expect failure, she’ll make decisions and act on them. And she’ll adjust the plan as she learns, but won’t change the goal. She’ll stay committed to the goal because the goal is her growth.

What happens? What’s her result? She has given herself a skill set that no one can take away. She knows how to raise $10MM. And that means she could do it again. Better this time, faster.

Imagine for a moment what it would look like to put these things into practice — for yourself, for your team, for your company, or for your family. What would be different after three months? A year? A decade?

We spend a lot of time in the blue sky of values and guiding principles. And they’re often aspirational or ambiguous. Executing + operationalizing them leaves room for interpretation. I’ve worked at companies that were exceptional at living their values, and there was still inconsistent execution.

We also spend time thinking about hard skills, and training and teaching ourselves and our teams the “how” of achieving a goal. We want a precise roadmap.

What I love about gritty growth, failure and quick decision making is that they keep us out of the blue sky because they’re uncomfortable for most of us. And a team united in an understanding that their discomfort is the currency of success? I think they’d be unstoppable.

Because a roadmap is a terrible analogy for achieving any goal. There is no goal that has ever been achieved by mapping something out in advance and following that original plan precisely without adaptation. We can sketch a possible route, sure, but getting there requires flat tires, unexpected roadside attractions, inclement weather, parade delays, and many more unforeseen factors. The map might be helpful, but what’s going to get us to our destination in one piece, on time and happy is our ingenuity, attitude + flexibility. It’s our ability to deal with what we can’t predict with grace and keep going.

Going back to where we started, the Stockdale Paradox, not facing reality seems perfectly reasonable in the face of a truth we’d rather not look at. But looking reality in the face is always more powerful than keeping it in our peripheral vision. In front of us, we see it clearly, right-sized. And the more we stare at it, the less scary it becomes.


Going after your growth, failing on purpose and making frequent fast decisions isn’t easy — but it’s also the path to more joy, satisfaction, and engagement. When we sign up for fully experiencing, we get to more fully experience everything. If you’re ready, sign up for a free coaching consultation. Make a quick decision, in the direction of your growth. The only possibility of failure is not showing up.