There was a time I made a big leap “out the window.” I walked away from something I thought I had to escape. I didn’t have a detailed plan, just a deep sense that staying where I was would burn me out.
What I should have realized at the time was that while I was escaping one fire, I was just trading for another.
That’s the thing about decisions. They rarely come with clarity. They come wrapped in burdens and hope and urgency, all dressed up to look like certainty. But certainty is often just a story we tell ourselves to keep moving.
I’ve gone back and questioned plenty of decisions. I’ve hit pause, looked around, and asked, “Was that the right thing to do?”
Sometimes the answer is no. And that’s okay.
I’ve made wrong turns. I’ve said yes when I shouldn’t have. I’ve said no when I was afraid. But here’s something I’ve learned the hard way: wrong turns can still move us forward. Even the “mistakes” taught me something. Sometimes they were the only way I could learn the lessons I needed to learn.
Side note: If you can learn from watching someone else’s journey, that’s often preferable to taking the hard knocks that accompany most of the big lessons in life.
The truth is, not every decision will hold up to hindsight. And not every success will look like success right away. Some answers show themselves slowly. They show up only after struggle, reflection, and time. They need hardship to help them mature. Sometimes they even need failure.
I’m lucky. Along the way, there were people who didn’t try to fix me. They just stood with me while I figured it out. They gave me space to question, to re-route, to second guess. That kind of support is rare. And I’m grateful.
To those people: thank you. You helped me see what I wasn’t ready to see. You let me grow into the answers I didn’t even know I was seeking.
These days, I’ve learned to forgive myself for the detours. For the second thoughts. For the “what ifs” I’ll probably carry forever. I’ve changed my mind, more than once. With every shift, I’ve learned to find moments of peace.
Here’s the point: Maybe wandering is the way.
Wisdom doesn’t show up all at once. It grows, shifts, even contradicts itself. Sometimes it stumbles. Sometimes it starts over.
One thing I know for sure: What I thought I knew was only the beginning.
There’s a saying that often floats around in entrepreneurial circles: “Fail fast, fail often.” While the origins of this phrase are up for debate, its lesson is clear. Failure isn’t just an inevitable part of leadership. It’s one of the most defining. How a leader reacts to failure (their own or their team’s) can reveal their true character and shape the trajectory of their future success.
But here’s the thing: writing about failure and leadership can quickly sound like a series of cliches. We’ve all heard the platitudes about “learning from mistakes” and “rising stronger.” But there’s a deeper message about what truly separates those who lead with integrity and vision from those who crumble when things go wrong.
When failure strikes, leaders face a choice. They can own it, adapt, and come back stronger. Or they can point fingers, wallow in resentment, and stall out. The decision often happens in an instant, but its impact can last a lifetime.
Great leaders take ownership of failure, even when it’s not entirely their fault. Why? Because owning failure builds trust. When a leader says, “This didn’t go as planned, let’s discuss what we’ll do to fix it,” they inspire confidence. They create a culture where the team feels safe to take risks, knowing that mistakes are part of growth, not reasons for punishment.
When leaders blame others, they erode trust. Pointing fingers, whether at the team, external circumstances, or bad luck, signals an unwillingness to reflect and adapt. Over time, this creates a toxic environment where innovation dies and progress stalls.
“Fail fast, fail often” isn’t about being reckless. It’s about embracing experimentation and accepting that not every idea will succeed. Failing quickly means you can pivot sooner, learn faster, and ultimately get to a better solution.
This idea requires two things:
Humility: The willingness to admit when something isn’t working.
Agility: The ability to adapt and try again without becoming paralyzed by setbacks.
Elon Musk is a great example. From continual iterations of experimentation and failure at SpaceX—including multiple RUDs (rapid unscheduled disassembly in rocket speak)—to the challenges Tesla faced in scaling production and support, he’s built companies on the idea of learning through failure. Musk doesn’t see failure as an end point. He sees it as feedback. A necessary step on the path to success.
To handle failure effectively, leaders need more than optimism. They need a process. Here’s a simple approach that works (notice I didn’t say it’s an easy approach):
-Recognize the failure and what it means. Be transparent with your team.
-Reflect on what went wrong without assigning blame. Focus on systems and strategies, not personal shortcomings.
-Identify key takeaways. What worked? What didn’t? What’s worth trying again?
-Adjust your approach based on lessons learned.
-Recommit to the goal with a renewed focus and determination.
Failure doesn’t only teach leaders how to solve problems. It shapes their emotional intelligence (if they allow it). Leaders who’ve faced setbacks tend to have more empathy and patience. They’ve had to overcome multiple failures themselves, so they know how challenging failures can be for their teams.
When leaders normalize failure, they create cultures where people aren’t afraid to take risks or push boundaries. That’s where breakthroughs happen.
The mark of a true leader isn’t perfection. It’s how they handle failure. Whether they embrace it as a teacher or fear it as an enemy. The choice of owning mistakes, adapting, and persevering defines not just their success, but the success of everyone they lead.
The next time failure arises, ask yourself: Will I let this moment shape me for the better? Will I lead my team through it with grace and determination? Will we learn from this failure?
The answers will set the course for everything that follows.
The Hawthorne Effect refers to a psychological phenomenon where humans modify their behavior in response to being observed or studied. This effect was first observed in the 1920s and 30s during a series of studies conducted at the Western Electric Hawthorne Works in Chicago, hence the name.
The studies were designed to investigate the relationship between lighting conditions and worker productivity. But researchers found that regardless of changes in lighting, workers’ productivity improved when they knew they were being observed. This meant that the mere act of being the subject of an experiment or receiving attention could influence individuals to perform better.
It also means this powerful personal growth tool is available to you. It turns out that you are the observer you’ve been waiting for, the catalyst for your own transformation.
“You can’t learn to swim by reading a book about swimming. You have to get in the water.” – Unknown
The Burpee Quest
Funny thing about burpees: watching someone do a burpee makes it look super easy (barely an inconvenience). If a Crossfit guy tells you that a good warmup is 10 burpees per minute for 10 minutes, you might think that’s totally doable…until you try it. You’ll learn about muscles you haven’t used in years. You’ll be reminded that gravity is not your friend, and that you’re not as coordinated as you thought.
What if you start by doing 10? Not 10 per minute for 10 minutes. Just 10. Each day.
That’s a tangible and doable goal to start. You can observe (there’s that word) your progress and set incremental milestones for more. Maybe you move up to 20 per day the second week, 40 per day the third week.
A great way to keep track of your progress is to track your progress. Sounds simple…but most people skip the tracking. Tracking is your way to observe (there’s it is) your progress, and lets you become your own motivating force. Write the date and burpee count down on a piece of paper, in your favorite journaling app, or maybe in an Excel spreadsheet.
You are incrementally moving toward 100 burpees in a day. You’re tracking your progress and will start to see the significance of each step toward your goal.
There’s something else you can observe (that word again). Your body’s responses while you’re doing the exercise. It will get easier as you go. Easy? No, just easier. Your body (and mind) will begin to move to a higher level of performance. Your baseline capability will increase. Gravity still isn’t your friend, but you’re starting to learn how to partner with gravity to do the next burpee.
“Learning without reflection is a waste. Reflection without learning is dangerous.” – Confucius
It’s been 4 or 5 weeks since you started this quest. You’re now able to do 3 sets of 25 burpees each day. You haven’t reached 100 burpees yet, but you’re well on your way. If you’re like most people, you might observe (there it is) that you can lighten up a bit at this point. You’ve totally got this. You don’t need to push as hard to improve from here. Your goal is in sight. Don’t fall into this trap!
This is the moment to refocus your goal…push it out a bit…extend the finish line. You’ve already mastered the movements, now you need to apply discipline and blow past your original goal of 100 burpees per day. Parlay this achievement into the next goal?
Maybe actually using the 100 burpees as the warmup that Crossfit guy described. You’ve been working on just getting to 100 burpees in a day, but what’s the next exercise you can do after your burpee warmup?
Same process. Take it in increments, track your progress, celebrate your milestones, welcome to another new baseline, continue to improve, set the next goal.
How can you apply this to your profession?
Actively seek opportunities to acquire new skills. Embrace the awkwardness of not knowing exactly how to do something…and do it anyway. Remember that the satisfaction of learning and growth is uniquely yours. You, as the observer, choose the path of continuous learning. It’s the best way (the only way) to adapt to the evolving demands of your profession.
Improve your value in increments, track your progress, establish new baselines, continue to improve. Sound familiar?
Solicit constructive feedback from colleagues and mentors, appreciating external input as valuable guidance. However, remember that you are the only one who can internalize and implement these insights. Nobody will do it for you.
“Experience is a hard teacher because she gives the test first, the lesson afterward.” – Vernon Law
Your Keys to Self-Improvement
Consistently integrate self-observation and improvement into your routine, recognizing that only you can chart the course of your personal growth.
Reflect on your experiences, setbacks, and successes, understanding that the satisfaction of improvement is a personal journey. You are the sole interpreter of your progress.
Remain flexible and open-minded, adjusting your methods based on feedback and new insights. As the observer, you continually determine refinements to your approach.
Embrace setbacks as opportunities for growth, understanding that the satisfaction derived from overcoming challenges is a deeply personal experience. Stay committed to your objectives, recognizing that only you can appreciate the significance of your efforts.
The Hawthorne Effect is your friend (unlike gravity). Use it and always remember that you are the observer, the driver, and the one who benefits most from your continuous improvement journey.
Grandpa Bob Encouraging Leadership 
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