The leaders I respect most are the ones who have real stories of learning and hardship—stories that help me avoid making the same mistakes in the future.

Charlie Munger gave a famous speech called “How to Guarantee a Life of Misery,” where he outlined three surefire ways to ensure unhappiness:

1. Be unreliable.

2. Only learn from your own experiences, rather than from the good and bad experiences of others, both living and dead.

3. If you go down, stay down. Everyone will face adversity, but only those who rise again avoid permanent misery.

When I think about leadership, especially when navigating ambiguity, my version of Munger’s speech would be “How to Make Your Team Miserable.” This is especially true when leading through uncertainty.

Here’s a story about the misery I created—and the time in my career when I was the worst leader.It was 2011. We were building a local services marketplace called Zaarly. We had raised over $40 million in venture funding, but the product wasn’t working. I was the head of product.

I’ll never forget the question from our best engineer: “Why do you keep saying everything is great?”

Leading through ambiguity should really be called leading with insecurity.
I said everything was “great” because I was terrified to admit it wasn’t. I didn’t even want to acknowledge it myself, and for a while, I didn’t. Eventually, I learned that denial actually stands for “Don’t Even Know I Am Lying.” I didn’t want to lie, but I was too scared to tell the truth.

I was young, passionate, and inexperienced. The product wasn’t working. User numbers were dropping, engagement was declining, and no one loved what we were building. Our strategy was wrong.

But I was too scared to say that out loud. Instead of confronting the reality, I tried to keep everyone positive, protect the team from the truth, and fix everything myself behind the scenes. The secret is where great leaders fail.

Not speaking the hard truths to our team and hiding what I was afraid of, all under the guise of “protecting” them, is exactly how I made our team—and myself—miserable.

This is the greatest failure of leading through ambiguity—thinking you’re protecting your team by not telling them the hard truths.

If you want to be a bad leader, here’s how to do it:

1. Keep money a secret. I once thought hiding financials would protect my team. The truth? They already sense it. People are doing the math in their heads and talking about it. Be honest about the reality. It’s better for everyone to know the truth, especially if things are tight. They’ll appreciate your transparency and prepare for any downside.

2. Say everything’s great when it’s not. Pretending things are fine when they’re not is the worst thing you can do. People leave when they don’t feel you’re aware of the issues. Be honest, acknowledge the problems, and tie them back to the company’s mission. That’s what keeps people around.

3. Add more features before fixing the core issue. Adding features without fixing the ones that aren’t working is a quick route to mediocrity. Focus on solving the real problem, then move forward with new ideas, not just new features.

4. Sell people on how great the company is. Don’t sugarcoat things. Be honest about the hard work ahead and the challenges the team will face. People want to work on something meaningful, not a fantasy.

5. Hire more people to solve ambiguity. More people won’t fix the uncertainty. Instead, keep the team small, focused, and contextually aware. This will help identify problems and solutions faster.

6. Don’t ask questions. Leaders often feel they need to have all the answers. But asking the right questions is key. Instead of asking, “Does everyone agree?”, ask “How could this go wrong?” This opens the door to honest answers and helps avoid groupthink.

7. Lie to yourself. We all do it, but leaders especially. Saying things like “Everything’s fine” or “We can raise more money” isn’t helpful. Acknowledge the challenges and be real about the situation. Only then can you move forward with clarity.

These are the surest ways to make your team miserable. And yourself. Good luck leading through ambiguity and hopefully these can bring a little more clarity, honesty, and peace to your organization.