I’m Hoping You Can Learn from My Mistakes

I turned 38 years-old today. Looking back on a myriad of past mistakes and bad decisions, here’s my birthday present to anyone interested — 38 lessons that I wish I’d learned much earlier in life.

  1. We almost always know what we should…


We All Adopt the Behaviors of Those Around Us

“If you consort with someone covered in dirt you can hardly avoid getting a little grimy yourself,” said the Stoic philosopher Epictetus. …


The World Needs Leaders More Than It Needs Managers

“A real leader,” David Foster Wallace wrote, “can somehow get us to do certain things that deep down we think are good and want to be able to do but usually can’t get ourselves to do on our own.” There are…


And What to Do About It.

When my friend started her new job, she got along well with her boss. They met frequently so that he could offer support and encouragement. He was patient and understanding as she learned the company.

As she became more effective, however, their relationship began…


Your Team Needs a Leader, not a Friend.

When I first became a manager, I tried to be everyone’s friend. I wanted everyone to like me. I wanted people to look forward to their time at work. I wanted to be the cool boss.

It worked, at least at first…


“It’s not what you preach, it’s what you tolerate,” wrote Navy Seals Jocko Willink and Leif Babin on maintaining standards as a leader. This same principle extends to all aspects of life. With every interaction, you teach people how you want to be treated. …


3 Steps to Use it to Your Advantage

“I need you to be more strategic,” my manager told me. Then he sat back in his chair, letting me ponder the depths of this insight. Doubtless, he thought it was helpful. Yet I had no idea what to do with it.


The Great Resignation is an Opportunity, Not a Threat

“When people are financially invested, they want a return. When people are emotionally invested, they want to contribute,” said Simon Sinek. When people are engaged with their work, they’re committed to the organization. When they’re not, they’re not. It’s not complicated…


Managers need to remember one thing above all else: they don’t do the work. Their employees do. A manager’s job is to help them do it easier and better.

It’s easy to forget this. It’s easy for managers to start believing that their employees are there…


The Key to Regaining Control is Not Making Things Worse

“Life has many ways of testing a person’s will, either by having nothing happen at all or by having everything happen all at once,” said Paulo Coehlo, although between his two scenarios, it seems that everything happening all at once…

Jake Wilder

Writing helps me realize just how little I know.

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