School is largely a collection of easy lessons. How to read. How to add. How to reason. Even becoming a doctor or an engineer is filled with lots of safety nets—residency, reviews, tests and trials. You can learn how to build a bridge without one collapsing. You can learn how to perform an appendectomy without killing someone. Easy lessons are the ones where the stakes of failure don’t affect your ability to learn them. But not every lesson in life is easy. James 3:2 reminds us, “For we all stumble in many ways. And if anyone does not stumble in what he says, he is a perfect man, able also to bridle his whole body.”
A man’s character is built not on easy lessons, but on difficult challenges. The hard lessons in life and work are the ones that mold us into savvy and discerning men. Marketing author Ryan Holiday, a proponent of stoic philosophy, wrote, “Like any good school, learning from failure isn’t free. The tuition is paid in discomfort or loss and having to start over.” The hard lessons are generally the ones that are outside the classroom. They’re the ones we learn from relationships, failures, or testing our moral limits. Here are three lessons you may indeed learn “the hard way”:
Not all friends are true. The relationships we form are crucial to life and leadership. Trusting the wrong people can lead to betrayal or heartbreak. The people you know well, and with whom you share confidential information and from whom you seek advice, should be vetted in the most traditional sense, and that is through time-testing and crisis-testing. The Bible teaches, “A friend loves at all times, and a brother (or sister) is born for adversity” (Proverbs 17:17). You can tell a real friend because they stick with you through difficulties, and still connect and care for you when you are at your worst.
A tough lesson to learn in life is that not everyone who says they are your friend truly is your friend. Every leader can think of one or more people who left them when times got tough, or who betrayed their confidence and trust, or who put their own self-interest ahead of yours. What you learn from this tough lesson is to take friendships slowly, let them build over time, and pay attention to those who are still around when there’s a crisis or difficulty in your life or leadership.
Time doesn’t wait. Every leader has an equal amount of one asset that they can use to their benefit or detriment—time. Recent statistics indicate the average person wastes an hour more at work per day in self-interest or gossip. And nearly half of all employees rate their biggest time-waster as meetings, which consume an average of 21.5 hours of work time per person per week.[1] Then think about the hours you might spend scrolling social media, or watching YouTube, or plopped in front of the TV at home at night. The consumption of media is a massive time-waster. Leaders sometimes find themselves in the position where they simply don’t have enough time to accomplish something important, or finish something of real value, or invest in a meaningful relationship, because they’ve wasted hours and hours on trivial pursuits.
Scripture instructs us to use our time wisely and with intent. Ecclesiastes 11:4-6 tells us about godly stewardship of time: “Whoever watches the wind will not plant; whoever looks at the clouds will not reap. As you do not know the path of the wind, or how the body is formed in a mother’s womb, so you cannot understand the work of God, the Maker of all things. Sow your seed in the morning, and at evening let your hands not be idle, for you do not know which will succeed, whether this or that, or whether both will do equally well.” What a great leadership lesson! We don’t know what will happen, life and leadership are unpredictable. So, be diligent—get up early, go to bed late, and accomplish much in between. This is the hard lesson of missed opportunity. Have you ever found yourself in a situation where the outcome would have been entirely different if you had just used your time wisely?
Debt is hard to get out of. Our culture has a friendly attachment to debt, encouraging it for homes and cars and clothes and TVs and everything else you can buy. We make debt easy with credit cards, lines of credit, quick loans and cell phone apps. Data shows we spend more on a credit card than when we carry cash, and that our per-person consumer debt continues to rise at an alarming rate. The average person owes $6,360 on credit cards as of 2023, up 10% from the prior year.[2] What is often not talked about is the delinquency rate on credit, which reached 12.3% of all debt in 2025.[3] The hard lesson here is that we are getting into ever more debt individually and as a nation, and that debt is more and more difficult to get out of.
Scripture devotes a significant number of verses to how we handle money, specifically spending and debt. Proverbs 22:7 warns that, “The rich rules over the poor, and the borrower is the slave of the lender.” Financial advisors talk about “good debt” like a home mortgage or a growing business. The reality is that the Bible teaches there is no good debt. In general, we should avoid debt altogether. When we must have debt, like for a house, we should finance as little as possible, and get it out of it as soon as we can. Leaders who are deeply in debt and have one financial matter go sideways find they have far fewer options, and that a mountain of debt can take control of both your life and leadership, affecting decisions in all facets of home and work. Perhaps you have learned the hard lesson of losing something to debt, or having to start over with your bank account and credit due to overspending.
Share the hard lessons.If you have had to learn one of these lessons “the hard way”, or perhaps another life or leadership principle that you captured through hardship or difficulty, what should you do with that knowledge? A hard lesson might change your trajectory in life, re-wire your thinking, and help you going forward. But consider too that you can help others avoid the hard lessons. Authentic leadership is being open enough with others to say, “Here’s where I messed up. And I’m telling you this for your benefit—so that you won’t go down the same road I did.” What a blessing you might be to another leader who can avoid a pitfall. Make your hard lesson an easy lesson for the next person.
Easy lessons are the ones where the stakes of failure don’t affect your ability to learn them. But not every lesson in life is easy. James 3:2 reminds us, “For we all stumble in many ways…”