Why Career Failure Builds Better Leaders.

If you look at my career story, it resembles a dark comedy. It is filled with stress, disappointment, and absurdity. Along the way, I endured long-term unemployment and the dissolution of two marriages. To the casual outsider, my career journey looks like a futile struggle. Looking back, each failure and setback made me a better person and leader.

When Corporate Hero-Worship Goes Wrong

The business press likes to inflate leaders into mythological figures attempting to conquer the world. Entrepreneurs look heroic as they struggle to build their businesses, and CEOs of Fortune 500 companies seem more powerful than the kings of ancient Persia, so it's easy to do. Unfortunately, the scramble for attention, wealth, and power often distracts from running a successful business. It also elevates destructive people into leadership roles. These are people who break the law, steal from customers, and exploit their workers. The Forbes 30 Under 30 list often doubles as a police blotter for fraud and white-collar crime. It creates a disturbing message that power and wealth are the only things that matter in the business world.

Amid all the talk about free markets and the superiority of capitalism, the core work of buyers and sellers exchanging and building value got lost. Learning to manage logistics, keep accounts payable operating, and deal with workforce issues is hard work and lacks the glamour of a flashy IPO or a billion-dollar market capitalization. This hidden, unglamorous work keeps the business world turning.

The Fragile Engine of Everyday Trust

Each day, the sun rises and sets because people do the routine things that keep business moving. Trust underpins those routines. Deliveries happen daily because invoices are paid. People pay those invoices because the services they receive provide them with value and make their lives easier. At any time, the system can fly apart if trust between customers and vendors breaks down. Here's the problem: businesses think they can avoid this by creating monopoly situations. If you are the only person providing a service, you can be as unaccountable as you like and avoid the consequences.

This strategy works in the short term, but it eventually catches up with everyone. Enron dominated energy markets on the American West Coast until it all came crashing down. Its criminal behavior was so brazen that Congress imposed a series of reforms known as the Sarbanes-Oxley Act. Sam Bankman-Fried is in prison today because he stole from his investors. Bankman-Fried is a textbook example of the ethically and financially dubious world of cryptocurrency. For a few years, he was highly successful, but eventually his fraud was exposed, and he lost everything, including his freedom.

The business world is full of grifters and confidence artists, but most people are just trying to keep the lights on and build wealth for themselves. Each fraud undermines the system and hurts the trust many businesspeople have built over decades through steady work. Remember this any time you want to take a shortcut or face an ethical dilemma. More often than not, those shortcuts stem from a sheer terror of failing.

Setbacks Build Better Leaders

Failure comes up in this discussion because we are often taught to treat it as a product of personal shortcomings. We did not fail because we were placed in an impossible situation or not given the tools to succeed. We failed because there was something defective about us. It is a destructive myth that discourages more people from success than any overt oppression in society. Failure is an educational tool, and we should embrace that.

Each failure I have endured has improved me in both business and life. Getting humbled helps you focus and keeps you from reckless arrogance. It also forces you to pause in ethical dilemmas and take stock of what values matter. My leadership style would be very different if I hadn't experienced the personal setbacks I did.

My career is not a futile struggle. Instead, I survived two major downturns in the technology economy. I navigated the giddy, stupid days of the dot-com bubble, and now the artificial intelligence bubble growing on Wall Street. My journey has taken me into private business, entrepreneurial startups, and now government contracting. With over 20 years of experience, I help others and am committed to making sure they avoid the mistakes I made in my career. I am tougher than I used to be, but I am not heartless. I used to fantasize about being a founder leading a transformation in the business world. Today, I am the crusty veteran making that change happen and the person founders count on. I think this is a good place to be, considering an absurd career marked by failure.

Until next time.