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After Going to Prison, He Worked Hard to Build a Career. Then This Happened, and He Discovered a Liberating Truth. Steve's story illustrates that every action has two risks.

By Jason Feifer

This story appears in the May 2024 issue of Entrepreneur. Subscribe »

Entrepreneurship is an endless series of hard decisions. I'm sure you're facing one right now. Sadly, I can't give you the right answer — but I can offer you something new to consider.

To really appreciate this, I first want to tell you about someone who faced a gut-wrenching choice of his own.

I'll call him Steve. He'd stolen things, served time in prison, and wanted to turn his life around. Finding a job was hard, but he eventually landed some freelance work for a big company. He threw himself into it, outworking everyone and getting noticed.

After a few months, a senior leader called Steve into his office. They talked for 20 minutes. Then the leader offered Steve a full-time job. "So just fill these forms out," the senior leader told him. "We'll do a background check, and then let's get to work."

Related: How to Master Decision-Making in a World Full of Options

That's when Steve panicked. He was desperate for this job and was so close to his dream — but it could all fall apart once his manager learned his background. Steve happens to read my magazine column, so he emailed me to ask for advice. "What should I do?" he wrote. "Should I tell him about my conviction?"

"I can't tell you what to do," I replied. "But I'll give you another question to ask: What's the cost of not taking action?"

Because here's the thing: When we weigh the risks of a decision, we usually think about the consequences of doing it. What's the upside? What's the downside? But that's only half the equation.

There are risks of action, but there are also risks of inaction. Every decision has a cost — either because of what we do, or what we don't do. You cannot truly know the wisdom of doing something, and decide whether it's worth the risk, until you explore the costs of not doing it.

This applies to every major decision you'll make. Are you in a relationship, unhappy with something, but afraid to tell your partner? Ask yourself: What are the risks of prompting some hard conversations, versus the risks of staying quiet as the situation gets worse?

Or let's say you're considering a career change. If you act, you might be gambling with your finances or career path. But if you don't act, you might feel stagnant and regretful. Both are risks. Both are consequences. Only you can decide which is worse.

Related: How Taking Calculated Risks Can Grow Your Business

This is a version of what I told Steve, the former inmate. Do the risks of action outweigh the risks of inaction? And here's what Steve did.

Steve realized that, in some ways, the future was already set. He could tell his manager about his past, or he could wait for his manager to discover it himself — but either way, his manager would find out. Steve could not avoid it. But he could decide how his manager found out.

If Steve took action and revealed his criminal background, Steve had a chance to own the story. He could explain himself and humanize the situation. If Steve took no action, and waited until the background check came in, questions would inevitably be raised. Trust would diminish. People might wonder: Was Steve trying to hide this? Did he think we wouldn't find out?

The manager's reaction was unpredictable. But the risk of inaction seemed greater than the risk of action.

So Steve decided to be forthcoming about his past. He emailed me the night before he'd planned to talk with the manager. "Pray for me," he wrote.

The next day, he sent me an update: The talk went very well. The manager said Steve was brave for being upfront about it, that he appreciated Steve's honesty, and that Steve would still get the job.

Because Steve took action, he now has the opportunity he's always wanted. He can restart his life.

We can move, or we can stand still. We can act, or we can stand by. But no matter what we do, we cannot escape risk. Every decision contains consequences. Every moment defines the next. And sometimes, the greatest risk comes from not doing the hard, scary thing…

Because sometimes, doing nothing gets you nothing.

Related: 4 Strategies to Help Business Leaders Improve and Accelerate Their Decision-Making Process

Jason Feifer

Entrepreneur Staff

Editor in Chief

Jason Feifer is the editor in chief of Entrepreneur magazine and host of the podcast Problem Solvers. Outside of Entrepreneur, he writes the newsletter One Thing Better, which each week gives you one better way to build a career or company you love. He is also a startup advisor, keynote speaker, book author, and nonstop optimism machine.

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