How to Decide Whether to Take That Risk

Here's a totally different way of looking at it.

Welcome to One Thing Better. Each week, the editor in chief of Entrepreneur magazine (that's me) shares one way to be more successful and satisfied — and build a career or company you love.

Today’s one thing: Taking a risk.

That one thing, better: Choosing your risk.

Made with DALL-E

You’re deciding whether to do something.

But it feels scary. You’re hesitant. Unsure. Afraid. Is it worth the risk?

There’s no way to guarantee success, unfortunately — but there is something important that you’re not considering.

Today, I’ll help you consider it. And to start, I’ll share how this helped someone land a big job... and escape their haunted past.

The job of a (second) lifetime.

I don’t usually get emails from former prison inmates — but I got one recently, and the guy was in a panic.

I’ll call him Steve. He’d stolen things, served time, and wants 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.”

This is what sent Steve into a panic. He wanted this job. He was desperate for this job. He was good at it, had earned people’s trust, and was so close — but it could all blow up in his face.

“What should I do?” Steve emailed me to ask. “Should I tell him about my conviction?”

“I can’t tell you what to do here,” I replied. “But I’ll give you another question to ask yourself.”

Every decision has two costs

When we decide whether to do something, we’re really asking ourselves two questions:

1. What’s the upside to doing this?

2. What’s the downside to doing this?

These are fine things to explore, but the fundamental premise is flawed. Your evaluation is too limited. That’s because you’re only asking yourself: “What happens if I do this thing?”

There’s something missing: What happens if you don’t do that thing?

That is what we often fail to consider. 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 do not do.

You cannot truly know the wisdom of a decision — and therefore decide whether to make that decision — until you explore the costs of not making the decision.

Here’s when this idea became very personal to me.

What the cost of inaction looks like

I spent most of my 20s living in Boston, dreaming of working at a magazine in New York. Then I was offered exactly that — a magazine job in New York. But I wasn’t sure what to do. I had a happy life in Boston, with friends I cherished and a girlfriend I lived with.

The cost of action was clear: If I moved, I’d break up with my girlfriend and not see my friends as much.

But when I talked with my parents, they helped me realize the cost of inaction: I would have stayed in Boston, where there aren’t many magazines. My work ambitions would feel stifled. I might start to resent my girlfriend for it. And many of my friends would move away anyway, because that’s what people do.

I realized: The risk of inaction far outweighed the risk of action. I took the job, broke up with the girlfriend, and started a new life — which I cherish today.

This mode of thinking can be applied endlessly.

Are you in a relationship, unhappy with something, but afraid to tell your partner because you don’t know what will happen? Ask yourself: What are the risks of saying something and prompting some hard conversations.. versus the risks of not saying something, and the situation only getting worse?

Or let’s say you’re considering a career change. Ask yourself: What are the risks of taking that leap... versus the risks of not doing it?

This is a version of what I told Steve, the former inmate. 

And here’s what Steve did.

Steve realized that, in some ways, the future was already set. He could tell his manager about his background, or he could wait for his manager to discover the news himself — but either way, his manager would find out.

Action, inaction — both had the same outcome. Steve could not avoid it.

But Steve could decide how his manager found out.

If Steve took action, and told his manager about his criminal background, Steve had a chance to own the story. He could explain himself and humanize the situation.

If Steve took no action, he’d just wait until the background check came back. At that point, questions would be raised. Trust would diminish. 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.

Steve decided to be upfront 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, Steve 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 consequence. Every moment defines the next. And sometimes, the greatest risk comes from not doing the hard, scary thing…

Because sometimes, doing nothing just gets you nothing.

That’s how to do one thing better.

P.S. Want to come on my podcast, Help Wanted? We help people with their work problems (like this one, from an entrepreneur struggling to differentiate himself). You can be anonymous or use your name. Just click here to fill out our form.

P.P.S. Miss last week’s newsletter? It was about how to set goals in 2024. Read!

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