Calculated Risk

The Simple Newsletter - Issue # 092

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Adam’s Thoughts

Sometimes you take a massive risk and it works out.

Sometimes you fall flat on your face.

Over the last week, I’ve watched people take some unbelievable risks.

I’ve watched people hire.

I’ve watched our clients make major commitments.

I’ve watched incredible CEOs put themselves into rooms and situations they normally never would have.

I’ve watched teams finally solidify their next move and say:

We’re doing this.

And here’s what I noticed.

Every one of those decisions had one thing in common:

They created space to understand the consequences.

Not just the upside.

The consequences.

Because risk feels very different once you stop pretending there’s nothing on the other side of the decision.

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Adam’s Lessons

If you don’t understand the consequences, it’s really hard to go all in.

Most people spend a lot of time thinking about the positive outcome.

And that makes sense.

The upside is exciting.

It gives us energy.

It gives us something to chase.

But how often do we actually stop and ask:

What happens if this goes wrong?

And when I say consequences, I don’t only mean the negative things that might happen if you take the risk.

What about the consequences of not taking it?

The opportunity you miss.

The lesson you never learn.

The relationship that never develops.

The person you never hire.

The regret you might carry years later because you knew you should have moved and didn’t.

Taking action can absolutely create negative consequences.

You might lose money.

You might make a mistake.

You might realize the decision wasn’t right.

But those consequences may also be exactly what teaches you what to do next.

That’s why looking at the downside can actually create confidence.

You’re no longer staring into the abyss.

You have some idea of what might be down there.

You know the worst-case scenario.

You know the bumps you might encounter.

You know what you’re willing to tolerate.

And maybe most importantly, you know what you’ll have to live with if you choose not to move at all.

Risk doesn’t require certainty.

It requires awareness.

So here’s to taking risks.

But more importantly, here’s to understanding the consequences well enough that when you decide to move…

You can actually go all in.

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So here’s my question for you this week:

What risk are you considering right now—and have you honestly thought through both the consequences of taking it and the consequences of doing nothing?

Reply and tell me. While I can’t respond to every message, Tom and I read every reply, and we genuinely appreciate hearing from you.

That’s all for this week.

See you next Saturday.