Taking calculated risks in business doesn’t mean being reckless. Sometimes, waiting for the perfect moment may be the riskiest move of all.
We’re taught to be careful. Do your homework. Think it through. Know what you’re getting into.
All good advice.
But at some point, thinking becomes waiting. And waiting can become a very comfortable way of not doing anything at all.
If you’re waiting for the absolute perfect moment to make a move, when the stars align, the economy is flawless, your inbox is at zero, and Mercury is no longer in retrograde, you might be waiting forever.
Sometimes You Have to Say Yes First
I learned that pretty early in building PokerDivas.
When I first started the company, our events were small. We were learning as we went, and the largest groups we had handled were probably around 50 people.
Then a major company called. They wanted an event for 200 people. In another state. In a huge ballroom.
Had we ever done anything remotely that size?
No.
Did I know exactly how we were going to pull it off?
Also no.
I said yes.
Then I had to figure it out.
There were plenty of snags along the way. I still remember being at Penn Station with my events assistant, hauling all of our materials to the train when our bags burst. There we were, sitting on the floor of Penn Station, scrambling to get everything back together and hoping we wouldn’t miss the train that was supposed to get us to this very big event I had confidently said we could handle.
At that moment, “flawless execution” was not exactly what came to mind.
But we got there. And the event was executed flawlessly.
Suddenly, PokerDivas had gone from handling groups of 50 to knowing we could handle 200. Today, we can handle events for 1,000. But we never would have gotten there if I hadn’t said yes to 200 when I had no idea exactly how we were going to do it.
Taking a Risk Doesn’t Mean Being Reckless
That’s the funny thing about taking a risk. Sometimes you have to say yes before you have every answer.
Sometimes you do have to throw caution to the wind. But there’s a big difference between taking a risk and doing something stupid.
Do the homework. Understand what you’re risking. Know what you can afford to lose. Read the room. Read the people.
And then, sometimes, you just have to trust yourself and make the move.
Poker taught me some of that. You rarely have perfect information. You make the best decision you can based on what you know, what you see, and what your gut is telling you.
But this goes well beyond poker.
If I had waited for the perfect time to leave corporate America, I might still be sitting there. I had a good career. Leaving it to start something completely different wasn’t the obvious move or the safe one.
It was a gutsy one.
And I’m very glad I made it.
The Risk of Doing Nothing
Think about some of the decisions that have changed your own life.
Taking a job you weren’t completely sure you were ready for. Moving to a new city. Starting a business. Ending something that wasn’t working. Asking for something you wanted when you knew the answer might be no.
Very few of those decisions come with guarantees.
We tend to focus on what could go wrong if we take the chance. We spend much less time thinking about what we could lose if we don’t.
So maybe the better question isn’t, “What if this doesn’t work?”
Maybe it’s:
“Which will I regret more: taking the chance and having it not work out, or never finding out what could have happened?”
Sometimes you take the chance and it doesn’t work. You regroup. You learn something. You move on.
And sometimes you’re sitting on the floor of Penn Station with a burst bag and a mountain of materials, wondering what on earth you’ve gotten yourself into.
Then you get on the train.
Because the biggest risk may be the one that looks the safest: doing nothing.
Calculated Risks in Business: Three Questions to Ask Yourself
Taking calculated risks in business doesn’t mean closing your eyes and hoping for the best. Whether you’re making a career decision, building a business, planning a major corporate event, or facing a leadership challenge, there are a few questions worth asking yourself.
1. What’s the Real Downside?
We’re very good at imagining everything that could go wrong. Turn that fear into something concrete.
What is the worst realistic outcome? Can you recover from it?
If the answer is yes, the risk may not be nearly as big as it feels.
When I said yes to that 200-person event, I knew we had never done anything that large. But I also knew we understood event planning, we knew how to create an engaging corporate event, and I could assemble the right people to make it happen.
I wasn’t starting from zero. I was stretching beyond what we had done before.
2. Stop Waiting Until You Feel Completely Ready
You may never feel completely ready for the promotion, the new business, the bigger client, or the next leadership role.
There’s usually a gap between what you’ve already proven you can do and what you’re capable of doing next.
At some point, preparation has done its job. You have to trust yourself enough to cross that gap.
Just do it.
3. Ask Yourself Which Decision You’re More Likely to Regret
Don’t only ask, “What happens if I do this and it fails?”
Ask the other question too:
“What happens if I don’t?”
The opportunity you pass up has consequences just as surely as the one you pursue. Sometimes the safer-looking decision is the one that costs you more in the long run.
Calculated risks in business require you to do the homework, read the room and understand the downside.
And then be willing to make the gutsy move.
