Steven Chien


How to swing for the fences in Sports, Business and Life



You just passed your second anniversary on the job. You’re on the big boss’ radar, but nowhere near the top of his list. To most, you’re known more for your father’s accomplishments rather than your own.

So you decide to change your approach and “swing for the fences.” Literally.

The traditionalists are offended and peeved.

“It’s risky” they say. “That’s not how we do things around here.”

But you’ve done your homework and concluded it’s a risk worth taking. So you keep at it, honing your craft everyday until things finally start to click. One click leads to another, and another, then a series of explosions.

Now you’re on the world stage. Touted as the cream of the crop in your industry. The awards and accolades seem never-ending.

Say “Hi,” Cody Bellinger.


Cody hit just 1 home run his senior year in high school. He hit 4 in his first 100 games as a professional ballplayer. After a series of adjustments to his swing, Cody went on to hit 40 home runs in 130 major league games to capture Rookie of the Year honors while leading his team to the World Series.

Cody took a calculated risk in changing his swing, a risk that has paid off handsomely.

Swinging for the fences is a baseball idiom describing someone who is swinging with all their might to hit a home run — used in non-sports settings, it’s meant to convey “putting it all on the line and going for it!”

The game of baseball, a fairly conservative sport with many longstanding traditions, is being revolutionized by analytics. The stat geeks have cross-examined the numbers. Their verdict?

“Swinging for the fences” outweighs the risks of striking out.

We see the same trend in the sport of basketball, where the 3-point shot has transformed the game inside-out. Stephen Curry, 2-time MVP and 2-time NBA champ, routinely passes up the easy 2-point shot for the more difficult, more risky, yet more rewarding 3-point shot.


Likewise, in the startup world, angel investors and VC’s assume that 80% of their investments will “strike out.” And they’re totally cool with that. Their entire business model relies on the “grand slam” investments that yield 10–100x returns.

“A grand slam investment is worth 100 home runs”
~ Jason Calacanis

Some say the same pattern arises in our personal relationships as well. As Mark Manson eloquently puts it: The Law of “Fuck Yes or No” is the best way to approach your dating life. Go for it all…cuz anything less and you’ve already lost.

What’s behind all of this?

The stat geeks have been quantifying the world: sports, our bodies, our Tinder dates. Thanks to them, we’re able to pinpoint the few key actions that produce outsized returns rather than rely on traditional assumptions backed only by anecdotes….for better or worse.

But the more intriguing factor is psychological.

In all aspects of our life, there is simply so much information out there that only the remarkable stands out. Our brains haven’t evolved much since the primitive caveman days. We’re still optimized to spot the outlier — the lurking sabertooth tiger, the brightly colored yet poisonous flower, the soaring arc of a home run. We can’t help but focus on the outliers of the world, as if our lives still depended on it.

“Remarkability lies in the edges. The biggest, fastest, slowest, richest, easiest, most difficult. It doesn’t always matter which edge, more that you’re at (or beyond) the edge.” ~ Seth Godin

The victories, the investment returns, the love of your life is waiting at the edges.

And no one gets to the edges by taking a half swing.

No one.

“Ya but…easier said than done!”

…shouts the cynical little devil sitting on my shoulder.

Whenever one decides to “go for it,” is when pessimism comes out in full force.


We all inherently know our true desires lie at the edges, just outside our comfort zone. We feel it in our bones.

And yet, we let the little devil on our shoulder paralyze us with FUD.

Fear. Uncertainty. Doubt.

FUD grabs our attention with some remarkable stories. The worst kinda stories, filled with excuses, imagined embarrassment and other nonsense. These stories are mostly untrue because FUD is basically fake news for ourselves.

The absolutely WORST thing you can do is to let FUD stop you from swinging for the fences!

I’m not sure if there’s a single magic bullet to counter FUD. I wish there was.

But I have found the following five questions helpful in keeping oneself honest:

1) What is the ONE ACTION that would make the biggest impact?

Your equivalent of a home run swing or a 3-point shot. The one action that has an outsized impact. The 80–20 rule in full effect.

Notice we’re saying ACTION, and not RESULT. Actions are 100% under your control. Results are not. (more on this below)

My bet is that you already know what this one action is. It’s the action you’ve been procrastinating on. The important, but not quite urgent action.

Your ONE ACTION is like a compass, your own personal North Star to keep you on track.

Yea, there might be some risk to it, which leads to the next question.

2) Is it a RECKLESS risk or a CALCULATED risk?

There’s a huge difference between the two. HUUUuuuuge.

Reckless is betting more than you can stand to lose, without any forethought.

Calculated is doing your homework and evaluating potential gains versus potential losses.

Take Richard Branson, for example. Despite his daredevil reputation, he actually believes that protecting the downside is critical. We make sure that no one risk is going to topple everything.”

“Your ability to take calculated risks and your incurable optimism will lead to great heights — both in business and in life.”

Going a step further, the risk/reward of almost any decision can be broken down into an expected value (EV) number.

Why on Earth would you resort to math?!?

Because that little devil loves to use uncertainty and doubt to lead you to bad, fear-driven decisions. Calculating your EV number reduces uncertainty, thereby lessening the little devil’s hold on you.

So if you can do 4th grade math, then you can calculate your EV number. No excuses!

3) What’s your practice regimen for honing your ONE ACTION?


Everyone needs to practice their craft, even you, Mr. Iverson.

Cody Bellinger refines his home run swing in the batting cages between games. Steph Curry practices hundreds of shots a day, so many that his hands are calloused like those of a woodchopper.

Practice transforms your ONE ACTION from a burdensome, difficult task into one that feels automatic and effortless. Once it’s a habit, there’s no room for any FUD to get in the way.

Your regimen could be as simple as blocking off practice time, or you could turn it into a side hustle (highly recommended).

In short, practicing your craft once a day keeps the little devil away.

4) Mentally prepared to fail the majority of the time? How about 80% of the time? 99%?

It’s a lesson in emotional resiliency from angel investors like Jason Calacanis:

“You have to get very comfortable with the concept of losing seven, eight, nine out of 10 bets.”

Can you repeatedly fail and still remain optimistic?

“Failure” is the little devil’s favorite way to ramp up the FUD. He’ll be shouting in your ear to quit. He’ll remind you of how life would be so much easier if you just stayed in your comfort zone.

But the thing is, we all have blinders on when it comes to our own progress. You won’t know whether you’re doing all that well until you look at your actions over a period of time.

So it’s important to have a consistent practice regimen that prevents you from quitting too soon. If you can mentally reframe “failures” (results-oriented) as “practice” (action-oriented), it’ll help keep your head up and keep on going like the Energizer bunny.

And finally…

5) Are you ignoring the little angel on your other shoulder?


It’s easy to give all your attention to the little devil who’s screaming and shouting. The little angel, on the other hand, tends to whisper.

Clear some headspace so you can hear those whispers:

  • Take a break.Yes, you do deserve a break from time to time. You’re not a robot.
  • Meditate, even if it’s only for 2 minutes. Ask Tim about it. Love listicles? Here’s 21 more reasons.
  • Journal your thoughts, any thought, on a blank sheet of paper. Throw it away if you find it embarrassing or whatever. It’s not for others, it’s for you. You just might surprise yourself.

Only after shutting out the FUD can you hear what your angel is trying to tell you. Sometimes what you really need most was there all along, hiding underneath the FUD.

None of these questions in isolation do much to quell the FUD. But in aggregate, they do help lower the volume of that sneaky little devil on our shoulder. Throw out the mental trash so you can focus your mind on your craft and positive remarkability.

Be like Goofy.

Step into the batter’s box and swing for the fences!


Enjoyed this article? Please help out your friends with a 👏 or a share.

More by Steven Chien

Topics of interest

More Related Stories