The Question I Always Forget to Ask

It's deceptively simple, life-changing, and...I rarely ask it

Photo by manu schwendener on Unsplash

I am currently taking Ramit Sethi’s Earnable course for aspiring entrepreneurs. It’s self-paced, which fits well with my schedule. I try to watch 1-2 modules per week when I need a break from writing and so far, I’m really enjoying it.

In one of the videos, Ramit speaks to a classroom full of adults enrolled in his course. As they work through frameworks for selecting business ideas, he addresses the limiting beliefs they will inevitably experience as they test their ideas in the marketplace.

To assuage their fears, Ramit tells a story¹ about a college student he mentored. The mentee, who was on a summer internship, wanted to reach out to his boss’s boss to pick his brain and ask him how to be successful at the company. But he was hesitant. He told Ramit all the reasons why he thought it could backfire, from his boss getting upset to the person saying no.

Ramit nodded, said he understood, then asked his mentee to turn his thinking around: “Now say that back to me, and this time flip it to all the good things that can happen.”

I rewound the video and listened to the story over again. Then I groaned.

Flip it to all the good things that can happen.

Why do I always forget to do this?

A lightbulb moment

I groaned because he might as well have addressed this story to me.

It seems intuitive — all we need to do is look for the positives in a situation. Easy enough, right?

And yet, when I’m feeling down or going through a tough time, do I do this? Never! (Well, almost never.) This won’t shock anyone who knows me, but I’m not the most positive person in the world.

It turns out I’m not the only one. We all fall victim to negativity bias — our human tendency to focus on the negatives and ignore the positives. Asking “What are the good things that can happen?” is a rebuke to negativity bias, but it takes work. A lot of work. Instead, it’s much easier to obsess over what can go wrong.

Every time I think about an upcoming decision, I dwell on the downsides. I overlook what I could gain and lament what I could lose. I want to cover my bases. I don’t like surprises. It’s only when I have the downside risks understood and accounted for that I feel comfortable maybe saying yes.

Rarely do I “flip it” and think about what could go right. Seldom do I ask, “What is the best-case scenario?”

Risks vs. Rewards

This isn’t so much about “seeing the sunny side of things” as simply evaluating, if everything were to break in our favor, how a decision could change our lives for the better.

Because events can break in our favor. This should always be factored into our risk-reward calculus and given equal weight.

But it’s not easy. When we’re going through hard times, any potential risk is closely scrutinized. The downsides are magnified. We ask, “If this goes wrong, will it make my life harder? Will it add more pain and frustration to my already difficult situation?”

These are understandable concerns, no question. And in delicate situations, understanding the downside risk is essential.

But there is always the chance that things work out. You never know if taking a big risk is the catalyst you need to achieve a life breakthrough.

Lessons from the past

When life is going well, asking, “What is the best-case scenario?” seems obvious. Of course we see the positives. Why wouldn’t we? Life is great.

But when we’re struggling, what’s “obvious” has an annoying way of escaping our minds.

Thinking back to how I handled my disease in the early years, there are many times when asking this question could have helped me. But I didn’t ask it. My life had hit the fan, and all I could see were the negatives.

It was only when my back was against the wall that I finally, mercifully, considered the positives.

The most glaring example was when I struggled to ask for help. (I talked about this at length in Out of the Abyss.) All I could see were the downsides — the stigma, the shame, the fear, the possibility of rejection from my friends and family.

Had I been able to see what could go right, I would have realized that the rewards far outweighed the risks. Having people come to my aid ultimately made things easier, but it took many years to make the ask.

Dwelling on the downsides also impacted me whenever I needed to get a new piece of adaptive equipment. Whether it was getting leg braces, crutches, or a wheelchair, I resisted, kicking and screaming. All I could focus on was what other people thought of me or what it meant for my future.

Had I weighed the good things that could happen, I would have seen that adaptive equipment had the potential to reduce my falling risk significantly. They also would allow me to walk longer distances with less exertion. And when it came time to use a wheelchair, it would eliminate my falling risk altogether.

With each piece of equipment, there was a period of discomfort. That was unavoidable. But once I adjusted, and saw the good things that did happen, my perspective changed.

It requires constant reinforcement

Unfortunately, it’s easy to fall back into old habits. Sometimes, obvious lessons need to be reinforced over and over again.

After I watched the Earnable video, I wrote down “What is the best-case scenario?” on a digital note on my computer, as a way to keep this perspective top of mind and fight back against negativity. I still forget to ask this, but I’m starting to remember more often. But without the note, I’d never remember.

That’s my action step for you today. Write this question down somewhere where you’ll see it. Because when you’re feeling down — and I say this from experience — it becomes that much harder to think about what could go right.

And this isn’t something you’ll want to forget.

Related Articles

Re: asking for help:

Out of the Abyss

Why It’s So Hard to Ask for Help

Making the Ask

Another way to think through our decisions:

What Really Matters in the End

Risk/reward when it comes to interacting with others:

Go positive, go first, and be constant in doing it

1. I’m not giving away anything proprietary to the course so I assume it’s okay to share this.