The one question that will change your life

I don’t remember why he said it, but I remember the car we were in on our way to a fancy networking event full of important people doing boss shit when he looked at me and asked, “What are you optimizing for?”

He squinted, his brown skin pinched at his forehead, staring me down as he liked to do. I wish I remembered what we were talking about, what earned his intense stare this time, what conjured the question that would change my life. I don’t think he knew it was that deep. It was.

He came from consulting, a world where everything is strategy and complex decisions and advising based on everything and nothing at all. This was a normal question, a basic question. He’d use it frequently, and eventually, I’d find myself reflexively reaching for it. Years later, long after I stopped working for him, I pulled it out of my toolkit and used it often.

The question is complex, made of layers and options. It isn’t about being right or wrong. There’s no binary framing to confine you. It puts you in control. It forces you to look past the immediate decision so that the decision blurs and something else comes into focus, something deeper. But all this is abstract and fuzzy, so let me now show you how it works with a simple example.

Should I eat this ice cream sandwich?

You’re staring at a creamy, rich, chocolate ice cream sandwich from across the room. It’s everything you need right now: sweet, smooth, comforting. It’s calling your name, and you want it so bad, but you know you shouldn’t. You’ve been eating terribly all week. You’ve been feeling sluggish and slow. You can feel your past decisions weighing on you. But it looks so. damn. good.

Let’s see how our question can help us make this decision. “What are you optimizing for?”

If you decide to eat this ice cream sandwich, you’ve decided that the temporary joy of sweet cream is more important that how you’ll feel the rest of the day. You’ve decided that it’s more important than your commitment to eating better. You’re optimizing for your feelings over your health. Are you ok with that? Are you comfortable with picking a few minutes of joy for hours of regret?

Maybe you are. Maybe you’ve been feeling like shit all day and you’ve decided that the few minutes of joy is exactly what you need to make it to the end of a painful, frustrating day. Maybe that sugar high is just long enough that it’ll help push you through the bullshit. Maybe those few minutes are really valuable to you, and you’re ok putting off your healthy-eating commitment for another day.

It’s not really about the ice cream. It’s about what picking the ice cream means. And if you can get to the underlying meaning of the decision, the other hidden decisions you’re making by making that main decision, then making that main decision gets easier.

Let’s do another one, a more personal one.

Why can’t I fucking focus?

We sat in bed and I said the things I always say: I’m doing too much, I’m overwhelmed, I’m spread too thin. To which he says what he always says: do less, take a break, say no. We were stuck in a loop. I was stuck in a loop.

But today, I was breaking the cycle! I told him hunched over in the middle of a mess of pink sheets. And I would do that by getting to the bottom of why I can’t seem to break out of this loop. I know I should focus, do less, say no, but I just. fucking. can’t.

He laid back as I talked, watching me stumble through options and feelings, until he lifted his head up and asked, “What if you could start over? Right now, everything disappears, no consequences. You get to do just one thing. How do you feel?”

I frowned. I felt the blood leave my face and fill me with terror. Just one thing? Only one thing? But … what if it failed? And with that reaction, I knew exactly why I couldn’t focus.

When I do all the things, I can’t fail. If one of the things I’m doing doesn’t go well, it’s not my fault. I was busy. Of course something was going to fall through the cracks! Who can blame me when there are so many projects, so many goals to meet and worlds to conquer. I’m trying. I’m doing my best. I’m working all the time. And as long as I felt like I was doing everything I could, I could go to sleep feeling good about myself.

I wasn’t optimizing for my success. I was optimizing for my ego.

I heard these words fall out of my mouth and they shocked me. I flipped through past decisions, past projects in my mind, and felt the weight of my realization. But what hit me harder was thinking about the other decisions I’d unintentionally made.

With each new project I started, I’d decided that it was more important for me to feel like I was trying to succeed than to actually succeed. I was picking my ego over my future. I was choosing a pat on the back over an actual win. I was optimizing for feeling good about myself. I just never realized that.

If I did just one thing, put everything I had into one project and it failed, I had nothing to hide behind. I had no excuses. I would have to face my failure, and I couldn’t handle that. So I hid behind projects and a calendar thick with invites, soothing my ego and wasting my time.

So, Saron, what are you optimizing for?

If you do nothing differently and remain in this loop, with monthly meetings ldraped in pink sheets, you’ve decided that your feelings are more important. You’ve decided that the idea of failure is too much for you to risk facing. You’ve decided that you would rather have a life of effort that will keep you in circles than to actually move forward. Is that what you want? Is that who you are?

And with that, everything else seemed to fall into place. That new idea that had tugged on me for months suddenly felt ridiculous. That project in my backlog looked ashy and useless. That important invitation to that really cool thing felt like a trap.

I keep that question in my toolkit. I use it often. When I find myself slipping into behavior that feels funny, when decisions get murky, when I feel the gap between what I say I want and what I’m actually doing start to grow, I pause and ask myself, “What are you optimizing for?” I keep the question taped to my monitor on a sticky note. It’s there, ready and waiting to help me course correct.

And if you ask me for advice, I’ll probably use that question on you too. It’s a beautiful, powerful question, full of layers and options and opportunities. I hope you find it helpful.