I Am a Negative Nancy by Default

My manager recently told me that I have a tendency to speak about things from the negative.

Not negative in the way you’re probably imagining. I’m not sitting in meetings telling everyone the project is doomed or responding to every new idea with a list of reasons it won’t work. It was much subtler than that. So subtle, actually, that I had no idea I was doing it.

She gave me an example.

She had asked me when something would be finished, and I responded, “Not for another two weeks.”

Her feedback was simple: Why not say, “In two weeks”?

I remember thinking there wasn’t much of a difference. Two weeks is two weeks. Whether I say not for another two weeks or in two weeks, I’m communicating the exact same timeline. The work will be done fourteen days from now.

Except, apparently, I’m also communicating something else.

“Not for another two weeks” makes two weeks sound like a problem. “In two weeks” makes it sound like a plan.

This was supposed to be a small piece of professional feedback. The kind you write down somewhere, nod thoughtfully at, and try to remember during your next meeting.

Instead, I went home and reevaluated my entire personality.

Because once she pointed it out, I started hearing it everywhere.

I realized how often my first instinct is to locate what’s missing. How quickly I can find the thing that might go wrong. How uncomfortable I am assuming that something will work out before I have enough evidence to prove that it will. Even when something good is happening, some part of me is already calculating how easily it could disappear.

I used to call this being realistic.

But I’m starting to wonder if I’ve just been a Negative Nancy with good reasoning skills.

The more I thought about it, though, the less funny it became. I don’t think I came into the world expecting the worst. I think I learned that expecting the best was a luxury.

People love to say, “When life gives you lemons, make lemonade.”

It’s one of those sayings we’ve repeated so many times that we rarely stop to think about what it assumes. There are lemons. There is sugar. There is water. There is a pitcher. And, most importantly, there is an assumption that there will probably be more lemons tomorrow.

But what happens when you grow up not believing that?

You don’t immediately start making lemonade. You save the lemons. You count them. You wonder how long they’ll last. You prepare for the possibility that no more are coming.

I grew up with a lot of uncertainty. Money was part of it, but I think the bigger lesson was learning not to assume that things would simply work themselves out. When you don’t have much room for things to go wrong, you become very interested in everything that could.

So I learned to prepare. I learned not to celebrate too early or get too attached to an outcome until it was actually mine. Somewhere along the way, I think I confused preparing for disappointment with being realistic.

Because expecting less can feel remarkably safe. If you don’t assume something good is going to happen, you can’t be blindsided when it doesn’t. If you don’t let yourself get too excited, you don’t have as far to fall.

For a long time, I thought this was simply responsibility. And some of it was. Caution made me resourceful, thoughtful, good at planning and very good in a crisis.

But it also taught me to approach possibility with suspicion.

There is research that helps explain some of this. We tend to give potential losses and threats more weight than equivalent gains, and uncertainty can make us even more attentive to what might go wrong. In an environment where mistakes have consequences, that isn’t necessarily irrational. Sometimes it’s adaptive.

The problem is that adaptations don’t always know when they’re no longer needed.

Your life can become more stable while some part of you is still waiting for it not to be. You can have evidence that things are going well and still search for the catch.

You can finally have enough lemons and still be afraid to make the lemonade.

I’ve always been risk-averse.

Some people make enormous life decisions because something “feels right.”

I make spreadsheets.

I research. I calculate. I think through the worst-case scenario and then the worst-case scenario of the worst-case scenario. Once I’ve eliminated approximately 97 percent of the uncertainty, I consider taking what I will later describe as “a risk.”

I’ve always admired people who seem capable of simply believing things will work out. I don’t understand them, but I admire them.

When someone tells me they’re quitting their job, starting a business, moving somewhere new, or pursuing something they’ve always wanted, my brain immediately starts gathering supporting documentation.

Have you thought this through? What happens if it doesn’t work? What’s your backup plan?

These aren’t bad questions. Somebody should probably ask them.

What I hadn’t noticed until recently is that I almost never ask the opposite question with the same seriousness:

What if it works?

I can tell you exactly what I stand to lose, but I’ve spent far less time considering what I might gain.

Once I noticed that imbalance, I started seeing how much of my life it has shaped: the opportunities I considered reasonable, how long I waited to feel “ready,” and how much evidence I needed before believing I was capable of something.

It also shaped how long it took me to bet on myself.

I’ve always been creative. I’ve always wanted to write, make art, design things, build things, create something that belonged to me. But creativity requires a kind of faith that has never come naturally to me.

There is no guarantee that the hours you put into something will give you anything recognizable in return. For someone who likes certainty, creativity is a terrible business proposition.

So I treated it like something I could do around the edges of the responsible life. The creative things could happen later, once I had enough time, enough stability, enough evidence.

But “once everything is secure” is a finish line that can keep moving forever.

Eventually, my circumstances changed faster than my instincts did. I had more room to make mistakes. I had evidence that one wrong decision wasn’t going to destroy everything.

And still, I approached risk as though one wrong move could send the entire thing tumbling down.

Having a safety net and feeling like you have a safety net are two completely different things.

Maybe that’s why I’ve always been skeptical of “follow your dreams” speeches. They make risk sound like a personality trait, as though some people are brave enough to leap and everyone else simply needs to stop being afraid.

But risk looks different depending on what you believe will happen if you fail.

Maybe some people grow up with enough evidence that failure is temporary. Things go wrong, you regroup, something else comes along.

And maybe some of us grow up learning to check the distance to the ground before we jump.

The most uncomfortable part of this realization has been thinking about the advice I’ve given other people.

I am the person you call when you want someone to think something through with you. I want the people I love to make good decisions. I want them to be protected.

So when someone comes to me with an idea, I troubleshoot.

Have you thought about this? What happens if it doesn’t work? Do you have a backup plan?

For most of my life, I’ve understood this as love.

And sometimes it is. Sometimes we need someone willing to look at the fine print while we’re distracted by possibility.

But now I wonder how many times someone has brought me a possibility and I’ve handed them my fear.

How many times has someone needed me to say, You could absolutely do that, and instead I’ve explained all the ways it could go wrong?

Because advice is strangely autobiographical.

Underneath the advice we give are our disappointments, our mistakes, the risks that worked, the ones that didn’t, and all the things life has taught us can happen.

If you’ve learned that things generally work themselves out, you might encourage someone to leap. If you’ve learned that mistakes can be hard to recover from, you might tell them to check the ground first.

Neither person necessarily knows what will happen.

We’re both using the evidence life gave us.

And maybe sometimes the people I love don’t need my contingency plan.

Maybe they just need someone else to imagine it working too.

I don’t want to turn this into a story about how growing up with less made me pessimistic and now I need to become a more positive person.

That feels too neat. And, more importantly, it isn’t true.

My manager’s feedback did not suddenly turn me into an optimist. I did not wake up the next morning ready to surrender my spreadsheets, trust the universe, and start making major life decisions based on vibes.

I also don’t want to villainize the version of me who learned to prepare for the worst.

She was paying attention.

Those instincts gave me things. I know how to plan. I know how to make something work. I know how to anticipate problems before they become emergencies. I know how to create stability because I understand what it feels like when stability isn’t guaranteed.

Seeing the glass half empty isn’t always pessimism.

Sometimes it’s inventory.

The question I’m sitting with now is what happens when you continue taking inventory long after you have enough.

What happens when the survival skill that helped you build your life starts determining how much of that life you’re willing to experience?

I don’t think my relationship with risk has actually changed yet.

What has changed is that I’m starting to see it.

That conversation with my manager made me realize that I’ve spent a lot of my life assuming pessimism is more intellectually honest than optimism. Preparing for disappointment felt realistic. Expecting something good without enough evidence felt naive.

But pessimism is still an assumption about the future.

So is optimism.

I’ve just spent more of my life trusting one of them.

Maybe the work isn’t convincing myself that the glass is half full. Maybe it’s simply noticing that half empty and half full describe the exact same glass.

When someone I love brings me an idea, maybe I can imagine it working before I explain how it could fail. When I want something, maybe I can spend as much time considering what happens if I get it as I do preparing for what happens if I don’t.

Maybe I can stop confusing hope with naivety.

And maybe, occasionally, I can catch myself in something as small as the way I describe two weeks.

Not:

“Not for another two weeks.”

Just:

“In two weeks.”

Same timeline. Same reality. Same amount of water in the glass.

I’m just learning that the empty half isn’t the only honest way to describe it.