Tricky Part of Good Decisions We Rarely Talk About

5 min readAug 14, 2022


On embracing the messiness of life and decision-making

Image credit: Antonio Feregrino, Unsplash.

When I looked in the mirror, I realized that I had black circles around my eyes. The smeared mascara made me look like a panda. An exhausted panda with red eyes… I didn’t look very well and I didn’t feel well either. I felt embarrassed but more than that, I tapped into some grand sadness that wasn’t there before.

Here’s what happened.

Earlier this month, I got a new job. It is a visionary, forward-thinking leadership role I dreamed about. I was elated. I felt great about moving on to something new. I felt eager to step into the new role. Dream come true, rainbows and unicorns, right?


I also liked my current job. Sure, not everything was perfect, in some sense, I outgrew my role and it was about time to try something new. But I was happy where I was and I wasn’t looking for a new role. It found me. And it was great, exactly what I wanted. The right thing at the right time. After I said a big resounding yes, there came a difficult part- quitting my old job and parting from the team that I loved and that has supported me for many years.

And you know what? It sucked. Not because people weren’t nice and supportive, they definitely were. It sucked because I was sad to realize that the chapter was coming to a closure.

Sure, endings are only concepts and contain the seeds of new beginnings which are expansive and energizing. But endings are also sad.

And you know what?

That is OK.

We rarely give ourselves a pause to sit and be in that uncomfortable space of grieving what we have overgrown, closed, and finished.

For me, the sadness stroke me all of a sudden in my team leader's office when I was delivering her the news about my new role. It was my first time ever crying at work. I cried many times because of work in the privacy of my own room, but I never ever cried AT work. I always tried to keep the image of a professional persona and now I broke into tears.

Later when I looked at myself in the mirror, I realized that my makeup was all over and that I had a long conversation with my team leader not looking presentable. Oh well… we are humans, not robots. We get overcome by emotions now and then. This was an important moment for me. Even my therapist said: “Congrats, Milena, you are slowly but surely becoming a whole human again.”

Aside from neglecting the grief of the endings in our lives, one more thing we often neglect is this.

Even when we make an excellent decision, there will be some part of it that sucks.

And just because there is a part of it that sucks, it doesn’t make it less of an excellent decision. Something will always suck… and that’s OK. Sitting with that suckiness, grief, discomfort, fear, sadness, rage, FOMO, you name it, is the process through which we grow, expand, and become wiser and softer.

Two years ago, I stopped drinking alcohol. It was messing with my sleep and I was physically, mentally, and emotionally in a bad place. Alcohol wasn’t bringing me anything beneficial so quitting was the right decision, an excellent and brave decision. I never looked back. I don’t have hangovers, I am not wasting money, I am not ruining my health, and I found new ways of socializing without alcohol.

But sometimes, I still grieve my old identity of a party girl who is loud, confident, who makes decisions on a whim, and doesn’t give a shit. I miss that pleasant brain fog when self-criticism ceases and I relax and go with the flow without overthinking anything. Sometimes, on warm summer nights, I miss that feeling of adventure and freedom and infinite possibilities that seemingly open up after a couple of glasses of wine.

I said that alcohol wasn’t giving me any benefits, but the truth is that it was the crutch I needed until I didn’t. There were many pleasures, of course, but at some point, these pleasures were overweight by many of the downsides of alcohol. And even though those downsides were crystal clear, and even though I made the decision to quit with relative ease, the lost pleasures sometimes still haunt me.

Wouldn’t it be nice to be able to make a perfectly rational decision without ever thinking about what you are leaving behind? Hell yes! But we are humans, not robots so despite our rationality, we will sometimes find ourselves thinking about the “ghost ships”, as Cheryl Strayed put it.

“I’ll never know, and neither will you, of the life you don’t choose. We’ll only know that whatever that sister life was, it was important and beautiful and not ours. It was the ghost ship that didn’t carry us. There’s nothing to do but salute it from the shore.”

The word “decision” originates from the Latin words “de”, meaning “off” and “caedere”, meaning “cut”. When you make a decision, you choose one possibility and cut off all the rest.

Interestingly, the word “caedere” is also contained in words like “homicide” or “suicide”, which pertain to killing. Scary, right?

When we decide, we let one option live and kill all the others or let them die. It resembles pruning the trees to get better yield, it is a solid and necessary strategy. But, it still involves cutting and some short-term pain.

The idea here is that just because something about your decision sucks and is painful, it doesn’t make it a bad decision. Quite the opposite. Every good decision has that uncomfortable and painful moment. Unless you are deciding to completely remove yourself from an absolutely disastrous situation, every decision will involve some level of loss and sacrifice. And if that makes you uncomfortable, it doesn’t mean you are immature, it may mean that you are a human being.

This idea should help you stop overthinking decisions.

If you are endlessly optimizing in a search of excellent decisions that comes with no pain, discomforts, or downsides, do yourself a favor and embrace the messiness of life and decision-making.

Each good decision has the part that sucks. And that is OK. It doesn’t mean you shouldn’t make it, it doesn’t mean you should never feel the pain, it doesn’t mean there is one perfect choice you will never rethink and regret in any way.

Cutting is painful, but we need to keep pruning, deciding, and moving forward. Embracing the pain and grief that comes with that process will make us feel whole, wise, and empathetic towards our fellow humans playing this messy game called “life”.

Before you go…

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Engineer. Creator. Sustainability researcher. Obsessed w/focus, mental health, sobriety. On the quest to find gentler and more meaningful ways to live and work.