Story 35

Overthinking the why

Hi, I’m Andrei, the human behind this issue of Upstairs. Leadership trainer and consultant for the past six years, various technical and management positions in software companies before that.

We’ve all heard about “The Why”

The purpose, the core idea, the reason to do anything. The Why as the generator of motivation, as the thing that brings teams together. Why are we doing this? What is our core purpose? What is our mission?

There’s a lot of why at the personal level too. Why should I do this? Why should I not do that? Why is this good for me? Why don’t I like this? Etc. 

Exploring the why is useful, I’m not saying you shouldn’t, but today I want to talk about over-exploring the why. Overengineering the why. 

Paralysis in the Why analysis

This is a trap that I’ve fallen into many times, and I’ve had to learn to actively stay away from it. 

It usually goes like this: I wake up one day, and I feel like I’m doing too many things, I’m too spread around, I don’t have enough focus, I’m wasting my energy. I say to myself, “I need to organize and prioritize.” I start making lists, objectives, and trying to figure out my priorities. I take every project, every idea, every thing that I do, and I ask myself: Why?

Why am I doing this?
Why should I continue doing this?
Why is this important to me?

Why should I take precious time out of my day to go into the city and take pictures of the streets? What does that really do for me?
Why should I take my tent and go camping in the forest for a couple of days? Yes, it’s nice, but could I use that time for something more productive?
Why should I play Starcraft 2? Is a video game going to help me get better at anything?
Why should I try to restart writing literature, as I used to as a student? What is that going to be useful for? 

All these examples, and others, are real examples from my life that would never stand the test of “Why.” There is no logical, reasonable “Why” that would justify investing in these activities. There’s no “business” case I can make for any of them. They aren’t my profession, they aren’t going to be more than, at best, passions or hobbies. I’m not going to be “the best” at them. 

These, for me, are not the kind of things that I will focus on to the degree that I can hope to become relevant in those fields or to influence anyone else. 

Many times, I’ve stopped or cut these things down, or I had that voice in the back of my head as I was doing them, feeling bad that I’m not being “serious enough,” telling myself that I’m wasting my time. I’m just playing. What are you doing in this abandoned train yard, wasting four hours of your life going through deserted train carriages? You could have written a new newsletter at this time, or thought about a new training. 

That is paralysis in the why analysis, and I don’t like it anymore, and I’ve come to a point where I’ve learned to take it easy on The Why. Not ignore it completely, but chill a bit with it. 

Less Why for me

I’ve come to consider that this exaggerated focus on The Why is bad. It sounds inspiring when you think about it, even the word itself, “Why,” sounds deep, but it can easily get to be the exact opposite. A limiting, accounting-like perspective on what you should be doing or not doing. You don’t want to organize your creativity and passion like a ledger. 

I’ve come to the conclusion that I don’t have to justify everything to myself by having a clear and reasonable Why. I can just do things because I like them. Because I feel like it. Because they’re interesting. Because Why Not? 

That’s where my creativity comes from, and that’s where I push my limits. I’ve learned to take it easy on The Why.


Contributors of this story: Andrei Postolache wrote this gem, Oana Filip provided feedback and edited it, Andrei Ungurianu put it all together, George Olaru designed it, Răzvan Onofrei was in charge of the development.

A question by Andrei, the author of this story:
What is your relationship with the Why? How sure do you have to be that something “is the right thing to do” before you do it?

Conversations 6 comments

Let's start a personal, meaningful conversation.

Example: Practical philosopher, therapist and writer.

Thank you for raising this question, Andrei. It is an important one. And a practical one, to boot.

My relationship with the Why of doing this or that is a complicated one, multilayered if you will. Much like you portrayed your own. There are inner Whys and there are outer Whys. And then there are many in between that surface depending on the amount of rationalization needed.

My inner Why stayed mostly the same throughout the years as it comes way back from my childhood: to challenge myself, to do stuff for the fun of doing it, for the experience of doing something I didn’t know for sure I could do it, for the thrill of surprising myself with ideas that I didn’t know I had. This is the core of my Why onion. 

As I progressed through life and read a ton of self-help and management books, because it felt like the necessary thing to do, and talked to various consultants and coaches, because it also felt like the necessary thing to do, I started adding more and more layers unto that core of mine in an attempt to portray complexity, rationality, and causation where there really wasn’t any. This has started in my professional life but it quickly diffused throughout my whole life – I am bad at that work-life separation as I see no natural border between the two realms.

After yet another couple of years of mental clusterfuck between my common sense and the ready-to-eat dogma of goal-setting, measuring-what-you-want-to-get, and perpetual-optimisation-unless-you’re-stupid, I managed to chill, see bullshit for what it is, and stand more firmly on my own two feet. I removed many, many layers between my inner and outer Why, thus bringing them closer together, as they should be.

I do what I do because I wouldn’t be myself if I didn’t do it. I don’t know about others, but I am inextricably defined by what I do and don’t do. From being a husband, raising my kids, to playing tennis, reading books, writing, to coding and creating digital products, investing, and the occasional gardening. 

Andrei Postolachesays:
Relevant commenter background or experience:consultant

Thank you for the comment Vlad. I find myself in many of the ideas you mention. It also took me a while to learn how to give myself permission to “just do” something, without the need to come up with a sort of mental “business case” of why I should do it. 

To answer your question, I need to be very sure that what I’m planning to do is the right thing and will lead to something “great.”

This has been a significant blockage in my attempts to start small projects, ideas, passions. Being a marketer surely doesn’t help—my profession forces me to find and pursue only the best ways to achieve a specific goal. Far less is left to gut feeling or whims. Which can mean missing some opportunities because of a lack of proof that they can work.

Applying these strategies to my passions and hobbies makes me spend more time tweaking the process, the goal, the necessary steps, tackling the “what ifs” instead of just doing something without having a clear idea of where it’s going to take me.

On that note, thank you for writing this. I needed to hear it. It would be great to come to terms with doing things because I like them, and they bring me joy.

Andrei Postolachesays:
Relevant commenter background or experience:consultant

Glad you found it useful, Andrei!I think you raise an interesting point, what do you do when you want to try something new, but you’re working on a project, for a client, and you need to deliver. You can’t just ignore that client’s needs and do whatever you feel like. In these situations I fall back on a lean/agile/just in time/just enough mentality, which still allows me to experiment and try new things, while being reliable. However, for me at least, the big problem wasn’t in professional situations. Once I accept a project and I say “I’ll do it”, I personally don’t have many problems doing what needs to be done. I’m ok with that. The problem, for me, was that this very efficiency driven, “I only do things that are WORTH it” mentality was taking over my entire life 🙂 And while I’m fine to think like this in most professional situations, I don’t want to think like this when it comes to my passions.

Relevant commenter background or experience:Coach for multilinguals

Thank you for the inspiring article, I’m happy to see this topic addressed directly, personally and provocatively at the same time. I have similar experiences to yours when it comes to the habitual WHYs in relation to my actions. What I can add are the often not helpful WHYs addressed to more complicated feelings and health problems – the unpatient “why am I feeling this way?” The answers to such questions lie sometimes so deep in our bodies, minds and souls, that we need to allow time for them to reveal and also a specialist’s guidance, be it a doctor or a therapist. 

Andrei Postolachesays:
Relevant commenter background or experience:consultant

Thanks for the answer, Corina, I’m glad you found the article useful!Accepting a degree of uncertainty and ambiguity is I think part of it, at least for me. No matter how well I analyze and interpret a situation, or my own thought process, or my feelings about something, in some situations I just can’t be sure why I’m feeling in a way about a particular thing. I try to let it be, not obsess about it, and the answers usually emerge. 

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