Hey there, settle in for a little confession. I’m not proud of it but I know acknowledgement is a first step. I’m seeing this as my debut post in this newsletter and I hope it gives you a sense of what I’m trying to do here. Thank you for reading! (If you feedback, reply privately to the email or leave a public comment on Substack.)

I feel dirty and I want to come clean: a lot of what I've published in the last 7 years on my blogs (1, 2) has not just been for learning or for sharing learnings. I wrote many things that signal my expertise or competence in a particular topic.

Learning about a topic by writing about it was an important motivation, yes. So was writing-as-thinking.

But there's no denying the fact that I would only ever publish something that I believed put me in a good light or at least not in a bad light. For the last 7 years of blogging, I've refrained from publishing anything that I believed could make me look bad to my current or future employer, colleagues, or friends in the industry.

What is the big deal?

Alright, so I prevent myself from publishing certain kinds of posts that put me in a bad light. Is that a big deal? Are there any deeper implications to this other than "feeling dirty"?

I'd argue yes, there are deeper implications.

A good place to start is to point out that I'm guilty of dishonesty by omission. I'm partially behaving just like IG influencers who show only the highlight reels of their life. They come off as disingenuous. I've learned to not trust them, so why would I happily behave like them?

IG influencers make people feel worse (usually not deliberately, but still) because people inevitably compare themselves with influencers who seem to have a perfect complexion, are in happy and mutually-respectful relationships, and are living an overall wonderful life.

We know probabilistically that this is unlikely, but we tend to forget to feel that way about it.

But the more insidious implication is that dishonesty inadvertently perpetuates what author Steven Pressfield calls our shadow careers:

Are you getting your Ph.D. in Elizabethan Studies because you’re afraid to write the tragedies and comedies you know you have inside you? Are you living the drugs-and-booze half of the musician’s life, without actually writing the music? Are you working in a support capacity for an innovator because you’re afraid to risk being an innovator yourself?

I work full-time as a software engineer and I blog regularly on the side. The side blogging gig entails no real risk, especially since, you know, I've prevented myself from publishing anything risky as explained earlier. Is blogging my shadow career? Is software engineering my shadow career? I mean, coding is writing.

If a colleague tells me during a casual chat that they are considering negotiating a sabbatical to go study philosophy, I know that what they are really saying is, "so, I just told you about this - do you think it's stupid? Do you think I'm way off on this? Am I the sort of person you see as potentially the philosophical type?"

So if I hold myself back from publishing anything that has a chance of making me look bad, but is actually what I'm thinking about, then I'm denying people the chance to feel heard and seen by reading that someone else (in this case, me) is also contemplating a similar mid-career move, like enrolling In a philosophy degree.

For some, that might be the only thing that they needed to hear to break out of their less-than-fulfilling shadow careers, or some other bad pattern that keeps playing out in their lives.

If simply publishing honestly could be this helpful, why not do it?

Honesty comes with a price

Honesty is a way to break free from the misery we might, through dishonesty, be putting one another through our whole lives. But honesty comes with a price that not everyone can afford.

Picture this. I published a blog post that admitted that I'm actually not that passionate about software engineering. In it, I lay out the reasons why I think I'm not that passionate and how I feel ashamed of it and how I'm struggling to chart a path forward? (These are just examples. But are they? Or am I just saying that to keep myself from being fully honest?)

Now what happens the next time I submit a job application? Well, the recruiter, doing her due diligence (i.e. googling your name), might simply give me a pass. "We want only to hire the best software engineers. This guy is not even passionate about his craft, I think we can pass on him." You can imagine what conclusions other people like my colleagues and manager might draw to my newfound detriment.

It's stupid, but people make flash judgements regularly. Especially recruiters who see hundreds of applications every day. I've witnessed this kind of reasoning used in a meeting once...

A fellow team lead was lamenting in a team leads meeting that one of his direct reports was "currently more serious about playing gigs with his band than work" and therefore glossed him over for an opportunity for a newly opened managerial position. This is exactly the kind of thing that I have been trying to avoid. These are the posts that "put me in a bad light."

This brings me to affordances and my obligation...

Some people can afford to be honest more than others

In How to Do Nothing, Jenny Odell explains,

[…] historically, some can more easily afford to refuse than others. Refusal requires a degree of latitude—a margin—enjoyed at the level of the individual (being able to personally afford the consequences) and at the level of society (whose legal attitude toward noncompliance may vary).

Odell may be talking about activism, but I think this "personal affordance" applies similarly to online publications like this newsletter. Writing is probably one of the most powerful forms of activism, even if the writer isn’t trying to be an activist. The pen is a pen, and it is mightier than the sword.

So here's the thing: as a software engineer with a BSc degree to fall back on, I feel like I can afford to be honest more than someone who is living literally from paycheck to paycheck, someone whose ability to pay rent and fill stomachs depends on keeping their boss unreasonably happy.

In other words, I feel like I have a responsibility to play that role. There's almost a moral obligation for those who can to be honest.

It'd be remiss at this point if I didn't highlight why I've chosen to create a paid subscription option for this newsletter: the more paid subscribers I have, the more I can afford to share my thoughts honestly, which could lead to more people feeling less alone, more confident, and more courageous. The only things I need to prove are that I can keep being honest and that honesty is worth paying for. Time and persistence will tell.

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Let's end this post by asking why we might want to be honest with ourselves for our own good.

Selfish reasons to be honest

I heard Naval Ravikant on a podcast episode where I think he was spot on about two good selfish reasons to be honest —

First, you want to be honest because it leaves you with a clear mind:

You don’t want two threads running in your head, one with the lies you tell —and now have to keep track of—and the other with the truth. If you are honest, you only have to think about one thing at a time, which frees up mental energy and makes you a clearer thinker.

Dishonesty by omission is not lying, but it is dishonest.

And the second, which I think is more important, is that by being honest, you are "rejecting the people who only want to hear the pretty lies" and in the long term, you "create room for people who like you exactly for who you are."

Both of these are summarised nicely in a more recent tweet:

Naval @naval

The selfish reason to be honest is to clear the mind of exhausting lies and to navigate towards people and situations where you can be completely authentic.

Not everyone can afford to be publicly honest. But at least do yourself a favour and be honest in private.

So, what now?

This post is turning out to be quite a sombre one. I'm sorry for that! I guess honesty often leads us into dark places. Here’s a picture that hopefully cheers you up and serves as a “thank you” for reading the whole post:

Me, with a horrible haircut, holding a Cabernet Sauvignon during my quarantine in Singapore. Also comically representative of how I feel about my dishonesty.

From now on, I'll stop writing posts whose main purpose is to prop up my professional competency or social desirability. I will actively prevent myself from doing that. I should be able to sense if I'm bullshitting myself.

And, going forward, I'll write things that are honest in their intent and authentic to myself. This post represents my first step into this better world where I'm honest with myself, honest with you, and where I am always available to tell you, “me too."

The One-Way Mirror

I've been dishonest in my writing for 7 years