On Boredom and Fear of Making Something Lame [Letter#17]

An inability to cope with boredom kills more success than any kind of competition." - tiny mba, by Alex Hillman

What should I work on next? This is a recurring question. When you're building side-projects, how do you decided when to stop working on the current thing and start working on a new thing? There are times when we've done everything we can but the idea isn't right and we should absolutely move on. More often than not though, we abandon side-projects because of a simple reason — we get bored. And we likely stop prematurely.

"An inability to cope with boredom" when I first read that, I recall pausing and thinking about it for a long time. It seems boredom is one reason we may not be seeing success. But what does this imply, what does this boredom look like in practice? It seems to be about not sticking with something long enough or not seeing something through, especially when the work starts to feel tedious or repetitive or well, boring.

I miss going on hikes in the bay area and I started thinking about this boredom thing in terms of an analogy between the entrepreneurial journey and hiking a mountain.

Have you ever gone for a hike early in the morning, maybe to see the sunrise? (If your reaction is 'no are you crazy' that's okay stay with me anyway). Arriving at the trailhead, about to start the climb, feels like a huge accomplishment on it's own. Because in order for that to happen, we had to research the hike, wake up early, put on our gear, pack snacks and drive to the parking lot.

We get to the trailhead, explore the map. What if, after we've walked a few feet, we run into some other hikers who say there's a better view of the sunrise from a different (easier, shorter, faster, just better) trail just down the road. Would we get back into our car to drive somewhere else "better", should we?

We know logically that, ultimately, in order to see the sunrise, we need climb the hill. Even though getting out of bed early and driving to the trailhead feels like a huge accomplishment, that's not all we set out to do. We are on a path, but we need to keep going. We need to leave the trailhead and climb the hill.

Boredom is one reason why we try different things but we don't stick with them long enough to see success. Sometime it feels like we haven't left the trailhead.

So what can we do about this observation that boredom may be preventing us to climbing the hill all the way to the top? Being aware of this phenomenon helps when we get the urge to abandon projects for something new and shiny. We can also:

  1. Be intentional about when and how we end projects by starting projects more thoughtfully. We can timebox a project to producing some measurable output that is in our control (e.g. I will make 20 videos, I will code these 3 features, I will send 50 newsletter issues). This can set up a checkpoint for when we can evaluate and decide whether to continue a project or not.
  2. Choose to keep going. If something doesn't turn out how we expect, debug why. If there is something else we are thinking about trying, then try it. Actually do everything we can think of to make the current project successful, before moving on to the next project.

This isn't simple. It's not easy to keep going. I like to keep the below encouraging words in mind.

The hard part is when you're doing the right thing, but the results aren't immediately large enough to feel 'real' or self-sustaining. – tiny mba

And this quote remind me of these lyrics

Though you can see when you're wrong, you know you can't always see when you're right. – vienna, billy joel

Being an entrepreneur sometimes means doing the boring stuff and keeping at it. Going further down the hike even though there are no waterfalls or wild flowers or a scenic view.

One other thing, since we've talked about habits in previous issues, one more quote to share:

The greatest threat to success is not failure but boredom. We get bored  with habits because they stop delighting us. The outcome becomes expected. And as our habits become ordinary, we start derailing our  progress to seek novelty. - Atomic Habit, by James Clear

When we see similar ideas mentioned in different context, that's usually good sign that there's something to it.

Writing Out Loud

For this edition of my writing-out-loud series, the original writing is pg's essay on early work* and how the fear of making something lame holds people back from doing great work. My reactions, or my writing-out-loud thoughts on this essay are in brackets [] below.

Paraphrasing the various recommendations on how to work around this (very rational) fear from the essay. For each advice writing-out-loud my judgement on whether or not it will work for me or share my experience already trying that advice.

  1. Overestimate the importance of what you're working on, that will compensate for your mistakenly harsh judgment of your initial results. [I think this could work to some extent. Though I don't think I can convince myself that all my work is about "changing the world"]
  2. Be slightly overconfident [I don't think this advice will work for me or anyone who works hard to have an accurate estimate of their abilities. I'm not an easy person to fool, by me at least.]
  3. Another way to get through the lame phase of ambitious projects is to surround yourself with the right people. Teachers are a special case of these "right people" whose job is to see promise in your early work and to encourage you to continue. [This is very good advice even though good teachers like that are hard to find though. I'd like to think that I aim to be this person for my programming students.]
  4. Rely on sheer discipline — to tell yourself that you just have to press on through the initial crap phase and not get discouraged. [Exactly. Sheer discipline is easier said than done though]
  5. Focus less on where you are and more on the rate of change. You won't worry so much about doing bad work if you can see it improving. [Yes! This one resonates with me. I can confirm, from experience, this works. For example, when you're starting a new habit (e.g. writing) do it daily for the first 100 days, and then once you 'graduate' to a slightly better than lame phase, you can write less frequently or slow the rate. Iterations are important, especially in the early "lame" phase. I am applying this to my recording habit currently.]
  6. Another common trick is to start by considering new work to be of a different, less exacting type. To start a painting saying that it's just a sketch or a new piece of software saying that it's just a quick hack. [Yes, this one works too. This is how I wrote my ebook last year on explanation of programming concepts. I wrote each topic independently as I got the same question more than once from different students over several months.]
  7. Try out a risky project as a way to learn and not just as a way to make something. Similarly follow your curiosity and try new things just to see how they'll turn out. [Yes this would work. But runs the risk of jumping from one 'new' thing to the next. If learning is fun for you, this can keep you busy without the outcome of completed projects.]
  8. Study the history of people who've done great work. What were they thinking early on? What was the very first thing they did? [Origin stories are popular probably for this reason. Though you're getting only the public version of any person's story. This can be interesting but not directly useful for tackling your own fear of sucking at something early on.]

This isn't in the essay but another key point from my observations is this: doing early work that feels lame is even more of a mental barrier when you are an expert at something else. Something adjacent. For example learning UI design when you're an experienced backend developer. Your mind often tricks you into thinking 'how hard could it be?',  'I should be able to just pick it up fast and design beautiful looking UI', . Ah ha, that is a trap. If you've fallen into this trap before you know what I'm talking about.

*For each writing-out-loud series, I recommend that you read the original writing if you haven't come across it before. It would also be a fun exercise to note your own reactions and then compare them to mine. If you choose to do this, I'd love to hear your thoughts!

That's all for this one. I hope I've make you think more about the role of boredom. And I hope you enjoyed the writing-out-loud series, I want to do this more often and have more conversations.

Until next time,


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