When To Ask The Tough Questions


I’ve no idea why, but there’s a certain class of information that just won’t stick in my head until I’ve heard it multiple times.

“Who’s so-and-so?” I’ll ask my wife, for the tenth time.

I’ve heard on good authority that this is occasionally slightly irritating1. Of course I don’t do it on purpose — it just seems like one of my memory banks has a leak. I have to combat this as best I can, mostly by writing down absolutely everything important. I was pondering my own inadequacies (as is my wont, of an evening) and it struck me that whilst in this particular instance it’s inconvenient, in the right circumstances there’s actually a lot of good to be had from re-asking the same questions.

If you never stop second-guessing during a project, you’re not going to move very fast, or work very efficiently. I’ve identified three different stages where it can be helpful to stop and ask some questions.

1. Before you begin

When you have a great idea, it’s really tempting to jump headfirst into it. I’ve made this mistake more times than I can count, and ended up with a lot of badly-conceived, unfinished projects that might even have been something decent if I’d only put more thought into them.

Something I’ve been trying is this: when I have a great idea (or a better-than-mediocre idea, more likely) I write it down. Sometimes, if it’s a piece of writing or some kind of project with stages, I’ll outline it as well.

Then I leave it to sit for at least 24 hours.

When I come back to it, I first ask the question: “Am I still excited about this?” If the answer is no, I shelve it for now. This helps save you from getting a day into a project and then running out of steam.

Then, if it’s still something I want to do, I try and knock it down, playing devil’s advocate, asking hard questions like

  • “Will anyone like this when it’s done (including me)?”

  • “Is it even possible?”.

If it stands up fairly well, or if I can make improvements to the plan right there, then I know I can go ahead with it.

At this stage, take it from me, it is still a really bad idea to register a domain for your project.

2. When you’re halfway through

Once you’ve done the first big tranche of work on whatever it is, this is a good time to step back and ask some more questions. Here’s where you’re going to encounter something that no one is immune to.

Sunk cost fallacy.

This is the idea that because you’ve invested a lot in a project you should honor that investment by irrationally continuing to invest in it, despite evidence that this might not be the best course of action, and despite the fact that previous investments can’t be recovered.

In poker this is called “being pot-committed”. You’ve already paid your blinds and maybe more to see the flop. Now you feel like you have to stay in, even with a bad hand, because “your money is in the pot”. The problem is: it isn’t your money as soon as it’s in the pot.

This is the toughest part to ask hard questions about your project, but if you can, it can save you wasting even more time on something that isn’t worth it. I try and ask questions at this point like

  • “Is this turning out as well as I’d hoped?”

  • “Have I gone completely off track?” (if I have, it doesn’t mean I ditch the project, but it might mean I have to re-plan).

  • “Is there an end in sight, or am I just battering at a problem to no avail?”

Sometimes, even if it didn’t turn out at all like you wanted, you should continue to the end of the project if you’re close enough to finishing. An inadequate finished result is often better than no result at all, and there’s a lot to learn from seeing something through to the end. Usually, however, you’re going to want to walk away as quickly as possible.

3. When you’re done and dusted

Almost as hard as asking hard questions during a project, asking questions after it’s firmly in your rearview is tough. You’re already on to the next thing, and the last thing you want to do is go back to something you’re probably already bored of.

Despite that, you risk limiting your growth and experience if you don’t revisit past projects. Questions that might be helpful are,

  • “What did I learn?”

  • “Is there any way I can improve this, even now, if it’s worth it?”.

I break all the rules above as often as I follow them, but I’ve found that on the odd occasion where I do follow my own advice, I feel a lot more confident about what I’ve done, and what I intend to do next. I’ve also found that building these questioning sessions into my overall project plans has helped me move stuck projects along.

Now, who’s so-and-so again?


  1. Violently infuriating.