You wrote a lot about asking for help without speaking about the most important aspect: Relationships.
I have a school friend with whom I spent a lot of time in the first two decades in my life and now speak with once per year. He got a PHD in mathematics and recently I had an issue where the a mathematical perspective was valuable. It wasn't necessary to ask anybody for advice and there are likely a lot of other people I could have asked. Asking my old friend not only helped with the object level issue I was having but it was also a way to stay in touch with my old friend.
If you ask a friend for help it's useful to think about how that influences your relationship with them. Is it something that makes the relationship deeper or is it something that takes away from the relationship?
Exposure is the most effective remedy for most forms of anxiety. It is also helpful to understand the thoughts behind that anxiety and consider to what extent they are valid or beneficial (there are good reasons to be anxious, but they may only justify it to a mild extent).
Many techniques can help such examination. One that is particularly appealing to me is to imagine what I would tell a close friend who is very much like me ("double standard" technique).
A slightly different sort of benefit to asking for help: it gives an opportunity to potentially start a collaboration / mentorship / friendship. I find when reading older autobiographies that important relationships often started when e.g. they read a book and had a question, but no one they knew could answer it, so they eventually sent a letter to the author of the book.
These days the internet means that asking someone is much less frequently the most efficient way to find out some information. And even if you do ask someone they're more likely to send you an email than to invite you round for tea. But these opportunities to connect with people seem very important, so I think it's good to take this into account when deciding if it's better to ask someone or work something out yourself. It might also mean we need more explicit opportunities to connect with people than were necessary in the past.
I feel afraid that my request or question will seem dumb or obvious, or that it’s a waste of their time.
1)
Do you deep inside believe that only stupid people ever ask for help? Wrong! No one knows everything. Even within their area of expertise, almost no one is best. And even the people who are literally the best can benefit from someone sharing their burden.
Asking for help is sometimes actually the smart move.
2)
There is a chance that, ironically, worrying too much about not wasting someone's time or not appearing stupid, may actually make you waste more of their time. For example, if you work with someone on the same project, and you are unsure about something, it is better to ask for their help sooner rather than later, because if you indeed were wrong, now you have wasted more of the total person-time allocated to the project.
Even the disclaimers like "hey, I don't want to waste your time, and it's totally okay if you send me away, don't worry I won't get offended, I completely understand that your time is precious" can be a waste of the other person's time. Maybe answering your question would actually take less time than listening to the disclaimer. I am not advising competely against using the disclaimers, just to keep them simple and short.
As you've no doubt noticed, our anxieties don't often respond to mere reasoning.
Two of the most common sources for this type of anxiety related to behavior are:
Narrowing it down begins with checking how you feel about other people doing whatever X is. For example, if you picture someone else bothering a person of high status by asking them for help, how do you feel?
If the response is a negative judgment, empathetic embarrassment, anxiety, etc., then it's very likely you have a learned "behavior X = bad person" type of rule in your brain.
Direct negative judgments are usually fairly straightforward to get rid of: in the simplest case, by just letting go of the rule if you no longer endorse it on any level. More complex methods for more stubborn cases include those of Crane ("releasing" technique) or Byron Katie (The Work).
If the judgment is more indirect or only applies to yourself, the techniques involved are more complex, and typically involve investigation into the specific circumstances that created the anxiety. The good news, though, is that usually some information about that will surface during the failure of the Work or releasing, which is why I try to start there first.
Successful intervention would mean that you no longer feel that particular anxiety when imagining the need to ask someone for help.
This is a different approach than the traditional one, in which one is told to fake it until you make it, i.e. keep doing the thing and maybe the anxiety will go away... eventually. Given my experience of dealing with various sorts of anxieties for years or decades with no change, I am not particularly satisfied by that sort of advice. It is definitely possible to do better: to change our minds in at least some areas, instead of just having to live with them.
I really suck at asking other people for help. I find it very anxiety inducing and aversive to think about. It sits at the intersection of a bunch of biases I have. Some part of me is convinced that I can do everything myself - that it is weakness, or being a burden to ask anything of someone else. Part of me is convinced that any cost to myself is fine, but a cost to someone else is a really big deal - a strong anxiety around bothering other people. Asking for help is rarely necessary, often I could get by without someone’s advice, or get it done on my own. There’s no urgency, and it feels much harder to value my time and welfare over other people’s. I feel afraid that my request or question will seem dumb or obvious, or that it’s a waste of their time. Especially if the other person seems high-status, or unfamiliar.
This triggers even when asking for help is the obviously correct thing to do. When I want a favour from a friend that I know they’ll enjoy giving, or could give effortlessly. If I’m working somewhere, and am confused, I feel a high aversion to asking my mentor, even though that’s the entire point of having a mentor.
Anecdotally, this bias also seems common in many of my friends. And when I’m people I respect for life advice, they often point to a general failure to ask for help. I think this is really, really dumb, and at times a pretty major bottleneck on my life. In this post, I want to make the case that asking for help is clearly the way to maximise total value, tips on getting the most out of help, and ways to be a fun person to help.
Some of the most common places this triggers for me are below. This advice applies across all of these examples, though I find it generally helpful to take a different perspective for eg asking friends for help, vs asking someone high status for career advice.
This is an annoying topic to write a blog post about, because this advice can obviously be taken too far. Some people don’t ask for help enough, some people ask for help too much. And there are many times when asking for help is not the right thing to do. If, eg, people often get annoyed with you for bothering them, then this post is not for you! And always ask, should I reverse any advice I hear? But I conjecture that this is valuable advice if you’re the kind of person who tends to insecurity, fearing being a burden and to trying to do everything yourself. And that for many people, asking for help more on the margin is a really good idea.
The first step is convincing myself that this is an issue at all. That my reluctance to ask for help is a problem, and worth putting in effort to overcome. And my core argument here is that asking for help is universalisible - that I would much prefer to live in a world where everyone asks for help, than one where no one does. You should ask for help when it maximises total value. Most of my reluctance comes from struggling to step outside of myself, and put my welfare on an equal level with other people - it feels much easier to spend an hour of my time than to ask for 5 minutes of somebody else’s. But I think this is just clearly wrong. A useful hack, other-ise: If you have something you’re agonising over, imagine a friend in a similar situation asking you what to do. If the answer is obvious for the friend, it’s also obvious for you!
Some concrete ways asking for help obviously increases total value:
Of course, it’s easy to still have anxiety around things that are obviously good ideas, but I find it helpful to dwell on these ideas. I want to be the kind of person who is able to ask for help, and to depend on others.
Another route to dealing with the anxiety is to focus on optimising how I ask for help, making sure I’m getting as much out of it as possible, to justify the cost to the other person’s time! Here I’ll focus on getting the most out of advice, as I feel like I have the most useful thoughts here. Many of my thoughts on learning from conversations, and the section on ‘asking questions’ from my post on learning apply here.
The first, and most important, is to be clear about what you want. Be easy to help! Give them as much useful context on the situation as possible. Outline your key uncertainties, the relevant high stakes decisions, your current thoughts and biases. Be clear about what you want from the conversation.
Another helpful way to think about it is to minimise their intellectual labour when it comes to being helpful. Prepare questions and topics, give them as much structure and direction as possible. On the flip side though, don’t be too rigid. You’re asking for advice for a reason, they have a lot of context and tacit knowledge that I lack. I find it helpful to point to the topics I feel most confused about, and ask questions, but let them drive the conversation if they have thoughts. Another good hack is to try to use their intuitions to find good questions or topics, eg I like to end all conversations by asking “is there anything important I should have asked you about, but didn’t?”.
Another framing: They have a lot of intuitions I lack, but those intuitions are represented in their head as tacit knowledge. My goal is to gain surface area on those intuitions - do whatever I can to poke at them, explore them, and try to build a model of them in my head. Some tips:
I’ve found it helpful to be on the other side of this, it’s so much easier to give good advice when people use these techniques on me.
On a more meta-level, a major mistake is not asking for advice in the first place, or waiting too long! If I’m eg working somewhere and have a mentor, I find it super easy to procrastinate on asking for help. I feel like I need to try everything, wait until I am completely stuck. That I’m wasting my mentor’s time if I haven’t exhausted every avenue before asking for help. Or, worse, that I need to make progress before asking for another meeting. When, in fact, the times when I am confused and not making progress can be the most useful times to ask for help. My goal is to learn, and to learn to progress faster next time. The techniques for gaining surface area can be really helpful here, trying to gain surface area on ‘I am stuck, what should I do?’ is one of the best ways to improve. If possible, I highly recommend trying to arrange regular meetings with a mentor.
And finally, asking for advice is an excellent time to seek upside risk! Don’t just ask about whatever feels appropriate, or what’s on my mind. Most of the expected value from advice conversations comes from a small chance of a big change in belief. So you should try to optimise that probability, and ask open ended questions that make this more likely to happen. Personally, I find it easy to ask about things that I, on some level, already know. And instead, it’s valuable to make a list of my key uncertainties, or bottlenecks and focus the conversation on those, eg by emailing a list in advance. Especially if they feel embarrassing, or irrational! Some prompts:
Finally, a good way to overcome the anxiety is assume there is coherent logic behind it, and try to understand what it’s trying to tell me. And for me, the anxiety often stems from fearing that there’s a cost to the other person. But, rather than flinching away from asking at all, it’s often more productive to channel this towards minimising that cost - finding ways to both reduce the cost to them, and ways to add value in turn.
Some tips:
Anxieties centred on asking for help continue to be a major bottleneck in my life. There are such vast gains from trade to learning how to appropriately depend on others, but it takes a lot of willpower to decide to do. But dwelling on the ideas in this post have helped me to get much better at this, and to do it far more often. And I feel satisfied that I’ve managed to channel this towards being a more fun person to help, and getting more from people’s time.
Worse, because deciding to ask for help takes so much energy, it’s never the default. It never feels urgent. It’s easy to macro-procrastinate about, even after internalising that it’s worth doing.
So, if the ideas in this post resonated, I hope that you ask for help more often. This is a really damaging thing to have anxiety centred on. But, further, how could you change the default of your life so that you ask for help naturally?
Exercise: Set a 5 minute timer. What are the current problems in your life? Who, specifically, could you ask for help on this? Then go and do it! And afterwards, reflect on how it went, and whether you want to be the kind of person who does this more often.