The ability to ask for help is, contrary to common sense or at least evolutionary wisdom, a skill that must be worked on all the time. We must continuously pay attention to ourselves so we notice when and where we’re struggling. We need to examine those struggles and determine if they’re worth enduring, addressing, or ditching. And, whichever option we choose, we need to figure out if we need help to achieve it.

And then, if we do need help, we need to ask for it. We need not to criticize ourselves for not being able to do it on our own. We need simply to identify from whom we need help, and we need to ask for it.

It’s very, very hard to do.

image of woods

Recently, Sister Diane over at Craftypod wrote about something related to this, in a business context. She didn’t address asking, specifically, but focused on creating what she calls “good exchanges” with people in her audience. But what she’s saying, to a great extent, is that she needs to ask her supporters for specific kinds of help. And sometimes, she needs to actively sell her wares and services.

In business, the line between asking and selling lies in a wide grey murk, especially online where so much business relies on blogging, podcasting, pinning, and other activities of free content creation and curation.

Diane relates the issue specifically to the kinds of creative businesses that deal frequently in the dissemination of free content, and how important it is to ask people to buy our stuff in the context of our free content. The free content is, after all, a part of business. Which means it must be used to accomplish something business-related.

I suck at asking people to buy stuff, especially the stuff I make and do. I’m the best salesperson in the world if I’m selling an idea I believe in or someone else’s brilliance. But I have a very, very hard time saying, “Please subscribe to my newsletter,” for example. Because it’s hard to say that I write something I think you’ll like, and in fact, that your interest in it is the one thing that permits me to dedicate the time to continue making it. And in all honesty, that’s only a part of it.

Even more than asking you to read something I wrote, it’s hard for me to ask you to help me do my work. Since my work generally consists of ideas, it’s not like what I need from you most of the time is to buy my stuff. My work is either a service, like editing or copywriting, or it eventually results in a product, like a book. And it’s a book that’s on my mind these days, since I’m writing one. It takes months and months for me to gather, organize, butcher, smoosh, cajole, hash out, reconfigure, hack and otherwise make sense of the ideas that will eventually comprise the product I’ll do my best to sell to you when it comes out.

It’s hard for me to say, “Please subscribe to my newsletter or read my blog because I really, really want to hash out some ideas for the book, and I value your opinion and I’d like to know if these ideas resonate with you.” If I hear crickets after I share something I think is great, that’s intensely valuable to me. If I get hate mail, likewise. If I get thoughtful responses, all the better. If people share it with others, I do a happy dance.

I can’t expect to succeed in my work if my work’s success depends on other people reading it, buying it, responding to it and sharing it and I suck at asking people to do those things.

So I’m going to ask more. I’m not going to badger or become a snake-oil salesperson. But I do need your help. I need your conversation to keep me thinking about things that are important to all of us. I need to know you’re interested, because it motivates me to write more. I need you to buy my stuff if you enjoy it, so I can afford to spend time making more of it. I need your honest feedback when something I say doesn’t sit right with you, so we can both come to a deeper understanding. I need your praise because I’m a human being and it makes me feel good to know I’ve made you happy or made you think or convinced you to try something new.

So that’s the gist of it. How do you handle asking for things in business? And how does that relate to selling?

PS I can’t stop listening to Serena Ryder. I’m not alone, am I?

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Isaac B Watson

I mentioned this to Diane as well, but I’m on a similar journey, largely in learning to ask for [financial] support for Maker’s Nation. I think a lot of it has to do with the fiercely independent nature of what we do. DIY culture and all. So it’s a learning experience.

I would also caution you not to dismiss something simply because all you hear are crickets. Yes, you need some way of gauging the merit of your ideas, but the general populous of the Internet won’t always be there for you. Instead I would highly recommend an inner circle—a cohort of your peers that respect you most and will provide honest feedback and serve as a decent thermometer should the ether swallow up an otherwise great idea.

Also, I miss your presence and energy. I’ll take whatever I can get from Twitter and your blog and email and such, but damn, I wish we were present in the same city!

Nancy Cavillones

For me, it’s a confidence issue! Not just feeling confident about the stuff I make but feeling confident that I can keep up with orders, if I decide to branch out beyond my circle of friends. Or even feeling confident that I won’t get bored and distracted. LOL


Great article and question you’ve posed here (and you’ll see in a few hours that it’s been included in the link love roundup on my main site ( as a top business link of the week.

It’s definitely really hard to figure out the right balance of asking for things in business, including all different types of help and support, and using that to sell products so that you can support yourself. One thing I think is great is the Kickstarter or Indiegogo model where you are asking for support for a specific thing and you’re explaining exactly what you’ll be offering in return so that it is clear that it is (hopefully) a fair exchange. I believe that a lot of people want to support us in our solopreneur and small business careers but need to feel like they’re support is appreciated and like they’ve really invested in something that they can be a part of over the long haul.

Laura Nelkin

It is such a balance, isn’t it? The art of asking? I am constantly considering the balance between badgering and sharing… on one hand how can people support your work if you ensure they know what you are up to? On the other hand, if you sound like a broken record you loose your authenticity and become a marketing machine… and really, sometimes? I just WANT TO KNIT!

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