Change Catalyst with Shanna Mann: Strategy & Support for Sane Self-Employment

≡ Menu

I just finished Amanda Palmer’s The Art of Asking, and I love it.

I don’t know a thing about her music, her eyebrows offend my aesthetics, and her lifestyle would be enough to give me a nervous breakdown, but I will love her forever for this beautiful book.

(Also, her account of Neil Gaiman falling in love with her is the most tender thing I have ever read.)

The Art of Asking, in case you weren’t around when it was ridiculously (and, apparently, legitimately) hyped, is about a way of life that involves more asking, more sharing, and ultimately, more connection.

I know, it sounds terribly woo, that’s why I thought I would never read it.

One thing Palmer says is that after her TED talk, thousands of people over the years have come up to her and told her that they were bad at asking for help.

Amanda herself, titular Queen of Asking, is bad at asking for help too, when it really matters to her. The book opens on the day of her wedding to Gaiman, needing a bridge loan to pay her staff until the next tour begins, and not being able to bring herself to ask her husband, who wants more than anything, to help.

There are many non-intuitive things in this book that Palmer has given me anecdotes to share in the future, things I’ve figured out on my own and practiced myself.

For instance— asking for a small favor is a great way to start or cement a friendship. Even a large favor works, if you have the cajones to ask.

It works for a few reasons.

  • The first is that giving makes people feel so ridiculously good, it’s like you’re doing them the favor.
  • The second is that it ratchets up empathy— everyone hates asking for help, right? So when you take that step, make yourself vulnerable, peoples’ heart goes out to you. Then that empathy triggers connection.
  • And the third reason is plain old social psychology. Subconsciously, the fact that they did you a favor means you deserved it, and if you deserved it, you must be Good People.

What if I’m asking too much?

This has always been hard for me to express, because when you mention the concept, people can immediately recall someone who asked for favors TOO MUCH. Favors that were out of proportion to the situation, that they couldn’t or wouldn’t fulfill, people without the social grace to leave them an ‘out.’ You know. THOSE PEOPLE.

Palmer weaves anecdotes that illustrate the difference throughout the book. When she was in her early 20s, she busked as one of those “living statues.” Later on, she shared the experience on her blog and one commenter said that he didn’t mind giving money to buskers, but not to beggars. In his mind (and in the minds of most of the comment section) there was a big difference between ASKING and BEGGING.

Palmer believes that the difference comes down to the sense of exchanging value. When paying buskers, you are thanking them for your entertainment. When paying homeless people, don’t have an exchange of value. If you give them money, it is because you’re seeking to alleviate their misfortune— an object that is cheated when “fake beggars” set up shop. That’s why people find the practice so outrageous.

Asking is a kindness.

Later on, she talks about her friend Anthony, a professional therapist, who then falls gravely ill. Not only does she continue her practice of laying her problems at his feet (her words), Gaiman also falls into the same habit.

In general terms, this is an unkind act. This poor man is sick! Give him a break! But in fact, it is a thing he loves to do, and practically the only act of service he can offer, sick as he is. So continuing to make these asks is in fact the kindest thing she can do.

We like to do things for those we love. Many people strive to be stoic and independent and not rely on others, but in doing so, you rob people of the opportunity to show their love for you in a tangible way. This is not just your family members, but your friends and perhaps your audience too.

This all makes sense so far, right? I haven’t lost anybody, have I?

And yet, in practice, this can be terribly, terribly difficult.

Three ways that I’ve seen this play out:

  1. I don’t know what to ask for. This is most common for grief and depression, but it happens pretty regularly to me during times of general overwhelm. I don’t know what to ask for, because what I’m essentially wanting is the situation not to be as it is. Or at least for me to get some space to breathe. And no, I don’t even have the wherewithal to explain all this. (After someone experiences a loss, you’re supposed to figure out things to do for them without them having to figure it out, and so the onus is always on the person who wants to help.)
  2. I can’t ask yet, I’m not desperate enough yet. This is just poor strategy! Desperation may force unwilling help, not the cheerful aid that would most salve your dignity. Not to mention, you’ve suffered needlessly for a long time before reaching the arbitrary definition of “desperate enough.” Start asking as soon as you think you know what would make things easier, but leave it open-ended and provide a graceful exit for your asker. This usually involves laying out the details of the situation and asking the other person if they have any ideas. You can ask for a specific type of help if you’re short on time (or you need something simple like a ride home from the dentist after a root canal.)
  3. I asked. That person said No. I was stupid and wrong to ask and I’ll never make THAT mistake again. This is like walking into the casino, going up to the roulette wheel, and putting your life’s savings on red 36. You put it all on one roll of the dice, and you hadn’t even been in training!

It’s hard to ask. But it’s very rewarding. It forges connections, it strengthens bonds.

And it’s the type of soft skill that it’s very good to be good at. You want to be graceful. I hate to ask, or at least some part of me does.

But another part of me knows that an ungracious ask is kind of the worst of both worlds. So if I’m going to ask (and I’m going to, because I want the benefits that come with it), I’m also going to be gracious about it.

  • Whether the ask is big or small, put yourself in their shoes. Does it delight YOU to be asked for a testimonial? Then you can probably assume that most people also like that their opinion is valued, so stop whinging about what an imposition it might be!
  • Leave a graceful out. Some people find it impossible to say ‘no’ to requests, and while their lack of boundaries isn’t really your problem, it’s not good karma, so make sure there’s some sort of graceful modifier that lets them know that it’s not a big deal to turn you down.
  • Be open to possibility— sometimes you’ll ask one thing and get a counteroffer. You can assume that this is what that person really wants to give, so if you like it, TAKE IT. But if it doesn’t work for you, be gracious in your thanks.

Ultimately, asking comes from a position of strength, because it shows that you have the fortitude to be vulnerable. And it’s a muscle that anyone can strengthen.



It’s been such nice weather here lately that I find it rather difficult to get to work. It makes me think of a common question that I receive: “Why does motivation wax and wane?”

I think almost everybody wants to experience a state where they work like a machine, where they behave a certain way, and they produce certain work. In that way, they can feel like they’ve achieved productivity, or success, or at least not feel like a complete failure.

So I see a lot of solopreneurs who suffer from insecurity about their productivity or lack thereof. On one hand, it makes sense that you should be hard on yourself because the buck stops with you. There is no one else to pull you up short when you’re misbehaving. But on the other hand no one else praises you either. No one but you can really assess w dohether it’s time to take a break, or you need to power through your work. So you have to be balanced in this kind of thing.

When we ask why motivation waxes and wanes it’s clear that the expectation is that it shouldn’t. But why do we think that? It would be like asking, “Why is there weather? Why isn’t it sunny every day?” The world is a complex interplay of forces that affect your productivity as much as they do the weather.

Is it so crazy to think that working might not be the thing you want to do most right now?

For instance, right now I would dearly like to be outside digging in the dirt. It’s been a long time since I got to dig in the dirt, and the weather is perfect. Hence, being outside is more attractive than sitting at my desk, no matter how much I enjoy the work. This seems obvious, but you would be surprised how often this is overlooked.

Here’s how you usually see it go: Someone says, “Help! I’m not getting enough done! I set my goals and I’m failing at achieving them. I just can’t get motivated.”

And then you look at what they’re doing and it’s A LOT. And as a result, they’re nearing burnout.

The project itself, while important and necessary, is also usually large, stressful, and becomes the straw that breaks the camel’s back. Some might call this lack of motivation Resistance. Personally, I call that self-preservation.

It’s pretty easy to deconstruct lack of motivation, when it isn’t you personally involved. We are predisposed to be generous to our friends. For some reason our generosity does not typically extend towards ourselves. But you can ease this process by imagining what your best friend would tell you. I give you permission. (For some reason people seem to need permission to be as nice to themselves as they would be to someone else).

Tracking the forces that affect you

I’ve been keeping a time log of what I do in a day. It’s pretty simple, since I break the day up into blocks. At the end of each block before I take a break, I write down what I’ve done. I also keep track of what time I got up and how I slept.

I’m aware that this is hard-core nerdery, but it doesn’t take much time, it’s very satisfying, and it allows me to track cycles in my productivity. Using this method I’ve been able to see that I can be productive for a certain number of days, and then I have a couple of days where hardly anything gets accomplished. There are a few reasons for this:

  • Sometimes I need a break. I frequently work weekends with the book business, which means that by Wednesday or so during the workweek I need to expect that my energy level will be low.
  • Sometimes accomplishing things is about preparing for your work. This includes strategizing, researching, planning, and setting up. On days that include a lot of those types of activities, little seems to happen, except that I can note, “prepared to do X.” Preparing for a new project can take days, but it does not really allow you to cross anything off your to-do list.
  • Sometimes you reach a lull between projects. The correct thing to do here is to take a break. Most people want to keep pushing, including me, frequently. But you need to understand that this is a natural break, and if you don’t take the natural break when they’re presented, you’ll be forced to take one at a much more inopportune time.
  • Sometimes my RAM is full. In the last couple of weeks, we’ve had a few developments which have meant that I need to take some quiet time to consider their implications. It seems a poor use of time to sit down and write my thoughts out in my journal. However it’s only by laying out the new facts of the situation that I am able to see the possibilities clearly. I can tell when this is happening, because I spend much more time pointlessly clicking through social media, wanting to relax, but being unable to. Sound familiar? Any time that happens I know I need to regroup.

So I guess the question is not why does my motivation wax and wane?, it’s why do you think it shouldn’t? And to be fair, what we really want is to take one of the more unpredictable aspects of our lives, and get rid of it. Just like weather.

Just like the weather, you need to plan for it. You need to anticipate it. You need to not take it personally. The weather just is.

But, like bad weather, you can make use of the rainy days to do the things that wouldn’t otherwise rate. And when the sun shines, you can REALLY take advantage of it. I’ve found this to be far more productive than heroically trying to ‘turn around’ a low-energy day.



Here’s what I’ve been thinking about. I’ve been in this game for about 7 years now. During that time, I’ve seen some really neat ways to live. I’m not just talking about the woman who used her Filipino heritage and wasn’t just an expat but lived like a local in the South Pacific. I’m not talking about the numerous people questing across the world. Although they are cool, I like a more prosaic adventure.

  • People who unschool their kids
  • People who buy a homestead and live close to the land
  • People who patch together the most unlikely income streams to create a delightful life for themselves

I know one family who lives in a camper van with their daughter and travels the US sampling the wares at 3rd wave coffee shops. Both parents work as freelance writers.

There’s also a service aspect to lifestyle design that I think gets overlooked. I know a web designer who is passionate about  supporting women in technology and she gives a lot of her time to her local Lean In chapter.

You’ve no doubt seen numerous bloggers support things like Charity: Water and Pencils for Promise. But I also know people who beat the pavement in support of political campaigns, or who campaign on behalf of worthy causes like food wastage.

And that’s even leaving aside the enthusiastic hobbyist to spend their time in local Makerspaces or volunteering in Big Brothers/Big Sisters. I know entrepreneurs who keep bees, entrepreneurs attempting to bring their homes energy neutral with solar panels, permaculture enthusiasts, eco-tourism enthusiasts, bicycling enthusiasts; the list goes on and on.

This… isn’t a series of isolated weirdos

It was several years ago that I had my first client who came to the realization that she didn’t want to grow her business so much as get it to the point where she could focus her attention on volunteer work. Since that time I’ve been more attentive and I’ve noticed that lots of people have plans for what they’ll do when the business isn’t such a needy time suck. And lots of other people are already doing it.

If you’re deep in the weeds with your business, let me just sketch a quick picture of what this looks like:

  • You’ve been doing this for quite a while, to the point where you don’t really think about how to do things, you just do them.
  • You’re well established enough that you don’t need to work too hard to find clients. At this point, it only takes a few phone calls to scare up work or reorders. If you’re more of the mailing list persuasion, this means that you’ve sold enough stuff to pretty much know how much to expect from a launch or from ongoing sales.
  • Although you still occasionally feel the stress and fatigue that comes with owning your own business, for the most part the feast and famine cycle is behind you.

Now what?

For a long time I figured that people would just start another business, because that’s what I do. And some people do. I especially see people move from freelancer-style businesses to consulting-style businesses. They are usually either moving up the ladder to more rewarding work, or they’re moving from an active form of income to a more passive one.

And some people do something else.

It took me a long time to see this as a patterns because that “something else” is so varied.

Spend more time with family, of course, including home schooling and unschooling . Travel for sure. But also…

  • Learn blacksmithing
  • Become deeply involved in their local youth center
  • Start a craft blog
  • Delve into the world of foodies or homebrewing

That’s when I realized I was looking at the vanguard of a post-work society.

Post-work (or post-labour) is a society where fewer people need to work and yet living standards keep rising.

For a long time academics and futurists have posited the idea that once people’s needs are met they will stop working so much. And for decades that has rarely been the case. Between consumption-based economic drivers, and women clawing their way into the workplace, jobs=money=power.

But now the economic tides are shifting. With fewer cushy corporate jobs and more gigs, a lot of people are finding that the trade-off for a job is too high. They want too much of you, and they give too little back. So people start businesses. And they decide not to get big. They decide to go for enough.

And then — and here’s the really weird part — they do whatever they want.


What’s the world coming to when people don’t chase the next promotion, the next race, the next bigger house? And whoever would have thought that some of the people first on the bandwagon would be the entrepreneurs? Aren’t we all supposed to be killing ourselves with overwork?

I’m sure you don’t read my words to hear about economics, but I find it really interesting. I have long believed that knowing how to build a business is the most empowering skill you can have — you’re literally MAKING money — but it’s also pretty neat to realize that unlike the capitalists of old, we’re taking that power and doing something other than building empires with it.