Unschooling while running a business

For the beautiful Ali Luke, who requested a post about unschooling while running a business.

If we’ve never met, and you got here because some lovely unschooler forwarded this to you, hello, and welcome! I’m Naomi, one half of Naomi-and-Dave. I’ve been running IttyBiz since 2006, and we’re unschoolers. The boys - Jack and Michael – are 7 and 15.

So. Unschooling and business. Here’s what I’ve learned so far.

1. Embrace multitasking.

There is a lot of advice out there saying that when you multitask, you’re less productive. I would agree with that. Single-minded focus on one task at a time is, in many peoples’ experience, the most effective way to get things done.

When unschooling, multitasking is often the only way you’re going to get anything done. So the question is not “is unitasking better than multitasking?” The question is “is multitasking better than getting nothing done whatsoever?”

When you have twins or triplets or quads, you would snort milk out your nose if anyone ever told you not to multitask. The very idea would be hilarious. Well, think of your business / unschooling combo as having twins. Upgrade it to triplets if you’re on social media. Quads if you do client work.

(If you actually have twins, triplets or quads, I take my hat off to you. Or I will, if I can ever find my hat. My son made a bed for the cat out of it – yes, at the office – and I haven’t seen it since.)

2. Lack of order does not mean lack of rhythm.

Most of us, on one level or another, dream of a day when there will be order. We have different visions of what that order looks like, but there is an idea, fueled by the self-help industry, that one day, if you tweak this and change that and ditch the other thing, the chaos will stop and a semblance of order will reign.

The more we focus on what is not orderly, the more we see a lack of order. Peace can be found if you focus less on orderliness and more on rhythm.

Focus on the cadence that’s building, not the order you see on Pinterest.

3. Hard deadlines are probably best avoided.

When you don’t have full advance knowledge of how your time will be spent, it’s probably a good idea to avoid making commitments that require committing blocks of time, even small ones. If you’re going to write a book, by all means, write a book. You just might want to reconsider splashing the launch date all over the internet.

Less deadline, more guideline.

4. Learn to love the whirlpool method.

I have a theory about the world that I call “the whirlpool method”. I think of getting things done not like an ocean, with waves that ebb and flow, back and forth, all in the same place and predictably. Instead, I think of it like a river.

The river just keeps flowing, regardless of your opinion. It goes on and on and on, always forward, always changing. And in the river, there are little whirlpools, little vortexes. Sometimes you get sucked into a “let’s look up what Vitamin D does” whirlpool, and that takes some time. But then you get sucked into a “holy COW I’ve never been this productive in my life!” whirlpool, and that takes some time as well. (Sometimes you say that out loud and somebody wants to look up the origins of “holy cow” on Wikipedia and you wish you’d kept your mouth shut.)

Sometimes it’s bumpy, but full of momentum. Sometimes it’s torturously slow.

It’s all part of the river, dude.

“No man ever steps in the same river twice, for it’s not the same river and he’s not the same man.”

5. Give up on “shutting the office door”.

Speaking of dreams, many people – especially those who come from a corporate background – are accustomed to a time in their day when they can shut off. They say things like, “I just want to be able to close the office door, shut off for a while, you know?” Yes. Yes, I do know.

That shut-the-door time is elusive when you’re running a business. It’s also elusive when you’re unschooling. When you’re unschooling AND running a business? For many, it’s no longer a reasonable expectation.

If you would like to work towards this, by all means, work towards it. But frothing yourself up in a mess of pain because you JUST get no TIME for yourSELF helps nobody.

6. There is no such thing as a top priority.

It’s very fashionable to say, “my kids are my top priority” when we’re considering running a business while unschooling. There’s nothing wrong with that. But when everything is blended – when work and learning and eating and laundry and romance are all mixed up in the same place – domains lose their boundaries. The pieces of your life cease to be discrete, and because of that, there are no pieces to prioritize.

It’s nice to say, “I’ll drop everything for my kids”, but it’s a mercurial concept. I’ll drop everything when my children need me, yes – but they also need a roof over their head, and I’m not going to put that in jeopardy because they’re bored.

Prioritizing – nice, neat lists of the things we value and commit to, in a nice, neat order that never changes – is for people with nice, neat lives, full of nice, neat categories. If that is you, I commend you. If that is not, please don’t feel guilty.

7. Empower your children.

Give them the power to look after themselves. When my oldest was two and I was pregnant and on bed-rest, I created a zone in the fridge where he could get his own food. Everything on that shelf he was allowed to eat at any time, and most of it he could open and navigate on his own.

The more you empower your children in age appropriate ways – and you’d be surprised how much they can do, especially when you consider that for many centuries, seven-year-olds worked side-by-side with blacksmiths – the more you serve both of your goals. You will have more space for your business, and your children will be more independent and self-directed. Isn’t that one of the reasons you were unschooling in the first place?

If you have a spouse that could use empowering, do that, too. And pets, come to that. Get a dog door, a cat door, and one of those food dispenser things.

8. Work towards systems.

Dave went to school at North Carolina State University. (Dave: “NC STATE WOLFPACK WOOT!!!”) There’s a story from the college that, when they were designing the campus, instead of laying down paths right away, the designers waited until the buildings were already in place and people were already walking on the grass. When enough footsteps had worn down the grass, they knew where the paths should go, because they knew where people were already inclined to walk.

It would be a good idea to do this with your systems. Yes, work towards systems, but you might want to avoid rushing them. Systems work better when they’re based around what people do, not what you want them to do. (See: observe the user in the field here.)

9. The trick is finding things that blend well.

The other day, my youngest son Jack (aged very nearly eight) was sitting on his bed, playing a game on his iPad, cuddling me with one arm, and stroking the cat with his foot. “You’re good at doing lots of things at once,” I remarked. He replied:

“The trick is finding things that blend well.”

The simple brilliance of this statement astounds me.

When you are trying to build a business and a life and an education for your children all at the same time and in the same location, it’s helpful if you design a business that blends well with life and education. One of the advantages of unschooling is that there’s an awful lot that can fall under the heading of education, but it might be helpful to design your business with blending in mind.

Some things blend easily, like petting the cat and playing the iPad. Petting the cat while playing the viola, on the other hand, takes more doing. It might be a good idea to find the parts of your business that don’t blend well and eliminate or modify them until they do.

10. Find the times you work best.

There are articles saying smart people stay up later. There are articles saying successful people wake up earlier. My handsome colleague with the sunglasses up there was infamous for saying anything and everything should occur on your “next available lunch”. (Worry not – he has been duly mocked.)

Everybody has an opinion on when you should work. The prevailing belief system on the internet seems to be that if Jeff Bezos gets up at 5 am, you should get up at 5 am, too. Then you can build Amazon, whether you’re trying to build Amazon or not.

Find the times you work the best, and do what you can to create an environment in which those times are protected. I can’t really imagine a world in which you will attain a level of success greater than 80% on this one. If 5-7 is your writing time, do your best to protect that, but understand that 100% success is unattainable.

(About this: Talk to your children. Have a business meeting with them. Get their opinions.)

(If you’re new to unschooling, they will probably look at you like you have three heads when you first try this. They are children and have been taught by society that their opinions are worthless. They might find the process stressful, like you’re expecting a certain answer. If this happens, drop it for a month and try again. Eventually, when they realize it’s not a test, they’ll open up.)

(Also about this: As an ittybiz owner, “work” has multiple meanings, and as such, “the times you work best” will have multiple meanings also. The times you network best in social media may not be the times you’re best at email, or the times you’re best at client work. The world may say “early mornings are best for writing content because then you won’t be distracted”. Maybe, but for me, it doesn’t distract, it inspires. This blog post came from an email I got… this morning. Tomorrow’s comes from a conversation I had on Facebook… this morning. Different strokes, folks.)

11. Practice selective ignoring.

Because of the choices you have made, almost all of the advice about business, about parenting, and about productivity will not apply to you. That’s not some rallying cry, saying, “WOOT! Look how rebellious we are! **** the system, man!”

No. It’s not that. It’s simply practical. If your kids are army brats, you should probably avoid reading child-rearing advice saying children need a stable house that they live in for years and years and years. You’re just going to stress yourself out.

Learn what doesn’t apply to you and do everything you can to stop feeling guilty about it. You will fail, of course. The objective is not “never feel guilty” or “never do things differently”. The objective is to see yourself feeling guilty, or stressed, or striving too much, and gently bring yourself back to your reality.

12. Teach them about your business.

Very young children can understand how your business works. The more they understand, the more they integrate your business into their life and worldview, and the more accommodating they tend to become.

“Mummy’s working right now” often gets an ever-escalating clang of neediness. “Would you like to help me load up this newsletter?” either gets interest and a connection opportunity, or your child running away from you as fast as they can move, generally to an unobtrusive corner where they will not be found, and therefore not expected to work.

Either way, your newsletter goes up, and the whining goes down.

(Also? Talk to them about money. “X number of people bought this class for Y dollars totaling Z in revenue, or A in profit” is much more interesting to the average greedy middle-schooler than “Jimmy and his brother both had 8 apples, and then somebody stole 2.”)

13. Ask for their opinion.

All the new stuff going on around here? This new website? The (currently ridiculous) Instagram account? The Facebook and Twitter activity? The pictures on the blog posts? The pretty roundup newsletters using a template instead of our legendary plain text? Those were all my kids’ ideas.

Things got a lot better around here when I stopped thinking I was the smartest person in the room.

One of the reasons we unschool is because we want to drop “doing what everybody says”. We want our child to have the opportunity to use their own mind in a non-regimented way. We want them to have the opportunity to be creative, to think for themselves, and to reject “the way it’s always been done”.

As a result, your unschooled child is the most unsullied mind you will ever have access to. Mine it.

Thank you so much for reading.

If you know someone who might enjoy this – an unschooler thinking of starting a business, maybe, or an ittybiz owner playing with the idea of unschooling – we’d be delighted if you shared this article. Thank you!

About the author: Naomi Dunford started IttyBiz in 2006. In her free time, she likes to… ha! Free time. You’re adorable. Learn more about her here and catch up with her on Twitter or Facebook.


In our summer business planning class, we ask people to select an Area of Devotion – like lead generation, or building up a back catalog, or improving conversion rates – and then set a goal for that area. Then we ask, “What does success look like for this goal at the end of six months?”

The reason we ask this question is because we want them to come up with a specific goalpost that will feel satisfying to reach.

It’s like when you’re cleaning up for company to come over – if you don’t know what “success” looks like, then you’ll never feel like you can stop cleaning. You’ll always feel pressure to do more, or stress about what’s left undone. And we’re kind of shooting for neither, here. Specific goalposts are necessary for closure.

The specific goalpost also helps you choose what kinds of actions to take. If “success” is taking your current train wreck of a website and making it into something that you can show people without embarrassment, then you’re going to choose things that clean things up visually and make it easier to navigate. You are not going to prioritize things like analytics, SEO, or internal cross-linking.

But – if you were just shooting for “making your website better”, you might. And that’s a recipe for angst. So we ask, “What does success look like for you at the end of 6 months?”

The more you can clarify and realistic-ify your expectations surrounding success, the more likely you are to actually get things done on a day-to-day basis. Feeling like you’re succeeding makes you want to succeed at other things. It’s a virtuous cycle.

If you do not feel like you are chalking up regular successes, you will feel drained even when you are making progress.

Your brain will work very, very hard to stop you from doing things if it does not feel like there’s a point in doing them. That’s one of its jobs.

So if it feels like the work you’re doing is just a drop in the bucket, or it feels like it’s not going to make a difference, then screwing around on Wikipedia for an hour and calling it “research” is a lot more appealing than doing something that actually moves you forward.

You’re feeling bad, and your brain is going to hijack your attention and turn it to something that will take the focus off of that. Usually that’s some form of trivial distraction, or some other work-related task that feels like it has more immediate value.

This is why you end up with projects or plans that don’t get worked on for months, or even years. You experience massive resistance to taking action because as far as your brain is concerned, what’s the point? Even the work you are doing doesn’t feel like progress.

But if you give it a point, and you make it something reasonable to accomplish in a specific timeframe that also has a meaningful value … well, now things get cooking.

Try this exercise for something you’re stuck on right now.

1. Take something that you know you need to prioritize, and think about what needs to happen for it to be “done.” Not perfect, not 100% done, but done enough for you to consider it a success for now.

2. Then look at a specific timeframe and ask yourself what level of progress seems reasonable to make in that timeframe. It could be six months, or it could be a week. It could even be today.

(And when we say “reasonable”, we mean “reasonable.” Not you at your all-out best and nothing going wrong and never having to stop and pee. Think about what tends to cause normal, “this is life” delays, like sick days, writers block, hangovers and technical difficulties. And, of course, peeing.)

3. Next, take that goalpost and write down why this will be meaningful to you. Maybe it’s because you’ll feel like you’re finally moving on it. Maybe because your goalpost is a concrete deliverable that helps you get to the next step of the project.

It doesn’t matter what it is as long as it matters to you. It has to feel like real success, like something is happening that you can feel good about. And we’re talking active good, here – not “Well, I’m supposed to do this, so I guess I should.” Make it something that can leave you feeling better at the end.

(If the thing you’re doing doesn’t have an “active good,” then you can think of something more interesting that you can be doing once this is done. That can be a good way to add that value when the work isn’t particularly rewarding.)

4. Finally, think about how you’re going to feel about yourself when you get there. Take a while to really picture it. Plant that seed in your brain so it knows there’s a point to doing this thing.

The more success you let yourself viscerally experience, the more you’ll succeed in business.

Success breeds success. You’ve got to feel it to continue to make it happen. And it’s just too easy to feel like you’re failing and you’re not getting enough done to grow your ittybiz the way you hoped you would.

Feeling like you’re failing isn’t exactly a business asset. It’s a great way to shoot yourself in the foot, though.

You might want to try this way instead.

About the author: Naomi Dunford started IttyBiz in 2006. In her free time, she likes to… ha! Free time. You’re adorable. Learn more about her here and catch up with her on Twitter or Facebook.

How to love your customers

We’re bringing back some old favorites by request. If there’s anything you’d like to see us run again, please get in touch. This one is for Jenny.

Originally published December 7, 2009 as Crushed Hopes and Spicy Chicken.

I’m not a big cook. I’m not a cook at all, really. I didn’t cook before I started IttyBiz and I sure as hell don’t cook now. My husband and I eat out a lot, and if we’re not actually eating in a restaurant, somebody’s going for takeout.

One day, we were having one of those not-really-an-argument arguments, the kind you’ll often see in couples who are very aware they would be completely and totally screwed if they didn’t have each other. They’re mad, but not mad enough to risk saying anything stupid, especially in front of the kids. Since I don’t care how mad I am, I’m still not cooking, we went out to the Mandarin, an Americanized Chinese buffet.

His favourite dish at the Mandarin is called Spicy Chicken. Sometimes they have it, sometimes they don’t. It’s weird, because everything there is so static normally. But Spicy Chicken is a sometimes treat.

The way we handle the Mandarin is pretty routine now. He sits down with Jack while I go up and fill two plates – a dinner plate for me and a side plate for Jack. I come back with our food, and we switch off. Jack’s food requires preparation and organization and coercion, so I’m usually busy enough sorting him out that I don’t really start eating until all three of us are seated.

This night, he sits back down, pretty silently. (Having not-really-an-argument arguments is particularly easy when you have children who are more than happy to chatter enough for all three of you.) I go to eat and he says, really quietly and without really looking at me, “They had my Spicy Chicken today.”

Where we segue into the modern human condition

Have you ever seen those people in restaurants who don’t speak to each other? They’re not fighting or anything, they’re just generally grumpy? Same with movies. You’re in line to see a show and there’s fifty teenagers who look like they have made boredom their life’s work. Sometimes you and I are like that too. Bored. Anhedonic. Numb. Cynical.

But deep down, every person in that restaurant, everyone waiting in line, is us.  At one time or another it was our first trip out to dinner, our first time at the movies. Our excitement was enough to shatter glass. Our hope was palpable. We had not yet decided that hope was for losers.

Beneath layer after layer of disappointment, disillusionment, betrayal, confusion, rage, fear and Keeping A Stiff Upper Lip is a profound and fundamental human hope that maybe something nice will happen today.

For a moment, a flash really, I saw my husband as a fellow human being, a nice man who was looking forward with cautious hope to his favourite dinner. Probably not, but maybe.

I saw the 16-year-old who knows that his parents don’t have any money for a birthday present this year, but maybe they’ve been saving money for years and he might actually get a Mustang. Probably not, but maybe.

I saw Jack, who can’t eat birthday cake like other kids, saying, “maybe there might be Rice Krispie cakes at this party?” with that little lilt at the end that asks a question and trusts I’ll know the answer and deliver it with mercy. Probably not, but maybe.

Your customers are these people too.

I sell internet marketing products, and my industry has a bad reputation. It is generally assumed, because of my profession, that I am out to screw everyone and anyone. Not even for the money, necessarily. Just for the sheer joy of screwing someone over.

Somehow, despite this, I am blessed with a lot of very nice people who buy my products repeatedly. Considering the habits of some of my peers, it’s a miracle I sell anything at all.

In internet marketing, and I imagine the weight loss industry is like this as well, while people consciously know there is no magic wand, they continue to hope you’ll sell them one for $47. When you don’t, most of them realize that their hope was misplaced, but some become really, really angry. Then they send you emails.

I sold thirty-five thousand dollars worth of products in the last two weeks. We got a lot of email.

I am very lucky to have a lower than 1% return rate in an industry where 20% is standard and 50% is still in the realm of normal. I received a lot of beautiful letters from people who were grateful for the sale we ran and more so for the payment plan. But, numbers being what they are, we still got some returns.

If you sell how-to products for a living and you’re not in the habit of lying about what your products will do for people, your returns will generally fall into two major categories. One, your product was too advanced. Two, your product was too basic. (The guy who returned SEO School for too much swearing and the other guy who returned Online Business School for not enough swearing are, naturally, the exceptions to this rule.)

But every now and again you get a return from somebody who’s just out for blood. Maybe they want to make good and sure you’re going to refund their money. Maybe they’re pissed at you. Maybe they’re pissed at everybody. But they’ll write a treatise on exactly how much you suck and why.

We got a return from somebody who told me OBS should have been renamed Online Business 001: Business Lessons for Total Imbeciles. They told me they felt totally betrayed. They told me they were crushed.

My first desire, me being human and all, was to publish their letter in its entirety here. To rant and scream and make fun. To say that “crushed” is a term better reserved for miscarriages, philandering spouses, and lifelong pets found dead on Christmas morning.

But then I thought about my husband and his Spicy Chicken and I stopped.

This person entered into a situation full of hope. They held their breath for a moment before clicking “Buy Now” and thought, “Maybe this time it’s for real.” For whatever reason, that for which they hoped did not materialize. They are disappointed and sad, and I’m sorry for that. Who the hell am I to say what should or shouldn’t crush a person?

Inside every customer…

Inside every customer is a little child in the supermarket, hoping beyond hope that their father will buy Cocoa Pebbles instead of oatmeal, just this one time.

Inside every customer is the awkward teenager thinking that maybe, just maybe, this new pair of jeans will make the popular boy think she’s beautiful.

Inside every customer is a tired housewife who hasn’t been given anything more romantic than a tea towel for three decades, but still dares to believe that maybe that envelope under the tree has cruise tickets tucked inside.

Don’t be angry. They’re just human. Try to love them anyway.

About the author: Naomi Dunford started IttyBiz in 2006. In her free time, she likes to… ha! Free time. You’re adorable. Learn more about her here and catch up with her on Twitter or Facebook.