Unschooling and Running A Business: 13 Lessons I've Learned So Far

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. I've been running IttyBiz since 2006, and we're unschoolers. The boys – Jack and Michael – are 7 and 15. (Edit: They're now 10 and 17. Whoa.)

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. For as long as you're unschooling, 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.

There’s an old story from North Carolina State University that I love. The legend goes that  when they were designing the campus, instead of laying down footpaths 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.

9. The trick is finding things that blend well.

The other day, my youngest son Jack 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. A certain someone I know was infamous for saying anything and everything should occur on your “next available lunch”.

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. About 1 in 500 things you read about any of those things will ever make sense in your life.

Few people run businesses. Few people unschool. You're weird. And you should selectively ignore advice that can't possibly understand what your days and weeks and lives are like. You're just going to stress yourself out.

Socialization? Structure? Hell, dedicated spaces? HAHAHA.

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 The One Hour Content Plan 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 my 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!


A few other things to do while you're here:

  • The Emergency Turnaround Clinic (100% FREE!) – A re-release of our “how to survive the recession” class from Back In The Day – no sign-up required
  • The Karma Store – 12 of our products are still on pay-what-you-want, so if you need anything in there, you can still get it.
  • Unlock the IttyBiz Freebie Vault (now featuring the Money Masterclass!)
  • Naomi’s new blog – it’s about how to take care of yourself and the people you care about
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