The mistakes list.



Q: Why do this?

After long conversations with partners, funders and friends about the social sector we felt we had to do something. So many screw ups are swept under the rug. Making big mistakes and writing shiny reports is commonplace.


Q: Are you sharing everything?

Nope. We're only sharing our clear, big mistakes that other folks might learn from and we are anonymising to protect employees, partners and friends.

The goal here is to be honestly self-critical, not create failure porn or 'out' anyone.

Q: Has this been done before?

Yes! The site is a wonderful NGO resource.

See and for the startup side.

Madness is... Foolish themes.

While making the list, we noticed some themes.


The dumb expert.

Simple mistakes, which we teach our students to avoid. Ouch.


Repeat madness.

Doing something dumb, then making the same mistake again later.



Letting our ego get in the way, thinking we are special and different.

The list.

What happened?

Late 2016: We hired a (great) staff member before we had enough work for them, then ran out of work for them and money to pay their wage all at once.

We had to let them go and it felt real crappy.

Why did it happen?

We had enough cash in the bank to wear the hire, and expected we'd need them once we won a big, upcoming grant. We didn't win the big grant. 😣

Also we just liked them personally, and figured we'd find the work to justify the hire. This wasn't smart, in retrospect.

How we fixed it.

We helped that staff member get another job at a friend's company, and gave them 6 weeks to leave. In retrospect this probably wasn't a great idea either, and we should have made the firing decision earlier.

Real talk, what actually happened?

We should have waiting longer to hire. Hire slow! Duh. We didn't desperately need this person, so we couldn't define their role well enough to make it valuable.

On the flip-side, a year later it took is 3-4 months longer to hire than it should have for another role, which hurt us in other ways. Argh!


We lost more money and time on this than we want to admit. Ouch.

What happened?

2016-17: We moved into a studio space we couldn’t afford.

It was nice to have a place to work, but we didn't think it through, didn't totally click with our studio-mates (good people, we were just too different in work style to them).

Why did it happen?

We had just won a big customer and expected to get more quickly. We wanted to be a ‘real’ company with space that people could visit, run workshops in, etc. We ended up running maybe one or two workshops and could have done most of this stuff from a co-working space or home.

How we fixed it.

We moved out. It burnt a bunch of money and time, but now we work entirely distributed. We have staff and volunteers across 4 continents now, on average.

Real talk, what actually happened?

We assumed that studio space was needed when it probably wasn't. We also had a decent-but-not-great relationship with the other company we shared the space with, which meant neither they or we got the full use of the space we wanted.

The compromise was lame for everyone.


Kinda sucked. But it all adds up, right?

What happened?

2019: We thought we would rebuild our whole tech stack in 3 months.

HAH. Yeah right.

Why did it happen?

We thought we were different and special and could build a complicated thing fast without cutting any corners. This is particularly embarrassing because we are meant to be experts at this.

How we fixed it.

We haven't yet. We're letting it take as long (and cost as much) as it needs to, and trying not to go broke in the meantime. In retrospect we didn't really have any other choice, but we still could have been smarter from the start.

Real talk, what actually happened?

I (Will, founder) failed to scope out the true size of the build. If I'd have done this up front, we'd have known how long it was going to take and planned around that.


This is a real pain. 😭

One thing that makes it feel better is that none of the work is lost, it's still great tech, it just wasn't finished in time.

What happened?

2015 - forever: We always think we can make videos faster than we actually can.

This seems to come down to overpromising things to our partners, and then eating into our own budgets to cover it up. We should allow nearly double what we do, to be reasonable.

Why does it happen?

Partly it's that we feel the same thing as everyone else: “Hold up, video costs HOW much to make?! That's completely insane!”, and then try to cut it up a different way to make it more efficient or smarter or cleaner somehow.

We also assume that it will get cheaper over time, but the opposite is true. It costs the same amount and takes just as long (if not longer), but we get a better result. But that better result doesn't happen faster or cheaper.

How we fix it.

We get more money to make good videos. This is not a great fix.

Real talk, what actually happens?

We get excited to make our videos better. Like nature abhors a vacuum, video production fills to expand the space made available. We will probably always go over budget on our video production.


This is one of the main reasons we are constantly running out of money. OOF.

What happened?

2019-2020: We started work on new tech before contracts were signed and sealed.

The contract got cancelled, the cash never appeared, COVID-19 happened, we went into debt.

Why did it happen?

We were incredibly passionate about the partner, and so eager to get the work done that everyone started working for free without contracts in place.

Real talk, what actually happens?

We assumed that the revenue come in over the course of a year that we baked it into our budgets, including spending ahead of time to build the stuff needed.

Part of this was that our partner wasn't technically savvy, and didn't know what went into building apps. They trusted us to just 'make it work', which meant we started as soon as we could, because we knew it would take two to four times as long as anyone expected, and we didn't want to let people down.

What we didn't count on was that our partner's parent organisation was a big education institution, who are notoriously slow and defensive in their decision making, and they decided to pull the contract at the last minute.

In theory, we should have known this would happen.

The damage?

Okay, so this one really sucked.

COVID-19 happened, we fell into debt and had to let go technical staff. Huge pain for a tiny team. Huge!

This also meant that the majority of our other work dried up. Not sure if we'll make it through.

How we will fix it.

We clawed our way back out of the debt by reducing overheads dramatically, only keeping core staff and taking on more service work.

In some ways, it was a wake-up call that being a tiny company reliant on really big partners is a weak position. We knew this, but that's why this is a real 'dumb expert' moment for us.


This is the biggest mistake we've made yet.