2016 Big Steps Forward


Lots of folks have been complaining lately about 2016.

Certainly, as one friend of mine pointed out, as movies and celebrities have become more prominent in our lives, and my impressionable teen years were in the 80’s, I’ve seen a lot of my childhood heroes fall away this year. This trend I’m sure will continue as I age.

But personally, since I significantly shifted my business focus nearly two years ago, 2016 has been one of the most fulfilling to-date.

Professionally, I have found my path forward into more of a consulting role with clients. This has been immensely fulfilling. I didn’t realize how much I’d picked up through my years of struggle in my own consultancy. Problems that I stopped seeing entirely because I just reflexively dealt with them. It is still hard to see them, but now I’m developing a reportoire of feedback from others who seem better qualified to put how I help into words.

Perhaps it’s my perspective from my work in the trans community, but I see oppressions and micro-aggressions in many places, they are rampant in my industry. Perhaps they are in every industry, perhaps this is simply universal. My view has widened from myself, to other trans people, to people who have chosen careers in software development, to the companies that employ them. Helping folks break down the barriers they put in front of themselves, helping them see past the small shadow they see cast beneath them to the fullness of their capability and humanity. Freeing them to courageously explore new ideas and technologies, develop their craft, this is uniquely rewarding for me.

Personally, we’ve been nesting in our home up north, improving the property and house. The uniqueness and draw of this life drives me to leap towards it. As I describe to new acquaintances and clients, “I live in a log cabin in the middle of the woods.” This is who I am, who I want to be, how I want to live life. Work is fine, but is just a means to this end. This perspective has been freeing. Invigorating.

The Trump presidency may narrow my professional opportunties, if he follows through with his promise and dismantles NAFTA (management consulting is the NAFTA window that allows me to work with companies in the US). Perhaps Canadian companies have started to catch on to this new trend of bringing software skills in-house and growing local teams. I feel like my new perspective will help me locate and close opportunities here, at the very least it has given me the confidence to pursue them.

This holiday season has been one of the most fulfilling over the past 5 years as well. Having our daughters close, minimal family friction, a further glimpse of how our family will grow in the coming years, and having my spouse’s parents much closer than ever has made for a fun family filled season. Maybe this rare 10 days (in a row!) at home has inflated my fondness for being here, but it just feels good.

This year marked 5 years into my social gender transition, the time at which I began exclusively presenting to the world in my felt gender. That was an important anniversary. The initial shock of transition has given way to slow growth and self-acceptance. Undoing half a lifetime of dysphoria and male socialization is painstaking. As sure as I was, I didn’t realize then how tentative and hesitant my initial steps were in this direction. With each step over the past 5 years the feeling that I’d done the right thing has solidified. Now it’s just odd habits and mannerisms and allowing myself to accept the woman I am, in all my geekiness, weird body shape, too-deep voice, and oddly acquired mannerisms.

I feel less fragile now than I ever have. For a few years my professional confidence carried me through the turmoil, but now I feel like my personal confidence is starting to be able to take on some of that burden. I’m not sure it will yet withstand judgement from the family I grew up with, that feels like a race against time, but I’m certainly not up for a race. I won’t suffer people in my life who refuse to accept me for who I am, so I am left wondering if we will ever speak again, and wondering if I’ll ever have the strength to find out before they’re gone. If that’s to be, then so be it. Maybe it will be more comforting for them to live with the memory of who I tried to be rather than who I actually am. That is their choice to make, not mine, and I think I’ve finally stopped feeling responsible for it.

Who knows what the next 5 years holds for me, as I get back on my feet financially, as our children continue to mature, as we try and build a life more on purpose than by how the wind blows us. It feels good.

Life could still capsize us in this little dinghy we’ve built, but it’s nice to float for a while.

The Fable


There was once a family of beavers who lived in the forest in a quiet valley. They had found a stream and made their home there, a lovely lodge in the small pond that had formed. Food was plentiful, there was work to be done, and they were happy.

Occasionally the beavers would travel to the city to see their raccoon friends, who had their own lovely home and had begun raising their family.

One day, there came a fierce storm, and a pair of old trees in the forest were weakened by the winds. One quiet night, the first tree gave out, fell into the other, and then they both fell onto the beavers’ family lodge, and in a flurry of sticks and mud, it was crushed under the water.

The home was sturdy, and beavers do just fine in the water, so the family, a bit rattled, made it to shore and thought about what to do. They consulted their raccoon friends in the nearby city.

“We didn’t hear any trees fall. Are you sure that happened?” asked the raccoon family. The beaver family stood, dumbfounded.

“Why don’t you just come and live in the city?” asked the raccoon family. The beaver family tried to explain that beavers live in lovely lodges, made of sticks and mud, in the peaceful ponds formed by their dams. Besides, what would they do all day?

“Well, there’s plenty of work here! There are so many garbage cans to tip and explore!” The raccoons really enjoyed living in the city, and their enthusiasm showed!

The beaver family tried to explain that there were few trees, and no creeks or streams that would be suitable for a dam. Besides, the raccoons in the city tended to hire mostly other raccoons, for whatever reasons. And while the beavers thought they could pretend to be raccoons for a while, if they were found out, they’d be fired for the deception. And really, they were beavers. Unmatched in their skill of felling trees and building dams. They loved the forest. It was a perfect home for them.

When the beavers left, the raccoons were distraught. They talked about the situation with the other city raccoons. Together they decided that they were responsible for providing work for the beavers, who they felt would really enjoy foraging through the garbage cans. Who wouldn’t?! There were such treats to be found!

They wanted to protect the beavers, and felt those mud and stick homes weren’t nearly as nice as their solid brick city structures, which would make much better homes for the beavers. They also talked about the forest, it was so dangerous with all those trees!

So the raccoons banded together and decided to burn the forest.

And when the forest was burned, the dams were destroyed.

And when the dams were destroyed, the city was flooded.

As the creatures fled the valley, the raccoon family and beaver family found each other along the long road of refugees.

The raccoon family was optimistic, “Just wait until we get to the city over the hill! It’s a lovely place! I hear they have lovely puzzle garbage bins – great for keeping the mind sharp, and filled with the yummiest food imaginable!”

The beaver family sighed, and hoped for a cool stream and lots of trees.

Listen to your neighbours, your friends, your family. Believe them when they tell you what makes them happy. What makes them feel true to themselves. What is hard for them.

There are people who are different from you making beautiful lives in this world. Lives to which they are entitled by their humanity. Lives that look different than yours.

Let’s learn to love each other for who we are, instead of despite.

My little writing exercise above was a simple way for me to turn this over in my mind on a quiet Saturday morning. As a software developer, I fully realize it’s a “leaky abstraction” but it was fun to write, and I hope that you found it at least a little fun to read. And I do miss my home in the forest where I hope to be again soon with my family, which probably looks different than yours.


I realized this is probably more a Fable than a Parable, so I changed the title.

Retrospective on 2015


The past year has been exhausting. I’ve never felt so much like a hamster on a wheel.

This year will mark 8 years into my transition, 5 years into my social transition, 3 years since my last gender affirming surgeries.

I’m very much at peace with my body now. The change came so slowly, I could hardly tell as it happened, but looking back at myself 10 years ago? I was a mess. Gender dysphoria had me over its knee, I was constantly distracted by it, it consumed me. It was a constant buzz at the back of my skull, pulling all my thoughts in towards it.

I did some pretty awful things to myself, the worst of which was letting an herbal supplement regime mushroom out to un-supervised self-medicated HRT. I was buried in shame. I lied to everyone, including myself about it.

Today, if it weren’t for the advocacy work that I do, I wouldn’t really be thinking about my gender at all. It’s no longer a concern. It’s even a bit awkward right now to write about it, because I have to dig up how I feel. Is this what cis privilege feels like?

Being comfortable in my felt-gender role (as opposed to my physical being) is a bit further off, but I push against the bounds of this one. Maybe it’s the feminist in me. I think that this is a struggle I have in common with many women.

I find myself drawn to communities where the struggle is ongoing, launching the Durham Region chapter of Ladies Learning Code (LLC) was a hallmark event for me here.

Earlier in the year I found my “tribe” at the Agile Coach Camp Canada conference in Cornwall. This set the stage for my courage to start the LLC chapter. It was an amazing event and I learned a lot about myself that weekend. I’d been unable to express why I enjoyed my team coaching engagements until I spent the weekend with so many wonderful coaches who shared that enjoyment.

I feel accepted by the LLC community, by the agile coaching community, and that seems to drop a hand-grenade into my lifetime of internalized transphobia. How this makes me feel is impossible to express in words. Suffice to say, I feel good.

Regular life of course is still a struggle. It’s a common struggle though, and I feel better equipped to bear it.

This year marked the launch of my first software service (primr.io) in 12 years. I’m excited for it, but I have the same fears as many entrepreneurs – will it be successful, will it survive, will people care about it. 2016 will tell me that.

What I find most interesting though, is that for years I’ve strived to figure out a product that I could build, and after the turmoil of 2014 what arose seems a merging of my social justice advocacy and my software skills, two worlds I didn’t see colliding, yet in hindsight it seems so obvious.

I fear for the social entrepreneurship bubble, it feels a bit like the popular kid in the fickle startup community. Like it was created to capture people with my core values and draw us in to the startup community and its constant search for the new megastar, constantly taunting us with promises of venture capital and government assistance. I have no interest in that endless chase.

Honestly, the reason I have what these folks call a social venture has nothing to do with their bubble and everything to do with my core values.

In the meanwhile though, it’s nice at a business level to be in the same room with others that hold these values, more than superficially. Startup practices like honing your pitch and cash management skills are universal and important, so for now it doesn’t feel too far wrong to be here. I do anticipate a falling out with the crowd though. That capitalist startup smell is present, and oh so unappealing.

At least nobody has suggested to me so far to offshore my development work. That ought to be an entertaining “conversation” for onlookers.

I still have far too much on my plate. In addition to my business demanding more of my time than it has in 10 years, launching Gender Journeys Durham, joining the CMHA Gender Journeys team in Peterborough, and launching the LLC Durham chapter, I feel like over the past few years I’ve filled far beyond the extra capacity I’ve gained with my gender congruence. I need to let go a thing or three, but focusing on the things that bring me the greatest joy will also bring me financial ruin, so I continue to sit on the fence. My latest two  joys at least cover their own costs (CMHA and Ladies Learning Code).

Thus is the lure of a social venture, work that is good for the soul AND pays well. It does still feel like I’m refusing to make this decision doesn’t it?

On the family side there’s not much change in 2015. I did attend a family picnic hosted by a cousin, none of my immediate family came (that would have been “interesting” – still estranged from my family of origin). Our oldest daughter is slowly re-engaging with us after a year of isolation. Our youngest still struggling to complete high school though she’s aging on. Our middle is past the middle of her University undergrad.

My spouse and I continue our journey, still reconciling our relationship, now with my physical changes. That’s a rough road, and not one I’m ready to share.

I don’t get to see many friends, or grow many acquaintances into friendships, but that’s OK. I have a couple friendships that blossomed in 2015 and help keep me energized, and I’ve always been a quality over quantity person when it came to friendships.

I don’t know what 2016 will bring me, but change is not only inevitable but required. My cash position needs to improve, and continuing on my current path isn’t going to do it. That’s OK though, I think it’s going to be fun!

Signed and Encrypted Email on OSX and iOS


I’m writing this as much for me as I am for you, my fellow netizen.

Signing and encrypting email on iOS is a black art. Get your incense and candles ready.

To start with, I usually use the free email certs from Comodo – https://www.comodo.com/home/email-security/free-email-certificate.php

They’re, well, free. That’s about all I can say about them.

Each year, when your cert expires, you are issued a new “private key” along with a new certificate. Every fibre of my being screams against this, but hey, most folks don’t know how asymmetric cryptography works, so I can forgive most folks for not having this same reaction as I. In my world, your private key is your golden egg. You keep that private, handle it with great care, and never, ever, ever lose it. That private key is your personal identity in digital form.

OK end of rant on that. Moving on.

When you complete Comodo’s process, you will download to your computer a file, for some reason they call it CollectCCC.p7s and that’s how it hits your downloads folder. This file holds both the private key they just generated for you, and a certificate signed against it issued by Comodo.

On OSX, when you double-click that file it opens up Keychain Access and installs nicely. At that point, Apple Mail is pretty much ready to start signing and decrypting messages from others. In fact, the simplicity here is a bit deceiving because all kinds of things are happening behind the scenes that you might not be aware of, that give you a glimpse at why the h-e-double-hockey-sticks iOS seems convoluted as frak.

In order to get that private key and certificate to iOS you’re going to have to do something that I’m still washing off in the shower. You’re going to have to email it to yourself.

Here’s how:

  1. Open your Keychain Access program (it’s in Applications / Utilities – I just use Spotlight, command-space and start typing keychain… it’ll show up there)
  2. Go to Category: Keys and find secure.comodo.com
  3. One of them (you may have a few) has an arrow that you can fold down to see your email address certificate. Make sure the certificate isn’t an expired one if you’ve been doing this for a while. And for the love of all that is holy, keep those expired certs and private keys otherwise you won’t be able to decrypt messages sent to you in years past!
  4. Right-click on the secure.comodo.com listing with the unexpired certificate underneath it, and go to Export “secure.comodo.com”. Choose Personal Information Exchange (.p12) which is actually a PKCS12 file. Enter a good password – when it exports, that’s your private key all out in the open there for anyone to peek at and steal your identity.

OK, now you’re going to have this shiny .p12 file. I hope you’re at least using SSL / TLS for SMTP and IMAP/POP, but that’s yet another story. Email that file to yourself so you can get it to your iOS device(s).


When that email arrives on your iPhone / iPad / iPod you’re going to tap it, and install it. You’ll need to enter that password you entered on your Mac, and I do hope it’s as inconvenient for you to type as it should be. I fact I also hope you mis-enter it a couple times because it’s so complicated. And I really really hope you didn’t write it down, and I only kind of hope you had to do this process more than once because you forgot what it was between saving the file and getting that email. I’m not that much of a jerk, very often.

Here’s what the screens look like as you install your certificate…


You can verify that the certificate is in place if you go to Settings / General /




Now, go to your Settings, then Mail, Contacts, Calendars, then choose the account for which you had Comodo issue that certificate, then tap Account, tap on Advanced, turn on S/MIME, tap Sign, and make sure your email cert is selected. It’s fairly safe to leave Sign to ON and sign all your emails that go out, but once in a while someone may complain about the signature attachment if they don’t understand what it is and their email program is dumb and shows it to them.

You might want to encrypt your messages by default, but don’t worry – Mail only knows how to encrypt for the people for whom you’ve explicitly imported signatures… so you won’t all of a sudden be sending encrypted email to people that can’t read it.

Here are some screenshots of that process:


And now, you’re ready to go into Mail. There’s a couple gotchas and things that just aren’t that obvious.

IMG_0117First is when you get emails from people who have signed and encrypted it, you get these two little symbols – the seal with the checkmark means it’s signed (and you can grab their signature – which you have to do before you can send encrypted email), and the lock means it’s been encrypted (only you can read it and only  where you’ve installed your key and certificate).

Email is encrypted specially for each recipient against their signature. If I want to respond to this email, I must install this person’s signature. To do so, tap on their name, then tap on View Certificate, then tap Install. Here are some screenshots:

IMG_0118 IMG_0119 IMG_0120And now, when you’re writing an email to someone you can indicate that you want it encrypted. Just tap on their name, and tap the Lock symbol that appears.

If you get the messages below, this is where things get a bit funky:

IMG_0121 IMG_0122

So what’s actually happening here, is it doesn’t know what key you want to encrypt the message using, and/or it doesn’t have their signature/certificate installed. Make sure you’ve done the procedure above to install their certificate.

Now, go to your Advanced email settings again, go to Encrypt by Default, turn it on and pick your email address.

IMG_0116 (1) IMG_0125 IMG_0126Now go to Mail, create a new email to your friend whose signature you’ve installed, tap their name, and tap the lock symbol again. This should work now.


Now you can go back to your email Advanced settings and turn off Encrypt by Default. You shouldn’t have any trouble from here on in.

So there you have it, it’s a bit of a complex dance to do this, but once you’ve done it things should work pretty good for you.

Don’t forget to drag that .p12 file to your trash, and empty your trash, and delete that email both from your sent-items on your Mac, and from your inbox (and, of course, empty your email trashes)!

Through the iOS and OSX versions, Apple has tinkered with how this all works a bit, with each release sometimes introducing a new set of quirks, but hopefully this will do us at least until the fall.

Why a Worker’s Cooperative


This past weekend I was at the Software Craftsmanship North America conference (SCNA) hosted by 8th Light in Chicago. This is a wonderful conference that each year I manage to drag more of our staff down to experience.

SCNA was a bit of a break for me, as much of my time lately has been going in to setting up The Commons Cooperative, a new organization that I’m building focused on software development services for businesses, entrepreneurs, and what I’ll call “social good”.

While at SCNA, I was having a conversation with Dave Thomas (@pragdave, co-founder of The Pragmatic Bookshelf http://pragprog.com). I was describing The Commons, and mentioned that we were proud of it being a different legal structure than most companies. Specifically, we are setting up The Commons as a Not-For-Profit Worker’s Cooperative.

His simple question was basically, what’s the benefit of a cooperative versus a partnership or other traditional business structure?

Not being well practiced in talking about The Commons, I stumbled. I found myself at a loss to verbalize why I was so passionately pursuing this avenue. Since then, I’ve been thinking about how I want to answer that question.

You see, my current business, Three Wise Men Inc. (which is being renamed to Mojility Inc.) is a standard corporation. I’ve been running this business for nearly 12 years, and we try very hard to retain a stable staff of developers. We have managed to establish a healthy collaborative culture, with people that care, enjoy mentoring others, and fit very well with the values of the Software Craftsmanship movement.

Now, I’m not the best at business development and sales. From time to time, when business is down, I’m struck with the difficult decision of when and how to lay off excess staff. I have a very hard time with this, we invest so much in our people, both professionally and emotionally. I think this is one of the reasons why our staff is so loyal, and our workforce so stable.

Now, think of the job of a CEO. As so bluntly put recently in Ruby Rogues #125 – Loyalty and Layoffs, it is this person’s job to maximize shareholder value. If the CEO does not do this, they aren’t doing their job, and should be removed by the board of directors. These are the values of a Corporation, a purely capitalistic abstraction, with the purpose of generating wealth for its shareholders.

So here I am, CEO of Three Wise Men Inc., with a fiduciary responsibility to myself as sole shareholder, to shed staff to the point of profitability.

There was my friction. These people, that form the foundation of my value proposition to our customers, that I so fervently and frequently argue are not a commodity, that cannot be bought and sold on the market, needed to be shed in some heartless savage act.

This here to me represents the fundamental difference between a Corporation and a Worker’s Cooperative. The values that drive the actions of the CEO.

The values of a Corporation are hierarchical, profit-focused, maximizing shareholder wealth. The values of a Cooperative are democratic equality, sharing, taking care of the needs of the community.

So I find myself having attempted to run a Corporation with the value system of a Cooperative.

Sure, by and large it mostly works. It’s very short sighted for a Corporation to neglect its staff in exchange for profitability. Corporations invest in people, not out of the needs of the people themselves, but the need to avoid the cost of re-staffing, retraining, reduced productivity.

It’s this alignment of values about which I find myself most excited.

The promise that I can execute, with full responsibility, using my own value system, to the benefit of our staff and customers.

And here’s the best part – I’m not alone! Every one of our workers is aligned. Not just doing their job for a paycheque, not just working for the financial benefit of some unseen group of shareholders, but working together, towards all of our common cause, for our customers, as people.

I have frequently referred to software development as a social endeavour. Now, it’s in our bones.

7 Simple Steps to a Successful Software Project


1.  Imagine an end-result in only the coarsest detail

Let’s face it, we’re all human. We can’t juggle everything in our heads, and we don’t have perfect clarity on day 1 of a project. You want to get your system in place quickly, and you definitely don’t want to waste time playing imagination games for weeks on end writing detailed documentation and pixel-perfect mock-ups that will be difficult for others to understand, and could be impossible to implement.

There is definitely value in a study of business requirements, written project requirements, and simple sketched mockups, but stay high level!

The more you layer imagined details on top of other imagined details, the further from reality you get. Write down and verify your facts, sketch out your vision, and get the ball moving!

2. Keep and communicate a clear and consistent vision

It’s OK if you realize during a project that your best chance of success means a slight change in direction.

However, be wary of too many or drastic changes in direction – pause your development until you’ve re-established your vision and reconfirmed your facts. It doesn’t make sense to continue spending time and money along any direction to which you’re not fully committed.

3. Stay engaged

Don’t send your development team away on auto-pilot. They will need your help, and you will need theirs – daily communication is healthy. As each iteration goes by, they will rely on you to imagine more and more detail on top of the code they deliver. Imagining the details on top of real concrete running software is what will keep you on track towards delivering your product.

In addition, if you see something going in the wrong direction, the sooner you talk about it with the team the more you’ll be moving towards your goal.

4. Ship

It’s OK if the product is not perfect on day 1. Call it an open beta if it makes you more comfortable, but the sooner you can get your product into the hands of your users, the sooner you will start collecting valuable feedback.

Remember, don’t imagine what your users will want, find out for sure by putting the product in front of them.

Sometimes you’ll hear the idea of focusing on your “Minimum Viable Product”, the simplest product you can build that has some value to your users. How can you fully imagine this without your users’ direct feedback?

 5. Keep the feature set small

Remember the words of Antoine de Saint-Exupery, “Perfection is achieved not when there is nothing more to add, but when there is nothing left to take away.”

It doesn’t take much effort to build something complicated, and it is very challenging indeed to build something simple. It’s compelling as the project moves forward to imagine all the extra things it could do. However remember that by and large every new feature you add will make the product harder to use, and more expensive to maintain moving forward. Be very, very sparing.

This includes incorporating user feedback. You will get a volume of feedback from your users, but don’t take it at face value. Understand where it’s coming from, read between the lines, and either discard what doesn’t align with your vision, or re-align your vision.

6. The Long Haul

Your software isn’t an island. It lives in a world that constantly changes, and as with everything it must either adapt, or fail.

If you approach the project with a single up-front budget and leave nothing for ongoing maintenance, you’re ensuring the future failure of your product – it’s as simple as that.

Some technologies will be inherently most expensive to integrate from a maintenance perspective. Right now, social platforms like Facebook and Google+ are in constant flux and products that integrate with them can carry the highest maintenance costs as they adapt to what can be weekly changes. But who doesn’t want their product to integrate with Facebook these days?

Choose carefully and with your eyes open what technologies you integrate. Some will have a far higher impact on your maintenance costs than others.

7. Have Fun

Creating software is a uniquely rewarding experience. When you can see it in the hands of your users, and they appreciate it, it is tremendously gratifying.

But also remember the journey, product life cycles can span years or decades – revisiting the path to maintain and better it should be a positive and pleasant experience. If it’s not, you’re not going to want to do it.

Everyone does their job better when they enjoy what they’re doing. Keep your vision front and centre, keep a positive attitude, treat your users, peers and developers with respect, and it will be hard not to build something meaningful.

The Chaos in the Matryoshka


Those that know me know that I’m not afraid of change. I’m a big proponent of “strong opinions loosely held”. When something makes sense, grab ahold, if you can disprove it, move along. Don’t become too attached or you’ll find you’ve turned into an apologist.

About 4 years ago I announced I was done with fixed price projects. It was the best business move I ever made.

There wasn’t really any change in the amount of money we made on each project. But the spirit of collaboration we were able to bring to customers, stopping the seemingly constant disagreements over what was included or not included, what was a bug or not a bug, just ceased for the customers that understood what we were about. Software development became fun again, fulfilling. We have delivered much better work because of it.

Of course, the odd customer (who we’ve gotten better at purging) would still want to argue these points. For whatever reason, maybe they grew up in a world of fixed-price contracts, they’d try and turn collaboration into confrontation. Try and change the terms of our engagement.

I spend a lot of time thinking about the whys and hows of this, and I think it comes down to this – they’ve become blind to the chaos around them.

Chaos is everywhere, and builds on itself. It starts with a poorly understood requirement, snowballs into misunderstood emails and conversations, avalanches into the maelstrom of shifts in understanding.

Chaos is deceiving. It wears a mask of order and alignment. The human brain is brilliant at finding patterns, and it is so tuned to the idea of patterns that it will perceive them where none exist. Countless times, a customer has presented a requirement as a simple thing, we listen, we write it down, “this should be trivial” we think. And then through conversation and examination the mask comes off. Then we find it’s like a matryoshka doll, behind each mask is yet another that appears ordered and aligned. Eventually deep enough into the project we take apart the last piece and voila, chaos.

Real life is messy. Countless times we’ve had the conversation around the whiteboard where we’ve just scrapped a really elegant data model saying “Wow, this is awful! If only this business case didn’t exist…” We just discovered the chaos in the middle of the matryoshka.

Customers tend to get this. They know their business is complicated. Sometimes they’ve been ingrained in it so long that they’ve become blind to the ways in which it is complicated, but when things are drawn out logically they tend to say things like “Yeah, I know it’s strange, but that’s just the way it is.”

The risk in the software project lies in not knowing how deep in the matryoshka the chaos lies.

A fixed-price fixed-feature contract expects the software developer, with little to no prior knowledge of the customer’s day to day business dealings, to take on that risk and price the project accordingly. They’ll take wild stabs, based on their own prior experiences, sometimes masking it in a thin veil of reason. A fixed-price contract will never reflect the true cost of the software, you’ve either bludgeoned the business into paying more than they should, or the developer into delivering more than they could afford to (or worse, they walk away).

A target-budget contract has more of a shared risk. The customer accepts that they may not have a “complete” solution at the end, but that it was fairly priced because it cost exactly according to the work that was put into it. The risk on the part of the software developer is simply that they do their job professionally, and engage the customer appropriately to explore taking the matryoshka apart.

Over the past couple years though we’ve very much enjoyed a more holistic and sustainable approach than target-budget, but that’s the subject of another post…