Don’t Optimize What Shouldn’t Be Done

I’ve been on a systems thinking kick lately and just finished reading Thinking in Systems by Donella H. Meadows. Near the end, she quotes economist Kenneth Boulding:

Don’t go to great trouble to optimize something that never should be done at all.

What a wonderful reminder. I don’t know about you, but I frequently find myself going to great lengths to optimize myself in order to fit somewhere, to make something work. Without stepping back to ask—should I be engaging with this at all? Is this helping me get to where I want to go?

It’s easy to get lost in the weeds. It’s hard—but so very important—to ask if those weeds are worth the effort in the first place.

Where Did We Learn How To Ask Questions?

Questions about questions. My favourite.

At the 2021 SheEO Summit yesterday, I had the absolute joy of learning about curiosity from Chenny Xia. She took us through a few exercises to help us see what questions we tend to ask and why.

Questions tend to lead with who, what, where, when, why, and how. What’s interesting is which of those you find yourself using the most and the least. And where you learned how to do that.

For me, I seem to ask a lot of who, why, and how questions. I rarely ask when and where questions. Fascinating! What does that mean? Why aren’t I keen to explore time and place, or to orient myself in those ways?

I’m excited to explore that, and to explore one of the final questions she left us with:

“What would it look like for me to ask a diverse set of questions?”

How wonderful. And how very deeply needed in our world.

Thanks, Chenny.

Not Everything Has To Scale

If you’re interested in designing technology that “appeals to our humanity rather than exploits our physiology”, Alex Wolf is your person (and those are her words!).

In a recent episode of her podcast, The Feminine Influence in Human Friendly Tech, she talks about the impact of design that incorporates intimacy (among other feminine qualities).

Here’s the thing about intimacy:

Intimacy is important to user experience. But intimacy is hard to scale. And (most) technology needs/wants to scale.

A conundrum. However! As Alex points out, not every aspect of your business has to scale. Take Etsy as an example: the marketplace scales, the goods themselves do not.

A welcome reminder that not every element needs to be scalable for the system as a whole to experience growth.

Where Do You Spend Your Time?

Most of us spend our time here, *points above*, twenty steps ahead. Making contingency plans for things that haven’t gone wrong yet. Worrying what people will think about the stuff we haven’t made yet. Deciding what software we’ll upgrade to once we’ve reached a certain revenue, client, or audience goal.

We spend our time here because it’s easier to deal with future possibilities than present realities. Making stuff is uncomfortable. And we attempt to ease that discomfort by convincing ourselves that we can accurately predict the path forward.*

When really, we’d all benefit from spending a lot more of our time here, *points above*, in the present. Focused on the next right action.

And here, *points below*, on the big picture.

Where are you now, where are you going, and what’s the next right action that’ll move you closer?

Often, the work is shuttling between the two.


*Planning and milestones are important, ABSOLUTELY, but spending most of our time in the middle isn’t helping us. Especially when we’re focused on things outside of our control, like what people will think of us and/or our work.

What Direction Will You Build In?

You can approach building in a few different directions:

1. I want to publish a thing (blog, newsletter, podcast, etc)

What can I make within the structure of a blog? Of a newsletter? Of an Instagram account?

2. I want to share this information

What’s the best structure or platform for that? A blog? A video? A podcast? An Instagram account?

3. I want to teach people this thing

How’s that best presented? A written guide? A video course? A slide show? Hands-on learning? Which senses and learning styles should I engage and how?

4. I want to change people in this way

What’s the best container for that? 1:1 work? A course? A workshop? A book? A podcast?

5. I want to accomplish this goal (sell a product/service, establish expertise, build audience, etc)

What’s the best way to accomplish that? What’s the strategy? What’s the channel? What will I measure?

You can make things fit the structure or you can make a structure that fits the thing.

Structure and spirit. Two very important things to consider when making something new.

The Art Of Noticing

If you’re not sure what’s next, it pays to pay attention.

Your notes app, your camera roll, your bookshelf, your inbox, your social media feeds… these are all records of your attention. They reveal what you’re interested in, what you care about, and who you’re becoming. Held together, they just might point you in the direction of your next project.

But no need to rush. Just as you can’t edit as you write, you can’t discern what threads are worth following as you’re tracking them.

For now, let yourself explore.

Clarity will come in hindsight.

“Good” Rich People

For her book, Uneasy Street: Anxieties of the Affluent, Sociologist Rachel Sherman interviewed wealthy New Yorkers to explore privilege, inequity, and class. I recently listened to her discuss her research on the Vox Conversations podcast and it was fascinating. Here’s a bit that’s stuck with me:

“In a way, as long as we have bad rich people we can also have good rich people. And then as long as we have good rich people, it means the system is okay and the problem with the bad rich people is that they’re morally bad or greedy or spendy… it’s then very difficult to draw attention to the inequalities of the system.”

Rachel discusses the morality we assign the social classes, the narratives we have around rich people (i.e. what it means to be a “good” or “bad” rich person), and the importance of white people confronting their unearned privilege.

I’m all for systemic critique and analysis on wealth inequality. It’s so important that those of us who have wealth—or who have benefited from systems that make it easier to accumulate wealth—acknowledge that rather than be afraid to talk about it. Living in and from fear won’t change the system for the better, it never has.

Own your story. And see if you can use your financial stability to create financial stability for others.

Shame Doesn’t Lead to Behaviour Change, Accountability Does

This morning on her podcast, Unlocking Us, Brené Brown published an episode called Brené on Words, Actions, Dehumanization, and Accountability. I think it’s an incredibly important listen.

Horrible things are happening right now. Horrible, destructive, violent acts of white supremacy. We’re also (understandably!) seeing and feeling a lot of shame and fear.

Brené does a wonderful job of explaining why although we so want to shame people, that “othering” doesn’t lead to behavioural change. Accountability does.

Shame drives things underground, and change and accountability don’t happen there. Maybe you’ve seen that in your own family systems (pushing down or ignoring bad behaviour, pretending something didn’t or isn’t happening). Like Brené mentions in the podcast, we can see this stuff play out in systems across every level of our society, from family units all the way up to national governments.

I’ve been spending time studying how what we’re seeing now is reflective of patterns that have played out across history, and these are some questions that are helping me:

  • What happened? Name it. (Which requires vulnerability)
  • What got us here? (Curiosity)
  • What would someone have to believe to act this way? (Empathy)
  • How could we design more just and resilient systems, where accountability is baked into the whole thing? (Creativity)

I’m working hard to develop a critical lens, to be a discerning consumer and a responsible builder. I’m full of questions and uncertainty, but I can tell you this:

I will not fight fear with fear.
I will not meet shame with shame.
I will not put another human below me and call that progress.


Photo is the cover of Elise Gravel’s book Not Bad, seen in the window of Queen Books here in Toronto. Something about these words felt, you know, related ;).

Resistance vs Reluctance

Whether you’re leading a client or leading yourself, it’s helpful to be able to spot the difference between resistance and reluctance when faced with inaction.

Resistance is the fear we feel when we create something new. Steven Pressfield gives us this great rule of thumb: “The more important a call of action is to our soul’s evolution, the more Resistance we will feel toward pursuing it.” We don’t act because we’re uncomfortable with the unknown and terrified of what might happen.

Reluctance is the unwillingness to do something. We don’t act because we’re simply not interested. Often, this is due to a lack of clarity or a misalignment between goals, actions, and values. Or, maybe we’ve changed our minds and want something different!

On the surface, they both look like inaction. But they’re caused by different things and thus need different treatment.

Getting clear on which you’re dealing with can help you ask better questions, provide better support, and get moving.

The Fundamentals of Marketing

What are we talking about when we talk about marketing? To me, a discussion of marketing is a conversation about a few core fundamentals. Namely:

1. Attention

How do we get it and what do we do with it once we have it?

2. Trust

How do we earn and maintain it? What’s the promise we’re making and how do we show up to it?

3. Perspective

Having a brand means having a point of view. What’s ours? How do we express it in everything that we build and do?

And when it comes to our audience, how do they see the world? How can we meet them where they are?

4. Resonance

Good marketing resonates. It’s pre-verbal. How can we communicate in a way that leverages all of the senses, connecting us with and to our full selves?

5. Responsibility

It’s a privilege to show up and advocate for a group of people that trust you to lead the way. How can we, as Seth Godin says, make things better by making better things? How can we contribute by building something that’s inherently generative?

In short: how can we use what we have to do what we can?