Shorts are small essays that I publish every day. They usually only take 2-5 minutes to read, and touch on all the same topics that my blog covers.

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Everyone has experienced a plateau.

It might go by other names: slow progress, languishing, stuck.

It seems like progress has stopped. More work doesn’t seem to be producing more results.

It might be a sport; your golf game, for example.

No matter how much time you spend at the driving range, you don’t seem to be improving.

It could be something at work; you can’t seem to make progress, despite spending hours on a project.

Or you realize you took the wrong direction, and have to start over.

Seth Godin calls it “The Dip”—the point where your effort doesn’t seem to be producing any reward, after an initial burst of energy and progress.

Graphic from Ben Nadel

There are a few things you can do to help push through:

Prepare for it: If you know it’s coming, it hurts less when it happens. Almost everything we do will have a tough period—a “Dip”—and planning for it helps us push through.

Bring some tools: A coach, a peer group, a mentor, a new framework—these are all tools you can bring in to provide a little jolt of energy and fresh perspective. Sometimes that’s enough to break through the plateau. Even if not, it often provides some much-needed confirmation that you’re on the right path.

Team up: Everything’s easier when you’re going through it with someone else. Try and get a teammate on board early, or find a group that’s going through something similar. A training group, or peers on a similar path at a similar stage.

It’s almost impossible to avoid a plateau when pursuing something new.

But if you prepare well, you can make it as painless as possible.

Our Health is Like a Gas Tank

Our health isn’t like an on/off switch.

We aren’t healthy one day, and unhealthy the next.

Our mental health works the same way.

It’s more helpful to think of them like a gas tank.

We slowly deplete the tank when we don’t exercise. If we reach empty, something bad is bound to happen.

The same is true of our mental health; we aren’t healthy one day, and unhealthy the next. It’s a gradual process, for both improvement or decline.

The only difference is that things get worse as our tank gets empty. Positive and negative feedback loops don’t happen in a car, but they’re real for us.

Our physical well-being can affect our mental health, and vice versa.

Poor mental health might affect our work, which in turn affects our mental health.

The gas tank analogy is useful because it helps us correct along the way.

Here are a few things you can do:

Check in: What level is your tank at? Why? How can you tell? Physical health is easier to assess than mental health. For physical health, you can test yourself, or use benchmarks and measurements. For mental health, you’ll have to use more subjective measures. How do you feel when you wake up? Do you feel motivated at work? Do you feel energized through the day?

Identify the habits that drain the tank: This is also easier for physical health. Eating poorly or lack of exercise are going to cause decline. For mental health, what things drain your energy? What do you dread doing each day?

Identify the habits that fill the tank: For physical health: what healthy meals do you like to eat? What unhealthy food can you cut? How can you make exercise or activity fun? For your mental health: what relaxes you? What feels like play to you? How can you spend more time with friends or family, or have more time to yourself?

Schedule: The final step is to schedule time for the things that fill the tank, and try to reduce those that drain it. This is easier said than done. But acknowledging that your tank is low is the first step.

Our mental and physical health doesn’t decline or improve instantly. It’s a slow, gradual, process.

The good news is that gives us ample opportunity to figure out how to fill the tank.

Better Judgment

We all judge things every day.

Other people, sports plays, the latest news. We all form an opinion.

The problem is that we often don’t have the context, or the knowledge, to form a good opinion.

It can make for good conversation, true, but when we form an opinion we get stuck with it.

We defend it, and then we seek information to confirm it. We do this all without thinking. It’s how we’re wired.

But we would be well-served to try and improve how we judge things.

Here are four ways we can be better:

Reserve judgment: We should all be a little more comfortable saying “I don’t know” and “I don’t have enough information to form an opinion.” The modern workplace frowns upon that kind of response, and while it matters less in conversation, it helps us avoid becoming attached to a particular view.

Wait: Initial impressions are rarely good impressions. Our initial impressions are emotional, and often related more to past events than the one we’re trying to evaluate. Waiting helps us put things in perspective. It helps us remove the emotional component, and really consider the question we’re trying to answer, like “was this action correct?” instead of an easier one like “do I like this person?”

Seek opposing arguments: As we start to form an opinion, it helps to deliberately seek out an opposing view. The military often calls this “red-teaming”: you assume the opposite perspective, that of the “enemy.” Figure out why the other side believes what they do. Try and prove it yourself. Then revisit your original opinion—does it still hold up?

Test some mental models: Mental models are simplifications of the world that help us think. They are never exact representations of how the world works, but they can help us see it in different ways. Inversion is one such tool: instead of trying to answer the question, ask and answer the inverse question. For example, try and figure out how to avoid being unhappy, instead of how to be happy. Repositioning the question or using some different models can help us think about an issue in a new light.

We can’t avoid judgment; it’s part of our nature.

But we do it so frequently that even small improvements can yield big results in the long-term.

Better judgment = better decisions = a better life.

I Have to Believe in the Work

I was once told that I’d be good in private equity.

It was half joke, half serious. Part insult and part compliment.

The compliment side was a comment on my pragmatism and calm nature.

The insult side suggested that my lack of outward emotion would mean I wouldn’t care about gutting businesses and firing people, hallmarks of the stereotype of private equity.

As with any great backhand compliment, there was an element of truth in each.

I do manage ups and downs well. Some combination of nature and nurture means that I can easily put things in perspective. Experience has shown me that there is little benefit to getting worked up about things.

I’ve never seen private equity from the inside. I’m sure there are plenty of good people in the industry. 

But the stereotype is of the cold, banker-types gutting a business and firing people for the sake of maximizing profits and shareholder value. For the sake of this example, I’ll assume that’s true.

I don’t think I would last long in that business, because I would have trouble seeing the value of what we were doing.

Money is great, but it’s a tool. A tool that I think is best used trying to create value. Cool software, or fun toys, or things that make our lives better.

Some of my fellow McGill grads have built a company around electric snowmobiles and jet skis. How cool is that? That sounds fun.

I work in tech because I believe in the value the industry creates. 

No other industry creates such value from nothing. 

And no, not all tech is good. But as a whole, it’s what pushes us forward.

And it’s fun! 

What’s the point of work, if not to have fun, build cool things, and provide value for other people?

It’s why I don’t work in private equity.

It’s why I have to believe in the work.

I Still Want to Build Things

When I left high school, I knew one thing: I wanted to build things.

It’s why I chose to study engineering. 

And it’s why I went into the world of tech and startups after university. 

I wanted to experience building things from start to finish.

Today, not much has changed.

I still love building things. And I still want to get better at doing it. 

The act of creation brings me huge satisfaction.

It’s why I enjoy writing, photography and video. 

There’s something deeply satisfying about taking a project from start to finish, a creation completely of your own making.

I get the same sense of satisfaction building systems at work. 

This is sometimes a difficult balance. 

It’s not always optimal to build something yourself when you have a team or other resources that could do it for you. 

But coordinating a project doesn’t bring the same sense of satisfaction.

And of course, on a longer time scale, building businesses has become a large part of my life.

Whether that’s contributing to a startup, or building something on my own, the same sense of satisfaction is there.

A business is a system too, albeit more complex, and building one can bring that same sense of satisfaction.

Many things have changed since I graduated high school.

Wanting to build things isn’t one of them.

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