Use Self-Compassion to Build Habits, You Idiot

By: Russ
Estimated Length: 12 Minutes

One day I decided I wanted to develop a habit to write more. A point of confusion for me was that I actually quite enjoyed writing. It’s one of the few activities in my life that I lose time doing (productivity nerds call this a “flow state”). It would strike me as odd then that something I enjoy wasn’t happening. I’d think about writing, I’d plan to write, and yet most days would pass and I’d go to bed with my shoulders a little more slouched than when I woke up. If I couldn’t bring myself to do something I actually wanted to do, what hope would I have to do all the other garbage in life? What I hadn’t yet considered was the role self-compassion (or its absence) played in all this.

Now I know what you’re thinking. How did I do it? How did I undergo the incredible transformation into a person who digitally sits before you with *checks*… 8 blog posts and almost just as many newsletter subscribers? Well let me tell you, it’s been a long road to the top.

I tease, obviously. It’s been a long road to the beginning, which is what this is. When it comes to sitting down and taking action on a project, my experience up until this point has been a decidedly frustrating. Perhaps more “positively maddening”. To put it gently, my ratio of ideas to finished products is unbalanced.

God I love a good idea. Give me a clean sheet of paper and some inspiration and I’ll sit there happily for a couple decades (probably more… I’ve only done it for 2 decades up to now). Nothing will ever end up on the paper mind you, but for a brief moment when I sit down in front of it, there’s a chance I won’t screw everything up and that’s exhilarating.

You can imagine how 20 years of that wears on a person. You can only stare at a pile of half-cooked dreams so long before you realize there might be problem with you as a person.

While I did in fact achieve that dream of developing a writing habit (jokes about my 8 posts aside, I do write elsewhere I swear), this post is unlikely to be a roadmap to your own success. It’s merely a retelling of the steps and stumbles I made to my most meaningful productivity breakthrough. Perhaps something here may speak to you, or perhaps not. Whatever, just join me for the next 10 minutes. What else were you gonna do? Stare at a blank sheet of paper?

The task which hinders your task is your task
It became my go-to reminder to break things down into components, find component #1, and ask what comes immediately before it. Where is patient zero?

I must credit Tim Ferriss for bringing this quote into my life (or, according to the podcast I heard it on, I must credit one of his exes for sharing it with him). For somebody prone to looking at all giant problems as exactly that, this was a key moment for me. It became my go-to reminder to break things down into components, find component #1, and ask what comes immediately before it. Where is patient zero?

I wanted to write a bunch. That’s an unwieldy goal. We can break it down into smaller and smaller components though. Write a bunch —> write a blog post —> Write a paragraph —> Open a writing app. So the absolute base-level action needed to “write a bunch”, is to just open an app. What is getting in the way of me doing that? Twitter.

Every morning I would sit down at my desk and fire up Elon Musk’s 49 billion dollar dopamine powered hate machine to start my day. The cascade of events that would ensue from there is unsurprising. Enjoyment, frustration, interest, engagement… the four horsemen of the distraction apocalypse.

4 Horses in a field, that all look like Elon Musk. It’s the 4 horse men of the apocalypse.

What if my task was not to write a bunch? What if it wasn’t even to write a little? What if my only task was to not open Twitter first thing each morning?

The power of keystone habits

Often our habit goals are overly ambitious and require massive overhaul in a way that we might not be fully prepared for. The likely defeat from such an overreach can understandably leaving us feeling disappointed in ourselves. On top of the fact we aren’t doing the thing we set out to do, we’re actually in a worse position than when we started, because now we’re frustrated with ourselves and not doing the thing.

The only hurdle you have to clear is putting on the uniform, taking one foot outside your door, and taking a breath. What you do at that point is entirely up to you.

Keystone habits are critical here because they stand as the easier part of the equation. They’re the habit that precedes the habit we actually want to build. If our goal is to go for a run every morning, this might prove very difficult to somebody who low-key dreads running. We’re starting the game on the wrong foot, and we haven’t even factored in the unexpected factors like weather, fluctuating will power, muscle soreness, and and other obstacles that might crop up. The failure rate on these types of changes is high, so how do we use keystone habits to get around the problem?

The keystone habit to running is dressing like a runner. You do not have to run. There is no problem with deciding not to run. The only hurdle you have to clear is putting on the uniform, taking one foot outside your door, and taking a breath. What you do at that point is entirely up to you.

Developing a running habit is quite difficult. Developing a habit of putting on shoes and standing outside is refreshingly simple in comparison. What people often overlook is that once we setup the keystone habit, the big bad task happens almost automatically. Want to go back inside? Go for it! What’s odd is you probably won’t.

Stop Fighting Your Willpower

If you’re attempting to change a behaviour, take a moment and ask how much of your success is dependent on rock-solid willpower. If the answer is “a lot”, your odds of success aren’t awesome. If the chief strategy to add or remove something from your life is to give yourself an aggressive pep talk, your likelihood for failure is high.

It’s important to understand what willpower is. It’s not an infinite well you can draw from whenever you need it. It ebbs and flows throughout your day, and depending on thousands of factors, it may or may not be there when you require it.

For this reason, it’s a terrible strategy to rely on when trying to overcome a bad habit or create a new one. It depletes rapidly when we’re forced to deny something we crave or start doing something we despise. Not only that, every decision we make through our day draws from the well also.

Something as simple as spending 5 minutes deciding what to wear at 7am can impact how hard it is to get on the treadmill at 7pm. Respect your brain. It’s a machine that has been iterating on itself for millions of years. No self-respecting urge will be tricked by a pep-talk or instagram motivational message for longer than a week. Those urges are strong and they can play the game far longer than you can.

Stop fighting yourself

Your attitude matters, and a lot of us have terrible attitudes when it comes to our habits. We treat missteps along the way as personal failures instead of admitting the truth: the task was the problem, not the person.

Have you ever tried to teach a skill to a child by screaming at them? I have. It felt great in the moment because I super wanted to yell at something. Successful though? Can’t say it was. You can probably get the behaviour you want if you yell long enough, but the future therapy costs will likely offset the gains.

A deranged man and his son in a family therapy session. The son is mortified while his dad wears a MAGA hat and a gun and thinks he’s fine.

When it comes to learning, aggression shows terrible results. Whether it works or not, you’re left with baggage. Most of us would agree that if you were to teach a child any skill, fostering genuine curiosity and approaching the task with a calm demeanour tends to produce excellent results.

It’s a shame all this wisdom ends up dead in a ditch when we go to teach ourselves something, isn’t it? We choose screaming and not surprisingly we end up like that frightened child, whereby even if we manage to win, we lose.

Often with behavioural change, there’s so much tension involved. We fight and  belittle ourselves for not being the way we’d rather be. It’s no wonder change is so difficult when we’re swimming upstream all the time.

Thank you, you bastard

What if we took a moment to acknowledge that the behaviour we hate about ourselves isn’t bad? Remember habitual behaviours exist to alleviate us of pain. At some point in your life (usually in youth when the stakes are high, wisdom is low, and options are limited), these behaviours cropped up to solve a certain problem. Of course not all of them are healthy or productive, but then that was never their job, was it? Their job was to help you not hurt in a given moment.

What if we took a moment to acknowledge that the behaviour we hate about ourselves isn’t bad?

This might sound odd, but take a moment and thank your habit (feel free to wait until you’re alone so you don’t look super weird). Thank the cigarette habit for all the times it gave you a thing to do when you were stressed. Thank the emotional eating that gave you a reason to go out. Thank the aversion to movement for all the times it kept you comfortable when you felt overwhelmed. Then tell them that you’ve found a more healthy way to manage those feelings, and see if anything changes. Hating parts of yourself is no way to change.

Tools to help you succeed and build self-compassion

The 30 for 30 rule

Humans are absolutely terrible at appreciating the value of exponential growth. At a base level people fully appreciate that many small things make a big thing over time–but it’s not something we see in practice out in the real world. It’s a bit like the financial rule of “buy low sell high” that everybody so confidently shares in the good times, yet when the stock market has a hiccup, everybody is stuffing cash into mattresses and bashing each other in the skull.

If you have a thing you’d like to get better at, dedicate 30 minutes to it each day for 30 days. While it feels like you’re setting the bar a little low, this is by design. It’s not taxing on our elephant, it won’t require you to disrupt your day much at all, and it might be enough to accidentally-on-purpose slip into a habit groove.

The principle here is similar to the keystone habit. In fact, maybe you’ll use a keystone habit to do the 30 minutes. What matters is that many small things add up to big things, and clearing low hurdles is an easy win that leads to bigger wins. As a bonus, 30 days is a low investment, so you are given an opportunity to notice the gains quickly.

How many times have you set out to learn or get better at a thing only to fizzle out early? Likelihood of burnout is high when we’re learning new things because the realization that the task isn’t as simple as we originally thought  drains the enjoyment from the task. By keeping things to 30 minutes only, that realization arrives more slowly, allowing you to ease into the inevitable (and crucial) discomfort instead of riding full-speed into it on a motorcycle. Without the burnout, at the end of the month you’ll have 15 hours of progress towards your goal. What’s the last big idea you gave 15 hours to?

The 2 Day Rule

Every action you take is a vote for the person you want to become. When it comes to habit generation, the 2 day rule can ensure those actions are aligned with the type of person you want to be. In the post on remaining in the present moment when the moment sucks, we learned that in the brain, cells that fire together wire together, meaning performing actions is like packing down a trail. The activity is difficult at first, but the more we do it the more automatic the brain pathways fire to trigger the behaviour. If you’ve ever practiced something over and over only to find a sudden tipping point made it feel effortless, you’ve experienced the cells wiring together.

If you’re the type of person that beats themselves up for breaking a streak, put that weight down for a moment and give yourself permission to be human for a day.

The 2 day rule ensures that if you do stop letting them fire together, it doesn’t happen long enough that you lose any progress. What’s great about this rule, is it does allow for failure. You’re allowed to break your streak or take a day off. Don’t feel like learning code one day? Completely understandable.

What you’re not allowed to do with this rule is let it slip for a second day. This strikes a balance between practice and rest. You don’t burn out from exhaustion, but you also don’t lose momentum. To let your behaviour lapse for 2 days is going to start building momentum for your habit in the opposite direction.

So break your streak. If you’re the type of person that beats themselves up for breaking a streak, put that weight down for a moment and give yourself permission to be human for a day. Not doing the thing once is not going to damage you (it may even heal you), but beating yourself up for failure certainly will. Tomorrow is always an opportunity to start again.

The monthly recap

Journalling gets a bad wrap and I’m not entirely clear on why. Maybe it’s because of the stereotype that only little girls use journals and we all have an unhealthy amount of misogyny to process? Whatever it is, you should totally stop being a little bitch and start journaling.

I’m a firm believer in the power of the journal. Typically I let my journals go pretty free-form and jazzy–I just open the consciousness valve and whatever pours out is what happens. Among one of my favourite entries however is always at the start of each month where I load up a decidedly less-jazzy template.

The template reads as follows:

1. What went really well this month?
2. What didn’t go well?
3. What is getting in the way and contributing to #2?
4. What can we do to eliminate #3?

We tend to fiercely undervalue the impact of short-term things. A degree off might seem like nothing over a day, but over a year we might end up way off course. This exercise is designed as a chance for a course correction to make sure you’re still moving the direction you want to be moving, which is towards the type of person you want to be.


One of the over-arching takeaways with this entire blog is that change is hard. Very little will change that, but there are things we can do to make it a bit easier. Self-compassion is one of those things and I see it as a critical step that tons of people overlook. If I had to wager on one thing that keeps us from getting where we want to go, it’s that we don’t really like ourselves.

One of the first steps is to recognize that nobody flourishes under distress, disrespect, and cruelty. This understanding is easy to apply to others, but very difficult to apply to ourselves. Without some goddamn kindness, we aren’t getting off the starting blocks at all, so start there.

With our new found compassion for ourselves, we can enact little steps in the way of keystone habits. Rather than looking at one giant task, we can laser-focus on the first step, and concern ourselves with that and that only.

From there we can begin building some consistency in the same way. Again, going gently will help us avoid burnout and create massive gains over time.

That consistency will allow us to build networks in our minds and strengthen the neural muscles. As always, we will remain gentle with ourselves when we misstep, and that compassion will allow us to begin again the next day instead of giving up for weeks (or longer).

Finally, we will do frequent check-ins to ensure that we remain on-course and moving forward. We have the map, and there’s no reason to not bring it out every month to make sure we’re not headed for disaster.

You’re a goddamned amazing person. You’ve survived all sorts of stuff. Trauma, recessions, pandemics, the swing music revival of the late 90s that allowed a band called “The Cherry Poppin’ Daddies” to exist and we all pretended that was totally normal and fine. Treating yourself the way you treat your friends can have unimaginable benefits for your overall wellbeing. As an offshoot of that, self-compassion can be used for all manner of improvements–habits in this case. So maybe start here. Give it a try and see if liking yourself a bit helps you do something you’ve always wanted. Should you find success there, then you can begin to entertain what else self-compassion has to offer.