How to send a newsletter 300 weeks in a row: know your values.

How many things have you done 300 times?

You can guarantee that most things that come to mind are a habit of some sort or another.

This week, we’re incredibly proud to send out the 300th issue of GoSquared Weekly, marking the halfway point between James writing them and me writing them.

When we caught up a couple of weeks ago to talk about doing something different for the 300th issue, what stood out the most was the power of doing something 300 times, week-on-week, without fail.

When other work we’ve done fizzles out in the early days or hardly even gets off the ground, what made this stick?

We’re all victim to this — the shiny-magpie moments of any project in its early days. But this one, writing Weekly, became a habit. A habit that we haven’t missed, no matter what.

The conclusion that we came to is that your habits reveal your values. Good habits are good because they bring you closer to what you want and who you want to be. Bad habits are bad because they do the opposite.

We all have habits. Both as individuals and as collectives — like the team here at GoSquared — and those habits reveal things about ourselves and the culture of a group.

(There’s a third, powerful category that I’m going to call Hygiene Habits. Things you don’t even think about — like brushing your teeth. They don’t need workbooks or checkboxes or apps to make you do them. You just, do it.)

Knowing your values is the foundation of habit-forming. The time-anchoring and app notifications — all that isn’t going to get you anywhere if your habits aren’t genuinely reflecting the values that matter to you.

This matters for two reasons. Firstly, knowing your values helps you prioritise the things that are most important to you. It makes it easier to say yes and easier to no. The confidence to build or maintain a habit comes when you know it’s taking you down the right road.

Secondly, really knowing why you are forming a habit makes them stick. It’s easier to flake out on an action than it is on your ‘whys’.

Your personal habits become your values.

Good habits often form under the idea that they are ‘good’ by their very nature. For example, we all know eating healthily is important — but is it part of our values?

Habits fail when they aren’t rooted in something we truly value. So, again, why is it hard to stick to habits that make us healthier? Most of us know our health is important.

Knowing that something is important is different to valuing it. To value something, you’ve got to understand why it’s important to you. You need to name it, prioritise it, and work on it.

You’ve got to treat the things that are important to you like they’re important to you.

Companies have habits too, and they become the culture.

Companies have habits too. That’s how we got onto the topic of values — I promise it’s linked. Writing GoSquared Weekly for 300 weeks is one of the habits we have at GoSquared. It sticks because we believe in giving value before asking for something back, because we enjoy sharing our knowledge and value the vote our readers gave us by signing up.

Company habits that stick are a great indicator of the values and culture of your company.

As a founder, this is hugely important information to gather because it shows you both the designed and naturally forming environment you are ultimately responsible for.

Intentionally shaping the culture of your business is done through habit-forming. Company culture and values can be just words on a well-designed pitch deck until they become ingrained in the everyday actions of every team member.

Another habit: our Friday team praise and demos.

Every Friday at 4.30 pm, we hold a recurring meeting called Demos & Team Praise. We never miss a week.

Whether the week has been good, bad, stressful or calm, we end the same way. By showing each other the work we’ve done and picking a team member to give praise to.

The praise ranges from someone completing a tricky piece of work, to someone going out of their way to help you out.

This sticks because the values underneath it are a core part of GoSquared. For me, it comes down to three things:

  1. We believe that everyone should understand the context of the company and the work we do. No one should be disconnected from any part of the business.
  2. We believe that people work better when they feel appreciated, and we believe that a strong team, communicating well, performs the best.
  3. We believe feedback is essential. Both to help us improve, and in this case of purely positive feedback, to call out when someone has done a great job or really helped you.

The habits/values exercise above works for businesses too. I’d really recommend doing this if you’re in the early stages of building your team, making any big changes, or growing quickly.

You will have a company culture. Whether it forms in alignment with what you value and believe is up to you and how intentional you are with setting habits. If you’re a founder, then more often than not, your habits become your businesses habits — the good and the bad.

Knowing your values through knowing your habits.

Habits that we stick to expose us to our underlying values — even those we might not recognise as values.

I recommend using different coloured sticky notes for this if you’re going old school — or you can use my FigJam template, which keeps everything in order:

  1. Make a list of your current habits. Push on why you chose these habits. ‘My health’ is an ok reason. ‘I want to be playing sports when I’m 70’ is better.

    For a business, recurring meetings are a good place to start.
  2. Make a list of your ‘failed’ habits. The ones that didn’t stick, and the why behind these habits. Here, it’s especially important to be specific.
  3. Look at crossovers between the two lists — are there any habits that didn’t stick but that are in line with ‘whys’ of habits that did? This might mean the ‘why’ was right, but the habit wasn’t. Or that the why you uncovered wasn’t specific enough.

    For example, if you’ve managed to play tennis as a habit and listed ‘being fit’ as the value, but you haven’t managed to go to the gym consistently. Your value might not be ‘being fit’ but instead ‘learning something new’, ‘being outdoors’, or ‘spending time with my wife’. Dig further.
  4. Start grouping your habits underneath larger, umbrella values. Themes of kept habits might unearth a value you didn’t know you had. Or even show that your company’s bad habits are reflecting a value you don’t agree with. These are important to notice too, particularly if you are doing this for your business.
  5. Take care to look at both the habit and the why. If the why feels important, but the habit hasn’t stuck — it might be that the habit itself is wrong, not your reasoning.
  6. Now, looking at the values you have on your board — where are the gaps? What values do you hold that aren’t represented here?
  7. Start to come up with habits that would demonstrate these values that you’d like to work into your personal or company routine. You can use the ‘wished for’ habits column to start doing this.

In the end, you should be left with a small group of new habits (no more than 3–4 ideally) that you want to work on, all of which have the highest chance of surviving past because they are true to what you value.

Keeping up habits for 300 weeks.

300 weeks later, your Good Habits are becoming Hygiene Habits.

You are deep in the rewards of compound interest. Well past the flattening of the learning curve.

I hope this framework is helpful! Remember you can use the board I made in FigJam, or a big wall and a lot of sticky notes.

If you’re not already, sign up to receive issue 301 of GoSquared Weekly next week!

Excited by writing stuff, reading everything, learning more, building things, and overthrowing the patriarchy.