A Simple 3-Step Guide To Building Lifelong Habits

Aug 29, 2023

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I loooooove self improvement books. Health, business, minimalism, entrepreneurship, money, parenting. I read them all.

I get excited to try EVERYTHING that’s suggested.

Is this you also??

Openness to new ideas and a constant drive to improve are fairly common traits of entrepreneurs.

Getting overwhelmed by the unlimited improvement ideas is a common side effect!

Whomp whomp.

How do you make new habits manageable? How do you incorporate ideas or improvements into your life?

I LOVE Atomic Habits and the many strategies that James Clear discusses:

Changing your core belief
Bundling/stacking with other habits
Doing it with a friend or group

Here’s my own 3 step process to figuring out which ideas and habits are worth keeping and which ones are not for me!

And here’s a fun story about habits, testing, feedback, and iteration over time at a startup!

3 Easy Ways To Build Lifelong Habits

1. Treat it like a test.

Think of your new habit as a test. Low pressure and low risk.

Tests work and don’t work. There’s no personal failing. It’s not about your identity. It’s a low risk, time-boxed experiment.

”Tests” work well in business too!

I often think of new initiatives as a test. Even if I hope (expect!) that it will be wildly successful, I position a project as a test to myself and others to keep the stakes low and feedback high.

Testing also makes you open to data, feedback, and analysis — from yourself and others!

How is the test going?
How do you feel?
What results or early indicators (if any) are you seeing?
What do those around you say?
Are there any metrics you’re tracking?

Too often, we internalize a habit as something we must do. If we don’t stick with it, it feels personal. We beat ourselves up. We feel shame, guilt, incompetence, fear, and lose confidence.

Maybe it’s just not the right time, implementation, or strategy for this habit.

By moving on from this “test,” we are freed up for a new habit that may be more important, aligned, or impactful.

In business, we are free to test new ideas and use money and time in a higher value way.

It’s actually hugely positive when a test doesn’t work. Now you know!

I’ve been trying to say “like” less often, take cold showers, and regularly read S-1s for years. But it hasn’t stuck. I could self flagellate for these horrific failures. Or see it as a test I ran that didn’t work.

I may try it again later or there may be something better to focus on!

Special shout out to the amazing Margaret Weniger who pointed this “testing” mindset when I was a guest on Rising Tide podcast. I had no idea. Margaret is an incredible coach with life-changing insights!

2. Commit to a timeframe upfront.

Every test needs a timeframe. Give your habit test an end date.

You want enough time to get through the initial suckiness of starting something new. There’s a learning curve, extra work, mental adjustment, culture shift, schedule accommodation, and a multitude of other things that get easier with practice and routine.

Rolling out a new program at work or trying a new workout are both a heavy lift (pun intended 💪).

For a company, a few weeks or a few quarters may be the right timeframe.

For a personal habit, it may be days or weeks.

I like to give something at least 3 weeks unless it’s clearly a no-go!

You also don’t want to do something forever if it’s not the best use of time.

So — when thinking about your habit — what’s the shortest amount of time to test it while still giving it a fair shot?

Decide upfront so you can get started on your test and focus on the habit itself.

Don’t look up until you hit that “Habit Test Done” calendar reminder!

3. Evaluate the sustainability.

I am too dang old for fads and short term fixes.

When I am in the midst of a habit test, I literally ask myself, “Would I do this the rest of my life? If not, how can I adjust it so that I could do it indefinitely?”

This may sound extreme.

But you know what’s extreme?

Sticking to habits that are not sustainable.

Sometimes there’s a habit that’s part of a finite goal. Like, riding your bike 200 miles in a weekend to train for an Ironman. Or practicing your pitch 3x/day until demo day.

These are perfectly reasonable short term habits.

I’m also a believer in a learning focus. I spent a lot (like, A LOT) of time on blogging early on as I learned. Over time, I got faster and it got easier. But I still block time every week to blog.

I take slightly fewer meetings to accommodate my writing time. That’s what makes it possible to write the O’Daily (weekly!) for the long term. (See? Sustainability, baby!)

When you force it, make it an extra thing, or are too extreme, you won’t stick with it.

Or in a company setting, when you try to force an unsustainable habit, project, or culture, your team may not stick with you!

I’m a believer in the marathon. Startups are consistent execution over years, not a few all-nighters at the end of the quarter.

You can’t “cram” for a startup or a marathon. You can’t “cram” for a habit either.

Make it consistent and repeatable in a long term way!

It reminds me of this awesome tweet from Alex Friedman:

How do you know if a habit is working?

Yes, look at the data, ask for feedback, get all the objective info you need.

But I find the most important indicator is more subjective:

How do you feel?

Questions To Ask Yourself:

How do you feel about the habit itself? Do you like it? Dread it? Find it annoying? Get excited about it?
Does the work or time feel worth it?
Is your company hitting its stride?
Do you feel more clarity or energy?
Does your team like it? Does your family like it?

Yes, you will probably have sales numbers, Whoop scores, or other “hard” info to evaluate.

And sometimes things can be beneficial without people “liking” it, e.g. children eating broccoli or your team being accountable to metrics.

But often, you’ll have a directional sense of “keep” or “go” before you see the data.

Test habits, listen to your gut, and improve in a sustainable way.

Your (startup) marathon will thank you!

What’s the most important habit you’ve cultivated? What helped you establish the habit? How did you stick with it over the long run?