When it comes to entrepreneurs operating at the highest level, it’s hard to look past Jack Dorsey, the Co-Founder and CEO of Twitter, and Founder and CEO of Square.

We’ve seen examples of how busy it can get running one company, but how about running two publicly traded companies with a combined:

• $6 billion USD in annual revenue
• 5,000 plus employees

The big question is, how does he do it? How does Jack Dorsey actually find the time in his day to juggle two companies while maintaining some semblance of work-life balance?

When I was young I didn’t understand the value of exercise or health and how that affected my intellect. I think it was useful for me to go to all the extremes to find the balance I have now, but I wish I focused more on being healthier in the past.

Every day needs a theme

One of the most important things to note about Jack Dorsey’s daily routine is that his days are thematic. We guess that when you have so much to tackle, it might make sense to break your day down into this kind of manner.

In the past, he spoke to Fast Company about this, and he remarked:

All my days are themed. Monday is management. At Square we have a directional meeting, at Twitter we have our opcomm [operating committee] meeting. Tuesday is product, engineering, and design. Wednesday is marketing, growth, and communications. Thursday is partnership and developers. Friday is company and culture. It works in 24-hour blocks.

On days beginning with T, I start at Twitter in the morning, then go to Square in the afternoon. Sundays are for strategy, and I do a lot of job interviews. Saturday is a day off.

That’s a very interesting take, and shows just how important it is for days to have a difference. Instead of trying to do everything day-in, day-out, Dorsey appears to have found a straight-forward way to make sure his days are balanced out.

Develop consistency

At the same time, though, Dorsey has in the past made it clear how he thinks it’s essential to have consistency in life. For example, he goes to his bed at 11PM, and sleeps until 5AM.

Then, he enjoys a quick 30-minute meditation session, followed by a 20-minute workout. Then, he gets a coffee, and heads off to work.

No matter the theme of the day, this is how he makes sure that his days are going to start. That’s quite a lot of information and detail to try and stick to.

I look to build a lot of consistent routine. Same thing every day.

What it does, though, is it creates a clearly regimented time gap. You know yourself how easy it is to sneak a few extra hours of you time at night, only to feel it when you are barely at 75% of your capacity the next day.

With this kind of consistency in planning, though, you make sure that you spend way less time making it up as you go alone. We’d imagine that this is probably one of the reasons that he can actually manages to handle running tow businesses of such incredible, demanding scale.

Have clear metrics

One thing that we did notice, too, was that Dorsey seems to have a very strict methodology for measuring the success of his companies. As you might imagine, trying to run two companies as big as Twitter and Square could lead to a lot of analysis.

You could probably spend all day just looking at metrics, given the scope of data that is likely to be available.

However, that is not really a good idea. Instead, Dorsey looks to break down his focus so that he can look at certain factors. For example, his metric for Twitter is usually built around if people are using it daily or not.

If we can perfect one experience for one individual, we can scale to every single one of the 7 billion people now inhabiting this earth.

It’s a very important factor in being able to actually analyse what a business is doing without getting lost in it. by knowing what you measure as the most important metric for building a business, you can then spend a lot more time doing what you want to.

By removing the need to analyse every minor and major function, instead having a solid metric to rely upon, you can get a lot more done during the day. That’s quite an important part of running two major businesses without losing your mind!

Splitting time appropriately

Another major part of what Dorsey does is making sure that he spends enough time at both companies, not just one.

So, he will spend a fair amount of time between Square and Twitter – four hours a day every Monday, for example. Having that kind of time split is vital, as it could be easy to lose all day to just one of the companies.

By forcing that split, he ensures that he needs to rely on others to help him run the ship and keep things moving along as neatly as is possible. That delegation and ability to split time is one of the main reasons why both companies are so hugely successful.

Without Dorsey trying to be involved in every step of the process, instead trusting those who he knows can do the job, he can spend enough time to make a difference daily to each business, without it getting too much for him.

The fact that he has both of his companies set across the street from one another definitely helps. Now, it’s much easier to split time without having to lose out on valuable moments due to transport pains.

Staying connected

Lastly, another key factor in the life of Jack Dorsey is relying on leadership. He’s heavily connected to the leadership teams at both companies and allows them to do a huge amount of the work that he would normally have taken on.

This means that he has a lot of potential time on his hands as he has such a trusted team who he has such a strong connection with.

Consistency, splitting time well, delegation, and trusting others. Even despite all this, Dorsey seems to work as long as 18-hours in a day.

That’s a busy day: but imagine how busy he would be if he didn’t have such a solid structure?

Despite having found quite incredible success, Dorsey appears to have found a formula that allows him to manage it all in his stride and enjoy his own success. To us, that sounds like the perfect way to balance the grind!

A healthier lifestyle ultimately makes me more creative and allows me to think more cohesively.

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