Skip to content

Structuring Your Week as an Entrepreneur/Creator

David Sherry
3 min read
Structuring Your Week as an Entrepreneur/Creator

How should you structure your days/weeks/year?

In a company, you get structure handed to you.

But when you go out solo as a freelancer or entrepreneur it’s up to you to create a sustainable routine.

When you’re self-employed, you feel constant pressure to optimize how you spend your time.

After all, there is no “perfect” and things can always be improved.

And there are pitfalls everywhere…

Too much time spent learning or reading… and you get analysis paralysis.

Too much time focused on the wrong/reactive/non-important tasks…you end the day feeling like nothing is accomplished.

Too much time churning on work and you get… burnout.

Too much time saying yes to things and you get…booked up with minutia.

Here are some ideas that you might find useful as you plan out your time:


I'm a sprinter. I don’t think anything specific can hold my attention for more than a few months.

Working around this means that “what’s old is new” for me. Even if I’m continuing to blog (has it been 6-7 years already?) the phases change for me.

Each blog post is a mini-sprint in itself.

So I only really need the attention span for one blog post at a time. That I can do.

If you do something when it comes up, rather than “scheduling it” later you can seize the energy you have at the moment.  More on energy below.

[Check out my quarterly client process here]


I’ve totally changed my mind on vacations. Vacations, for the sprinter and entrepreneur, are what create upgrades to your business.

So what this means is it’s dedicated “Deep work” time on their companies. Even if you’re fully engaged in your vacation, relaxed… you might find ideas just pop into your head.

I think you could take 1-2 vacations every quarter and while some think this is slacking, founder types are obsessive and they will be thinking about their business anyways.

When you vacation, you are pulled out of the details of your business.

From this vantage point, you will more acutely understand what is not working.

Vacations are a critical component to structuring your year for better business growth.


I also structure my work with clients in 1-3 month periods of time. This creates a container for a beginning and an end.

The container creates momentum in particular areas of a business, for the quarter.

I think we’re naturally wired for the rhythm of seasons. I don’t think we’re meant to do the same exact thing over and over and over for years. We’re not robots, energy ebbs and flows.

So, learn what season you’re in, and then apply the right lesson of that season.

The Seasons Book


When I have energy for something, it’s easy. There are plenty of things that energize me and I’m always on the hunt for what that might be.

I’m in a meeting, and I’m feeling internally bored. What will excite me about this meeting?

What about the topic is interesting?

What is something daring I could try or do to feel energized?

When you think in terms of energy you see what you gravitate to and what you pull away from.

And you can create it for any task if you just find what, within it, is in fact interesting, curious or worth exploring.

The key is to develop preferences.

Developing preferences is the hallmark of the entrepreneur and artist.

This is “taste” and taste is energizing because it’s YOURS.

The whole reason you started a business or art project is because of wanting to share your ideas, not follow someone else’s.

When your preferences become diminished by your schedule, you’re losing the very thing you’re seeking most as a founder/creator.

Seeking what energizes you consciously... changes your week from structure to flow.

Everyone is recommending structure because what people think they are seeking is structure. But for many what we're looking for is to feel fully engaged in the flow of our work.

That feeling is how we know we're doing great work and what makes it worth it to work for yourself.

This week, use your preferences and energy to help guide what decisions you make and how you engage in your work.

Anything else I can do, hit me up. Have an awesome week