3 Takeaways from Jenny Blake

In this month’s Deep Dive series, we sat down with author and podcaster Jenny Blake. We discussed her most recent book, Free Time, and the fundamental principles underlining the book– namely the idea of giving yourself permission to create systems that help you work smarter and… less.

Here are my three biggest takeaways from our conversation.

1. Business as Personal Development Platform

So much of our discussion about work these days has to do with balance: Work/Life balance.

But the truth of how we actually live is more integrated. We can’t just put up a front about who we are at work and make it someone different than who we are in our personal lives.

The idea of this first takeaway is thinking about behaving at work and as a business owner as a platform for living better in the rest of our lives.

That includes: setting and keeping boundaries, taking care of your own needs before the needs of others, building a practice of focus and self-awareness, working on your courage to have more confrontational and challenging-but-needed conversations.


When I talk about my relationship with my Caveday Co-Founders, I often mention how I feel like our partnership makes me a better person. We question processes to be more efficient in our meetings and how we run the business. But we also make room for inefficiencies– personal time, emotions, clearing the emotional air when need be.

Running a business (or even having coworkers) can be a means of working on yourself. Your work environment can be part of your personal development journey.

2. “Eyes on your own paper”

We all come into our relationship to work with deep-seated beliefs about how work should be done, where it should be executed, and how.

So when our colleagues, roommates, partners, and teammates don’t follow those expectations, it’s easy for us to get judgy.

But the truth is, we don’t know where they are in their process. We don’t know what will be helpful in their work. Who are we to tell them how to do their work.

Like Jenny said– that energy could be refocused on our own work to create more and potentially earn more.

Work doesn’t always get done at a desk.
Work doesn’t always get done from 9-5.
Work doesn’t always require a computer.

Eyes on your own paper, please.

3. Do less work.

When Jenny first said that, I had to stop her.

“Really? THAT’S the goal?”

It was just so hard for me to get behind. Being raised in an achievement-driven world and working in a capitalist environment, I’m so used to being force-fed messages of “get more done.”

But what Jenny is talking about here is so in line with the Caveday philosophy. It’s not exactly ‘do less work’ as much as it is ‘work less, but smarter.’ More hours rarely equates to better or even more work.

So with better focus, with better intentionality, with a system I’ve built to automate minutiae and a team to delegate work to, I’m more able to focus on the important stuff and just do less work.

Less work can often mean more impact.
Less work can often mean more value.
Less work can often mean more rest and more energy.

It’s counter-intuitive, but Jenny’s point is well-taken.

Check out her book, chock-full of amazing tools, ideas, and systems to build from: itsfreetime.com


Caveday is a company aimed at improving your relationship to work. We write regular posts here and send out monthly newsletters with productivity tips, life hacks, and recommendations. Sign up for the mailing list here.

Jenny Blake is an author an entrepreneur. Her latest book is Free Time: Lose the busywork, love your business. Learn more here.

Jake Kahana is a cofounder of Caveday. Sign up for his personal emails, called “The Email Refrigerator” here.