Guilt, Happiness and Work - JRWI Weekly

Ideas on balancing entrepreneurial drive with wellness, bringing to life new ideas while living well ourselves and making space for what matters in a well balanced life.


I’m wrapping-up my third week post-rebirth. The new work I’m doing feels inspiring. I enjoy it too.

For the past three weeks I’ve spent my work time doing work I enjoy. This is a big change for me. It’s the first time my career has ever felt like this.

There were periods when it started to feel this way. Yet those were times when I felt doing work I enjoyed came at the expense of generating income. As a result, doing work I enjoyed came with a renewed sense of guilt.

These past three weeks have felt enjoyable. I’m doing work I enjoy and generating income doing it.

At the same time, I don’t feel guilt-free. I have to remind myself that doing work I enjoy and feeling happy doing it is OK. I’m doing this more and more often. The sense of guilt is diminishing as a result.

This guilt feels familiar. I was raised to believe work had to make us miserable. There must have been something wrong when it didn’t.

Just Rolling with It’s teaching me it’s OK to be happy, in life AND in work. I feel grateful for this.

How about you? Do you deserve to be happy in your work? Or does doing work you enjoy make you feel guilty?

Let me know by replying directly to this email. I read and respond to every reply.


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Look closely. Those rocks are balanced by hand, no fasteners. Fascinating!

Look closely. Those rocks are balanced by hand, no fasteners. Fascinating!

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Current Reading List

Technological Revolutions and Financial Capital

‘Before I read this book I thought that the history of technology was – to borrow Churchill’s phrase – merely “one damned thing after another”. Not so. Carlota Perez shows us that historically technological revolutions arrive with remarkable regularity,

Debt: The First 5,000 Years by David Graeber

Debt has 7,730 ratings and 1,029 reviews.

Music of the Week

Session Afro Love by SNOW BKLYN/NYC | Free Listening on SoundCloud

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Podcast of the Week

Meetings Are Toxic

Rework is a podcast by the makers of Basecamp about a better way to work and run your business. While the prevailing narrative around successful entrepreneurship tells you to scale fast and raise money, we think there’s a better way. We’ll take you behind the scenes at Basecamp with co-founders Jason Fried and David Heinemeier Hansson and bring you stories from business owners who have embraced bootstrapping, staying small, and growing slow.