Briefing Notes: The Worthwhile Search for Meaningful Work

Published: January 12, 2020

“As with all matters of the heart, you will know it when you find it.” — Steve Jobs


What ‘meaningful work’ represents has evolved for me over the years, as the gray in my hair multiplied and tripled. My definition of success has changed as well.

Perhaps you feel the same way.

In this issue are a few thinkers of our time who have contemplated what meaningful work and success mean, and how we may find them.

I find myself re-reading these every year or so.

(1) One thing we often hear: “Do what you love.” But as Paul Graham, founder of Y Combinator, points out, “Doing what you love is complicated.” In this essay, he expands on how we can find and do what we love.

You shouldn’t worry about prestige. Prestige is the opinion of the rest of the world. […] This is easy advice to give. It’s hard to follow, especially when you’re young. Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.
It’s hard to find work you love; it must be, if so few do. So don’t underestimate this task. And don’t feel bad if you haven’t succeeded yet. In fact, if you admit to yourself that you’re discontented, you’re a step ahead of most people, who are still in denial.

(2) Many of the Steve Jobs’ quotes floating around come from his 2005 Stanford Commencement Address. Here are a couple of my favorites. But it’s worth it to read the entire text.

I didn’t see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me. The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.
Sometimes life hits you in the head with a brick. Don’t lose faith. I’m convinced that the only thing that kept me going was that I loved what I did. You’ve got to find what you love. […] Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it.


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Modern philosopher Alain De Botton examines our ideas of success and failure — and questions the assumptions underlying these two judgments in this TED Talk: A kinder, gentler philosophy of success. Is success always earned? Is failure?


“Usually when we say ‘it’s your turn’, we mean that it’s your turn to be picked, to be the next one, the person who fits in more than any other. […] This is the model in which you wait for change to happen to you. Another model of ‘your turn’ though, is the model of the person who makes the change. We seek the change that is interesting, the change for the better, and most of all, the change that connects us to someone else. This is the freedom to make change, and the willingness to seek out the tension it brings.” — Seth Godin 


The Success Principles*
by Jack Canfield
A question I ask podcast guests is the one book that’s made an impact on them. Canfield’s book The Success Principles is the most frequently mentioned. It’s a classic and was recently updated in celebration of its 10th anniversary.

*Affiliate Disclosure.


Doing meaningful work can lead to a desire to go off on your own, start your own business or to forego full-time employment in favor of a freelance career. Autumn Witt Boyd, an award-winning Intellectual Property lawyer, joined me on the podcast this week. We drilled down on basic blocking and tackling stuff you’d want to have covered as you’re starting out. This way, you can legally protect yourself and the investments you’re making in your new direction. Catch Episode 118 on your mobile device. Or read it here.

Registration for Start Your Side Business Mastermind is now open has ended. SYSB is a facilitated 10-week small-group experience. It aims to get you in position with a strategy for your side-business and get you going with a practical plan that suits your specific situation. If you’re looking to make 2020 the year to make solid progress on your side business, consider joining us for this winter cohort.


The previous decade ended up looking quite different for me than what I had imagined in 2010. Part of it was my own evolution as a person, my maturation 👩🏼‍🦳, and my response to the changes happening around me (tech advancements, etc.).

My changing perception around what success means, what I want my body of work to be about, and how I want to contribute all fed the detours and transitions I’ve made this past decade.

As I start this new decade, I find myself taking time to re-examine and wanting to be more deliberate about my next steps. I’m not getting younger (who is?!). And I’d like to be more intentional about the direction I take from hereon.

As de Botton says in his TED Talk:

“We should focus on our ideas and make sure that we own them, that we’re truly the authors of our own ambitions. Because it’s bad enough not getting what you want, but it’s even worse to have an idea of what it is you want and find out at the end of the journey that it isn’t, in fact, what you wanted all along.”


A former management consultant and IT leader, Lou Blaser is the editor of Briefing Notes and the host of the Second Breaks podcast. She is also the author of Break Free: The Courage to Reinvent Yourself and Your career. Lou’s work is focused on helping experienced professionals navigate an evolving work landscape so they can continue their impact and relevance in a changing world.

The world of work is changing.

Stay smart about it.

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