Monday inspiration: Pursuing things that actually matter

As I mentioned a few weeks back, I’ve been seeking ways to live a more meaningful, impactful life. This doesn’t mean I have to run away to the desert to wear sackcloth & ashes—at least my family hopes not!—but it does mean pushing myself harder, and with more discipline, to ask good questions & to act on the answers.

Before I took my sabbatical to Guatemala, I reached out to Jeffrey Veen, who had just sold Typekit to Adobe. Over lunch he explained that after he’d left his previous gig, he undertook what he called “100 lunches,” meeting up with as many smart, interesting, creative people as he could. In the process he gradually formed the idea & knowledge needed to launch Typekit. In a similar vein, I’ve been talking to many of the bright, thoughtful people I’ve been blessed with meeting over the years, learning more about their journeys & perspectives.

My friend Deepa spent 10 years in product management at Macromedia/Adobe in SF, then totally reworked her life: she joined Charity Water, moved to NYC, learned a ton, and recently joined the Clinton presidential campaign. She advised me to think in lean-startup terms, prototyping changes to my life, seeing what holds promise, and iterating to learn more.

Deepa also mentioned The Quarter-Life Breakthrough. I don’t yet know much about the book, but I did enjoy the TED talk below from Adam “Smiley” Poswolsky, in which he talks about giving up what you’re supposed to value to pursue what brings you real satisfaction. A few key points:

  • Find believers. They’ll help hold you accountable.
  • Stop comparing. It’s the thief of joy. (Okay, he didn’t use those words, but Teddy Roosevelt did, so that’s something.)
  • Make the ask.

Remembering that “The journey is the reward,”


2 thoughts on “Monday inspiration: Pursuing things that actually matter

  1. John – I’m a big fan of “What Color Is Your Parachute?” and recommend it; I’m not familiar with this latest book, but it sounds very interesting and I’m going to find it. The key advice I take and recommend from WCIYP is the workflow [sic]: figure out what you want to do, figure out where you want to live, figure out who does what you want to do there, find a way in and convince them you’re the right person. The hard part–the part I intuit you’re wrestling with–is “what do I want to do”. My only advice is figure out what makes you comfortable, fulfilled, and valued as you do it and as a result of doing it. The energy and time you invest in that/those endeavors must have a commensurate set of results, consequences, and benefits to you and the people in your life, including family, friends, and clients/patrons. If you can find that/those things to do AND provide adequate support for your family, I predict you’ll be a happier guy. This approach takes a strategic view, not limited to a tactical view of “what’s my next job”; it’s holistic. I did the work, I was/am happier, and my family, friends, and clients benefited. Now that I’m retired….well, I took the same approach with similar results. Outside of the things I can’t control, life is pretty good and I’m comfortable with me. Hope this helps, if only to support your desire(s) and approach. Good luck…and thanks for the reference material (it may be useful when I deal with college students who ask my advice about careers and life).

  2. I appreciate the kind words about my TED talk, John, thanks for sharing!

    Here is the definition I use for “meaningful work” in the The Quarter-Life Breakthrough (intended as more of a framework than a singular definition, because how can you truly define something like “meaning”?): Meaningful work provides personal meaning, reflecting who you are and what your interests are, allows you to share your gifts to help others, and is financially viable given your desired lifestyle.

    The bottom line is that everyone is different and what’s meaningful to someone else may not be meaningful to you. The challenge is to embrace the journey to discover what’s meaningful to you. Not easy, sure, but definitely worth it.

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