Penelope Trunk Makes Me Think Hard About What I’m Doing and Why

Brazen Careerist’s Penelope Trunk

I’ve been reading Penelope Trunk’s mindfuck of a blog, and learning a few things in the process.  Listening to this podcast, in which Penelope gives brutally blunt career advice to hapless blogger Steve, was sort of a wake-up call.  Penelope asks Steve some hard questions about why he is blogging, and what his goals for his blog are.  When he’s evasive, she rips him a new one.  It’s not pretty, but it’s honest, and to Steve’s credit he posts the whole thing unedited.

Penelope can be thought of as kind of an anti-Tim Ferriss.  Where Tim looks for simplicity and optimization, Penelope looks for conflict and doubt.  Tim polishes his image and generally presents his best side, while Penelope shares her angst, personal failings, and relationship problems.  Tim offers advice about how to minimize work and maximize play, while Penelope takes as a given that adults need to put in 8 hours of daily work, and focuses on the question of “Whose working life do you want?”

So, who do I want to take advice from?  A borderline-narcissistic tango-spin record holder, or a neurotic Jew with Asperger’s syndrome?  Well, both actually, but I’ll focus on Penelope’s advice in this post since I talked about Tim Ferriss last week.

Why Do I Blog?

The last time I wrote about this question, I didn’t have a good answer.  I started this blog because I felt compelled to do so, and I continued it because it felt good to have an outlet for my thoughts on various topics.

Those things are still true, but after blogging for close to two years, it’s time to get real about what I’m doing.  What’s my goal for this blog?

Unlike Steve, I don’t have any illusions about making a living from blogging.  There are easier ways to make money.  My personal favorite is to collect royalties checks, and I intend to keep living my life in a way that maximizes royalty income.  The other way I make money is from freelance database consulting, which is a pretty good gig.  I like my clients and my colleagues, and I often enjoy the work.

To get real about why I blog, I needed to drill down to my life purpose.  I’ve stated before that I have an explicit life purpose, but I’ve been coy about revealing exactly what it is.  After reading Penelope’s blog, I don’t see any reason not to just put it out there.  The worst I can risk is embarrassment, and the upside is increased honesty with myself and with my readers.

So here goes.  My life purpose is to live well and help others live well (to live a loving, joyful, healthful, useful, and abundant life); to create and publish great electronic music; and to create and publish great blog posts, essays, and novels.

It’s embarrassing to put that out there for a couple reasons.  It sounds grandiose to say you want to make and publish “great” art and prose.  But whatever, that’s what I want to do.  I haven’t done it yet in any area, but that’s what I aspire to.  Realistically, I think I’ve co-written some good music with Spesh and Mark, published some really good music (other artists on Loöq Records, Kleidosty and Alan Live spring to mind), written a few interesting blog posts (some in essay format), and written two “learning how to write a novel” novels (as yet unpublishable).  Still, at 42, I have high creative and cultural aspirations and not much to show for it.  That stings a bit, but not enough to make me give up.  Enough to change some things about my life?  Yes, absolutely.  Do I know what to change exactly, or how to do it?  I probably know exactly what I need to do on a subconscious level, but I’m not there yet on a conscious level.  I’ll continue to share my process with you.

In terms of living well, life is good.  I love my wife and daughter, I love my friends and extended family, I love our house and our neighborhood (Temescal in Oakland — it’s full of intelligent liberal people and great restaurants I can walk to), I have money in the bank, aged Gruyere in my refrigerator, I’m in good health, and my database work pays most of the bills and helps me to feel useful to people and organizations doing good work in the world.

So where does this blog fit in?  Is it just a time suck, and a distraction from my life purpose?

Listening to that eviscerating interview with Penelope made me think long and hard about that question, but in the end the answer was pretty clear.  I want to help others live well, and I have something to offer in that area.

This blog isn’t an outlet.  It’s a frikking manifesto.  My writing style is conciliatory, even mild, but my views are not.  I believe a third of the USDA food pyramid should be thrown out.  I’m an atheist who prays.  I went a month without electric lights.  I believe most personal preferences are illusory and manufactured by the advertising industry.  I believe in radical forgiveness.  I think The Singularity already happened.

I’m deeply interested in how human beings can live better lives, both individually and collectively, both now and 1000 years from now.  It’s taken me almost two years to figure out what this blog is about.  It’s about exploring systems for living well.  I’ve added a subtitle to the blog, which sounds a little stodgy but at least gives new readers some idea of what I’m trying to do here.

In terms of specific life goals, I’ll probably continue to keep my cards close to my chest.  Here’s the reason why.

In terms of how this blog will change, I’m going to keep writing about the topics I’ve been writing about, but with the following changes:

1. I’m going to be more honest about questions I’m struggling with, doubts I have in my own life, and problems I’m having.
2. I may include fewer pictures and references links; both are very time-consuming — I’ll use the time saved to write more and post more frequently.
3. As opposed to just being a general idea outlet, the blog now has an explicit purpose (exploring and sharing systems for living well), so future content will better reflect that.

Whose Life Do I Want?

The other question that Penelope kept hammering in her interview with Steve was “Whose life do you want?”  When Steve mentioned a popular travel blogger, Penelope called him out.  “You can’t have his life,” she said, “you have a wife and kids.”  So Steve is still trying to figure out whose life he wants (and can realistically have).

Whose life do I want?  I figured out years ago I didn’t want the life of a superstar DJ (or even moderately successful touring DJ) … I was given a chance to embrace that lifestyle and I didn’t pursue it.  I have also lived the life of a very successful event promoter, and while aspects of that lifestyle were appealing, it ultimately wasn’t a good personality fit.

Still, I love both writing and publishing music.  Of all the figures in the music industry, Steve Beckett is one of the most impressive to me (the podcast is worth checking out).  Beckett co-founded Warp Records (who put out LFO, The Orb, Aphex Twin — Warp basically invented the electronica genre).  I don’t know enough about Beckett’s personal life to know if I want his life exactly, but I can identify with his approach (going for music that he loves personally, treating artists well and paying what is owed to them, refusing to stick to one genre).  While Loöq Records isn’t nearly as successful as I would like it to be (I’ll deconstruct what’s going on there in my next post “Am I Running a Fake Business?”), I know that I want the lifestyle of a successful independent label runner.  It appeals to me, and I have what it takes (attention to detail, strong ethical sense, belief in my own taste, desire to explore and support novel cultural spaces, and a great business partner).

In terms of novelists, there are dozens of authors whose lives I would like to emulate.  David Mitchell, Haruki Murakami, and Neal Stephenson spring to mind.  Of course, all three of these guys are super-geniuses (while I’m not), and they are only novelists (none of them is also trying to run a music label and do freelance database consulting at the same time).  So maybe a more realistic role model would be Olaf Olafsson.  He has a demanding day job, yet still finds time to be a novelist, and a good one at that.

Am I too old to be shooting this high, in multiple fields?  I don’t feel old, and there are plenty of examples of writers who find success in their forties, fifties, and sixties.  And the downside risks are pretty low.  Would I be happier giving up on my creative goals and just getting a job?  No way.  My life as it is now, even without dramatic artistic or entrepreneurial success, is pretty damn good.

Still, it’s possible that I’m trying to do too much, and thus doing nothing very well.  I’ll be exploring that topic in the next few posts.

So what about you?  Is your plan to be “independently wealthy,” which as Penelope says is “like a 5th grader’s plan”?  Do you know what you want to be doing and how you’re going to get there?  Or are you already doing exactly what what you want to do with your days?