I try not to use my phone too early in the day, but this morning while I was peeing, I opened the latest email from Ted Gioia. I almost didn’t click it. The subject line was: “I’d Do These Seven Things, If I Were Starting Out in Music Today” and my amateur but enthusiastic guitar skills probably don’t count. Lucky for me, I clicked it anyway.
Passion without a plan
In his piece, Gioia argues that creative people - musicians, artists, writers, et al - often approach their craft with passion but not a plan, even when they’re rigorous in other areas of their life. Gioia is a jazz musician and former management consultant who produces on a prolific, comprehensive writing schedule - his Substack, and 12 books besides.
He writes about how his meticulous, structured approach to work (planning, systems, and networking) didn’t apply to his music - and not due to a lack of love, effort, or time.
Despite a music career being his “highest aspiration” and pouring hours of practice and dedication into playing music, he didn’t do critical things that would have made a jazz career truly possible - building a network, getting a degree, reading textbooks, hustling for gigs, or learning about music technology and the recording process.
What made this strange is that I was pragmatic and thorough in every other facet of my life. I doggedly pursued other goals—studying various subjects and passing tests, developing job skills, learning from great teachers, getting degrees and credentials.
In all those other areas, I applied intense discipline, and worked hard to identify (and fill) gaps in my knowledge.
But in the activity I loved most, namely playing music, I did everything spontaneously, without much forethought. I was guided entirely by the passion and excitement of the jazz experience.
- Ted Gioia
I’m no jazz musician, but this hit home for me on a few levels. In particular, in my writing career, which I’m still treating as a side hustle.
I’ve played this game before
I’ve been self-employed as a consultant, speaker and trainer for over 11 years now, and none of it happened by accident.
I planned, strategised, and networked. After I left my job in 2014, I:
Networked and built relationships
- Reached out to hundreds of potential clients and drank hundreds of coffees.
- Hassled business case consultants across New Zealand until one of them agreed to mentor me and include me on projects.
- Travelled to Australia every three months to plan and strategise the upcoming quarter with a group of my peers.
Studied and learned
- Studied to become a Better Business Cases practitioner.
- Flew to Melbourne to become a certified Investment Logic Mapping/ Investment Management Standard practitioner - and renewed my certification annually.
- Researched countless hours and wrote three books and hundreds of articles for my own platform and other magazines and audiences.
- Took courses in public speaking, stand-up comedy, writing, facilitation, strategic planning and coaching.
- Learned to film videos, publish podcasts, build websites, and create business systems.
Promoted
- Published a weekly newsletter for the last eight years.
- Built an online audience through relentless outreach, publishing, filming and content creation.
Hustled
- Participated in tenders, proposals and panels.
- Ran free and paid webinars, lunch and learns and speaking events online and on both sides of the ditch.
- ‘Laddered up’ from free gigs to low-paid gigs to high- leverage delivery.
- Launched dozens of offers and programmes, over half of which failed miserably.
Invested
- Joined a professional association of speakers, authors and trainers and invested $25,000 to learn how to commercialise my IP into programmes and outputs.
- Paid professional designers, editors, assistants, and PR people to establish my brand, create compelling materials and place me on podcasts, radio shows, TV shows and newspapers.
I didn’t expect any of it to happen by accident, and I never thought being talented would be enough. I also did it with three young kids and that’s why I’m so tired now.
But I’m not doing it as a writer
I’ve done some of these things with my writing career, sure. I’ve taken classes, applied for a couple of things, and continued to publish essays and experiments. I’ve read a lot of craft books. I’ve done a lot of writing. It’s not a lack of time, effort, or love. But there’s no way I’ve been as dogged and methodical with this dream, as I have been with my business.
After reading Gioia’s article, I couldn’t stop thinking about it all day. What would happen if I, and so many of the wishful thinkers I know, took ourselves seriously?
I filmed this little rant on LinkedIn. I kept making lists and scribbling things down. And now, I’m firing this stream of consciousness straight into your brain hole.
I’m a strategist, by trade. I’m organised, and I know how to join the dots between a big dream and daily choices. I’ve taught thousands of executives, politicians, and bureaucrats across the world how to do this. I’ve led transformational thinking for organisations, sectors, and communities. In short: I know how to do this.
So if a Capital W Writing Career, - getting out of the delivery grind and onto writing about Big Ideas - is my “highest aspiration” à la Gioia’s jazz career - where’s the proof? If I really want this, I’ll apply my skills and persistence to it in exactly the same way. I’ll make a full-time job out of drafting, publishing, pitching, networking, investing in my development, honing my craft, and promoting my work. I’ll create a plan, make a spreadsheet, and track my progress every day, week, month, and year.
Because the stuff we care about doesn’t happen by accident. In fact, the stuff we care about requires us to plan and work twice as hard as the other stuff, to compensate for the self-sabotage and Resistance that comes with it.
It’s time to get your shit together
I know hustle isn’t in fashion anymore. We’ve (rightly) seen a backlash to dude-bro productivity advice, burnout-inducing optimisation culture, life hacks and girl boss bullshit. I’ve led some of that charge!
But I think we’ve overcorrected. I’ve been thinking this while I’ve been writing The Ambition Recession series, and I really started thinking it once I finished last week’s essay about the ambition vacuum.
Because there’s plenty of people still out there rise and grinding - the tech bros, the tradwives, the conservative right, and the startups, to name a few - while young people, the left, creatives, and big-idea progressives are wringing their hands about the state of things.
The vacuum we leave by not stepping up is being filled - and, at the risk of pulling a Kim K level of blind ignorance here, if we’re not prepared to do the work… well, this is what we get.
There are too many people broke, burnt out and disillusioned right now. I get it, man. I’ve been there. I’ve lost months to depressive fugs. Years to poverty and discrimination. But I also dragged my pregnant ass out of the foster-care gutter at 17 to start a cleaning business that paid my rent and talk my way into university without the entrance qualifications. Because at some point, you have to decide whether you’re going to pick up your shit and own your life and future.
Here is your tough love
The most successful entrepreneurs, creatives, athletes and politicians are not useful role models. They tend to have some combination of inherited wealth, family connections, genetic superiority or blind luck. Don’t listen to them. You don’t need to be Bill Gates, but I’m pretty confident you could be making enough money and extracting enough meaning from stuff you care about to live your values and your dream life.
It won’t happen if we keep dabbling, waiting for inspiration, waiting to get noticed, picked, seen, found. It won’t happen if we treat our ambitions, lives, and creative work like weekend hobbies. It won’t happen until we take ourselves seriously.
This message is particularly for you if you are*:
- On the left, living your best woke life, sensitive to structural forces that make the whole thing feel futile
- Battling or recovering from a ‘down’ month/ year/ era (restructure, mental health, relationship garbage, et al)
- Kinda broke or at least feeling like it especially when you go to the supermarket.
- Relatively young yet already disillusioned with the world.
I want you to hustle like you mean it
Here’s the message: It’s time to hustle. It’s time to #riseandgrind. Write a plan. Look 3-6 months ahead. Prepare your week on a Sunday night. Schedule in the things you say matter. Strategise your way into the room you want to be in.
Put the waah-machine down, pick the war machine up, and get moving on your best life before you squander the whole thing whinging and waiting.
And you know what? Engage in all that tacky, shitty, optimisation culture with checklists and protocols and tactics, because one or two of them will work for you.
Absorb semi-motivational speeches about mindset and life-hacks.
Listen to Jocko Willink or James Clear or pick one of those privileged out-of-touch dude-bros who doesn’t have to juggle the slow cooker, the after-school activities, the caring responsibilities, the home maintenance and the health issues and just… pretend you’re one of them for a minute.
Let them remind you about the usefulness of personal discipline and habits because they’re wrong about a lot of things, but not about that.
Go to bed earlier. Exercise every day whether you want to or not.
Do this:
- Write down 5 habits or practices that will make your dream real.
- Put those as tasks in your calendar.
- Start a spreadsheet to track your activity.
- Fill it in every Friday.
- Repeat.
The world is unfair whether you try hard or not
Yes, the world is unfair. Yes, your life is going to be significantly easier if you are a white, straight, middle-aged man with inherited wealth and a partner who takes care of your home and family for you. Yes, politics is fucked and AI is problematic and everybody else has it easier than you and you’re too old or too young and too dumb or too smart and too poor and it’s too cold.
So what? That’s true, either way. That’s your starting point. Your Ground Zero. It’s up to you what you do from here.
There are organised networks of entrepreneurs and activists out there with well-funded think tanks, thriving media ecosystems, cold plunges and influential relationships who are flooding your Nanna with disinformation on Facebook, enabling the resurgence of measles and stoking culture wars to distract from real wars.
These people are planning years ahead, building infrastructure, and bending society and technology to their will. They are concentrating wealth and embedding privilege.
And you could learn a thing or two from them, quite frankly.
It’s time to take yourself seriously. Professionalise your ambition. Treat your life as a vocation. Fight the war. Fuck the norm.
Til next week,
A
*If you’re already a right-wing-voting, start-up-founding, cold-pool-plunging kinda guy or gal, you can just skip this one. I still love you and think you’re doing great, but your prescription is different. Read a novel. Have a bath. Clean out your pantry. Ask a woman 5 questions in a row. Listen to her answers without providing an anecdote or lessons of your own.
