Tom Waits' 2-step career master plan

Philip Morgan

I really love the 2-step career master plan outlined by Tom Waits in his song, Goin' Out West. Here's a partial excerpt from a song that's hard to pull a partial excerpt from because the whole thing is so amazing:

"They got some money out there
They're givin' it away
I'm gonna do what I want
And I'm gonna get paid
I'll do what I want
And I'm gonna get paid

Little brown sausages
Lying in the sand
I ain't no extra baby
I'm a leading man

Well, my parole officer
Will be proud of me
With my Olds 88
And the devil on a leash
My Olds 88
And the devil on a leash

I know karate, voodoo too
I'm gonna make myself available to you
I don't need no make up
I got real scars
I got hair on my chest
I look goooood without a shirt"

So here's Tom's 2-step career plan:

  1. Do what I want

  2. Get paid

This has pretty much been my career plan as well, and I think there's some significance to what Tom Waits is suggesting we do and the order in which he's suggesting it.

Doing what we want

It's no accident the doing comes before the getting paid.

In the domains of physical/software products, higher education, and expertise-driven business -- to name just three -- the idea that you would invest before you earn is completely obvious. People do pre-order stuff that doesn't exist yet (ex: Kickstarter), but the usual route to gettin' paid is to have something of value to get paid for.

When I think about how I got into self-employment, it was through a set of circumstances in which I didn't think I could afford to invest before gettin' paid. Back then, I needed to have something I could sell now in order to get paid very very soon.

This led to thinking that was oriented around very short time horizons. Weeks and months, not years or decades. Yet, when you're thinking in terms of building up career assets and valuable expertise, you must think in terms of years/decades in order to really thrive. 1 At the same time, your mortgage lender needs you to be thinking in whatever terms will keep the mortgage payments to them happening on time.

This early career short-time-horizon-thinking "wore a groove" into my brain, one that I'm working to consistently get out of. Having a long-term vision oriented around rare, valuable expertise is, I believe, the best way to build a very profitable and durable services business.

It's also no accident that what you're doin' before you get paid is something you want.

When specializing, there are three basic approaches to making the decision about how exactly to specialize:

  1. Find a head start -- an advantage of some sort that you have -- and focus ruthlessly on that head start.

  2. Find something you love -- a group of businesses or people or problem you love solving -- and serve that group of people in an extravagantly valuable way.

  3. Pursue an entrepreneurial thesis -- an idea you have about creating value by responding to what's changed or what's stayed the same in a market.

If you can specialize in a way that combines #1 and #2 above, you will be unstoppable. If you pursue approach #3, then it really really helps if you are a disciplined mercenary or you can combine approaches #3 and #2.

These combinations are helpful because the love sustains your effort over the long term, and without the beating heart of love for what you're doing, your business is less able to ride out the difficulties that lie between where you are now and your vision for future expertise. 2

To summarize: do what you want. Invest first. Pick something you care about to invest in.

Gettin' paid

For Tom Waits' 2-step career plan to work, you have to be successful on both steps. This brings up the gettin' paid part.

This is where ideals get constrained by economic realities. Not every thing you or I might want to do is gonna' get us paid. Or at least not in money.

Want to become an expert in medieval folk poetry? Go for it! You will likely get paid in emotional and intellectual terms far more than you'll get paid dollars or your local currency. Maybe this will constrain your decision about where to invest in expertise. Or maybe it won't. Just don't be confused about the actual economic value of your expertise in medieval folk poetry. For the most part, you don't get to decide what the economic value is. Others do, and that can feel unfair. If money is somewhat or very important to you, get over that feeling of unfairness. It won't help.

While there are constraints, it is also possible to invent an entrepreneurial job for yourself and find ways to get paid. This is not easy at all. But it is possible, and it's fascinating to see folks pull this off.

I like the Corey Quinn example:

I've interviewed Corey and I can assure you, his journey to where he is today didn't start with a job ad on that perfectly set him up to become an AWS cost optimization consultant. He totally invented his job for himself, did the work necessary to create awareness and desire for his services, and continues to learn from the market and refine what he does in response.

If you want to get paid without figuring much at all out or inventing anything new, open a laundry dry cleaning business. There's a really go od roadmap for that kind of business, and you can succeed without the risk of having to figure much at all out.

But if you're up for a different sort of challenge, you might enjoy exploring the interplay between doin' what you want and gettin' paid. That's really fertile entrepreneurial ground.

In this fertile ground, the market has a voice, and you also have the power to alter the vocabulary3 the market uses to voice its desires and needs. If you're not up for the work and patience required to alter the market's vocabulary, you can at least listen intently to what it's saying and alter what you offer in order to maximize the value you create for the market.

To summarize: every market has a spectrum running from "we already understand this, we already value this, and we regularly need this, so we represent a river of money you can drop your fishin' line into" to "we don't understand this at all, but if we did a few of us might occasionally pay a lot for this". We might think of the first as the easiest place to set up business. And we'd be right, but things that are well-understood, commonly valued, and regularly bought are also things that are prime for commoditization. This is one of the paradoxes of value creation. The easiest place to get started is also the easiest place to get ended by commoditization.

So as we're doin' what we want and seeking to get paid, we might need to look a little further down the road, beyond that's easy to get paid for today.

That's our entrepreneurial challenge, isnt' it?



  1. Or, you can get lucky. There's always that.
    I try to avoid listening to folks who are "reading you their winning lottery ticket number".

  2. This idea of loving what you do can easily slide down an unhealthy, slippery slope into workaholism or having an unbalanced life. That's not what I'm advocating for, though I might advocate for having work that is so compelling and interesting to you that you constantly dance on the thin line between full engagement with your work and something beyond that point. Or seen differently, your work often feels like enjoyable play, and so you treat it like play.

  3. I'm using this idea of the voice or vocabulary of the market as an analogy. It's an apt one, though, because of how the way we speak effects the way we think. new words enter the vocabulary and create new possibilities, new needs, and new desires.