June 3, 2022

A map for indie living

Phase by phase, one foot in front of the other

I’ve got a few friends on the cusp of independent life, either just about to leap into the unknown or already quit and they’re trying to figure it out.

So here’s a half-baked thesis and possible blueprint for navigating indie life.

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First, some core assumptions and insights:

1. Consulting can build cash freedom

People get an allergic reaction to the label “consulting” 1 but I’d like to argue that trading time for money is a great economic tool. It provides you cash leverage to pursue all kinds of other things.

For that reason, and because it’s what I know, consulting and client work features heavily here. You do you. But bear in mind that “client work” / freelancing / consulting comes in many different guises.

In particular, as you get more senior there are ways to do consulting work that don’t ruin your headspace. I wrote about that in my piece Sparring & Tenure for Indie Consultants. Not all kinds of work have the same headspace, stress and time commitment.

It can be a real failure mode to try and “start a startup” and “do some consulting” at the same time. Trying to balance these two competing types of work is extremely stressful and difficult.

Instead, view consulting work (i.e. freelance work) as a way to stabilize cash flow, build a cash war-chest and leverage into higher order forms of consulting that are high $$ while low headspace (like sparring). Getting to a point where you can do client projects with high revenue and clear time boxed availability is the necessary freedom you need to be able to also build a startup / write a book / build a project that might have real equity.

Consulting builds no equity, but it builds cash and calendar freedom to be able to build something that has equity without having to take on debt.

2. Positioning is for the ego, not for the market

I’ve got a full post in draft about this, but in short - it’s more important to find a way to be visible, with a distinct vibe, rather than craft a tight positioning (“I am an X for Y” or “I do XYZ for companies like ABC”). You think positioning is important but it’s just for your own sense of self-narrative and identity. Which by the way is important!

Paul Millerd captured this as don’t find a niche, find a mode and Venkatesh articulated as find a streak not a niche.

So, you have to find a mode, or a streak. It’s easier and more valuable than crafting a tight positioning.

But - your identity and self-narrative is important! So you should also craft some narrative aircover. This is some kind of project, website, initiative that you can lean on during the early days of figuring out indie life. Before you have a stable, real sense of how you’re making money or even WTF you’re doing you want some narrative aircover. There’s three key ingredients to narrative aircover:

  1. It must be completely within your control. This isn’t about success, it’s just about effort. Not “I’m selling tons of art” but “I’m making an art website platform”.
  2. Preferably non revenue generating. So people can’t measure it’s success (or failure) easily.
  3. It has to be interesting. Art, books, culture, community, non-profit. Make it something that makes you more interesting, open doors and starts conversations.

Then, while you’re trying to figure out whether you’re an “independent consultant” or “just unemployed” you can talk to people about what you’re up to: “I’m building an art platform, and looking for consulting work”

3. Change is continuous and self-directed, so you should stomach “bad work” because you can escape it faster

In full time employment change happens slowly in discrete jumps. You get a promotion or a new job. But being indie is a continual process of evolution. A never ending process of becoming.

When I started out, I had dreams of doing “innovation work” but quickly landed SEO audit work instead and (mostly) hated myself. Until I realized that cashing in invoices was simply the way to start the engine. Within 9 months I was already leaving that work behind and evolving my offering, the seniority of my clients and more.

So do whatever it takes to cash those first few invoices. That work doesn’t define you, you can iterate your identity and confidence with every single client. Fire up the engine and power out of it into better / more interesting / more expensive work. It’ll happen faster than you think.

4. How much “time” you have is really about how much energy you have

Your first instinct is to think about capacity - to try and ask “how much work can I do at one time?” but this is the wrong way to think about it for two clear reasons:

  1. Clients come in bursts - so when good work comes along you need to say yes to it and ride the peaks (there are ways to do that without burning out: more in this post The Jigsaw of Independence)
  2. Your headspace is a function of your energy and the kind of work done, not a function of minutes and hours.

Time, energy and money are three forces in constant tension. But energy is a stronger force than you think. Now that you’re out on your own you need to build your own mix of projects, only some of which will be revenue generating. Feed your soul with the right balance and you’ll be able to achieve so much more than narrowing your work too tightly. Importantly - don’t judge your projects by “how cool they sound” or “how creative they seem” - focus specifically on what the work looks like day to day. Nourish yourself and cash and calendar freedom will follow.

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Ok, so with those assumptions out the way, here’s a map. It’s not THE map, it’s mostly MY map. But it’s A map. And there aren’t enough of those for indie careers so let’s sketch this out together.

There’s phases.

If I had to guess each phase is 9-18 months? But I bet that varies greatly.

Phase 1: Making the leap, zero to one

This phase typically starts just before you actually quit your job. Starting to think about going independent, trying to line up work for when you quit. This phase is defined by doing whatever it takes to send your first invoice without shattering your self-confidence and identity.

Above the surface: Do whatever it takes to get your first invoice paid

Below the surface: Do whatever it takes to hold yourself together

Potential failure modes:

In phase 1 you steer by number of invoices sent. One invoice after the next. Set some simple financial goals and smash them. The work doesn’t define you. You’re just getting the cash flowing as a precursor to everything else.

Phase 2: Getting started

This phase is the real beginnings of freelance/independent living. You’ve got a few clients, done a little work, sent some invoices. Now you start to question whether this client work is any fun. Are you being useful? Doing good work? This phase is defined by deliberate learning and experimentation.

Above the surface:

Below the surface:

Potential failure modes:

In phase 2 you steer by finding a way to publish and be visible. Nothing heroic, just developing the consistent habit of writing. Streaks and modes not niches.

Phase 3: Find stability

This phase is where we start to really find our groove. If you’re doing it well this is where you step on the gas in terms of revenue and figure out how to consistently find good clients.

Above the surface:

Below the surface:

Potential failure modes:

In phase 3 you steer by number of good clients. Can you predictably generate clients doing senior (and expensive) work that you actually find interesting? Note that if you’re retaining them for a long time you don’t necessarily need that many of them. But you need to have some confidence that there’s another one just around the corner.

Phase 4: Find freedom

Here’s where it starts to get fun. This is where that sparring idea comes in. You’re starting to be able to do expensive work without committing a huge amount of time. This is the idea of tenure that I talked about at the beginning. You’re approaching tenure and want to keep pushing to find client work that is BOTH well paid AND leaves you some headspace.

Above the surface:

Below the surface:

Potential failure modes:

In phase 4 you steer by how much of your time is your own. Sure, you’re charging $20k / month but it’s only for 2 days a week. The other days are actually your own (vs the kind of work in phase 2 & 3 where you’re “only working two days a week” but in reality you’re getting pinged all the time all day long). Notice these stretches and start to project them. If you can do that and sustain it you’ve built cash and calendar freedom.

Phase 5: Build equity

I’d love to tell you how this story ends but I’m at the edge of my own map. I’m about to sail into the unknown. Maybe the earth is flat and I’ll fall off the edge. I have only a hazy understanding of what phase 5 looks like or where it ends. Is there a phase 6? What are the failure modes for phase 5? I’m not completely sure. I’d consider myself somewhere right between phases 4 and 5 today. Here’s some ideas:

Above the surface:

Below the surface:

Potential failure modes:

I think you steer in phase 5 by building sustainable wealth. Beyond cashflow, is your total wealth (physical, mental, family, economic) growing over time? Maybe in this phase you need to actually measure those things directly….

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As I said up top - this isn’t THE map. It’s probably not even MY OWN - I probably fictionalized and mis-remembered my own experience. But I hope it’s useful. Remember that change is a continuous process - and you have to look after yourself, because there’s no safety net.

  1. Rightly so perhaps if you read the headlines about folks like McKinsey… 


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This post was written by Tom Critchlow - blogger and independent consultant. Subscribe to join my occassional newsletter: