A map for indie living

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

• Who can you email? Old clients, bosses, colleagues? Send a note letting them know you’re looking for work.
• How can you let people know that you’re “in the market”?
• How can you assemble a portfolio or set of case studies?

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

• What is something you can do that’s public and within your control as narrative aircover?
• Take some time for self-care. Exercise, creativity, emotion. You may well be hurting in your job so go easy on yourself. Remind yourself what you love in life.
• Maybe start a practice of journaling or note taking as a way to examine your own identity and ego more directly?

Potential failure modes:

• Trying to craft a tight positioning for your work. You’ll fail because you don’t have any work yet, don’t know what you want to do or who you want to be. What you’re really chasing is a coherent identity. Chase narrative aircover right now instead.
• Trying to do client work AND build a startup or Big Project. Have patience. Remember that freelancing and consulting isn’t a treadmill, it’s a path to cash and calendar freedom. Equity and building comes later. Send an invoice first.
• Don’t over-complicate your business setup. I didn’t start an LLC till year 2 and I still make my invoices in Google Docs and track revenue in a spreadsheet. It’s OK to be afraid of this stuff, it’s not OK to be paralyzed by it. It’s new and uncomfortable, but it’s not hard. And it doesn’t have to be complicated.

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:

• Care about your work product. Share them with friends. Ask clients for feedback. Think about ways to level up and get more senior in your work. What does the level above you look like?
• Are there ways to reject “how this work is done” to focus on the bit that you think has the most value?
• Experiment with writing and “being visible” - whether blog posts or LinkedIn posts. You need to develop a voice and the only way to do that is through experimenting and hitting publish on things. Any things. Small things. Things with personality.
• How did your current clients find you? What commonality can you draw from this in terms of industry / job role / how they found you? How can you use that to find more people like them?
• Maybe think about starting a newsletter or a blog. But don’t overthink it. It’s not “The Ultimate Destination for Content Marketing Strategy” - it’s just “Tom’s blog” for now. Remove the pressure and don’t worry about a niche. Just publish. One foot in front of the other.

Below the surface:

• How are you spending your time? Which parts of client work light you up? What do you want to do more/less of?
• Notice which things you say that get the strongest reaction from clients. This is your early signal of where your voice is and where your opinions are interesting to the market.
• Find other people on the indie path (hi!) and chat with them. Build relationships, coffee meetings, friendships and communities. Start one if you can’t find one. This is essential psychological and identity work to make this path sustainable.

Potential failure modes:

• Trying to partner with others. You likely miss having colleagues and team mates. And you’re likely slightly insecure about the quality of your work. THAT’S OK. Me too. You don’t have to deal with that by building a goddam agency or finding partners. Join (or start) a slack group. Find a few peers to chat with and chat with them. Meet people for coffee meetings. Share your work products with close friends and advisors. Starting an agency ruins your ability to use consulting revenue as the cash and calendar freedom you need later on.
• Crafting a positioning statement. Seriously. Streaks > niches. Anytime you think you want to craft a tight positioning statement, instead of putting it on your homepage as “I do X for Y” instead write a 2,000 word blogpost about “How I do X for Y”. Don’t be so arrogant to asusme that you have tons of leads and need positioning to filter your leads. Instead it’s about demand generation - how do you get more people knowing about you. And whatever you do don’t write that essay in businessspeak. Let your punk and vibe ooze out of the pores. It’s about showing off how you think, not doing some generic SEO or content marketing bullshit.

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:

• Raise your seniority and raise your rates. Chase more senior work, more expensive work.
• Think deeply about the venn diagram of work you enjoy and work that the market wants. Especially where, as an independent you can deliver value differently from how an agency would approach it. Drive to client value.
• Create a consistent publishing habit. Twitter/LinkedIn/Email/Blog doesn’t matter too much but you’re really gonna regret not building this habit at this stage.
• Consider starting a community - now that you know a bit about yourself and the kind of work that you’re doing focus on either invest some serious time in another community or build your own. Networks matter.

Below the surface:

• You can’t sustain publishing without being interested in something. So deeply consider how to write and publish in a way that keeps you engaged. Don’t write “for SEO” or some BS. Figure out what you’re interested in and write about that. Write it in your real voice, not your business voice.
• You’re a real business now but that doesn’t mean you have to act like one. Find language to describe your work in a way that doesn’t make you want to vomit. Simple language. Focus on being senior and signaling that you’re expensive.
• You probably want an LLC and business apparatus at this point. Find a way to have “your corporate entity” send your invoices. Otherwise you’re going to vomit when you send a $50k invoice (or worse, get anxious and panic and never send the invoice). You need some psychological armor for the arena of capitalism.

Potential failure modes:

• Don’t try and operationalize your way out of the routine work. Don’t hire people, don’t outsource. Just elevate into the more senior strategy work. Charge more. Building a whole machine to do the execution work is just trapping yourself at this level and prevents you reaching level 4 & 5. Consider partnering with agencies or vendors to work on the execution but remain separate - don’t bring on responsibilities or overhead.
• Now that you’re earning good money you can get stuck just doing the same thing over and over again. Force yourself to keep learning, keep moving. There are always more senior levels to reach. Look for them, get access to them.
• Now that you’re generating leads for good money it’s easy to simply burnout from overwork. You’re forcing your rates higher and higher and it’s getting harder and harder to say no to work (“Can I turn down this $20k client gig to take a week off”). Don’t overwhelm yourself with hours worked - take breaks. Start an exercise routine (yours has probably evaporated in phases 1 and 2 I’m sorry to say). Remember: price every project so that you’re happy when they say yes.
• Not being visible enough. You can be increasing your fees, making good money but if you’re not being visible enough (find a mode, not a niche) then if a big client engagement ends you can enter a big deep dark hole where revenue tanks and you question everything. This can rock your confidence and send you into a tailspin. You have to build your fees and your visibility in lockstep. Dealflow dealflow dealflow.
• C’mon. You’re STILL gonna want to craft a tight positioning. Don’t do it. Just write. Streaks > niches. You’ll think you have the confidence to actually nail a positioning statement now - something that’s TRUE. But it’s a trap. You’ll end up getting stuck in this phase and never elevating out into phase 4 & 5. A tightly crafted positioning statement can actually prevent you from securing senior work and reaching the cash/calendar freedom stage.

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:

• Hopefully you’ve figured out some kind of distinctive opinion and perspective on your work by now. No! Don’t turn it into positioning - but do turn it into a vibe essay (or 5). Show your thinking, get into the details. You’re chasing senior clients and that requires exposing some vibes.
• If you examine your relationship between time/energy/money closely enough you should be able to start saying no to the kind of work you were doing in phase 2 and 3. This will feel scary and painful - don’t be afraid to move your threshold around a bit. Say no, then when cash gets tight start saying yes, then try saying no again a few months later. Iterate!
• Leverage your communities and networks to have some honest financial conversations with other senior indies. This will give you the confience to charge 10x what you were charging when you first started - that will feel terrifying so you’ll need some concrete examples, peers and support system to back you up.

Below the surface:

• Some deep existential questions might be setting in about now. Is this work really more interesting than taking that CMO role? Should I stick the course? Where does this path lead? Don’t worry about the answers to these questions - the most important thing is to keep learning. Keep pushing on things that interest you.
• You might get tempted to standardize work or package up your pricing into defined “packages”. Tread carefully here - it can be very easy to sink a lot of time and energy into something that only generates “phase 3” work. Is that what you really want to be spending your time on?
• If you’ve built a publishing practice, it might be feeling stale right now. You might think it’s feeling bland or generic. You might question whether it’s really worth doing. This is a sign that your taste is developing. Your taste is growing and you’re looking at your own work with a very senior, experienced lens. This is a good sign to push your writing into weirder, deeper territory. Talk about the way your industry really works, not how everyone else thinks it works. Developing opinion is continuous work that is never done.

Potential failure modes:

• A lot of the work is getting routine and easy here. You know how to generate clients. So what is there left? It’s easy to get bored and disconnected from the work. Find a way to keep yourself interested in the work itself. Write a book about the practice of the work. Read some academic papers about your field.
• Not building up a warchest. If you’re building up cashflow and simply spending it then you’re running a risk. By this time you’ve been self-employed for 5-7 years. The chances are only increasing that you’re going to need to take time off for a medical emergency (you or loved ones). Or take an actual holiday. Or buy a house. So don’t be stupid - cash looks like king but the world runs on credit/savings/retirement/health insurance etc. Start building wealth (mental, physical, economic).

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:

• Are you presenting yourself to the C-suite and senior stakeholders correctly?
• Are there opportunities to take equity in companies you’re working with or advising?
• You might have several different personas or brands at this point (like me: tomcritchlow.com and the SEO MBA).

Below the surface:

• What do you really want to spend your cash/calendar freedom on? Family? A startup? What kind of equity do you need to continue this for the next 15-20 years?
• You might get tempted to write a book / launch a conference or some other ego driven identity project. (I’m writing a book!). Remember to embed your real self in it.

Potential failure modes:

• Given your publishing and point of view you might feel comfortable adding new brands and deliberate products / consulting offerings. I think you have to be careful here. Early success isn’t necessarily the same thing as launching something you can sustain.
• If you’re spending a lot of your calendar freedom on something totally unrelated to your consulting work then you will feel disconnected from the work. I’m guessing the right answer is to deliberately dive into a specific area/topic and understand it more deeply than anyone else. What can you be a world class expert in? Be sure to include things you’re actually interested in here.
• Can you legitimately say no to phase 4 work? What does phase 5 work look like? Don’t know the answer to this.
• If you bite off a big creative / ego project like writing a book, be careful of stalling out. Investing a significant amount of time into something that doesn’t see the light of day can cripple your self confidence.

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.