This article maps out the nine stages of a web designer, from the “friend of a friend” who builds websites for free to an owner whose agency runs without them. By the end, you should be able to point at the exact stage you’re in today, know what usually breaks at that stage, and see what it takes to reach the next one.

I spend a fair amount of time in a community called the Admin Bar. It’s full of agency owners, freelancers, hosts, and plugin developers. There’s a ton of combined WordPress experience, and some of the sharpest web people I know. We’re all doing versions of the same work, just at wildly different stages of the same career. A few members are booking their first paid projects. Many run busy shops where every decision eventually routes through them. A handful have agencies that keep running while they’re on vacation.

A few weeks ago I was at an agency M&A event in downtown Chicago at the Langham Hotel, and the contrast between the two groups became much clearer to me. The smallest agencies represented there were doing $2-3 million a year, with some in the 8 figures. What stuck with me wasn’t the money, though. Many of them were C-level and focused on the highest value-add parts of their business. Some were CEOs in title only. Some had stepped past CEO entirely and simply owned the agency like an asset.

I’ve heard about working ‘in’ versus ‘on’ your business for years, but seeing the two groups side by side helped me connect the dots.

I’m pulling in a concept my buddy Hans over at Termageddon has discussed with me. (If your clients need privacy policies or cookie consent, that’s his product, and it’s what I put on client sites.)

Below I’ve outlined the stages I see web designers go through. There’s some overlap, and you could break them into even more specific stages, but I didn’t want to get too nitty-gritty.

stages of a web designer2

Stage 1: The Friend of a Friend

Team: just you · Gross: $0, paid in exposure and thank-you dinners · Avg build fee: $0 to $500, usually a favor · Recurring: none · You are: doing somebody a favor · Barrier: surviving the first build and wanting more

Every web designer knows this person because, at some point, they were this person. The uncle who “does websites.” The nephew who set up the Shopify store. The friend of a friend who built a site for a lawnmower guy in 2014 and has been answering his hosting questions ever since, for free.

Payment is exposure, a thank-you dinner, a nominal fee if you’re lucky ($100 for a 10-page site), or nothing. The work happens at night, the sites are usually not great, and the maintenance situation is worse. Nobody’s keeping score, which is fine, because there’s no game yet.

This stage is the first barrier, and it filters people immediately. Some finish that first build, hate the whole experience, and never offer to build another website. Others catch the web designer bug. They start forming business ideas in their head, and they lose sleep thinking about the freedom of building things that live on the internet. Those are the ones who clear the first barrier every agency has to pass: you survived your first site build, and you still want to keep going.

The favor economy is where you build experience, one free WordPress install at a time. The stage ends the first time somebody offers real money.

Stage 2: The Side Hustler

Team: you, after hours · Gross: $2-30k/year · Avg build fee: $100 to $3,000 · Recurring: none · You are: moonlighting · Barrier: grinding until the leads get steady

Now there’s money: a few hundred dollars a project, then a few thousand. Still employed somewhere else, whether that’s an agency job, school, or something unrelated entirely. Some people land here from the other direction: they quit a job, start figuring out life, and build a few sites while they sort out what comes next. The work happens at 10pm and on weekends; the client roster is whoever the last client happened to know. Every scope gets hammered out over whatever channel the client used that day.

The tell at this stage is pricing: it’s whatever you feel the client won’t flinch at, often revised down mid-project out of guilt. Maybe $2-30k a year, all project work, no contracts, and when a client goes quiet, the follow-up is an awkward text two months later. It feels like real money because it’s found money.

This stage is a great filter, and it filters hard. Can you endure project after project, not making a ton of money, while watching yourself get better with every launch? That’s what stage 2 is actually about. It’s also a major learning stage: your end product takes shape here, the website stack you’ll lean on for years. You reuse the plugins and tools that worked on the last project on the next one, and around the tenth site, you stop reinventing the wheel. The barrier is surviving the grind long enough to establish a reasonably steady stream of leads and projects. Once that’s clear, the next stage starts when this becomes your full-time gig.

Stage 3: The Full-Timer

Team: 1, the whole org chart · Gross: $40-80k/year · Avg build fee: $2,500 to $5,000 · Recurring: a few $25/month care plans · You are: everything · Barrier: putting someone else’s hours on a client project

This is the scariest stage from the inside and the simplest from the outside. One person, full-time, doing everything: sales, design, builds, hosting setup, invoicing, and the 11pm panic when a client breaks their site the night before a trade show.

The full-timer is the CEO, the whole delivery team, and the help desk at the same time; clients see none of those distinctions. They see “my web person.” The money is maybe $40-80k a year if it’s going well, almost all project revenue, plus a few care plans of the $25/month variety that mostly pay for the panic work they cause.

Take a week off and everything waits for you: sales, edits, launch questions, invoices. There’s nobody else for anything to route through.

This stage can last a decade, and much of the industry’s burnout lives right here: one person absorbing every role, at a pay rate that never matches responsibility. There’s an identity wrinkle too. “Freelancer” starts to feel small, so people rebrand as a studio or an agency. Wearing the word agency without the structure is the most common stage confusion.

The ceiling is the calendar. Sales happens in the gaps between billable hours, so growth is capped at the number of hours in your week, literally.

The barrier out of stage 3 is the first time you put someone else’s hours on a client project. That means pricing high enough to pay a subcontractor and still make money, and putting your name on work you didn’t personally build. The calendar ceiling is brutal, but the handoff is what actually scares people.

Stage 4: The Stretched Solo

Team: 1 plus subcontractors · Gross: $40-150k/year · Avg build fee: $2,500 to $5,000 · Recurring: trickling in · You are: the ceiling · Barrier: learning to say no to out-of-scope work

Subcontractors appear; usually a developer first, maybe a designer, paid per project out of the margin.

Here’s the catch: the first time a subcontractor fumbles a launch or a site update, the owner takes the work back. Plenty of web designers stay in stage 4 for years, subcontracting during busy season and pulling the work in when quality slips.

This stage also teaches you the word no. In every stage before this one, you could say yes to almost anything and eat the cost yourself, working until 3am to figure out the solution on your own time, for free. Now a yes can land on someone else’s plate, and you need to pay them for their time, so you need to be more careful about what you say yes to. This is where you start saying no to work you don’t offer, and no to out-of-scope requests, even from clients you like. Saying yes got you here, but it can’t carry you further.

Gross gets to $40-150k, and some of it now comes through other people’s hours, which is the whole game starting, quietly. The next stage begins with payroll.

Stage 5: The Micro Agency

Team: 2-5, first payroll · Gross: $150-500k/year · Avg build fee: $2,500 to $10,000 · Recurring: $5-10k MRR if built in · You are: the glue · Barrier: defining your offering and sticking to it

Your first real hires happen. Two to five people, some employees and some contractors, but a team that shows up every week whether there’s a project or not. This is the smallest version of what has earned the word agency.

The owner is still in everything: first call on sales, final pass on QA, personal sign-off on every invoice. Delivery mostly happens through other people now, though, and for the first time, a two-week vacation doesn’t stop client work. Recurring revenue starts meaning something here too, because salaries need to be covered in the slow months. If care plans and hosting are built in, there’s maybe $5-10k of MRR sitting under the project work.

Capacity stops being the problem around here. The new problems are payroll, cash flow, and people.

This is where you define your offering and start sticking to it. Saying no, the personal skill you fought for in stage 4, becomes a company answer: we don’t do that. Maybe you niche down; maybe you stay industry agnostic on purpose. You give up on ecommerce, or ecommerce becomes the whole business. Your tech stack is relatively defined by now, whether that’s your own custom theme or a starter you’ve refined across dozens of sites. Scope creep gets managed in real ways: change orders, a scope doc, a price for every ask. And once you can finally say what you are, the owner’s attention turns outward for the first time: getting in front of more of the right people becomes the new project.

Stage 6: The Founder-Dependent Agency

Team: 5-15 · Gross: $500k-$2M/year · Avg build fee: $5,000 to $15,000 · Recurring: growing, but attached to you · You are: the bottleneck · Barrier: building SOPs and getting people to use them

From the outside, it’s a real business. Five to fifteen people, distributed or in an office, a portfolio site, revenue somewhere between $500k and $2M a year.

Here’s what separates stage 6 from stage 7: what actually happens when you’re not around. At stage 6, sales stop, decisions stack up, and key clients get nervous because, in their mind, the relationship lives with you personally. Your company is the invoice header. Your second-in-command spends your whole vacation texting you anyway. The business looks independent, but it isn’t. Everything runs through the owner at slightly less intensity than it used to, and slightly less intensity feels like progress.

Here’s what makes stage 6 hard to see from the inside, though: it usually feels like winning. Revenue is the best it’s ever been. The team is busy. Clients are happy, and they’re happy specifically because they get you. The things an owner is proudest of at this stage- the relationships, the reputation, being the reason people sign- are the same things holding the ceiling in place. Nobody plans their way into stage 6. They drift into it, usually over a decade, one loyal client at a time.

I’m not pretending my agency is fully independent either. My agency, CyberOptik, manages 800+ WordPress sites with a real team and 16 acquisitions behind it. I still handle our sales and business development (including acquisitions), and I’m still the name plenty of clients think of first. The agency depends less on me, but it’s not independent.

Getting from stage 6 to stage 7 is often the hardest jump of the nine because, for the first time, the next stage requires giving something up instead of adding something. Every stage before this one was accumulation: clients, people, revenue. 

Stage 7 is subtraction. It starts with documentation: SOPs that turn how you do things into expectations a manager can hold people to. A manager hired to replace parts of you is a payroll expense that makes the business look worse for a year or two before it makes it sellable at all.

Stage 7: The Managed Agency

Team: 15-40, with a leadership layer · Gross: $2M+/year · Avg build fee: $10,000 to $25,000 · Recurring: real, team-owned · You are: the direction-setter · Barrier: stepping back while you still own it

A leadership layer now exists between the owner and the work. A delivery lead who owns quality and capacity. An ops person who owns billing and the help desk. Maybe a salesperson whose name clients actually know.

Take two weeks off now, and decisions still get made. Some of them are ones you wouldn’t have made. That’s the cost of stage 7: delegating real authority means living with the outcomes. Founders who can’t stomach this slide back to stage 6, and they usually call it quality control.

At stage 7, work runs through systems instead of memory. SOPs spell out how you and leadership expect the work to happen. Billing is managed. Project time gets tracked. Problems still surface, but they usually reach you as reports, patterns, or numbers before they become fires. And somewhere in here, the team starts passing you. Your developers explain things you can follow but couldn’t do yourself without spending a lot of time figuring them out. That’s normal here, and it’s the point. You hand a lot of trust to key staff members, and they have to keep earning it.

Revenue is typically $2M+ by now, and the business’s character has changed along with it. The earnings survive the founder’s vacation schedule now: the founder is one input among many, and the company finally functions as one. This is also the stage where growing by acquisition starts beating growing by marketing, which is exactly what happened to us: the acquisitions we do now matter more to our growth than any campaign we’ve ever launched.

The failure mode at this stage is the org chart. Fast growth after delegation exposes whoever got promoted one stage too early. The signature version is a leadership team in name only: managers with titles but no authority, which quietly means the founder never left.

Stage 8: The Self-Running Agency

Team: leadership-run, 30+ typical · Gross: $10M+/year · Avg build fee: $15,000 to $40,000 · Recurring: the core of the business · You are: an asset owner · Barrier: deciding what the business is for

The owner has exited day-to-day operations. Fully staffed agency, a leadership team that owns outcomes, and an owner whose involvement is direction and capital: key hires, partnerships that feed the business, the numbers, and maybe acquisitions.

Some go further and step past CEO entirely, and “just” own the business. The M&A event I mentioned at the start had a few of these: owners who aren’t in the day-to-day of their agencies. They own businesses the way someone owns an apartment building, and their calendars prove it.

Revenue alone doesn’t put you at stage 8, since the stage is about what runs without you, but self-running agencies typically sit somewhere in the $10M+ range. By this point, the agency no longer depends on any one person’s calendar, including the owner’s, and that’s the real product: income that keeps arriving whether or not the founder shows up on Monday.

The failure mode at stage 8 is drift. The machine runs, clients stay happy, and the curve flattens anyway, because a business built to run without its founder still needs somebody deciding where it goes. Owners who step out without installing that person usually coast for a while before they notice the curve flattening.

Stage 9: The Acquirer

Team: leadership team plus acquired teams · Gross: stage 8 base, then step-jumps from deals · Avg build fee: bespoke; MRR matters more · Recurring: what gets bought and kept · You are: the buyer · Barrier: none left; from here it’s choices

Past stage 8, the owner faces a choice that the lower stages never get to make: keep earning from the business, grow it by buying other agencies, or sell it and walk.

The logic behind buying agencies is worth slowing down for, because it explains every roll-up you’ve ever heard of.

You can grow a client base one sale at a time, or you can buy a book of recurring clients in one stroke. One sale at a time is slow and uneven: a good quarter, a flat year, another good quarter. When we started acquiring agencies in 2019, our recurring revenue started arriving in steps. Each deal added a block of care plans and hosting clients that would have taken years to sell one at a time, and every big advertising holding company got built the same way. The names on the buildings change. The method underneath is always some version of the same three moves: buy the client book, keep the clients, do it again.

That’s why a room full of owners was downtown comparing notes on buying agencies.

You don’t need a pile of cash to play this game, which is the part most designers assume. My deals are earn-outs: 80-90% of net MRR paid over 24 months, tied to retention, with no big upfront check. It’s the small-agency version of the same play the big players run, minus the private equity.

Stage 9 comes in two flavors, depending on the kind of agency you built. Industry-agnostic agencies usually grow by buying other generalist shops and folding their recurring clients into one operation. That’s been our playbook at CyberOptik. A niched agency plays the same stage differently. The objective becomes dominating the industry it serves, which might mean buying other agencies in the same niche, buying near-adjacent firms, or using the same playbook to enter a new niche entirely.

Seen from up here, the whole pattern comes into focus. At every stage, what a buyer is shopping for is how much of the business survives the owner’s absence. Favor websites have nothing to hand over. A solo’s clients can earn a referral fee. A micro agency’s care plans can carry a 24-month earn-out. A stage 6 agency has a person standing in the middle of everything, and buyers can see it from across the street. A stage 7 agency has a machine with people in it. A stage 8 agency is the thing the entire acquisition industry exists to buy. The stages of a web designer are really the stages of removing yourself from your own business, and the market pays for that removal at every single stage.

The Seller: A Path You Can Choose at Any Stage

Sooner or later, most owners think about selling. It can happen between any of these stages.

Two things matter more than anything else: how much of the business runs without you, and how much recurring revenue it brings. The more you’ve removed yourself from the daily work, the cleaner the transition feels to a buyer. The more care plans, hosting clients, and retainers riding along, the stronger the payout can be.

When selling becomes real, the work turns practical fast: clean accounting, clear client lists, documented recurring revenue, written agreements, and a plain explanation of what the buyer is actually buying. Owners who do that prep usually sell with less stress, because the buyer doesn’t have to untangle the business while valuing it.

If that door is on your mind, those conversations are confidential and zero-pressure. Worst case, you leave knowing your number. Here’s where to start.

What AI Is Doing to These Stages

AI is pressuring these stages from both ends.

At the bottom, the barrier to entry is much lower. Building a website used to take some level of skill; now it takes a prompt and a credit card. Stage 1 and stage 2 are about to get a lot more crowded, with people who have never debugged a plugin conflict, never migrated a site, never taken the 9pm call because a client’s checkout broke. They’ll do work they don’t know is bad, for clients who can’t tell the difference, and the cleanup work lands on whoever comes next.

At the top, agencies with real systems run the same tools across hundreds of sites at once, 800+ in our case, with QA and accountability behind every change. A solo WordPress designer using AI to build one site faster ends the day with the one site.

The middle thins out. The bottom gets bigger, the top gets more efficient, and stage 6, the founder-dependent agency, gets squeezed from both directions: commoditized from below, outpaced from above.

There’s No Wrong Stage

One thing I want to be careful about: this list is not a lecture about everyone needing to reach the top. Stage 3 with a full calendar and rates you control is a genuinely good life. Plenty of people land at stage 6 on purpose, like their team, and never want to buy or sell anything. The stages only matter if you want what’s further along. My suggestion is to know which stage you’re in, because the one mistake I see over and over is people thinking they’re further up than they are.

And if the next stage isn’t one you want to reach, that’s a legitimate call too. Selling can happen from almost any of these stages, and earlier than most owners realize.

The guys in that downtown room all started at stage 1 too. Somebody built a website for somebody’s uncle.

FAQs

How do I know which stage I’m in?

Match yourself to the barrier you’re fighting right now:

  • Stage 1: you said yes to building a site and had no idea what you’d actually agreed to.
  • Stage 2: you keep saying yes to requests you know, deep down, are outside the scope.
  • Stage 3: every hat in the business is yours, and sales happens in the gaps between billable hours.
  • Stage 4: a subcontractor fumbles a launch, and your first move is pulling the work back in-house.
  • Stage 5: client work continues while you’re away; sales stops the day you do.
  • Stage 6: decisions stack up, clients call your cell, and your second-in-command texts you through your vacation.
  • Stage 7: you come back from two weeks away to decisions you wouldn’t have made, and the business is still standing.
  • Stage 8: you could disappear for a month, and the team keeps shipping, clients still get answered, and payroll still runs.
  • Stage 9: you’re reading this while sizing up which agency to buy next.

Whichever line stung a little, that’s probably you.

Can I sell my web design business if everything depends on me?

Yes, though you wouldn’t be able to ask for as much. Founder dependency is a risk for the buyer. What sells well is recurring revenue plus relationships that can transfer to a team. Many founder-dependent shops still close through earn-out structures, where the payout is tied to clients actually staying, so the transfer of trust gets proven rather than promised.

Can I skip stages?

You can compress them, and people do, but skipping one tends to show up later. Some people get lucky, too: a connection hands them a big client, a steady referral source, or a small book of recurring work years before they would have earned it on their own. 

You never need to turn down a lucky break, but you’ll still have lessons to learn. Each stage teaches something the next stage assumes you know, and the ones you skipped have a way of surfacing when they’re most expensive: how to price, how to spot bad work before a client does, when to trust someone else with a launch.

Do I need recurring revenue to be sellable?

For a true acquisition, close to it. Without care plans, hosting, or retainers, you don’t have a transferable income stream; you have a pipeline of past clients, and those deals usually become referral or commission arrangements instead of acquisitions.

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