Work Shape: Why Retainers Work for Some (Not Others)

⚡️ The Subscription Myth

Every fractional hits this wall: your work is booked out, your calendar is full, you’re making good money, and somehow you still feel underwater.

That’s the subscription trap — retainers that feel like quicksand.

The issue isn’t recurring revenue. It’s weak boundaries. Here’s how I fixed it.

Retainers Aren’t for Everyone (And That’s Fine)

If your expertise is episodic — brand identity sprints, creative campaigns, strategy engagements — retainers might fundamentally conflict with how your best work happens. You’re not doing them wrong. They might just be wrong for you.

But if your discipline is iterative — product design, ongoing advisory, operational support — retainers can work beautifully. The issue isn’t the model. It’s how you structure it.

This post is for the second group.

The Quick Diagnostic

Before you dive into structure, it helps to check your work shape.
Answer these three questions honestly:

Do your projects build on each other month over month, or reset from scratch?

If they compound, retainers might fit.
If they reset, you’re likely better off project-based.

Does the second month of a client engagement feel easier or duller?

Easier = compounding value.
Duller = your work is episodic — finish strong and move on.

Do you spend more energy managing deliverables or maintaining direction?

1. Deliverables point to sprints and flat-fee projects.
2. Direction points to iterative partnership.

If you said compounds, easier, direction, you’re in the right place.

💬 How I Structure Mine

(Product Design + Branding)

Everything below comes from my own disciplines — product design and branding. But the principles apply across any fractional practice. Deposit, cadence, clear scope, separate agreements for separate work. Adapt the mechanics to your own work shape.

I do product design and branding, but they’re completely different shapes of work.

Product design is iterative — strategy + execution, constant feedback, ongoing cycles, quick iteration. I work in 3–6 month minimums.

Before kickoff, I take a deposit for the first month. Then, on the 1st of each new month, I send an invoice due in 30 days. That rhythm keeps cash flow clean and headspace clear.

Predictable work = predictable energy.

I don’t call it a retainer or advisory. I just say:

“Here’s what you get each month. Here’s how I work.”

It’s like heartbeat scheduling, a steady cadence that keeps everyone in sync.

Branding: A Different Shape

The key difference: product design is ongoing partnership. Branding is finite craftsmanship. One compounds. One completes. That’s why they need different money conversations.

Branding, site design, and decks live in their own lane. Flat fee. Fixed scope. Clear start / stop. Separate agreements. Separate expectations.

If a client wants to add something, I give them options:

“We can extend what we’re doing at the same cadence or scope a new project properly.”

Clear choices. No fuzzy middle ground. No silent scope creep.

🧠 Stop Making Decks

I don’t use decks to present work (outside of branding), run workshops, or send proposals anymore. I’ve tried everything — Notion, Looms, slides — and none of it made the work better.

Most sessions happen live in Figma/FigJam, where we build ideas in real time.
Proposals are just emails, five to ten minutes tops.

It’s how I’ve closed six-figure work.
Clarity beats polish every time.

🔐 Why Retainers Fail (and How to Fix Them)

Most fractionals don’t burn out because of bad pricing.
They burn out because of bad boundaries, the “all-you-can-eat” model.

🧠 Netflix thinking: flat fee = unlimited access
🕒 Scope creep: “Quick question” = ten invisible hours
💸 Cheap comparison: price like software → get treated like software

I’ve been there. My first setup looked perfect until I realized I’d built an all-inclusive resort for client requests.

Now I design boundaries the way I design products: clear components, defined limits, smooth handoffs.

Clients respect the fenceposts. They don’t want unlimited. They want reliable.

⚖️ Value vs. Time Is Not Either/Or

Smart fractionals blend both models.

Charge monthly for ongoing partnership, and add project fees for big pushes.
Predictable revenue and high-ticket upside, side by side.

Founders know the difference between SaaS and senior leadership.
The key is positioning: clear scope, firm limits, partner posture not vendor vibes.

🪴 When the Big Push Is Done

After a heavy lift, I don’t shut it down. I downshift.

Fewer calls, slower cadence, but the relationship stays alive.
I call it maintenance mode.

This is where most fractionals miss the real play. After the big push, they either ghost or restart the cycle. I do neither.

I’m still in the room for key reviews and product decisions, just not pretending it’s a full build anymore.

Usually it’s about half the hours, half the cost, and 100% sanity.

It protects my time, keeps their momentum, and when the next big push comes, I’m the first person they call, not someone new who has to learn the system from scratch.

🛠 The Hammer Rule

A reader said it perfectly:

“A retainer is like a hammer. Used right, it builds the house. Used blindly, it smashes the wall.”

The tool isn’t the problem. It’s how you use it.

🧩 Why This Works

Because boundaries are value.

When you lead with structure, deposit, cadence, and scope clarity, you stop selling hours and start selling predictability.
And that’s what premium clients actually buy.

⚙️ Real-World Example

People often ask what my client emails look like.
Here’s the simple version of what I send, and what you can adapt for your own discipline.

Retainer Proposal Email

Subject: [Client or Company Name] – [Project or Partnership Proposal]

Hi [Client First Name],

Really enjoyed our conversation this week. It gave me a clear sense of where your [business / product / team] is heading and how [your skill or role] can support that next phase.

From our chat, here’s how I’d approach the next phase together.

Our Focus
[Write 2–3 sentences about what you’ll help them achieve.
Example: “Clean up the marketing foundation so your team can ship faster and stay consistent.”]

This phase will:

• [List 2–4 simple things you’ll do each cycle. Example: “Clarify priorities,” “Tighten up messaging,” “Improve the customer flow.”]
• [Last item: “Keep strategy and execution in sync so nothing stalls.”]

Team & Structure
[Briefly name who’s involved — just you, or you + collaborators.]
Example:
“I’ll lead strategy and direction. If needed, I’ll bring in trusted collaborators for production or research.”

We’ll run this as a focused, high-touch engagement with visible progress from week one.

Timing & Budget
Suggested kickoff: [Month or timeframe]. This sets us up for a clean start leading into your next milestone.

Budget Options

6-Month Partnership – $[XX,000] / month
Best for consistent progress and deeper integration.

Month-to-Month Engagement – $[YY,000] / month
Best for flexibility or milestone-based work.

Both options include:

• [What they get each month: “Clear goals and updates” / “Weekly touchpoints” / “Async reviews”]
• [How you work: “Fast feedback loops” / “One main point of contact”]
• [Boundaries: “Defined scope, no surprise extras.”]

Either structure gives you predictable progress and a calm working rhythm.

Let me know which direction feels like the best fit, and I’ll send over a simple agreement to lock in timing.

Appreciate the thoughtful conversation. Excited about what you’re building and how we can help bring this next chapter to life.

Best,
[Your Name]

Downshift to Maintenance

Subject: Next Phase – Maintenance Mode

Hi [Client First Name],

Now that the new [thing you built] is live, I’d suggest shifting into a lighter rhythm for a while.

That usually means:

• One weekly check-in call
• A few async reviews
• About half the hours (and half the cost)

It keeps things moving and gives both sides breathing room while maintaining consistency. If that sounds right, I’ll outline it and we can lock in the next phase.

Best,
[Your Name]

👋 Closing Note

If this helped you rethink your structure, forward it to a friend building their own fractional practice.

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