June 24, 2025

153: How To Turn One-Off Projects Into Monthly Retainers

Wondering how to get monthly retainers and stop chasing one-off gigs?

John knows! You can follow his lead by learning how he 3x’d his income, pitched retainers with ease, and built long-term client income.

Show Notes

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Want to stop chasing one-off gigs and start building predictable, recurring income?

John MacAdam reveals how.

He built his side hustle over 15 years while working full-time as an engineer — and eventually used it to launch a successful solo business.

You can follow John’s lead after hearing how he:

Shifted from hourly rates to value-based pricing — and tripled his income
Turned a $6K one-off project into a $5K/month retainer (still active 2+ years later)
Positions himself as a trusted advisor, not just a task-doer
Uses simple systems to build long-term client loyalty
Turned early failures — like a “your app sucks” review — into growth and momentum

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Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things.

How to Turn One-Off Projects Into Monthly Retainers

If you're a freelancer or side hustler tired of chasing new clients every month, it's time to rethink how you price and position your services. Instead of constantly pitching and proposing one-off projects, what if you could transform those short-term gigs into long-term, monthly retainers?

John MacAdam — a former full-time engineer turned full-time solopreneur, shares how he made that shift.

The result?

He 3x’d his income, replaced the uncertainty of sporadic projects with predictable cash flow, and built stronger, more collaborative client relationships.

Here’s how you can do the same.

Why One-Off Projects Hold You Back

When you're charging by the project — or worse, by the hour — you’re stuck in a cycle:

Constantly looking for the next job
Re-negotiating your value over and over
Burning time managing scope, expectations, and deliverables

Worse still, one-time projects rarely give you the space to build deep trust with clients, which is where your highest value lies.

John learned this firsthand. For over 15 years, he ran his side hustle while working full-time as an engineer. He undercharged for far too long, until a mindset shift changed everything.

The Mindset Shift That Tripled His Income

Instead of asking, “How much is my time worth?” John started asking:

What value am I delivering to the client?
How will this project impact their bottom line?
What’s the strategic outcome — not just the task?

That one change led him to raise his prices from $2,000 per project… to $6,000, then $10,000 — and clients still said yes.

Why? Because he positioned himself as an advisor, not a task-doer.

The First Retainer: A $6K Project Becomes $5K/month

One client initially approached John for a single $6,000 project. After delivering value, they came back with six more.

Rather than quoting each individually, John proposed a $5,000/month retainer — with defined scope, deliverables, and value-added strategy built in.

They said yes.

That was over two years ago — and the client is still on retainer today.

How to Turn Your Projects Into Retainers

1. Start With Value, Not Time

When quoting a project, reverse-engineer what it's worth to your client. If it can help them make $60K, you’re justified in charging $6K–$10K.

2. Deliver Early Wins

Build trust by overcommunicating, hitting deadlines, and showing strategic thinking. Clients will want to keep you around.

3. Pitch Retainers as a Win-Win

Once a client is happy, offer two options:
- Pay per project
- OR go on a monthly retainer for flexibility, priority access, and ongoing results

Frame it as value + stability, not just more work for you.

4. Set Expectations and Structure

Define:

Scope of work
Communication cadence
Hour caps (if needed)
Review points (e.g. monthly or quarterly check-ins)

This prevents scope creep and keeps the relationship healthy.

What to Do When You Get Negative Feedback

John’s journey wasn’t all wins. His first app? One of his first reviews was brutal:
"Your app sucks. I want my dollar back."

But instead of quitting, he responded respectfully, asked for feedback, and improved the app. That app went on to earn over $10,000 — and sparked a relationship with a long-term client.

The takeaway? Don’t be afraid of failure. Learn, adapt, and keep moving forward.

The Power of Small, Consistent Action

John committed to doing one thing a day for his side hustle — even if it was just submitting an app to a showcase site or writing code for 20 minutes before work.

One of those “small” actions? It led to his highest-earning client ever.

Consistency beats perfection.

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