I Put My Stress on a Subscription Plan: The Retainer Mistakes Nobody Talks About
Solopreneur Letters #3
Everyone says: build recurring revenue.
They’re right. Projects end. Bills don’t.
Retainers can give you stability.
I did that part well.
I locked in ongoing clients.
I avoided the feast and famine cycle that crushes a lot of freelancers.
But here’s the part I missed: recurring revenue only buys freedom if the numbers and the boundaries are right.
Otherwise… you’ve just put your stress on a subscription.
The Story
Early on, I set up a couple solid retainers.
Strategy. Funnel work. Email.
Good scope on paper.
Then two things happened:
All of a sudden my “stable base” was 90% of my calendar, but only 50% of the revenue I needed.
I was the dependable person who could “just take care of it for now.”
Helpful in the moment.
Miserable long term.
The result: I had monthly money… without margin.
Not enough to survive.
Not enough to even breathe.
And definitely not enough time to build my own assets or grow my list the way I knew I should.
Recurring revenue done wrong is just recurring stress.
Why It’s a Mistake
A retainer is supposed to buy three things: cash flow, focus, and time.
If it only buys cash flow, you built a job.
If it buys cash flow and eats your time, you built a low‑paid job.
Two hidden costs show up fast:
Pricing drag: a “starter” rate becomes your identity. You stop raising it because the client is nice… because you said yes once… because it feels risky to rock the boat.
Positioning drift: low‑level tasks sneak in. Follow ups. Calendar syncs. Customer service. Report chasing. You become the operator, not the architect. The busier you get… the less valuable you look.
Now layer in one more truth: recurring commitments compound.
Even small undercharges and small scope leaks multiply month after month.
That’s how “stable” becomes “stuck.”
Build Retainers That Create Freedom
What I wish I had told myself on day one:
1) Price for margin, not survival.
Charge more than you think you should. Then sanity‑check with capacity math:
Decide your monthly revenue target.
Reserve 25–30 percent of your hours for your own list, products, and thinking. Non‑negotiable.
Divide the remaining hours by the number of clients you want.
If the effective hourly falls below your target… raise the rate or shrink the scope.
2) Define the container — and keep it sealed
Retainers should buy clearly defined deliverables that lead toward a measurable outcome.
That’s different from “unlimited support” or “whatever you need.”
Access creeps. Scope creeps.
And when they creep, your margins die.
Decide your core container and name it:
Strategy: monthly roadmap + priorities call
Production: one major asset shipped per month (sales email sequence, landing page revamp, offer test)
Insight: one KPI report that’s automated so you’re the analyst, not the admin
Then tie those outputs to the business results they support (higher conversion rate, more leads, faster sales cycle).
3) Be the architect, not the operator
Your value is in designing the system, not pushing the buttons forever.
If something must repeat, document it, hand it off, and step back.
And unless you’ve explicitly taken on a CMO/COO/CFO role, you are not the client’s manager of freelancers.
If you don’t want to run a team for yourself, don’t get sucked into running one for someone else.
4) Build upside into the deal
Sometimes there isn’t a “step up” to sell since the scope is already maxed out.
In that case, protect your base rate for the ongoing work…then add revenue share for hitting agreed benchmarks.
Example:
“I’ll manage X campaigns per month for $____. If we hit Y% increase in monthly revenue from these campaigns, I get Z% of the lift.”
It turns your role from flat-fee labor into a growth partner with shared incentives.
5) Fence in communication
Office hours.
Response windows.
One channel for day-to-day.
Emergencies defined up front.
Chaos costs you your best thinking, and that’s what the client is really paying for.
If You Love Stability… Protect It
Recurring revenue in the form of retainers is only freedom when it funds your best work and protects time for your own assets.
That means:
The price respects your value
The scope protects your positioning
The structure creates time, not consumes it
Otherwise you’re renewing stress every 30 days.
A Simple Script For New or Existing Clients
“Here’s how my ongoing work is structured: you’re buying outcomes. Each month we set priorities, ship one revenue‑driving asset, and review the key numbers. Admin support isn’t included. If you need that, I can recommend a great EA service. Every 90 days we review scope and pricing so the engagement stays aligned with results.”
Clean. Respectful. Clear.
The Line I Wish I Had Drawn Sooner
Retainers are not the goal.
Good retainers are.
They should pay enough to breathe… focus on the work that moves revenue… and leave you time to build the business you actually want.
Get those right and recurring revenue becomes what it’s supposed to be: a platform you stand on while you build something bigger.
This is Letter #3 of 'Solopreneur Letters' – a series I’m writing where I share the hard-earned wisdom I wish I’d had when I started on my solopreneur journey. See the full list:
