I stared at my bank statement for 20 minutes, repeatedly logging in and out thinking the numbers would somehow change.
Here’s what happened:
The client needed a new version of their entire website. This included 15 web pages, brand messaging and a full SEO search engine optimization campaign.
It took me 4 days to write this proposal. I built a customized pricing outline based on all of the work that would be done (proposal prep, research, writing, revisions, etc.) created mockups of their homepage, researched all of their competition and wrote a three-page strategy document explaining exactly how I would improve their conversions.
They hired me right away.
I billed them $1200.
After I calculated all of my hours (proposal prep, research, writing, revisions, project management, client calls), I earned an average hourly rate of $47 per hour for my billable hours. But the truth is, none of those hours were really billable hours.
Half of those hours are what could be classified as “business development” which wouldn’t even exist if I didn’t have clients that left after they paid for services.
I completed the project in 21 days. They loved the final product. Sent a glowing testimonial about working with me and referred someone else to my business. That referral person never replied to any of my follow up emails.
Then nothing.
I went back to UpWork and started refreshing my proposals, looking at all of the other freelancers undercutting my prices, and asking myself why I couldn’t just get a regular job.
At that breaking point, sitting at my kitchen table at 11pm, staring at my bank balance and realizing I may have approximately six weeks before I will need to start dipping into my savings again, it changed everything.
It wasn’t because I came up with a brilliant plan to fix everything. It was because I became sick of my own BS and had to try something new.
The Feast-or-Famine Cycle Nobody Warns You About
Here’s what they don’t tell you about freelance work.
It’s Not the Work That Will Destroy You. It’s Getting the Next Project.
The actual process of creating an assignment for a client can be very enjoyable. But what happens after the project is completed, and the client pays their bill, and then you never hear from them again?
That is when the real grind begins; now you are right back to where you were before, and you will be starting all over again. Pitching for your next job, making those sales calls, writing up another proposal that may or may not lead to more of the same.
And, as if it wasn’t bad enough that you are always looking for the next job, the fact remains that every client has to be onboarded, which means there will be another discovery session, another set of project management tools to learn how to use, and another mountain of research to climb to come up with some new ideas, and somehow find the creative energy to make it happen.
And even when you finally win that next gig, you’re still just getting started.
In 2013 I spent two months tracking my time as I worked.
What I found was that:
38% of the time I spent on freelance work was time spent on client billed work
29% of the time I spent on freelance work was time spent on proposals for work I did not win.
18% of the time I spent on freelance work was time spent doing administrative things and managing each of my projects.
15% of the time I spent on freelance work was time spent on “business development” i.e. networking, content creation, etc., for potential future work.
I was spending fifty hours per week on my freelance business, but I was only getting paid for nineteen of those fifty hours.
When I had three clients, I earned a lot of money, but I burned out because I was juggling three different onboarding processes, communicating with three different types of people, and having to revise three different projects at the exact same time.
When I had either one client, or no clients, I was panicking. I would drop my rates. I would take jobs that I hated. I would work with people that treated me poorly because I needed the money.
You already feel this way. The dread you feel when you complete a successful project knowing exactly what you’ll have to do next.
The anxiety that builds up into full-blown panic attacks that begin on Wednesday night, about Monday morning, wondering where the income for the following month will come from.
The exhaustion of being incredibly talented at your profession, but utterly inept at keeping your freelance business running.
The Shift That Changed My Bank Account (And My Sanity)
It was not an idea I learned from a business class. I stole it from a conversation I heard while I was sitting by myself in a hotel breakfast room, eating what had to have been the worst scrambled eggs in the world, trying to pretend like I was not listening in.
An agent told another agent at a conference in Austin (while I sat there, faking like I did not hear) “we no longer take on projects.” “All we do are retainers now,” he said. “If they want a one-time job, we will give them your name.”
Those words made me get mad, but not in a good way.
How nice, I thought to myself. To be so successful that you can say “no” to people wanting to hire you.
However, I could not stop thinking about those words. Was it possible that I was wasting my time trying to find more clients? Or was it because I keep getting clients who only need one thing for one time?
I then looked through all of my past clients. In eighteen months I had done thirty-two projects with four repeat clients.
I was focused on the wrong metric. I was celebrating new clients instead of developing systems and processes to make sure my clients would come back and stay.
So, I did something difficult. I stopped doing one-off projects.
I did not stop doing one-off projects because I was confident or clever. I did it because I was tired.
I reorganized all of my services into three monthly retainer based packages. I assumed I would lose almost all of my potential clients.
Instead, something strange happened. My closing percentage went up.
When prospects asked me how much the price would be for their first month of service, I could tell them exactly. When prospects disappeared after completing their first month of service, I knew why.
The relationship between us was designed to last beyond their first month of service. I did not spend as much time selling new clients to replace the old ones because I was not constantly losing and gaining clients.
My income did not just go stable. It multiplied. Within six months of switching to a retainers-only model, my average monthly income increased from $3400/month to $11,200/month. This is not because I worked more hours. I stopped working on the wrong things.
The Three Retainer Packages That Actually Convert
Here’s the structure that worked for me which I also suggest for you to try.
Package One: The Content Engine ($1,500/month)
This was for businesses that needed consistent content but didn’t want to hire a full-time writer.
What’s included:
4 blog posts per month (800-1,200 words each)
8 social media posts (LinkedIn or Instagram, client’s choice)
1 monthly strategy call (30 minutes)
Unlimited revisions on current month’s content
Content calendar planned one month in advance
What’s not included:
Graphic design (you can partner with a designer and refer clients to them)
Video scripts (different skill set, different pricing)
Email sequences (see Package Two)
Ad copy (also Package Two)
SEO optimization beyond basic keyword usage (you can get a specialist for this)
Why it worked: Businesses with blogs have an endless need. Four posts a month was enough to maintain momentum but not so much that you’d drown in research. The social media posts are used to repurpose blog content, so there’s no creating from scratch eight extra times. The strategy call is to keep you connected to client’s goals without constant Slack interruptions.
I’d position this as “you’ll never have a dead blog again” instead of “I’ll write four posts.” Framing matters.
Package Two: The Email Authority ($2,200/month)
For businesses building or nurturing an email list.
What’s included:
4 weekly newsletters (500-800 words)
1 monthly email sequence (5-7 emails, usually for a launch or promotion)
Email list audit and recommendations (first month only)
Subject line A/B testing suggestions
1 monthly strategy call (45 minutes)
What’s not included:
Email platform management (they will have to DIY or you refer help to them)
List building strategies (different expertise)
Graphic design for emails
Automation setup beyond basic sequences
Why it worked: Email is intimate. It requires consistency. Most businesses know they should email their list but don’t because it’s time-consuming. This package solved that problem completely.
The monthly sequence is the secret weapon. It can create urgency and variety in your work. It also gave clients a reason to stay subscribed. They’d plan launches around knowing they had email support.
Package Three: The Full-Stack Content Partner ($4,500/month)
For clients who needed someone to own their entire content strategy.
What’s included:
Everything from Package One and Package Two
2 case studies or long-form pieces per month
Monthly content strategy meeting (90 minutes)
Quarterly content audit and recommendations
Direct Slack access during business hours
Priority scheduling for rush requests
What’s not included:
Website development
Paid ad management
Social media community management (responding to comments, DMs)
Video production
Why it worked: This package attracted clients who valued partnership over transactions. They weren’t buying words. They were buying strategic thinking and reliability.
If you are not hiring anyone to do this, you may wish to take two of these clients at a time because the Slack access and strategic meetings will require real attention. But two clients at $4,500 each meant $9,000 in predictable monthly revenue.
The quarterly audit is like the finale for retention. Every three months, present a full analysis of what is working, what isn’t, and what you should do next. It is there to remind them of the value you bring and gives you permission to keep improving your work.
Mistakes I Made So You Don’t Have To
The whole time in my career, I’ve tried so many things, such as the packages that I recommended to you here. Along the way, I’ve made countless mistakes and I don’t want you to go through that. Here are some of that:
Error 1: I did not define the limits of the “unlimited revisions”
One client in my first Content Engine package asked for 14 rounds of revisions on a single blog post. I let it happen because the package had said “unlimited”, and I was worried about losing them.
I lost $680 in hourly value on that one piece of content.
My packages now read: “You can have unlimited revisions on your current month’s content as long as you ask within reason. Requests for major rewrites or scope changes will be reviewed individually.” “Within reason” has helped save my sanity many times since.
Error 2: I undervalued my services to avoid being fired
My first Content Engine package was priced at $800 per month. I thought that was a good price. It was not. I was providing $2000+ in value and asking for less than 1/3 of it.
After three months I raised prices. The two remaining clients paid the new rate and the one that left was replaced by someone willing to do so within two weeks.
Your pricing does not reflect how much you think you are worth. It reflects the clients’ desire to achieve the desired outcome regardless of the cost.
Error 3: I did not create time for creative rejuvenation
For four months I worked at maximum capacity. I had five Content Engine clients, one Email Authority client, and I was consistently working against deadlines.
I hated writing.
Writing used to be something I enjoyed. With client work, it was something I loathed. The reason was that I never took a break from thinking. I was always producing. Never creating.
Today I limit my retainer clients and block off Fridays for strategic planning, education and creative projects that are not for a client. Since I have been doing that, my writing has improved. My ideas are more sharp. And my clients have received better work.
Error 4: I accepted all the clients who were willing to pay me
Not all clients will become retainer clients.
There are some clients that may only need your help on a one-time basis. There is nothing wrong with that. However, I spent months attempting to turn project-based thinkers into retainer clients. They did not want a partner. They needed a task to complete.
It’s all about working with the “ideal client”, not just any client.
Currently I qualify my leads with the following question: “Do you need help with a one-time project or ongoing content development?”
If they tell me one-time, I send them to other freelance writers. If they tell me ongoing, then we discuss which package would best fit their needs. Pre-qualifying potential clients in this manner prevented me from forcing relationships that would never have existed.
Error 5: I did not develop documentation of my business processes
When I began getting retainer clients, I was treating each client as if they were a one-off project. I created a new file structure. A new communication model. A new everything.
It was chaos.
Finally, I developed templates for: Onboarding Questionnaire; Content Calendar; Strategy Meeting Agenda; Monthly Report; Revision Request Form.
Developing these templates did not take away from the creativity of my work. It allowed me to use my brain for the creative aspects of my job rather than spending my time developing new ways to accomplish administrative tasks.
How to Actually Transition Without Losing Your Current Clients
You can continue to grow your business without blowing it up.
Begin small by selecting your top client from the past year (the one that has consistently employed you). Select the client that is your favorite and would love to work with for years to come.
Email the client and send them something such as: “I have truly enjoyed the opportunity to provide you with content and copy for [specific projects] and I am changing my business model so I can offer Ongoing Partnerships instead of individual projects. I have developed a Retainer Package for businesses similar to yours that require consistent [content/copy/strategy]. Would you be available for a quick phone call so I can explain to you what this retainer package may look like for your business?”
Half of the time they will tell you NO. That is perfectly fine. This is about building a base for future referrals, not converting every single person into a paying customer.
When someone tells you YES. Present ONE option for a retainer program. Not 5 options, not 3 options... ONE clear option with clearly defined deliverables and clearly defined boundaries.
After delivering excellent service for 3 months, ask them for a testimonial and a referral. Retainer clients generally have other businesses that need retainer services.
New Leads: Stop providing project-based work completely. If someone contacts you asking for a one-time project (i.e. “Can you create me a website?”, “Can you create me an email campaign?”), let them know: “Due to changes in my business model, I only take on clients on a retainer basis at this point. However, I would be happy to refer you to a number of talented individuals that do great one-off work. Additionally, if you are looking to establish an ongoing relationship, I would be happy to discuss further details on how I work.”
Many people will choose to leave your business due to the change in structure. Most will appreciate your honesty and transparency.
Those that remain are most likely people that genuinely care about your ability to assist their business.
What This Actually Looks Like Six Months In
I am not going to tell you that I currently make six figures or that I only work four-hour weeks and other such “guru” things.
What is true?
By 2015, I had seven clients that paid me retainers. Three Content Engine packages at $1,800/month each. Two Email Authority packages at $2,400/month each. Two Full-Stack partnerships at $5,000/month each.
That is $20,200 in predictable monthly income before I even accepted any additional project work (which I barely ever did by then) because I didn’t have to.
I worked approximately 35 hours per week and I never went into an office on Fridays.
I was not rich but I wasn’t anxious either.
I knew what was coming in one month. I knew what would be coming in 3 months. I was able to plan vacations without anxiety. I was able to turn away projects that didn’t align with my current strategy and focus on projects that were worthwhile.
My best client has been working with me since 2006 and I’ve been working with him longer than many of my friends.
The quality of the work itself was also much better. I was no longer jumping around from industry to industry and brand to brand and voice to voice.
I had gotten to know my clients very well and I had developed an understanding of their audiences as well as how to make strategic decisions based on my experience within those businesses and seeing patterns develop over time.
This is not some new productivity hack. This is a way to create a business model that acknowledges your humanity.
Your Next Steps
You won’t be able to revolutionize your entire business by tomorrow, you’ll burn out and give up.
Instead, take these steps:
In the next week: Review the last 12 months of client work you have completed. How many were individual projects and how many had repeated engagements as clients? What are some common traits among the clients who returned to you for additional services?
In two weeks: Develop at least one retainer package based on successful work you’ve previously completed. What do your top clients require each month? Create a package to meet those needs.
In three weeks: Contact your three most enjoyable (and ideal) previous clients; the clients you would love to duplicate if possible. Let them know you’re developing a new retainer model and if they’d like to discuss the possibility of being a pilot client for the new program.
In four weeks: If one of the above clients agrees to be involved, ask for payment and deliver quality work. Document all of the work you complete so you may replicate it with other clients.
That’s it. You don’t need a new website, a new course or a rebranding. You just need to develop one retainer client to test whether the model will function.
From there you can build upon what you’ve learned and developed.
The reason why freelancers burn out, but others build sustainable business models is not because of their talent level. It is also not due to good fortune. And while it might seem obvious, it’s not about pricing either.
It is about creating business offers that allow you to build relationships with your clients rather than simply completing individual transactions.
You already know how to do the work. Now create a business model that allows you to continue providing the same quality service without losing your mind in the process.