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How I Turned One Small Freelance Project Into Years of Predictable Income

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There’s nothing more valuable than predictable income when you’re a freelancer. It’s the key to the freedom we all seek. Without consistent income each month, it’s difficult to save money, budget, and buy the things we want.

Unreliable income holds us hostage to our business even if we’ve managed to free ourselves from past employers. It can cause overwhelming stress.

Not surprisingly, it’s also the most difficult aspect of business to control. Even with consistent leads each month, the number of projects you work on can vary. If you accept the same number of projects each month, profits can still vary depending on the size and scope of work.

The result is unreliable income each month, which makes financial planning difficult when our expenses are often very reliable.

So how can you have truly consistent, predictable, and stable income each month?

I want to share my advice in the form of a personal story and show you how predictable income from just one client helped me become a full-time freelancer.

Life before predictable freelance income

I’ve been freelancing on nights and weekends since I started college in 2009. By the time I graduated in 2012, I was earning $2-3k per project and completed a few projects each year.

My projects and profits weren’t very predictable during this time, but that didn’t matter since I was a full-time student and later, a full-time employee. I was just happy to be making extra money and working on a variety of projects.

I loved having my own side business where I made the rules.

Over the next two years, I became the Interactive Art Director at my company, but never stopped doing freelancing projects on the side. Business continued to grow. I earned more money from each project and completed more projects each year.

One small project

In June 2014, I agreed to a two-week redesign project for a startup in New York City. At my then $75/hr rate, the total project would bring in around $3,000 before taxes.

I finished the project on time and delivered the work as expected.  The client was happy with the results and decided to hire me for another small project in early July, just two weeks later.

This new project was worth an additional $5,250.

I finished the work by the end of that summer and casually kept in touch with the client through the holidays. I asked for a testimonial and congratulated them on launching their new website in the new year, which I helped design.

We enjoyed working together and became trusted partners. I was hopeful that there would be even more opportunities in the future.

But in April 2015, nearly a year later, we still hadn’t worked on another project.

Giving up full-time employment

By now my freelancing side-hustle was really taking off, nearly 7 years after it began. I had more consistent leads and regular projects to work on.

I was making excellent money as a freelancer and my freelance income nearly eclipsed my annual salary. That led to me wondering if I could actually freelance full-time because I really enjoyed freelancing.

Rather than “making the leap” into full-time freelancing, I planned to transition from a full-time to a part-time role at my company.

That would allow me to keep my freelancing business growing without taking a big financial risk. The company was small, so I was confident they’d be accommodating rather than give me the boot. As it turns out, I never had to ask.

Accidentally declining $10k/month

That same client finally came back to me in mid-April with a big opportunity — one worth waiting almost a year for. Their company was growing quickly and they wanted to bring their design work in-house.

I was their top pick.

They offered to allocate a much larger budget to my work and cover all travel and lodging accommodations for one week per month so I could work with their team on-site in NYC. I’d work remotely the rest of the month.

The opportunity was enticing, but unrealistic for someone with a full-time job.

I told them I needed time to work out things with my employer and couldn’t commit to a monthly retainer agreement right away.  I declined their offer 3 different times that week as I struggled to navigate this unique situation.

Then I made the mistake of being too honest with my client, who I had become quite friendly with. I had just signed another new project for $18k that same week. It was the biggest project I had ever closed to date.

I couldn’t turn it down, but it dramatically impacted my availability. There was no way I could keep my full-time job, my new freelance project, and commit to a monthly retainer agreement.

In an effort to be honest and transparent, I told my client I had just signed a new project and that my availability had changed. At this point, I was expecting them to give up on me, but I’ll never forget their reply email:


That’s really unfortunate you decided to take on new work after we discussed the opportunity at hand. We were prepared to make you an offer for $10K/mo. Let us know if that changes anything.

Your Client

Gulp. $10k per what?

To put things in perspective, I was earning about $5,400/mo from my full-time job.

It was that night I realized what was going to happen. There wasn’t going to be any part-time employment negotiation — I was going to be a full-time freelancer.

Establishing a retainer agreement

My reply to their email clarified that I was still interested in their offer. In a near-miraculous way, I was already scheduled to be in NYC the next day for a completely unrelated reason. So I offered to visit their NYC headquarters in the evening to discuss the opportunity in person.

That night over a beer in lower Manhattan, I closed a deal with their CEO – my original contact with the company.

I would work remotely as a freelance contractor and be guaranteed $8k/mo for six months working only part-time each week (an effective rate of $100/hr). All travel and lodging expenses would also be covered as I traveled into the office for a few days each month.

That set me up to earn $125k in 2015, nearly double my old salary — and I had predictable income from May to October.

Extending my contract further

Over the next six months, I did my absolute best work and made the most of every trip to NYC. I got to know my clients and their business intimately and added tremendous value to their product through my design solutions. We worked together closely through a highly iterative process.

When October arrived that year, the client offered to extend my contract for another six months. That meant another six months of consistent, reliable, and predictable income. Six months later? A third contract renewal. A few months after that? A bonus equity agreement that gave me a small percentage of the company.

By now I had gone from designing their marketing website to completely overhauling their core product, becoming their most valued front-end developer, and owning part of the company. I was asked to design every user-facing aspect of their business right down to the business cards.

Meanwhile, I dedicated my other 20hrs/wk to some really exciting short-term projects that set me up to earn $150k in 2016.

By now, my website was bringing in so many organic leads each month that I never had to worry about finding more clients.

All good things come to an end

In 2017, the company underwent a “restructuring” of sorts and there was no longer a need for my work. Thankfully, I had lined up another long-term retainer agreement with a new client, but I kept in touch with my friends at the NYC startup as I had done in the past.

A whole year went by and there was no need for a new project. There was no more work to do. The future of the company was being determined behind closed doors and all design efforts were put on hold.

I continued working through 2017 with a variety of clients on a few great projects, including one retainer arrangement that also got renewed three separate times.

But there was still no word from my partners in NYC. I wondered if there would ever be a need for us to work together again or what would become of my equity, but I also knew that startup culture was sometimes unpredictable.

Starting up the startup (again)

In December 2017, I got a very exciting email. The company had successfully restructured and was on the up and up. They wanted to establish a new monthly retainer agreement for a minimum of three months starting in January 2018.

My schedule was clear after the holidays so I signed on to completely redesign their entire platform from the ground up, for the second time.

In total, this single client paid me over $200,000 all because of a small $3,000 project I agreed to do on nights and weekends.

Being a calculated decision-maker, I wouldn’t have transitioned into full-time freelancing at the time if it weren’t for this opportunity. It gave me just enough financial predictability to feel comfortable leaving full-time employment behind.

How does this help you?

I want you to grasp the value of long-term retainer arrangements and their impact on your freelance income. If you can get just one client to pay for 5, 10, 15, or 20 hours a week for a few months at a time, you’ll instantly stabilize your income.

If you don’t like hourly billing, charge by the week or even the month for specific deliverables when the project is well-defined.

Remember, the main goal is just to make your income more predictable. You can always change your billing strategy once you’ve established a solid foundation in your freelancing career.

Here are a few bits of advice I hope you can take away from this story:

  • Unpredictable income results in an unpredictable lifestyle.
  • Carefully evaluate every opportunity. The same client may need you for more than one project.
  • Ask about future opportunities with clients you enjoy working with.
  • Always deliver your best work on time and earn your reputation with each client.
  • Retainer agreements often get renewed or extended following hard work and good communication.
  • Always keep in touch with past clients. Ask for testimonials, ask about their business, and just say hello every few months.
  • Don’t make the mistake of “oversharing” information or over-explaining your circumstances. Clients don’t need to know everything.
  • Freelancing on nights and weekends is a great way to find out if freelancing is right for you.
  • Transitioning away from your full-time job isn’t always easy, but you’ll probably know when the time is right. Trust your instincts and don’t act rashly.

Predictable income in practice

Retainer agreements are simple. Instead of billing hourly, you agree to a fixed weekly or monthly rate and get paid at the corresponding interval. You can even use an hourly rate to determine your weekly or monthly rate.

This is a great way to charge clients who have a large, loosely defined scope of work. Maybe they have the next few weeks planned out, but beyond that, they haven’t confirmed or finalized their next steps.

You’re probably already familiar with hourly or even weekly billing. You don’t have to change that to offer a monthly retainer to these types of clients.

For example, if you think a project could take 6-8 weeks, but don’t have enough information to know for sure, simply offer a weekly or monthly retainer agreement. That leaves the scope of work and total project cost flexible for you and the client as the project unfolds.

Don’t forget to sign a contract or charge upfront for each week or month to ensure you get paid.

Maximize your existing client relationships

What I love most about long-term partnerships, retainer agreements, and return business is that it doesn’t require anything other than hard work and good communication with clients you already have. You don’t need an amazing website and you don’t need to rank at the top of Google.

You don’t even need a good sales pitch or a proposal because presumably, your clients already like working with you.

All you need to do is look for ways to provide value to your existing clients on an ongoing basis and offer it to them. Doing so will completely transform your freelance business.

When you have predictable income, you’ll have a predictable lifestyle.

Last updated on June 25th, 2023

About Matt Olpinski
I've been freelancing since 2009 and have worked with over 100+ clients including some of the biggest brands in the world. I later started my own company Matthew’s Design Co. and now teaches 50,000+ freelancers each year how to succeed through his personal blog, newsletter, and community for freelancers.