16 Pro Freelancers Reveal How They Stay Booked for Months into the Future

For anyone who depends on clients to keep their business going, the feast-famine struggle is all too real. This classic (almost cliché) problem facing freelancers from all industries can cause major cash flow problems.

Of course, if you’ve been freelancing for long, I don’t have to rub that painful truth in your face. You’ve probably seen it all around you.

Some freelancers seem to rake in big money while others struggle month-to-month to find any consistency.

Some freelancers seem to always have more clients than they know what to do with, while others keep trying new tactics to get clients—and nothing ever seems to stick.

If you’re ready to pad your schedule (and your bank account) with more clients, booked out farther in advance, then it’s time to take action on the advice you’ll find in this article.

I’ve compiled what has quickly grown to be a small masterclass on the art of booking clients out for months in advance.

The advice comes from 16 friends of mine; fellow freelancers who have figured it out. Freelancers and entrepreneurs who know what it takes to get new clients, keep them coming back, and book out their schedules (and their revenue) for months into the future.

Advice from 16 freelancers who have figured it out

For starters, my friend Jake built his company Lead Cookie to $45,000/mo. in less than a year. It’s safe to say he knows a thing or two about getting (and keeping) clients. 

For Jake, it’s all about consistency.

Build consistency with marketing habits

Spend at least 30-60 minutes per day doing something to market yourself,” Jake told me. 

“The ‘what’ matters less than the habit of working on your marketing every single day. Make marketing yourself a priority and do it every day. If you do that, your client pool will never run dry.” 

Now, Jake’s on to building his second company, a content marketing agency, using the same guiding principles. 

Finding consistency is key for freelance designer Jill Anderson too.

My #1 tip for booking clients months in advance is consistent content marketing,” she recently explained to me. 

“I try to publish at least 2 blog posts a month. Then I send out a newsletter with a quick intro and links to my posts. My newsletter keeps me in touch with clients and prospects. And the consistent blogging keeps me in Google’s good graces.”

Want to learn more about using email for content marketing? Get our Ultimate Guide to Email Marketing here.

Freelancer Rob Palmer put it this way:

“The best way to keep your schedule full is to always be marketing. The big mistake most freelancers make is to stop marketing when they get a big project. Then when that project finishes, they have nothing in their diary.”

Jake, Jill and Rob aren’t the only ones who recommend focusing on better business habits

Talented financial planning freelancer Pamela of Brunch and Budget told me the same thing:

Set up and systematize regular business habits that you do no matter how many clients you have,” Pamela advises. 

“That could be anything from going to networking events 1x/week, posting on social media regularly, sending out a regular newsletter, etc.”

Turn business habits into client-getting systems

In many of my conversations with these experts, this idea of using habits and systems to book clients came up over and over again.

I knew I personally had seen how leveraging systems can transform your business and was pleased to see it was a common theme.

Rob Allen is a freelance copywriter who has grown his services into a full-fledged copywriting agency.

I met Rob when he challenged himself to book $5,000 worth of freelance writing clients within 30 days as a brand-new writer.

Not only did he crush that goal, but he also booked himself out with client work for 6+ months. 

Not bad.

Rob used a combination of well-crafted systems and high-value offerings to grow his business.

“When I first started freelancing, I found myself susceptible to HUGE swings in income,” Rob recently shared with me. 

“The only way I could break the cycle was to turn my freelancing … into a well-oiled machine. 

“For my agency, that’s meant dialing in our offering, customizing our pitch, automating our follow up, perfecting our client onboarding and offboarding so that every client we come into contact with turns into a predictable amount of revenue and referrals.”

With systems in place, Rob finally found the predictability that seems to elude so many freelancers.

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Automate your marketing efforts

Who wouldn’t want to have a freelance business where new clients seek you out as if by magic every month?

I know I would.

That’s why I’ve been fascinated as I’ve made friends with a few freelancers who do just that: they use their portfolio website as a constant source of new clients.

It happens almost on autopilot.

Logo designer Ian Paget gets more inquiries than he can take on in any given month and finally took his freelancing full-time just recently.

“In order to stand a chance of being booked months in advance, you need a steady flow of leads coming in,” he advocates. 

“My primary source of leads is Google. When people need a logo, they search for ‘logo design’ or ‘logo designer’ and thankfully I’m lucky enough to be in the top results [in the UK].”

“So whilst it’s a long term strategy, put as much time and energy as you can into learning and working on Search Engine Optimization so your website turns into a lead-generating machine.”

Ian’s not the only one pulling this off. I have been amazed to watch my friend Matt Olpinski do the same thing with his website.

“My website is 100% responsible for keeping my project calendar booked months in advance. 

“Every decision about content and design is focused on getting more clients to find and contact me. 

“Over time, that strategic effort has put me on the first page of Google and I’m frequently turning down work for lack of availability.”

Identify and focus on the right kinds of clients

Of course, building all the systems in the world and bringing in leads on autopilot won’t help you unless you’re attracting the right kinds of clients

Freelance designer Brent Galloway has become a go-to t-shirt designer for some of the biggest names in music. 

He agrees that dialing in your “ideal client” is the best option.

“My secret to keeping a booked schedule has been finding clients who are in constant need of designs. 

“How did I find these dream clients who are sending me new projects every week? 

“First, I defined what type of work I wanted to be known for and who I wanted to work with. After years of trying everything I discovered my obsession for designing t-shirts. So I built my entire brand and portfolio around it. Because I only show and share merch designs, that’s the work I attract. This also gave me clarity on who I should be connecting with: clients who would be in regular need of merch designs. 

“I got my foot in the door of the industry by sending cold-emails introducing myself. Having a focused portfolio of merch designs helped lead to more replies. One project led to another and sharing completed projects helped me attract new clients. 

“I’m grateful and proud to now be in a position where I’ve worked with a handful of the same clients for over three years. And my client pool only continues to grow.”

Mania Mavridou follows this same philosophy:

“Stand out and become an expert to attract your ideal clients. My secret to being booked in advance is to be sought-after, have systems in place and attract your ideal target group.”

Stay hyper-aware of current and future opportunities

Two freelancers I spoke with reinforced how important it is to stay aware of your current and future situation.

Because a freelancer can wear so many different hats, it takes real talent and effort to avoid getting distracted for days at a time (I know I’m guilty of this) and letting your promotion and sales efforts run dry.

Patricia Lacroix says, “I keep my business at the forefront of my own mind, constantly. That way, I never miss an opportunity to bring up my business and how I might solve a person’s problem. You have to not be afraid to seize that opportunity when it does happen.”

Designer Ben Brush concurs with Patricia’s theory: 

“Keep a meticulous calendar of your work. By doing this you are aware of holes in the schedule before you’re in them. Knowing your availability down to the hour lets you maximize booking and stops you from turning down work you need later, just because you feel busy now.”

Focus on recurring revenue & repeat business

Of course, simply booking more clients isn’t the only way to guarantee you’ll have income for months to come.

Many freelancers who grow tired of finding new clients every month in a never-ending sales cycle decide to lean into a recurring model instead.

Leverage the power of retainers

I’ve watched my friend Chelsea Baldwin do this exceptionally well.

“My favorite way to keep a full client pool,” she has told me,  “is to sign people onto smaller retainers once I finish a big project for them. 

“For example, if I created a full email marketing funnel for a client, I’ll offer them an add-on retainer at the end of the project to keep an eye on the funnel’s data. I’ll implement changes for improvements where necessary. 

“These retainers usually cost less than the initial project, but they provide on-going value & they’re easy for a client to say yes to. 

“Once you get a handful of these on-going retainers in place, you don’t have to worry about the feast-or-famine cycle anymore, because you have a baseline of income you can rely on each month.

Jorden Makelle has a similar approach in her business. 

Her advice is to ”focus on landing ongoing retainer clients who can actually afford to pay well! You can package your services … and have the client sign a retainer contract. This way, you feel secure knowing you’ve got cash coming in every month!”

Focus on over-delivering for your clients

While it may prove successful for you (as it has for Chelsea and Jorden) you don’t have to pitch a retainer agreement to your clients in order to have repeat business every month.

My good friend Andy Conlin focuses on giving his clients the best experience possible—and attributes this effort to his growing business.

“Do the kind of work—and be the kind of freelancer—that people will keep coming back for. Skilled, thorough, and excited about what you do. Once people see what you’re capable of, they’ll be happy to return or refer others to you. Be proactive in finding additional ways you can help them. These are strategies that have served me well.”

He’s not alone in this long-term, genuine business strategy either.

Rebecca Blaesing advises, “Treat every client with respect, and be very responsive and clear in communication. At the end of every project, I want my clients to feel like I am truly invested in working with them. Happy clients return, and they become walking testimonials for me.”

Consultant Rhonda Page feels the same way. For her, client loyalty is critical to a freelancer’s success.

“Become a strategic partner to your clients. It’s harder than ever to stand out and get client loyalty. Keep clients keep coming back again and again by understanding more about their business and caring as much about it as if it was your own.”

The one tactic we’d all agree on

Learning from these expert freelancers and entrepreneurs was motivating and inspiring for me—and I hope it was for you too. 

I don’t have to reach back out to all of my friends who shared their advice in this article to know one thing. 

There’s one tactic each and every one of them (and I) would say is crucial in your journey to becoming a sustainable freelancer:

Take action.

Reading today’s article might have inspired you. It may have pumped you up to make big progress in your freelance business this year. Maybe it gave you hope that you can one day quit that job you hate and finally do work you love.

But, I guarantee that will never happen if you don’t take action.

So, right now, before you close this browser window and go back to your usual routine, leave a comment below and tell me what action you’re going to take in the next week to move your freelance business forward.

I’m holding you accountable. Trust me, you’ll thank me later. Good luck!

Preston Lee

Preston Lee is the founder of Millo where, for over a decade, he and his team have been helping people escape their desk jobs by starting a blog, becoming a freelancer or building a side-hustle.

8 comments

  1. Right now I own a sole proprietorship part-time Fine Art business. I also work as an elementary art teacher but would like to move out of that and into making art full time. I have a solid client base with repeat customers. But I don’t market much bc I feel overwhelmed working full time and doing custom artwork on the side. I have a website but my forms are broken bc I don’t have my connection with MailChimp anymore and haven’t been blogging. Though I’m still informed that I get a form submission almost everyday. That’s another potential client every day. I feel like I’m in limbo. But my goal for this week is to fix my form submissions and start blogging so I actually have something to automate in a reply. I blame it on lack of time but really I could make the time to do it. So why don’t I?

    Reply
    1. Sobrina Pies

      you can do it, Tiffany! we believe in you!

      Reply
    2. Preston Lee

      Hey, Tiffany. Thank you for sharing your story with us and double-thanks for the vulnerability in your question. That’s not easy! 🙂 Speaking as someone who ran a side-business for YEARS before I finally went full-time, I feel your pain 100%.

      I wish I had really helpful advice for you, but I was too chicken to take the leap until I was forced into it myself (got laid off). But I will say: I wish I had done it so much sooner. It wasn’t nearly as scary as I thought it was going to be. It’s actually been one of the best things that ever happened to me.

      Here are a few pieces of advice that are a bit more tactical in nature:
      1. Make sure you have a financial cushion since the time between going full-time and making a full-time income may differ by as much as 6-12 months.
      2. Remember that if you were employable once, you’re employable again and the worst-case-scenario is you’ll just need to get another job.
      3. If you can swing it, outsource the stuff that brings you anxiety (the marketing or the site development) (I recommend https://handywp.com for blogging help)
      4. Really investigate whatever your biggest fears are. If I had looked into health insurance or my own financial runway/cushion in as much detail as I did when I was let go, I would have gone FT years ago.

      I agree with Sobrina! You can DO THIS! It’ll change your life. I sincerely wish you luck. And if you’d like to chat more or get more support, i hang out with 6,000+ other creatives here and we’d love to have you join us.

      Good luck!

      Reply
  2. I advert my business every day 3 times a day on 7 different social media. And post on them business content.

    Reply
    1. Preston Lee

      Sounds promising! How’s the working for you? Do you find it brings in a lot of business?

      Reply
  3. Thanks for this post!

    I will consistently invest time on marketing my business from now.

    Reply
    1. Preston Lee

      Glad to hear that! I hope it goes well for you. 😀

      Reply

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