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Smoothing out the freelance rollercoaster

How to schedule projects, manage an even workload, and make consistent income from freelancing.

Is your freelance career a constant rollercoaster of ups and downs in work and income? Does the feast or famine cycle stress you out so much you consider running back to the certainty of a boring 9–5?

It doesn’t have to be that way. My freelance design business hasn’t been a rollercoaster for many years — in fact it feels more secure than being an employee — and I’d like to share why.

There are many aspects that contribute to a successful freelance schedule. I will discuss:

  1. How to obtain new clients and book their projects well in advance so you have certainty in your schedule.
  2. How many projects you should work on at once, and how to divide your attention between them to create an optimal, balanced workload each week.
  3. How to anticipate delays, manage feedback cycles, and motivate your clients to keep project momentum going.
  4. How to build a freelance business that offers more long-term security than you may have from full-time employment.

Attracting new clients

I’ve written extensively on this already, discussing what are the best kinds of clients, how to land your dream clients, how to talk to potential clients, and how building a strong reputation helped me earn $15,000 a month from freelance design.

Are you working for cost-clients or value-clients?

Knowing the difference will mean everything to your freelance business.

Every independent contractor will have their own favourite ways to advertise themselves and attract new clients. My favourite way it to do as little marketing as possible. As silly as it sounds, that’s a very realistic goal and valid strategy for gaining freelance work. Let me explain.

The best freelance clients are ones who trust your skills and and respect your experience. The easiest way to gain that trust is to get clients who have been referred to you by someone they already trust – a friend, family member, colleague, or other professional acquaintance. The best way to encourage those word-of-mouth referrals is to exceed your clients’ expectations, act ultra-professionally, and consistently delivery quality work. This will build a great reputation, as well as a network of people who promote you for free.

Once you get there, you’ll find you don’t need to do any advertising. You don’t need to slave away producing social media imagery or blog posts to broadcast your accomplishments to the world. If you keep putting in the hard work to build upon that reputation and network of satisfied clients, you can be incredibly successful by doing little else but the hands-on work you love most.

The right way to start freelancing

No gigs sites, no free work, no drowning, no shit!

Booking & Scheduling

My services are in high demand, and as such I generally have to book projects months in advance — because that’s how long it is until my next gap of availability. Good clients are usually willing to wait, because they know working with the right person is the most important factor for a project’s success.

But of course there are times when there are unchangeable reasons for a close deadline, and my lack of short-term availability is a deal-breaker. I have to turn down potential clients and projects (even from loyal repeat-clients!) all the time because of my lack of availability. That’s the cost of being in high-demand.

The upside is that I generally have multiple potential projects to choose from. Scheduling the right ones at the right times can be a real challenge. When you have to book months in advance, it requires starting the conversation with clients very early and gathering all the info necessary to determine scope and project length in time to reserve a spot for them. It requires well organised clients who are capable of having these discussion and making decision, even when some details may be fuzzy because you’re still a month or two out from starting in earnest.

There are a few things that help me schedule accurately and keep my freelance plate full of juicy new projects all the time:

  1. I use Cushion to create a visual timeline of my projects and workloads to help me gage when I have gaps in my schedule, and how much of my time/attention is available.
  2. I often sign up clients on a weekly retainer (with a guaranteed number of hours per week). This helps me manage my workloads and ensures I have enough time to devote to each project I take on. I hate being over-booked more than not having enough work, because I dread the thought of being pinched for time and having to produce sub-par work.
  3. One huge upside of having a retainer — with a pre-defined range of weekly hours — is that you have a clear indication of your exact future earnings during that contract period. It creates both certainty of schedule as well as income.
  4. As best as I can (with the client’s help, or informed by their budget), I determine how many weeks a project should take and update my availability calendar accordingly. I create opportunities to review and adjust this schedule as milestones are met further along the project. I usually pad each project with an extra week just in case.
  5. I require a deposit payment in order to confirm a new project and lock-in time for it in my schedule.
  6. I’m very open and transparent about my schedule and workload with current and potential clients. They know how much time each week I can devote to their project, and exactly when and for how long I am available.

Blocking out weekly workloads

My optimal scenario is to split my time and attention between two big projects at once. I find this creates the perfect balance between project speed and momentum, and also allowing time for client review/feedback. I tend to share my time each week equally between the two projects.

Once I’ve removed all the admin and extraneous communication from my daily schedule, I’m left with roughly 6 billable working hour per day = 30 hours per week. I promise both of my active large projects 10–15 hours per week. I’m very upfront about this, and why. I use Cushion for this too, so I can manage and visually track my expected workload for each project and judge how many hours per day I may have available, or pinpoint where I may have over-booked my time.

I often have a third smaller, more casual gap-filler project on the go, which I use to fill cracks if both my other projects are slow.

I’m most productive when I work in 2–3 hour focused bursts, which fits perfectly with this 50/50 division of time between two projects. I will spend the morning on one project and then the afternoon on another. I prefer this type of deep focus over jumping around between smaller tasks.

If I do have smaller tasks to take care of, I like to get through them first so my mind if more empty to focus on the big stuff. I keep a simple task list updated every day to remind me what my priorities are each day and week.

If you charge by the hour, there’s an obvious advantage to finessing your work processes to get the most efficiency out of your day: the more focused, billable hours you can fit in, the more you earn. Even if you price differently (such as value pricing) it’s still to your advantage to be as productive as possible, so you can get the same amount of work done more quickly — boosting your “profit” for the project.

What to charge: does value-based pricing live up to the hype?

Demystifying pricing techniques + value pricing implementation tips

Managing feedback cycles and project momentum

One thing that can be a challenging part of any design process is managing the client feedback schedule.

I like to work really closely with my client and involve them intimately with the design process, so I tend to work in small bursts of one day or two and then ask for frequent feedback. This ensures the design is on-track at every step, increasing efficiency and reducing the chance of repeated revisions and having to re-do work when UX decisions change course.

The perfect marriage of designer & client

Your client isn’t the boss, and neither are you. It’s a symbiotic partnership that leads to the most successful projects. But does your client know their role?

Working tirelessly on a super complete hi-fi design and then doing the “big reveal” client presentation may have its place for some clients — who expect and require it in order to accurately judge a visual product — but it doesn’t jive with my iterative and open design process.

I also write into each of my client agreements that design feedback is expected within 24 hours in order to maintain project momentum. Setting this client expectation is extremely important! If you don’t have this discussion right at the beginning of each project, your client may assume that one week is a perfectly acceptable timeframe for gathering feedback. Meanwhile you’re twiddling your thumbs for days waiting on their input, and scratching to come up with other work to fill the void.

Having a retainer agreement helps in this regard. If both you and your client understand that quick feedback cycles are a necessity to ensure their weekly target hours are met, they’ll be well motivated to stick to that schedule, or else risk the chance of paying for retained hours you were unable to use while awaiting delayed feedback.

If there is a period during the project where extra review time is necessary — for example the project lead needs to share designs with a wider group of stakeholders for approval — it’s important to be informed of this well in advance to you can schedule your time for that week accordingly, and boost time spent on other projects to compensate.

Building a secure freelance business

When you’ve built up enough good reputation and satisfied clients to have a steady stream of new clients each month, you’ve spread your risk way out. If you lose one client, no bid deal, you’ve got others, and you can get more. Unless you’ve made the mistake of putting too many eggs into one basket, as I once did.

I fell off a freelance cliff, but built a parachute before I hit the ground.

Or, the danger of having too many eggs in one basket, and how to bounce back when that basket disappears.

In many ways, a thriving freelance business is far more secure than traditional employment. I never have to worry that my boss might fire me on a whim, because I am my own boss. If I have to part ways with a client-partner, it’s a small recoverable business injury, not career death on the line. Being in charge of your own business destiny is always going to be more secure than working hard to advance someone else’s — so long as you can trust yourself to look after your own business development.

Hand-in-hand with that control and security is the opportunity for boundless increases in earning potential. If I feel the need to make more money, I don’t have to make the right time to ask my boss for a raise (and reasons to justify it). I simply experiment with raising my rates, try out new pricing techniques, or learn how to use my time more efficiently. I’m only limited by what my market is willing to pay, and I regularly exercise the freedom to turn down projects that don’t meet my budget expectations.

As a freelancer designer, the kinds of clients and projects I choose — and the way I go about managing their schedules, workloads, and iteration cycles — has an enormous direct impact on my happiness, work fulfilment, career security, and earning potential. But none of that happens by itself. There’s nobody else doing this for me.

Freelance business owners need to setup consistent processes that lay the foundation for efficient scheduling and successful projects. If you don’t, you keep riding that endless rollercoaster and wondering why it’s so difficult to keep things consistent. A little effort and attention to your client acquisition and project management processes will turn that unpredictable thrill ride into a smooth cresting wave you can surf all the way through the endless-summer of your successful freelance career.

The feast or famine cycle is not a painful necessity of the freelance lifestyle if you choose to mitigate it. A full-time, high-earning, and creatively satisfying freelance career is easily obtainable if you know how to plan carefully to overcome these common freelance hurdles and stereotypical independent contractor challenges.

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Benek Lisefski

Hi, I'm Benek Lisefski. Since 2001 I've run my own independent design business. Join me as I unfold 20 years of freelance business knowledge: honest advice and practical tips to help you take your indie career from good to great.

MediumTop writer in Design, Business, Creativity, and Entrepreneurship.