How To Delegate When You’re Creative

A few years back my wife and I decided to take a short vacation to Costa Rica.  We had a great time for those few days we spent unplugged from computers, relaxing on the beach and ziplining through the rain forest.

But in order to pay for that trip, I had to take on a few extra client projects the month before we left.  That meant working late nights and a few weekends.  Plus, we couldn’t stay on vacation longer than 4 nights because I couldn’t afford to take more than one week off from client projects.

The day we came home, I checked my inbox to find it flooded with emails from clients, fires to put out, and tasks that needed my immediate attention.  Within hours of landing back at home, I was right back in the grind.  Back to trading hours for dollars.

Sound familiar?  Most of the freelancers I speak to tell me that’s their biggest challenge right now:  That their income is tied too closely to their time.  And when I ask where they’d like to be 12 months from now?  Most say they want to break free of billable hours and build something more scalable.

Working as a Creative

So how do you get there?  How can you transition from working by the hour or by the project, to running a business that pays your salary, regardless of whether you’re at work or taking a day off?

At first, this was a strange concept to wrap my head around.  Up until a certain point, I had always considered myself to be a creative professional.  I was a designer and developer by trade.  Back then, I never thought of myself as a “Business Owner”.  I knew how to write a proposal and send an invoice, but that was about the extent of my business skills.

Most designers, coders, copywriters, and other creative professionals are in the same boat.  You know your craft inside and out, and you know how to manage a few clients, but building and growing a business?  That’s new…

Struggling to Delegate

The first hurdle that was really tough for me to overcome, and the one that I see lots of freelancers struggling with is the ability to delegate.

If you’re ever going to grow your business so that it can keep producing without you, you’ll need to be able to delegate.  But handing off those first few tasks to someone else is always a lot harder than it seems.

Here’s what typically happens:

You decide it’s time to start outsourcing parts of a project, or bring on an assistant to help with the day-to-day operations.  You’re excited, because you’re finally going to get some of your time back to focus on other things…

So you ask your new teammate to complete a task for you.  You give them some basic instructions and off they go.  A few days later, you check in on their progress.  Did it get done?  Not quite… They missed a few things and the overall quality was sub-par.

Rather than asking them to fix it, you decide to finish it yourself, which actually means re-do it yourself.  Now you’ve just spent twice as much time, and paid twice for the same thing to get done.  But you learned your lesson, right?  Next time, you’ll need to give better instructions and hire someone more capable.

So next time comes.  You try delegating again.  This time, you start to write out instructions and search for the right person for the job.  But then you stop and say, “Ya know what?  It would be much faster if I just did the damn thing myself.”

And now you’re back to square one.  Doing all of the work yourself with a business that runs entirely on your own time.

Your Transformation

In order to truly break this cycle, you’ll need to go through somewhat of a transformation.  You’ll need to begin thinking of yourself as a “Business Owner”.

And believe me, I know how daunting this may sound.  You’re used to working in Photoshop, or in code or writing and creating.  You never went to business school.  You never set out to become a manager.  Or a sales person.  Or a marketer.  Or any of the other things that tend to get lumped in with being a “Business Owner”.

That’s OK!

In fact, you don’t need to worry about all those things.  You simply need to make a small shift in your mindset and the rest will fall into place.  That shift is this:

You need to work less “in” your business and more “on” your business.

Up until now, you’ve probably spent most of your time “in” your business, doing all of the tasks yourself, servicing clients one by one and invoicing for your time.  That’s worked out OK for a while, but now you’re ready to level up.

As a Business Owner, you need to work “on” your business.  And as your first order of business, your task is to figure out how to make your business run without relying entirely on your own time.

The Path to Autopilot

Now, as you may have learned the hard way already, it’s not quite as simple as the “gurus” will have you think.  If only it truly was as easy as hopping onto oDesk, making a hire, and asking them to take over.  What I found, and what most freelancers find is that rushing into it like this is a recipe for wasting time and money.

I want you to take a more strategic approach, by laying the groundwork way ahead of the time you begin to delegate.

Here is my 5-step path to getting there:


The first step is to standardize the work so that it becomes as predictable as possible. This means developing repeatable processes, and making important decisions about what exactly you offer, how you deliver your service, which tools you use, and which things you choose not to do.  Standardizing is one of the core ideas in building a Productized Service.


As the work becomes more predictable, you can find ways to streamline it. This could involve setting new limitations, incorporating software, or developing working frameworks and templates to leverage your (and your team’s) time more efficiently.


Before you can fill key roles on your team, your processes must be documented in standard operating procedures (SOP’s) . These make up the operating manual for your business. The goal here is to get all of the know-how out of your own head and documented so that your teammates can benefit and be successful.

Hire & Delegate

With your standard, repeatable processes hashed out, you’ll be ready to begin the ongoing process of filling key roles and delegating responsibility for carrying out your service. Systematically over time, you can remove and replace yourself, freeing you up to focus on pushing the business forward on a higher level.

Refine, Improve & Iterate

Nothing is set in stone. From day one, through year one, and beyond, you’ll need to constantly refine and improve every aspect of your business. From the things your service offers, to the ways in which it is streamlined, through to the procedures and documents that define how things get done.  Everything gets better over time.

Working For Freedom

All of this sounds like a lot of work, doesn’t it?  Well you’re right.  It is a lot of work.  It takes months and years to get all of these steps dialed in.  Is it really worth it?

Well, think of it this way.  When you’re working project-to-project, you’re working for your hourly rate.  Do the work once, get paid for it once.

But when you’re working “on” your business, you’re working for much more than your hourly rate.  You’re creating systems that will make your business run without you.  You’re working for freedom.

For some, that could mean freedom to go deeper into your core craft, while you delegate everything else.  Or it could mean freedom from all day-to-day tasks so that you can focus on the bigger picture.  Either way, by putting in this time “on” your business, you’re learning what it means to take ownership of your business, and your time.

  • There’s one other trick: Letting go of ego. You think that only you can create the perfect web page or blog post or whatever, but it turns out that lots of others can. Once you embrace that, you’ll be happier.

    The customers of my company, BlogMutt, certainly have found that to be the case, and they tell me how much happier they are once they realize that the blogs don’t have to be perfect for them because they are not the audience. Someone else can write the blogs and may even do a better job.

    • Great point Scott. It’s really difficult to get past that when you’re the one who has always created all your work. But as you said, there are plenty of talented folks who are ready to work with you. It’s also important to embrace that others will have their own style and approach, and to let them go with that if it makes the experience better for your customers.

      *Brian Casel*

  • Hi Brian,

    Love this! You’re working for freedom. That is so true. It is quite difficult for people to let go of the reins of their work because let’s face it, their business is their BABY. Who else is going to take care of it better than them. However when you’re juggling a million tasks in one day… where’s the joy and freedom?

    When do you have time for yourself and enjoy family. That’s the reality that will hit when you realize that you need help fast. You never want to get to THAT point. Know that you’re a business owner and understand that delegating is most beneficial for your well-being. Lots of work upfront but it pays at the end.

    Thanks for this post!

    • Couldn’t agree more Lillian. Spending time with my family, especially since my daughter arrived earlier this year has basically FORCED me to be much quicker to delegate tasks and place even more trust in my team (and they deliver 110% every time).

  • Liv

    This is a GREAT article! I was just feeling the trade off and feeling like I’d have to do that for forever felt way to daunting! thank you for this perspective!!! Truly helpful!

  • Vikki Fraser

    Excellent article. I would add to the Standardization portion by including “naming conventions” for file names and folders. Makes life so much easier when someone else takes over, and the one after that and so on. I also found that mixing in residual income (web host reselling) into my design and code business got me to the point where I could take a little time off and not panic that bills wouldn’t be paid. A guaranteed amount every month affords you peace of mind.

    • Thanks Vikki! Great point… We use Google Drive to manage all of our procedures, and all of them are based on a template Procedure, which sets the format and conventions to keep everything consistent. Super helpful.

      And yes – nothing beats recurring revenue so you don’t have to start every month from zero 🙂

  • Noell

    Hey I really love this article. I’m a nationally recognized personal trainer and was recently on the cover of women’s health magazine. Since the cover, my training business has boomed, I’m getting requests from big companies to do research and I’m getting hired to represent atheletic companies too. This all sounds great and it is! But it’s been a messy few months and I’m gathering all the business wisdom I can find right now. I need to delegate for sure bc I can only work so many hours per day! Thank you for the suggestions. They’re practical and they’re motivating me to make some changes I need to make soon!

    • That’s awesome Noelle! Glad you found this helpful. Thanks!

  • SO true … ! I thought you were in my head with this one.

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  • Sergey Yatsenko

    Your Transformation. –
    Philosopher Kings: Business Leaders would benefit from studying great writers. – */S.Y Looking for answers with new Mindset after Transformation.

  • Solomon Kleinsmith

    Mother. Of. Gawd… the few short paragraphs after the “Here’s what typically happens:” is EXACTLY my experience, with a few exceptions in cases where I have really REALLY broken the needed work down into relatively straightforward pieces, or had put together insanely detailed instructions.

    • Ha you too? Thanks for reading.

      • Solomon Kleinsmith

        Me too indeed – eerily similar.

        Thanks for putting this material together. I heard about you from your “class” on Mixergy. I’d never heard of this term “productization” before, but it’s what I’ve been slowly (and really, fairly poorly and haphazardly) doing over the last few months, trying to figure out how to expand. Currently heeding advice from someone else on the Mixergy site about breaking processes down into cards on Trello.

        Planning on trying to make time for your paid course next month. Thanks for doing this for people in this position. Hopefully that term gets more widespread and people are able to find information on it more easily.

        • Awesome, the Mixergy course was fun. Thanks for tuning in!

  • Thomas Fabro Barreira

    Great, that will help a lot!!!

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