“A professional distances herself from her instrument. The pro stands at one remove from her instrument—meaning her person, her body, her voice, her talent; the physical, mental, emotional, and psychological being she uses in her work. She does not identify with this instrument. It is simply what God gave her, what she has to work with. She assesses it coolly, impersonally, objectively. The professional identifies with her consciousness and will manipulate it to serve her art. Does Madonna walk around the house in cone bras and come-fuck-me bustiers? She’s too busy planning D-Day. Madonna does not identify with “Madonna.” Madonna employs “Madonna.”

Steven Pressfield1

The Work

The work is what you do for your clients and yourself. It is the outcome of your effort, the fruits of your labor, and the tangible result of intangible thoughts and ideas. Your work, however, is not you. As creatives, we tend to merge our personal identity into our work and take our entire lives into the hole with us. The grind of running and growing the business can become so involved that you ultimately lose sight of the work and it becomes this dark cloud that sits above you 24/7.

You can go too far into the business mindset so that, sometimes, the business side of creativity becomes so engrossing that you stop doing creative work altogether. For some, that’s a natural progression. For others, they can’t imagine letting go of actually creating and doing the work. For me, that was never an option. I love to create more than anything. I don’t ever want a business that is so involved that I can’t actually work with clients any more.

As you mature in your business, you’ll have to find ways to ensure that you have the time and energy to get the work done. Otherwise, the growing demands of your business will take it all away from you, and you’ll be far less involved in the work. In Chapter 9 we’ll dive deeper into growth and what you can do to find your ideal size and situation, but that process takes time. The realities of running a creative business colliding with growing a creative business are in front of you right now; growth isn’t happening overnight. We’re going to focus on running your creative business while still doing work that you enjoy.

Here’s what we’ll cover:

  • Deadlines
  • Just ship it
  • Impostor Syndrome
  • Procrastination
  • Scheduling and time management
  • Delegation
  • Side projects
  • Staying inspired

Deadlines—Just Ship It

Deadlines

I remember a particular week in 2009 when I had seven deadlines in four days. That may not sound too bad, but let me tell you how much work was left: forty-six hours. And that was my estimate. As Paul Wilson says, “things take twice as long, cost twice as much, and bring half the rewards that you anticipate.”2 So in reality, I was looking at ninety-two hours’ worth of work. You may ask yourself, how did I get here? How did I end up with such a ridiculous amount of work due at the same time? This is not my beautiful house … anyway.

Well, the whole truth is that three of the seven deadlines had already been shifted to that week because I had missed them in weeks prior. One of the other deadlines was moved up a week because I needed to spend the following week on site with a client in planning meetings. None of these projects were last minute. In fact, most of them had been weeks or months in the making. I was the problem. I had spent excessive amounts of time on research, sketching, planning, and who knows what else. I had procrastinated and delayed getting any designs done because nothing “felt right.” Needless to say, I was screwed.

“Work expands so as to fill the time available for its completion.”

Parkinson’s Law

I made four of the deadlines and finished two of them on Saturday and Sunday. I worked no less than fifteen hours each day and slept no more than four hours any night that week. I mostly fell asleep on the couch downstairs. The three deadlines I missed were all for existing clients, no one new, and I was able to talk my way out of any repercussions. But, I still had the planning meetings the following week. So now I had to work ten-hour days with one client and then go home to work all night catching up on the three remaining deadlines. I slept four hours a night that following week.

I found myself in this situation over and over again. I had to do something, but reading productivity books and ignoring the lessons learned wasn’t going to save me. I learned about procrastination, time management, and sticking to my schedule. More importantly, I also learned about “good enough” and managing inspiration overload. That’s where we’re going in the rest of this chapter.

“Something that is often overlooked with creatives is time management and getting shit done. You can be the most talented designer in the world but if you don’t follow through and get stuff out there, it doesn’t matter … Following through and finishing things is one of the most important things you can learn. One of my favorite quotes is “Done is better than perfect.” That doesn’t mean making crap—I believe you should always strive for the highest quality you can—but you have to finish.”

Ben Barry3

Done Is Better Than Perfect

In a University of San Diego study,4 subjects endured a battery of experiments both hypothetical and actual to determine whether exceeding expectations (going above and beyond promises) was symmetrical with disappointment (breaking promises). The study concluded, quite handily, that “Breaking one’s promise is costly, but exceeding it does not appear worth the effort.” To be blunt: people remember when you screw up, they tend to forget when you go all-out.

When it comes to creative work, clients always remember vendors who are late or miss the mark. They quickly forget those who go above and beyond the expected requirements. Rarely are the exceptional remembered for their work, rather, they’re remembered as being on time and budget. Work that was “good enough” would have produced the same results.

“Do you think miners stand around all day talking about how hard it is to mine for coal? They do not. They simply dig.”

Cheryl Strayed5

It’s Hard to Make Great, So Make Good

Head of Creative & Design at HubSpot, Keith Frankel, shared a simple guide to recognizing when a deliverable can be considered “good enough” in a 2014 blog post:6

  • It successfully solves the problem, addresses the need, or conveys the message intended.
  • It is clearly and distinctly on brand.
  • The quality of work is consistent with or above the level of previous work.
  • It has been thoroughly yet objectively scrutinized by other qualified individuals.
  • The final decision of preference had been left in the hands of the creator.

Just freaking ship it. You will always look for reasons to hold back or delay, but if it meets the client’s needs or does its job, it’s ready to go. It’s likely you can iterate on your work at a later time, so get something out there. And if your work is more permanent, like illustration or photography, having something out there is better than nothing. You can always do better next time.

Impostor Syndrome

“For the things we have to learn before we can do them, we learn by doing them.”

Aristotle7

fig0015

As I sit here, writing this book, I have no clue what I’m doing. I am learning as I go along, and I’ll never get it right. It will ship; you’re reading it so unless you’re inside my brain or have stolen my computer, it shipped. My work is out there and the world will keep spinning. Yet no matter how well it does and how much you love it, I will always feel that I didn’t deserve to be asked to write a book and tell you how all of this is supposed to work.

Seeing the work of a seasoned professional, it’s easy to feel insecure. You say to yourself that you’ll never be that good. Even worse, seeing the work of an 18-year-old designer whose work is better than anything you’ve ever done makes you want to set your computer on fire. Then, one day, something you’ve made gets recognized or admired. You wonder if people see all of the flaws. Then you get asked to talk about it, and people want to work with you. You get better, but you never get “good.” You feel like you’re pretending and that people will find out you’re a complete fraud. Well, we are all pretending, even the most accomplished creative in your industry is pretending. We learn enough to get by, but we never know all that there is to know.

“It is not your business to determine how good it is nor how valuable nor how it compares with other expressions. It is your business to keep it yours clearly and directly, to keep the channel open. You do not even have to believe in yourself or your work. You have to keep yourself open and aware to the urges that motivate you. Keep the channel open. … No artist is pleased. There is no satisfaction whatever at any time. There is only a queer divine dissatisfaction, a blessed unrest that keeps us marching and makes us more alive than the others.”

Martha Graham8

Creative culture is being crushed under the weight of inspiration overload. You can spend your entire day looking at what everyone else is creating without doing anything yourself. There is a paralysis that strikes when you start a new project and feel the need to find out what everyone else is doing so that your work fits with what’s out there. You spend so much time comparing your unborn project to finished works that you then wrap yourself in despair before taking the first step.

“Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit.”

Ira Glass9

Thanks to the abundance of online galleries, conferences, blogs, and social media, we get to compare ourselves to the work of everyone around the world, not just our local competitors and colleagues. But we’re comparing our outtakes to someone else’s highlight reel. Most creatives only feel successful when their work is better than everyone else’s. No matter how good it is or whether it accomplished your client’s goal, if it’s not as good as the work it’s compared to, we feel like it’s not good enough. And comparing your client’s goals to someone else’s completed outcome could derail your project. There is so much inspiration out there that you can get sucked into poor solutions for your work to look like, or better than, everyone else’s.

“A few years in I had to stop looking at other illustrators, because if you want to be like them at that point, the best you can be is second best.”

Yuko Shimizu10

As your career advances, you may find yourself surrounded by more and more talented individuals. The tendency to always compare often results in feeling inadequate. The expectations to “arrive” and “succeed” continue to stack up and Impostor Syndrome gets worse as your career blossoms.

“The genuinely untalented, meanwhile, probably have no idea that they’re no good—because they’re too untalented to realize it. (This is the “Dunning-Kruger effect,” inspired by the tale of an incompetent bank robber who thought rubbing lemon juice on his face would make him invisible on security cameras.) In short: if you’re worried you don’t measure up, that could well be a sign that you do.”

Oliver Burkeman11

So guess what? Someone is always going to be better than you. They’ll do work that you simply can’t and they’ll win awards for it. You’ll hate them, and then fall in love with them. Maybe you’ll meet them at a conference and realize that they’re just as insecure as you are. When you see something that inspires you and makes you want to be better, view it as an aspiration rather than a comparison.

“Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure. It is our light, not our darkness that most frightens us. We ask ourselves, Who am I to be brilliant, gorgeous, talented, and fabulous? Actually, who are you not to be? You are a child of God. Your playing small does not serve the world. There is nothing enlightened about shrinking so that other people will not feel insecure around you. We are all meant to shine, as children do. We were born to make manifest the glory of God that is within us. It is not just in some of us; it is in everyone and as we let our own light shine, we unconsciously give others permission to do the same. As we are liberated from our own fear, our presence automatically liberates others.”

Marianne Williamson12

Hopefully, you’ll embrace your craft and realize that everyone suffers from Impostor Syndrome. If they don’t, they’re likely a psychopath. Our work is subjective and its success is largely determined by the approval of others. If it accomplishes your client’s goals, you likely had to make compromises. Working within constraints isn’t an excuse. All that you can do is create the best work you’ve got in you and get it out there.

“Impostor Syndrome is the domain of the high achiever. Those who set the bar low are rarely its victim.”

Margie Warrell13

Procrastination

We self-sabotage through procrastinating. Psychologists have theorized that we, in our current state, see our future selves as a completely different person. From skipping the gym to getting a questionable tattoo, we fail to see the consequences for our future selves any more than we would for a separate person. The result is most of us may choose to procrastinate and let the “future me” deal with the problem.

One of Seth Godin’s most famous pieces concerns our “lizard brains.” Our lives are filled with contradictions. We say we want a creative life, to make something, but we fail to start. Godin quotes Steven Pressfield, who calls this “resistance.” Godin says,

“The resistance is the voice in the back of our head telling us to back off, be careful, go slow, compromise. The resistance is writer’s block and putting jitters and every project that ever shipped late because people couldn’t stay on the same page long enough to get something out the door. The resistance grows in strength as we get closer to shipping, as we get closer to an insight, as we get closer to the truth of what we really want. That’s because the lizard hates change and achievement and risk. The lizard is a physical part of your brain, the pre-historic lump near the brain stem that is responsible for fear and rage and reproductive drive.”14

We are wired to stall, to fear starting so that we may avoid risk. Godin continues, “The lizard brain is the reason you’re afraid, the reason you don’t do all the art you can, the reason you don’t ship when you can. The lizard brain is the source of the resistance.” You will never be able to stop procrastinating; it doesn’t go away. The greatest productivity expert on the planet still has a lizard brain.

We waste so much time on things that have little value, much of it is procrastination from the things that can bring us so much value. Marcus Aurelius wrote, “Stop whatever you’re doing for a moment and ask yourself: Am I afraid of death because I won’t be able to do this anymore?” Do you have that level of commitment to making progress every day?

Fighting Procrastination

What we can do is fight the disease through tactics, constantly at war with our own selves. Heidi Grant Halvorson, an expert on motivation, shares three key reasons we procrastinate and how to overcome them for the Harvard Business Review.15

Reason #1—You are putting something off because you are afraid you will screw it up

Solution: Adopt a “prevention focus.” What you need is a way of looking at what you need to do that isn’t undermined by doubt—ideally, one that thrives on it. When you have a prevention focus, instead of thinking about how you can end up better off, you see the task as a way to hang on to what you’ve already got—to avoid loss.

Reason #2—You are putting something off because you don’t “feel” like doing it

Solution: Make like Spock and ignore your feelings. They’re getting in your way. Somewhere along the way, we’ve all bought into the idea—without consciously realizing it—that to be motivated and effective we need to feel like we want to take action. We need to be eager to do so. I really don’t know why we believe this, because it is 100 percent nonsense.

Reason #3—You are putting something off because it’s hard, boring, or otherwise unpleasant

Solution: Use if–then planning. Do yourself a favor, and embrace the fact that your willpower is limited, and that it may not always be up to the challenge of getting you to do things you find difficult, tedious, or otherwise awful. Instead, use if–then planning to get the job done.

“The work you do while you procrastinate is probably the work you should be doing for the rest of your life.”

Jessica Hische16

As a creative business owner, you have more opportunities to procrastinate than most because you wear so many hats. You’re able to procrastinate on client work, marketing, operations, admin, personal errands, general tasks, and your health and well-being. You have all the options! The grind gets to us and it’s much easier to just check a few more websites or reorganize our desk again. If you work from home, there’s laundry to be done and dogs to be walked; work can wait!

Jessica Hische has mastered the art of “procrastinatiworking” by turning her attention to interesting side projects while she’s supposed to be doing client work. The results have become some of her most successful endeavors. The reason, she believes, is that she was so focused on not doing client work that she had intense focus and freedom of thought in her procrastiwork.

Scheduling and Time Management

As frustrating and cliché as it seems, the single most important step you can take for balancing your work and your business is to manage your time effectively. Administrative tasks can take up as much time as your actual client work. If you’re allowing errands, unexpected interruptions, and lingering conversations and meetings to rule your day, you will never get any work done. The result is that you end up working during what should be your down-time.

There is No Nine-to-five

You work when you need to work. Burning the midnight oil is so normal for creatives that it feels odd to stop at a consistent time and be “off” for the rest of the evening. Working odd hours and having a flexible schedule is a big draw for our industry. However, boundaries sort of go out the window when it comes to scheduled hours and most of us end up working far more than our nine-to-five counterparts. There will always be times when you’re going to work eighteen hours straight to get a project out the door. That’s part of the adventure and the push and drive to finish something. But it shouldn’t be the normal way you go about your business.

So, how do you get a “normal” schedule while running a not-so-normal creative business?

Work in Bursts

The pomodoro is the tomato-god of time travel that will save your life. If you’re not familiar with pomodoro techniques, it was invented in the early nineties by web developer Francesco Cirillo. He named it after the tomato-shaped timer he used while he was a student to track his time. Cirillo broke his time down into short intervals of twenty-five minutes that he timed with the little tomato. For the duration of the timer, he focused on a single task, then took a break of five to ten minutes. He would repeat this throughout the day, often in sets of three or four before longer breaks such as coffee, lunch, an afternoon walk, and dinner.

It has been proven in countless studies to increase focus, attention, and efficiency. The best part of this technique is that it works no matter where you are and no matter what you do; all you need is a timer. You can use your stopwatch on your phone, an egg timer, an hourglass, or get yourself a cool tomato timer. You can get apps to help you understand pomodoro and keep up with your performance.

Don’t Waste Your Best Hours

Many time management books and blog posts will tell you to become a morning person and start at 5am. While that’s a habit many creatives have found useful, myself included, it’s not for everyone. You have to lean into your strengths and do what works for you. If you work best at 2am, then build your schedule accordingly. Just have a plan and stick to it. Make your schedule public with the people it affects including your family, clients, and colleagues. Set office hours. Your office hours don’t have to be nine-to-five, but you should have a regular time period when you’re actively working.

What is important is to use the hours at the start of your work day to do your critical work. If you check email and Twitter first thing, someone else is now dictating how your day will go. Start your day by getting the most important thing done, that way it’s over with. Mark Twain called this “eating your live frog.” We’re most creative in the morning. Again, “morning” is a relative term depending on your lifestyle. Whenever you get up, that’s your morning. Our prefrontal cortex is the most active during and after sleep.17 Successful creatives use their first few hours to invest in themselves and the deep thinking required to do the work.

Your Schedule Is Your Life

You can’t separate your work schedule from your personal schedule, so don’t try to. We’ll break this down a bit more with time blocking. No matter what method you use for your schedule, you have to keep your personal and professional calendars together. You’ll have errands, appointments, and interruptions that come up in the middle of the day. The benefit to making your own schedule is that there is no paid time off or vacation bank to work from; you’re the boss. The downside is that you don’t have strict guidelines forcing you to schedule doctor appointments or trips to the salon on the weekends like everyone else. While this is great for getting the appointment you want, it can blow up your work day.

I carve out a set block of time on Friday mornings each week for appointments and other personal errands. I take advantage of being my own boss and staying out of weekend crowds, but I don’t let appointments pop up at random times.

Kill Multitasking

The fastest way to rot your brain is to multitask incessantly. Psychologists have conducted countless studies and concluded, with certainty, that there is no such thing as multitasking—it’s simply task switching. To clarify, you actually can’t focus on two things at the same time, one of them is being done with limited brain capacity.

The solution, and alternative, to multitasking is Time Blocking. Cal Newport of Study Hacks has popularized Time Blocking as a way to overcome the impossible pile of tasks and deliverables most knowledge workers face each day. We can choose to ignore tasks or leave them incomplete. If we have any hope of completing them all without frying our brains, the only sustainable solution is to plan every minute of your work day.

As horrible as it sounds, planning every minute of your day is actually far more freeing that simply floating around to see what happens. It’s been proven that people who develop the habit of strict scheduling, such as Time Blocking, have more free time and enjoy it more. Newport says that a “40 hour time-blocked work week, I estimate, produces the same amount of output as a 60+ hour work week pursued without structure.”18

Use Time Blocking

Entrepreneur and Business Coach Kate Matsudaira took Time Blocking to the next level with her Spark Notebook, something I’ve bought into completely. You have probably tried dozens of productivity apps, task managers, and systems to get a handle on your schedule. The app store is home to more productivity apps than Angry Birds games. You may have found an app or system, such as Wunderlist or OmniFocus, that does the job. But the time it took to put everything in an app just never worked for me.

Planning your schedule is thinking time, not doing time, and you should do it away from your computer and phone. Getting it into a hand-written notebook and forcing yourself to take the time to think through it drives focus and keeps you from checking email and social media. Forcing an analogue process into your digital workflow can do wonders for attention to detail.

Kate defines Time Blocking as “just a method for planning your day. And the reason why it works is because it forces you to focus on your top priorities for an amount of time that reflects their importance.”19 Using a notebook or other tool, you break your day into morning, afternoon, and evening. In blocks, you write down the things you need to get done and put a checkbox next to them. When you do them, check them off and move onto the next thing. It’s simple, yet extremely powerful. The key is to put everything in there. Even if it’s as simple as “go get coffee” or “text mom,” put it in your time block. Put a number next to it for how long you think it will take.

How you can use time blocking

When you estimate how long something is going to take, don’t lie to yourself. Be honest about knowing how long it will take you, not how long it should take anyone else. If you know you’re prone to procrastinate with certain tasks, then you need to build in some of that time. You can’t change your habits overnight. Add an extra fifteen minutes or half hour and then work as if you don’t have it; try to finish early. The more buffer time you have between blocks, the less stressed you’ll be. Use a time-tracking tool religiously and even look into Rescue Time or Slife, a tool that monitors all of your on-computer activity. You can’t improve what you don’t measure.

Kate’s tips on sticking with Time Blocking include:20

  • Focus on a single task; close everything else including email and social media. If you can, put your phone on do not disturb.
  • Find your rhythm for getting the hard work done. For most, it’s early in the morning when you have the most willpower. Don’t use your best focusing time on low-quality tasks like email and busywork.
  • Always front-load your week with more than you think you can get done, especially on Mondays. It’s easier to push hard earlier in the week and move things back than to play catch-up as your week goes on. This helps with procrastination and, if you finish things early, you could just take off on Fridays.
  • Break projects and features into very small pieces. It helps you to start on something small vs. looking up at the mountain of work that encompasses the entire project. It also makes it easier to be productive in fifteen minutes when your schedule shifts; you can still get something done.
  • Your personal schedule and work schedule are the same. You work for yourself so that you can go the doctor or salon on a Thursday when it’s easier to get an appointment, and that affects your schedule. Likewise, if you are running errands on the way to work or working out in the middle of the day, it needs to go in a time block.

“In the context of work, uncontrolled time makes me uncomfortable. If you’re serious about working deeply and producing high-end value, it should probably make you uncomfortable as well. Using your inbox to drive your daily schedule might be fine for the entry-level or those content with a career of cubicle-dwelling mediocrity, but the best knowledge workers view their time like the best investors view their capital, as a resource to wield for maximum returns.”

Cal Newport21

Location shifting

Time Blocking works best when associated with triggers, and one of the most powerful is location. When you’re at your desk, you work, and when you’re in your favorite chair, you relax. It can be taken to the next level by actually breaking up your work day by location.

An example may be starting your day at the coffee shop to journal and plan. Then, move to your desk for mid-morning creative work. Then go to lunch, then back to your desk, and then a walk, and then maybe another shift to somewhere else in your home or office, then the gym, and so on. By setting your triggers for tasks to locations, you are limiting your time and resources to accomplish the task. It pushes you even further to get things done in the fixed window of time.

Meetings About Meetings

Meetings can hurt your flow and slow your productivity. Even if you stay solo, the volume of business development, project status calls, and “check-ins” that come along as you fill your book of business can consume your entire day. When people ask me why I left a comfortable corporate job to start my own business, my first answer is always, “I had too many meetings about meetings.” Communication is critical for a business to survive, and online channels such as email and instant messaging can consume just as much of your time as meetings. But meetings typically involve travel to and from the venue, someone being late or going over, and small talk that can add a full half hour.

Meetings cost creatives more. People who make things have a different schedule from those who manage them. For example, a writer can’t set aside an hour to write; she needs an entire afternoon or evening to get into her flow and work out the piece. A manager, conversely, has meetings all day and is used to switching from one conversation and task to the next. They are each wired to work a specific way. For the creative business owner, you wear both hats: maker and manager. It can take a toll on your creative output.

Getting control of meetings

While avoiding meetings altogether isn’t possible, you can control them. At my agency, we have all of our full-staff internal meetings on Tuesdays. No other internal meetings are held any other day of the week unless they are absolute emergencies. The first half of Tuesday and Thursday, and the entire days of Wednesday and Friday are banned from meetings. We encourage the team to take this further, me included, by turning off notifications and chat during these windows. On non-meeting days, we set aside two designated times at mid-morning and late afternoon for project check-ins.

Meetings can be successful, and there are ways you can get the most out of them when they have to happen:

  • Always question the meeting. Can this be handled with an email or can someone else take care of it? Can it be delegated?
  • Always look for an alternative. How about a call or a quick stand-up discussion?
  • However long you think you need for a meeting; cut the time in half. Set a timer for that amount of time and when it goes off, the meeting is over.
  • Only include people who have to be in the meeting; don’t even add them as optional to the invite.
  • Take notes and post them for everyone else to view if they so choose.
  • Have an agenda and stick to it; send it ahead of time. If you can’t prepare an agenda, then it’s not a meeting; it’s a one-to-one conversation.
  • Make meetings online or by phone whenever possible, use chat tools or set up a conference call so that people can return to work as soon as the meeting is over.
  • Combine face-to-face meetings with other tasks such as lunch, breakfast, or exercise. Get people to walk or work out with you instead of just sitting around a table.

Delegation

Outsourcing expert Chris Ducker created an exercise to help you find what you should move off your plate and onto someone else’s. Make a list of the things you don’t like doing, can’t do, and shouldn’t do. Then, find someone else to do those things for you. When you get this stuffout of the way, it helps you have more time to do what you like doing and to get your work out there.22

At some point, you’ll have to let go of some things that you do like doing and get help. Either employees, freelancers, or virtual assistants will be doing tasks that you wish you had the time to do. You are your own worst enemy when it comes to delegating interesting work. Something I learned is that the better I am at delegating tasks, the more time I’ll have to work on at least some of the tasks I enjoy. If I am not effectively delegating, I’m scrambling to get things done and I end up doing more work because we’re behind.

How to Delegate

You are not the only one. Despite my Neo complex, I am not “The One.” There are others who are better than me at certain tasks. I should hire those people to complete the tasks for me.

They aren’t you, so they won’t be perfect. They may do a better job in the eyes of the client, but others won’t do exactly what you would have done, so you may not be “happy” with the work. If the work meets the client’s goals and all other criteria, it’s good enough. Just ship your delegated work.

fig0016

Over-explain. You can’t give too much information, but you can give too much direction. Supply as much background as you can and let your employee decide what to do with it. However, don’t tell them exactly how to do the work if they have their own process. Sometimes their methods may be better for their workflow.

Set boundaries. While you shouldn’t tell them how to do it, you should still be specific on parameters. Employees will go as far as you let them or do as little as possible. It’s not based on personality either, it’s based on the expectations you set. Tell them if the client is a huge deal and expects top-notch work or if the client is low-priority and will be fine with “good enough.”

Check it, correct it. Have set check-in times where both you and your employee are prepared to review the status of work in progress. They are in a question and feedback mindset and you are in an answer and correction mindset. Review the work thoroughly and provide constructive feedback whether there are changes or not. Let them know what they did right that they can continue doing in the future.

Let them screw up. If you dig them out of every hole, they won’t learn. If it’s work going directly to a client, you have to fix it. But you can allow your employees to make mistakes and correct them before shipping off the work. Don’t fix it for them; fix it with them.

Teach a man or woman to fish. Show them how, not just what, to do. Let them know how you do it and then they can decide if it’s the right process for them. Let them take the lifecycle of the work as far as possible up to and including interfacing with clients.

Increase over time. As people show promise, increase their responsibilities.

When to Delegate

  • You’re out of time, and the project has to ship.
  • It’s a task that you don’t want to do.
  • It’s a task that you enjoy, but shouldn’t be doing.
  • It’s a task that you should be doing, but someone else can get it done faster or cheaper with similar results.
  • You’re out of money, and you can outsource to get things done cheaper.
  • You need another perspective or idea.

Side Projects

It’s good for the soul to do something different. The best way to branch out is to experiment with side projects. You may learn you’re great at something, so good you may even start offering it to clients. Or, you may learn that it’s good you aren’t making your living at a particular skill or in a certain market. Otherwise, you might be flipping burgers soon.

Side projects can be revenue generating. Some of the most popular apps and services on the web started out as side projects including Basecamp, MailChimp, and Flickr. The goal of side projects shouldn’t necessarily be revenue. Otherwise, they’re just another project, but it’s perfectly okay to think about a financial future for the work as you go along.

Do Stupid Stuff

Side projects should be stupid. Keep things simple and don’t take it so seriously. When you’re working with clients, there’s a lot on the line, so you can’t be too laid back. When it’s a side project, you can let go of much of the pressure and just enjoy the ride. It can be daunting because you’re the client, so you have no boundaries or deadlines holding you back. It’s easy just to let it go because no one is watching.

Break Out Of Your Comfort Zone

Side projects certainly don’t have to be an extension of your primary creative role. If you’re a writer, your side project may be a clothing line. If you’re a developer, it may be a board game. It just needs to flex your creative muscles (and maybe even your physical ones). Side projects should be far enough away from your work to feel like a break, but not so far away that it’s a hobby. They can be as simple as a personal website or tutorial, but it’s important that they still feel a bit like work. The biggest takeaway should be learning. Whether it’s learning a new programming language or design style or building something with your hands instead of a mouse, it’s about finding new ways to think.

They Can Shift Your Perspective

The best part about side projects is that they allow you to see your day-to-day work in a new light. They may help you to fall back in love with your craft if you’re feeling burned out. They may show you that you enjoy something else more and can push you toward a new endeavor. The important part is just to start; it’s just a stupid side project.

Stick With It

Meaningful work and sustainable growth stem from learning to work on your business instead of just in it. Don’t let your operations and client communication tasks stack up. On a weekly basis, work on your business and step away from client work. Set aside time for uninterrupted work and don’t allow the daily grind to infect your creative time.

Whether it’s hiring professional services such as accountants or bringing on employees and contractors, it’s unsustainable to do all of the work yourself for the long-term. Asking for help and allowing others to do some of the client work while you’re working on marketing, operating, and improving the efficiency of your business is hard to do, but it’s necessary. Regardless of your company size, one or a hundred, only by setting boundaries and clear goals can you free yourself to continue doing the work that you love.

Notes

1. Steven Pressfield, The War of Art: Break Through the Blocks and Win Your Inner Creative Battles, p. 86.

2. Paul Wilson, Calm at Work.

3. http://99u.com/articles/7118/facebooks-ben-barry-on-how-to-hack-your-job.

4. http://www.chicagobooth.edu/capideas/magazine/winter-2014/dont-bother-doing-more-than-you-promised.

5. Cheryl Strayed, Tiny Beautiful Things: Advice on Love and Life From Dear Sugar.

6. http://blog.hubspot.com/marketing/good-content-creation-design.

7. Aristotle, The Nicomachean Ethics.

8. Agnes de Mille, The Life and Work of Martha Graham, p. 264.

9. http://nprfreshair.tumblr.com/post/4931415362/nobody-tells-this-to-people-who-are-beginners-i.

10. http://99u.com/articles/29941/yuko-shimizu-make-your-own-path.

11. http://99u.com/articles/32985/nobody-knows-what-the-hell-they-are-doing.

12. Marianne Williamson, A Return to Love: Reflections on the Principles of “A Course in Miracles”.

13. http://www.forbes.com/sites/margiewarrell/2014/04/03/impostor-syndrome/.

14. http://sethgodin.typepad.com/seths_blog/2010/01/quieting-the-lizard-brain.html.

15. https://hbr.org/2014/02/how-to-make-yourself-work-when-you-just-dont-want-to.

16. http://www.humblepied.com/jessica-hische/.

17. http://www.publicationcoach.com/best-time-to-write/.

18. http://calnewport.com/blog/2013/12/21/deep-habits-the-importance-of-planning-every-minute-of-your-work-day/.

19. https://popforms.com/how-to-do-time-blocking/.2https://popforms.com/how-to-do-time-blocking/.

20. http://calnewport.com/blog/2013/12/21/deep-habits-the-importance-of-planning-every-minute-of-your-work-day/.

21. Chris Ducker, Virtual Freedom.

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