How to Be a Pain in Your Own Ass as an Independent Designer

Editor’s Note: The following piece on creative entrepreneur learning curves was contributed by Maria Rapetskaya, founder and creative director of Undefined Creative, an NYC–based boutique motion design firm.

In your former life designing in-house or at a firm, someone else paid the bills and filed taxes, tracked profits and losses, and made sure that the work kept rolling in. These things weren’t your headache. You’d been hired for your amazing skills, skills that you eventually came to believe would serve you better if you were the boss.

Thus, you fell in love with the idea of (insert your company name here) and, upon formalizing your business entity, thought the two of you would live happily ever after. But perhaps the honeymoon ended with the first batch of invoices and bills—all of which were now your problem. And perhaps that was only the beginning. …

If you’re kind of freaked out that everything is now your responsibility—from setting the course of your business to writing the checks to actually using those amazing skills you have to bring in the income—then here’s how to handle being the boss.

Creative director Maria Rapetskaya shares tips for that learning curve that every independent designer must undergo when learning to report to themselves.

Photo via Unsplash

Report to Yourself Regularly

Knowing how to not report to anyone else sounds like a made-up skill. But, until you grasp this one, the next three on this list will be hard to tackle. The ugly truth is nearly all of us are guilty of skirting at least a little responsibility when we work for others—a little white lie here, a bit of time wasted there, a handoff to someone else. When your role is limited by a job title, and others are around to pitch in, there’s less risk of screwing up big time.

As a creative business owner or independent designer, you shoulder all the risk. Its even possible for you to set off a chain of events that’ll keep coming back to haunt you. Slacked on sending invoices and couldn’t pay some bills on time? It’ll be you who can’t qualify for a line of business credit. Forgot to follow up on promising job leads? You’ll regret it during the next slump in your production schedule. Didn’t give a “lame” project your best effort? That client could have become your biggest. And now they won’t.

Having employees or partners doesn’t automatically excuse you from being involved. Your partners are responsible for their own areas of focus, and as for your employees … let me remind you: We all slack a little when someone else is the boss.

First and foremost, reporting to yourself is learning to be brutally honest. What percentage of your intended task list did you actually complete today? How much time did you really waste on Instagram? Are you unacceptably behind on billing or invoicing? Are you guilty of excusing yourself from tasks you hate? Pay attention to the things you tend to avoid and the ways in which you creatively waste time. If you don’t learn to boss yourself around, life will do it for you.

Stay Organized

Don’t let things fall through the cracks for too long. Rescue missions cost far more in time, money and effort. Throwing your receipts into a drawer doesn’t qualify as bookkeeping. Fail to track your expenses, and you won’t know which jobs are profitable and which aren’t. When you finally hand off that drawer to an expert, you won’t remember how to classify half of those receipts—wasting their time and your dollars.

Listing your regular tasks also helps when reporting to yourself. Identifying your daily/weekly/monthly musts, especially ones you loathe doing, gives you a checklist against which to evaluate your own performance as a business owner.

Manage Your Time

This third skill makes you better at the first two. Once you’re reporting to yourself, you can form a good picture of how you manage your time currently. When you get organized, you’ll know how much time to allot for the standard must-dos. To be efficient, determine your personal preferences.

Do whatever you can to reshuffle your day in accordance with your personality. If you’re most focused in the mornings, use your mornings to do the tasks that need the most focus. If you’re a night owl who has a pattern of working at 3 a.m., diligently set aside time for those daily/weekly/monthly musts that can only be addressed between normal, 9-to-5 business hours.

If your report-to-self uncovers major distractions, this is where you tackle them. You can’t go cold-turkey on social media, but you can discipline yourself to checking Twitter every two hours instead of every five minutes. 

Find Help Before You’re Desperate

If, despite best efforts at honest assessment, organization and time management, certain critical tasks go uncompleted for dangerously long, it’s time to seek help. You can be a pain in your own ass all you want, but some bad habits are hard to break, and there are only so many hours in a day. Many creative business owners go through a period where they try to, or must, do it all. To them, getting away from that mindset is admitting defeat. Yet, although that sounds negative, it’s simply a part of growing your company.

You didn’t start your business because you’re good at everything. Having to wear new hats exposed you to different aspects of running a company. You now have basic knowledge of what you’ll be asking of someone else. That’s important! Needing help for the right reasons isn’t sign of failure—it can actually signal success.

To close this loop, don’t forget that everyone you hire to help you, whether full-time or on a contract basis, will need your oversight and direction. How well you’re managing your help must become a regular part of your self-reporting.

Take these tips to hear and see what it does for the growth of your creative business. You might be surprised what a little pain in your ass can help you create.


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