We Asked, You Answered: My Biggest Challenge Running a Design Business

Here at Go Media, we’re buzzing about the release of Bill Beachy’s book, Drawn to Business including new extra goodies!  This nuts and bolts strategy guide highlights the successes, failures, the in and outs of growing a design firm: namely, ours.


It made us think: What challenges do our friends and colleagues face? Which are universal? Which are unique?

We asked, You Answered:

What is your biggest challenge running your design firm or freelance business?


“My biggest issue is time management. No matter how organized you are, you can never predict when a project will go long and make all your other deadlines a hundred times more stressful. I don’t know if I’ll ever be able to crack that one. Burning out is always a concern, but I know my desire to create isn’t disappearing any time soon, so it’s more about exhaustion than anything else. When you combine tough timelines and too many late nights in a row, it could potentially spell disaster. Well, short-term disaster anyway. There’s always a light at the end of the tunnel.” – Jon Contino

Jon Contino |


“The biggest problem that I have running my freelance operation is maintaining a balance with my social life, and happiness level in general. We assume, early on, that if we work hard enough, we can achieve a certain level of success. It is also our assumption that that level of success will bring us a wealth of happiness.

It doesn’t.

Achievement of our goals only prompts us to set a new goal, instead of taking any time to enjoy reaching a milestone. After doing freelance design for over a decade, I have set goals and achieved them – only to set a higher goal for the following year, and thus put myself right back to the grind – glossing over any chance to pat myself on the back.

It’s possible that continued success in a creative field has an adverse reaction to one’s happiness. Being creative all day, every day, gets more and more taxing. The well of ideas threatens to dry up, and we put more and more pressure on ourselves to stay afloat. The quest for “better” is admirable, but also tortuous.

This grind keeps me in my cave, churning out work, giving myself little to no interaction with the outside world. More success, for me, has led to a very reclusive lifestyle. On paper, I’m experiencing the most successful time of my life – in reality, I can’t remember the last time I sat down with a friend for coffee.

The solution? Move happiness to first on your priority list. Meeting with people you enjoy or doing things you love can put you in a positive frame of mind that’s more equipped with managing a heavy workload. This positive outlook instantly manages stress better, and is more effective at calculating an otherwise chaotic and overwhelming to-do list.

Days may look less like a row of fires to put out, and more like the privilege that we began these careers with – that, while others toil through jobs that they hate, we get to be creative for a living.” – Brandon Rike

Brandon Rike |


“The biggest problem I have running a business is
“running a business”.

Design and illustration work is no problem at all outside of solving those creative problems, but handling growing and maintaining a business on top of that is almost an extra job.

One that can consume entire days at a time doing bookwork, communicating with clients, putting proposals together and promoting and marketing my brand.

I prefer that that’s the obstacle relative to what I do
if I have to choose one.” – Aaron Sechrist

 | OKPANTS Design Co. |


“The biggest problem I have running my business is the constant balancing, though I imagine that’s just a life problem that everyone has, at least to some degree. Also it’s been apparent to me for awhile that I am not a financial planner and my bookkeeping is sloppy, so I am making that a big priority and am hiring some help so I can learn better habits. Cash Rules Everything Around Me, around all of us, so the saying should go.” – Margot Harrington

| Pitch Design Union |


“The biggest challenge for me is not knowing: not knowing if you’ll have work in 6 months, not knowing if you’ll stay relevant, and not knowing if you’ll have the courage to keep fighting for the work you really want. Coincidentally, that’s also the greatest part too.”  – Timothy Goodman

| Timothy Goodman |


“Being a Freelance artist and holding a full time in house design position during the day, as well as having a family with small kids, I have a hard time finding a balance.  It’s been a real challenge building my freelance career to the point where I feel like I could take the plunge to self-employment.

From a freelance perspective, I never lack for work, it’s the lack of jobs that have a large enough budget to sustain a family. It makes it even more of a difficult decision when you love your full time job. Wouldn’t it be easier if I hated what I was doing?

I always question, would it be worth it for me to work 80 hours a week for myself just to make ends meet? Would I be potentially picking projects that I don’t really enjoy, just to be self-employed? At this point, because I don’t have to worry about the bottom line, I have the opportunity to be selective in the work I take on; I only pick up projects if they sound fun or if I feel like its an opportunity to propel me to the next level.

So, my biggest problem is questioning, am I making the right decisions for myself and for my family? I don’t know…! ” – Derrick Castle

| Straw Castle |


“Our biggest battle is perhaps the pigeon hole we made for ourselves as “poster designers”. We are fully capable of so much more, do it for a handful of clients, are dying to do more, but need to get some larger clients to recognize that we do so much more than just gig posters. I get the feeling that people think we wouldn’t want to do corporate work, because our poster work is so edgy. However, we know what is appropriate and when, and really get a thrill strategizing long term and sustainable design projects.

So, this has created a bit of a wall, dividing us from getting invited to bigger pitches or bids.” – Jason Teegarden-Downs

Delicious Design League |


“Perhaps the biggest issue running our business is being pulled in too many directions at once. Managing a startup has one true base concern – making money. Our approach to that has always been a client-first mentality, and assuring satisfaction is a key part of that. With such a heavy focus on that, we work daily to refine our processes in what we’re doing to ensure a high level of quality. But, by doing that, it leaves little time to focus on the little moving parts in a business – guaranteeing cash flow with new projects, completing current projects on schedule, revisions to bring projects up to proper quality, payroll, accounting, taxes, and managing employees are just a few of the balls to juggle.” – Jon Savage and Simon Birky Hartmann, partners at Studio Ace of Spade

| Studio Ace of Spade |


“I’d love to be a household name, but as a sole business owner who can’t yet afford an employee, I struggle with the age-old ‘It’s hard to work on your business while you’re working in your business.’  My days aren’t really my own to plan – I can have a plan, but customers and visitors have their own agenda. Money is also an issue. I’d love to get out from under my start-up costs – I’d be so less stress-y.  I had a business partner when I started but it didn’t work out (which is OK), but I took on some debt that I can’t seem to get paid off fast enough.” – Chrissy Jensen

| Domestica |


“My biggest problem running my freelance business is figuring out a relaxed way of doing active acquisition. Thus far I’ve been blessed with a steady and stable income of clients that reached out to me. I know that at some point I have to reach out and start doing some active form of acquisition myself. In fact, I probably should do it regularly just to personally ensure a continued flow of work. But I can only muster the time and energy to focus on the great workload still in front of me.

On the one hand I feel great about still having more than enough work, on the other hand I know that there might/will come a point when things slow down a bit. Money buffer aside, there will be a point when I’d have to do outreach myself. Which is not something I’m scared of, I just haven’t figured out a way to make that part of my freelance career feel less nerve-wracking. I still need to find a way that feels more relaxed to me or rather; not as forced and “sales-y”.

Perhaps this is caused by my inexperience in it and my current luxurious position in which new clients continue to ‘knock on my door’. Not having a smoothly paved down outreach method from my end actually isn’t so much of a problem. It’s just a part of my freelance business that doesn’t feel extremely comfortable to me yet, but (at some point) it has to be done regardless.” – Maarten Kleyne

| Maarten Kleyne |


“On a daily basis I struggle with staying on top of the BUSINESS part of it. Being a solo shop for 12 years I have failed miserably at that part and it is a big goal for me in wrapping up 2013 into 2014.

As far as reaching the next level, I struggle with getting out of my own way. Realizing that I can indeed do this. I have been on a somewhat self-destructive path creatively and recent events (including WMC Fest!) have really turned me around and shown me the way along with my own desire to be what I have always wanted to be but either a) never thought I could, or  b) made excuses to not push forward and grab hold of life and do something with it!” – Lenny Terenzi

| Hey Monkey! Design |


“I have been concentrating on developing a presence here in this city, and I feel like I am making strides, but taking my brand into a new market is the current challenge I have set for myself. I set up an online store, and I’m developing multiples so that I can get my stuff into the hands of more people in an affordable way. It’s also really important for me to make personal connections with people, so I don’t want to lose that aspect of my business.

I also have run up against my own time limits. I rarely say “No” to anything. Maybe later in my career I will be able to afford to pick and choose, but I feel like right now I have to hustle and take on everything and anything that comes my way.” – Angela Oster

| Angela Oster |


“There’s no single issue. The problems and challenges are different every day, and you have to face them. HEAD ON.” – Scott Fuller

| Studio Temporary |


“Staying original in your work, especially when clients want generic work that looks like everything else. Teaching them that it’s good to have a unique design in their products, and to stand out!” – Zach Reed

| Zach Reed |

What’s your biggest challenge?

We want to know! Share with us in the comments below!

Pick Up Drawn to Business…

to learn about the challenges President Bill Beachy faced growing Go Media and the everyday hurdles (and successes) that keep us on our toes always.


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