Starting a Creative Agency: Year 1 in Review

Scroll this

You dive off the cliff. The rush is incredible. You hear the passing whoosh of amazing sounds, like:

“Congratulations! You’ve taken the leap! You’re doing what we all consider doing from time to time!”

“You’re gonna do great.”

“…love that you’ve branched out into running your own agency. It’s a dream a lot of us have, but so few ever realize.”

True words. Yet, unless the speakers are also sending you business, no level of verbal encouragement will see you through. It takes talent, guts, hard work, patience, more hard work, determination, and lots of hard work.

What’s It Really Like

A little over a year ago, my wife and I founded dogstar★creative.

Having your own shop is a dream come true. Some days. Those days are filled with high fiving partners and clients, solving things on the fly, working with great people, quick access to decision makers, and watching exciting things unfold quickly. Projects run smoothly, you get to play with super-talented teams, and the creative output is some of the best you’ve seen—making the experience both an honor and a pleasure. Everyone’s excited. Smiles all around. New opportunities are coming in. More high fives!

Aren’t you glad you did this?

The Pendulum is Always Swinging

Other times, running your own business is a bit of nightmare.

Last week you poured 20 hours into new business discussions that ended up going nowhere. It’s not the first time, but now you’re thinking it needs to be the last time. Markets are disturbed by forces outside your control. Projects get put on hold, and even when it’s temporary, it creates a cascade of timing, workflow, and cash flow adjustments.

There will be times when everyone feels pulled in too many directions. If you and your lovely cofounder move to a new city, get married, have another baby, and publish a book—all in the  same year of founding your business—well, just remember, there’s no maternity or paternity time-off compensation package for either of you.

You will work endlessly and tirelessly—at all of it. No one will understand what you’re going through, unless they’ve done it themselves. No matter how mindful you might be in working to keep a work in balance with family, if your toddler keeps chanting “Now you are now done working now,” he will eventually himself prove correct. For the time being. And you will have another late night.

Whether you have kids or not, in your first year, you’ll encounter plenty of sleepless nights for lots of reasons.

You’ll spend more time and resources than expected on taxes, legal, accounting, licenses, marketing, networking, IT, web and social media, and so many other things. You will lose the blog post you were writing with the 5 incredibly insightful things your Director of Operations (and previously mentioned lovely wife) has learned in the past year. Then neither of you will be able to remember them.  

You may encounter unethical savages who will openly steal your ideas for their own benefit. Will you really have time for litigation? Can you really afford litigation?

You’ll think you’re still having fun and loving what you do, but you’ll wonder if there’s really any other option. It’s just who you are. This is just what you do.

Why did you do this?

Why We Do It

It really is a roller coaster ride. Things will go wrong. And you’re on the front lines, all the time, with no buffer. That’s not necessarily bad. It can be pretty fun. But it’s true. Different people handle different aspects of that better than others.

So why even do it? With all the hard work, endless nights, and risk—why?

I’ve met with dozens of entrepreneurial creatives over the past year in Portland and San Francisco. Here’s why we do it.

  • We need autonomy
  • We grew up in family business, it’s how we’re wired
  • We want or need creative control
  • We want to avoid big agency bureaucracy
  • All of the above

For me, it was all of the above. It gets tiring at times. But when I look at the opportunities before us, the work we’ve done, and the people we’ve had the chance to work with (plus, the people we hope to work), if nothing else, the experience and the education has been well worth everything we’ve put into it.

For the record, none of the creatives I met said, “we’re doing it for the money.” They do it first-and-foremost because it’s simply who they are. Whether they have a photography studio, a design business, a video production company, or do sound design, these entrepreneurial creatives do it because they love their art form so deeply. They do it for the purity of being happy with their work. They learn money will come and go, contracts and clients will come and go, but it eventually gets better over time. And for every person that breaks their promise or hire that doesn’t come through on a project, there will be a hundreds that prove their integrity to be beyond question or shine their talent at just the right time.

What We’ve Learned

The past year has been a constant learning experience. I asked our Director of Operations, Clarisa Moore Vanisky, what she learned. Here’s what she said:

  • You can use your client’s budget for actual work, remain flexible, and keep overhead low. As business grows, you’re in a better position to manage those add-on business costs.
  • You have the opportunity to network and learn from other people in the business. At a big traditional or digital agency, your work exposure is generally limited to working with your internal team. Smaller and more nimble agency structures let you learn about what others are doing across the creative industry. This enhances how you look at things, strategize, and tackle creative projects.
  • You can achieve an actual work/life balance. You may target a 9 to 5 day, and instead, it might end up being 9 to whenever, every day. But then you also have the flexibility to go your son’s first school field trip, and catch up on work before or after. You’re less fried, happier, and doing a better job for your clients.
  • Even while operating on a senior level, you’re involved in the day-to-day creative work. You’re not spending your days sitting in meetings, then presenting work done by others. You’re part of the crafting and presenting work you were actively involved in.
  • You never have enough time.

Here are the top 5 things I’ve learned in the past year.

  • Family comes first.
  • You never have enough time.
  • The entire creative industry is more wonderful and messier than anyone could ever imagine. Already in constant flux, people now fear AI and automation are coming for their creative jobs. Etcetera and so on.
  • Teaching your kids by example will push you to do crazy stuff.
  • I’m my worst client. When it comes to generating ideas, collaborating, having conversations, and doing stuff with words to help others, I’m always good. When it comes to marketing my own business and products, it’s easy for me to get distracted by a fresh creative challenge.

In summary, I’d do it all again tomorrow. In fact, I surely will. Every day is Groundhog’s Day.

*Thank dog for family and friends.

Submit a comment