Strategic Planning For Creatives


It may be obvious to you, but this is something that I have only come to know recently: strategic planning is the only way to actually make progress toward your goals. Very often my plan for the new year was built upon nice dreams: wouldn’t it be great if I could accomplish this, life would be so much better if I could only do… But this kind of dreaming always left me feeling unfulfilled.

Here’s the story.

Twelve years ago, I was 21. In the middle of college, dreaming all the big dreams while focusing on school work and perfecting my violin playing. My ultimate vision at that time was to be a professional musician, traveling around the country with my violin, composing and performing original pieces, having a blast and living out the Starving Artist story.

And, as life goes, I start living out this story that I had been creating for myself in my head. I met an amazing woman who became my duo partner for The OK Factor, my junior year. We started writing together, we graduated, kicked the duo into high gear with summer tours, song ideas, and in-home recording sessions.

And after a while, we’re still hustling for the sake of hustling because that’s what we think will help us go places.

We’d come up with project ideas, we’d execute. We’d quickly burn out. And then we’d do it all over again – for about 5 years straight.

By the time I turned 29, I realized that I had accomplished my “ten-year vision.” I was absolutely living the Starving Artist story, mostly making ends meet with creative pursuits and generally loving it, minus the burnout and lack of cash flow.

Living so in the moment, moment to moment, had not left me with time or space to reflect, assess and dream for the future. I had never looked up to realize that I had already achieved the story I had been telling myself. And I hadn’t taken the time to ask new questions like, is this where I wanted to be? What is working and what isn’t? And what do I want my future to look like now that I’ve gotten this far?

Enter Seasonal Planning

Now, I ask myself those questions on a much more regular basis. Every three months I do what I call “seasonal planning”, which is my fancy creative way of saying quarterly planning. My whims and ideas ebb and flow along with the seasons, so it only made sense to start crafting a system that worked for me instead of against me.

Here’s how it works:

  1. Every November or December I look back on the year and reflect on what happened. I think about my personal life, my creative pursuits, my business, everything.
  2. Then, I create or revisit my ideas for where I’d like to be in ten years. You’d be surprised how much this ten-year vision changes over the course of 365 days. It’s good to check in on it once a year and see if it still feels good.
  3. With that long-term vision in mind, I map out the first steps I could take in the next year that could get me closer to that goal. Backed by the data and information from the past year, I can make more informed choices for what to focus on.
  4. And then I consider the next 3 months, the time I have right in front of me. I choose items to focus on from what I call my “Inventory,” the four categories that make the most sense to encompass what we do as creative people: Management, Creation, Brand, and Lifestyle.
  5. The most important part of all of this is defining what growth and success will look like during this season. I consider my mental health, my family obligations, holidays, global happenings (aka pandemics), etc. I choose metrics to track based on what feels good and what I’ll realistically be able to accomplish.

I keep these goals front and center on a bulletin board in my workspace so I see them all the time. And if I’m getting off track, I either adjust my metrics or adjust the goals. No judgement allowed.

Grab a copy for yourself or your creative bff

I’ve packaged up this seasonal planning system into what I call The Creative’s Almanac. The new edition will be coming out so soon, and you’re going to love it.

Inside you’ll find the exact framework I described above, plus a few other helpful tools like a Gut Check, a New Year Pep Talk (my favorite), and a Word of the Year exercise. It’s actually awesome and I can’t wait for you to check it out.

You can grab a digital copy and get rid of your new year anxiety with a flexible and strategic plan for less than a trip to Target. Promise.

Take a peek at the excerpted edition here, and check back soon for details on next year’s Almanac!

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