Plan your creative career 2018 part one: Why and how to plan

“Plan” is an ironically vague term. You can plan to stop by Target on your way home, and you can plan a detailed, day-by-day, hour-by-hour itinerary for a trip. Same word, completely different results.

I think this is what makes business planning such a confusing and sometimes frustrating experience for a lot of people. As a freelancer, what I plan to do and what I’m actually able to achieve are often very different things: I can say that I want to be publish five articles a month, but that’s contingent on whether I can get anyone to bite on my pitches or not, or on what other work I get over the course of the month. When I fall behind (which happens more often than I care to admit), it feels like planning is just an exercise in frustration. It feels like it makes more sense for me to not plan, to just go where life and work take me. If that’s what ends up happening anyway, why frustrate myself with goals that may never come to fruition.

The thing, though, is that any smarmy business magazine will tell you that planning is crucial for business success. And if you’re a freelancer, creative or not, you’re running a business.

(In some ways, the term “freelancer” is kinda subversive because it makes it seem like work is more of a side gig or hobby. If you’re freelancing full-time, you’re an entrepreneur.)

The question, then, becomes what to plan. As I’ve said, having hard benchmarks to meet can end up making you feel frustrated and even angry with yourself. They can be really discouraging if you’re not getting to where you thought you’d be. At the same time, you can’t plan for every contingency. Life happens, and sometimes it can derail you. Hard. That’s not anyone’s fault, but it does undermine the process. So what should you plan, and to what extent?

I can’t say what you should do. I’m not your mom. But I can tell you what I do! My planning process has evolved a lot since I started freelancing in May 2016, and here’s what I’ve learned so far:

Break up the year in a way that makes sense for your work.

I’ve found that planning month-to-month just doesn’t work for me as a writer. Pitching is a long process that involves a lot of rejection. If you pitch a piece, wait two weeks to hear back, follow up, then wait another two weeks only to be rejected, then you’ve already spent a month on just that one pitch and have nothing to show for it. (Keep in mind that simultaneous submissions are a big no-no in the magazine/digital media world). Publishing takes even longer – you can submit an article, and not see it in print (or get paid for it) for two or three months.

For me, what works best is to plan quarterly. It’s much more realistic for me to write 15 pieces over three months than it is to write five pieces in one month. Ultimately, it’s the same amount of work, but it gives me the wiggle room I need to focus on achieving my goals instead of feeling frustrated at a perceived lack of accomplishment.

You may be asking, why three months? Why not four or six? I will say that sometimes I’ll give myself an extra month to achieve a certain goal, but overall, I find that three months is a sweet spot planning-wise. It’s long enough to give you a reasonable amount of time to accomplish something tangible, but it’s short enough that you’ll still remember what your goals were from start to end. If you’re planning every six months, what can end up happening is that you get to your six month mark only to find that you’ve forgotten half of what you’d set out to do, and now you’re so off track it’s hard to muster up the motivation to recalibrate yourself. Three months is the Goldilocks of planning times.

Plan for opportunities, not idealizations

What I’ve discovered is that planning pushes you to take steps that will ultimately open up new opportunities that will help you achieve your goals. If I want to take on one new client every quarter, planning gives me the opportunity to sit with myself and think, ‘What do I need to do to be able to achieve that goal?’ Networking is probably going to be on that list, so I plan to attend three networking events each month, for example. Instead of getting tunnel vision staring at my new client goal and then beating myself up when it doesn’t pan out, I’m pushing myself to create the opportunities that will get me there. Even if I don’t meet my goal, I’ll have almost certainly gained something for having stuck to my action plan.

Adjust, adjust, adjust

When I create my task list for each month, I reference my quarterly goals. Then, at the end of the quarter, I sit and take stock of what goals were achieved and in what time frame. Sometimes, I’ll find that I’m still working towards a goal – I’m making progress, but I haven’t gotten there yet. Other times, I find that I’ve completely fallen off the wagon with regards to one goal. Maybe I started out the quarter strong, but since then it’s taken a backseat compared to other goals. That evaluation helps me figure out how to organize and manage my time, and it helps me readjust my expectations to match reality. Perhaps more importantly, though, is that it helps me really think about what my priorities are. If one goal has been completely forgotten, maybe I need to set it aside for a while and zero-in on what I’ve gravitated towards over the course of those few months.

This is part of why I prefer to plan quarterly as well – it’s hard to figure out priorities and work trends over the course of one month. Three months gives you a much better picture of what your work life actually looks like, while at the same time being short enough so that you can consistently assess yourself and stay on track.

Ultimately, how and what you plan is up to you, but hopefully my approach will help you brainstorm one of your own. In Planning Your Creative Career Part 2, I’ll be discussing my planning system in more detail, showing you the tools I use and how I use them. In the meantime, check out these new year planning tips and these writing goals (which can totally be adjusted to whatever you do as a creative).